Note: This story was dynamically reformatted for online reading convenience.
 
 Boarding School Series #2 - Big Steve - 01-16-2008, 11:24 AM mm anal

   Disclaimer: This story is a figment of the imagination and contains
depictions of sexual encounters between adults, teenagers and children.  If
you find the content in any way unacceptable, stop reading now.



   One of Tom's friends, Steve, was thirteen and already well hung for his
age.  He was around five inches when erect.  We'd sucked each other a few
times but often never got as much action as we'd liked, mainly down to the
difficult circumstances he had with Sam.

   Steve and Sam hated each other, so our regular jerkoff sessions never
involved the two at the same time.  We got around this by having secret
meetups without Sam knowing, something I justified by giving Sam more
private attention every now and then.

   Steve's fearlessness with cum and other grubby substances gave me the
feeling that I could get away with anything with him.  He'd drunk other
boy's cum several times as dares during our sessions, and he never turned
down the chance to prove himself in some way.  Despite this bravado, he had
remained quite quiet and shy outside of our meetings.

   Today, I had Steve to myself, as we both had the same free periods in
the schoolday.  The venue was to be our study, and he was most likely
expecting our usual blowjob exchange.

   Steve came in and we did our usual thing.  We locked the door, took off
our pants, brought out a porn mag and knelt facing each other.  I reached
over and grabbed his semi-erect dick, and he held mine in response.  We'd
usually start each other up this way and move on from there.

   His dick was always an impressive sight, and seeing it so engorged and
delicious made me take a risk with Steve that I'd never taken with any of
the boys before.

   "Fucked anyone with that big thing yet?" I asked, giving his shaft a
squeeze and trying to build his confidence.

   "Nah." he muttered.

   "Ah that's a shame, this is one of my favorite dicks." I chuckled.

   "I thought Tom's was." Steve said.  He knew Tom was always a focus for
me.  I'd given him more blowjobs than anyone else, after all.

   "His cum tastes the best, but your cock looks and feels the best." I
said, hoping he'd take it well.  Steve's cum always either tasted too
metally or too much like old chinese food.  But then sucking on a bigger
dick was a power trip, especially with the boys all watching.

   "Yeah, his cum does taste good." Steve said after a brief pause.  "And I
can make him cum quick."

   I kept slowly jerking him off and watching him get more and more aroused
as he told me about blowing Tom.  All this talk was turning both of us on,
and I knew he was ready to take it further.

   "Want to try fucking something?" I asked, giving his shaft a few
stimulating squeezes.

   "Like what?" he said, keeping his hand's rhythm on my cock.

   "Promise you won't be grossed out if I tell you." I cautioned him.

   "Dude nothing grosses me out, tell me." he replied quickly and with a
smile.

   "Okay, how about fucking me?" My heart leapt for a moment, this could go
badly wrong.

   "Your mouth or..?" Steve stammered for a second, then stopped jerking
me. "You mean fuck your ass?"

   "It's clean.  I cleaned it.  And I have lube." I spoke quickly to
reassure him.  I couldn't believe I was saying this, but he seemed
perfectly unfazed, despite being surprised.  There was a terrifying silence
as he looked me up and down.

   "Okay sure." he said, flatly confident as always.  I silently nagged
myself never to doubt Steve again.

   "Cool, and I'll let you cum inside." I said, trying my best to clinch
the deal in the best way possible.  It was hard to hold back my excitement.

   "I bet that'll feel awesome." Steve said.  Joy.  He was sold.

   I smiled and excitedly sat back on the bed, beckoning Steve to join me.
This was really going to happen, I would take his virginity and hopefully
start a new thing for us.

   "Okay, so how do we do this?" Steve said cutely.  I was already applying
lube to my asshole.  "Dude that's gross!" chuckled Steve as he watched me
finger my hole as I made sure lube reached everywhere it should.

   "Hey!" I said in semi-protest.  I knew Steve loved gross-out humor, but
when my own asshole was the subject, I was a little more sensitive. 
"Here." I said, offering him the small lube bottle.  "Put some of this on
your dick until it's nice and slippery."

   Steve hurriedly applied the lube and stood there, fully hard, with a
look that said 'What now?'.

   "Hey, let's turn the lights off so you can imagine a girl's pussy
better." I suggested.  He nodded and seemed a little excited as he dashed
to the switch, his erect cock bouncing around as he ran.  The room's one
window was heavily curtained, letting in just enough light around the sides
so we could both see what we were doing.

   "Stand real close and I'll guide you in." I said the moment the lights
went out, waving in the semi-darkness until he came closer.  He hovered
over me and I felt the head of his dick brush my balls.  His hand found its
way to my cock and he ran his fingers up the length before gripping my
shaft just below the head.

   "Dude you're fuckin' rock solid." Steve chirped.  He grabbed at my
boner, caressing the ridges of my shaft with his fingers.  He always
explored my cock as fully as he could.  "Fuck it's makin' me horny." he
said breathily.  I loved how he enjoyed my cock, and I was tempted to get
him to suck it, but my pucker was tingling with anticipation, so I had to
relent for now.

   I reached down between my legs and held his shaft steady, shuffling
myself down until my hole touched against his stiff rod.  He instinctively
pushed forward and I felt his head bump against my pucker.  He had good
self-control and wasn't pushing too hard, so I knew I could at least
control his entry.

   "That's the hole right?" he asked.  He was nothing but a shadow over me,
and my heart was thumping with excitement.

   "Yeah, now push in a little." I said, my hand cradling his shaft to keep
it aligned.  The lube was very slippery, so I hoped it would be an easy
entry.

   He gave the perfect amount of pressure as I felt his thick rod push its
way into me.  I felt my pucker squeeze over his cockhead and clutch behind
the glans.  He paused for a moment and inhaled.

   "You okay?" I quickly asked, wanting more of him in me but not wanting
to scare him into pulling out.

   "It's warm.." he said, the slight surprise in his voice made him very
cute.

   "Push in a bit more." I said.

   I felt the first inch of his shaft stretch my hole wide, his cockhead
jammed inside me and feeling much bigger than it looked.

   "..feel good?" I said, doing my best to relax and let him in easily.

   "Yeah.." he said, breathily.  I felt brave enough to move my hands up
his hips, grabbing his waist.

   "Go ahead and fuck in and out if you want." I said, giving his sides a
squeeze.  He kept silent and pushed in more.  My insides churned as he
buried all five inches into me, then drew it out a few inches before
pumping in more confidently a second time.

   "That's good." I said, lost in the feeling of his big dick pumping in
and out.  This beat using a carrot or a finger any day.

   The room was so quiet apart from our breathing and the soft slaps of his
thighs against my butt.  His cockhead felt so swollen and filling, pushing
and pulling at my insides with each thrust, but still comfortable enough
for me to relax without flinching.

   I started to jerk myself off infront of him, and he immediately
responded by taking over for me.

   "This is hot." he said as he slowly jerked my cock.  I desperately
wanted to go faster but this one was for Steve, so I kept quiet and let him
do what he wanted.  He kept a steady pace for about two minutes before he
suddenly stopped jerking me and slowed down his thrusts.

   "Is it still okay?" I quickly asked, slightly out of breath.

   "If I keep going I'm gonna cum too soon." Steve said as he put his hands
on my knees and supported himself for a moment.

   "I don't mind if you do." I said, arrogantly expecting him to be more
concerned about what I'd think of him than what he'd think of himself.

   "Don't tell anyone I didn't last long, okay?" Steve sounded serious.  I
didn't realize he actually cared what the rest of the boys thought of him,
he seemed so unfazed by everything when they were around.  It took him
fucking me to find this out, so I wondered what else I'd discover.

   "I won't, Steve, just enjoy yourself." I said, reassuringly.

   "Cool..  can i go faster?" he asked.  I almost laughed out loud, he was
very eager but afraid of getting a reputation for cumming early.

   "Sure..  hurry up and cum, willya?" I said jokingly, nudging his
shoulder.

   "I love it when you say stuff like that." Steve said as he started to
pump into me faster.  His voice was breathy and wavering, and I knew he was
close to orgasm.  As the slapping grew faster, I felt his hand grab at my
cock, jerking me clumsily, his fingers circling over my balls and taint.

   He leant over me until our heads were almost touching, concentrating on
fucking me.  My ass hugged his cock as it drilled into me, he stretched and
filled me comfortably, making my guts churn in a very good way.  We stared
down into the dark scene of the crime, both of us focussed at the point of
penetration where the wet slaps came from.  I was lost in the feeling of
his cockhead pumping in and out and my asshole stretched by his shaft.

   "Cum in me." I said, almost under my breath, hoping it would egg him on
but also nervous at sounding like an idiot.  It worked like a charm.

   "Urh fuck!" he grunted and suddenly jutted forward, burying himself all
the way inside me.  It didn't hurt but it ached somewhere up there.  He
almost headbutted me as his head came up and he grunted some more.  I tried
to focus in on the feeling of him cumming but my ass was more of a broad
zone of sensation than any one particular place I could feel.

   He was clutching my knees so hard his fingernails were grazing the skin,
but he soon relaxed his grip and I knew that he had blown all of his load.

   I had finally taken a guy's virginity, and as he slouched to one side of
me, I felt a surge of accomplishment.  The sensation of his thick rod
slipping out of me was electric, and I almost wanted him back in again.  He
rolled onto his back and stared at the ceiling, his spent cock flopped
cutely to one side.

   I put my legs down but kept them apart, enjoying the strange sensation
of being freshly fucked.  I was glad he wasn't as big as me as I bet that
would've been uncomfortable.  I hoped I'd somehow find a way to have the
other guys in me, and as Steve was the biggest, I'd have more safety and
control over what they did in me.

   "Dude.." said Steve once he'd regained his breath.  "That felt really
good."

   I sat up and reached over to the bedside lamp, flicking it on and making
us both squint from the sudden brightness.  As our eyes adjusted, we looked
at each other at the same time, both bottom half naked, both squinting and
looking ruffled.  We burst into laughter, a welcome end to what was an
intense experience for both of us.

   "Dude I bet the cum is so far up there it won't come out for a week!"
Steve laughed at his own jokes far too often, but he was so cute about it.
I wanted him to finish me off, but I knew he'd probably be too stoked about
what had just happened.

   "If you liked this, just think, Girls are even better." I said, secretly
hoping he'd still use me as a substitute.

   "Yeah..  I can't wait." Steve put his pants back on and sat on the bed
with a strange sparkle in his eyes.

   "Until you get a girl, we can do this anytime you want." I said, handing
him some tissues to hint that he should go clean up.

   "Awesome." Steve beamed from ear to ear as he pocketed the tissues.  It
was a broad smile that surprised me, as we were just intimate but I was
never one for being super-happy and sexual with guys at the same time. 
Still, my own orgasm didn't matter anymore, I'd had a blast and would wack
it out later.  I sent Steve off happy and that was good enough for me.  For
now.
   END