I was in my senior year of high school, 2003, making me 18 years old,
and my dick was as big as it will ever be. I’ve always had that inner
urge to get with a guy but at this point I’ve only done it “by
myself”.
Who doesn’t love sleepovers, seriously, I would never miss an
opportunity to sleep over at a friend’s house with my good looking
guy friends. I was part of the ‘popular’ group in high school and have
always been able to get with pretty much any girl I wanted, give or
take a few. I was about 6′ with kinda curly brown hair that I flipped
up in the front and, so I hear, gorgeous blue eyes. Ive never been
touched by acne so my face has always been clear. I played lacrosse
from 5th grade up until the time when this happened and we always
had to run a lot for practice, I was more or less in shape but never
one of the big football jocks, but I was toned in my torso with well
defined muscles that cut into my belt line. I’d only ever pushed
myself in lacrosse because I loved just changing clothes in the
locker room with all the guys and those occasions when we showered
together were even more a reason to stay on the team.
The night that this happened started out pretty boring and we were
just driving around going to Quiznos and trying to find a party. The
night started to get late and at 11 we had still not found a party so
we decided that we should buy some beer and somehow sneak it into
Matt’s basement where we could drink then sleepover there. We all
called our parents and got the OK. We went to Giant Eagle and my
friend Derek went in with his fake ID (always a life-saver). He
walked out quickly two minutes later with a 24 case in one hand and
an 18 in the other. We put it in the trunk and headed to my best
friend Matt’s house. By this time it was about 11:45 and we had to
get there by 12 so I was kinda speeding. Matt was the same height as
me with dark blond hair that he always kept pretty short, he had a
kind of hazel eyes and a nice face. We had been best friends since we
were born literally, our mothers had been pregnant together and we
grew up as neighbors and were always hanging out and playin Cowboys
and Indians. We were friends to the point where I had a key to his
house and would often go there and chill until he got there. He
played football but was never so good, but he was in great shape as
you would be if you ran and lifted weights every day. But the thing
that I was attracted to the most were his legs and his ass, he had
the perfect amount of hair on the back of his legs and I was dying to
see how that hair pattern continued up under his boxers.
There were two other guys with us, one named Alex and the other named
Derek. Us four together were known as best friends and whenever one
of us went to a party the others were never far behind. Derek was a
little shorter and had a nice tan, he was skinnier than the rest of
us but had a great body. He had black hair and brown eyes just like
his dad (who happened to be a great looking guy). Alex had dark skin
like a Mexican which we always joked about and a birthmark that
started just above his waistline and continued downward…. He played
lacrosse too but was always too shy to take a shower with us and ran
home to take showers after games and practices. He was a little
flabby but not many people knew how he looked under his shirt, just
his good friends.
We got to Matt’s house and I parked my car on the street and we all
got out. Derek and Alex put the beer by a basement window to be
pulled in later that night. We all went in and Matt’s parents were
already in bed! What luck. We made some pizza and went downstairs.
Derek was the biggest drinker, then Matt, then Me, then Alex. But
tonight Alex had drank even more than Derek and had passed out on
the couch in his clothes before we had even finished our beer. We
finished it a couple hours later and were completely wasted. It was
about 3:15 and we started to get into sleeping positions. Matt slept
on a couch with just a blanket and Alex was still passed out on his
right side, facing the wall, on the other one. Me and Derek slept on
the ground with sleeping bags. I was careful to sleep on the left
side of Derek because his sleeping bag’s zipper was on that side.
Derek, having drunk the second most was passed out sleeping in a
matter of minutes quickly followed by Matt. I tried super hard to
stay awake to do a little ‘exploring’. I waited a couple minutes and
listened to see how hard Derek was breathing. He was breathing
steadily and I was sure he drank a lot so he would be sleeping
soundly. I pulled my upper body out of my sleeping bag and moved my
hands over to unzip Derek’s. I started to unzip it and felt the warm
air come out from inside. I got it unzipped down to his knees and
started to move my hands inside his sleeping bag. I had done this a
few times before but only ever felt legs and stuff on drunk nights
but lucky for me we had all decided to sleep in boxers this night,
except Alex, that would be a task. I felt Derek’s hairy legs with the
back of my hand and started to push up his boxers. My dick started to
get hard immediately and I let it pop out of my boxers to relieve the
tension. I moved my hand to Derek’s inner thigh and put it up into
his boxers, I felt his balls with my fingers and then put his limp 4
and a half inch dick into my hand, I though about jacking myself
right then but thought I could get more out of this, after all there
were two other drunk friends in the room. I started to jack him off
even though the angle was weird and I felt him getting hard in my
hand, god and his dick was so hot. I started jacking myself with my
other hand and then right before I was going to squirt, he rustled
and turned his body over onto his side. God! Just one more second and
I would have had it, but my boner died quickly thinking that Derek
had caught me touching him while he was sleeping. Luckily, he didn’t
say anything so i stayed where I was until I was sure that he was
sleeping again.
I heard his breathing get steady again and started moving over to
Matt. He was in a tight undershirt and boxers but he had thrown his
blanket off of him while he was sleeping…less work for me. There
was a little light from the computer on the other side of the room
and I could see Matt’s well toned body in the dim lighting. His
boxers were down a little low and I could see his happy trail
starting to widen into his pubes, I also saw his love handles fading
down into his legs which is my favorite part of a guys body. I took a
different approach with Matt when I noticed that the hole in the
front of his boxers was almost wide open! I started to put my fingers
in the hole and I felt his pubes touching my hands and tried to find
the base of his shaft, his dick was flopped on its back pointing
towards his head, I grabbed it lightly and let it lay down outside
his boxers. I looked at it intensely and saw the ‘V’ on the back of
it’s head. I gave it a little lick and moved my tongue to the base of
his dick. Then I moved to his balls, which were bigger than Derek’s
were but not as hairy, I pulled them out one by one so that his cock
and nuts were just sitting out in the open air. I got up off my side
and got on my knees. Matt was still breathing good so I stood up and
went to get a flashlight from upstairs, it seemed like it took
forever but thank god I was so familiar with Matt’s house. I came
slowly back down the basement steps and went over to Matt, I turned
on the flashlight and saw that he had turned himself over and was
laying on top of his dick. I touched his ass and he stirred a little
so I dove to my sleeping back and pretended to be asleep.
I considered that a lost cause and waited about ten minutes, which
went by super slowly. I climbed over Derek and moved toward Alex, my
last chance for a good jack off session. It was promising seeing how
he was completely passed out, and earlier that night we were hitting
him with pillows and he wasn’t waking up. I went straight to his belt
not wasting a minute, by now it was 4:25 which I couldn’t believe! I
undid his belt and then the button and zipper on his pants. I pulled
his pants down to the middle of his thighs and then slowly pulled
down the side of his boxers that he wasn’t laying on. I grabbed the
flashlight from the floor nearby and turned it on, being careful not
to let too much light get out. I shined it on his crotch and saw that
beautiful birthmark, it went all the way down into his pubes and I
touched it and caressed his pubes. I started to move my face nearer
when I realized how close his ass was to me. I put my hand between my
legs to warm it up for a second so I wouldn’t wake him up. Then I
slipped my left hand under his boxers, stretching the elastic but not
too much, and felt his flat back subtly part and turn into two plump
cheeks. I kept my hand on the crack and let my middle finger slide
thought the twisted hair finally to come to his hole. I thought for
a minute with my finger touching his hole if I should try to slip it
in. I decided yes and pulled my hand out. I put my finger in my mouth
and got a little taste of his ass, which I thought would gross me out
but turned out to be a huge turn on. After my finger was totally wet
I put my hand back in and found his hole again. I started to put my
middle finger in and was so afraid that he was going to wake up, it
slowly eased in to the first knuckle. Then I moved my hand in a
little more and put my finger in to the second knuckle. I could feel
his warm insides on my finger and moved it around a little. It was a
texture like I had never felt before in my life. I pulled down my
boxers and started to feel my huge boner, the biggest I’d ever had,
and let my finger slip in his hot asshole a centimeter past the big
knuckle. I was so horny and started to jack off real fast, I started
to pump my finger in and out of his asshole, then I tried to get two
fingers in and he stirred, but I kept jacking. I couldn’t lose it
again. I pulled my finger out and stopped with both hands for a
second, I listened, and realized that he was asleep again already! I
used both hands very slowly to turn him over and at the same time
pulling his boxers lower, exposing him down to under his balls. I now
understood why he never wanted to shower with us after lacrosse, his
dick was bigger limp than I had ever seen in my life, it was about 6
and a half inches, limp. While one my knees staring with my dick
resting on the couch, his left hand flopped down and laid directly
on top of my exposed boner. I’d never felt that hot in my life. I
turned his hand a little and put my huge boner inside it. My dick was
wider than normal because I had wanked it so much that night. I
closed his fingers and started to pump with my body as if I was
masturbating myself. I naturally started to bend over with the motion
and then crouched myself closer to his dick. I grabbed his dick and
let it limply sit in my mouth. It immediately started to get bigger
and was starting to harden, I was 30 seconds from an orgasm and I had
a guy jacking me off and his dick was in my mouth! I started to suck
him hard and I couldn’t beleive he wasn’t waking up, I was ten seconds
away when i tasted his precum and I was about to blow the biggest
load of my life, I kept pumping with my dick and pulled my mouth away
with the taste of his cum in my mouth! I had just got a guy to cum in
my mouth, but that wasn’t the situation at hand…where was I going to
put all this cum that was seconds from coming out? Then I knew, and
you would have too. I thought to myself…Is he drunk enough?…. Of
course he is. So I quickly pulled up his hip with my left hand
putting him on his side again and laying him against the back of the
couch. I pulled up his left ass cheek and put my knob against his
hole. This was the moment of truth, I shoved with all my might and
got three fourths of my 7 and a half inch, unusually wide cocking his
virgin asshole. He stirred but it was too late, I was already
unloading, and pulse after pulse of my hot cum was streaming into his
asshole. Six or seven huge loads entered and he stirred again. I
pulled out and dove over to my bed to hear him stirring even more. He
moved around for about a minute and then stayed still. I waited ten
minutes and knew that if I didn’t put his clothes on I might get
caught. I moved over and started to pull up his clothes when I
realized this once in a lifetime opportunity. I ran to the computer
and got Matt’s digital camera, I ran back and started snapping
picture after picture, I must have taken 25, including his bright red
asshole with my cum all over it. I regretfully put his clothes back
on and sent the pictures to my email and erased them off the camera.
There was no way I was gunna get caught. I went back to my bed and by
this time it was 5:30 so I fell right asleep but couldn’t help
thinking about all that had just happened.
The next morning we all woke up and had blueberry pancakes that
Matt’s mom made for us. Alex was quiet not saying a word but when
Matt’s mom left the room, we asked him if he had a hangover. He said
he had a terrible one and that he was sore too. To that I said, “What
do you mean?”
“I must have fell down last night. Dude, I think I broke my fucking
tailbone, like seriously.” He responded painfully.
“Yeah dude you did, you ate shit tryin’ to come down the stairs
fast …remember that Matt?” I said, covering up quickly.
“Yeah I think so…,” Matt lied, just trying to end the conversation,
realizing that his head hurt more the more he talked.
“Damn,” Alex threw in, chewing his pancake with tremendous pain, “we
gotta do this again…”
“Absolutely, ” agreed Matt and Derek in unison.
“No Doubt,” I said, forgetting about my hangover, daydreaming of the
next sleepover we would surely have.
The End
