Confessions of a Male Prostitute

It all began in high school, I was young, naïve and broke, I’m about 5’9”, dirty blonde hair, blue eyes, somewhat small in stature. At the time, I barely lived, with my mom in the suburbs, we lived fairly close to the city. My parents were divorced, dad was unemployed and basically estranged, and mom worked two jobs, leaving me alone to raise myself since I was 12 or 13. My teenage years basically sucked. We never had money, good food or clothes, birthdays and holidays were depressing. Friends were tough to come by, as I wasn’t widely accepted.

I would often travel into the city, just to hang, and see what kind of trouble I could find. I did a lot of people watching to take up time, yes I learned a lot about people by their body language, and found I could predict their movement and actions. I particularly spent time along Madison Ave., and “Hotel row”. I hide off to the side of parking lots and watch interactions between the general public and so called “Lot Lizards”. I also fantasized about all the participating parties and actions between them. What really goes on after they leave the parking lot? Sure there was a lot of action that occurred right there in the parking lot, either in a car or back in the bushes. I learned all I knew about sex right there, it became exciting for me and therefore I spent a lot of time right there or roaming the streets. It all began with me fantasizing the underdressed girls, and their suggestive poses as cars or potential clients approached, they were all girl/guy at that point. Then delving deeper, I discovered the trannys and cross dressers, and I studied them too, wondering if they were fooling their male clients, I was like what’s up with that? Lastly I learned what would become my forte,… the guys,… I often thought I could do that, but they never picked up girl clients, something about them made me excited.

One night a car parked about 3 spaces from the curb I was sitting on, I was smoking a used cigarette, I didn’t pay too much attention as most “parker’s” were either staying at the hotel or already picked up their prey, and were nearly going to complete their transaction. After a short while the electric window rolled down, then I heard a guys voice saying “Hey Boy”. I glanced up, realizing he was calling me as no one else was around. I stood up, flipped my cigarette away and approached his door. He asked “you available or waiting for someone”? Taken back I didn’t answer, he took that as available, he said “You can get in, the passenger door is open”. Cautiously I did, I don’t know why, but I did. He was about 40, he asked how old I was, I lied and said 19, and he giggled and pulled out a $20 bill, folded it and handed it to me. Not knowing what to do, and obviously nervous, he pulled a second $20, folded it and passed it to me, I still sat there dumbfounded, then a third, I finally took them, and moved closer, he reached out and touched my crotch. I was harder than hell, as he unzipped me and ogled my young meat, he grabbed my hand and placed it on his already exposed penis under his jacket, and pulled me down shoving it into my mouth, he did all the guiding work, with one hand on my head and another still on my dick. He was watching his hand fondling my dick while I was choking and gagging on his dick. Within minutes without notice he shot his load in my mouth, which I immediately pulled out, spitting every bit I could out of that gross shit, as I climbed out the door running, he yelled “You suck you piece of shit you.” As I ran toward the woods I was trying to tuck my dick back into my pants, and then realized I just made $60. Afterwards I thought I could have done better, and if I could master this, I could make some pretty good money.

Over the next few nights I paid more attention to the guys in the lot. I got closer, I learned how to talk with them, I found the non threatening ones first, soon I knew who I could talk to and hang around with, as they were competitive with each other and some were threatened by my presence. Over the next few nights my mentor was Randy, a twenty something that basically took me under his wing, he told me how to be real careful as even though I was 18, my features made me appear much younger, and that could lead to dangerous situations, as the clients may try to take advantage of me, but he told me I could command top dollar at least for the next few years. He said age would be my enemy, and flaunt my youth for all its worth while I can. All he asked in return was not to step on his territory and let him keep his clients. He told me how he charged, he said they’ll always offer to underpay, unless you set the rules up front. As he explaimed his graduated pay scale.

First he said there’s;

“Touchy-feely”

“Necking and kissing”

“Blow n Go”

“Reciprocated Blow n Go”

“Top”

“Bottom”

“Stay Overnight”

“Fetish” and he advised me to always be cautious with Fetish.

Then he said to

Add per person for more than one.

Deduct for dinner, or repeat customers,

and He explained each of them have 2 rates, one for outdoors or in the car, the other for in a hotel or their home, always be careful of getting in the car and him taking you away from here. Keep that risk factor in play, speaking of risk factor, protect yourself, you got no clue if their going to mug you, beat you, kill you, or give you some disease, and cops,… beware of cops. With that a car pulled up and he jumped in and was gone for the rest of the night.

I gathered information from the girls too, they were less threatened by me as I wasn’t after their clientele. I was gathering plenty of information but not managing to get any clients nor making any money. After several discouraging weeks, I finally managed to get some business, in fact it wasn’t long that I was making quite a bit of money. I was using my scale that I learned from Randy, when I discovered, my youth and people observation skills, I could adjust my prices accordingly. I found most were middle aged, married, frustrated guys just looking to get off, and I could pad the rewards with “adding” the add on’s. I really disliked the overweight, hairy guys, but a buck was a buck, and I just raised the rate to put up with it, in other words, I discounted guys I wanted and overcharged those that turned me off. I learned many satisfying techniques that put me in demand, and learned most of them from my clients, no less, it was ironic they were paying me to learn from themselves, haha. I learned I could spice it up by being more flamboyant and get the richer guys by being more conservative and better dressed, the latter also got me better taken care of with food liquor and drugs.

I was slowest with learning topping and bottoming, I preferred “Doggy style” with the lights out, as I didn’t have to look at those fat ugly hairy guys and I could close my eyes and imagine the man of my dreams doing me, and me doing him. I even added for lights on with “ugly’s”.

I particularly enjoyed picking up guys my own age or younger, and I got to show them a thing or two. I remember a young guy pulling up in what was obviously his dad’s car, and subsequently his first time, I looked in and he just said “Blow job”? I couldn’t believe this hunk of a young buck was willing to, or had to pay for sex, but it was apparent his anonymity was important, probably a closeted high school jock or the like. I offered a huge discount and he quickly squirmed and popped the door lock, practically pulling me in. He pulled into a parking spot leaned over and tried to go to town on me without even putting the car in park. “Hold on there buddy” I said “SLOW DOWN” first “P” is for Park, don’t bring daddy’s car back damaged.  I asked him “You sure you want to do this”? “Yup, you bet” he said, the more I observed this hunk, I broke down and said “Let’s go inside” I sprung for the room myself, this guy was going to cost me, but I decided just then that I was going to be off duty tonight, I knew right then and there I was going further than the blow job that he wanted, little did he know it, but this guy was for me, and tonight he hit the jackpot.

I took him to the room, it started with a kiss, he was shy and somewhat withdrawn, I’m not sure he knew what he was getting into, I told him not to worry about the money, this time it was on the house, he relaxed a bit, as I pulled off his shirt over his head, his slim body, blonde haired, blue eyed, swimmers  build, smooth chest, nice shape and some still developing immature abs, he was another me, I saw my younger self in him. I pushed him into the back of the door shoving my crotch into his, as I pressed his head against the door with a hard lip kiss, his lips were clenched closed, like he was kissing his mother or aunt, I had to force my tongue in-between them and his eyes opened wide with fright. I kept reminding him to relax and I wasn’t going to hurt him.

I directed him toward the bed, I sat him down removed his shoes and socks and I pulled my own shirt off, popped open my belt and pants, then I reached down to undo his. He sat there motionless letting me do everything, as he then said “I was only looking for a Blow Job”, I said “yeah,… OK it is coming but first things first”. I pulled off his pants and his Speedo type underwear, although he did look very hot in them. He’s now naked on the bed still sitting as he watched me continue to undress myself. He watched me as I sensually and slowly exposed my package, and finally his dick went from Woody to fully erect, I could hang a flag from that sucker. I pushed him down to laying position, but his feet were still on the floor. I told him to let me know if anything bothered him and just talk to me if he was at anytime uncomfortable, which seemed to ease his mind and body.

I lay next to him and I finger tickled his chest while I suckled on his nipples, he continued to be somewhat nervous as he stared blankly at the ceiling. I reached over and took his hand and directed it to my manhood which began growing in his hand, he pulled away slightly, finally saying he’s never done any of this before. I told him to relax, it was ok, I would guide him and he will enjoy this first time, I was going to make sure of it.

I guided him to jerk me, as I switched position so he was looking and able to explore my dick as he wished, as I began sucking his head and shaft, I could feel his shaft throbbing as it almost thrashed in my mouth, he began to moan and I made sure I pulled off so as not to make him cum yet. I asked him to lick mine, and gradually tried to get him to suck on it, at which point I had to teach him to keep his teeth out of the way. While he began to master his part of the 69 Blowjob, I continued back onto his dick slowly working my hand from cupping his balls to putting a finger in the crevasse of his ass. I found his hole but only applied slight inward pressure to it, where he really began squirming, I assured him I wouldn’t penetrate him unless he gave me permission, and I felt him relax again.

He seemed to be enjoying my dick, but he often paused I assume because his jaw was getting tired, he only made it ½ way down the shaft but I thought back to my first time and how I wished I had guidance like I was offering. Soon his hips began thrashing and he announced he was Cumming, and I gripped him tighter as he squirted a load or 3 or 4 into my mouth. He fell back in pleasure with a smile on his face, which gave me great satisfaction in achieving my goal, too bad he isn’t paying me tonight I thought. I was still fingering his ass when I asked if he wanted to try anal finger fucking, he reluctantly said yes, and I managed to get one finger painfully in and unfortunately I didn’t have my lube tonight so I stopped.

Afterwards he thanked me and began getting dressed, I told him we had the room all night and he was welcome to stay, he got back into the bed and I spooned him all night and jerked off all over him in the shower the next morning. I managed to give him a soapy finger fuck in the shower which he seemed to enjoy as he jerked off into the drain.

 I offered him a huge discount if he came back for me, so I could show him more next time, he agreed, kissed me and left. I did see him several more times after that, we became good friends, and I never ever did charge him, but he was one of the more pleasurable fucks I experienced in my lifetime, in fact I often think about him while I satisfy myself on slow night.

Over time, overall my Business did very well, and I was always enjoying myself, a teacher once told me, gets a job doing something you love and you’ll never work a day in your life. Well I loved sex, and I got paid for it, yes there was risk, but I was careful or maybe lucky. I got screwed a few times, and in a bad fight another time, but I learned to hold my own. I eventually got bored, I developed a steady base off of repeat customers, we knew each other and they actually paid me to satisfy myself. As I “Aged out”, my rates began to fall and my steady income began to fall by the wayside, Thus memories of Randy’s predictions were coming true. I continued to work but watched as my normal clientele went elsewhere, by 50 I was where I started, poor, and picking up used cigarettes giving $20 blow jobs. My competition became my only friends, as we kept each other company especially on cold and slow nights, sharing used cigarettes and stolen booze, I would do it all again but I should have paid more attention to Randy and I should have saved my money instead of feeding my addictions and wasting it away.