Sugar Baby Weekly

Thursday, October 27, 2005

Crazy Talk

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?

Thursday, October 20, 2005


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’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.

Thursday, October 13, 2005


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?”

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?”
“Do you want me to come in your mouth?”

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.


Tuesday, October 04, 2005

Professional Girlfriend

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.
“I’d like to give you a massage. Would you like that?”
“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."
"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.