This story is a work of fiction.
When I was 21 years old I was living with my parents a couple of miles outside the city. I wanted to work in media but had to get a job to pay my housekeeping, so I took up a waitering gig at an Italian place in the heart of Soho. It wasn't the glamorous start to my career that I'd dreamed of, but there were perks. First, I loved the uniform, a tight, blue velvet shirt and a black apron that hung over the legs. I was also required to have combed, geld hair in very 50s-gent style that I loved.
The other perk, of course, was that I worked in the gayest part of town. I wasn't out to any of my friends or family, but in this new working life I'd made a point of not hiding my interest in boys.
I had been working at the restaurant for about three weeks when a customer came in at the end of the lunchtime rush. He was a tall brunette in his thirties - clean shaven and wearing an office suit. When I gave him his bill he looked at me casually and said "when do you get off?". My arms flared with goosepimples. No one had ever asked me anything quite like that before. The old me would have run a mile, but somehow I was able to catch a sentence in my mouth "er... Now, actually" I sounded like I was offering to take a look at his breakpads! But he smiled and said "good, I'll meet you round the corner in two."
He got up from his seat and left the restaurant. He headed right, and I knew he was aiming for the alley that runs along the side of the building.
I was surprised how excited I was rather than scared. I went out back and put my apron on the side. I took a couple of deep breaths and left through the back exit.
Standing outside the door was the gentleman. He was smoking a cigarette and offered me one. I don't smoke, but it was a naughty kind of day, so I lit up. "You must get this a lot" he said casually, now he sounded like a customer with something that needed looking at! "No, you're my first".
"Well," he said, flicking his cigarette on the floor, "I've not got long". He took me by the hand and led me further down the alley where there was a dumpster. He put his hands on my bottom, pulled me in close and stuck his tongue down my throat. I didn't have to do much, this clearly wasn't his first time. We kissed for a while, him fondling my arse cheeks firmly. Suddenly he stuck a finger in my ass. He was gentle and by no means was it too big - but it was a surprise and I started to panic. But he held me tighter and I remembered that this is the sort of thing I'd fantasised about, so I told myself I'd let him take control.
When the second finger came in I knew where this was leading. He turned me round and leaned me forward, I was conscious that my head was no longer behind the dumpster and I must have looked pretty conspicuous.
I was now full of adrenaline and in a bit of a daze. I knew to expect a pressure on my hole at any second. Before long I was feeling a push and I was trying my best not to moan. I hadn't actually seen his cock at any point and had no idea what to expect - but I tried to prepare for the worst. My hole was stretching to an almost-uncomfortable size - if he got any bigger I would have been in trouble. Luckily, he was consistently girthy - the length though - he seemed to go on for ever. After a few testing pushes he was hitting me further than I'd ever explored on my own. At this point he was holding on to my collar and pounding me hard. Not before long he'd managed to break a button on my shirt.
Mercifully, he eventually pulled out to cum. He turned me around and pushed me on to my knees on the damp floor and he squirted over my face, neck and hair. I couldn't think of anything else to do but open my mouth and hope to catch some - so I did.
His work completed, he invited me up on to my feet and put his hand on my shoulder as if to congratulate me for getting through it. "Did you enjoy that?" I nodded my head and I wiped some of his semen off my lip. He handed me a card "email me, we meet Monday's and Thursday's." He walked off leaving me in an ally with a torn shirt, muddy knees, a sore bottom and jizz in my hair. I had work again in half an hour. On the plus side, tomorrow was Thursday.