The First of Many
I had worked in a grocery store for a few years. One of my coworkers, Charles (a
manager), was open about being gay and would brag about hosting all male orgies
at his apartment. I had always been intrigued and secretly wanted to participate
in one of these orgies. I had only been with girls up until this point and kept
my desires for male companionship to myself. I had been wearing hose to work for
a while because I liked the feel of it beneath my pants and wanted to be one of
the girls I would always see walking in the skirts and heels with all the men
wanting to fuck them.
One night, my pants leg got stuck a little above my shoe and Charles noticed I
had on hose and no socks. He said, "Oooohhh," and reached out to stroke my leg.
I told him to quit and quickly pushed my pant leg back down. He then said, "I
won't tell anyone, it'll be our little secret." He grinned, and then blew me a
kiss as he walked off. Being a manager, he was responsible for closing the store
but one person had to stay with him until he was done for safety reasons. That
night he told me I was supposed to stay. I was both nervous and excited because
he knew my little secret.
After everyone else had left, he told me he wanted to talk to me. He asked me if
I was wearing hose, thigh highs, or trouser socks. I told him hose and he asked
me why. Since he already knew my secret, I decided to be honest. I told him I
liked the way they felt, the feeling turns me on, that sometimes I liked to
dress up completely, and I had often fantasized about being with a guy. He told
me this was my lucky night, because he had often wanted some of me.
He walked up and kissed me, tongue and all. I instantly became hard, with my
erection straining against my hose. He started undoing my pants and I pulled off
my shirt, so I was standing in the office in nothing but my white pantyhose. I
sat down to watch him strip. He quickly took off all his clothes so his erection
was just bouncing around just inches from my face. I did the only thing that
felt natural; I grabbed it and put my mouth on the tip. I slowly started to lick
all around the shaft before I gave the first blowjob of my life. I didn't know
what I was doing at first, just kept going by when he would moan. I was
caressing his balls with one hand while using the other to guide his cock in and
out of my mouth. After a few minutes of slurping on his cock, he said he was
going to cum. I just looked up and winked at him. Soon after this he began to
shoot his load in my mouth. I backed up so just the tip was in my mouth so that
all his cum would go in my mouth and none would be wasted. When he was done I
opened my mouth to show him what he had produced, then swallowed it all showing
my empty mouth. It tasted both sweet and salty. I knew at that moment I was
hooked and wanted more.
He said it was time to return the favor and reached down, took my cock out of my
hose, and started to give me the best blowjob of my life. I did not last long at
all and soon shot my load into his eager mouth. Instead of swallowing it, he
rose up and kissed me, pushing all my cum into my mouth. I swallowed my cum just
as eagerly as I had his.
By this time he had become hard again and asked if I wanted to try anal. I said
yes before he was done asking. I slipped put and grabbed some KY jelly to lube
up my virgin asshole. When I walked back in, he was sitting and stroking his
rigid cock. I got in a bent over a desk. He spread my ass apart and started to
spread the jelly on my opening. It was cold at first but his fingers felt good
almost instantly. He started by putting on finger up me, then two, and finished
with three. There was a brief pause, then I felt him start to push the tip of
his cock into my hole. It hurt at first and I started to whimper. After a few
small thrusts, he was all the way in. He just stayed there for a few seconds
allowing my ass to adjust, then he started to slowly fuck my ass.
Since he had just cum about twenty minutes ago, he lasted much longer than the
first time. I could hear his balls slapping against me and the sound was oddly a
bigger turn on. I became hard again soon after he began his rhythmic pounding.
After about ten minutes of his fucking my ass, I shot my load all over the desk.
Then I felt one deep final thrust as he shot his second load inside me, this one
deep in my ass. We lay there spent for a few moments, him on to of my bent
frame, with his softening cock slowly sliding out of me. After a couple of
minutes, he stood up and began to get dresses. He tossed me my clothes and said,
"You were pretty good, for a virgin. Maybe you should come to one of my parties
to get some experience."
