Note: This story was dynamically reformatted for online reading convenience.
 
 Boarding School Series #3 - David - 01-20-2008, 01:42 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.



   I had a two-hour afternoon session with thirteen-year-old Sam and
eleven-year-old David.  I had big plans for David, who had expressed his
interest in taking a cock up his ass just last session.  At first I figured
it was youthful bravado; his attempt to make a good impression and
establish himself as a tough guy among our group, but his steadfast
attitude and complaint-free cocksucking of the other boys made me think he
had the right stuff to back up his claims.

   The session began, as always, with all of us bottom-half naked.  David
sat on the bed with Sam, while I sat on the chair beside the bed.  Sam was
already erect in anticipation, his cock just under four inches of pale,
circumcized pole.  I glanced down at David's little dick, pre-pubescent and
delicious-looking.  Soft, it lay around two uncircumcized inches, maybe
less, with a mild yellowish tan.

   "Alright boys, this time I want to try getting a finger into your ass,
David." I wanted to give them no illusions as to the pros and cons of their
bravado.  "If you can't handle it, you tell me and we all keep it a secret,
okay?"

   David nodded.  "I'm ready."

   "Lie down and get comfortable." I gestured and he immediately and
excitedly complied.  Sam lay alongside him, eagerly handling his own cock.

   "Sam don't cum yet, I need that load for later." I snapped, hoping he
would be able to control his usually overenthusiastic libido.

   "Aw man." Sam shrugged and got off the bed, standing alongside me as
David lay on the bed with his butt facing me.  I grabbed his knees and
spread his legs apart.  Sam chuckled with glee, grabbing my arm with
excitement.  I felt his cock bump against my thigh.  I had to resist
sucking him off.

   "Sam pass me the lube." I said with the cold stance of a surgeon. 
Within moments the tube of KY was in my hand.

   "Keep your legs wide, David, it'll make it easier." I said.  He
immediately obliged.

   I squeezed a penny-sized blob of lube onto my fingertip.  David looked
his usual calm, quietly curious self and I felt a building excitement.  My
gaze wandered and I indulged in the sight of Sam's erect cock wobbling a
few inches from my leg.

   "Hey!" Sam exclaimed, giving me a nudge.  I replied to his contact by
grasping his cock briefly with my other hand, giving the shaft a squeeze.
He felt so rigid in my grip and I heard him give an intake of breath.

   With Sam's cock in my other hand, I brought my lubed finger up to
David's asshole and gently daubed the slippery fluid onto the centre of his
anus.  I took my hand off of Sam's cock and grabbed the tube for another
application.

   "You okay?" I asked David after the second blob of lube was smeared onto
his hole.  He nodded and gave me a wide eyed look that said 'get on with
it'.

   I then began pushing my fingertip into his pucker, feeling the pressure
as his tight asshole resisted ever so slightly.  The entry was a smooth,
slow squeeze that felt electric.  My fingertip rested inside David's warm,
tight, eleven-year-old asshole, his sphincter muscles clenching and flexing
around it.  My cock immediately grew hard.

   "Try and relax it so I can go deeper." I asked.  David immediately
responded, surprising me.  His hole gave way to my finger, letting it slip
deeper to the second knuckle.  In response, my cock immediately began to
leak precum.

   "Whoa it's all the way in!" Sam said excitedly.  "And your cock is
huge!"

   David flinched at the sound of that.  I think he considered my cock
would be going up him next.

   "Sam, your cock is going in him today." I said.  Sam's eyes lit up.

   I slipped my finger out of David's hole and gestured Sam to swap places
with me.  David seemed nonchalantly involved throughout, and I was amazed
at how calm he was managing to be.  His hole looked so smooth and spotless,
like a little candy.  His pucker rim bulged out perfectly, the lube making
every curve and contour slick and shiny.  His ballsac was tight and
hairless, with nicely ridged scrotum skin leading down to the bulge of his
PC muscle.

   David's cock was reasonably erect, not quite fully at attention but as
engorged as the mood allowed.  It was around three inches long with velvety
smooth skin and a neat little cock ridge.  His skin was tan enough to
obscure most of the veins and give his genitals a shiny, naturally oiled
look.

   In contrast, Sam's cock was pink and pale with thin veins criss-crossing
under the skin.  His foreskin was pulled back almost completely when erect,
and he had a bead of precum on the tip.  I wondered how long he would last
inside his first hot tunnel.

   "Alright Sam, get your cock in position, but no pushing yet!" I said,
giving him a reassuring slap on the butt.

   It was an erotic sight to see Sam position his cockhead between the
boy's naked buttocks.  The two looked at each other and chuckled, obviously
fully aware of how ridiculous the scene must've looked like.

   "Alright Sam, line up and push in when you're ready." I said, trying to
contain my excitement.

   "Yeah." Sam was transfixed on his cock, watching it nestle at David's
hole.  I could see the concentration on both boys' faces.

   Sam moved very slightly, enough for me to visibly notice.  David's sharp
intake of breath signified his entry.  The two boys froze for a second and
I leant over Sam, looking closely at the depth.  He was around an inch
inside the kid.

   "You okay, David?" I asked.  David nodded.  I felt like I should loosen
him up a bit, so I gestured at Sam to stay put while I bent over David's
cock and brought it to my lips.

   "What you doing?" He asked immediately.

   "Sucking you off for a bit." I replied, frankly.  Sam chuckled and gave
a slight grunt.  He had already begun fucking him, jumping a step or two
ahead of my plan.  But then plans in those situations tended to quickly
fall apart in favor of wherever the mood took us.

   "Don't pump in too deep, Sam." I cautioned.

   "Sorry, can't help it." Sam replied.  And who could blame him?

   I gently clasped David's fragile little dick in my fingers and slid my
tongue around his cockhead before slipping my lips over it, taking the
whole head into my mouth.  David gasped softly and I began suckling and
slipping my tongue around.

   "It's good.." David grunted, his voice wavering.  He seemed to be really
into it.

   As Sam fucked him, the motion pushed his cockhead further into my mouth
in a light pumping motion.  David's thin shaft felt so delicate against my
tongue and I relished in the texture and smoothness of his cockhead.

   "Whoa." Sam faltered and I heard the wet pop of his cock slipping out.
Before I could take my mouth away I felt David's little cock throb.  He was
having a dry orgasm.  I held my mouth over him and gave moderate suction
until the pulsing subsided.  His chest heaved and I felt a great sense of
achievement in his afterglow.

   "Nice!" Sam said, recognizing what had just occurred.

   I slipped my lips off of David's shrinking cock and gestured at Sam to
get back to business.  He eagerly positioned himself and slipped his cock
back inside David's asshole.

   "Sam go faster." David said with some eagerness.  His orgasm had made
him hungrier.  Sam obliged him and began pumping deeper and faster.  David
immediately closed his eyes and sniffed a deep breath, grabbing the sheets
with his hands.  It was such a hot sight to see the smooth, hairless
eleven-year-old being fucked like this.

   "Charlie, I'm close.." Sam gasped.  It was all too soon.  His butt
wobbled cutely with each thrust, and both boys had flushed faces, lost in
the feeling of it all.

   I unzipped my pants and brought my cock out, slowly jerking myself as I
watched the boys fuck.  It was a great sight to see David's little twelve
year old cock bouncing back and forth as Sam fucked him.

   "If you can take Sam you could try me later." I said to David.  He
turned toward me and his eyes moved down to my cock as I slowly
masturbated.

   "Not yet.." David said as he noticed my fifteen-year-old six-incher. 
"Too big!" He grunted as he got used to Sam's deeper thrusts.

   I relished in the kid's attention as he stared at my thick pole.  I gave
him as good a show as I could, making sure to draw my foreskin back and
forth, working my shaft so he could see every detail.  Sadly, his attention
turned back to Sam.

   "Sam, you gonna cum?" David asked, boldly.  I enjoyed this new kid's
quiet confidence, not to mention the fact that he had a penis inside him
for the first time and hadn't complained once.

   Sam nodded a yes, his eyes closed and his head beginning to lean
backwards.  I stood up and came up right next to them, resting my hand on
Sam's butt.  I felt a heavy rush of excitement feeling Sam's thrusting
motions and thinking of his rod jammed in David's hole.

   "I'm close.." Sam grunted.  I suddenly felt mischievous and slid my hand
between Sam's butt-cheeks.  His breathing became panting as my finger found
his asshole and I gently nudged at his entrance with my fingertip.  It set
him off like a rocket.  "Ffffuck.." Sam breathed out heavily as he spoke,
freezing in place as he came.  I felt his hole contract against my
fingertip, pulsing as he shot his load inside David.

   "Yeah!" David huffed under his breath, feeling the strength of Sam's
last few thrusts.

   Sam's cute panting faltered into soft wheezing breaths as the last few
spurts shot out of him.  I moved directly behind him and let him lean back
onto me, feeling the heat of his back and looking over his shoulder to see
his cock slip out of David's asshole, slick and sticky from their sex.  I
looked up at David, who promptly gave me a thumbs up.  He was a real catch,
very matter-of-fact even in the fresh buzz of a new situation.  I felt so
confident with him, like I could try anything.

   "Wow.." Sam phewed as he moved out of my grasp and sat on the chair
beside the bed.  His cock was rapidly shrinking, still slippery from his
cum and David's lubed hole.

   "Well done." I said, giving Sam a pat on the shoulder.  I turned toward
David and gave him a broad grin, he had taken a cock like a champ and I was
so proud of the bold little bastard.  "And you, you did great."

   David beamed, flushed with a mixture of pride and the sexual fluster of
an unresolved afterglow.  He was, after all, pre-pubescent.  My boldness
took over and I brought my finger up to his freshly-fucked asshole.  The
slickness of lube and semen made my fingertip enter him easily.  I slid in
until my finger was fully immersed and watched for his response.

   "Can you feel the cum up there?" he quipped, half-joking.

   "Nope." I said, pulling my finger out.  "Try squeezing it out."

   "Ew!" Sam chuckled.

   "Okay." David said, flatly.  He brought his arms alongside him and
seemed to concentrate.  I watched his asshole flex as a bead of cum popped
into view.  Sam burst into giggles.

   "There's the cum." I said.  "Nice one!"

   David beamed at me, a thin trickle of semen oozing out of his asshole.

   "You ready for my cock now?" I asked, not entirely serious.  David shook
his head with a wide eyed look.

   "He's gonna have trouble with that one!" Sam laughed, sitting back to
enjoy the afterglow of a good fuck.

   I looked over at David, whose cautious gaze was fixed on my erection.

   "Go ahead and touch it." I said.  David shuffled around and reached out
to grab my shaft.  He cooed as he felt the thickness and length.

   "Wow." He said.  Again, I relished the attention.

   David's small hands made everything look even bigger, and as he began to
slide my foreskin back and forth, precum oozed out of the tip of my cock.

   "Cool." He said, staring at the clear fluid as it beaded and began to
slickly trickle down the head and shaft.  "Cum?"

   "Precum." I said, taking his hand and lifting it off my cock.  "Want to
see it cum?"

   David shrugged and nodded.  I knew he was keen.

   Sam rolled his eyes at me and I gave him a little kick.  The cheeky
fella had seen it all before.  I got a good grip on my cock and jacked it
right there infront of David's face, aiming at the bedsheets.  Due to the
steamy sex I'd seen moments before, I didn't have much stamina left. 
Precum began to trickle onto the floor.

   "Hey you're getting it on the carpet!" Sam complained as if he owned my
study.  I ignored his comments and continued jacking off.

   David's stare was fixated on my cock, his fingers dancing on the sheets,
busy in a fantasy.

   "Touch what you like, I'm gonna cum soon." I said.

   David reached out immediately and grabbed at my swinging balls.  Jacking
off with his little fingers tickling my testicles was the final straw, and
I felt the pressure build.  Pointing my cock downwards toward the sheets I
let the heavy pulses take over as the hard rush of orgasm hit me.

   "Hah!" David's mouth stood agape and he quickly drew his hand back as I
fired thick ropes of cum onto the sheets, spreading lines of white, sticky
semen over a couple of feet of the bed.

   "Pretty messy huh?" Sam said, reclining on the chair.  He looked so cute
with his mussed up hair and floppy little dick.

   After the last few dribbles spattered onto the carpet, I let my cock
hang there and ooze the remainder of my load.  David grabbed the shaft and
held it, staring at the mess on the bed and back up at my cock.  He was
transfixed and entranced, fully indoctrinated into our secret pastime.  I
knew this kid was a keeper from the very beginning, but now there was no
doubt.
   - End