This is a print version of story My First Time with an Older Man by fionex1 from

My First Time with an Older Man

I was working at a factory in my hometown over the summer. I was a
19-year-old college student at the time and I needed the money. The work
wasn't hard, just boring. Worse yet, my hometown was a fairly small and
un-interesting place as well. My mind wandered a lot during the day and it
always ended up wandering to the same thing. Ever since I had discovered
pornography on the internet, I have been obsessed.

I didn't have my own computer in college so I always had to use someone
else's. During the semester, I would use my roommates. Since our
schedules were different it made it easy to have privacy. He had class in
the morning and I was an afternoon person. Hence, just about every morning
I would wake up and spend about 2 hours searching for sex on the internet
while I pulled on my cock. There were a few close calls. My roommate
would come home early and I would have my pants down and the internet up.
Luckily for me it took him a few seconds to unlock and open the door.
After the first close call I learned to pull my underwear down (or not wear
any), leave my pants on, and play with myself through the zipper.

One day while surfing, I came across a link for a gay pornography site.
Now I had always considered myself a heterosexual male. I always dated
girls and until this point had never seen a picture of any kind of
homosexual sex. Curiosity got the better of me and I clicked. And I
clicked again. And again. And again. I was fascinated. I had never seen
anything so erotic. With every click a new fantasy exploded onto the
screen. My penis was so hard I thought it would pop. Two men kissing.
Two men sitting together. One has his leg crossed over the others. He is
touching his dick. I wanted to touch another mans dick. An older mans
dick. Wait, what was that? An older mans dick? I stopped. I had never
seen two men together before and in a few moments my world had changed.
And I was so sure about it. I even had a preference. I don't know how or
why I had come to the conclusion so fast or with so little thought but I
wanted to play with an older man's dick. My mind was blown. I could
picture him in my mind. He's not just older than me; he's an older man.
Maybe retired. 55+ years old would be ok but I'd love older. 60, 65, 70,
80 years old. The older, the better. Grey haired with a salt and pepper
beard. I like stocky men. A bear type with a big round belly and soft
tits. A hairy belly and some fuzz around his nipples. No tan either. He
should have a fair complexion. I don't think I could kiss him at first. At
least not on the lips. He could kiss my body and suck on my nipples while
I touched him all over. Sliding my hands under his belly. Running my
fingers through his pubic hair. Gently brushing the back of my hand
against his cock. I was hornier than I had ever been in my life.

I kept exploring the website. It was a pay site with lots of good samples.
Every picture I looked at made me more curious and after I searched for a
while I found something that stopped me dead in my tracks. It was two men
playing outside. They had a picnic blanket laid out but were on the grass.
One of the men was laying flat on his back with his legs together. The
second man was sitting on his lap with his knees on the ground and his butt
cheeks squeezed together. He was sitting on his cock. It was the classic
'girl on top position' except there weren't any girls in this picture.
Butt-fucking... butt-fucking... I wanted to be butt-fucked too. By my
older man.

My hand was on my cock. Within moments I was exploding into the piece of
toilet paper I had strategically placed next to the keyboard. I hadn't
shot a load that big since high school. I overshot the TP and a generous
portion of my load ended up on the keyboard. Shit. How the hell do you
get a glob of cum from in the middle of the tiny cracks between the keys?
I had to think fast, my roommate would be home soon. The tissue wouldn't
absorb enough. I could rip out the keys and just wipe but I didn't have
time. I did the only thing I could think of. I put my lips to the
keyboard and started sucking like I had a straw in a milkshake.

The cum slid right out of the keyboard and into my mouth. Delicious.
Hmmm... I like the taste of cum too...

After my discovery I started skipping right past anything with a girl in
it. Men by themselves didn't do anything for me either. I wanted to see
action. The raunchier, the better. Cock sucking, mutual masturbation,
rimming, fingering, fucking, group sex, gangbanging, and even kissing.
When I wasn't in front of the computer, I was fantasizing about it in my
head. Men were fucking in my fantasies all of the time and today at the
factory was no different.

About mid morning I was surprised and elated when my boss asked me to get
in the company car and pick up a part he needed. I had to go to another
town that was about 45 miles from here. I jumped at the chance and got in
the company car. My boss gave me a twenty-dollar bill for lunch and told
me not to hurry.

I was so excited about the break from the monotony that I stopped thinking
about gay sex and started thinking about where I wanted to go for lunch.
That lasted until I came upon something that changed my mind about lunch.
In the distance, about a quarter of a mile up the interstate, I could just
make out a sign on a tall metal post. It said 'ADULT.'

I had seen that sign before and I knew what it meant. The trucker's
delight. It was one of those adult bookstores near the off-ramp of the
interstate. My mind quickly jumped back to a sight I had visited on one of
my web surfing escapades. The sight talked about cruising. It mentioned
the fact that adult bookstores were a great place to find men looking for
random gay sex. I pulled off of the interstate and into the parking lot of
the store. My heart was pounding. Suddenly it was real and I was nervous
as hell. I got out of my car and walked into the store. The clerk was
reading as I came in. He looked up at me but then continued reading his
book. I looked around. Typical adult bookstore. Movies, magazines, and
dildoes on the wall. I had been to one before but had never ventured into
the back room marked 'Arcade.' Today was the day.

As I stared at the doorway I had a weird feeling. I was excited but
sickened all at once. I don't know why. I suppose its the same feeling
anyone gets when they are about to do something that society tells us is
wrong. I imagine you feel the same when you are asked to try pot for the
first time. Your mother told you not to do it but you want to do it really
bad. Just like me and gay sex. Fuck it. I'm going in.

As I stepped through the arcade doorway my heart continued to pound. I
looked around. No one to be seen yet. The room was about big. About half
of the store was the arcade. About 16 booths were lined up in the middle
of the room. I walked forward and made my way past the first pair of
booths. As I rounded the corner, I stopped. A man was standing outside
one of the booths. He appeared to be in his mid-fifties. He was about 5'
10". He had white hair but no beard. No salt and pepper, I thought, but
he does have that middle-aged gut hanging over his belt. I was a little
disappointed but beggars can't be choosers. He looked up and gave me a
nervous smile. I approached him and said hello. He said hi and asked me
if I wanted to share a booth. I said yes. There was no turning back now.

We stepped into the booth together and sat down. He reached across me and
began feeding quarters into the machine. His leg touched mine as a menu
appeared on the screen. My heart jumped and I put my hand on his leg. He
started flipping through the options I asked him what kind of movies he
liked to watch. He exhaled quickly and responded that he liked to watch
the guys. We leaned back as the movie started to play. The opening
credits started to roll as 4 men in a hot tub were relaxing in the
background. As we both stared at the screen I asked him what he liked to
do. He said that he liked to kiss and fondle and whatever happened after
that was up to me. He seemed a little nervous. It made me feel a little
better. He unzipped his pants and pulled them down with his briefs. He
cupped his balls in his hand and began gently pulling on himself. I took
my eyes off of the screen and glanced down at his penis. His cock was
small, only about 4", he was cut, and his little balls were tight against
his body. There was a light coating of white pubic hair surrounding his
manhood. I stood up and pulled my pants around my ankles. My fully erect
shaft staring him in the face. My 6.5" cock is thick and looked even
bigger next to my partners little penis. He looked at it as I sat back
down and took my own circumcised cock in my hand. We gently stroked our
meat as we ran our hands up and down each other's inner thighs. I told him
that I had never done this before. He smiled and said he liked that. He
was relatively inexperienced himself. He was married and had only been
with a few men. He had met them at this bookstore and only went home with
one of them. I asked him if he had ever tried anal. He said that he had
fucked the guy he had went home with but was afraid that he didn't give him
enough cock. I continued to pull on myself with my right hand as I let my
left hand explore his inner thighs. I rubbed his knee. I cupped his
thigh. My hand gently glided over the white hair on his leg and rested in
the crevice between his leg and his balls. He stopped stroking his penis
and put his arm around me. I felt like a son who was learning something
from his father for the first time. I gently began rubbing the back of my
hand on the underside of his balls. I was so hot but I wanted to take it
slow. I opened my hand and placed it around his rod. It felt so good in
my hand. It was warm and hard. I squeezed it and pulled some of his loose
dick-skin up over his little purple mushroom head. He leaned over and
kissed my neck. I continued to explore his parts. Letting my hand caress
and love his manhood. Rubbing his inner thighs. I was in heaven and he
hadn't even touched mine yet.

After a few minutes of exploration he stood up. I looked up at him. I
wasn't sure if he wanted me to such his cock or not. I wanted to buy I
didn't want him to come yet. When he reached his hands out I knew he
wasn't ready to be sucked. I put my hands in his and stood up. As soon as
I was standing he let go and put his arms around my shoulders. I responded
by wrapping my arms around his lower back and letting my hand rest on his
ass. He asked me if I wanted to kiss him. I said I wasn't sure if I was
ready for that. He responded by kissing my neck again and went on to suck
my earlobe. He pulled me closer and our cocks touched for the first time.
It felt beautiful. I slowly rocked my hips against his so that my cock
began to slide through his pubic hair and into his ball-sack. I reached my
right hand lower and cupped his butt while I kept my left arm wrapped
around him. I started exploring his but as I had his groin. My hand
gently rubbing it. His butt was soft. It wasn't hairy or as big as I
would like but I was still in love with it. I slipped my hand into his
crack and began to play. I leaned down a bit and found his butt hole. My
hand brushed his hole and I spread his butt cheeks apart with my fingers.
I switched hands and brought my fingers up to my mouth to wet them. I put
my hand back down and slid my moistened finger back into his crack. With
my lips up to his ear and asked him if I could stick my finger into his
butt hole. He said he didn't want to right now. Disappointed but not
turned off, I continued to play.

He sat back down and I crouched between his knees with my pants around my
ankles. My beautiful white bubble butt was naked, my asshole was exposed
to the air, and my balls were dangling between my legs. I felt free. My
partner leaned back as I nuzzled against his crotch with my face. My nose
rubbed against his tight, little balls and I could smell the musky odor of
man on him. It was a warm smell. A mix of body odor with pre-cum.
Suddenly I wanted to taste him too. I rubbed my cheek against his thighs
and opened my mouth to let my tongue touch his sex for the first time. I
started with his balls. His pubic hair felt good against my lips as began
licking him. I licked his balls while my nose pushed his cock around my
face. I wanted to swallow them. I wanted to feel as much of him inside my
mouth as I could. I opened my mouth and pulled one of his testicles
inside. My mouth was filled up. I pushed it back out and pulled the other
one in. My tongue swirled around his balls and I reached my arms around
him to hold his hips. I played with his balls until I couldn't stand it
any longer and I wrapped my lips around his 4" penis. I took the whole
thing in my mouth and my tongue began playing with it. My mouth was full
of saliva and I let every ounce of it pour over his cock. I wanted it all.
I wanted to taste every square inch of it.

He rubbed my head as I worked on his cock. My cock was throbbing between
my legs, ready to explode. He told me that he came quick and started
moaning quietly. A few moments later he told me he was going to cum. I
don't know why, I was new to all of this, but I wanted to taste his cum and
feel its warmth slide down the back of my throat. I deep-throated him and
spread his ass cheeks apart as his moaning became louder. He grabbed a
handful of my hair and squeezed. I knew what was next. He spurted his
warm gooey cum into my mouth. I let it hit my tongue and fill up my mouth.
Spurt after spurt. It tasted so good. It tasted like him. It was warm,
creamy, and salty. I let it squish around in my mouth as he became
flaccid. I sucked on his limp dick and then swallowed his cum in one gulp.
It slid down my throat and into my stomach and it felt great.

My dick was still rock hard and on the brink of popping. Standing up, I
turned towards the TV screen. I stuck my butt in my sex partner's face as
I leaned over. The 4 guys in the hot tub were fucking and sucking as I
jerked off. My new friend reached between my legs and cupped my balls in
his hand. His lips were all over my ass as I stroked my meat. It didn't
take long before I blew my load all over the TV screen. I pulled slowly as
I was coming. It came out in long, slow squirts. I watched it drip down
the screen and I sat back down. I was spent.

We pulled our pants up in silence. About the time that the reality of the
situation was hitting me, he asked me if we could get together sometime. I
didn't know what to say. I hadn't planned on making any long-term friends
today. I told him that I would try to stop back in see him here at the
store again. I wasn't sure if I wanted to make this a regular thing yet.
I had just had the most amazing orgasm in my life but I couldn't stop
feeling that what I had just done was wrong. I guess feelings of guilt die
hard. We parted ways and I continued my original quest. What I had just
done was over now and I couldn't change it. The feeling of guilt is there
and I can't change that either. It was my first encounter and it wouldn't
be my last. Its funny how quickly those feelings of guilt disappear when
you have your hand on a warm cock. I just can't get those men out of my
head... and I really don't want to.


This is the true story of my first encounter with man-to-man sex. It was
also the first time I have written a story about it. I have recently moved to the Stamford, CT area. I am interested in meeting older men in my area for discrete encounters. I prefer bears but am willing to talk to anyone. Drop me a note and tell me how you liked the story. If you are local, maybe we can create our own story.

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