Confessions of a Teen Gay Escort

Hi there, and thank you for reading my story. Let me introduce myself-You can call me Jason. I'm 21 years old and I live in Amsterdam, where I have been working as an escort and an erotic model for the last two years. Let me start by telling the story of how I got into the sex trade.

I moved to Amsterdam when I was 18, from a small, conservative town a few hours away. I had come out a year before, but was generally shunned for it, and I was happy to move to the gay capital of the world. I enjoyed my first few months in the city a lot. I got a job at a gay bar, which allowed me to meet a lot of like-minded guys. I dated a few guys left and right, but nothing too serious. Mindful of getting a 'reputation', I made a point of not dating any of the customers in the bar I worked at (at least not the regulars). There was, however, one guy who wouldn't take no for an answer. We'll call him Jim here. He was in his early 50's, but in good shape. I had a thing for older men-my first experience was with an older neighbor, and I had felt a strong attraction to dominant, mature men ever since. You won't be surprised to find out that I am predominantly a bottom, though I had not done much anal sex at that point. But, a rule's a rule and I had to hold Jim off. When I kept turning him down, he finally tried to offer me money to spend the night with him. I was almost insulted at first.

"Prostitution was for down-and-out drug addicts!", I thought, "Guys so desperate for their fix that they resort to sucking dick for it. That's not me!". However, Jim said that he sometimes called up escorts through an agency, and that they were almost always intelligent, well-adjusted young guys who just decided that there was nothing wrong with making money doing what they loved. To prove his point, he actually took one of his 'dates' over to the bar when I was working, so that I could ask him about it.

The escort was everything Jim had said, and more. His name was Ricardo, and he was a handsome, latino-looking guy in his early twenties. He was affable, charming, witty and smart, if a little effeminate (though I've been called that several times myself, so I shouldn't judge). We chatted, and he told me that becoming a rent boy was the best decision he'd ever made. He worked whenever he wanted, usually only about 20 hours per week. I asked him about how much he made (rude, I know) and he said that at times, he made as much as 200 euros per hour, which was more than 10 times what I made at the bar.

Ricardo's stories had stirred my curiosity, and when Jim asked me again the week after, I tentatively agreed to discuss it with him, deciding for myself that I would try it out if the terms were favorable enough. We met up for coffee at a quiet little place to sort out the details the next day, and I prepared a set of firm rules to make sure I wouldn't regret trying it. He asked me what I was prepared to do. I told him that I was fine with oral and anal but the latter would have to be safe. I wouldn't swallow, and I wouldn't do anything disgusting like scat, or anything involving physical abuse (I had a date with a guy who tried to choke me for thrills once, don't want that again). Jim asked if I did massages, I said I didn't have much experience in that but that I wouldn't mind trying. He then made me an offer: 500 euros, to spend the night (8 to 8) with him. It took me aback a little, as I was expecting something more along the lines of two hours, but on the other hand that was fantastic money (or so I thought at the time). Excited, and a little greedy to be honest, I agreed. I would come to his house on Friday, bringing lube and condoms of my preference.

In retrospect, it was a little stupid to just agree to come to his house like that, but I had no idea how these things went down at the time. Anyway, I cycled over to the address he gave me, in a village just outside of town. I was surprised to find that Jim lived in a large, free standing house with a big garden. I didn't expect him to be so rich, despite him being able to afford 500 for a night with a rent boy. He welcomed me in, gave me half my money upfront as agreed (just in case he decided to do anything too weird and I wanted to leave quickly), and poured me a glass of prosecco.

We sat on his couch. He had lit a big candle on the coffee table and dimmed the lights, which definitely created a nicely intimate atmosphere. I was nervous, and he could sense it so we just sat and talked for a while. He told me that he had got his fortune from founding a famous clothing brand (can't say which one here), and had sold out a few years before. I asked whether he had a boyfriend, he told me he didn't because he didn't like to be tied down.

After a while, Jim put his hand on my knee and asked me if I was comfortable. I told him I was. He then asked me to undress in front of him. I got up and slowly took off my shirt, my pants, socks and finally my underwear (I had put on the sexiest, tightest pair I could find). He made me turn and show my body a little, to which he 'mmm-d' approvingly. He then asked me to give him a massage. Fully prepared, he grabbed a towel and a bottle of massage oil. The towel was spread out on the floor, and he handed me the bottle of oil. First, he had me pour some massage oil over myself, which ended up being a lot of massage oil. As I rubbed it all over my body, from my chest down to my arms, legs, butt and crotch, he took off his pants and started to jack off. To my relief, I noticed that his cock was average size, not much bigger than mine (both my body and my cock are pretty slight). He was uncut (as most European men are) but, as I was soon to find out, he kept himself very clean.

Jim then took off the rest of his clothes, and laid down on his stomach on the towel. He told me to straddle him and get to work on his back. I sat down and poured some oil over him, then proceeded to rub his shoulders, neck and lower back. He moaned in pleasure, and I tried to eroticize it a little by making my movements very slow and deliberate. A few minutes in he asked if I could do his chest too. He turned around, so that I was now sitting on his lower abdomen. Relishing his newfound mobility, started working on me with his hands, sliding them over my chest and finally down to my cock. As he worked on me, I felt his erection grow against my butt.

"Did you douche?" he asked, and I told him I had. "In that case, do you mind if I play with your asshole?" I was fine with it. I got up, grabbed my bag and gave him my lube. I sat down on him again, this time with my back turned to him so that he would have easy 'access'. He gently worked on my hole with his fingers, slowly inserting a finger and feeling up my prostate. Being in this position allowed me to play with his cock at the same time, which he clearly enjoyed. He then had me slide backwards, into the 69 position. I took his cock in my mouth and started blowing him as he put a second finger inside me, teasing my balls with his tongue as he worked on my hole.

We went on like that for a few minutes, until he pushed me off his dick. "Are you ready to get fucked?" he asked. I was. He made me sit on the towel on my elbows and knees, the latter a little bit apart. He got up behind me on his knees, and I felt a stream of lube flowing into my crack. He wanted to go in without a condom for a second, so I had to back off and insist that he wrap up before going in. Disappointed, he let me slide a durex around his dick and I got back into my wide-knee crouch. Slowly, he eased himself inside me.

I have to say, Jim is very good at fucking. He deliberately took his time to go all the way in, to the point where I had to impatiently scoot myself backward to feel more of him, and he varied his tempo nicely once he started fucking. Occasionally, he leaned over to give my cock a few jerks too. Finally, he started thrusting very quickly and then stopped abruptly as I felt him throb hard inside me.

He took his cock out and discarded the condom. I was a little disappointed not to get off myself, but that was part of the job I guess. He invited me to go upstairs. I took a quick shower to clean up, and we got under his nice silk sheets and spooned naked.

The next morning, we woke up around seven. Apparently realizing that we only had another hour left, Jim asked me to shower with him. In the shower, he cleaned his groin with some soap, then washed it off and told me to get on my knees. I had never blown a guy in the shower, and I occasionally got water in my mouth and half-drowned, but Jim seemed to enjoy it. Even then, I was pretty proud of my cocksucking skills, having watched quite a few how-to guides online while practicing with a condomed cucumber. I like to take his head inside my mouth, then working the sensitive underside with my tongue-drives most guys crazy. Anyway, It didn't take long for him to reach orgasm. He pressed me off him, but I still took most of his load in my mouth. I toyed with the idea of swallowing (maybe I'd get a tip?) but decided against it and spit his cum into the drain.

We got dressed, he paid me my other half and asked me if I enjoyed it. "I really did", I said, without lying. Jim was an excellent lover, despite not making me cum (for which he did apologize). He asked if I'd consider doing it again, and I said I'd think about it.

Well, that's about all I have time for right now. If you enjoyed my story, please comment and rate. I will try to get another story up in the next few days, though I'm pretty busy. If you want to know anything specific, feel free to ask in a comment or PM and I'll either try to work my answer in the story or (if it's not interesting or something) PM you back.