Sugar Baby Weekly

Obama in My Bed

2008-11-04T09:49:00.001-06:00

I don't need any more t-shirts.

But last time we were in New York, The CEO was packing up his case to leave our hotel room and tossed a white t-shirt into the corner.

"You're throwing it away?"

"I just bought new ones, so yeah, I'm leaving this one behind."

Then he kissed me, handing me a very fat envelope, and pressed his forehead into mine.

"I'll see you at the airport."

"See you there."

A week later he came over early in the morning and jumped into bed with me. I giggled and we made stupid conversation as he pushed my t-shirt up and sucked on my nipples.

The man spent a long time going down on me, and I congratulated myself on an excellent job of teaching him oral techniques that work.

He's so good at fucking me now, and it's easy and sweet and nice and a little bit sad all at once, but I usually manage to keep the mood light. With his cock pressing nicely against my G-spot, he pulled back and smiled down at me. He pushed the hair from my cheeks and said something about how rosy they were; about how nice I looked.

So...

"Do you like my t-shirt?"

"It's soft."

"It's yours."

"You stole my t-shirt?"

"I rescued it."

"Ahh-from New York. I remember. It smells good."

"That's because I haven't washed it. You smell really good, Mister."

Hopefully not too creepy. Hopefully he just finds it charming, like my other idiosyncrasies.

I threatened him yesterday that when Obama wins, he's going to have to fuck me while I wear my MoveOn.org t-shirt.

Yes, We Did!

He's coming over now. And Obama is stretched tight across my chest.

Something So Familiar

2008-01-27T22:34:00.000-06:00

A couple of weeks ago I received an email from Viviane of The Sex Carnival asking whether she should add my blog to her list of the dearly departed sex bloggers. "No!" I practically screamed at my Gmail.

Her point, and that of several of you, dear readers, was well taken: it's been way long since I spent quality time, just me and my keyboard, pinging out the stuff that feeds your imaginations and dammit, makes me smile to read it over again. I could tell you that things have been busy at work (they have), or that I went to St. Moritz over the holidays (I did not, but I could tell you that), but the truth is that I've been very lazy and more than a little bit conflicted.

Lazy because, well, it's easier to stay in the habit of not writing than it is to forge a whole (almost) new one of writing more regularly.

Conflicted because I had this dream.

It was a couple of months ago, after a business trip with The CEO where we spent 42 hours together, about four of them sleeping. We went shopping, ordered room service in our swanky hotel, walked on busy streets in broad daylight and ducked into a bistro for lunch. That was the trip where he referred to himself in the third person as my boyfriend and it caught me off guard.

So, in the relevant part of my dream he and I are in his car and we go to pick up his two sons. I move to the back seat and start having a conversation with one of them. Then the CEO stops and runs into a shop to pick up something. Basically, I am tagging along for errand-running. The boys have some kind of practice, and he's dropping me off at my house. He pulls up, gives me a quick kiss, and as I am opening the door and stepping my foot onto the pavement I say, "'Kay, byeloveyou."

I know. I KNOW.

And as soon as she said it, the dream me clamped her hand over her mouth and omigodded.

Then of course, I woke up. Then of course, I freaked out. Am I seriously in love with The CEO? I mean, it would be alright to be in love with him if A) he wasn't married, and B) didn't pay me. That's WHY you look for a girl friday--or wednesday, as is often the case--to avoid emotional entanglements. And here I was getting emotionally involved.

Alright, so now I'm emotionally involved.

I told my friend who used to escort what happened, and I tried to think about what it really was that made me say such horrible things in my subconscious. It was, after all, a dream, and not necessarily meant to be understood literally. I decided that I'd explain it to myself as a natural progression of things; as in, I'm increasingly comfortable in his presence, and isn't that what people who are comfortable with each other do? Isn't that what people with a certain familiarity say to one another?

It's what I say to my friends when we hang up the phone or say goodbye on a street corner. Quick cheek kiss, hug, "loveyoubye!"

For about a week I was conscious of how many times The CEO and I spoke. I made myself let his calls go to voice mail and returned them later. I focused on my job and my friends and not on how much I would miss seeing him when he took his family to Australia over Christmas.

I didn't tell him about the dream. And apart from those ten days last month, we've seen each other for sex and familiarity every week, once a week. Sometimes twice.

Girlfriend

2007-10-27T22:17:00.000-05:00

It's happened so gradually I didn't even notice it at first: I think I'm the CEO's girlfriend.

I guess the first inkling was in DC, when he kept making remarks to Gwen about how great he thought I was, "Dude," she said, "he's so into you."

Yeah, but this was also the first time we'd gone away together, you know? And it was exciting and fun and thrilling and a risk. So I'd basically chalked up his fawning to enthusiasm. We'd had great sex, seen not much of each other for most of the trip, and sat as far apart on the return flight as we could: him with his CFO in the rear of the plane and me with my Blackberry in the front.

I was glad we'd done it--glad that I'd been able to share my friend with him, glad to have slept between them in that big bed, and surprised at how nice it felt to turn and see him beside me.

A month later we took another trip together, arriving at our destination in the evening and seeing very much of each other until his meeting the next afternoon when a car picked him up and another drove me to the airport. A few days before this trip he mentioned to me that he'd been re-reading our first emails to each other and remarking that this was so great; that we were each exactly as we'd made ourselves out to be.

"Uh-oh," I thought, "that is what people do when they are in love: they read old emails."

Still, the time we had together was great, and very, very sweet. There was a moment when we were fucking that I could almost sense those words on his tongue: those words that make things complicated. He didn't say them, and I was mostly glad. Mostly, because it's always nice to hear how besotted someone is with you, especially when you already have a hunch. He played a song on his iPod which he said always made him think of me. So now I have a song. Fortunately, it's a good song.

Unfortunately, I like him very much and I'm well aware that arrangements like ours don't last forever and that someday he'll decide that it needs to end and there I'll be, sad and missing him whenever I hear it.

Last week we were traveling together again, on a short overnight trip. He was leaving for Europe, and handed me some cash for when I checked out the next day so I could pay for the room service charges and the bottle of champagne we'd drunk, leaving the suite charges on his company card, "Tell them your boyfriend already left, but you want to remove those charges from the bill."

I don't think he even realized he'd said it: boyfriend.

But I did.

Naughty

2007-09-20T21:30:00.000-05:00

I was so horny when he texted me to say he was on his way. I said as much when I texted him back.

It was 2:30 in the afternoon and I had nothing to do for the rest of the day. So I had a drink: Absolut Mandarin on the rocks. Perfectly civilized, no? A little citrusy-cool-sucking on ice cubes interlude in the middle of the day never hurt anyone, right? Just ask Hemingway. Oh, wait, on second thought, don't.

The CEO came in and I offered him a drink. He had a water bottle and declined. Sure, fine. He doesn't come here to drink, anyway.

The man can undress faster than anyone, and he was naked in seconds. I shut the bedroom door so the kitties couldn't wander in. He towered over me and I grabbed the back of his neck. He sucked the taste of the vodka from my tongue and I reached out for his cock. It's nice that I can just put my hand forward to stroke it, feel its velvety head under my thumb and the steady throb of its pulsing.

"What's your pleasure, Miss?"

"I would like to suck this cock of yours right now. That's what I want."

His grin was hilarious.

So I blew him. And then we fucked. He was sweaty and I loved it when he wiped his forehead and spread the sweat on my chest. So. Damn. Hot.

We lay in my bed, watching the fan and talking. He asked me to go on another business trip with him in a few weeks.

"I'd like that a lot," I said, "I like doing naughty things with you, Mister. I want to do more."

"What kinds of things?"

"Well, like now, for example, I'd like you to fuck my ass."

He sighed and his dick twitched, waking up again.

"...but first," I continued, "I'll need to warm up. Wanna watch me?"

"Um, YES."

I hopped off the bed and grabbed my bullet vibe and a butt plug. I put the bullet in a condom and lubed my ass. Kneeling on the bed next to him, I slid it in and handed him the controller. Then I bent over him and rubbed the full length of my body on his. He played with the speeds and I ground my clit against his hipbone.

It felt so good, and in another frame of mind, I would have stayed that way for a long time, but he didn't have all the time in the world, so I pulled back, "Time for Stage Two," I whispered.

I pulled the bullet out and removed the condom. I squirted some lube onto the plug and said, "Watch this."

On my hands and knees, with him kneeling behind me, I positioned it at my hole and sighed as it slipped in. He was breathing hard and said, "Oh, jeez." I giggled. "Another first?"

He swallowed and nodded. Good.

I flipped over to my back and took the bullet in my fingers, "Now I'm going to jerk off for you."

My clit was already swollen and sensitive and it didn't take long before I was squeezing my asscheeks together and pushing my hips up. My knees were apart to give him a nice view. I reached down and took the handle of the buttplug, slowly moving it in and out, bringing myself almost to orgasm, but stopping short. I told him to cover his cock, handed him the lube and removed the plug.

I raised my legs up. I wanted to see his face when he slid into my ass. He used a ton of lube (good man), and slipped in easily. Freaking bliss.

He knows to fuck my ass slowly. I've given him extensive information in preparation for this event and he performed flawlessly. My calves were on his shoulders and I rubbed my clit between our bodies. He looked so happy, and I was crazy hot for him.

I think it's because I'm very particular about assfucking. I often feel violated and unsettled afterward, the sensation of a hard dick stretching my butt fading only after an hour or more. But this? This was phenomenal. Like, I finally understood what all the fuss was about.

I came so hard that I pushed him out. I think he would have stayed out, assuming it was over, but I whispered, "Put it back, put your cock back in."

Business or Pleasure?

2007-08-23T23:19:00.001-05:00

"Cara, he's so hot!"

"Yeah, good thing he's married."

"Keeps things simple?"

"Exactly."

Gwen and I sat on the couch in the sitting room of my suite in DC. The CEO had just left for dinner with business associates and would return in about four hours to resume where we had left off.

I'd landed that morning at the airport and took a cab to the hotel. I checked in, unpacked my bag and headed downstairs to the front doors. I walked up to the bell hops and was greeted with a "Yes, Miss? What can I do for you today?" (Ok, I love the way I get treated in expensive hotels, and I know it's all put-on, because they are supposed to make me feel special and kiss my ass and all that, but still it's nice.)

"I need to go shopping. I need to go to Tyson's Corner."

"Of course, Miss. You need a cab? Roundtrip?"

"Yes, please."

He (Will) picked up the phone and spoke, telling the driver I was waiting and that he needed to get there quickly. I smiled my thanks and sat down to wait. Somebody brought me a coffee.

I was going to Tyson's, not because I wanted to kill time, but because the CEO had made me an offer. He suggested that when he was at his afternoon meetings, that he would send me shopping, "loaded for bear," and my job was to spend all of the money. Let's say he gave me a thousand dollars, then he would expect me to spend all of it. I balked a little, because I really dislike shopping, truth be told. (I know, bad sugarbaby trait, what can I say?) I much prefer gifts, or shopping with someone who's buying me things. He insisted, going on to say that if the amount I spent was less than the agreed-upon total, I would owe him double the difference. Like a game show. Fuck me.

I consulted with my shopaholic friends and decided that I could, in fact, use a few nice things. Jeans that actually fit and make my ass look great, for example. Shoes. A new camera. Accessories for the iPod he'd just given me last week. (That was awesome: he came over early one morning with coffee, the paper and, "Oh, here's a present for you. I know you'd have preferred pink, but the 8Gig Nano only comes in black and silver." Hello, nice little black iPod!) So, my friend Astrid gave me some good advice: Go to Tyson's Corner. There's a Nordstrom's there. At least the jeans and shoes could be taken care of. I was sure there would be a Best Buy or something there where I could get electronic stuff.

The cab dropped me at Nordy's and would return in two and a half hours. Not much time, folks, not much time at all. I scanned the shoes and decided that it would be best to get them last, considering their bulk and all.

I went up to the Women's Apparel floor and sought out a tall blonde named Christin. Verbatim: "Ok, so here's the deal. I need a pair of great jeans that fit me. Here's my body. I am prepared to spend a lot of money, but I need you to help me." Her eyes lit up and over the course of the next 40 minutes she brought me jeans, advised and approved. When I found the pair I loved, the ones which made me look skinny and hott, there was just one problem: they were about four inches too long.

"We offer free alterations," she said.

"Well, I'm not from here, I suppose I could have them altered at a Nordstrom's near me?"

"How long are you here?"

"'Til tomorrow, but here at the mall for another two hours."

"We'll rush them. I'll call the seamstress now."

Hot damn, did that just happen? "Oh, that would be great!"

I paid for the jeans, telling myself on hearing that she was a teacher, that I'd come back through and buy a few more things to pad her commission. I like teachers. I think it sucks that so many have to work extra jobs to make a decent living.

I walked out into the mall and found a Directory. I scanned for Electronics. Mother Lode of Mother Lodes, there's an Apple Store. I made a beeline for it. The place was, as they always are, teeming with shoppers. It kind of smelled like sweat (not in the good way). I played with a new iMac (goddddd I want one). Then it dawned on me that The CEO had never actually given me a set figure for my game show shopping spree. I texted him.

Me: So, did you ever give me a goal for this shopping thing? Because I don't think you did, and I think you probably should.
Him: Just spend and I'll take care of it.
Me: You so totally rock.

For a fleeting moment I imagined the iMac in my home, all sexy and white in my black computer armoire, replacing the dinosaur that lives there now. Then I remembered that I'd have to cart it home on the plane and besides, there's an Apple Store near my house and I probably would only have to mention my lust for the iMac and it would be mine if I wanted it. I headed toward the things I knew I needed and which were small enough to pack: A case for the iPod, noise-canceling earbuds (swoooon) and a car adaptor. Now that I think of it I should have gotten the MS Office Suite for Mac, but live and learn, eh?

I had about an hour left, and I was nowhere close to my estimated spending threshold. I needed a slew of DVDs. TV serials on DVD are expensive, no? I could get a bunch of those for myself and friends. Then I saw the Gap. I should never have gone in there. 30 minutes later and I'd spent a mere 62 dollars on a dress and two tops. I am such a retard.

I hurried back to Nordstrom's, picked up my jeans and a Free People top and rushed downstairs to the shoes. Nothing, but nothing killed me outright. I ended up buying a pair of Steve Madden black patent Mary Janes and some suede wedges with bows which were cute and comfortable. Ugh. I was hating this. I ran back to the Hosiery department and picked out two matching pairs of thigh-high stockings for myself and Gwen (more on that later), and decided that, since it was cool and rainy, I should have some sort of wrap or sweater for the evening. I checked the time and ran back upstairs.

I spotted some gorgeous sweaters and flipped through them. XS and XL. Fucking great. Then I spotted a dress I had to have. It was totally impractical, seasonally speaking, but it was by an awesome designer and it was on sale. I found my supposed size and rushed over to the saleswoman with the funky glasses wearing clothes by the same designer.

"Hi," I said, a little breathless, "I need to try this on, and I don't have a lot of time."

She whisked me back to the fitting room (dudes, my bathroom is not that big). I slipped into it and forgot all thoughts of sweaters and wraps. This dress was coming home with me. I paid at the counter and thanked the woman for her help. My cab was waiting downstairs.

After paying the fare and giving a rather large tip to the driver I walked to the elevator loaded down with bags. I stared at the numbers lighting up and the guy in there with me said, "Looks like somebody had a productive day!" I grimaced. I'm sure of it. "Uh, yeah, I guess?" Did I mention how retarded I am?

Back in my suite, though, I unpacked my purchases and tried on the jeans. They fit like a motherfucking glove. Two Hundred Dollars well spent, if you ask me. I've never had jeans fit my ass so well. I put on the Gap dress and the Mary Janes and answered the door for The CEO, who had finished with his afternoon meetings.

He beamed when I let him in, walking into the sitting room and practically jumping up and down. It was the first time we'd seen each other that day and he'd made sure to get a room on the same floor as mine for appearances. "We're really doing this!" he said, and I laughed. It was pretty surreal. I showed him my things. Well, not all of them, because Gwen called on her way to the hotel, five minutes away. I told her the room number and suggested to The CEO that a good way to break the ice would be for me to be blowing him when she came in.

I was on my knees, still wearing the black dress and patent leather, when she knocked. I kept my mouth on his cock and reached behind me for the door handle, pulling it toward us. She stepped in, the door closed and The CEO said, "Hi, Gwen!" She literally jumped and yelped in surprise. I laughed around his dick. Gwen's seen me in all sorts of situations, so I wasn't worried about offending her. I kept blowing him as she set her bags down and went to wash her hands. The CEO suggested we move to the sitting room, "to get acquainted."

As I continued to suck his dick while he sat in a chair, he talked to Gwen: "Don't you think Cara looks amazing? She's so hot." Gwen laughed and nodded, "Yes, she is."

"You like the way I suck your cock, Mister?"

"Man, it's awesome. Gwen brought wine, that was nice!"

Gwen pulled out three bottles of red wine, "Does anybody have a corkscrew?"

I looked up at The CEO and sighed, "I'm going to take care of that. Your cock isn't going down anytime soon, is it?"

He shook his head, "No way, man."

I called the front desk and ordered a corkscrew and glasses. After a glass of wine, the CEO looked at his watch when Gwen was in the other room admiring my new shoes, "I only have another 30 minutes until I meet the stiffs for dinner."

"Then you'd better fuck me. You wanna fuck?"

"Yeah, is Gwen cool with that?"

"Hey, Gwen, you're cool with The CEO fucking me, yeah? You've seen me get fucked lots of times, right?"

"Hmmm, seen you get fucked, or fucked you? Because I think they're about even."

Aw, touche!

In a second we were all in the bedroom, Gwen with her wineglass sat in a chair and The CEO was naked.

"Hey, Mister, turn around! Nice and slow for us girls."

I turned to Gwen and whispered, "Nice ass, right?" She nodded, eyes wide. "He's tall, too," I continued, "and the man can fuck."

I took off my dress and shoes and walked over to the bed in a black bra and leopard-print tangas.

"'sup, tan lines?!" Gwen exclaimed. Last time I saw her was in the winter.

The CEO was still sporting his hard-on. I lubed it with my tongue and rolled a condom onto him. He took off my panties and flipped me onto all fours. He fucked me like that, and it was damn good, but my favorite way to fuck him is from the front. See, he's got this awesome upward curve to his dick...

"Turn me over," I panted, after a few minutes. He did, and pulled my legs over his shoulders. And. It. Was. Awesome. Every stroke hit my g-spot. At a point I looked over at Gwen and smiled. Then I totally gave her a thumbs-up. She laughed and shouted, "Oh, you did NOT just do that!" I laughed and said that I DID, and came.

A minute later he whispered to me that he was going to cum. "I want you to cum, cum for me, that's it, I love when you cum for me," I whispered back. It's great how excited he gets when I tell him to cum. How he speeds up and pushes himself to do it.

A minute later he was in the shower. Two minutes later he was kissing me goodbye and bouncing out the door for a few hours.

"Damn," said Gwen, "that was hot; he's so big and pale and you're so little and tan. He's awesome."

"I know, right? You'll find out firsthand later."

Dressing Up

2007-08-11T10:40:00.000-05:00

Have I mentioned how I love dressing up?

I think I have, but for those of you new to the blog, let me be clear: I really enjoy dressing for sessions. It's my little ritual, which we all have, like for dates and stuff. And of course you want to wear something on a date that your boyfriend will like, but you don't (at least I don't) ask him what he wants you to wear.

Girls also dress for other girls. We're constantly checking each other out at the supermarket and the swimming pool (I was at my pool the other day and this searingly hot Amazonian fox was wearing a bikini top and these really weird coordinating shorts, i assumed to cover her ass. I was incredulous. She totally should not hide her ass. Of course I didn't say anything. Of course I digress.)

I dress for the CEO the way I know he likes. I asked him what he'd like me to wear for his commencement speech.

"Dress like you're a recruiter for a big hi-tech company."

"Like, what, a suit?"

"No need. Dressy business wear. It's summer."

Excellent.

So I got dressed that morning, after painting my toenails a nude shade of pink. I checked the mirror one last time before heading out: my white blouse with the semi-seethrough swirls in the fabric, nude colored bra underneath, a black pencil skirt with a flare at the knees, and black strappy heels. I had my red briefcase filled with condoms, lube, a vibrator and my laptop.

He was nervous when he walked into the hotel room. I took his bag and kissed him hello. His assistant had messed something up at work and he was flustered and annoyed and needed to leave the office to fix it. And now he was here with me. I lowered my voice about an octave and spoke quietly. It works with my cats. I undressed him and kissed his mouth to shut off the rambling.

His eyes were closed and he had that little smile he gets when he's relaxing, just like my cats.

It was at that point that I realized, really, what my role is for the CEO. I am the calming influence. I leaned into his ear, "Hey, Mister, watch this."

I slid down to my knees, wearing all my clothes, putting my hands on his hips and looking up at him from underneath his hard-on. "You look like the hottest recruiter ever," he said. "Sit on the bed," I said, "and pretend it's your office chair." I smoothed my hair and smiled.

I blew him on the edge of the bed and cleaned him with a warm washcloth. He said he wanted to kiss me all over. I stood up and undressed, not being showy, but definitely being deliberate. He smiled and pulled me over. He nuzzled my stomach and licked my belly button. He sucked my nipples. He turned me onto my belly and laid on top of me with his arms under the front of my shoulders. He spooned me from behind. We didn't fuck.

We showered and I brushed powder on my face as I watched him get dressed. He left ten minutes before me. When I grabbed my briefcase I saw the stack of bills in the small compartment: three times my hourly rate. Of course, we weren't finished, I was going to watch his speech and look hot from the audience. I put on the glasses he likes and looked down at my feet, "I should make sure I sit at the end of an aisle. When he sees me, my legs will be crossed and a foot dangling in the aisle."

Synchronassity

2007-08-04T02:14:00.000-05:00

The week before The CEO's commencement speech we met as usual. I checked into the hotel, he showed up in sweaty golf clothes thirty minutes later. This time, he was sweatier than usual and I was all over him. I like sweat–clean sweat–on a guy who's recently showered. I was keen to show my appreciation for his salty-slick skin, turning cold from the air conditioning, which as it turns out, had no effect on the state of his cock.

I whispered how hot it made me to taste his sweat and his cock surged even harder against my belly as I stood on my tippy-toes to reach his neck. He walked me backwards onto the bed and I scooted back, propping myself up on my elbows as he followed me on his knees. He fed me his cock and all that, and then he kept moving forward, inch by inch.

At a point, I thought, "does he want me to lick his ass?" And then, "OMG, he totally wants me to lick his ass!)

Ah-hah! The CEO likes it when girls play with his bum! How happy did this make me? Very happy, indeed.

Believe me, I'm perfectly glad to give the man an hour-long blowjob, if that's what he's paying me for, but if the possibility of a little kink presents itself, I am thoroughly pleased. It keeps my job interesting, and opens the gates for more satisfying encounters. The CEO is married, and–not that it applies to all marriages, though it's becoming clear that it's not an uncommon thing in married men–not getting any at home.

We don't talk about it, his marriage, but things slip out now and then, and from our first meeting he's been remarking on how many "first-times" he's had since then. I was the first girl he'd ever jerked off for, the first he'd watched jerk off, who'd let him come on her tits, the first to suck his cock on her hands and knees while he kneeled on the bed and got a stellar view of raised ass. I was game to chalk off a first for every time we met, but my brain was starting to quaver, trying to come up with new positions and configurations. Now it seemed I had more material to work with.

The sounds from above me as I toyed with his ass with my finger while my tongue sucked on his balls were fantastic. He was kneeling above me on the bed, bracing himself against the wall and his legs were shaking from the effort. I suggested we change positions.

"Do you like it when I play with your ass?" I asked, grinning.

"Yeah, I really, really do," he said.

"Good, because I really, really like doing it."

Unfortunately, I hadn't brought any ass toys, since this was a new revelation and I was late leaving the house. Live and learn, I thought. Not to worry, I still had gloves and lube, and that was going to have to suffice. I put him on his belly, ass up, and stuck a glove on my left hand. I pulled the condom off his cock, lubed my glove, his ass and my other hand, and started to stroke his semi-erect dick.

He likes it fast and shallow at first, concentrating on the head, and then moving into a steady and firm full stroke. I watched him jerk off on our first meeting. I blow him regularly and take extensive mental notes. Once he was hard and starting to circle his hips with my handjob, I took my other hand and again started swirling around his hole with the tip of a finger. Swirls became circles, became more insistent pressing and rubbing with my ring finger.

"Relax, Mister," I whispered, "take a deep breath and blow it out."

He did, and my finger slipped in. He took it completely, and I could tell he was smiling.

"How does it feel?"

"It's like my brain's on overload. It's so good, please don't stop."

I felt very protective of my CEO, like a mother who covers her babies with her body to keep them from harm, like that lady vampire in Interview who tries to shield Kirsten Dunst from the sunrise. It's true, my heart melted a little and I leaned over him, brushing my tits against his ribcage, bending forward and talking low, "I'll stop when you say, but I like this very much."

I kissed and bit his asscheek softly.

He inhaled as my grip tightened on his cock. I stroked it steadily, making sure my thumb circled the head on the upstroke the way he likes. Then on the downstroke I started pumping my finger into his ass like a goddamned piston firing. Both hands working toward one another, one firmly jerking his cock, the other gingerly fucking his butt.

The CEO likes to have permission to come. When I first started seeing him, he'd say, "A dude could come at any time if someone would say it's okay." I thought that was a little odd, but charming in a way, and I'd say, "You know, Mister, I would really like for you to come now," and he would. These days, I know when he's about to blow, and I'll just say something along those lines.

His dick was solid hard, his balls pulled up, the man needed to blow, "Hey, Mister," I cooed, "you know what would be really hot? You come on my hand and I rub it on my tits."

He moaned, his breathing was shallow, and the tell-tale "ah yeah, ah yeah" was happening up in the pillow. Then something not that unusual: his dick got soft, his ass tensed up and he grunted into the pillow.

"I can't."

"Okay, hold still and take a deep breath."

I retracted my finger and snapped the glove off inside-out. "You okay?"

"Uh-huh. I was so close, I don't know what happened."

"You froze up a little bit when I started massaging your prostate."

"That's what that was? I felt like I was going to die!"

"Baby," I kissed him, "you would have died a very happy man."

"Can we do that again?"

"Bet on it! Next time just let go and relax when you start to feel like you're going to die. I promise It'll be amazing."

"Miss, when you were licking my balls I thought, 'Oh, my god, is she going to lick my ass? I think she's totally going to lick my ass!"

Hah! Now that's some synchronicity.

Mister

2007-07-21T06:02:00.000-05:00

So, I've taken to calling The CEO "Mister."

To his face. Like Claire Danes' character in the movie (and book–the book is really good! And Steve Martin wrote it, the fancypants.) Shopgirl. It's funny, because it started off in my head as "Mister Big," which I would never have called him to his face. But tell a girl about your cars to the airport and private planes to The Bahamas enough, and she'll come up with a suitable pseudonym for you. Soon, "Mister" worked its way into my greetings to him.

As in, "Hi, there, Mister!" Or, "Hey Mister, roll over so I can put my mouth on your cock." Stuff like that.

Following suit, he started calling me Miss.

It adds to the discreetness and covertness of our relationship, and it's not icky Dominant/submissive like it would be if I called him Sir. Which I would never do. Because, eeyew.

One day we were lying in bed at a hotel near his golf course while he was supposedly playing the back nine, when he asked what I was doing the following week, "Um, seeing you?" I replied.

"I hope so, but get this: The Business School at XYZ University has asked me to speak at their Commencement that day."

"Wow, Mister, that's special!"

"Yeah, but I suck at public speaking."

"Would it help you relax if you were sucked before speaking in public?"

(A-hahahaha. I crack myself up.)

"Miss, you read my mind. That could be just the thing to take a fellow's mind off of speeches. I'd like you to come to the thing, too, if you could."

"Wouldn't it make you nervous if I was there?"

"No, I think I'd feel better knowing you were out there. We could meet here and then drive over separately and come back to the room if there's time. So, yeah, I'm talking about all afternoon."

Oh, the prospect of this got my knickers wet.

Airports

2007-06-14T16:00:00.000-05:00

Airports are funny.

I am sitting in one now, pissed off that my flight is extremely delayed and looking at a group of business types standing around and holding their smartphones and fiddling with their Bluetooth headsets.

They are probably very important people, but it is their self-importance that creeps me out. The calling of assistants to find alternate airlines and trying to get out of the situation we're all stuck in. They will solve this problem, and get home to their crazy-big, important lives. Swimming pools. Movie stars.

Meanwhile, I am eavesdropping on their conversation and realizing that these men know my CEO. They are making introductions to one another and I have heard some of their names mentioned in his conversations about boring business events and cocktail parties.

The funny thing is, every one of these dudes is a typical Discreet Businessman and I sort of hate them. They are so smug and annoying because they have money and power. Not like the CEO, who is so "aw, shucks" about it all, which is very endearing.

Mostly, I think about the "business trip" the CEO is planning for us in August (the only real business being the hard, pressing one in his pants). I can't remember the last time I traveled with a companion, but I enjoy the idea of this trip. Except now, in an airport on the other side of the country I realize that the possibility of running into people who know him is high. We will probably sit separately on the flight and act like we don't know each other. Which could be fun, anyway.

Or we could sit together and pretend not to know each other. Which would probably be more fun, because he is easily embarrassed and I enjoy making him blush by talking about dirty things like sex. He called me today, when I was in the cab on my way to the airport and I asked him if he missed the way I sucked his cock. Knowing that the driver could hear me made him blush. I could hear it in his voice. So, sitting next to him on a flight and him knowing what would be in store for him once we reached our destination would be delicious. Perhaps flipping through a copy of Maxim, being sure to linger so that he could look over and be crazily turned on while I coyly ignore him.

I will join him in August for this short trip.

I will do this because the fun we could have on a getaway blows my mind. Because I enjoy making him feel good. Because jet-setting is cool. And because, well, the Presidential Suite at the Four Seasons sounds like a semi-decent place to spend the night.

Taco Bell! Motel! LOL, I'm in Hell!

2007-05-21T15:46:00.000-05:00

The following is an actual email from a prospective client.

Well, I would like us to meet at the taco bell...if you want to go further
then we go to the cheap motel room that is close by....we go in the room and
you drop to your knees and service my cock for awhile or till I blow my load
on you somewhere....and or we go into the room, you get on the bed, spread
those legs and let me at it! lol....either way I leave you with some
funds...
sound like what you thought?
if so when would you be free?
how much funding are you in need of? if we do this semi regularly it would
be nice....
reminder that I am paying for the room and I am not rich...lol
-James

Nice, right?

Gentlemen, please. His previous suggestion was that we meet at "a designated place near the baseball stadium," to which my response was "that sounds like a nice invitation from an axe murderer. I will only agree to meet you at a hotel, but if you'd like to meet at a restaurant for an introductory lunch, that's a possibility."

Apparently, he'd meant the taco bell across from the stadium was the "designated place" and I could look forward to a cheesy gordita experience of the highest caliber before sucking cock in a cheap motel, "lol."

Here is the part when I say to you, dear readers and friends, puhlease.

I understand the turn-on of a seedy motel room for some. I know a married couple who spends the night every Valentine's Day at the cheapest motel out by the airport they can find, because it's fun and also hilarious and it's become a tradition. But as a proposed regular thing? Because some poor schmuck can't actually afford to live his fantasy?

Nope, sorry, "James."
I am not the girl who blows you twice a month in a no-tell.

I am the girl who is looking at an empty bottle of Veuve Clicquot Ponsardin champagne which The CEO brought when we met last Friday. I drank this bottle with him, naked, as we leisurely enjoyed each other's company in stellar accommodations. I taught him about my g-spot, he clued me in on some of his favorite techniques, which I put to use, making him cum three times in as many hours. We compared Blackberry features and he suggested that I join him on an upcoming business trip.

He is fun and hot and knows how to do this right.
And he is also paying for the room.
Because he is rich.
"lol."

Panty Ho

2007-05-15T22:39:00.000-05:00

Do you have any idea how hard it is to find true sheer-to-waist pantyhose?

Pantyhose. As in the kind which start at the toes and magically, seamlessly go all the way up past one's belly button.

Last week The CEO suggested that I might wear pantyhose for our date. I liked his explanation of his fascination with stockinged legs: "...it seems like women don't wear hose to the office anymore." Sweet, right?

My poor CEO had spent so many years NOT looking at women's legs for fear of being thought of as lewd and now female employees don't sheath their legs in nylon or silk the way he likes. I could do that. I love to do that. Even if his real reason for loving hose was that he spent his youth watching his mother dress for Bridge Club, waiting until she'd left, trying on her pantyhose and rubbing his feet and legs together. Whatever the reason, I was happy to acquiesce to his request.

My mistake was in assuming that he, like most men I am acquainted with, uses the terms "stockings" and "hose" interchangeably.

I had arrived at the hotel half an hour before him, stripped and changed into my garter belt and silk stockings. We had a great time, despite the business traveler hotel accommodations, and spent two hours naked but for my stockings and garter belt.

As hot as I looked, and as appreciative as he was, when he emailed me last weekend to set our next date, he reiterated: "maybe you could wear actual pantyhose? not that the stockings weren't awesome, because they were, but maybe sheer pantyhose in a lighter color?" He also suggested I dress as if I were going on a job interview.

"Ah," I responded, "so now it comes out. What are you, some kind of perverse degenerate, man? Pantyhose? Pantyhose? Interview? Sheesh. Okay, but I'd better get the job."

Getting dressed was almost ritualistic. I don't wear pantyhose as a general rule because I am short waisted and pantyhose waists always roll down and annoy the hell out of me. If I cover my legs it is usually with garters and stockings or thigh highs. Today, as I pulled the waistband up to my hips and stepped into the crepe skirt I thought about what The CEO had said last week: that my body was perfectly suited for the 1950s. That I'd look great in a clingy off-shoulder gown and pumps. I had to agree, and as I smoothed my palms up my calves and thighs, I was kind of turned on by the pantyhose thing.

I was waiting when he knocked at the door. I closed it and spun to face him, striking a pose and swishing my hips a few times. I had dressed for an interview, in a tailored black skirt, white blouse, nude pantyhose and red slingbacks. The skirt was slightly flared at the hem, hence the swishing of the hips.

He was pleased with my outfit, and I began to see what he found so exciting about ladies in business skirts and hose. I tucked my feet underneath myself on the sofa and unconsciously tugged down on the hem, modestly covering my knees.

Well, that was hot.

We sat and talked while he stroked my legs and my feet made their way to his hardening dick. Since he had a dinner meeting later, I took his pants and shirt and hung them neatly over the chair. My skirt and blouse and shoes got tossed into the chair, but my pantyhose stayed on.

Through a lengthy blowjob, a move onto the bed, a through-the-pantyhose dry hump and a kissing lesson, my legs, stomach and ass were tightly encased in the surprisingly strong nylon. Eventually the hose came off, which gave me a fleeting feeling of vulnerability. I was in bed with this successful, driven businessman, who meets me to escape being powerful and who has a terrific time hanging out and always tells me, then and also in phone calls afterwards.

The vulnerability and uncertainty passed, and The CEO and I ignored the vibrating alerts from my phone.

We showered together, each one rushing off to the next thing, and as I towelled and shook out my hair he said, "It's so awesome that you look perfect just after a shower. No makeup, no hairdryer, just you. Do you have free time on Friday afternoon?"

"Friday, like, three days from now?"

"Yeah, I know it's short notice, but my assistant is out of the office that day."

I grinned and kissed him, "I think I'm seeing you?"

"Awesome."

Man, I totally aced that interview.

Finally

2007-04-28T08:28:00.000-05:00

I started thinking that maybe I should just hang up the whoring shoes.

The Gentleman had checked out, with my blessing and encouragement (he's really not cut out for this kind of relationship emotionally, not to mention financially). I hoped I'd been a fun distraction, that maybe he'd learned a little about how to ask for what he wants, and had gained an appreciation for his partner. He still contacts me occasionally, and I steer clear. Simply, he cannot afford me and I'm not going to reassure him that, no, I don't think he's a terrible person, blah blah blah.

After The Gentleman, there was a string of several forgettable men, none of whom excited me, and a couple of whom really pissed me off. Disrespectful, presumptuous, stupid and rude, these were definitely not people worth my time and effort: No, my fee does not include the cost of the hotel room. No, we can't forget about the condom. No, the fact that you're paying me doesn't mean you get to do whatever you want.

Hmm, apparently I haven't totally forgotten them.

While I liked the money, I was not so hard up for cash that I had no other options. I started thinking about what I liked best about my relationship with The Gentleman. I realized that I was filling a void for him, and that I was fulfilling a fantasy. I was helping him socially, not just putting on strip shows and tying him up. He thought I was wonderful, and he told me so every time we met.

In my meetings with these potential candidates, aware that they were judging me as much as (actually, more than) I was judging them, I concluded that I was having precious little fun and that this was beginning to feel like work, which meant it was time to take a break. So I did.

Until last week.

I was apartment searching on my city's Craigslist when the temptation struck. I went to look at the Personals, just to see what was there. The usual any girls want to get licked? and i got what u need- u must host- tonight only! were passed over. For real, dudes, the honor of a click from my selective thumb is given to those posts containing the words "businessman," "generous," or "discreet;" preferably all three, with discreet spelled -EET, not -ETE.

As if by magic, Generous Businessman Seeks Discreet Daytime Encounters called out to me like a siren, taunting my index finger into tracing indecisive circles on my trackpad. What the hell. I clicked, responded and within 12 hours was exchanging emails with someone engaging and clever. His email contained his first and last names, which I Googled. He was, indeed, the CEO of a successful company. Early 40s, pleasant-looking from what I could tell (of course I did an image search), and involved in several local charities.

Our conversations were easy and respectful. No "so how much do you charge and what do I get for that?"; no "can you come to my office parking lot so i can suck on your toes?" In fact, nakedness wasn't even mentioned except circuitously, and I liked that. We arranged to meet for an hour. His travel schedule was insanely full, and his assistant managed his calendar. He had a window today at 1:30.

He was tall, taller than his photo suggested, at well over six feet, and very good looking. We sat together and chatted about music and art and sports. He smiled at me and said, "You're such a delight!"

"I hope to be," I said.

Within minutes we were naked. He had described himself in his ad as very fit, and I couldn't argue. He was lean, not overly muscular, and his head was bald on top and shaved on the sides.

He was, in my estimation, hott.

He'd appointed me keeper of the clock and unfortunately time was not on our side. I suggested a massage for his back and glutes, which must have been tight from all that triathalon training he was doing. omg totally awesome bodyyyy Um.

The massage didn't last long. My curiosity got the better of me and I slipped my hand past his well-formed ass, down between his legs, which he parted, lifting his hips slightly. My other hand reached around front and wrapped around his Very Hard Cock.

I hummed my approval at this (not-such-a) surprise, and suggested he turn over. He did, and stretched his arms over his head, affording me a rather nice view of him from stem to stern. His ankles were off the end of the bed. Damn, but he was tall.

After several minutes of continuing our conversation (what was it about, again?) as I played with his dick and balls and sat next to him on the bed, I leaned back, mid-sentence and stuck a condom in my teeth.

He stopped talking, mouth agape, and watched me position myself between his legs, my right hand holding his cock like I was some kind of fighter pilot. I set the condom on his head, balancing it like a jaunty little tam, smiled up at him, and rolled down his shaft with my lips.

I thoroughly enjoyed blowing him, hearing his voice when I took him down my throat and moved my head front and back slightly--quickly--until he sucked his breath and raised his hips up and came quietly.

"Very nice!" I commended.

"Uhh, easily the best I've ever had," he said.

"Really?!"

He laughed, "Um, YEAH. You're awesome!"

After ten minutes of making out and him licking and sucking my nipples, he was hard again. Wheee! When I commented on his hard-on, he said something like, "I don't mean to sound conceited, but yeah, I'm a good dude." That cracked me up. I couldn't believe I was having so much fun.

I suggested he let me watch him jerk off, which he was a little hesitant about. He's never done that for anyone, but "If you think it's hot, I think it's hot." I assured him that I thought it was very hot, and that I'd assist him if he wanted.

"Would you like some lube?"

"Uh, sure..."

He was propped up on one elbow and stroking his cock, which he held pointed up for me. He was probably expecting a squirt from the bottle, but I had something else in mind. It's way hotter for a girl to spit on your cock, right? After I dropped my shiny spit onto his knob to, in my mind, a chorus of "awwww, yeah"s, I slid behind him and wrapped my arms and legs around his back, supporting his body and resting my chin on his shoulder while telling him how hot watching him made me.

The thing is, it really did.

When he was close to cumming, I took over, jerking his dick and pinching his nipple as he arched his back into me and shot again. Um.

"Wow! You ARE a good dude!"

He had to leave, so we rinsed and dressed. I was running a comb through my hair when he came over and said, "I am so glad we met. I even came prepared in case I really liked you," putting something into my pocket.

"Oh, thank you! I had a great time...I'm glad we met, too!"

"I'm out of town for a week, but I absolutely want to get together again soon."

"I would like that very much. Definitely."

I let him leave first and waited a few minutes. I really had fun, really liked this guy. Maybe it's bad whore form to feel charitable toward someone who's paying me to get his rocks off, but I look at it as an added bonus. I get to make money and have a great time; what's wrong with that? If I were working for an agency, I'd have a totally different set of random, anonymous experiences. I'm not interested in that kind of whoring.

I was in a very "thank god--finally, someone who I like and who appreciates me and is totally cool with giving me money" kind of mood. I took the folded bills from my pocket, blinked, and looked at the clock. It had been 50 minutes since we met and he'd already paid me for an hour.

The CEO had given me a $150.00 tip.

Scarlet!

2006-12-21T18:22:00.000-06:00

Hi, all. Just wanted to post the tearsheets from the Scarlet issue. Thanks to Sarah and Alyson for thinking I'm hot.

Here's the page containing the excerpt:

And here's my bio (my BIO!) on the Contributors page:

I'm not the one with the pink hair. Also, I'm not a dude. This was totally bizarre.

Welcome, Scarlet readers.

Scarlet magazine readers and subscribers in the UK and elsewhere can find an excerpt from my post "Little Tease" in the January 2007 issue, available now.

Whee! Horny Brits, ring me up!

I've been a bit behind with the writing, but never fear--there's good, wankable reading coming very soon.

Very.

Soon.

Meanwhile, thanks for reading, and for the lovely emails. Keep them coming.

Just Lunch

2006-09-15T18:50:00.000-05:00

The Gentleman and I were off again.

For a while he'd send me an instant message and I'd flirt back, but it got to be quite boring, especially when nothing was coming from our exchanges. There were no appointments made and I was consciously keeping the conversations to mundane topics. He was not going to get free wanking material from me.

Once or twice he brought up the subject of our relationship. Mostly I ignored him because we'd discussed that topic ad nauseum and it was always the same: He thought I was great, we had a great time together, wouldn't it be great if we could be together? Let's not forget his (non-sexual) relationship with his longtime partner or that he didn't know me at all since I only revealed what I wanted him to know, or that I worked really fucking hard to make every visit unforgettable for him.

I didn't mind that--the work. All the preparation was like foreplay for me. I loved the planning, the gathering of props and the final, costumed performance. It really was like theater. The Gentleman always behaved predictably, making my choreography of our meetings smooth and seamless. I could manipulate conversations to topics I was interested in having, stretch out the cockteasing for as long as I wanted and when our time was getting short, bring him to orgasm in moments.

Come to think of it, maybe the meetings were too perfect. Could I have made myself seem any more perfect? Probably not. I was attentive to his desires, imaginative and a fascinating conversationalist who could make him cum with a few deft strokes of my tongue. Who wouldn't want to have more of that? I supposed I couldn't really fault The Gentleman for feeling conflicted about paying to play with a whore and being jealous at the thought of her fucking someone else, but that was the nature of our relationship. He knew it.

I made myself invisible in Instant Messenger, basically writing him off. I wished him well, but I knew I couldn't sustain that kind of tug and pull every time we spoke. If we had had a regular arrangement, the way it was meant to have been, and I could have counted on him to honor our appointments, I might have been able to stand his insecurities. As it was, seeing him maybe once every six weeks, I knew they would make me crazy and I would lash out at him sooner or later. I told The Gentleman goodbye, knowing I'd be hearing from him again. As soon as I was unavailable he'd start plotting to put money aside that his accountant/best friend wouldn't notice so he could see me again.

I decided I needed to move on and, comfortable in my ability to handle negotiations like this, answered an ad posted by The Benefactor.

Middle-aged, he fancied himself a "sugar-daddy type" who wanted to help a girl out with her bills. Again, he wanted a regular meeting 2-3 times a month "for mutual benefit." He didn't want to be specific about money, and I was less interested in the per-meeting sum than the reliability of The Benefactor as a regular date. We met for lunch.

Just lunch.

I Enjoy Being a Domme

2006-07-27T17:13:00.000-05:00

“You’re so sexy,” he said, reclining on the couch, “I brought you something else.”

“Another present? Where is it?!”

He reached into a bag and pulled out a paddle.

I know what you’re thinking, and I was about to get excited, but then I looked at the thing. It was a novelty paddle. Thin balsa wood or something. Shaped like a paddle, but that’s where it ended. The kind that you buy for birthday parties. I’m serious! It even came wrapped in cellophane with a marker so “…your friends can leave their birthday wishes.”

“Oh, thank you!” I hope I was successful at hiding my extreme disappointment. I've been wanting a nice paddle and this was most definitely not it.

“I’d like to spank you with it!”

“Sure. But I have to do something first.”

I unwrapped the paddle and, with the marker, wrote “SLAP!” across the silly thing.

“Let’s go in here.”

I walked into the bathroom and stood in front of the full-length mirror. The sink was behind me and I could see the reflection of my ass in it. I put my hands up high on the wall and bent at the waist, arching my back and jutting my ass out.

He spanked me, too softly, too slowly. I squirmed with each slap. I think the turn-on was how red my ass got and that I could look at the marks with him. I was careful to make sure he didn’t spank me any harder. I have never gotten marked up by The Gentleman and I don’t intend to.

When he’d finished I declared it my turn.

But I didn’t want him watching.

I took him back to the couch and told him to undress. He did, and knelt facing the back of the couch. I tied a scarf around his eyes and told him not to move as I went for my flogger and baby oil.

“This is so hot! You are so sexy! I LOVE IT!”

I came back to the couch and took his wrists, spreading them along the back of it. I leaned forward and whispered in his ear, “No more talking. Relax. You can do that.”

He nodded, turning his head so it rested on the couch.

I touched his shoulders and back lightly with my fingernails. He sucked in his breath as I trailed my way down to his ass. I kept my hands there, letting them warm his buttocks. He sighed, then made as if to speak.

“Shht. No talking unless you want me to stop.”

SLAP.
Massage.
SLAP.
Massage.

Faster and harder as I warmed up his cheeks and he leaned into my strikes, lifting his head and humming low.

I took the flogger and let it thwunk onto his upper back, pulling it down, snakelike. Again.

He exhaled shakily, ready for more.

I stood up, feet wide and let loose on his left cheek, then the right. Backhand. Forehand. Thank God for those childhood tennis lessons. I tensed my ass and stomach, took aim and exhaled on the downstroke. Adjusted my weight and threw it into the next one. I looked at his face.

He was blindfolded, but I knew his eyes were closed. A slight smile on his lips, parted slightly told me he was in the right place. I hesitated and he stayed like that. No apprehension of what would come, no fear, no goddamn talking. Call it subspace, floating, endorphin high, whatever. His mind was detached from his body and he was feeling no pain, only pleasure. I beat him again.

Then, abruptly, I stopped. I wouldn’t leave marks. And I wanted to leave him wanting more. I stood and took off my bra. Reaching for the oil, I poured some into my palm and spread it over my torso. He whimpered, coming around, turning his head. I stepped forward and put my hand on his back.

I leaned over him on the couch and pressed my naked front to his naked back, sliding slowly up and down. I whispered in his ear,

“Did you like that?”

“Yes,” he said, barely audibly.

“Do you like this?”

He gulped, nodding his head.

I reached around and took his cock in my oiled hand. He nearly jumped at the unexpected sensation. I stroked his shaft and rolled my thumb over the head as I traveled down again. Very quickly his cock stiffened more, seized and shot its load, oozing cum down over my thumb and index finger.

I silently congratulated myself for having thought to put a towel onto the couch.

“That’s it, baby,” I whispered, “Cum on my hand.”

I love being a domme. Getting paid for it is just icing on the cake.

Sugasm #37

2006-07-02T23:51:00.000-05:00

Sat 1st Jul, 06

This week’s best of the sex blogs by the bloggers who blog them. Want in Sugasm #37? Submit a link to your best post of the week using this form. Participants, repost the linklist within a week and you’re all set.

Announcements

Sex and Porn Events (sugarbank.com)
June Contest (sin.typepad.com/shauna_by_night)
Plea to the Sex-Blogging Community (spiritsex.blogspot.com)

NSFW Pics

Alison Angel and Real Peachez (sensualarousalblog.com)
Red Headed Beauty Jacinta Shot by Abby Winters (iloveabbywinters.com)
Teen Lesbian Rides Her Lover’s Tongue (simply-sapphicerotica.com)
Alison Angel Topless in Jeans (ilovealisonangel.com)
Women in Red (myhotbox.blogspot.com)
15 on 1 (pornzio.com/blog)
Anthony Guerra, Pin Up Artist (eroticandy.blogspot.com)
Cutie Playmate Sara Jean Underwood (thesexbox.com/blog)
Cum on Eileen (movies and review) (internetisforporn.com)

BDSM and Fetish

Welcum Home Daddy (redvelvetropeburn.blogspot.com)
The Making of a Cuckold - J. Part 1 (http://uk.360.yahoo.com/profile-pqPp2dY0bqgI1wN0f COZsxX1lJCR)
Spanked and Reconnected (darkside-journey.blogspot.com)
BDSM Homemakers (alternativealbany.com)
On Belts and Hotel Rooms (spankingwriters.com/blog)
Play Contract, Saturday and the Bondage Chair (everythingoze.blogspot.com)
Concentrate (masterenigma.blogspot.com)
“I Have A Surprise For You, Lil Girl” (lifeashis.com)

More Sugasm…
Join the Sugasm

(Sugasm participants should re-post all the links above. The following links may be excluded as long as you include all the above links.)

Sex Advice and Sexy Reviews

Choosing the Right Lube (creamonpants.com)
Kegel Size Me, Baby! (shayssexcolumn.blogspot.com)
Caught Red-Handed (gentlygently.blogspot.com)
How Clothes Make Sex Hotter (4thegirlnextdoor.blogspot.com)
DVD: The Noise (Lupus Pictures) (adelehaze.com)

Thoughts on Sex

Opposing Forces: Laws of Attraction (cuntinglinguist.blogspot.com)
Read My Lips: It’s Vulva, Not Vagina (msnaughty.com/blog)
Ten Ambiguously Gay Game Characters (4thegirlgamers.blogspot.com)
But Never Sexually Dishonest (orgasmcurious.blogspot.com)
Beneath This Conservative Exterior (submissiveinthecity.wordpress.com)
Eating Pussy (caramelvixen.com/vixen-blog)
The Denial (wanklog.blogspot.com)
Racist Caller (radicalvixen.com/blog)

Erotic Writing and Experiences

Comfortably Decadent - Part One (theholidaylife.blogspot.com)
Her Surprise (Part One) (aliferestarted.blogspot.com)
Swapping and Smooching on the Strip (taratainton.com)
Stories You Wouldn’t Write Home About: Jekyll, Hyde, and the Happy Whore Place (ellabeecoquette.blogspot.com)
Lunch at the Fountain of You (andrememberthattime.blogspot.com)
Theatrics (emergingontheotherside.blogspot.com)
My Turn, Your Turn (secretsofadirtygirl.blogspot.com)
Summer Vacation (kingdomofmean.com/sheets)
So Hot, So Hard (lustdemon.blogspot.com)
Loving vs. Fucking (fourstate.blogspot.com)
Two in One Day or “I Want Some Cinnamon” (dontwakethekids.blogspot.com)
Losin’ It (talktovanessa.com)
I Want a Sunday Kind Of Love… (designingintimacy.blogspot.com)
The Middle of the Night (the-sensuous-libertine.blogspot.com)
One Plus Two (easilyaroused.co.uk)
Vegas (prudence-tells-all.blogspot.com)
God is Infinitely Seductive (totalsensuality.blogspot.com)
Doin’ tha Dirty Dishes (wetbeyondbelief.blogspot.com)
Vivid Dream (dawnndirty.blogspot.com)
Little Tease (sugarbabyweekly.blogspot.com)
Fade (sexblogthis.blogspot.com)

Pinup art by Anthony Guerra, c/o ErotiCandy Blog.

Fleshbot

2006-06-15T10:24:00.000-05:00

I've been Fleshbotted!

Twice!

Thanks to Chelsea Girl and Jefferson for including my two most recent posts in their roundups! It's cool to be excerpted on a site like Fleshbot, but even cooler that two of the bloggers I most admire think enough of my little stories to say so.

I send you kissykisses, CG.

And Jefferson--well, I guess I'll just take a number.

Welcome, readers.

Little Tease

2006-06-11T07:03:00.000-05:00

I eyed the robins-egg blue box and knew what it was right away: more lingerie. I sort of got this funny feeling, like I imagine women whose husbands keep buying them corsets and garter belts and g-strings feel. I knew it was really a gift for him. I was secretly giggling.

I opened the box. Inside there was a sheer black push-up bra, g-string, garter belt and black silk stockings. The stockings were my fixation. The other things were pretty tarty, if you asked me, which was fine, but the legwear was expensive and beautiful.

Of course everything was the proper size. The Gentleman keeps notes. I found it funny that both sets he’d given me were black, when he’d told me how hot he thinks white lingerie looks, especially if it’s particularly slutty.

Interestingly, underneath my clingy dress I was wearing the other set he’d given me for Christmas. Well, the bra and panties. I don’t normally wear stockings in June.

He leaned in and whispered, “I’d love to watch you put them on, Cara.”

I handed him my glass, “Why don’t you freshen this and come right back?”

He walked back toward the ice bucket and I swiftly rifled through the twenties in the envelope and tossed it into my bag’s secret compartment. I was standing in the middle of the floor when he came back and handed me the glass. I took a sip and set it on the table.

“Femme Fatale” by the Velvet Underground was playing on my iPod speakers and I laughed to myself.

“Have a seat…the show’s about to start.”

“Oh! For me?”

“Of course! Unless you’d rather I not…”

“No! Please!”

I relaxed my shoulders and let my hips sway to the sound of Nico’s voice.

Here she comes, you better watch your step
Shes going to break your heart in two, its true

I ran my hands over my hips, tracing a line from them to my breasts, which really did look amazing in the low cut wrap dress, aided by the genius of Victoria’s Secret engineers. His eyes were bugging and I hadn’t done anything. I was just dancing. I lifted the hem of the dress to mid-thigh, never stopping the movement of my hips.

“Oh, my God, you’re so sexy.”

I smiled at him and lowered my eyes. This was so simple.

Its not hard to realize
Just look into her false colored eyes
She builds you up to just put you down, what a clown

Cause everybody knows (shes a femme fatale)
The things she does to please (shes a femme fatale)
Shes just a little tease (shes a femme fatale)
See the way she walks
Hear the way she talks

I looked at him again and kept his eyes on mine as I lowered one shoulder strap and then the other, holding onto the side button and slowly turning my back to him. I jutted my left hip out and pointed my right leg out to the side, releasing the button and letting the dress slide to the floor.

He gasped.

I turned ‘round to face him and he was bracing himself on the sofa, shifting in his seat.

“Touch yourself.”

He looked at me like he couldn’t believe I was saying that, or that I was doing all this for him. He was still dressed and moved to remedy that.

Once he had his cock out I took off the bra. I stood in my g-string, touching my breasts, pinching my nipples and dipping my finger down behind the little triangle of fabric covering me. I sucked the finger. He stroked his dick.

I hooked my thumbs under the sides of the g-string and shifted it down over my hips, stepping out of it when it hit the floor. I was naked in my high-heeled sandals, pinching my nipples and touching my clit.

Youre written in her book
Youre number 37, have a look
Shes going to smile to make you frown, what a clown

I walked slowly over to the sofa where I’d laid out my new underthings. I stepped out of my shoes and stepped into the new garter belt, pulling down on its straps, arching my back to make the most of the way my tits looked to him—overhead, but just out of reach.

I reached for a stocking and held it in front of me. I snaked my thumbs down, bunching it into my hands. I stood like a flamingo, folded over at the waist, with my leg raised off the floor, toe pointed as I eased the sheer, weightless tube up my calf, over my knee and nearly to the top of my thigh. I was completely turned on by the way it felt. Putting my foot on the sofa next to him I fastened the hold-ups and repeated the whole business with the other leg. I never took my eyes from him.

Little boy, shes from the street
Before you start, youre already beat
Shes gonna play you for a fool, yes its true

The panties followed, I stepped back into my shoes and bent over from the waist, pouring my tits into the sheer black cups of the new bra. I stood and smiled.

Cause everybody knows (shes a femme fatale)
The things she does to please (shes a femme fatale)
Shes just a little tease (shes a femme fatale)
See the way she walks
Hear the way she talks

The Call

2006-05-22T20:50:00.000-05:00

I looked at my phone and saw The Gentleman's name. He'd emailed me the day before, saying he wanted to ask my advice on something and he couldn't wait to talk to me.

"Hey!"

"Hey, babe! How are you? Am I calling at a bad time?"

"Nope, what's on your mind?"

He went on to talk about how much he missed me, it had been too long since our last appointment. I agreed, and told him I was glad we'd be seeing each other The next day.

"Yeah, me, too. I guess it's not as hard for you to wait...I guess it's simpler for you, you know what i mean?"

Oh, great.

"I'm not sure what you mean."

In the next ten minutes he spoke and said nothing; how he has these feelings for me and inserting, 'oh, you know' at the end of every sentence fragment. He was not telling me everything and I was getting more and more impatient.

"Do you want to see me tomorrow?"

"God, yes! Of course I do!"

Another several minutes of saying nothing and I couldn't see the point of this conversation.

"Baby, I really need to go. Am I seeing you tomorrow?"

Then, like someone was holding a knife to his throat, he blurted,

"....I can't afford it!"

So there it was. Fucking twenty minutes on the phone and I now had a very big problem.

"You should have told me this at the beginning."

"I didn't want to hurt your feelings."

"This is not about feelings. This is a business arrangement. I am not your wife or girlfriend. You don't get to worry about hurting my feelings. You do need to worry about being disrespectful of my time. I understand that these things happen, income fluctuates, schedules get messed up, whatever. But I take our appointments seriously, and I don't think you do."

He was weak in his responses, self-pitying and truthfully, I wanted to punch him.

I ended the phone call, totally pissed and really worried about how I'd pay my bills.

Anybody know any nice, respectful, dependable guys?

Off

2006-05-05T13:13:00.000-05:00

He walked over to me and pulled me up so I was standing in front of him. I was in a bad mood. I was really anxious about my finances because things weren’t going so well at my job, and while I usually look forward to our meetings, the only reason I was there on that day was that I needed the money.

That’s not a good feeling, by the way.

I guess if I had a better whore persona I’d have known how to mask my surliness without seeming fake. I’m not sure how that works; I am not very good at pretending to be enthusiastic about something when I’m really not. I figured the best thing to do was just to tell The Gentleman that I was having an off day.

“I’m sorry, baby,” I began, “but I’m just not feeling very sexy.”

“Cara, you look so great…you’re incredibly sexy.”

“Thank you, I'm just in a funky mood.”

“What’s troubling you?”

“I really don’t want to talk about it; it’s just stuff. I was looking forward to seeing you, and now I can’t get this other stuff out of my mind. Maybe I can give you a backrub?”

“Why don’t you let me give you a massage,” he said.

“Really?”

“I’d love it. Let me help you undress.”

I laid down across the bed and he sat next to me and massaged my back and shoulders. It felt nice, and I closed my eyes. I didn’t want to talk. Soon his hands were on my ass, massaging and sneaking down between my legs and forward to my pussy. I think he’s maybe got some short term memory issues because every time he fingers my pussy I wind up reminding him where my clitoris is and that making little circles at the lower point of my vaginal opening is not very pleasant. It’s actually pretty annoying.

Once I guided his fingers to the right spot I tried to get into it, knowing that if I came I would feel so much better about everything, but my body was not having any of that. After a while I raised my hips and rolled onto my side, signaling for him to stop. I took his hand, saying, “I’m sorry, I just don’t think it’s happening right now. I need a break.”

He laid down on the bed next to me and we talked. There were basketball games on the TV, but the sound was off.

“Cara, is there…”

“What?”

“Oh, nothing.”

“What?!”

“I was just wondering if there’s anyone you’re interested in being with, like, a boyfriend.”

Oh, fuck. This again. No way am I telling him about my personal life. It doesn’t matter and he shouldn’t ask. Ours is a business relationship, ideally free of those kinds of concerns. Why doesn’t he understand that? Why can’t he respect that?

“We don’t have that conversation, remember? It’s counterproductive to our purpose.”

“I know, I know, I just keep thinking that you should have a boyfriend since you’re so young, but you’re also probably too busy to have one, aren’t you?”

Again with the personal assumptions. I have to say I’ve gotten pretty good at circumnavigating the questions in my responses,

“My life is just the way I like it.”

“Do you want to suck my cock?”

“No. Hand me the lube.”

He gave me the bottle of Pink lubricant he’d bought for me a few weeks earlier. I squirted a couple times into my hand. His cock was hard; he’d been touching himself as we talked.

By this time, I know just how to stroke The Gentleman’s cock, I’ve watched him do it so often. I make a tight tube with my hand and use my thumb to spread his precum over the head, sliding down the shaft. The stroking is with the flats of my fingers and thumb in an up and down and slightly circular motion.

I don’t think he’s ever jerked off using lube, because he is going crazy about how good it feels and I’m just sort of mesmerized by the sight of his dick throbbing under my fingers. When his breath gets quick and his cock seizes and he’s about to blow I close my fist around it and stroke just the tip with my thumb and forefinger, milking it.

He shoots, which is unusual. He’s a dribbler, not a shooter.

(I just impressed myself with NBA Playoff metaphors.)

Anyway, the thing is that it may not have been the smartest thing to let myself be vulnerable with him during our appointment, but it felt better than putting on an act that everything was just great, he was so hot and my mouth couldn't wait to have a big helping of his cock.

I guess that's the drawback of regular clients for escorts. Most of the time it's nice because you know what to expect and you become comfortable together sexually. You even come to care about each other in a certain way. You just need to be able to stay within the boundaries of your defined relationship.

Time On My Side

2006-03-16T21:36:00.000-06:00

Friday morning came and I scowled.

An 11:00 meeting meant that I wouldn't have time to go to the gym and come back home to shower. Briefly I considered showering and dressing at the gym but the thought of putting on thigh highs in the locker room was too strange and, I thought, obvious. I decided to skip the workout altogether. Then I got pissed.

Why should I skip my workout? I've bent over backwards for this guy and now I'm denying myself something I love just because I have a time issue? No way. I made sure to work out extra hard, threw my duffel into the car and set off for the hotel.

As I entered the room and he took my coat I told him I'd come directly from the gym and was going to shower. He watched as I peeled off my pants and sportsbra, commenting on the muscles in my legs. I essentially ignored him. He busied himself with the nylon bed restraints while I took a nice long shower.

As I dried myself he peeked into the bathroom.

"Why didn't you come join me?"

"Oh! I didn't think of that! You should have invited me!"

"Well, it's too late now," I said, rubbing lotion into my breasts nonchalantly, enjoying the way he looked as I did.

The ignoring worked; he walked over to me and wrapped his arms around me from behind and looked at us in the bathroom mirror.

"I'm sorry I made you angry. Please forgive me."

I looked at him and sighed.

"Please don't do it again."

"Would you like something? A drink, maybe?"

"Yes, a bourbon would be nice."

He got on the phone and called room service, which didn't serve alcohol before 5 PM. He put on his coat and said he'd go out for some; which brand do I prefer?

"Maker's Mark. It'll be near the top shelf. Just look for the red wax on the bottle."

The Gentleman doesn't drink.

He left and I checked the cash in the envelope. I walked around the room, still naked, and took a seat in the desk chair. I pushed myself off the desk and spun around.

When The Gentleman returned I was still naked, sitting in the chair. He wore a huge grin.

"Look at you! I like it!"

"Pour me a drink and come here."

He did as instructed and stood in front of me. I sipped my drink.

"Take off your clothes."

When he was naked I commented on the state of his cock: fully erect and rock-hard.

"I'm wearing my cock ring! I love it!"

"You've been wearing it for how long?"

"I put it on when I got here. I love how hard it makes me."

I wrapped the cuffs around his wrists and ankles and told him to get on his hands and knees on the bed. I fastened the straps and put a blindfold over his eyes.

I left him there as I took out supplies.

A short time later I was spanking his ass with my hands, and then with the flogger. I was very calm and rather indifferent about it, which surprised me. I thought I'd maybe be angrier about his behavior in the last several weeks, but a switch seemed to have been flipped as soon as he was tied up and my cool was kept.

I stopped every so often and massaged his balls, telling him he'd done well to continue shaving them.

"Touch my cock, please," he begged.

The sheet beneath his pelvis was wet, his ringed cock dripping precum like crazy.

"No."

I got off the bed and went to the dresser. His head turned and followed the sound. I swirled the ice in my drink and reached for a cigarette and his Zippo.

I flicked the lighter open: 'flink!'

His breathing quickened.

I snapped the wheel: 'flttth!'

His ass squirmed.

I lit the cigarette and walked toward him, lighter still flaming. I sat on the bed, holding it close to his face and closed it: 'clink!'

He moaned.

I held the cigarette for him as he blindly dragged on it, ass writhing, hands and feet bound to the mattress.

I took another drink and drag, then extinguished the smoke. I stood and pulled out a condom, sliding it over a smallish vibrating dildo. I put the dildo into my harness and pulled the straps tight. I put on a glove, lubing it, his ass and the dong.

With my ungloved hand I scored his back with my nails as the fingers of my gloved hand massaged his anus. He sighed and pushed back.

I pressed the head of the dildo into his hole and turned on the vibe, touching him lightly on his back, shoulders and legs. His breathing was crazy and I added more lube and began to fuck him hard.

That was when it hit me. I was extremely pissed off and it felt good to fuck him.

That sounded pretty close to rape: fueled by anger. I slowed and buried my cock deep in his ass.

"I am going to release your wrist and I want you to jerk yourself while I fuck you. Your cock is the only thing I want you to touch. Do you understand?"

He nodded and grabbed hold as soon as I freed his hand. He started jerking his dick. I grabbed his hips and drove my cock into him, the dull 'thud' of my harness-covered pubis hitting his ass with each volley.

His breathing sped up and became shallow. He was very close. I gave him one final pump, keeping the dildo deep inside as he moaned and came on his belly and hand.

I washed up, and handed him a cloth.

Our three hours were up.

I dressed and drove home, feeling moderately better.

I wondered if he'd ever want to see me again.

Sounds Like a Winner

2006-02-11T05:16:00.000-06:00

I’ll be the first to admit it.

I was extremely annoyed with the Gentleman.

We hadn’t seen each other in a month. He had called to cancel our last appointment with a voicemail which sounded harried and urgent. He said something was going on and he couldn’t talk about it. I wondered if someone—a parent, maybe—had died.

The following weekend he emailed, wondering when he could call me. Sunday night he phoned. He’d had a very big health scare, but later found out that it was nothing serious. I expressed relief and scolded him for not getting regular check-ups.

He was very chatty, and I had time. We talked for about 30 minutes and set a time to meet for the coming Friday. The Gentleman, in his hangdog way said he didn’t suppose we could spend the whole afternoon together, could we?

“I would need to leave by 2, but we could meet as early as you’d like.”

“I would like to have a lot of time together, but the earliest I could meet would be 11.”

He checked out his work schedule and hotel reservations, emailing me on Wednesday. We could have the room from 11 on Friday; does that still work? We can figure out the $ to suit [me].

I replied that 11 would be perfect, he should figure the “$” at three hours and that I was looking forward to it.

Right then I was a little put off. I shouldn’t have to tell him what my time costs, it should be understood and once the initial agreement is made and never discussed.

He phoned Thursday evening. I guess he didn’t read my email, because he asked about money. I replied that we were scheduling a meeting for three hours. He hesitated at the figure, saying it was a lot of money.

“It’s a lot of time.”

“I guess I was hoping you’d give me a discount for that much time.”

“Listen, if we were going to be spending more than several hours together, or a weekend, that would require special negotiations. Three hours is three hours.”

“Maybe we should just meet for the normal amount of time, then.”

“Which is what?”

“Ninety minutes… I don’t know… What do you think?”

I could not believe this. I took a breath and counted to ten.

“What I think is that you should fully consider what you say before you speak. If you can’t afford three hours then please don’t suggest we meet for that long. We agreed to a day and time, I cleared my schedule for you, which really is about six hours including my travel and preparation time.

What I think is that you should realize that I don’t take our arrangement for granted. I am happy we can get together and I take great care in making sure I look and smell and taste nice for you. I enjoy planning our dates because I want you to have an amazing time.

When you call the night before, uncertain if you can afford it, that tells me you cannot afford to respect me or my time, and that is unacceptable to me.”

“I’m sorry. Are you mad at me?”

“I am frustrated with this situation and disappointed that I made plans which are now uncertain. You have cancelled appointments in the past and I have continued to see you, because I enjoy our time together. You have exceeded our ninety-minute time limit on several occasions and said you felt badly but have made no effort to compensate me for the extra time. That is my own fault, and something about which I should have been very clear from the beginning.”

“Well, now I’ve ruined it for you, haven’t I?” said Eeyore.

I sighed.

“Cara, I’m sorry. Can we meet as we originally planned?”

“I’ve lost track; what was the original plan?”

“Three hours. From 11 til 2.”

“Yes. And this is really the last time I want to have this conversation.”

“You’re right; you’re so much better at this than I am.”

“I’ll see you tomorrow; goodnight.”

I know that other escorts and sex workers will probably say I am being too nice and should cut him off. If I had other sex clients I probably would. But I don’t. And the prospect of making my rent in one day was a hard one to ignore.

Sex Blogs, Sex Work, Escorts, Sugardaddy, Whores

Conduct Unbecoming

2006-01-06T12:46:00.000-06:00

He held me at arms’ length, running his hands down my sweater sleeves and up again.

“It’s been so long!”

“It’s been two weeks.”

“That’s too long!”

I didn’t respond, just smiled and unpacked my bag. It was, after all, his decision that we meet less frequently and for less time. The past two meetings had gone over on time and I was determined to not let this one go the same way.

“Have you had sex since the last time we met, Cara?”

Was he kidding?

“I’m not going to discuss that with you! You should know I never kiss and tell…You shouldn’t ask such questions!” I said, trying to make light of the situation.

“I know; you’re right. I guess I wouldn’t want to know the answer…I’d probably be jealous.”

Outwardly, I smiled and shook my head slowly from side to side as I laid out toys and lube.

Inside I was incensed. The man pays me to have sex with him and he wants to be the only person I’m fucking?

Driving over today I was ready for action. I kept squeezing my thighs together as I drove, thinking that I was so ready to come.

Last time The Gentleman had discovered how very much he liked watching me suck his cock. It is a very manageable cock: just big enough to hit the back of my throat if I take it deep, but not so large as to trouble my gag reflex, let alone try to pass over it. There was, however, a problem with the cock.

The Gentleman was rather unkempt in his nether regions.

His pubic hair is not terribly thick, and is light in color. But it is long and fairly straight.

If I had to choose, I would choose a man with hair over one without. The sight of a completely bald pubis on a man is not so attractive to me. Some like it shaved, others like it untouched, I fall somewhere in the middle. Returning home I’d thought that I’d like to shave his cock and balls sometime. In my rush to leave the house I’d forgotten to pack shaving supplies.

“You know what I thought we could do today?”

I shook my head, “No, what would you like to do?”

He lowered his voice to a conspiratorial whisper, “I thought you might like to shave my cock!”

Well, praise the lord and pass the ammunition.

“Really?? You want me to shave you? Any reason?”

“Well, not everything, but I thought maybe just the shaft, so you won’t have to pick hair out of your throat like last time.”

This might not be so bad after all.

“You know, I think that is very hot. I would love to shave you. I had the same thought, but I didn’t bring anything with me.”

He smiled and walked to his bag, producing a disposable razor and shaving cream.

“That is great! Look at you! But, it would be better to trim the hair first, before we shave.”

He pulled a pair of scissors from the bag.

“Wow. Nice work. Got a comb?”

“No…”

“No worries; I can make do.”

“I want to make you come first, then maybe you could suck my cock and then you can shave me.”

Nuh-uh.
I was annoyed at his earlier question and determined to run this show. I would shave him first.

We walked into the bathroom and he sat on the stool. I went to work, pulling up long tufts of hair and clipping them close. I trimmed all of his hair, dropping the clippings to the towel I’d spread on the floor. I ran the hot water and wrung out a washcloth. I laid it on his cock and balls.

I filled a glass with water and set it on the floor beside me. He was hard as I spread the foam on the shaft of his cock, around the base and down to his balls. As I started to shave, crouched in front of him in my t-shirt and panties, he exclaimed, “Wow, you really know what you’re doing.”

I looked up at him, hard and naked except for his socks. One foot was on the edge of the tub, the other propped up on the counter. No way was I going to tell him this was the first time I’d ever shaved a cock.

I finished the front and had him bend over the tub, saying that if you shave your cock and balls, you should throw your ass into the mix as well.

He was smooth then, and I told him to rinse off and clean up the hair on the floor while I went to get a drink.

I took off my t-shirt and stood in a raspberry colored satin bra and panties, lifting a glass to my lips when he walked out of the bathroom. He sighed, “Oh, that looks so nice.”

“You like it? I’ll show you my favorite part,” I said, turning my ass to him. There was a small keyhole at the top of the panties, tied with a bow.

“Did you wear that for me?”

“Of course.”

“Oh, I want to make those panties wet.”

He sat on the bed, stroking my skin and the satin with his fingers. His lips went to my cleavage and I unhooked the bra, my eyes on the clock. We had forty minutes left.

He sucked my nipples, pulling them stiff and gently rubbed my clit through the fabric. No surprise, I was already wet.

“You’re so wet, babe,” he said, looking up at me, eyes concentrating, “I want you to come on my fingers. I want to make you come.”

I stood there, straddling his fingers, thinking how I didn’t like being called ‘babe’ by the Gentleman. It’s not the word itself, I think it’s the context. I think he calls me that because he doesn’t know what else to call me. It sounds unnatural from his lips. The lips which had formed the question earlier that pissed me off.

But I was standing tall, and he had subordinated himself to my razor-wielding hand and now to my juiced pussy. I looked down at him, said nothing and handed him the vibrator.

As he passed it over my clit, I started. I took it from his hand and moved the dial back to low.

“Start slowly.”

“Oh, okay. How’s this?”

“Mmmm, that’s it.”

I guided him, stopping at the good spots and pressing up with my hand on his; pressing down with my hips. I came, juicing the panties. The scent of my sex was floating up to my face. I got naked.

I took control of the vibe while his fingers stroked my pussy, rubbing the wetness in. He put a finger in and started moving it around. This was distracting, especially as I was focusing on my clit.

“Use more fingers. Two. Three. Stay on my g-spot,” I crooked my fingers in a “come here” motion (I do this every time we are together), “like this…”

He got it. And then he got it. I gushed into his hand and, exhaling through my nose, suppressed a loud moan. He withdrew his fingers, creamy and glistening.

“Come lie on the bed.”

He had stretched the nylon spiderweb over the mattress and handed me the cuffs. I strapped them to my wrists and ankles and he fastened them down. He clamped my nipples and knelt over my face.

“Do you want to suck my cock?”

Oh, please. This is how you speak to a submissive?

“No.” (Now what are you going to do? Huh?)

He moved between my legs and started licking my pussy. That's it? Unbelievable.

He sucked on my clit and I moved my hips upward. My nipples smarted as he pulled down on the chain and one broke free. He released my wrists so I could re-clamp it. Thusly freed, I reached to the table for the vibrator. I took it in both hands and ground it into my clit as he sat back with his fingers inside me.

I needed to come so badly. Had I been home alone, I would have done the same thing. He was there, but didn’t really add to the experience.

A couple growling orgasms later I looked at the clock. Five minutes.

I looked at the cock.

I unfastened the ankle cuffs, “I want you to fuck me.”

He put on a condom and I flipped to all fours. He slipped inside my pussy and started fucking me softly. I pushed back hard. His hand tapped my ass.

I took my own hand and smacked my asscheek hard.

“Like that.”

He tried, but no dice. He pulled out and sat on his heels.

“Sorry, I’m not hard enough.”

I looked at his sheathed cock and took it in my mouth, sucking on it hard. It stayed semi-hard, flopping over to the side.

“Honey, I really need to get going…”

“Go,” he said, pulling off the condom and throwing it to the wastebasket. This was the first time I’d seen him express an emotion. He was frustrated and I wondered if he was upset with me.

“Are you mad?”

“God, no! I just, well, I really wanted to come twice today, and I haven’t even come once!”

(Bear in mind, dear readers, that The Gentleman has NEVER ejaculated twice, let alone twice in 90 minutes. He expressed this as a goal several meetings ago. I suggested he start wanking a lot.)

“You know, I wanted to come so bad while you were shaving me…but that wouldn’t have been very hot, would it?”

“Why not? I think it’s incredibly hot. You really shouldn’t hold back on your orgasms, especially if you want to have more than one. I’m not sure how realistic a goal that is, considering our limited timeframe, though. Just relax and enjoy yourself. If you spend all your time thinking about your orgasm you won’t have any fun. And that is what this is about, right?”

“Yeah, I guess…it’s just so frustrating.”

“Listen, if we had four hours together it would be a different circumstance. We don’t have that much time when we meet, so I think it’s counterproductive to dwell on what isn’t working. Let’s just focus on having a good time.”

“You are so much better at this than I am. I guess because it is all business to you, isn’t it?”

Here we go again.

“I’ve told you; this is a business arrangement which gives me pleasure. I was looking forward to seeing you today, and I was desperately horny.”

“I wish we could see more of each other. And I feel badly that the last few times we’ve met, you’ve been shortchanged.”

“Yes, well, you're a smart businessman. You know how to remedy that.”

He said nothing.

Driving home, I decided that this was enough. If he won’t take responsibility for compensating me for extra time, this will not continue. Ninety minutes is nothing. Two hours was about perfect. And it’s not a big deal if we go over by 10 or 15 minutes. But after that it begins to be disrespectful of my time. Not only because I’m not getting paid for the extra time, but because I also have a life.

I have a very busy life, in fact. The Gentleman’s behavior today made me feel like a whore. Not in the good way. I drafted an email.

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Merry Christmas, Bitch

2005-12-24T10:58:00.000-06:00

“Goddammit!”

I hung up the phone and merged back into traffic. The Gentleman had just called to reschedule our date for Friday. Apparently his company was planning to let several people go (Why not just say ‘fire?’ ‘can?’ ‘sack??’ I hate the term “letting go,” so self-serving in its design to assuage guilt.)

Forgive me, dear readers. Ahem:

Apparently they were planning to sack several employees on Friday, just over a week before Christmas. Very nice, I thought. I have even fewer qualms about taking money from him. Not that he’s a bad person, but that, as a cog in the corporate wheel, he’s lost any professional autonomy he might ever have had. He’s the one who fires people on December 17 when they’re counting on holiday bonuses. I kind of hate him a little bit.

Because of the HR work which must be done, The Gentleman wanted to reschedule our date for the following Wednesday, four days before Christmas. Naturally, I was expecting a nice holiday bonus as well, and expecting it earlier than then. I agreed to the date, saying I hoped nothing else came up, it being so close to the holiday weekend. I also knew there would be a good chance that I’d have my period, but I wasn’t going to say anything on that subject.

I arrived at the hotel, parked the car outside the rear entrance and finished my phone conversation. The Gentleman met me at the door and looked genuinely happy to see me.

I’d been psyching myself up for this; I was in no mood to be sexy. First, my period did arrive the day before, and I was not going to be exposing my pussy to him. If our regular date had fallen during the week of my period I would have told him ahead of time and rescheduled. But he called me with less than 24 hours notice and cancelled our date. So, in my estimation, he is damn lucky to get whatever he gets.

Secondly, my personal life was causing me grief. I'd had a fight with the guy I'm seeing. I was distracted, lonely and mildly depressed by it. I didn’t want to have to be “On.”

But I switched it on. I reasoned that it might be just what I needed—a good, swift kick in the ass to jar me back to myself.

We walked into the room and I started unpacking as he came up behind me and ran his hands across my shoulders and ass, kissing my neck.

“I missed you. It’s been such a long time.”

“I know. How was your day on Friday?”

“It was awful. I hate doing that, especially before the holidays. But I’m not sure which is worse: firing people before or after the holidays. It’s hard either way."

I nodded in agreement as he said, “But I am so GLAD to see you!” He buried his face in my neck and I pulled back.

“It’s really a shame you cancelled our date last Friday, because you know what?”

He looked at me quizzically.

“Today my panties are not coming off.”

“No??”

“No.”

Let him think i am punishing him for cancelling on short notice. Maybe my time will be better respected in the future.

I stripped down to the ensemble he’d given me last time. I left my black knee-high boots on. They looked awesome with the stockings, garter belt, g-string and push-up bra. Cara was back: coy, sexy, flirty me.

“Oh, my god, you look so gorgeous.”

“Well, you have very good taste!”

I started pulling out toys, leaving the pièce de résistance: a strap-on dildo harness. I was a little wary of how he might react to that, even though he’s given his ass to my vibrators and butt plugs and fingers.

After I’d selected the playthings, we started kissing. I don’t know if he’ll ever be a good kisser, let alone great. It’s like he is embarrassed and unsure every single time we kiss, despite my best efforts at instruction.

I want to slap him. I want to humiliate him. I don’t.

His fingers slide the cup of my bra down, exposing a nipple. He licks it and then sucks. I can’t even feel it. I am standing between his legs as he sits on the bed. I lean my chest forward to his mouth and slide my knee up to his crotch. I kneel down and suck his semi-hard cock until he is about to come. I push him onto the bed and blindfold him. Not so he won’t be able to see; I don’t care if he watches me, and the scarf is very sheer. He could look at me if he wanted to; I realize now that it’s more so I don’t have to look at him, so I don’t have to answer the questions in his eyes.

I move to kiss his nipples, tracing each one with my tongue and gently biting. I slide a clamp onto each and lube his ass while he plays with himself. I cover an egg vibrator in a condom and push it into his hole. As I turn on the vibe he moans.

“Oh, I like this so much.”

“I’m glad.”

I use another mini vibrator to tease his nipples and the head of his cock. His hands move to my panties. I pull away. I sit next to him and give him my tits. As he softly sucks, I turn up the vibe in his ass. Finally his sucking is harder and faster. Finally I am enjoying myself.

“Cara,” he asks breathlessly, “do you think you might be able to use a vibrator in my ass? I think I might be ready to be fucked.”

Now a grin came to my lips. I couldn’t help it.

“Baby, if you want to get fucked, I can do better than a vibrator. Stay right there.”

I walked to the bag and pulled out the strap-on. Once I had it in position I told him to uncover his eyes. He pushed the scarf up to his forehead.

“Would you like me to fuck you with my cock?”

“Oh, my god…why am I so turned on by that?”

“Don’t ask questions, just tell me. Yes or no?”

“Yes!”

“Very well. I want you to roll onto your stomach, bend your knees and spread them as wide as you can. Your chest to the mattress, your ass in the air.”

He did as instructed and I slowly removed the egg from his ass. I wrapped it in a towel and squirted lube into his crack.

“Lube yourself. Inside and out.”

I put on a glove and lubed the fingers.

“Don’t be nervous, it’s just my fingers. We’ve done this before. Deep breaths and push down a little bit…there. How are you?”

“Good,” his voice was quiet.

I put another finger beside the first, checking the angle of penetration, the slight jog to the right that his rectum takes after the first couple centimeters. I moved the fingers in, out and around, massaging and relaxing the muscle ring to accept the size of my dildo.

With my two fingers in, after several minutes I placed the head of my condom-covered cock at the entrance. Slowly pulling my fingers out, I replaced them with the dildo, easing in, curving right. He tensed, and his breathing changed. I stopped, holding position.

“Take a deep breath and tell me how you feel.”

“Uh, okay…”

“It shouldn’t hurt,” I squirted more lube on the three inches or so of my cock which were outside his ass, and spread it around his hole.

“No, it doesn’t hurt. It’s just…different.”

“Okay, that’s good. I’m going to go very slowly and you tell me if you want me to stop.”

I pressed slowly in, his ass swallowing my cock. I held it there, gently pulsing. He sighed and smiled. I held his hips and started fucking in short thrusts, very slowly, very gently, gradually increasing speed.

“I can’t believe I’m doing this,” he said.

“Believe it…enjoy it,” (‘bitch,’ I thought.)

My thrusts became deeper and faster. I was pumping his ass full of my cock and he was enjoying it.

After about five minutes he’d had enough. I pulled out and went to the washroom. I cleaned the toys, wrapped the condoms and glove in toilet paper and tossed them into the trash, rolled the soiled towel up and put it on the floor under the sink.

When I returned, he was lying on his back, smoking, still wearing the nipple clamps and the scarf pushed up to his forehead. He looked ridiculous.

“Hey, babe. I thought I lost you in there!”

“No, but good sex etiquette demands clean toys and a tidy hotel room,” I said, as I removed the nipple clamps. He sucked his breath as the circulation returned to his nipples.

“I really wanted to cum, but I lost my erection while you were fucking me…I still can’t believe I took it up the ass!”

“Hah! You took it like a MAN!”

I looked at the clock and saw a little time remaining. I took his soft cock in my mouth and sucked him off. He came in my hand.

As I dressed he wondered if we could meet during the week between Christmas and New Years. I told him it would be a pleasure. But I wasn’t betting on it.

Back home I continued the conversation I was having when I arrived at the hotel.

-Well, how was it?
-Bearable. I fucked him with my strap-on and called him my bitch.
-Wow, congratulations on crossing that threshold!
-I know, but somehow I don’t feel any better.
-Odd; fucking ass for cash always seems to make me feel better.
-I’m just in a funk. Everything that’s going on with the boy, you know?
-Yeah, sweetie, I know. Anything I can do?
-Nope, you’re awesome. I love you.
-I love you, too. You’re totally awesome. And boys are stupid.

It’s good to have friends.

Happy Holidays, Bitches.

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Whore Persona

2005-12-17T22:19:00.000-06:00

Nearly six weeks since our last meeting, The Gentleman called with some mildly disturbing news.

He’d gone to the doctor after weeks of stomach distress, and called me with the conclusion that he had to make some changes in his life. Seems he was stressed and his tummy wasn’t cooperating. The call came as I was making my rounds at Whole Foods one afternoon.

“Hey, baby. What did the doctor say?”

“He said that I needed to reduce the stress in my life”

“What does that mean?”

“There are a lot of things that are weighing on me financially…my business and other burdens are putting me under a lot of stress. And I've been thinking about you a lot. I really miss you.”

“Well, we should try and fix that!”

“I just don’t know how feasible it is for me to keep seeing you when I have to put some of my own finances into this business…I guess it’s not realistic to expect to see you without some payment taking place…”

“Oh, baby…that’s what this is about?”

“I just don’t know how I can afford a weekly date with you and still meet my obligations to my company.”

“Listen, you need to take care of your health. That’s the most important thing. And if it’s too much for you financially right now, that’s fine. You just call me when things have calmed down, okay?”

He hesitantly agreed, and I ended our conversation, saying he didn’t need to worry, that I was fine, and that I hoped to hear from him soon. I think he would have stayed on the line indefinitely if I hadn’t hung up.

I got to thinking: Maybe our weekly arrangement was a bit much. What if we only met once or twice a month? Obviously, something would be better than nothing, and our dates had afforded me some luxuries I hadn’t had before. He definitely needed the outlet, and I was having so much fun…

He was not going to make the first move; I knew from our sessions that he was not exactly forthcoming in his opinions. I decided to email him.

Hi, G.

I've been thinking about our phone conversation yesterday and I've been a little troubled by it. Obviously, you have to do what's best for you. If it's not feasible for you to continue getting together I understand. But I don't want you to feel like our original agreement is set in stone.

I do enjoy being with you. I want to be as flexible as I can be for you. Perhaps you'd like to consider whether a different arrangement (less often, or for less time, or both) makes any sense.

This has been fun for me; planning our dates, introducing you to new experiences, learning what excites you. I wonder if it could possibly continue, with an adjustment of terms. There are lots of changes which could be made to make it a bit easier on you financially, and (if your doctor is to be believed) alleviate some of that stress while releasing tension!

I guess what I'm saying is, think about it. And be honest. Write me back and tell me what you think. If 60 or 90 minutes sounds better than two hours, if twice a month sounds better than once a week, whatever.

As I said on the phone, I am disappointed by this, but I understand. I just know how frustrating it can be to come so close to something, only to have it pulled out from under you. I felt like we were moving things up a level sexually, and it's sad to have that end so abruptly.

Whatever you decide let me know.

Have a good weekend,
Cara

So he responded. And we set a lunch date to discuss new terms. Of course, he called two days before our date.

We agreed on a restaurant, the one we'd met at before. We discussed financial arrangements and thought that twice a month for 90 minutes might be something to try.

I was happy he’d come around. I thought it was silly to stop things just when they were getting good, and I had the feeling he really wanted to continue but was unsure how to approach me about it.

He was very excited and happy that I had come back with alternate suggestions. He probably would not have done it, even though he had thought about it.

“Well, I am nothing if not straightforward,” I said.

He asked if there were supplies he should bring. I reminded him that last time he broke my favorite vibrator. He wrote down the model and then asked for my bra size.

“34 D or DD, depending…what are you planning to do??”

“I thought that maybe you’d like to wear some lingerie for me if I brought it.”

“Oh! I’d like that very much!”

The next day we met for lunch. I ordered a vodka tonic and didn’t pay attention to the price of my lunch. I figured that if I was going to be getting paid less in cash, I should order whatever I wanted.

In the room, I took off my shoes and coat and laid my handbag on the floor. I put my toybag on the dresser. There was a huge gift bag on the bed which I pretended not to see. We kissed and he took my hand and led me over to the bed.

“Oh, my goodness…what is this?”

“This is your early holiday present, Cara. I hope you like it.”

In the bag were two boxes. I picked up the large one first, naturally. It was a restraint system which consisted of four nylon and Velcro cuffs that could be attached to any point on a spiderweb of nylon straps that are secured to the corners of a mattress. It looked complicated, but when we straightened it out and laid it on top of the bed it looked like it could be fun. The restrained person could be repositioned easily onto their knees or back or tummy simply by refastening the cuff release.

“Okay, I am liking this…does this mean you want to restrain me?”

“If you’d be willing, I’d like to very much. But you still have another gift! You have to open it!”

The smaller box was pink with silver writing. I slid the lid off and peeled back the tissue paper. I gasped. It was so pretty—an entire ensemble of lingerie—bra, panties and garter belt. All black.

“Oh, my god, it’s gorgeous! I love it! Thank you!”

I gave him a kiss and held up the bra to my chest. I looked at the tag. It was the perfect size. This was going to look fabulous.

“But, baby, I didn’t wear stockings; how can I model this for you…I guess with just the bra and panties?”

He grinned and reached into the box, moving the paper to one side. A package of black stockings lay underneath.

"Well, don't you just think of everything?!"

“Oh, you forgot something else, Cara.”

He held the big bag angled toward me and I reached in and felt it: my new vibrator. Yippee!

“Why don’t you go get changed?”

“I’ll do that, while you load this baby up with batteries…’kay, hon?”

I gathered everything into the box and carried it to the bathroom. It took a while; it’s been years since I’ve worn a garter belt and those hold-ups are tricky, especially the back ones.

I walked out and stood in front of him.

“Oh, my god, that’s gorgeous.”

“It is! You did very well! Hey, watch me—I’m walking now…”

I pranced slowly to the other side of the room and turned.

He gulped and came over to put his arms around me. We were standing in front of the small dresser with the mirror. He told me to look at myself. Then he said, “I guess I should probably get undressed, now, huh?”

“You do what you want, baby. All I know is that these stockings are staying on.”

I sat on the bed and watched him undress to his shorts and socks. It is so endearing to me now that he leaves his socks on. I figure if he’s that uptight about his feet, I don’t want to see what’s underneath the Gold Toes.

We sat on the bed and he stroked my legs through the stockings.

He told me I smelled good. He kissed me. My feet were in his lap and he pushed my knees apart and leaned me back toward the pillows. He turned on the vibrator and lightly touched my clit through the panties. I gasped and moved around to get it to the right spot.

I know this vibrator, and I can get off in record time with it.

“Oh, babe, your panties are soaked…”

I guided him with the vibrator, pinching my nipples and sitting up to kiss him once I’d come. I was smiling, thinking how happy I was going to make myself later when I got home with my new replacement.

He unhooked my bra and tossed it to the chair. He helped me off with my panties and held them up to his face.

“It’s nice, huh?”

He nodded and went to the restraints. He asked me to lie down and then struggled to detach the cuffs. I helped him out, telling him where to put the release straps and even wrapping my wrists and one ankle myself.

I told him where to find the buttplug in my bag and asked him to turn up the music. He brought the bag to the bed and rummaged through it.

"Cold Hard B****" by Jet was in rotation on my iPod.

I was spread out on the king-sized bed wearing the garter belt and stockings. He stroked my body down to my pussy, raising my knees and spreading them.

“You have such a pretty pussy, Cara.”

“Mmmm-hmmm…”

“So pretty and pink and wet…”

“Uh-huh…” (Please stop talking about it and do something, would you….)

He dove in, licking around my clit, up and down my slit to my ass. (Now we’re talking…)

The Gentleman takes his time eating pussy. I’ve learned that it is really the reason I’m here. He isn’t as interested in his own orgasms, but loves to give them to me, so I accept it like another gift. He is a willing pupil, thank goodness, because I was directing him the entire time (to the left, up, now put your fingers on my g-spot and move them like this…).

I got off again and he exclaimed about how wet my pussy was again. Then he told me how nice my breasts were and asked if I’d ever tried “those nipple clips.”

I laughed, “Yes, there are some in my bag. Would you like to put them on?”

He jumped and grabbed them. I instructed him on how to pull my nipples up and attach the clamps with the slides. The pain was sharp at first, but yielded to pure sensation. I sighed.

I swear to God, I heard his cock stiffen.

“Can I put the plug in your ass?”

“Yes, just put a condom on it and use plenty of lube.” (God, I wish I didn’t have to talk so much…)

The upside was that he did everything I told him to do. He learned about the ultra-sensitive spot just to the right of my clit that sends me, head thrown back, over the edge with barely a “hello.”

He wanted to fuck me.

(Five dates and I was getting fucked for the first time. Not bad.)

He put on a condom and released my ankles. He fucked me. Pure friction. Two minutes and he was done, shooting into the condom

I don’t mean to sound put off by it; the fucking was fine, it just didn’t get me off. I didn’t really expect it to, but he was blissfully happy, and that’s what we were going for, right?

We’d gone way over on time, but I chalked it up to a nice reunion after so many weeks without a meeting. Plus, those garters proved pretty tricky. All told, I figured he’d spent a good $200 on gifts; add another $50 or so for lunch, and I wasn’t troubled by the extra time.

I gathered up my booty and dressed quickly. He apologized profusely for not paying attention to the clock, since he was the one “in control.”

I laughed to myself that, in between orgasms, there I was, all tied up with a plug in my butt, clamps on my nipples and a dick in my cunt and I was still bossing him around. I guess it’s just my whore persona.

It’s interesting to me that I behave so differently in this situation than in every other sexual relationship I’ve ever had. I am very easygoing, rarely taking charge during sex. I love being forced to suck my boyfriend’s cock while I’m tied up, for example. With The Gentleman, though, I don’t even think along those lines. I am the writer, producer and star in this show. I really, really like it.

I’m already working on the script for this week.

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Blind Man's Bluff

2005-11-03T22:19:00.000-06:00

In the two weeks since we last met, The Gentleman and I have both been a bit under the weather, he more so than I. I was busy with other interests (and interesting parties...but that's another story for another place), and I found myself looking forward to today's meeting.

He phoned two nights ago, asking if we were still on, and if there was anything he could pick up in preparation. I asked him to buy some Eros lube, non-lubricated condoms and a small toy that he thought looked fun. He got very excited at that idea and suggested that he'd look for a certain set of restraints I've been wanting. I wondered if he'd go through with it, as inexperienced as he is in such things. He'd never gone into a sex shop before. I suppose the employees of toy stores are used to people wandering around trying to appear nonchalant as they paw through flavored oils and huge rubber dildos.

I packed my bag and showered. I put on a pair of blue jeans and a black sleeveless sweater and blew my hair dry. I was in the car when he called with the room number.

He pulled me into the room. He'd missed me, had I missed him? He moved in for a kiss. I turned my head to the side, "Baby, I'm sorry, but I'm unable to touch you with my mouth today...I have a cold sore, see?"

He laughed. "Oh, I get those, too. So, it's okay if I kiss you, right?"

"Well, no, I'd prefer if we kept our individual oral herpes strains to ourselves, thanks!"

He was chomping at the bit. He was like a kid with ADHD or something. He couldn't sit still. He kept saying how much he'd been looking forward to today. He was a gentleman and DID let me sit on the couch and have a drink after my drive.

"Cara, what are you thinking?"
"I'm thinking that if I can't use my mouth, there should be something that you can't use..."
"Like what?"
"I think your eyes."

"My eyes? How will I do anything?" he laughed.
"You'll get better at using the rest of your senses. Yes, I think a blindfold is the perfect twist for today. Are you alright with that? You won't be tied down, and you can stop if you need to. How does it sound?"
"That sounds perfect."

He started to put his hand under my sweater. I pushed it away.

"You didn't ask permission to touch me."
"I'm sorry...may I touch you?"
"No, you may not. Take off your clothes over there while I watch."

I sat on the luggage bench by the door and looked at him. He undressed and I told him to lie facedown on the bed. I hadn't brought a blindfold (can you believe it, I don't even own one), but there was one thing I did have: a long piece of black silk rope. I doubled it and wrapped it around his head twice, lashing it in the back and making sure it wouldn't slip. I stopped and looked at my work. It was really hot.

I knew he couldn't see anything, and I moved from place to place in the room, choosing to make one noise, watching him to see what he did. Ice shifted in my glass as I took a drink, the toy bag rustled as I reached in for my flogger.

The Gentleman had expressed interest in light bondage and wanted to know when he could tie me up. As before, my response was that he needed to know what it felt like to be in a submissive position before he'd be ready to put someone else (me) there. I've explained that so much of the thrill is psychological, and that pain doesn't even have to factor in. I wanted him to be deprived of one sense, and to find out how his other senses responded.

He was lying on the bed with his arms folded underneath his cheek. I was still fully dressed. He started talking, which I know is a result of feeling nervous and excited.

"What are you going to do to me, Cara? I'm going crazy that I can't see you! Where are you?"

"First, sir, just try and relax. You need to trust me. I am not leaving the room. This is not about me torturing you. This is about you experiencing something new and exciting. I am going to help you get in touch with your senses. You will not see me, but you will hear, smell, feel and taste me when I think you are ready. Right now, just feel the pressure across your eyes. Feel how the ropes press onto the bridge of your nose."

"I like it. It's soft."

"Good. Now, unless I ask you a question, or you are ready for me to stop, I don't want you to talk. I just want you to pay attention to your senses. Understand? Stop trying to analyze everything. Try to give yourself over to absolute pleasure." (Okay, I didn't really say that, but it's not every day a girl gets to use a Rocky Horror line in her blog!)

I walked over to the bed with the flogger in my hand. It is a small leather flogger which is very soft and makes a good "whap!" on the skin. I held it above his foot and lightly moved it up his leg.

"Oh, mmmmm..... are those your panties?"

I didn't reply. I just kept tickling his feet, legs and back with the soft strips. After several minutes, I flicked my wrist and let the tails spread out between his shoulders. I dragged the flogger down to his ass, then twirling it so the straps were like car wash brushes along his back.

"Turn over now, please."

He rolled onto his back and I continued with the flogger on his legs, arms, chest, face and cock. Just swirling. Just teasing. I moved down to his feet and stood on the floor in front of them. I pulled back with my wrist and slapped the soles of his feet just hard enough to convey that, no, this was not my underwear.

"Hold out your hand."

I placed the handle into his hand and told him to touch it. He took it in both hands and let out a "mmmmm! I like this!"

"Smell it. Drag it across your chest. Slap it into the palm of your hand."

As he did, I took off my sweater and opened up a condom. I put my remote-controlled butt plug inside the condom and picked up the bottle of lube. I set both on the bedside table and reached over to my glass. I took a sip. I picked up The Gentleman's glass and took the flogger from his hands. I sat on the bed, put my arm under his neck and pulled his head up to the rim of the glass. He took a sip, and I replaced the glass on the table.

As I lowered his head to the pillow, I leaned forward. I knew he would be able to smell my skin, a mixture of sandalwood and orange and vanilla. He inhaled deeply, saying I smelled so good. I pulled back, disappointed that he'd spoken. I told him this and went to sit on the couch. I looked at the Conde Nast magazine and lit one of his cigarettes.

Once he was quiet again I went back, letting my fingers graze his crotch. His cock twitched and hardened. He sighed. I wanted him good and hard. I moved up beside him again and turned my back to him. I took his hand and placed it between my shoulder blades. He moved it down, stopping at my bra strap.

"Unhook it."

He did, and used both hands to trace my spine down to my jeans. I reached back and felt for his dick. It was hard and soaking his boxers with precum. I stood, turned and helped him off with the boxers. Finally his dick was free and he touched himself, spreading the precum over the shaft, stroking it slowly. I lubed my hand a little and got in a few good strokes there. His hips were moving and he was very, very quiet. I slipped a finger back and pressed it flat against his hole. He gasped.

"Keep jerking yourself."

A little more lube and I'd gotten my middle finger in. My ring finger followed and then the plug replaced them. I gave his nuts a squeeze and got off the bed to wash my hands.

In the bathroom I took off my jeans. I walked back slowly so he wouldn't hear. He was touching himself, but not jerking in earnest.

"Do you like the feeling of your ass filled?"
"Yes."
"Touch your nipples. Tell me how it feels."

As he did, I took out my vibrator from the bag.

His breathing was shallow and he reached out his arm, grasping at the air. I walked over to him and took his hand. I straddled his body on the bed and took ahold of his other hand. I lowered my chest so that it was close to his face. He sensed my heat and lifted his head to take my nipple into his mouth. He sucked it softly. I told him to suck it harder. He did better on the other side and I pulled away, just out of his reach. He whimpered.

I moved his hands in close to his shoulders. I lifted one leg at a time and put my knees into his palms, pinning his arms down. I moved myself forward and lowered my pussy onto his face. He started pushing his tongue into me. I slid down a little so that his tongue was on my clit, teling him to lick that. I started circling myself over his tongue, pressing down, getting into a nice place.

I rolled off to the side and laid back, allowing him to move to his knees. He was still blind, and I checked the rope to make sure it hadn't slid from position.

The Gentleman put a finger inside my pussy and said, "God, you are soaking wet." I sighed in agreement and concentrated on getting his fingers up to my G-spot.

"Listen to me. Go slowly and listen to what works. Then keep doing that. "

I had a nice little orgasm and went back to instructing him. I wanted to feel full.

"Use another finger now. Move them around slowly."

With his fingers in me and his mouth on my clit I was on my way to a larger orgasm. After several minutes, he just wasn't getting it, and I was getting impatient. I grabbed my vibrator and put it into his hand. I turned it on and guided it into me, angling it just so. "Mmmm...there we go. Keep it right there and suck on my clit."

In the midst of this latest ride, I remembered that I'd yet to turn on the vibrator in his ass. I looked to my right and found the remote. As I reached the edge of coming, I switched it on. Simultaneously, we moaned. I could feel the sheets, wet from my juice and cool. His cock was rock hard, pressing my thigh as he fucked me with the toy. He was thrusting so intensely that the bottom cap popped off, stopping all my fun.

"What have I done? Why did it stop?"

I looked at the vibe and the cap. It had been twisted too far to the right and had cracked.

"You broke my fucking vibrator. This is my favorite one. "

Oh, I'm sorry...I'll buy you a new one." His voice was tremulous, his dick was rock hard.

"I know you will. Come over here."

I reached down for his cock, intending to wrap it up and sit on it. I wanted a dick in me, and I told him so.

"Do you want me to fuck you, Cara? Or could I jerk off so you can watch?"

I was a little surprised at the response. Why wouldn't he want to fuck? Was he afraid that he'd shoot too soon? Did he think the butt plug would get in the way? Or could it be that, since he was unseeing, his other senses were just overwhelmed and he thought that my pussy holding onto his cock would just be too much?

I sensed that he preferred to jerk off. I told him that was what I wanted. I gave him some lube and laid beside him, cupping his balls as he gave one, two, three strokes and finished the race. Wham, bam.

After, we were lying together and he started playing with my clit again. I held his fingers and told him to relax them and just use them to cover my clit and press gently. I didn't need to come again. I really didn't want to. I glanced at the clock. We had gone over by about ten minutes. I told him to wait right there and I would be back with a towel. I went into the bathroom and turned on the water. As it warmed up, I put on my clothes.

I cleaned the come from his stomach and thighs and turned his head to the side. I untied the rope. He looked at me, all dressed and laughed.

"I love that you're so imaginative, Cara. I never know what to expect, but I'm always happy after we meet."

"I really enjoy this," I said. "it's fun thinking of new ideas for our dates."

"It's so unusual for me to be submissive like this...I liked it! I just, you know, have to be careful that I don't start getting emotional. That I don't let my feelings for you get in the way of this."

I paused. Shit. This is not what I signed on for.

"Listen, baby, that's why we have an arrangement. That's why the envelope you bring disappears when I leave. It keeps things simple. This is about having new experiences and enjoying ourselves."

"I know. I just..."

"What? You can tell me. Maybe I can help."

"Well, sometimes I really need to stop myself from calling you whenever I feel like it. I know, it's stupid. We have an agreement and I need to abide by that. You don't want to talk on the phone."

"What I want to avoid is the feeling that our agreement is shifting on your end. It starts to get complicated. But, baby, if it's hard for you to see me only once a week, by all means, call me and we can set something up to take care of that. I enjoy spending time with you."

"Okay. That's great to know. And I respect your boundaries. It's just that I think you're so great. And you seem to be better at emotional detachment than I am."

"Honey, your emotions are hard to separate from your thoughts and your physical pleasure. The pleasure part is what was missing in your relationship with your lady, right?"

"Yes, oh, so much."

"That's why I'm here. To give you pleasure and to help broaden your horizons. Did you have a good time today?"

"I had a fabulous time!"

"Then I did my job. And remember, this was mostly about you getting enjoyment from your own body. I'm so glad you did."

We set our date for next week. I gathered my supplies, buckled my messenger bag and left.

I think I need to spend time thinking about ways to encourage The Gentleman to introduce affection in his primary relationship. I think that they have been together for so long that it's fallen by the wayside. The fact that menopause has squashed her sex drive shouldn't mean they never touch each other, or show affection in other ways. After all, who wouldn't appreciate a good foot rub in the evening? What woman doesn't like being told that she smells delicious, even if she has zero interest in fucking?

I want to continue with The Gentleman, partly because of the money, but also because I think he is a good man who feels trapped by his own insecurities fed by years of disinterest on his partner's side. It feels good to show him the ins and outs of healthy sexuality: being comfortable with oneself, having a confident attitude and being willing to try new things. He's opening up to the last one. I want to see the rest unfold. I just hope he doesn't fall in love with me or something.

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Crazy Talk

2005-10-27T14:59:00.000-05:00

No meeting this week.

The Gentleman called the night before our scheduled appointment and left a message saying that he'd been sick with the flu. I breathed a sigh of relief, because I was just about to call and cancel myself. Seems that we were both under the weather. Actually, he probably got me sick last week and neither one of us knew. So, next week we should be back at it, and I'll have another lovely romp to write about.

Today I feel like writing about myself. This arrangement seems like it just fell into my lap, and I've been thinking about what it means to me in terms of its continuing.

I truly think that I'm a good thing in The Gentleman's life. He looks forward to our meetings and is always appreciative afterwards with thank-you notes and voicemails. Last week he said something that started me thinking.

As I was getting dressed to leave, we were chatting about the days I don't spend with him. He knows that he is not the only person I have sex with (though, he is the only one who pays me to do it). He said something about trying not to think about me having sex with someone else, even though he knew it was inevitable, and we have a good business relationship that could, one day, change if I wanted it to.

I was really taken aback. Did he not say he wanted no strings, no commitments? Isn't that why I responded to his ad in the first place?

It's a delicate balance. I need to make sure he doesn't start expecting more for less, or start feeling possessive about me sexually. At the same time, he needs to feel cared about and have his needs met physically. I really have no feelings for him other than that he's a decent guy who I get to play with in exchange for the easing of my financial burdens.

I really enjoy our sessions, and being told how great I am, conversationally as well as in bed. I just hope that I can continue with The Great Anticipation: That the six days between our visits will be peppered with smiles and hard-ons for him. That he'll stay awake nights wondering what is in store the next time I'm in front of him.

Myself, I think I can keep it going for a good long while. I'm not in danger of falling for him. I feel affection for the man who is older than my father and has so little sexual experience that everything short of a straight handjob and missionary sex is new to him. Sometimes I worry about that little thing he said, about things changing.

Of course, this was minutes after his first simultaneous blowjob/prostate massage, so we can probably chalk it up to endorphin-induced crazy talk, right?

Bummed

2005-10-20T20:17:00.000-05:00

Today, for our fourth date, The Gentleman was expecting some exta fun. I’d finally let him touch my pussy last week, and when I left him, he was singing the praises of the Almighty G Spot.

I enjoy the familiarity of our encounters: I leave my house, on the way to the hotel, he phones and gives me the room number. I knock, he invites me in, we chat, peppering our conversation with hand squeezes and kisses.

This week I am wearing jeans, a wrap-front top and boots. The sky was turning grey and clouds were rolling in.

I had plans for him this time. As it happens, I can’t have sex today. Luckily, The Gentleman is interested in experiencing more than that. He likes that I have more experience with kink, and am a patient teacher. In that spirit, I have decided to give him assignments to complete for our future meetings. These may be nothing more than to walk into a sex shop and buy a bottle of lube, or they might be more involved; kinkier.

As I am exploring my dominant side I am becoming more comfortable telling him what I would like him to to for me. I think I am becoming quite good at it. As I unpacked my iPod and speakers, I said, “You know, on the drive over, I really noticed how sore my neck and shoulders are. You have no idea how much my feet and legs ache...I would like you to massage them for me.”

His eyes widened, and he smiled broadly, “Oh, yes; I would absolutely love it. Can we start now?”

“Of course.” I moved over and sat on the ottoman in front of his chair. He began rubbing my shoulders and my neck. I leaned back (or, rather, he pulled me back) onto his chest. His hands moved around to cup my breasts through my top. “Does this hurt?

“No, but I need a drink, and the television really shouldn’t be on, now, should it?”

He got up to retrieve my drink and turn off the set. I stood, dropped trou and waited for him to turn around, “I’m ready for my legs now.” I leaned back on the bed and he undressed to his uniform: white t-shirt, blue boxers and black socks.

“Cara, those panties...”
“Aren’t they pretty? I’m glad you like them, because you’ll get to look at them for the next two hours...here’s the massage oil. Start with my feet, please.”

He did, and when the fronts of my legs were done, I flipped onto my tummy. I was still dressed in my camisole and g-string panties. The Gentleman massaged my legs and ass, really getting into the last part.

During the massage my thoughts roamed to things I’ve got to do in preparation for the coming week, how to best deal with my mother’s increasing need for attention in the face of her own mortality, whether the new hair foam I bought is really as good as the company says. And how this is all very pleasant, but will I have time to get to my next meeting? I wonder how the novel I’m reading turns out. How long will it take to finish knitting that scarf I started two months ago?

I catch myself and let my feet roam over to rub his erection through his shorts. The wetness there, the smell of his sex and mine took over my senses. I reached down to my panties and slipped my fingers inside. My breathing was shallow, and as he kneaded my backside, I tickled my front, arching my back and raising my head to kiss him.

“Cara,” he said, breathless, “can we talk about anal?”
“Have you ever fucked a woman’s ass?”
“No, never.”
“Have you ever been fucked in the ass?”
“No, but I’m intrigued by the idea.Why?”

I’d packed a vibrator.

“Well, I am a firm believer that in order to effectively fuck an ass, one should be well acquainted with the sensation of being fucked firsthand. I would be very happy to introduce you. Would you like that?”

“Oh, yes. I think I’d like that very much.”

I walked over to my bag and sat down beside it on the floor. first, I held up a plug. “Now, this is just a bit big for your first time, I think,” he nodded quickly, “that is a little frightening, yes.”

“But this,” I held up a wand vibrator with a bulb on the end for g-spot stimulation, “this would be perfect.”

I sheathed the vibe in a condom and climbed up beside him on the bed with the vial of lube.

He was stroking his cock and had taken off his shorts. I started speaking softly, slowly, explaining that I would start with a small finger, very gently opening him up to larger things. He pulled his legs up and I lubed his arse and my fingers. As I massaged around his hole, I talked about breathing, relaxing. My third finger went in without resistance. I moved around and in, slowly, listening for changes in his breathing.

“Oh, my god, that feels so good...”
“I’m glad, baby. Are you ready for something bigger?”
“Oh, yes...please.”

I took the vibrator in my right hand, placing it against the base of my finger already inside. Slowly, I pulled the finger backwards and pushed the bulb of the toy against him. Immediately, his body took it in. I rotated the wand so that the bulb was angled toward his prostrate, “Is that the right spot, baby?” His head was turned, eyes closed in bliss. He nodded, “yes. Oh, my pet, yes.”

I turned the vibe to LOW. Then I moved his hands away from his cock and started sucking it hard. He was writhing under my head, my lips wrapped around his cock, sucking madly.

My Gentleman moaned, louder than I’d ever heard him, “I’m coming....Cara, I’m coming.”

One last suck up, and I turned up the vibe and started jerking him with my free hand. His come shot, spilling onto his stomach and my hand.

His eyes were wide and amazed, his breathing irregular gulps.

“Baby, are you okay? That was so nice, watching you come.”

“Uhh, I don’t know what to say...that was incredible! I’ve never had an orgasm like that!”

“Isn't it incredible? Let me get you a towel; stay right there.”

He towelled off, and, knowing I had a schedule to keep, prodded me to put myself back together so I would not be late.

We kissed at the door. He was still grinning and shaking his head.

“Next week?”
“Next week.”

While I would not have chosen The Gentleman for myself, given our arrangement, he really is the ideal client for a girl like me. He is open to new experiences, likes that I have had adventurous romps and am not opposed to more, and he is genuinely nice.

This consideration (am I hurting you? Can I do this?) is almost annoying sometimes, because he is so concerned with my comfort and talks--sometimes incessantly--about how great he thinks I am, when I just want to go the other route and have mad, silent, crazy playtime.

Still, he is teachable, he enjoys being submissive, and is respectful of the boundaries I placed on our relationship.

Right, I gave him an assignment: He is to wank at least three times this week, one of those in the shower with a finger in his bum.

Nirvana

2005-10-13T10:29:00.000-05:00

I’d been thinking for the last week about what I’d like to focus on this time. Since his kisses had left a bit to be desired last time, and since I love kisses, I decided that this would be the focus of our session today.

I’d also thought a lot about what my friend, who is a professional escort, had told me: Get used to the compliments, because your clients will pour them onto you. You will feel ridiculous at first, but soon you will realize that they are genuine, and you will learn to accept them gracefully.

I am not a Barbie, a model, or a porn star. I’m pretty, but I have insecurities about my body. I think everyone does.

I am intrigued by the idea that I can let myself be worshipped; interested in the sensation of being in control. I decide that, while I will be teaching The Gentleman how to kiss me, I will be teaching myself how to accept adoring compliments. This will be good for me.

The part I like about our midday hotel meetings is that I can be whomever I please. Today, I showered and walked to my bedroom, where I’d laid all my clothes out. I slid into my black panties and bra, stockings and waist-cincher (Okay, now I looked like a porn star or a fetish model). I stepped into my long black skirt and green blouse, threw on my slingback pumps and was looking very professional.

The Gentleman had told me that he liked black lingerie.

On my way to the hotel, The Gentleman called with the room number, this time on the other side of the hotel, not facing the atrium.

“Okay, I’ve got the number. See you soon!”
“Cara, I can’t wait!”

I’m still getting used to this. Obviously, I want to keep seeing him, and so I need to make him feel like I’m just as excited about seeing him as he is me. Because this is only our second meeting, and he still had no idea how to kiss me or other things, I am still a bit anxious to see him. It’s a new thing for me, sexually, to really put the focus on him. After all, he is the one paying the money for my time. He is the one who ultimately should be satisfied with however our meetings go. But I am still in control. It’s a delicate balance.

“I’m excited to see you, too.”

I knocked, he opened the door, same as before.

I walked in, the door closed, and he wrapped his arms around me.

“You look delicious.”
“Thank you. And you, sir, got your hair cut!”
“You noticed! I was wondering if you would.”

I had brought my iPod and mini speakers. Last time there had been no music and he had talked a lot; probably nerves, but I thought it would be nice to have some background noise. I’d loaded some Electronica: Kruder & Dorfmeister, Zero 7 and Air. Nothing too hardcore.

We sat on the bed, holding hands and talking.

“I thought about you so much while I was away, Cara.”
“You did? Tell me what you thought about.”
“Oh, just lots of things. I got hard several times just thinking about you.”
“I’m glad. I thought about you, too. And I’ve thought about some things I’d like for us to do.”

We were fully clothed, except for my shoes, facing each other on the edge of the bed.

“I want to teach you how to kiss me.”
“Oh, I’d like that. How do you like to be kissed?”
“Try me.”

He leaned toward me, his hands in mine, shaking. Like last time, he kissed my lips hesitantly, very softly, without purpose or intent. We pulled back and he asked, “How was that?”

“That was nice, baby. Now let me tell you how I like to be kissed. I like to feel the strength of your lips when you kiss me. I want you to press into my lips. Pull me into you. Move your lips and tongue around mine. I want you to kiss me like you’re going to swallow me whole.”

He swallowed.

We kissed again, this time I leaned toward him, moving my head, my lips, my tongue. Pressing into him with my face, tugging on his lips with my teeth. I broke away and looked down. His cock was hard, the outline showing through his trousers.

“Cara, can I undress you this time?”
“Yes.”

I stood in the middle of the floor as he unbuttoned my blouse, spreading it apart, holding me at arm’s length, staring at my body. He unzipped my skirt and laid it over the chair. I was down to my nylon and satin, shoulders thrust back, hands clasped behind my back.

I watched him watching me. I prepared myself to be worshipped.

I read last week that Sophia Loren once said that sex appeal is 50% what you’ve got and 50% what people think you’ve got. The Gentleman thought an awful lot of me; he was like a little boy, touching, smiling, blushing. I could feel my confidence increasing. I felt like a superhero.

I sat on the edge of the bed, crossing my legs.

“You look like a photograph sitting there like that…”

He undressed to his socks and boxers. He asked if he should take his v-neck undershirt off; I told him to leave it on, I think undershirts are sexy.

The Gentleman unhooked my bra and asked me to lie back, which I did. He brought the bra up to his nose and inhaled my scent. Then he started rubbing my nylon covered legs and feet, watching me. He commented on my muscular thighs and calves; on my pretty toes, showing pink through my stockings.

Eventually he worked his hands up to my panties—black boyshorts with a notch in the front of the legs right under my hip bone. His fingers moved to cover my pussy, feeling my wetness seeping through the fabric. I could smell myself: that creamy, heavenly scent of a woman who needs to be fucked. Nirvana.

He pushed the fabric aside and took a look at my kitty. My foot was pressing against his cock, which swelled at that moment. He winced.

“God, that is beautiful…”
"Remember what I said about kissing? Do the same thing with my pussy."

He started licking, kissing, rubbing. I guided him with words and by example. I showed him how to rock his head into me, pressing into my clit, pulsing. I taught him to reach up and stroke my G-Spot while sucking on my clitoris until I came. He commented on how beautiful my orgasm was, and then went back for more.

I came again; he was getting the hang of this.

“Cara, what else can I do for you? How else can I please you?”

I had brought a mini ‘zippy’ vibrator—the ones that look like whip-its—and had placed it under the pillow earlier. I reached in and grabbed it.

“You can use this around my clit and kiss my thighs.”

He went to work, but the coordination of both tasks proved to be too difficult. He handed the vibe back to me, and I took it. For my third orgasm of the day my back arched, feet on his shoulders, saying, “Fuck me with your fingers…harder;” I grabbed his head and pushed myself onto it, releasing into the satisfaction of a job well done.

To his amazement, he had stayed hard the entire time; about 45 minutes. I sat up, took a drink of water and he asked me to suck his cock. He eased back onto the pillows, but I wanted to give him a show. I had a feeling he would not hold out for long once I started, so a good visual would be more memorable than the feeling of my lips around his cock.

“I am going to suck your cock now, baby. But I want you to sit up on your knees.”

I positioned myself in front of him on my hands and knees, my ass raised, shoulders lowered as I took his cock in my mouth, licking and sucking.

It was not the best blowjob of my life, not even close. But he was excited and turned on by the sight of me turning my head slightly to look up at him, my bare ass jutting off to one side, I didn’t care.

He was completely still, his legs trembling as I worked.

“Do you want me to tell you when I’m coming?”
“Yes.”
“Do you want me to come in your mouth?”
“No.”

He came almost immediately, gritting his teeth, coming into my hand as I milked his cock.

He brought me a towel and I wiped his jism from my arm and hand. We lay back on the pillows. His stomach growled.

“Have you not eaten lunch yet?”
“No, I thought that maybe we could grab a bite afterwards, if you’d like.”
“Well, I have another hour free; that’d be nice.”

He hesitated a second.

“Cara, would lunch be business? Or pleasure?”
“Honey, it is a pleasure to spend time with you, and our agreement is about my time, so I would say both. Business and pleasure. Just like here.”

I could almost hear the abacus clicking in his brain. He sighs, as I imagine him thinking of hundreds of dollars floating down around me.

“Yeah, I guess you’re right.We can have lunch another time.”
“That's fine, honey. When do I get to see you again?”
“Does next week, same time work?”
“It works perfectly. I’m glad. I had fun today.” I glance at the clock and, as I’d suspected, our time was up.

We talked casually as I dressed. He asked if I didn’t want to shower. No, thanks, but he absolutely should, I told him. People at the office might start talking if he walked in smelling like pussy.

I collected my things and he walked me to the door.

I kissed him goodbye, he pulled away and beamed, “You’re so fantastic!”

I smiled and walked out.

I was proud of myself; as horny as I was, I’d held off on the fucking. I just don’t think he’s ready for that, yet. I want to build up to it. I want to go sex toy shopping. I want him to know his way around me blindfolded.

I was glad he’d brought up the subject of lunch; I imagine he’ll take it into consideration in the coming weeks. I think he’ll probably decide that, once in a while, it’d be worth it.

For now, though, I’m content to have our encounters fairly brief—limited to these two hours—I’m cultivating a long-term professional relationship with him. I don’t want to jump the shark so soon.

I thought about something The Gentleman had said during his kissing lesson. While tracing my eyebrows, he whispered, "It's nice to be young, isn't it?"

At the time I didn't think too much of it, but as I write, I think that might be my most important job with him--to remind him what it is like to feel young. Anticipation and excitement can build to one hell of a good feeling. It feels like high school. And I smell like Teen Spirit.

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Professional Girlfriend

2005-10-04T22:23:00.000-05:00

I knocked. Two knuckles, three raps.

I took a deep breath and waited. Nothing.

I knock again, my heart beating a little faster. Waiting.

If he doesn’t answer this time, I’m turning on my heel.

The door pulled slightly inward against the jamb, like someone had jerked it from inside. Still, there was no turning of the handle, no clicking of the latch.

One more knock. Maybe he’d been in the bathroom…

The handle turned, and the door opened.

The Gentleman stood, smiling, and invited me in.

He was confused; the room had two doors, one off the interior corridor and another facing the atrium. He was expecting me at the first. He’d opened it, creating a pull of air pressure from the room which had made the door move as I stood outside, looking down at the kids in the swimming pool.

“You found it alright?”
“Sure. Piece of cake.” I walked past him into the room and he closed the door behind me.

It was a pleasant enough room: a king-sized bed, a desk and a small sofa with a coffee table. The drapes were open, the daylight from the atrium filtered by sheer curtains. Every lamp was on, and there was a football match on the television.

“How are you feeling, Cara?”
“I’m good, but I need to use the bathroom.”
“Please, make yourself at home.”

When I came back into the room he was standing beside the dresser.

“I was just going to go get some bottled water. Would you like some?”
“Thanks, actually, I have my own. But you go ahead.”

He walked out of the room and I looked around. He’d left his cell phone on the desk, along with a small bag holding a toothbrush and toothpaste. I smiled. Glancing to my left, I saw a small bank envelope sitting on the table. I stepped closer to look at it. Sealed, but what else could it be? I opened it, counting the bills inside and tossed it into my bag. Thank god we didn’t have to have that conversation. He’d done it exactly right.

I’d answered The Gentleman’s ad on craigslist earlier in the week. A successful, fifty-something businessman wanting a complication-free, ongoing relationship. There was no mention of sex, no mention of money, though both were implied, and the ad was well written. I held my response for a day, and then wrote him. That was Monday. By Tuesday, I’d had a reply from him, an invitation to chat, and a photo.

We met for lunch on Friday, and discussed the kind of relationship we’d both like to have (no attachments, no falling in love, that sort of thing.) He told me about his longtime companion, whom he loves very much, but who has all but shut down sexually since she went through menopause two years ago. I felt comfortable with him. He was smart and polite and did all the things that a gentleman does when in the presence of a pretty woman.

We discussed the boundaries I wanted to enforce: we talk when we are together. We don’t phone or email each other every day. Provided things go well, we meet at the same time every week at the same place. We never talked about sex, and we circumnavigated the topic of money. We were both being cautious. We decided that we’d get together on Sunday afternoon, two days from then, for our second ‘date,’ the first date for which I would be paid.

On Sunday morning he called with hotel and room number information. I took the opportunity to tell him what I considered to be a fair rate of compensation. He hesitated a little, but then said that it sounded good. I was glad. If he’d agreed too quickly, it would have been too little. And he had no idea yet how fabulous I really am.

The Gentleman came back into the room, empty handed, and said the vending machine wasn't working. He got some ice and poured himself a glass of water from the complimentary room temperature bottle of Dasani on the dresser. We sat on the sofa to talk.

“I’m very nervous…are you?”
“I am, a little…”
“I’m sorry about my hair; I’m due for a haircut. So, sorry if it looks bad.”
“Your hair looks just fine; it’s nice, actually.”
“I think your hair is gorgeous. You are just so attractive to me.”
“Thank you.”

He was so nervous he was sweating a little. I asked him questions about his work, slowly relaxing and sitting sideways on the sofa, facing him, my head in my hand, elbow on the back of the sofa. I had my legs crossed and twisted to the side.

“You have beautiful legs…”
Good. He noticed.

We chatted for nearly an hour; occasionally he put his hand out on the cushion and I put mine into it.

Clearly, I was in control. I decided to move things along.

“Have you ever had a massage?”
“No, never a professional massage…I think I’m afraid I’ll get, um…”
“An erection?” I asked.
“Yes.”
“I’d like to give you a massage. Would you like that?”
“Yes.”
“Good.” I stood and reached for my bag, pulling out several tealight candles and a lighter, “I am going into the bathroom. Why don’t you light these for me?”

He jumped to attention.

I peed, washed my hands and looked into the mirror. Okay, baby, I thought, you can do this. You are in control.

The Gentleman was waiting when I stepped back into the room. The candles were lit and he was standing next to the bed. I handed him the remote. “Please turn off the television, and then come over here,” I said as I turned the lamps off.

He walked over, and I took his hands. I spoke softly.

“I’d like to undress you now.”
“Oh, alright…” he started to remove his loafers.

“No, no, let me do that.” I got on my knees and removed his shoes. I unbuckled his belt and slid his trousers off, laying them over the chair.

“This is so hot,” he said. I smiled. I went to remove his socks and he flinched.

“Would you like to leave your socks on?”
“Yes, I think so…is that okay?”
“You do what makes you comfortable. It’s okay.”

I stood and removed his watch, polo shirt and undershirt. He stood in front of me in his light blue boxers and black Gold Toe socks.

“Would you like to leave your shorts on?”
“Yes, let’s leave them on for now…”

Our arrangement was for two hours. I had decided to approach this as if we were dating, using our time together to get to know one another, to achieve a level of comfort and longing on his part. We would not be having sex.

"Can I undress you now, Cara?"
"You, sir, may watch me undress."

I stepped back, removed my top and let my skirt fall. I stood, barefoot, in black panties, a camisole and my glasses. He was appropriately awed. His desire was evident in his breathing.

"Come over here, now, to the bed," I said, taking him by the hand.

I poured the oil and started massaging his back, taking my time and talking to him. He was very self-conscious and I did my best to put him at ease. When he rolled onto his back and i started massaging his shoulders and chest, he spoke.

"This is heavenly."
"I'm glad. I want to learn what you like."

His cock was hard.

"See? It happened!"
"That's so good, honey. You have a very nice cock... would you touch yourself while I massage your legs?"
"Ohhhh..." he whispered, "I want you to tell me what you like. What do you like to do?"

I moved his hand to his dick, grazing it with my fingers.

"I like to watch. I'd like you jerk off for me. I'd like to see you cum. "
"Mmmmm, my cock is dripping. See?"
"I do. That looks so nice. Can we take off your boxers now?"

I helped him out of the shorts and crouched next to him, one hand on his leg as he absentmindedly stroked his cock and looked at me.

He sat up, really unable to help himself. He moved closer to me. I kissed him. His were uncertain kisses, like he was out of practice and wasn't sure if he was doing it right. I made a note for our next date.

"Was that a good kiss?"
"That was just fine, baby... Can I ask you a question? How often do you masturbate?"
"Not enough."
"Why is that?"
"I think that, the more I masturbate, the more sex I'll want, and the more stamina I'll have."
"Well, then, let me make a suggestion to you."
"Yes?"
"Start wanking more. You'll need it!"
"How often do you do it?"
"Several times a week at least. Let's jerk off together now, and when you cum, I'd love it to be on my tits."

I took my cami down, exposing them. He took one in his mouth. I told him that he could suck harder, that it was okay. He pulled my nipple into his mouth. I made another note.

I sat back and slid out of my panties. We were lying, me on my side, facing him on his back, each of us jerking off, watching the other one.

Suddenly he got onto his knees and positioned himself above me. His breathing was so calm and he was so quiet, I couldn't believe he was cumming. But there it was, spilling out of his cock and dripping onto my tits. He had never done that to a woman before. I came to find out that there are a lot of things he's never done before.

I cleaned up and dressed. He wrapped his arms around my waist as I stood at the foot of the bed.

"I'm sorry you can't stay longer. That was amazing... and I just want to do more with you. Everything. Right now!"
"All the more reason to do this again. This was so nice. I'm glad we got to know each other a bit better. And I would like to see you again..." then, "... if you want to."

He looked at me incredulously, "Are you joking? Of course I want to see you again!"

"Good. Then let's talk on Tuesday when you know your travel schedule."

I picked up my bag and walked toward the door. The Gentleman opened it for me. I touched his shoulder, kissed his cheek and walked out.

Driving home I started thinking: Does this make me a whore? Technically, we didn't have sex, but Audacia Ray's definition of sex work is “the pre-agreed upon exchange of money or goods for erotic energy.” I am inclined to agree. Is this sex work? Or is it an 'arrangement?' Is there a difference? Am I a Whore because someone pays a lot of money to spend time with me, whether or not we fuck? A Rentgirl? A Sugar Baby?

The crux of it is, The Gentleman, above all else, wants someone with whom he can be intimate. Someone who will pique his interest and imagination. Someone he can date and enjoy spending time with, whether at dinner or a football match or a nice hotel. The nearest I've come to an acceptable term is "Professional Girlfriend." I think it works.

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