Sugar Baby Weekly

Thursday, August 23, 2007

Business or Pleasure?

"Cara, he's so hot!"

"Yeah, good thing he's married."

"Keeps things simple?"


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."

Saturday, August 11, 2007

Dressing Up

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."


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."

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Saturday, August 04, 2007


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.

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