Sugar Baby Weekly

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.



  • At 1:53 AM, Anonymous Anonymous said…

    very nice, I'd like to read more!

  • At 7:08 AM, Blogger Viviane said…

    Very nice, Cara, and welcome to the blogosphere. Would you email me at some point? (You don't have an email in your profile. Perhaps you need a Gmail address?). Ciao, bella.

  • At 8:25 AM, Blogger Dacia said…

    I'm not sure you have to decide what to call yourself, just be aware that other people would likely call you a whore - and not always in that nice way.

    And a word of advice about these kind of situations - maintain your hourly rate. Don't let him talk you into less because you see each other often - often regulars will try to talk you into accepting less money for more action over time. Sure he's nice, but be a good businesswoman about it, and remember to maintain that boundary.

  • At 10:36 AM, Blogger Jefferson said…

    Beautiful writing about a delicate situation, beautifully handled.

    You leave me curious to know more about yourself, more about the Gentleman (are there more?) and the development of the relationship.

  • At 12:06 PM, Blogger Cara said…


    Three of my favourite bloggers and one horny anonymous person already coming to call. This blog isn't even twelve hours old yet!

    Dacia, Viviane and Jefferson, thank you for the advice and encouragement; I hope to post here weekly after my sessions with The Gentleman.

    This is my first foray into 'sex-for-money-land,' and I hope to chronicle this professional relationship (I don't have any others) partly as entertainment, partly as introspection.

    And while I would wear the label "Whore" with pride, were it tossed(not in the good way), I feel a bit 'green' in the sex business to merit such a tag. I love the idea of reclaiming the pejorative.

    Perhaps, one day.

  • At 2:11 PM, Blogger marcus said…

    you dont have any other relationships? hmmm, perhaps you and i could start one up. you sound very hot. and smart. with a sense of humor, too. damn, girl - where are you?

    oh, i just re-read that. maybe you meant you dont have any PROFESSIONAL relationships. well, im a sex worker, too... if we got together, THAT would be a professional relationship. i'm based in dc. if you are ever here, hit me up.

    by the way, what dacia wrote - in terms of being called a whore, but not in a nice way - just doesnt happen to men. this double standard still exists; in all the time ive been a whore, ive never been called one by anyone other than my friends who are also whoring. life sure is different when you have a penis.

    i am serious about dc. but i would love to see a pic of you first. will you send me one, sugar baby?

  • At 7:45 AM, Blogger MonMouth said…

    Welcome to Blogland Cara. This is an ambitious opening post.

    I'm looking forward to seeing how things develop. Now, are we to take the title literally and assume there'll be nothing more posted for another week?

    *a welcoming kiss on the cheek*


  • At 1:27 PM, Blogger Viviane said…

    Ah, Cara, we found you through Statcounter. I do enjoy reading my referrer logs, one meets the nicest people there.

  • At 1:33 PM, Blogger Prospero said…

    The Gentleman is getting just what he desires and needs. Things he has never done with a woman before and in his 50s? Good for him. And good for you. Best of luck... and thanks for sharing.

  • At 12:57 AM, Blogger Darkneuro said…

    Sugar Baby: Great start, added immediately. You're a GOOD writer.

  • At 3:55 AM, Blogger magdelena said…

    Hello Cara,

    Beautiful first post about a thrilling experience. I'll enjoy reading about your intimate times with The Gentleman as you explore this aspect of yourself and the developing relationship with him.

    In case you are curious, I come to you via your comment on figleaf's site.

    Be back to see you soon sweet Sugar Baby.

  • At 4:54 AM, Blogger Leela Lamore said…

    Welcome to Blogland Cara. I found you via Figleaf.

    You have a very senditive way of writing and I too look forward to reading about the journey you are on.

  • At 4:56 AM, Blogger Leela Lamore said…

    lol that was supposed to be sensitive, not senditive *smile*

  • At 2:29 PM, Blogger AlwaysArousedGirl said…

    Thank you for sharing. Call yourself a Whore proudly, with tongue in cheek, with a big smile on your face.

  • At 9:56 PM, Blogger Stanley said…

    Ah, the magic of linking and link trackers. You have a bunch of sex blog bigshots coming by on your very first day. And a great start that is. Very pleasant to read you. Very real and human. And sexy. Looking forward to more.

  • At 1:57 PM, Anonymous Anonymous said…

    I wish i could meet someone like you. I'm in a situation like your "gentlemen", i love my wife, but i'm so lonely it hurts.

    I can't really do the girlfriend thing, just too complicated, and all my expieriences with women of a more professional nature have been very disapointing (typical L.A. slag). you give me hope, maybe someday


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