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My 1st time

As a lad I used to hang out with Ted, another neighborhood lad my age, who
had an above-ground 6 foot swimming pool. Ted was a bit wacky, but
unlike his older b*****rs, he wasn’t one of the neighborhood tough
guys. We got along swell. We were doing the usual stuff k**s do in a pool;
whirlpools, cannonball competition, wacky dives off the garage

During one of my attempts at a somersault dive, the trunks I had
borrowed from the huskier Ted slipped right down my legs, leaving me

Ted immediately thought it was funny to grab the
wayward trunks and play keep away. I told him “Hey, what if your
mom comes home…give `em back”. He said he didn’t care, doffed his
own trunks, and dared me to dive naked. He used to dare me all the
time, and would usually do the dare himself first, knowing my
pubescent pride would f***e me to follow suit. Pretty soon we were
both doing a naked dive competition and generally acting goofy.

I recall it was the first time I swam nude, and it felt so good to
be free of that little piece of cloth. The water flowing unhindered
between my legs was exciting (not to mention the thrill of doing
something naughty and of being caught). We frolicked innocently for
about ten or so minutes before I noticed Ted’s older b*****r, Tom,
watching from the 2nd floor bedroom window.

Tom was older; a big meany and a tough guy/sports jock who often
got his ass kicked by the oldest, even tougher/meaner b*****r, then
promptly took it out on Ted.

Sometimes he condescended to be nice
to us, or include us in a local baseball or red rover game if he
lacked guys his own age. Mostly he ignored us and, to my good luck,
he never fucked with me much.

Once Tom saw I spotted him, he disappeared and I told Ted we might
be in for it. We hurriedly put our swim trunks back on. Tom came
outside, a stern look on his face, and asked what we were

“Nuthin’..” we said. “Come on, let’s go to the forest” said
Tom, as he picked his bicycle up. I guess we were so shocked he
wasn’t pissed that we followed suit without a word. In fact, we
didn’t speak at all as we rode the few blocks to the footpaths of
the wooded area we called `The Forest”. We stopped in a familiar
clearing, off the main trail. It was there Tom stated his

Tom said “I saw what you two were doing in the pool…have you ever
done a train?” He looked at me as he said this, and it seemed to me
Ted was somehow familiar with the concept. I shrugged my shoulders
and tried to be cool as my mind raced, not understanding what Tom
meant. “You k**s don’t know shit”, Tom said as he pulled off his
shorts…”this is something men do”.

Ted had taken his trunks off
again, as if on cue, and they both looked at me, making me feel
quite self-conscious. I skinned my own trunks off and as I did, I
noticed something I had previously never seen on another guy; Tom’s
penis standing straight up, bright red and fully erect. He probably
rode the whole way with his hardon.

When Ted & I were swimming nude, neither one of us had any sexual
thoughts, or at least they didn’t manifest themselves into an

I had certainly experienced enough of my own boners
during my youth to know what was up. Tom’s hardon was the first I’d
ever seen besides my own, and his post-adolescent penis, sprouting
from a thick patch of pubic hair, made my own hairless pecker and
testicles look tiny. Even Ted had a healthy sprouting of hair on
his crotch, and for the first time I noticed his dick was also much
bigger than mine.

Tom made a comment about my hairless state, and
noted my limp little peanut stating “if you can’t make it hard, you
can’t play with the big boys”. Ted was tugging and rubbing his
penis, and helpfully advised me to “go like this”.

Now it’s not like I never tried to masturbate before then, but my
budding sexual organs just weren’t ready to produce
seminal fluids. I heard other k**s talk and theorize about jacking
off, and once even tried to make myself orgasm by holding my
vibrating fishtank air pump against my erect dick.

It seemed that I
could get close to the unknown but fabled “cumshot”, but when my
knees got weak and my cock started to spasm (in what I later learned
was a “dry” orgasm) I got scared and quit.

Tom was holding his stiff penis at the base and proudly displaying
it. It seemed too big for his body (which was muscular and big for
his age), but in retrospect, I’d say he had about seven to eight
circumcised inches, with big balls hanging down longer than normal.

Ted had gotten himself hard by then, and he was just slightly
smaller than his sibling. Ted was so relaxed about the whole thing;
I guess growing up with older, outspoken and horny b*****rs lowered
his inhibitions. I, on the other hand, was as nervous as a cat.
All my novice attempts at making my dick erect were failing as I
stole glances at the two b*****rs’ proud erections. “I’ll be ready
in a minute” I boldly lied.

“You get to be the engine then” Tom impatiently informed me. Ted
had already lined up behind his b*****r. “What do I do?” I
inquired. “Just turn around and spread your butt cheeks” said
Tom. “Huh?” I stammered nervously. He informed me “Don’t worry,
I’m not gonna put my dick in your butt…only homos do that”. I
turned around stiffly, cupped my skinny pale buttocks in each hand,
and prepared for the worst.

I felt all at once the heat from Tom’s
body, the smoothness of his cock pressed along the crack of my ass,
and the tickly feel of his pubic hair against me. I felt his breath
on my neck and his hands gripped firm my narrow hips. He began
pushing himself against me, as I suspected Ted was doing as
the “caboose”. Since he outweighed me by a few dozen pounds, I was
being propelled forward.

Tom instructed me to put my hands against
the trunk of a close by tree.

Once I braced myself, Tom’s rubbings began to feel more like
thrusts. He stopped pressing against me for a second and I heard
the unmistakable sound of his pursed lips squirting out spittle. I
felt disgusted, but remained mute as his hot saliva splattered at
the top of my ass cleft. He spat again, this time drooling it
directly onto his penis.

I couldn’t imagine why he did this until
Tom’s renewed thrusts made me understand. The spit lubricated Tom’s
grindings and his cock began to work against the crack of my ass
like a fleshy piston. I felt his hands work my ass cheeks apart so
he could push the length of his long dick in the channel between my
cheeks. His long-hanging testicles were slapping me rhythmically,
hitting against my own tight nutsac. The whole episode was
beginning to seem strangely exciting to me, and at the same time
wrong and secret and shameful.

I could feel the swollen bulb of Tom’s cockhead slipping rapidly up
and down my rear-end. It made a squishy/juicy sound as he squeezed
my asscheeks around his dick, like a hotdog in a bun. It even hurt
me a little, but the regular beat of his hips against mine were
making my floppy little pecker swell up. It felt good…even as I
felt used and powerless. Tom’s breathing was becoming as frenzied
as his thrusting.

Everything was increasing at once, and I became
more afraid not knowing where this building pressure would end. I
wanted to run, but also wanted to know.

Tom began to swear. At first low, then building, but in a
threatening tone. “You fucker…Oh you little fucker…Ungh…you
fuck”. He cursed me even as he dug his fingers in, big hands
painfully pulling my hips to his groin. “UHH…fuck..unngh…you
fuckerrrrr” he growled. At the same time, I felt his cock throbbing
between my buttcheeks.

He pressed hard and held tight against me,
panting, his tense body shuddering. I felt something hot, even
hotter than Tom’s spit, spattering the small of my back and sticking
there. Four or five times, these hot blasts squirted between my ass
cheeks. I thought he was somehow pissing on me in spurts. Each
time, Tom moaned as if in apology…”Aw..aww..awww” and then a
final “Ahhhhhh”. I didn’t know what to think. My head was spinning
with all of this and I felt faint.

I could smell a bleachy-sweet
scent in the air. I was vaguely aware of Ted’s voice, far away and
low in a way I’d never heard. I held on to the tree to keep from
falling on weak knees.

Tom had ejaculated a huge load of sperm onto the small of my back
and between the small globes of my ass. Even though I never saw it,
I have imagined it, based on what I felt that day, over and again a
million times.

He released one side of my hip and I could feel his
fingers fumbling behind me. His other hand roughly spread my butt
cheek, and he began rubbing his diminishing erection up and down the
thick warm mess he made on me. He must have been milking out the
last of his cum, as I felt him paint my buttocks with even more of
his slippery hot jism.

As Tom rubbed the head of his cock along my crack, I shivered at the
sensation of his firm flesh sliding back and forth across my tight
wet asshole.

He did this for a deliciously long time, and I think
it was to give his b*****r, who was obviously still humping away at
Tom’s own ass, time to shoot his wad. Tom’s penis had softened to
what felt like half-hard, and he kept flicking the tip up and down,
teasing my puckered asshole and spreading his semen in my crotch.
Tom’s cum, which seemed to stick to my skin like warm taffy, was now

I could feel his seed sliding down my back and butt,
running down the back of my thighs. Ted must have finished, because
Tom stepped back from me and said laughingly, for his b*****r’s
benefit, “man I shot a BIG wad on Johnny”.

It was obviously clean-up time, and Tom shocked me by putting his
cupped fingers between his legs and scooping up what looked like a
large phlegmy hawker. I don’t know if it was his b*****r’s semen or
just overspill drippings from the load Tom blasted onto my ass (I
never questioned Ted about anything that happened on that day).

flung the glob of cum into the air, trying to hit Ted with it. I
was still in awe of the whole experience, as Tom began to chase Ted,
shouting “sniff my hand…here, eat this sperm”. That was Tom the
bully I knew so well and I reached for my trunks, in case I needed
to make a fast getaway. Things calmed down, and with Ted’s
permission, I ripped the inside pocket lining from the borrowed
trunks and used it to wipe Tom’s cooling ejaculate from my ass.

again smelled that bleachy-sweet odor and was at once repulsed and
fascinated as I threw the cum-stained cloth into the weeds. The
last thing Tom said to me about the whole affair was “You’re a
fucking mess”, admiring his handiwork while I cleaned myself off.

We rode back home in silence and never mentioned what happened that
day. I often feared Tom would tell his friends about me and my name
would be mud around town.

The only veiled reference he made was to
call me “homo” and “faggot” a couple times; something he said about
most everyone at one time or another. I always kinda hoped Tom
would repeat the performance with me, but he mainly ignored me. Ted
and I drifted apart as friends after that summer, for no real reason
I could think of. By the time I got older,
I was masturbating regularly and usually my fantasy involved some
variation of Tom’s big dick cumming all over my ass.

To this day, I
recall the sexual event vividly, and from the first word in this
story, I’ve had a raging hardon in remembering it.

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