Date: Tue, 29 Dec 2015 09:33:18 +0000
From: James
Subject: An Encounter on Lunch Break

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.