Confessions of a Teen Gay Escort Ch. 05

There are three things I'm often asked when people find out I'm an escort:

1) Do you have a boyfriend? (followed by) Does he know you do this?

To which I answer: yes, I do have a boyfriend (more on him later) and yes, he does know and approve. He's even referred some customers to me.

2) Do you enjoy the sex?

Oh god yes. I enjoy sex in general, if I didn't do it for money it would be my main hobby. I love the look on a fifty-something gay man's face when he first sees my tight butt wrapped in leather. I love feeling his hands caressing me, exploring every inch of my body. I love the first taste of precum on my tongue, and the first tentative touch of a cock against the flesh of my ass. Sure, some clients can be off-putting or boring in bed, but there are plenty who excite me and turn me on big time.

3) Do you ever feel ashamed about your job?

Well, I don't exactly shout it off the rooftops but that's mostly because there's still a lot of stigma and I'm tired of people treating me differently just because of what I do. However, personally, I'm not ashamed at all. Why would I be? I make great money doing something I love, I work about 20 hours a week, and there's a lot of additional benefits.

For example, one of my clients (or two of them, to be precise) invited me over to their luxury villa somewhere in the Mediterranean. This was the couple I was talking about earlier, the two who liked to play with food. Let's call them Frits (the taller, more dominant one) and Jan (the more mellow, more passive of the two). They rang me up one day and told me about their villa, and how they would like me to join them there in the summer. They offered me plane tickets and a generous sum of money to come over and spend a week with them, having lots of sex of course. They warned me that they wanted to get pretty kinky, but I had done plenty of kink before so I wasn't fazed (at that point).

Well, that week turned into just about the hottest experience of my life. Firstly, the villa was very secluded, located in some beautiful hills with nobody around for miles. This allowed us to be completely indiscrete in and around the house. I was told not to wear anything but a thong and leather boots while in the home, and since we only rarely went out, that's all I wore for most of the week. The villa was also fantastically well equipped, complete with a huge terrace, a pool and adjoining jacuzzi.

Secondly, the men had brought a lot of weed. I don't smoke that often, but when I do I always get incredibly horny (I had mentioned that to them before, which I suspect was why they had gone through the trouble of bringing it). Every night, we sat on the poolside couches together and got very high. The first time we did, on my night of arrival, Frits had me lie on his lap as he lazily played with my balls and cock. Somehow, the subject turned to safe sex. I confessed that I had never tried bareback anal sex before, to which both men expressed surprise. They told me it was much nicer than safe sex for both giver and receiver, and insisted we try it that night.

Now, of course I had been curious about how doing it felt without a rubber, and had occasionally toyed with the idea of trying it in my personal life. However, Louis forbade it for any of his escorts and had put me off the idea with his speeches about AIDS and other horrifying diseases. So I resisted when they first suggested trying it, saying I wasn't supposed to. They pointed out that I had already practiced unsafe oral sex with them once (see my earlier story) with no ill effects, and that they were both tested recently and completely clean. It was a little foolish to take them by their word, but finally I agreed.

We went up to their bedroom and soon I was on all fours, nude but for my boots. Frits dripped a good stream of lube and started warming me up with his fingers. I've learned to loosen up very quickly, and so it didn't take long before I got my first sensation of a bare cock against my rosebud.

I have to say, it does feel nicer to feel your partner's skin against yours as he enters you. It's so much more intimate than when he's wearing his rubber shield. Frits started thrusting, he was blessed with an above-average size cock and I had to smile through the pain for the first few minutes but started to enjoy it again soon after. In fact, I got curious about how it would feel when he orgasmed, so I clenched my sphincter a little to get him there quicker. Soon, I felt him slowing down and erupt inside me. I didn't feel THAT much of the actual orgasm, but I definitely felt his cum gushing inside me after he pulled out.

Jan wanted to try, too. He laid down on the bed and I got on top of him in a sort of reverse cowgirl position. I rocked back and forth on his smaller but thicker cock while jacking myself off, which allowed us to time our orgasms perfectly.

After that, we decided to abandon condoms for the rest of the week. Every morning, I came into their room in my thong to bring them coffee and a blowjob. I got under the sheets and went to town on their cocks as they read the paper with a latte.

During the day, we mostly just chilled. Sometimes, we went into town to get something to eat and I was 'allowed' to wear clothes. Usually, though, we hung out by the pool, going in occasionally to cool off. I always rubbed the sunscreen on them and one of them did the same for me, and occasionally they had me give them massages.

However, it was at night, after some wine and usually a joint or two, that we really got going. One night, we got back to playing with food. This time, they had me lie down on a sun lounger and poured almost a full jar of honey over me before joining forces to lick it off. Now, the sticky honey was pretty much impossible to get off, but it was worth it for the almighty licking (and sucking) it led to.

Another night, we tried having sex in the pool. I slipped out of my thong and got between my two lovers in the pool. We kind of circle jerked for a few minutes, and then Frits and Jan showed me how it was done as I watched and wanked. Next, I was up.

Jan made me lean against the side of the pool with my hands and spread my legs as he got behind me. Sliding in went a lot easier than on dry land, and pretty soon I was getting my ass hammered. We tried a few different positions, he managed to pick me up with ease in the water which allowed us to have sex face to face with my legs wrapped around his torso. That stance felt amazing, somehow he hit me exactly in the sweet spot. I was also able to feel much more of his orgasm, which took a while but was totally worth it.

On the last evening, we got high again and decided to watch some porn on Frits's laptop. We flicked through some videos, until one of us suggested we search for threesome porn to get some 'inspiration'.

We ended up trying a 'train' which is anal sex with three men in a row. I was at the 'bottom of the pile' first, which was interesting because of my penetrator Jan's erratic and irregular movement due to getting fucked at the same time. Then, I got in the middle, which was mindblowing. To feel your cock inside someone's ass while simultaneously getting one in your own is indescribable. You're constantly 'switiching' from feeling it in your cock to feeling it in your rectum. Give it a try, if you ever get the chance.

But the hottest sex came on the second to last day. the men wanted to go for a nature hike. They asked me to wear my very short jean shorts and a white tank top, and they lent me a pair of thick socks and hiking boots.

We set off into the beautiful desert mountains. There wasn't a soul around, except for a solitary sheep herd we saw in the distance. We walked for about an hour, until we came into a small rocky gorge. There, Frits decided we should rest. He sat down on a rock and had me sit on his lap, as he liked me to do.

He kissed me, and we started making out while Jan sat next to us and rubbed my leg. Before I knew it, my shorts and top were off and I was naked but for my boots and socks, getting felt up by these two studs.

Frits wanted anal. I didn't want to do it at first, because we were out in the open, but Jan backed his partner up, saying there was nobody around for miles. Finally, I consented as long as they made it fast. I got lubed up, and squatted over Frits while he sat, with my legs akimbo. I mounted him in and he gave me a hard quick fucking. After he finished, Jan said he wanted to do it too. He put my shorts down on the rocky path, and told me to get on my knees and hands. I got another quick assfuck and a shot of cum in my rectum and got up, eager to get back to the house so I could clean up a little. However, as I got up, Frits quickly grabbed my shorts.

"Give them back!" I said, but he just smiled mischievously.

"When we get back to the house," he said. "I want to see you do the naked walk of shame all the way back"

Well, that was pretty exciting and humiliating at the same time. I walked for over an hour, stark naked but for my boots and with cum dripping out of my ass. The guys kept making jokes about me getting an even tan this way, but at the time I wasn't really in the mood for jokes-especially not once we went past the sheep herd again, who had moved over close enough to see me in all my naked glory (though he was mercifully still quite far away). However, looking back at it, that was a pretty damn hot thing to (have to) do.



So, that was my sexy holiday with the two foodies. I'll see if I can find something else to write about for the next story. If you have anything you'd like to know, please ask me in the comments or send me a PM. Thanks for reading!