Date: Fri, 8 Jun 2001 12:00:08 -0700
From: Ronny Wernick <rwernick@jackinchat.com>
Subject: BOARDING SCHOOL ROOMMATE

I attended boarding school in New England while in my teens.  When I was
14, my roommate dropped out unexpectedly only a day or two after the term
began.  A new kid named Bobby showed up, and the only open room was mine,
so the administrator assigned him to be my new roommate.  It was an unusual
assignment, since the new boy was only just 12, and they normally kept
roommates the same age.  The administrator apologized, but I said it was
OK; I could live with it.  Besides, being older, I could help get him
settled in.

Something about him attracted me as soon as we first met.  He was tall for
his age, but thin.  He had sandy blond hair, cut medium length, and lively
blue eyes that sparkled when he talked to me.  His face was round, with
high cheekbones and a button nose.  He had on shorts that showed his legs
to be long and lanky, with a shape like a young girl.  He wore a loose polo
shirt open modestly at the neck, and the bone and muscle structure of his
neck and collarbone were well defined.

The first night as we got ready for bed, he put on shortie PJs.  The top
was a pull-over, with a V-neck, and the shorts were quite short, with two
snaps at the fly.  They were thin cotton, and looked very soft.  As he
pulled off his boxers to put his PJs on, I noticed he wasn't circumcised,
which interested me since all my friends were.  I don't think I'd ever seen
anyone uncircumcised up close before.  His penis was a lot smaller than
mine, but pretty good sized for his age.  Instead of hanging limply, it
pointed out from his body at about a 45 degree angle.  The foreskin over
the head made it look a little longer than it really was.  His balls hung
freely, unlike most kids his age whose balls snugged up into their crotch.

I don't know why I was so intrigued, but I kept thinking about how cute he
was, and how I wanted to see more of him.

It was a fairly warm night, so just before we hopped into bed, he pulled
his top off and pulled just a sheet over himself.  Before long he had
pulled the sheet back so it just covered his lower body, and soon it was
only over his feet.  He fell asleep quickly.

 I lay there looking at Bobby in the gentle light coming in the window from
the streetlight, as his breathing settled into a slow, deep, rhythm.  He
was out cold.  Must have had a long, tiring day.  His body was perfect.
Not an ounce of fat on him.  His stomach muscles defined a clear V as they
descended toward his crotch, which was enticingly hidden by the thin cotton
of his shorts.  I could see a small mound where his penis would be.  I
longed to look more closely.

Carefully and slowly, I got out of bed.  My heart was in my throat.  I had
never done anything like this.  I tiptoed to the side of Bobby's bed and
got down on my knees.  He was laying flat on his back, arms and legs
splayed across the bed, obviously in a deep sleep.  Holding my breath, I
reached out and gently placed my palm flat over his crotch, and could feel
his firm little penis laying over to one side.  I was really excited; my
heart pounding and my own penis stiff.

He didn't react at all, so I pressed a little harder.  I could feel the
ridge of his penis head under his foreskin, and his ball sack.  With still
no reaction, I slowly removed my hand and felt for the snap in the middle
of his shorts.  I carefully pulled it apart, hoping the sudden snap
wouldn't wake him.  It didn't.  That open, I had almost a full six inch
opening from the bottom of the fly to the top snap.  With the fingers on
one hand, I gently pulled the fly apart.  His penis was way at the bottom
of the fly, so I pulled down on his shorts a bit to shift them, and the
waistband slid easily down his flat stomach.

There it was!  His penis and crotch laid out for me to see.  It was really
neat looking.  I gently gripped his penis, and it was warm and firm.  I
pulled gently, and his foreskin rolled back, slowly revealing the head,
which was purple and wet looking.  I pulled it back and forth a couple of
times, and felt his ball sack, and was so turned on I had to pull my own
penis out the fly of my boxers, and began to rub it.

Bobby's penis began to harden.  Hard, the head was just visible as it
pulled his foreskin partly back.  I continued to play with it, and as it
got harder I could feel the blood veins, and it felt neat to feel how
smoothly the foreskin pulled back and forth.

When it was fully hard, Bobby shifted a little.  Afraid he'd wake up, I let
go and pulled his fly closed again.  I didn't dare snap it for fear it
would wake him.  I hustled back to my own bed, pulling my boxers down.  I
lay there jacking off, and was rewarded by the sight of Bobby's fly falling
open and his hard penis sticking out, with the foreskin pulled back just
enough to see the tip of the head.  As his penis slowly softened and the
head disappeared under his foreskin, I jacked off wildly, and spurted all
over myself for a very gratifying orgasm.  Wow, that was neat.

The next morning when we got up, we both headed for the showers.  I noticed
Bobby didn't seem at all self conscious, undressing and showering nude
without trying to hide himself.  I of course enjoyed sneaking peeks at him,
and particularly enjoyed watching as he pulled his foreskin back to wash
under it.  His penis head was purple and raw looking; it looked very
sensitive.

That night, Bobby got into his PJ shorts like the night before, but didn't
bother with his top.  When we went to bed, I settled down and pretended to
fall asleep quickly, hoping Bobby would, too, so I could touch him again
like I'd done before.  But before long, I was surprised to hear a soft
snapping sound, and some movement from his bed.  I could just barely see
Bobby out of the corner of my eye, and was amazed to see he was playing
with his penis, with his PJs unsnapped and laying open.  He must have
thought I was sound asleep.  He was slowly sliding his foreskin back and
forth, clearly enjoying it.

I got an immediate hardon, and had a hard time resisting reaching down for
it.  It stood up in my boxers like a tent pole, pushing up the sheet over
my crotch.  If Bobby looked over, I'm sure he could have seen it.

He kept the rubbing up for a couple of minutes, then started to speed up.
It didn't take long for him to get tense looking, and his hand was flying
up and down with abandon.  Suddenly he stopped, holding tight, and I saw a
jet of very thin, watery semen launch out of the end of his penis and land
on his chest.  He moved his hand slightly, keeping the head exposed, and
shot several more jets, each one going a little less far than the ones
before.  Soon, it was just dribbling out, and Bobby lay panting.

He lay there like that for two or three minutes, then I heard the soft
rustle of a tissue, and could see him wiping himself off.  He had the
tissues right at hand, so obviously he had planned this well in advance;
his jacking off session wasn't on the spur of the moment.  For some reason
that excited me.

There was more movement as Bobby pulled his shorts back up and snapped
them, then he settled back to go to sleep.  It wasn't long before he was
breathing slow and deep, sound asleep.  I waited for another 15 minutes or
so to make sure he was really out, then sneaked over to his bed like I'd
done the night before.  This time, though, I could see a little wet spot on
the front of Bobby's shorts, obviously dribble from the end of his penis; a
little leftover semen.  I opened his shorts like the night before, and when
I pulled his foreskin back and felt the end of his penis, it was all wet
and sticky.  It was more than a dribble; his foreskin was full of it.  I
thought I'd cum right then, it was so exciting.  I wiped my finger in it
and sniffed it; it was a strong pungent smell.  Then I tasted it.  It was
salty and sweet.  Holding his penis like that, I couldn't help jacking off,
and went to it right there at his side.  His penis got a little hard, but
not as hard as the night before.  It didn't take long for me to cum, and I
shot all over the side of Bobby's bed, making a huge mess.

After I recovered, I let go, and went to get some tissue of my own to clean
up with.

The next morning, I noticed Bobby's tissue just laying in the trash can.  I
hung back a bit when he went out, and substituted my own for his, pocketing
his wet mass of tissue.  All day I could feel it in my pocket, still damp,
and when I could, I pulled it out and sniffed it's strong aroma.  After
lunch I sneaked off to the bathroom and jacked off, holding the tissue to
my nose.

That night, I wondered what would happen.  Bobby didn't jack off, and when
he was obviously asleep, I sneaked over.  This time the sheet covered him
from the waist down, so I gently began to pull it lower.  To my surprise,
he didn't have his PJs on at all; he must have slipped them off after he
got into bed.  He was totally naked.  I didn't know what that meant, but
took it as an opportunity to feel around his hips, thighs, and crotch
without anything to encumber me.  It was really neat.  When I started to
play with his penis seriously, it got hard like the first night.  I
couldn't help but pull the foreskin back and forth like I'd seen Bobby do
the night before; it was really exciting.  I guess I got a little careless,
because I didn't notice any signs of Bobby waking up, but suddenly, he
said, "That feels good."

I about jumped out of my boxers, and immediately dropped his penis.  Bobby
smiled and said, "That's OK; my brother used to do that to me all the time.
Wanna keep doing it?"

"Yeah," I said in a shaky voice.  I grabbed his penis again, and continued
to jack him off.  Bobby lay there with his eyes closed, and when he started
cumming, gave a grunt, and he shook.  His semen shot out all over him, and
I could feel his penis throb in my hand.  I continued to hold on as the
throbbing died off, and let go when it started to go soft.

I went back to my bed sheepishly, not knowing what to do now.  Bobby
cleaned up with some tissue, then asked, "Want me to do you?"

"Yeah," I said eagerly, thankful he wasn't mad at me.

Bobby came over to my bed, still naked.  I pulled my boxers down, and he
gripped my penis.  He seemed to have a good feel for it.  "You do this to
your brother?"

"Yeah.  He's 16 now.  He started jacking me off when I was 10, and I did it
to him, too.  Kinda neat, but I've never done it with anyone else.  Been
too afraid."

He jacked me off expertly, and I had a wonderful orgasm, pumping semen all
over myself.

After I calmed down, I asked him why he had taken his PJs off before
falling asleep.

"I usually sleep naked when I'm alone at home.  When I found one of the
snaps undone two mornings in a row, I figured you were doing what my
brother used to do to me.  I thought I'd make it easier for you."  With
that he gave me one of his priceless, cheery grins.  Wiseass!

I asked him, "How did you and your brother start doing that together?"

"When I was little, my brother used to feel me at night like you did, but I
pretended I was sleeping.  He'd do it for a while, then jack off.  Usually
he'd do it lying beside me.  He'd be feeling me with one hand, and jacking
off with the other.  He'd be so busy with what he was doing that he
wouldn't notice that I was watching him. I was always fascinated by the
white stuff that came out.."

"Then one night, after he went back to his own bed, I decided to try it on
myself, so I lay there and rubbed my penis the way he had done.  It took a
while, but suddenly I felt why he did it.  It felt like I was exploding.
It was great!"  Nothing came out, though.

"I started doing it almost every night, after my brother did it beside me.
Then one night he woke up and caught me.  I was really embarrassed, but
don't know why, since he did it to himself all the time.  He asked if I
wanted him to do it to me, and I said yes, so he came over to my bed and
jacked me off."

"The next night, before either of us fell asleep, he asked if I wanted him
to do it again, and I said yes, so he came over to my bed.  We both
stripped naked, and he felt me for a while, then jacked me off.  After he
was done, he did it to himself, and for the first time, I could watch
openly."

"We did that several times before I asked if I could do it to him.  From
then on we jacked each other off almost every night, and sometimes played
around with each other on weekends if our parents were away.  But we were
always very secretive about it.  I didn't even know for sure that other
boys did that, until I felt you playing with me tonight.  It's kind of a
relief to know."

His story was getting me turned on again, and I could see he had an
erection again, too.  "Looks like we need to try that again!" I said.

"Yeah," he said with a grin.  And we did.  After we were done and cleaned
up, Bobby fell asleep beside me in my bed, so I just let him stay, and we
slept together naked, covered only with a sheet.

The next morning we woke up, and both felt a little sheepish having slept
together like that.  We played with each other for a little while, but had
to get going and didn't have time to get serious.  I looked forward to
bedtime all day!