In 2002 I was nineteen years old and homeless for a short period. The reasons why I'll not go into.
The weather was bad at the time and finding myself cold tired, I tried to use an all public toilet as a place to sleep. An attendant noticed the cubicle door was locked after a while and I was eventually moved on, but not before I'd pleaded with him to stay. When he asked me if I'd do something for him, so I could sleep in the small room he had there for cleaning stuff and brewing gear, I immediately balked from his suggestive implication.
Two nights later it was cold and very wet. Once again I found myself in the same part of town and once again I tried to sleep in the toilets. This time when the attendant who was in his early fifties, asked me if I'd like to stay in his heated side room, I looked at his growing bulge in his trousers and said yes.
It wasn't easy looking at his greying pubes and flaccid cock, but I knew if I wanted a safe warm place to sleep, I'd have to give him something of what he wanted. Swallowing my pride and his cockhead I began to give the first ever blow job in my life.
His five inch cock wasn't big or thick, but it was very veiny. The feel of it sliding over my tongue almost made me throw up. As my nose buried itself into his pubic hair though, I found his musty scent pleasing and also a sexual turn on. It wasn't long before not only was I enjoying his cock, but I was also beggining to get a hard on myself.
There was no indication he was about to cum, so when he did I was unprepared. Strangely it didn't matter, I'd already begun to take his cock deeper into my mouth so I could continue to get the scent form his balls and pubic area. The added feel of his semen coating my tongue and throat, made my own cock want to explode and I did so inside my jeans.
The sleep I had that night was the first real sleep I'd had for over a fortnight. The second blow job I gave him, before he left to go home to his wife the following morning, was to ensure I had somewhere to stay that night.
The pattern carried on for four more nights. I'd suck his cock dry and he'd let me have some food, a hot drink and a place to sleep.
The night it changed was as I was knocking on his small roomed door. Another younger guy answered the door and asked if I had a problem. Telling him some of the previous five nights, he asked me if I did favours. Looking directly into his eyes I nodded and went to open his trousers. He stopped me and told me it wasn't for him. Letting me into the room he asked me to stay put and wait for him. Twenty minutes later the door opened and in stepped two men. The second attendant stayed outside, but put his round the door and told me I could stay and earn some money, if I looked after the two older men.
Semi naked and having arsehole licked, I had my mouth full with the biggest cock I've ever had in my mouth. It was easilly ten inches long and nearly as thick as a coke can. The first guy I'd sucked off was busily tonging my arse, he'd not lasted long and it was his cum that was coating the big cocked guy long fat dick, as I tried to suck him as deep as I could. When the smaller of the two suggested I get on my knees, I instantly knew they wanted me to take the larger guys cock up my arsehole.
Fearing the worst I told them to fuck off. It wasn't what they wanted to hear and I found myself flat on the floor with a size nine boot pressing down on my face. The floor was cold and it reminded me of sleeping rough outside. It also brought into stark reality, these men were going to have have they wanted whether I liked it or not. Lifting my head slightly, I murmered "Ok".
The pain was like nothing I'd ever experienced before. It felt like my arsehole was on fire. It also felt like it was tareing in two. I was knelt up leaning onto the beaten up arm chair I'd been sleeping on. My arse was in the air and lay under me was the guy with the smaller cock. With his legs apart straddling both of us, was the large cocked man. He was slowly inserting inch by painful inch of his huge cock into my arsehole, as his freind was sucking on my cock as it drooped down below me.
I can't speak for any other male who'd had their arsehole fucked, but for me the first time wasn't in any way pleasurable, other than nearing the end of his brief fucking of my arse, I blew my load filling the other guy mouth. I hadn't even realised I was about to come, let alone that I had an hard on.
Very sore and very unsure of myself, I curled up in a ball on the chair and slept until I was disturbed by the first older attendant the next morning. Telling what had happened he smiled and left me to sleep some more. Later around midday he woke me up, gave me small plastic bag and told me to open it in the cafe across the street.
Sat very tentatively in the cafe, I ordered a drink and then opened the bag. Inside was a roll of bank notes. Unravelling the roll, I discovered there was two hundred pounds.
I had a choice that night, a real choice. Stay in a rented room, or accept the offer from the attendant to make some more money.
Accepting his large throbbing cock up my arsehole the second time was once again painful at first, but this time I was the one who was setting the pace and depth, as I sat on his dick. He was on his own this time and it wasn't in the public toilets, it was in his very plush rented apartment. By the time my own dick was ragingly hard, I was bouncing up and down on his cock with as much pleasure and willingness, as I'd got from anything in my life up to that point.
I stayed living with him for over a month before he went back up north to be with his family. I rented a room nearby for a month and eagerly accepted his offer to share his bed and the money when he returned.
Now eleven years on I'm in a relationship with a woman. She doesn't know about my past life and she never will. It was something that I got through, and meeting the older well endowed man gave the start and confidence to be where I am today.
A happy, reasonably well off guy, who has a wonderful fiancee who loves him.