Date: Fri, 29 Nov 2013 15:44:08 -0600
From: Scott <ftl_s1214@hotmail.com>
Subject: Timothy Learns How

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Timothy had just recently turned 13, but if you didn't know him, you could
easily mistake him for being a boy of ten or eleven. Short for his age and
slight of build, he had the outgoing confidence of a boy who knew he was a
late bloomer and tried to compensate for it by being somewhat cocky.

Timothy had chestnut brown hair with long bangs that swept across his
rather fine eyebrows. His eyes were somewhat small for his face and,
depending upon his mood, appeared either brown or hazel. He had a small
button nose adding to his childish features and below it a widely drawn
mouth with a full lower lip.

I used to love standing across the aisle from him in 7th grade
P.E. watching him undress in the locker room. Our school required we wear a
jockstrap as part of our gym uniform and so we all had to fully undress at
one point in order to put on our jocks. I always managed to take discreet
glances towards Timothy when he pulled down his very white underwear before
slipping on the tight, small jockstrap he wore.

He had a cute, boyishly sized penis and balls. Soft, his dick appeared to
be about two inches long. His cocklette rested on a very round, very snug
scrotum. Both his dick and his balls had that beautifully pale quality of
prepubescence. As for the rest of his body, he was slender without being
what one would call skinny. His physique showed hints of muscular
definition, especially around the flat sheath of muscles covering his
tummy. His ass was a thing of real beauty, jutting out from his lower back
with mellow, concaved hollows on the sides. Naturally, his body was totally
hairless and his skin had a beautiful tawny hue that featured a ghostly
imprint of milky white around his midsection where he wore a Speedo. That
Speedo tanline was really a turn-on for me. I was later to find out he swam
on his neighborhood's swim team during the summer. I watched as the
difference in tone between that tanned and untanned skin faded as the
school year progressed, but always reflected upon how dramatic the contrast
was the first time I got to see him undress.

I'm sorry to say that I was only able to enjoy one occasion when Timothy
and I got to explore sex together, but it remains for me one of the hottest
memories of my adolescence. It happened on a day when we skipped school
together.

In addition to having PE with Tim, as he preferred being called, I also had
math, which was just before the lunch period, so we ended up having lunch
together nearly every day. One day during lunch I suggested we skip school
the next day. We agreed to meet the following morning at a discount store's
parking lot near the school. Both of us would get off our respective school
busses and quickly run towards the parking lot and then from there spend
the day walking around. Amazingly, at the time, our school was rather lax
in following up on student absentees and didn't require a note from a
parent the following day when returning from being away. One just had to
hope that the amount of days one was absent during the previous quarter
wasn't noticed by one's parents when the quarterly report cards appeared in
the mail.

It was a beautiful early October day the day we skipped. The morning
temperatures were in the upper 60s. The trees were just starting to change
color and there was one of those beautiful perfectly clear blue skies. Tim
arrived wearing blue jeans and a simple black t-shirt and black converse
tennis shoes. I was also wearing jeans and a t-shirt and a pair of Adidas.

We decided to walk to a rather large park that was about a mile away. In
addition to the park having large open spaces it also featured woods with
walking trails. We'd both been to the park individually on several
occasions. Tim asked me if I was aware of a small cave that existed in the
park. I told him I wasn't and he agreed to show me where it was. We entered
the woods from one of the paved asphalt walking trails and ended up rather
deeply in the woods before Tim said, "This is where we turn off." We headed
into the woods which were starting to show several fallen leaves on the
ground. I loved the crunchy sound of the dead leaves beneath our feet as we
made our way. There was a light breeze and the woods would make sounds
resembling the crashing sound of waves at the beach as the mostly covered
trees blew in the wind. About fifteen minutes into the woods I could see a
small hollow along the side of a small hill covered in trees. "Here it is!"
Tim announced with excitement in his voice. I loved how high and reedy his
voice still sounded. Mine had just recently begun to break and deepen. He
jaunted ahead of me, giving me a chance to check out his cute little butt
twitching up and down as he ran.

"Cool, huh, Kev'?" I looked around and thought it looked more like a
hollow, than an actual cave, but agreed with him that it was cool. Tim
flopped down on the ground, laying on his side and then his back, folding
his hands underneath his head, looking up at the trees. "Man, this is
fun. I wish we could skip all the time. I hope my Mom won't notice I
skipped."

"Just be sure to get sick once or twice between now and the end of quarter
so she doesn't notice it."

"Yeah," Tim said with a bit of concern edging his voice. "Hey, can I ask
you something, um, kinda personal?" Tim turned from laying on his back,
onto his side. I quickly adjusted my focus when he did so, as I was
appreciating the slight appearance of skin that appeared between the hem of
his t-shirt and where the white elastic from his briefs were peeking above
the waistband of his jeans as he lay on his back.

"Sure," I said, wondering what he was about to ask me.

"Can you sperm?" A look of anticipation was on Tim's face as he awaited my
answer.

"Um, yeah. Yeah, I can sperm." We were both at that age of innocence where
we didn't know the word "cum" yet.

Tim's eyes lit up and he then asked, "What's it feel like? I mean, when it
squirts out?"

I giggled. "Real good. Um, so, I guess you can't yet, huh?"

Tim looked a little embarrassed, and looked down at a leaf he was twirling
in his fingers.

"Well, the thing is, I um, well....I don't really know how to make it
happen. Do you think I might?" I suddenly got the impression he must have
caught me checking him out in PE before.

"Think you might what?"

"You know. Make sperm." Tim sounded a bit frustrated in addition to being
somewhat embarrassed. It felt good to know that he trusted me enough to ask
something so personal though. I was feeling my penis begin to twitch and
elongate inside my size 14 Fruit of the Looms. I glanced down quickly at
Tim's crotch and saw a slightly bowled out shape appearing along one side
of his zipper and realized he was apparently getting a boner too.

"So, um, like, you've never...you know...jacked off before?" I
asked. "That's how I make mine come out." Feeling a bit embarrassed at
admitting to something that all boys denied ever doing, even though we all
did. Well, apparently, all except my little friend Tim. The thought that
he'd never jacked off suddenly causing me to feel majorly horny.

Tim giggled nervously and made the hand gesture you see boys making
jokingly from time to time. "You mean this?" he said as he rapidly shook
his clenched fist in midair.

"Yeah, that, silly!" I giggled along.

"You mean that really works?"

"Hell, yeah, it works. Feels really good." Pausing before adding, "Feels
like you're fucking a pussy." I felt my hardening penis reach full mast
inside my tighty whities and felt that delicious tingle you get when you
get that sudden jolt of warm blood that comes at the peak of a full
erection. Being a horny 13 yr old without very little self control, I found
myself reaching my hand down to my crotch and pressing into it. "Fuck, this
is giving me a boner." I giggled.

"Yeah, me too." Tim responded and I looked down and now clearly saw a very
discernable boner ridge angling up just to the side of his zipper.

We lay there on our sides, facing one another, now looking at one another's
very noticable excitements arching up and away from our groins inside the
snug fit of our jeans. "Want me to show you how to do it?"

"Man, Kev, would ya?" I loved how excited he looked. Both in his face, and
"down there". I felt my heart racing knowing that I was about to see a boy
who I'd fantasized about while jerking off in the shower and in bed. To see
him hard! To see him jacking off! To see ME jacking him off! To feel his
hard dick. I couldn't wait to see how much bigger he was when hard.

"Do you think it's safe here?" I looked around.

"Yeah, I think so." Tim said and I noticed he was rubbing himself. "Please,
Kev. Show me, please?"

I turned over onto my back and quickly unbuttoned and unzipped my
jeans. Tim doing the same. Both of us arched our hips at the first time and
I immediately glanced over to see his incredibly white briefs coming into
view. His mom must have really been a fan of Clorox, because his undies
always looked so clean and so white. My mom didn't seem to be as fastidious
a housewife, because mine were always a bit off-white. That white cotton
looked so sexy against his tawny skin tone.

Our jeans hovered around our knees and we sat there for a moment, oggling
one another's boners tenting up the front panels of our y-fronts. His cock
was pressing firmly against the inside of his briefs looking like an arrow
pointing up towards his belly button, which was now in view. The hem of his
t-shirt having ridden up a bit as he was tugging down his jeans. He had the
cutest little belly button. It was neither an innie nor an outie, but a
small ridged dot with a squiggly line down the center that lay flush with
the skin around it.

"C'mon, take em down...I want to see your boner. I'll show you mine too."
Man, he sounded as horny as I felt. I loved how he was sounding a bit
impatient.

I arched my hips again, hooking my thumbs into the elastic band of my
briefs and tugged them down to where my jeans were hovering around my
knees. I was just at that stage of development where I was still hairless
save for just a few wispy hairs that had started to appear in a thin line
where my penis sprung up from my crotch. I'd measured myself recently and I
was just a little over four inches. My balls were still velvetty smooth,
but about the same time I'd first started to masturbate over the summer,
noticed they'd begun to grow larger in volume and hang a little lower than
they had when I was in sixth grade.

"Your turn," I said nodding my head down to where his horny little cock
still jutted up inside his clean cotton briefs.

There was a brief hesitation and then Tim arched his narrow hips and
descended his skimpy tighty whities. I couldn't help notice as they came to
settle just above his jeans that the size tag inside the elastic band read
size 10. I was already wearing size 14. For some reason that difference in
size turned me on even more. But, needless to say, my eyes didn't rest long
on his briefs when I had his very hard erection to look at. He had a
beautiful cock! It was so slender. He was what I guess you would call a
grower versus a shower. That's to say, when he was hard, his penis doubled
in length. What I'd seen in PE was half the length I was now looking at and
was surprised his erection was very nearly as long as mine, however, it was
still very boyishly slender. His girth couldn't have been much thicker than
the thickness of his index finger. It stood aloft from the milky skinned
surface of his groin at a horny 75 degree angle. He was so hard I could see
his penis pulsing as if it had it's own little heart inside it. His tip was
about the size and shape of a cherry; the front pugged out a bit like the
pugged nose on his face. I noticed that with him being hard the skin
covering it had a much more inflamed coloration to it, unlike the dusty
rose it normally had. Below his dick was his compact, rather small balls
sack. He had the kind of scrotum that resembled one large ball instead of
two individual ones.

"You gonna show me?" Tim said, a look of horny need written on his face as
he waited my reply.

"Let me show you, by doing it to you. You'll like that. That's how I did it
the first time. My cousin showed me how when I slept over at his house this
summer."

"You won't tell anyone, will you?" Tim sounded a bit concerned. "I
mean...about me not knowing how and stuff?"

"Hell, no. And, you'd better not tell anyone either, about me jacking you
off."

Tim beamed in horny expectation and said, "No way I'm tellin
nobody. Please, do it?"

I reached out my right hand and gingerly encircled his slender tumescence
within my first three fingers and thumb. He stood at about 3 and a half
inches. His skin felt like warm velvet that had been laying under a hot
sun. I immediately felt his boner flinch in my fingers and Tim took in a
sharp inhale of air. I squeezed him gently, feeling the rubbery give of his
excitement swelling slightly. His tip exposed beyond my grip, the
buttressed shape of it swelling slightly in a spasm. Tim's knees spread
slightly, causing his underpants to stretch into a narrower line just above
his knees.

I slowly began to stroke him up and down, delighting in how incredibly
smooth the skin felt. I'd never touched another boy before. Touching my
first dick other than my own was an incredible turn-on and my boner flexed
in hard upward lilts as I felt surges of blood causing my dick to tingle in
excitement.

"Feeeeels gooooood..." Tim said in a voice so soft I could barely hear it.

"You rub it up and down like this," I said, hearing my voice shaking
slightly from a combination of nerves and horniness.

Tim's cute tummy began to expand and suck back in as he started to make
soft muffled whimpers of pleasure. "Feels tingly!" Tim let out with a sound
that seemed edged with anxiety. "Kinda itchy and tingly at the same time!
Is it supposed to feel that way, Kev'?"

"Yeah, Tim; yeah it is. You likin' it?" I asked, my eyes darting between
his face and the sweet little cock I held in my hand. I loved how boyish he
was. I was at that stage of my adolescence where growing up scared me and I
envied how he was still more boy than teenager.

"Yeah...oh rub it!" Tim pleaded. His legs were spreading out more now. I
used my other hand and descended his undies and jeans down to his ankles,
sensing how he wanted to spread his knees more.

"Pump it, pretend my fist is a pussy." I said, giving him the permission I
felt he needed, knowing how much I liked to pump my hips when jacking
myself off.

Tim's little groin began to undulate up and down in somewhat spastic little
thrusts. It was clear this was his first time. And knowing so was causing
my penis to feel like I might just sperm without even needing to touch
myself.

"Oh....feels like I'm fuckin a pussy, Kev'!"  Tim practically squeeled in a
voice that seemed to nearly rise to a falsetto. As if either of us knew, or
would know, what that actually felt like. "Yeah, pretend you're fucking a
tight pussy, Tim" I said, feeling his jutting boy cock jabbing in and out
of my fingers, and feeling the skin covering it starting to feel a little
damp with perspiration, perspiration from his hard-on and from my fist. I
began to gently squeeze and release my grip, thinking about how I'd want a
handjob to feel on my dick.

Tim's pistoning began to increase in speed and intensity. His tummy was now
drawing in and tensing up more and more frequently. His breaths coming out
unevenly in shallow pants.

I glanced into his face and saw him looking down at his dick, a look of
concentration written on his face. He was starting to grimace a bit, his
eyebrows arching up and knitting together and the nostrils on his cute
little button nose flaring a bit.

"Kev! It feels funny inside!" Tim yelped as his little groin took on a
frenzied pace. I knew he was getting close now, even if maybe he wasn't
aware. His slender delicately shaped pubis seemed to look slightly puffed
out and his already small scrotum seemed to be growing more compact. I
could feel the silky surface of his little boy bag brushing against the
cuff of my hand and could feel the slightly dewy surface of his hairless,
milky skinned pubis slapping against my hand as well.

I reassured him, telling him, "It's okay, Timmy. It's okay, you're just
gonna sperm."

"KEV! WAIT! OOOOOOH.....!!!!!" I quickly glanced into his face and saw a
look of utter helplessness written there and then quickly returned my focus
down to his stiffy. Tim's narrow hips suddenly rose up and locked in
shuddering place. I squeezed his boy cock and felt it swelling back in
spastic quivers. I could feel Tim's skinny dick kicking inside my fist. His
tip was now a bright purplish pink. At that moment, I felt he was probably
going to end up having a dry orgasm. And, then, it happened. I don't know
who was more shocked - him or me. Suddenly, Tim squirted three rapid fire
crystalline spurts of clear, obviously spermless, semen onto his tightly
clenching tummy. Tim letting out tight tummied grunts that resembled a boy
who has been kicked by surprise. There was such a vulnerably sweet innocent
quality to those tones that even if he'd not told me earlier, I would have
known I was witnessing a boy's first climax. The sight of his diminutive
boy cock squirting for it's first time, in combination with those helpless,
somewhat fearful sounding cum grunts, pushed me over the edge. Suddenly,
for the first time in my life other than the one wet dream I had shortly
before beginning to masturbate, my 4 incher was squirting it's slightly
foggy load of thin sperm onto the grass and fallen leaves between us
without my even having touched it. "SPERMING, TIMMY!" I yelped loudly as i
felt the stinging squirts of my ejaculation bulleting up my flexing 13 yr
old cock. Tim looking over as it happened and then fucking into my fist in
a secondary paroxysm of violent and rapid pumps before collapsing back down
onto the grass like a damp wash cloth. Tim whimpering, "I spermed...you
made me sperm, Kev. I spermed..." His words coming out weakly between
gaspish breaths as he tried to catch his breath. His face was flushed and
misted with perspiration and his eyes somewhat glassy with a look of
exhaustion.

His first ejaculate was so thin that it was like clear pee and as he lay
there panting in recovery I watched the three little splatters that had
landed up near his belly button already beginning to drip down into the
v-shape of his pelvis. His penis was still as stiff as it was before I
began to jack him off and I watched as it made jerkish upward lilts away
from his body. A little bead of his clear boy semen bubbling up from his
slightly dilated piss slit. I'd just taken his "cum cherry". I'd just
jacked off a boy for the first time. And I was in heaven.