Date: Sat, 22 Nov 2008 15:38:13 -0600
From: Benjamin Winters <benwin83@gmail.com>
Subject: Truth or Dare with J

Comments to: benwin83@gmail.com

LEGAL: If you're under 18, don't read this. yada, yada, yada... Enjoy!

TRUTH OR DARE WITH J
By Benjamin Winters

In my little neighborhood, in my little town, there were many boys
around my age. By the time I graduated from highschool and left for
college, I had "messed" around with most of them. Yeah, I was a
little slut. And quite happy about that!

Most of my experiences were just experimenting, that "I'll show you
mine if you show my yours" game. But, I knew I was gay pretty early
because I always wanted to take the game just a little bit further
than the rest...ok, sometimes a lot further. :)

But there were a few boys that wanted to keep going, and this story
is about my favorite...my fondest memory...my first real boy/boy
kiss...my Truth or Dare game with J.

J lived across the street with his parents, brother, and two sisters. I
was 13, 5'4", 100 lbs or so, brown haired and green-eyed, and,
while he was two years behind me in school, he was only about 18
months younger than me, and pretty shy, but a cute blond haired,
blue-eyed boy of 11, when the youthful games took quite an
unexpected turn.

We had played truth or dare before. We all had. We'd looked at each
other's wieners, gotten naked, and even put our little dicks in each
other's mouths. But it was all pretty innocent...until my parents
went out of town and I got to stay with J for a week.

J's family had a pool, with an enclosed hot tub, and the
neighborhood kids all flocked to it. I remember times of sitting in
the hot tub and often pulling off our swim trunks, excited at being
naked in the warm water. Plus, it gave me a great opportunity to see
the other boys naked!

As expected, the first night I stayed with him, we got in the pool as
soon as I got over there. After swimming for a while, J and I headed
to the hot tub.

Now, as I said before, I had "experimented" with most of the
neighbor boys, so I was well aware of my dick and what it did, other
than pee. I had discovered masturbation, quite accidentally, at
around five or six years old when I was laying on my stomach in the
bath tub. Mom had left me alone, and I was sliding around on my
belly when I noticed my dick felt pretty good. So, I just kept going.

As I moved faster and faster, it started feeling REALLY good. Pretty
soon, this feeling came upon me that I had never felt before and I
had my first orgasm. Obviously, nothing came out (I was five!), but I
had just discovered the greatest thing in the world!! And I was
hooked for life!

I remember at about age seven, my mother coming into the
bathroom while I was going at it. Not knowing what to do, I flipped
over on my back, laid back in the water, and asked if I could wash
my hair. Not sure why I did that, but it seemed like the obvious
diversion at the time. So, there I was with my little red boner
sticking up in the air and my mom just looking at me. She told me I
shouldn't be doing that, and walked out. (the parents were never
good with the birds and the bees stuff) Anyway, back to the story.

At 13 years old, I was in the midst of puberty and was completely
hairless, except for a small patch of wispy hairs above my growing
dick.  With the growth and the hair, came two things. The first was
that I came when I practiced my now frequent masturbation,
causing me to go through Kleenex at an astounding rate. (I had
learned about cum from the older neighbor boys, but that's another
story) The other phenomenon was that I was hard and horny ALL
THE TIME!!! This first night at J's was no exception.

As soon as we got in the hot tub, and locked the door, I pulled off
my trunks. I remember my little 5-incher being hard as a rock. As J
and I were talking, I stood up and waved my dick at him and quickly
sunk back in the water. We'd done this before, so it really wasn't a
big deal. However, this time, J stuck out his foot and put it up
against my boner. Holy shit! That felt great! I grabbed his foot and
humped my dick against it for a second, until he pulled it back.

As we continued talking, J said, "I wonder what it's like to suck a
dick?" Ok, I was young, but I knew we had just crossed into new
territory, and that I would need to guide this carefully, because I
had been trying to figure out how I was going to suck his. (I was
such a little slut!!) I replied that it was just like sucking on your
finger and no big deal.

Then, J took the swim mask on the side of the hot tub, and sunk
under the water. I could clearly see him looking at my dick, so I
grabbed it and waved it under the water at him.

When he came up, he was smiling and sat back down. He then
started talking about how he and his 8yo sister had played Truth or
Dare with another neighborhood boy, and about how they had
gotten naked and felt each other up. If I wasn't hard before, I could
have cut glass at this point, because I could see where this was
going.

I suggested that we ought to play with his sister, as well. He
thought that was a good idea, so we put our trunks back on and
headed inside.

When we got inside, we went and found her and said that we were
going to play T&D in their room and did she want to play. He shared
a room with his little sister, and since all of her clothes were in the
room, it was natural that she would be in there.

We all went into their room to change our clothes. I put on jeans
and no shirt, J was in just shorts, and his sister was in shorts and a
shirt. There were two single beds and a chair in the corner. I sat on
one bed, J on the other, and his sister on the chair.

So, there we were, two boys, one 13 and one 11, and an 8yo girl.
Although I really had no interest in his sister, and I really don't
think he did either, having her there made it ok for us to play, for
some reason.

We all knew why we were there, so we skipped the "truths" and went
straight to the dares.

"Take off your jeans and do 10 jumping jacks in your underwear.
Get naked and run around the room. Stay in your underwear for the
rest of the game. Etc." Then, the one I was waiting for.

J looked at me and said, "I dare you to feel me up for 10 seconds."
I'll never forget the next 10 seconds, or the hours and hours after
that first touch.

J was sitting on his bed in his cute white briefs, with a prominent
bulge in the front. Now, I had not really seen his dick lately so,
when he pulled it out of his briefs, I was taken aback. Not only was
he hard, his dick was a good five inches and he had more hair than I
did. He was 11 years old!! And was already more into puberty than I
was.

I remember reaching out and putting my hand on his warm hard
dick. It felt great! After my 10 seconds, he said, "that's good" and I
reluctantly pulled my hand away. For several more dares, we all
took turns feeling each other.

J then turned to me and said, "it's ok if A (his sister) dares me to
suck your dick." (faint) And I said that was ok with me too.

So, we talked to his sister and told her that it was ok. She didn't
really get it. As we were trying to explain, his mother knocked on
the door, asking what we were doing and why we had locked the
door.

Shit!!! J and I grabbed our pants and put them back on and A ran
into the closet where her dresser was. I laid on the bed, on my
stomach because I still had a hard on, and J unlocked the door.

She asked what was going on and we just told her that A had to get
her clothes and I must have accidentally locked the door. Not sure
she bought it, but she just told us it was time to go to bed.

Well, that's the story....just kidding. (I know, pretty mean, huh?)

After A left, and J and I were getting ready for bed, I asked if he
wanted to keep playing. He said he did and I asked how "nasty" he
wanted to get. All he said was, "all the way". (swoon)

We both stripped down to our white briefs and walked down the hall
to the bathroom to brush our teeth and pee. He told me to make
sure that I wiped the pee off my dick cause he didn't want it in his
mouth. (swoon, again)

After our ablutions, we returned to his room, shut the door, and
turned off the light.

As we sat on our beds, we could clearly see each other in the
moonlight filtering through his second story window. We were both
excited and hard.

We started the game again with feeling each other up. Tired of
pulling our briefs off and putting them back on each time, we
decided to just stay naked.

So, there we were, two young boys, naked, hard, and horny, and
knowing what was next. Then, it came, he dared me to suck his
dick for 20 seconds.

I leaned towards him and took his dick into my mouth for the first
time. I will never forget the feel, the texture, the shape, and, most
of all, the smell. It was wonderful! A mixture of boy, chlorine, and,
for some reason, wood smoke. Through the years, I have
occasionally come across this same smell, and I get an instant hard
on.

I ran my tongue up his dick and took the head in my mouth. As I
bobbed up and down, I couldn't believe I was getting to do this.
After a very short 20 seconds, he pushed my head off and said,
"that's good". Looking back, I remember him doing that several
times - pushing my hand or mouth off and saying "that's good". I
have often wondered if he was about to cum and didn't want to yet,
or just wanted to get to the next thing. Of course, I then dared him
to suck mine.

After sucking each other several times, he said, "I dare you to suck
me while I suck you." What?!?!? Isn't a dare supposed to make the
OTHER guy do something??

Luckily, I had actually 69ed with another friend (again, another
story), so I knew the right position and quickly pushed him on his
back and climbed on the bed. As I straddled his head, me on top
and him on bottom, he took my dick in his mouth and I reached out
and took hold of his and sunk my mouth on it. I began to thrust
slowly into his mouth while moving up and down on his dick. It was
tremendous! We went at it for a minute or so, and I then rolled off
him and sat back down on my bed.

He then said, "I dare you to kiss me." Damn! I leaned over and
pecked him on the lips. I dared him back and he leaned over and
pecked me on the lips.

Now, I had never kissed a boy. I had kissed girls, a lot, (I was an
equal opportunity slut, at that point in my life) so I was very familiar
with kissing, and frenching, and what you can do with a tongue,
and how it works. But I hadn't done this with any of the other boys
that I had fooled around with, so I didn't know where this was
heading.

(Another funny thing I look back on, I turned out gay and he ended
up married with kids, but he was the one that initiated this whole
thing. He was the one that upped each dare. hmmmm)

Then, the most momentous moment of the game, and the one I
remember so vividly that I can't believe it happened over 30 years
ago.

I was sitting on my bed, naked and hard, he was sitting on his, in
the same state. He looked through the moonlight at me. He didn't
dare, he was no longer playing a game. He said in a soft whisper,
"let's start making out and then lay down and start frenching."

I got up from my bed, walked the four feet to his, sat down beside
him, put my arm around him, turned my head and softly pressed
my lips to his. It was heaven. There were no restrictions, there was
no "20 seconds", we were just kissing.

As we began to kiss, he placed his hand on my chest and pushed
me back onto his bed, never breaking contact with my lips.

As my head touched his pillow, we both opened our mouths and
touched our tongues together for the first time. It was one of the
most amazing things I have ever felt, and is probably why kissing is
still my favorite part of sex.

Our kissing became more frantic as our lust consumed us, and he
moved his naked body onto mine. Our bare dicks made contact and
we began to frantically thrust against each other.

We humped and kissed for several minutes before rolling over and,
still "frenching", laying side-by-side.

With our hands caressing each other's dick and balls, we broke the
kiss and I began kissing down his chest. There would be no more
dares. We no longer needed them. All pretext of a game was gone.
This was two boys finding that beautiful intimacy that only boys can
have.

As I kissed over his belly, my cheek came in contact with his hard
dick. I turned my face and took it into my mouth. The taste, the
texture, the smell. I began to give him a blowjob in earnest. Moving
up and down, licking, sucking. I loved it!

I really don't remember the next 10 or 15 minutes. What I do
remember is that we spent it kissing and caressing and sucking and
loving. It was wonderful.

We finally rolled off of each other and began to masturbate our own
dicks, occasionally kissing and feeling each other.

Still jacking, we got up off the bed and ejaculated onto the carpet at
the end of the beds. Spraying our adolescent cum onto the blue
carpet. Don't ask me why we did it this way, but it seemed right at
the time.

Not 20 seconds after we came, we heard someone coming up the
stairs, and quickly jumped back in our beds, still naked.

His 15yo brother walked through the door just as we pulled the
sheets over us. His first comment was, "Damn! It smells like cum in
here!" If only he knew what had just happened!!

He walked in and asked us what we were doing and walked over to
J's bed and tried to pull the sheet off of his naked body.

At this point, in my jacking fantasies, S (J's brother) pulls off the
sheet, sees his naked body, figures out what we have been doing,
and wants to join in.

However, as this is a true story and not a fantasy, J held onto the
sheet and S stopped trying to get it off. He said good night and left
the room and we settled down for bed, each of us reliving what had
just happened.

The next morning, as it is with sexually involved boys, we didn't
talk about what had happened. However, the next night, we
couldn't wait to go to bed.

Until I was a late 15yo, and J was an early 14yo, we got together any
time we could. When one of our parents were gone, we would be on
the phone calling the other one, and we would fall, kissing, into
each other's arms.

We started something that night that would carry on every night
that week, and for two years after, until his brother did actually find
out what we were doing. (no, he didn't join in then, either)

And, we never had to play Truth or Dare again.