Sugar Baby Weekly

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.



  • At 4:37 PM, Blogger marcus said…

    well, cara, ive been checking your blog waiting for your next post. you didnt let me down. in fact, you kinda got me "up". and that doesnt really happen to me- im a no-porn, no-cyber kind of guy. i only like it live.

    anyway, as a sex worker, i can tell you that like your friend, i too had to learn to accept compliments gracefully. it wasnt natural at first. ive even had clients who like me to just stand in front of them, and slowly turn around, so they can simply look at me. what an ego-booster... one of the perks of the job, as far as i'm concerned.

    again, i am extending an open invitation to you--- if you are ever in dc, please contact me (if you would like, that is). i would love to take you out for a drink and just shoot the shit. you strike me as a very dynamic, very intelligent woman who is refreshingly REAL. enuf said on this. in the meantime, i'll just continue to read your weekly posts.


    ps it suddenly occurred to me... you sound like you might not be in the united states. hmm, cara, care to tell us- where are you based? will you tell us a little bit more about you? you wrote on your profile, "i probably live next door to you."

    i wish.

  • At 5:33 PM, Blogger Madeline Glass said…

    oh, marcus.

    stop hounding the poor girl!

    madeline here, cara. i am really enjoying your blog. it has been a weekly treat so far, and i hope you continue with it.

    and if marcus keeps harassing you, email me; i'll tell you how to handle him.


  • At 10:54 PM, Blogger Cara said…

    Marcus, the compliments are getting easier to accept. I should be careful not to get too used to them, eh? As far as my location goes, well, let's just say I'm in North America.

    Madeline, I love the way you write about your life- love, sex, kids and the rest of it. Thanks for the comment, and the offer!

  • At 3:35 AM, Blogger Leela Lamore said…

    Oh Cara again beautifully written. It was with eager anticipation that I clicked on your link for the umpteenth time in the past week, to be rewarded with your words at last.

  • At 6:29 AM, Blogger Viviane said…

    Marcus, stop gushing, ok?


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