Confessions of a Teen Gay Escort Ch. 02

So, in my last story I told you about my first paid date, with a 50-year-old man named Jim. Now, I'm going to tell you a bit more about how I went from one experimental rent boy job to doing it full time, and about the sexual adventures I experienced along the way.

In the months after our first date, Jim called me up a few more times for sex. Usually, I came over to his house for a few hours, where I undressed and he would have me give him massages or blow jobs, and he was usually in the mood to fuck too. He even took the trouble of pleasuring me with his mouth and hands a few times. I started to like our little dates more and more, especially when Jim helped me get off. However, after about five dates, he stopped calling me. Getting impatient after about two weeks without contact, I decided to give him a ring.

Jim was very frank. He told me that he never liked to do it with the same guy for too long (which, of course, is why he hired escorts), and that I was a little 'vanilla' for his tastes. I asked him what else I could do, but he didn't want to tell me because he thought it would freak me out. He said that he might give me call in a few months or so.

It was kind of a blow to my self-esteem in a way, knowing that I wasn't 'good enough' somehow. However, what was worse was that I wasn't getting the extra hundreds of euros from sleeping with Jim. I tried to advertise on Craigslist and in some gay chat rooms, but most of those responding were kind of nasty guys, overweight, ugly and in it for no more than a quick, impersonal lay-and nobody was willing to pay anywhere near what Jim had.

Therefore, I decided to call Jim one more time-to see if he could put me in contact with the escort service he usually used. Jim was nice enough to set up a meeting with the agency's owner, Louis. Louis sent me a short email, telling me to be on time and to dress comfortably.

Louis had a very lavish office in the red light district. He was a tall, talkative but no-nonsense sort of guy, one of those people of whom you feel like you're wasting their time if you don't get to the point quickly. He was friendly though, and gave me a cappuccino as we sat and talked. Louis explained that he was always looking for eager young guys who had their head straight. As I'd originally suspected, drugs were a problem for some boys, and he asked me three times if I was clean, each time more serious than the last. After I assured him that I was, he proceeded to ask me about my sex life. How many guys had I been with, did I do it safely, did I have a boyfriend, all that stuff. He also asked me about which role I usually took in the bedroom.

He asked me if I was comfortable with undressing for him. I took off my jeans and t-shirt, and then my socks and boxers. He walked around me, nodding approvingly, and told me that boys like me were very much in demand with his agency. I'm pretty boyish looking, slight of frame and not blessed/burdened with a lot of body hair, and that 'jailbait' look was very popular according to Louis. He explained how most of his clients were affluent, older gay men who wouldn't otherwise be able to seduce young, attractive boys.

After examining my dick and ass, Louis told me that he would offer me a job, if I was willing to show him my skills. I kinda suspected that he would ask me to perform a sex act, so I was prepared. He was nice about it though, he gave me the choice of either sucking his dick, or showing him on a dildo how good I was. I was tempted to pick the dildo, but I decided it wouldn't hurt to get on Louis' good side straight away.

He locked his office door and unzipped his fly. I got on my knees and carefully grabbed his flaccid member. I licked him slowly and deliberately until he was hard, then I took the head of his cock in my mouth. Every trick I knew, I used on him: teasing it with my tongue, tucking my lips over my teeth and gently 'biting down' for a firmer touch, working his balls with my hand... He was very professional about the whole thing, giving me some tips here and there, but also telling me when I was doing well.

At one point, he stopped me and asked if I could deep throat. I confessed that I couldn't, and he said that that was OK, and that I should continue. He rocked his body along with my motions, like a gentle face fuck, until finally pulling out and shooting his load over my cheeks and face. He gave me some tissues to clear up, and told me that I'd done a good job.

After I cleaned up, Louis said he would give me a try. He offered me a contract where the agency would take 20% of my earnings, in return for setting me up with clients. He said that he would pick out more 'vanilla' customers at first, to ease me in gently. He also told me to come into his office once a week so that he could teach me about how to be a good escort.

Three days later, Louis called me with my first assignment. The client was a kindly old guy, a retired school teacher living in an unassuming apartment in the south of the city. He paid 100 euros for an hour, in which he didn't want anything more than to cuddle and to watch me jack off. I almost didn't believe that doing that fetched me a cool eighty euros.

That sort of client was more common than I'd expected, in fact. A lot of the guys I saw during my first month or so working rarely wanted more than a cuddle, or to see me naked and wanking myself. Only a few times did I have to suck dick, and just one man, a German tourist, fucked me in the ass.

I was making steady money turning about three tricks a week, but not the sort of sums I'd hoped for. Louis was also teaching me a lot about the sex trade during our weekly meetings, and how I could make clients like me more and call me back or extend their time with me. It was mostly little stuff like flirting and dressing seductively, though occasionally he taught me about the different types of client and how best to talk to each sort. He also told me what exercises to do in the gym to keep in shape; I had to focus on cardio and not weights to keep thin without becoming too beefy.

At one of our sessions, I asked him if he had any more better paying assignments. He laughed, and said that he wasn't sure I was ready for that, as the higher paying jobs came from kinkier clients. I said that I was willing to try more if he just gave me a shot. He said he may have something for me-a gay club owner who liked to take escorts out as 'arm candy' at his club nights, then have sex with them afterwards. He told me that some other escorts had complained that he did a lot of coke and was a little rough when it came to sex.

I said I wanted to give it a shot, and Louis told me he'd set something up. He gave me some money to go buy an appropriate outfit: leather pants and a tight shirt. I went shopping right away, and got what I needed pretty quickly: tight black leather pants and a long sleeve t-shirt with a deep V. I have to say, I loved the way leather pants brought out my bubble butt.

I went to meet Rob at his club the following week. Rob was just as described, a very intense guy but affable and charismatic. He was in his late 30s or early 40s, with short greying-dark hair. We had a fun night out dancing and chatting with his friends (I was told not to reveal that I was an escort). He was pretty handsy, slapping my leather-covered ass on the dance floor and occasionally grabbing my crotch.

He did snort a lot of coke, offering me again and again even though I kept declining. At around three o'clock, he took me up to his office. He closed the door, and kissed me roughly. I usually didn't kiss, but he was pretty forceful so I decided to just go with it. He then had me bend over on his red velvet couch, and he barely gave me a 'warm up' before sticking his cock inside. I squirmed at his roughness, but tried to remain professional, as I had been warned. Rob really liked to give it hard, thrusting himself inside me in quick, coke-driven motions and moaning loudly. Occasionally he said things like "Do you like that, you little bitch?" and I feigned pleasure. After about five minutes, he came hard into his condom. I was thrown out pretty unceremoniously afterwards, though quite a bit richer than when I started.

More well-paying but kinky jobs followed. There was one middle aged guy who ordered me as a birthday present for his husband. My instructions were to turn up at their place, take off my clothes in the kitchen and put on an apron over my naked body. I was to serve them food (which had been prepared by the man who hired me), and-at the end of the meal-take off my apron in front of them. The birthday boy was surprised to see me waiting on him, and even more so when his husband told him, as I removed my apron, that I'd been booked for the night and would do anything he wanted. He took full advantage of his 'gift', first making me get under the table and suck him off as the two men finished their cognac, then taking me upstairs where both men gave me an almighty ass pounding.

Well, I'm pretty spent. There's plenty more stories, but you'll just have to wait. Please let me know what you think!