Date: Fri, 11 Mar 2016 14:42:51 -0500
From: Leather Dude <bklynleatherdude@gmail.com>
Subject: Gay Male/Young Friends/Losing My Cherry to My Jock Buddy - Part 3

Thanks to everyone that gave me feedback on Part 1 and 2 of this story - I
really appreciate hearing what you guys like, the more explicit the better!
So keep it cumming!

This series is based on the true stories of my sexual exploration over
several years with the boy I lost my virginity to, Carl. I changed the
names to keep out of trouble.

All the usual disclaimers apply - and don't forget to support the Nifty
Archives!

________________________________
Losing My Cherry to My Jock Buddy - Part 3

When I was in the 7th grade, I had started initiating opportunities for
sexual exploration with some of the boys in my class at Catholic
school. Being a Midwestern Catholic school during the Reagan 80's, we were
taught very little about sex other than it was dirty, shameful and bad and
we should talk, think or do anything of the sort. I had already done a lot
of exploring with my jock buddy and then got a boy form my class, Mark, to
fool around, too.

Well, 12 year old boys are hormonal as hell and I quickly figured out I
could get some of them to drop trou if I created the right environment.

Years before, my dad helped me build a treehouse in the backyard. It was
two stories and had a little hangout spot and a loft area for sleeping. I
had sleepovers there with my buddies because we were basically outside and
nobody could hear us if we stayed up late messing around. Which was just
the privacy needed to convince the boys to get naked and play with our
dicks together.

As I may have mentioned before, puberty hit me first among my peers. And it
made my cock grow to its full size by about age 13. The other boys knew it
and alternated between making merciless fun of my big cock and being
fascinated by it. Which meant they all secretly wanted an opportunity to
compare theirs with mine. And I was happy to oblige.

My one friend Josh and I had already fooled around once at his house after
school. It started with the comparison, but his was the first uncut cock I
had ever seen. We both were horny and took turns stroking each other's
cock, then ended up giving each other head. I was obsessed with Josh's
hooded cock. It was smaller than mine, but that skin drew me in.

Josh's best bud John was also in our class and lived across the street from
Josh, my house was on the other side of a big private club that divided the
neighborhood, so they lived just far enough that we didn't hang out much
outside of school. But Josh and I wanted to get off again and Josh wanted
to get John in on it. I think he'd had a crush on tall, handsome
John. Plus, if this worked out, Josh would have a suck buddy right across
the street.

So we arranged it so the two of them would come sleep over at my house in
my cool clubhouse one Friday after school. After dinner, my folks would
usually go to their room and watch TV. We three boys headed out to the
garage to get set up.

Once everyone was sure my folks were in for the night, we started with a
little truth or dare. Josh and I got racy quick and in a few rounds had
both confessed to having touched another boy's dick. John was a little
shocked, but then was full of questions. Josh admitted that it was him and
I that had fooled around. That's all it took and John was in. We all took
our shorts off, got hard and stared intently at each other's junk. But
nobody was making the move to touch each other's cock. John and Josh seemed
timid. So I had to move things forward somehow. John had a very thin but
very hard cock and was staring intently at my much thicker hard cock. Josh
must have noticed John's stare and he said " Dude, Tommy's cock is like a
Mack truck. It's so thick and hard - you can't hurt it even if you try!"

I smiled coyly and told John he could feel it if he wanted and he said that
he did but he didn't want me to watch. So I laid down and pulled a pillow
over my head so he could explore without me seeing. Josh told him my dick
was "indestructible" so John started batting it around and pulling it
forward a bit farther than was comfortable and letting it snap back hard
against my stomach. I bent my knees and moved my legs apart allowing John
to get in closer - hoping he'd want to blow me. But instead, he got fixated
on my asshole. He started poking at it and I was winking it at him a little
bit. Josh wanted to give that a go too so they switched places.

I was getting into it - I'd been fucked a bunch of times by my buddy Carl
and I really wanted to get Josh's uncut cock up there - it was bigger than
Carl's but I knew I could take it. So I told them I'd stuck stuff up there
before and they could do more if they wanted. They did. So I told them
where I had a jar of Vaseline stashed and to put some on my butthole so it
wouldn't hurt. There was some shuffling around, then fingers smearing
Vaseline on my hole followed by something blunt at the opening being nudged
in. I couldn't figure out what it was - it was not a finger, bigger than
that. But too hard and cold to be a dick. I played along keeping my face
covered - still hoping one of them would fuck me and the other would suck
me. Then it slipped in and I lurched up and my hole spasmed. It was big and
hard - this thing in my ass. And it hurt because of the sudden shove in of
a few inches. I really wanted to know what it was, so I asked and started
to push the pillow away. Then one of them moved up to keep the pillow over
my face and hold me down while the other really got down to business
shoving this thing in and out of my hole. It started to feel good pretty
quick though (an early cue of what a bottom slut I'd later become) and my
cock was steely hard hovering over my body, twitching and leaking tons of
juice that I could feel dripping into my treasure trail and dribbling into
my belly button.

I must have been making some noise moaning because John told Josh to keep
me quiet - so now I knew who was pummeling my hole. No sooner was the
pillow removed than Josh was straddling my chest holding my arms down with
his knees and shoving his hooded hard cock into my mouth - deep. But I was
in heaven with a mouth full of cock and a good ass fucking at the same
time.

John asked Josh if they could trade places and he let go of whatever he was
ramming into my ass as they moved around me. My hole was spasming and it
ejected whatever was in there onto the floor with a thud and a clatter that
sounded like - metal? And it occurred to me that I'd maybe just been fucked
with the handle of a screwdriver from my dad's tool box, which had been
sitting in the corner. That idea made me hot and also freaked me out a
little and I asked Josh to not put that back in - but to put his dick in
instead. He didn't need any convincing and slipped his uncut cock into my
well-stretch hole and grabbed onto my slimy dick.

John's skinny dick was easy for me to swallow and I could even get my
tongue on his balls. He was trashing around getting his first BJ. He was
squatting over my chest bracing himself against the wall with his hands and
my head was now on the pillow to put my mouth at a better angle while I was
still on my back. John was so horned up from doing me with that screwdriver
he only lasted a couple of frenetic minutes before he unloaded right down
my throat while I held onto his tight little ass to make sure I got every
last drop. John rolled off me and I could finally see sexy blond Josh
between my legs boning me and jacking my cock at the same time. Just seeing
the scene nearly sent me over the edge and I pushed Josh's hand off my cock
before I started to blow. I was so enjoying the sensation of Josh's cock in
my ass, hammering hard and going deep that I didn't want to come until he
did. Josh was ramming me really hard then practically doubled over on me
with his head hitting my chest as he unleashed his teen jizz in my tight,
spasming hole. I thought he'd passed out - but he just had the most intense
orgasm of his life, as he told me after, and he saw stars.

We were all panting and I asked "What did you stick up my ass, John?" and
then I saw him and Josh both glance down towards the screwdriver laying on
the floor, all slimy. And I just said, next time, I hope you'll just do
what Josh did. I promise you'll enjoy it more.  John blushed and Josh and I
laughed, knowing I was right.

The next morning, John's mom picked him up early for a piano lesson and my
folks went out to run errands. So Josh and I had more time together to 69
and he fucked me again and even let me fuck him, too. I got really into his
uncut dick - it was the first one I'd ever experienced. And Josh helped me
understand how uncut dicks worked - using his ample foreskin to jack him,
tonguing inside the hood, etc. He had the sweetest cum - I could eat it all
day. And he liked rimming my ass - and me doing it to him. He tried docking
with me - but his foreskin wasn't really long enough, plus my dick had a
fat mushroom end that was bigger than his. But it was sexy as hell trying -
so I blew him one more time while I worked two fingers in his ass to tap
his prostate. The joy of being a teenage boy, you're an endless cum
fountain if properly stimulated.

John was weird about it all and we never messed around again. I was happy
with that because it meant I got Josh's dick all to myself. We mostly
traded blow jobs after school in each other's bedrooms before dinner. The
only times we fucked was on the occasional sleepover.

Josh and I are still friends. He's married with kids now - we quit fooling
around by freshman year of high school, though. Except for Todd and Carl,
who I messed around with all the way into college, all the other boys would
get a girlfriend and leave our sessions behind. A few would come back
around if they were between girls or if their "good Catholic girlfriend"
wouldn't put out. I got used to that as most of the boys I fooled around
with felt like they had to stop having sex with other guys as soon as they
started getting attention from the girls. But both Todd and Carl were happy
to share me - I even got them into a three-way once in high school, which
was awesome - a story for another time.