Roy Takes My Cherry

I remember the first time I ever thought of being of receiving anal. It was
1973 and I was laying in bed with my girlfriend at the time. We had just
had sex and I asked her about having anal sex. She laughed and asked me how
I would feel about having someone shove a big cock up my ass. I told her
that I didn't think that anyone would be interested in fucking my ass and
she blurted out that Roy probably would.

Roy was Karen's brother, 18 years old and what would best be described as a
nerd. In the days of long hair and beards Roy looked like he had just
stepped out of a 1950's farm calendar. As much as I knew him quite well I
had never considered him as a potential sex partner. As the weeks went by
each time we met I began to wonder about him and about being fucked. The
more I wondered the more I wanted to try it.

Roy lived just north of Dartmouth and it was customary that he would drop
by my apartment from time to time on his way home. We would have a few
beers, talk about girls and watch some television. On his next visit I left
out some porn magazines that had a lot of pictures of girls sucking cock
and getting fucked in the ass. As we sipped on our beers and talked, Roy
started to thumb through the magazines in front of him. He soon turned the
conversation around to sex.

What surprised me the most was that he was specific in asking about me and
his sister. Did she suck my cock or take it in the ass? I explained that
she gagged each time I tried to put my cock in her mouth and might take it
in the ass sometime in the future. As we talked about her I could see his
cock hardening in his jeans. I started to describe her great tits and how
she liked fucking and noticed his cock grow rock hard. He told me that he
jerked off a lot but had never had any sex with anyone yet.

I then asked if he would like a blow job from the girl in the magazine,
moving closer to him so I could point out the picture to him. When he said
he would take it from anyone I decided to make a move. I pointedly rubbed
my own hard cock and told him how glad I was his sister was coming over
that evening, then moved my hand over and asked him what he was going to do
as I squeezed the hard lump in his pants.

Roy tensed and sat straight up. At first I thought he was going to bolt
for the door or take a swing at me but as I continued to squeeze his cock
he leaned back on the couch and then turn slightly pointing his cock in my
direction.

Staring at him I rhetorically asked how bad can it be to suck a cock, some
girls seem to love it. I went on to tell him that I had tasted cum before
and it wasn't bad. I could see the shocked look on his face and went on to
explain that some girls love to get eaten after they are fucked and I like
to do that for them. His sister loved it all the time. Roy seemed content
to just lie back there and let me rub his cock at that point, enjoying the
feel of my hand on his crotch.

As I pulled the zipper down on his jeans and opened the button I asked if
he would like to have his cock sucked. Rather than answer he just lifted
his hips, pushing his cock towards me. I open his pants and pulled his
underwear down over his cock, 6" of fat meat, wet and slimy with precum
slid into my hand. I really enjoyed hearing his groan as I stroked his cock
and then leaned over to take the head into my mouth. He lifted his hips and
drove his cock into my mouth, making me swallow most of it. I pushed his
hips back down and started sucking his cock quickly. In a matter of a few
minutes I could feel the head swell, the shaft grow thicker and harder and
the vein start to pulse and taste his cum blast into my mouth. For the
first time it was more cum than I could handle and as much as I swallowed
more dripped out of my mouth and onto my beard. I kept sucking his cock
until I could feel his body collapse back into the cushions.

Roy didn't move as I got up to wash the cum from my face and beard and was
still laying there, eyes closed as I returned and started to wash up his
cock and balls. When he finally open his eyes I asked if he was ok. He
said he was great and had loved it and asked if I liked sucking his cock. I
told him that yes I really liked it too and would do it again whenever he
felt like it, if he felt like it. As he sat up he pointed to some cum that
had dripped onto my shirt and said he would love to have me blow him again.

I stripped off my shirt and went to get another. As I returned to the
living room Roy was still sitting on the couch, leafing through another
magazine, pants still around his ankles, underwear pulled down and his cock
out. He asked me not to put my shirt on and that I take my pants off
too. Once stripped down I sat beside him as he leafed through the
magazine. At first he just absently started stroking my cock slowly,
rubbing his thumb over my head as he did. His own cock started to swell
and jerk back to life so I started to stroke him as he stroked me. He kept
reading his magazine, concentrating on pictures of men taking cocks up the
ass as he did. Finally I asked if he wanted another blow job or to try
something else. My heart was pounding in my chest as he asked if we could
try this, showing me a picture of two guys fucking.

This was what I had wanted all along but at the same time I was worried
about how badly it would hurt and if I would really enjoy it at all. I
hesitated a little than told him we could try, but slowly at first and he
would have to stop anytime it became to uncomfortable for me. I could feel
his cock jerk hard in my hand at that and knew he was excited by the idea
of fucking my ass. I then went into the bathroom and lubed my ass with
vaseline then went out and greased up his hard cock. Explaining that I
wanted to see his face I lay on the floor with my legs up waiting for him.

I held my legs up as Roy started to rub the head of his cock against my
ass, spreading the lube out. The look on his face was amazing, hot pure
lust. Slowly I could feel him press down against me and the head of his
cock force its way into me. The pain I had expected was not there, just a
feeling of being full and I told him to go on, sink his cock into me.

It felt like a baseball bat sliding into my ass, how did 6" of cock feel
like it was sliding up my ass and out of my mouth. It seemed forever before
I felt his balls slide into mine. My ass felt like it was going to
explode. Roy asked how I felt and I told him ok but don't hold back, cum as
soon as he could. Ray slowly started moving his cock a little at a time in
and out of my ass. There was no real pain but a uncomfortable
pressure. Slowly he started moving more until he was slowly pulling his
cock almost out of my ass and then sinking back into me filling me up with
his fat cock.

As I got used to his steady fucking I looked up into his face. He stared
into my eyes and started to pick up speed, thrusting faster and harder into
my ass. I told him how big his cock felt, how he was filling me up till I
felt like I was going to burst. I could feel my ass heat up with the
friction of his cock and see the dazed look in his eyes as he really
started to fuck me hard. His excitement excited me, I wanted him to take
me, fuck me, use me. I beg him to fuck me, cum in me, fill me up.

He slammed his cock deep into my burning ass and started groaning, I could
feel his cock get harder, swell in my ass and then start jerking and
pulsing. I wrapped my legs around him and pulled him deeper into me,
holding him as he shot his cum up my ass. I could feel the burning being
soothed as he came, coating my ass with sperm. Then he started bucking
hard, fucking me as he finished cumming in me.

After cleaning up we discussed our day and agreed that we both really
enjoyed it and wanted to continue. This was to become a weekly event,
sucking Roy's cock and getting fucked and would lead to my most exciting
adventure ever.