Before I get into this story, I would like to cover an administrative detail. Many of my readers have been unable to locate my other stories. The following is a list of the story titles and they can all be found under Prolific Authors / Twonight:
Black Dorm World's Hottest T-Girl The Awakening Star Cruiser The Inmate Shocking Encounter Olympiad Turning 18 The Gamblers The Realtors The Kidnapping The Fluffer First Encounters
Please send feedback to twonight@excite.com. I really enjoy hearing about your first sexual encounter so tell me about it.
Ok, on with the story:
My dad got really mad the day he caught my friend Billy sucking my dick. It didn't help that I was cumming just as he opened the door. Billy turned his head and cum flew everywhere. Billy was no longer allowed to see me after that, but he and I still snuck away and sucked each other when we could.
My Dad got even madder the day he and Mom came home early from dinner and caught me sucking my uncle's dick. Uncle Dan was babysitting me, although I was 15 at the time. Dad was just afraid that I would be having sex with Billy. He would have been even madder if he had known that Uncled Dan had been fucking me for months and had already fucked me earlier in the evening, shooting a hot load up my butt. Uncle Dan was no longer allowed to visit.
The final straw was when I got caught one Sunday being fucked by one of the high school football coaches in the head coach's office. It didn't help that I was wearing stockings and garters or that the coach had a 10-inch dildo up his ass while he fucked me. The fact that we were on the head coach's desk and I had already shot a load all over it didn't help much either. The coach went to jail and my Dad kicked me out for good. I moved in with Uncle Dan briefly, but Dad got him arrested too. When they caught us, I was tied up and Uncle Dan was fucking the shit out of me while dressed in leather.
Before I continue, let me tell you a bit about myself. My name is Chad and I am now 19 years old. I am 5'10" and 170 pounds with a muscular frame, a hot bubble butt, and a thick seven-inch cock. I have long, blond hair and blue eyes and I am smooth and shaven from the neck down.
Now back to the story:
After Dan was taken away, he let me stay in his house, figuring it was the least he could do. The house was paid off, but utilities, food, etc. were going to cost money. I had been expelled, so I figured I had better find a job. I looked everywhere, but the tales of my sexual past had already circulated throughout this moderately-sized town and nobody would hire me. Things went from tight to desperate pretty quickly and I knew that desperate measures were called for. The only real asset I had was my hot body, so I decided to try getting paid for that. I started out going to the two gay bars in town and they quickly barred me from coming in due to my age. I tried waiting outside to catch some horny guys on the way out, but the cops wouldn't let me stand there. I finally heard about guys turning tricks at a particular city park restroom and decided to give it a try.
At first I hung around outside the bathroom but, eventually, I learned that the action was inside. I stood inside the men's room and rubbed my crotch as men came and went. I didn't understand the timing at first. Weekdays were when the married white collar guys came by. Weekday nights were when the kink crowd came in. Weekend days were when the straights brought their kids and weekend nights were when everyone came out. My first pickup was a guy in his mid-40s, a bit heavy with an average cock. He paid me $50 to suck his dick in his car. He gave me $50 extra for swallowing his load. My first paid fuck was a guy in his 30's who came by during the week, took me in a stall, and fucked me hard and fast. I got $100 for that. Things picked up as word got around about me and I was getting fucked regularly after that. I averaged about $400 per day which was more than enough to live comfortably, especially since I didn't have to pay taxes on it. Unfortunately, I also got involved in some of the other things that come with the business. I began to take drugs and got arrested twice for possession. The more drugs I took, the more money I needed and the less the guys wanted to fuck me. When I got arrested for the third time, I thought I was going away to a place where I would get fucked regularly, but not by choice.
I was lying in a holding cell with a mouthful of cum, when I met Bob. Two of my hardcore thug cellmates had held me down and made me suck them off. I hadn't even had time to swallow the second load when I heard my name called. I swallowed the sperm in my mouth and turned to see who was calling me. A man I didn't recognize said, "Hello, my name is Bob. I see by the residue on your face that you are getting acquainted with your cellmates."
"What the fuck do you care?," I snarled.
"Chad, to be honest, I don't care what happens to you. However, I have some clients that would be very happy to get to know you and I like to keep these clients satisfied. Are you interested?"
"If it gets me out of here, I'm interested. What the fuck do I have to do?"
"Well, for starters, stop using the word 'fuck' all the time."
"Ok, what the hell do I have to do?"
He proceeded to explain that a member of the local police force was on his payroll and was always looking for gay prostitutes with a certain appearance. When he saw me, he notified Bob and Bob flew into town. The charges would be dropped if I agreed to participate in Bob's operation. It seems that Bob had a fleet of jets for corporate executives and other high rollers. Bob supplied the jet, the pilots, the catering, and attractive young men and women to cater to te passengers' special needs. All of the jets had a small bedroom, stocked with liquor, porn, condoms, lube, and one or more escorts of whatever sex was requested. He had men and women; blacks, whites, and Asians; and even a hot looking transsexual with a big dick. The escorts were paid a monthly base salary, given a place to live in New York, and extra pay plus tips each time they were requested for a flight. The client could also request that you join them at their hotel and for dinners and parties. Given my current circumstances, it sounded great to me.
The next few weeks were spent getting cleaned up, getting better clothes, and learning how to act in certain social situations. The gay escorts did not get called for as often and they didn't get a lot of social invitations. However, they got great tips, given the concern about discretion. When I finally got my first call, I was extremely nervous. I boarded the plane and was instructed to wait in the bedroom and not come out. It turned out to be much easier than I expected as the guy was friendly and reasonably attractive. He was traveling with a couple of other men whom I did not meet. We were flying to London and he came back to the bedroom, had some wine, instructed me to suck him, then fucked me doggie style and went to sleep. The next morning, he thanked me, gave me $1000 and left. Later that day, he returned and we flew home. He slept most of the way, waking briefly and fucking me again, leaving hot cum deep in my ass. As he left the plane, he slipped me another $1000. This was getting good.
My next gig was a sports executive and his assistant on a trip to Moscow. He was a tall black man and his assistant was also black. He had me sit in the cabin with them, but not speak as they talked business. I watched a movie, then had dinner with them. After dinner and drinks, the flight attendant disappeared behind a door in the front and the executive (Ed) instructed me to suck his dick right there in the cabin. He had a huge cock and it was a real pleasure sucking it. As I sucked him, he described how good it was to his assistant, Bill. Bill was displaying a sizable bulge in his pants at that point and Ed was enjoying watching him squirm. Finally, Ed instructed me to suck Bill's dick. As I took him deep, he moaned with pleasure and Ed began to pull my pants off. When he had me naked, he surprised me by going down on me and sucking my dick like a pro. I was really getting hot. Ed could sense how hot I was getting and, reluctantly, pulled off my cock. He surpised me again by stripping Bill, lubing his tight, ebony ass, and ordering me to put on a condom and fuck him. I was so hard that I had no trouble slipping into Bill's warm asshole. He shuddered and groaned as I began to slowly fuck him. Ed added to my pleasure by slipping his cock up my ass bareback. I had only been the center of a sandwich fuck once before and those guys were so rough that I didn't enjoy it. This was really nice, having my white cock up a hot, black ass while a huge, black fuckstick smoothly stretched my rear passage. Ed's big hands on my waist steadied me as he steadily fucked my ass and forced my own cock to plunge to the depths of Bill's hot tunnel. Bill came first, shooting a huge load all over the cabin floor. Ed followed by filling my ass with hot, creamy sperm. My own semen was soon to follow, but not until Ed pulled off the condom and took my dick in his mouth to catch my load as it sprayed his tonsils. He was like a baby sucking on my cock for nourishment. It was so erotic. We retired to the bed where they both fucked me and shot off in my ass. They made me clean their cocks after they pulled out and we all went to sleep. The next morning, Ed fucked Bill in the ass, then pulled out and began to fuck me. After he came in my ass, he sucked me off and had me suck Bill off.
We stayed in Moscow for four days and I got fucked from one end of our suite to the other. I got to do some sightseeing while they were in meetings, but the highlight of the trip was not Red Square, it was black cylinder, sliding up my ass. By the time we got home, Ed had fucked me twelve times and Bill had fucked me five times. I had swallowed eighteen loads of cum including one from a Russian bellboy who also fucked me while Ed and Bill were out. I had fucked Bill four times and even fucked Ed once. When we got back to New York, Ed tipped me $3000. I should have been paying him.
I have been doing these trips for about a year now and I have socked away about $75,000. I have seen how the elite live and I am constantly amazed at the private fetishes and sexual appetitites of the upper class. I have been on trips with a couple where she had a lesbian and he had me and we all shared the same bed. She cheered me on as I fucked her husband and licked his ass clean after I came in it. I went on a trip to Monte Carlo and got gang banged by a group of Poker buddies who upped my ante and raised me continuously. I had a dick in my mouth or ass the whole trip and often both. They did well at the casino and decided I was good luck, so they kept fucking me at the hotel and all the way back. I was exhausted, but the $5000 tip perked me up. They even took me back in their limo to my apartment. I swallowed a load just as they pulled up in front and dropped me off.
As always, send comments to twonight@excite.com. Check out my other fiction stories, Olympiad, The Gamblers, Black Dorm, The Awakening, The Inmate, Turning 18, The Gambler, The Realtors, The Kidnapping, The Fluffer, First Encounters, and Star Cruiser - and my nonfiction Shocking Encounter and Tess' story - World's Hottest T-Girl.