Aristippus - Jenny's Story

"Well," he said, "I can't do anything about the price of real estate around here, but maybe I can help you pay your rent." He was clearly ready to get started. So, still holding my wine glass, I stood and said, "Well, let's move to the bed."

I just had a crowded one-bedroom, but I had done my best to make the most of it. I had lit several candles around my room, dimmed the lights, and placed a protective sheet in the center of my bed. As I set my wine glass down on my nightstand, Caleb had already started stripping. He immediately pulled off his shirt the moment he entered my room. Then, he quickly sat on the bed to remove his shoes and socks. He then stuffed his socks into his shoes and placed them neatly under my bed - I thought that was weird. As I just stood there watching, he unbuckled his belt and pushed his pants to the floor, before neatly folding them and hanging them over my vanity chair.

All this time, I was just standing there watching him. He picked up his wine, took a sip, and looked over at me, wearing nothing but his underwear. "Okay?" he asked with an impatient tone in his voice.

"Oh, absolutely." I quickly responded, setting my wine glass down on my bureau. I was still fully dressed in white Balloon Pants (aka Harem Pants) and a blue-gray halter top. I thought it looked pretty sexy, so I wasn't actually planning on taking either the top or the pants off, but I was open to it if the subject came up. But since I'd never done this before, I was still waiting for his guidance. And at that moment, I was just standing there, three feet away, holding a bottle of massage oil.

"How do you want me?" Caleb asked, also expecting directions.

"Oh, I'm sorry," I said with a smile. I realized that I needed to give direction, or we'd just be standing there in an awkward stalemate. "Yes, please lay down on your stomach."

"Should I leave my shorts on?"

"Oh, I don't care, whatever makes you comfortable." And with that, he dropped his drawers and laid down in the center of the bed. I only got a quick glimpse of his package, but it looked what I assumed was normal. When I saw Seth naked, he was almost always in a state of semi-arousal. And Caleb wasn't quite there, but I assumed he would be soon.

I sat on the edge of the bed, filled my hands with massage oil, and immediately started on his back. Surprisingly, I liked it. I like the feel of massaging a man. Even though it wasn't anyone I had an interest in, just the simple fact of giving him pleasure was giving me a sense of gratification. I was straddling his legs and pressing vigorously on his back. And the harder I pressed, the more he oohed and aahed. And the more he sighed, with a deep sensual moan, the more I got aroused.

While he was still on his stomach, I worked on his neck and shoulders, before sliding down his legs as I moved to his butt cheeks and upper legs. As I slid off the foot of the bed, I said, "Okay, big boy, flip over." He immediately rolled over onto his back, and I admit, I was impressed. His pecker was five or six times the size it had been before I started on his backside. It was now fully erect, hard and standing tall. I stood at the foot of the bed in awe. The only other penises I'd ever seen in my life was Seth's. And briefly Ian's - but his was in Seth's mouth at the time, and I was in shock. So, I'm not sure I really did a detailed analysis of its length and girth. But in any event, Caleb's was bigger, longer, thicker. More adult, if that makes sense.

I quickly forgot about everything else. I refilled my hands with oil and wrapped both hands around Caleb's twitching pole. He let out a long sensual sigh, and I slowly began my stroke. It was only a few minutes before Caleb reached to touch me. I was sitting on his legs and just out of reach, but I didn't want him to try to sit up, so I moved to his side without breaking my stroke. This allowed him to run one hand up and down my leg, while he slipped his other hand under my halter top, so that he could run his fingers back and forth across my very erect nipples.

This was all it took, and he was done in less than sixty seconds. A hot stream of man cream shot straight up in the air, maybe a foot or more, and landed in big splats on his belly. He let out the loudest groan I had ever heard, as I milked him for every last drop. "Shhh," I said as I let go of his pulsating pecker and brought my fingers to my lips. "My neighbors will hear you."

That sort of brought his contractions to an end, but he was still breathing very hard. "Your neighbors can't hear us," he laughed.

I also laughed, for he was probably right, but he was loud, so it was possible. Rolling off the bed, I went to my bathroom to get him a wet washcloth. I started to hand it to him, but realizing it would probably be better service if I did it myself. And he did seem to enjoy it; I just wish I'd warmed it up first. Another lesson learned for next time.

Once I had him all cleaned up, I threw the washcloth into the bathroom and then picked up both of our wine glasses. He hadn't paid me yet, and though I knew he was good for it, I decided to wait at the kitchen bar - between the bedroom and my front door.

Once he was dressed, he walked out into the living room, and seeing the two empty wine glasses on the bar, said, "Why don't we finish the wine?"

I agreed and retrieved the half-empty bottle from the refrigerator. Caleb refilled both glasses and sat down on the closest bar stool. "Thank you, Jenny," he said after a sip of wine. "You have amazingly talented hands."

"Well," I said. "You have an amazingly beautiful mussel to work on."

He almost blushed - but not quite. "Why, thank you," he said. "I guess you wouldn't mind working on it again then?"

"No," I said after a sip of wine. "I wouldn't mind at all."

He took a long sip of his wine, and then after a slight pause, asked, "So, do you offer any additional services?"

My first thought was that he was asking for straight sex - that is, to fuck me. But after another slow sip myself, I reconsidered. "Well, possibly. What did you have in mind?"

He made the middle finger salute, but instead of pointing it at me, he brought it to his own mouth and sucked it. I instantly got the message; he wanted a blow job. I had never actually given Seth a real blow job, at least not all the way to completion. Which now I felt bad about because he certainly did give me oral sex to mind-blowing orgasms, many times over. So, I should have returned the favor; I just never did.

"That could possibly be arranged," I finally said. "For the right price."

"How about four hundred?" he said with a smile.

"Okay," I said slowly, still that sure of what I was getting myself into.

"And, as I'm fully naked, maybe you would be more comfortable naked as well."

Again, I shamelessly nodded my approval.

"And maybe you'd allow me to lick your pussy as well?"

"Five hundred," I quickly said. And Caleb eagerly nodded his acceptance.

I was nearly finished with my wine when I said, "Caleb, why don't you just get married? You could have sex every night."

"Oh no," he immediately replied. "I've been there - done that. Never again. I like my freedom, I like the variety, and besides, it's actually cheaper."

The instant he said that, I realized I wasn't charging enough. Crap, but I'd already quoted him five hundred, and I couldn't raise it now. But if and when he wants to fuck me, it will be more - much more, I told myself. He finished his glass of wine and slid two one-hundred dollar bills toward me. And after a sweet hug, he was out the door.

Two weeks later, Caleb was back for his usual trim. Cutting his hair was easy, because he came in so frequently that it never got out of control. And as I was giving him the usual, post-trim shoulder massage, he asked, "Are we on again for the extra service?"

"Sure," I immediately answered. "I was hoping you'd become a regular."

"How about Friday at seven again."

Friday was okay, but for some stupid reason, I kept hoping to restart my social life, and Friday would be a good date night. But there was no date in sight, and besides, it was mostly my fault. I didn't even try to find a guy, so who was I kidding? "Sure, Friday would be great," I said.

Knowing that I had agreed to additional services, I dressed a little differently this time. I still wore my balloon pants, but now without panties. I thought Caleb would like that. And, instead of the halter top, I wore a blue sweater shirt. It was a crop top with three-quarter sleeves. But with a low-cut front and a bare mid-riff, it was very sexy. I didn't wear a bra, as my boobs are so small it hardly mattered. But when aroused, my pointy nipples become clearly visible through the tight-fitting sweater, and I think that's very sexy.

He knocked again at seven on the dot, and as I opened the door, he was carrying another bottle of wine, bubbly this time, and a bouquet of flowers. "Very nice," I said, as I accepted both from his hands. As I looked for a vase for the flowers, Caleb poured us both a glass of wine, and with bubbly in hand, we quickly retired to the bedroom. We made small talk for about two minutes, clinked glasses, and started to undress. I let him get ahead of me, as I had less to remove, and I wanted to do a little strip tease for him anyway.

Once Caleb was fully naked and sitting on the bed, I pulled one arm out of my sweater, and then seductively the other arm, before slowly removing the sweater off and over my head. I then folded it very neatly, taking my time, and placed it carefully on my vanity. Then twerking my hips to a silent rhythm, I pulled the drawstring to my pants and let them fall to the floor. I was right, he was surprised that I wasn't wearing panties, and as expected, he loved it.

Now as naked as he was, I said, "How would you like to do this?" Implying that I didn't know if he wanted me to give him a blow job first, or did he want to start by going down on me. Apparently, the answer was neither.

"Why don't we start with you giving me a light massage first? That should get things going." And as I reached for the massage oil, he added, "Hey, do you have any powder? Like talcum powder or baby powder."

"Instead of the oil?" I asked. He nodded yes, and I put down the oil and went into the bathroom to look. Not finding anything, I remembered that I had some after-bath powder on my vanity. Walking out of the bathroom, I signal that I might have something. "How about after bath powder?" I said, as I picked it up to show him.

"Perfect."

"It smells really girly," I warned.

"More perfect," was all he said.

As Caleb rolled onto his stomach, I straddled his legs again and sprinkled the highly scented, blueish powder liberally to his back. As I rubbed it in, on his neck, shoulders, and back, I asked, "Do you like this?"

"Oh yessssss," he moaned. "It feels so good."

And I had to agree. It was silky smooth, easy to apply, and my hands glided across his skin as if they were on millions of teeny tiny ball bearings. And additionally, it was cool to the touch, smelled wonderful, and left no sticky residue. "Where did you learn this trick?" I asked.

"From my Ex," he said, between oohs and aahs as my hand effortlessly glided up and down his back.

After about fifteen minutes, I figured he was ready for the next step, so I slid off his legs, and lying beside him, rolled him over. And since he never indicated who was to go down on who first, I figured that if he didn't make the first move, I would do him first.

There was a short pause in the action as I waited for some kind of signal, and just as I took his dick in my hand and began to lower my head, he grabbed my legs and pulled me to his side, aligning my bush with his face (I still didn't shave in those days), and with my face aligned with his Johnson. Apparently, we were going to do each other at the same time.

I'll be honest, at that point in my life, I had never heard of sixty-nine. I didn't think I was that naive, but apparently, I was. Seth and I never tried it, and though I felt like I had a pretty good understanding of the erotic arts, Caleb proved to me that I was just a Babe in the Woods. And he was the Wolf to take this Little Lamb to Slaughter.

We were both lying on our sides, so no one had the advantage over the other, which I liked. And as Caleb lifted my upper leg, he gently placed his head on my lower thigh and slowly began to lick me. It felt so good, and my mind immediately flashed back to all of the times that Seth buried his face deep between my legs. And that caused me to just naturally, and almost unconsciously, take hold of his man meat and bring it to my lips.

Now at this point, I have to admit that he did not taste like Seth. I have no idea what the difference was. I don't know if it was better or worse. It was just different. And now, thinking back, I assume it had something to do with Seth being my lover and Caleb simply being a client - a John. And like I said, one wasn't better than the other, they were just different, and that fact has always stuck with me.

I couldn't get his entire dick into my mouth, so the best I could do was maybe the top third, and I just slowly stroked the rest. Caleb also wasn't at the best angle, but he was trying hard to get me off. So, after maybe ten minutes in this position, he rolled to his back, got up and moved between my legs. At first, I thought he was going to fuck me, and I wasn't ready for that. But no, he just wanted a better angle to eat me, and after inserting two fingers, and vigorously pumping them back and forth, he continued licking and flicking my clit until I came. It was a nice little orgasm, and I admit it was primarily mechanical, but still a sweet climax.

Then, while still between my legs, he got up on his knees and jacked himself off until he blew his load all over my belly and titties. I would have done that for him, but I think he was tired and frustrated that we were unable to get each other off simultaneously.

He did leave me the five hundred dollars though, and he did become a regular. As did several other gentlemen. After six months, I was almost making as much after hours as I was with my barbershop. And when my lease was up on my one-bedroom apartment, I moved to a two-bedroom in the same complex. The two bedrooms were more spacious in every respect - bigger living area, bigger kitchen, and bigger bathrooms. But what I really liked was that they were designed with two master bedrooms. That is, both bedrooms were the same size, and both had ensuite bathrooms. That way, if a patron (as I called them) needed to use the bathroom, or take a shower before or after a massage, they wouldn't have to use mine. I called them patrons as the definition of a patron is someone who financially supports a given cause or person. And that person is me. Besides, Patrons are what they call people who support the fine arts, whether it's the art of ballet or the art of Personal Indulgence.

I purchased a massage table and set up one room as my massage studio. And the other I reserved as my private bedroom. In the massage room, I had shelves of towels, massage oils, soft powders, and other personal grooming products. I actually developed a small Personal Grooming practice, as some men prefer a well-manicured personal area. The other bedroom was my private sanctuary, and I rarely allowed patrons entry.

My barber shop was decorated with pictures of me dancing in various ballet performances. So, my daytime clients were all aware of my other interests when I wasn't cutting hair. I frequently received comments about my athletic figure and my flexibility - which frequently led to questions about, "What other physical activities are you good at?" Which, of course, would lead to me handing them a business card and suggesting they call me later to find out.

I'm amazed at how horny men get watching me dance, especially if I danced for them fully nude. And for the select patrons, I did dance naked for, I was utterly flabbergasted at what they would then pay to fuck me. But it's their money. And if they were that dedicated a patron of the arts, then who am I to question them?

As for my personal grooming, I started shaving completely shortly after my first visit from Caleb. I didn't realize so many men would pay to eat my pussy. And being totally bald down there seems to be preferred by most patrons. I now wax instead of shaving, as there is a waxing studio in the suites where my shop is. And it seems to have multiple advantages. First, it makes me look younger, especially when combined with my A-cup titties and the fact that I wear my hair long. And though I don't think any of my patrons are pedophiles, I think some of them do like their girls young. So, if I can fill that fantasy for them safely and legally, so be it. And secondly, now that I'm used to it, I feel it is more sanitary. I know that might sound weird, but I pee from down there, and it is easier to keep clean if there just isn't a bunch of wet hair.

I printed new business cards that included my private cell phone number, and I handed those out only to men who expressed an interest in additional massage services or a very personal ballet performance. I've raised my prices at my barber shop, and I still stay fully booked five days a week. I also still teach ballet, which I love. And I see at least two gentlemen a week for a personal massage. They don't all request extra services, but many do, and I make a very nice income off the extra business. And I do admit to having sex with selected patrons. We usually end up back in my private bedroom, and though not a single one has actually spent the night, I'm secretly hoping that happens soon. However, I have never seen a patron other than at my apartment, and I'm getting tired of that. I want to broaden my business, so that I am truly a full-service provider. So, that's why I signed up for the Aristippus Retreat. I'm hoping to expand my business so that it's not just Patrons with Benefits, but Sugar Daddies with Benefits also.