Date: Mon, 8 May 2006 20:27:59 -0700 (PDT)
From: Thomas Gaige <togaige@yahoo.com>
Subject: Sam's First Times - Chapter 6

DISCLAIMER:  The following story is FICTIONAL.  It contains depictions of
sexual activities between teenage boys.  If you are not over 18 years of
age, or if you find this type of story offensive, or viewing this
material is illegal where you are, then please DO NOT READ IT!  If you
choose to read it, then - I hope you enjoy it!

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                        Sam's First Times

                   Chapter Six - Anal Exploration

Not long after Sam discovered how pleasant using lubricants could be
while he masturbated, he became more curious about his asshole.

As he lay in bed jacking off one morning after Cindy left for work, using
a handful of baby lotion on his dick, and a glob of vaseline on his anus,
he began to notice that whenever his sphincter contracted, if he rubbed
on it a little harder, his finger would sink into it a little, as his
muscle relaxed again.  Sam found this to be a pleasant sensation.  Of
course, he began pressing on his hole then, and found it felt very nice
indeed.  Naturally, because he was lubricated with vaseline, and was
continually pressing harder and harder on his pucker, as his muscle
relaxed one time, his finger suddenly slid right through his anus, up
into his rectum a little way.  Sam's eyes shot open with surprise.  He
was surprised that he'd actually pushed his finger up inside himself all
the way, and that it didn't hurt.

Sam's right hand stopped moving up and down his stiff, slick rod, as he
lay there with his finger still up his ass, squeezing it gently by
contracting and relaxing his anal muscle.  Sam was surprised that his
finger being up his ass didn't hurt, and at how strong his ass muscle was
when it squeezed his finger.  He tried squeezing it as tight as possible
then, and smiled at the sensation.  Afterward, he pushed his finger a
little further up inside himself.  Gently, he felt around at the walls of
his rectum with his fingertip.  It felt softer than he'd thought it
might.  It also surprised him that it felt good to have something poking
around inside him.  Curious now, he pulled his legs up a little more, to
open his ass cheeks fully, and pushed his finger all the way inward then,
as far as he could.  Then, as he felt around with it, he inadvertantly
rubbed against where his prostate gland touched his rectum, and was
shocked by the shiver of pleasure that shot through him.  He didn't know
what it was he'd touched - but he knew he liked the feeling it gave him.

Sam pulled his finger out a little, then pressed it back inward, again
rubbing the spot that had felt so good, and let out a soft, surprised
grunt from the pleasure he felt.

Smiling, Sam slowly began sliding his finger back outward, then pushed it
back up inside him again, again pressing on his prostate.

"Damn that feels good!" he murmured.

Smiling to himself, Sam began sliding his finger in and out of himself in
a more steady, rhythmic fashion then.  After a minute, he reached for his
cock again and began jacking off again too.  The combined feeling was
fantastic!

"Ooohhhh!" he gasped as shivers of pleasure like he'd never felt before
rippled through him.

As the level of his pleasure built, he closed his eyes, and
involuntarily, both his hands began moving faster.  He jacked himself off
faster, and finger-fucked himself at the same pace as well.  As he did
his orgasm began forming.

Shortly Sam was shaking and gasping with delight as waves of pleasure
resounded through his body, and his orgasm continued building.

All too soon, Sam was at the point of his climax.  He strained to hold
back, and for a few seconds, he was able to control himself.  But then
suddenly, the pressure inside him was too much to bear.  With a soft
high-pitched cry, his body spasmed, and he felt his sphincter clench his
finger tightly, as he ejaculated a thick glob of gooey semen, which flew
through the air, and landed on the right side of his nose, and streaked
down his face, over the corner of his mouth.

"Awwwwww!!!" he gasped a moment later as his asshole clamped tight around
his finger, and a second rope of cum shot out of his dick, landing on his
chest.

"Mmmmmmm!!!!" he mewed, a second later as he spasmed with joy again.

Sam had never experienced as much sexual pleasure as he was with this
particular orgasm.  As his body continued pulsating with waves of
passion, in the back of his mind, all he could think was "I can't believe
how fucking awesome this is!"

When Sam's orgasm finally ended, he slid his finger out of his rectum and
lowered his legs.  He continued sliding his hand slowly and gently up and
down his shrinking dick though, knowing there'd be a last drop of cum
that would ooze out of him.  When it finally did, a moment later, a
shudder passed through him, then he lay quietly, his hand wrapped around
his penis, breathing heavily, luxuriating in the warmth and relaxed
feeling he was experiencing.

"Son of a bitch that was fantastic!" he muttered, smiling to himself, as
Felix got up and walked up to him and began licking his spunk off him.

A while later, Sam got up and showered.  He couldn't get his mind off his
new found knowledge that he could also get pleasure from rubbing a spot
inside his asshole.

Sam contemplated the fact that it felt good sticking his finger up his
ass for the next hour or so.  By then of course, he was horny again, and
ready to try it again.

"It felt better the more I stuffed my finger inside," He thought to
himself.  "I bet if I had something a little bigger, it'd feel even
better!.... but what?"

Sam searched through the house then, looking for something cylindrical
and smooth that wasn't much bigger than his finger, which he could try
stuffing up inside himself.  Eventually, he found a few things he thought
he could try.  He had a long handled ladle from the kitchen, which had a
smooth, rounded, plastic handle.  He also found a smooth handled
screwdriver, although he wondered if the handle was a bit too fat maybe.
The bottom of a candle looked like it might work.  And finally, he'd
noticed one of Felix's long, cylindrical rubber toys.

"That might be the most fun," Sam said, smiling at the spherical end it
had.

Sam took the four items he'd found and returned to his bedroom.  Quickly
he stripped, and laid down on his bed.  He decided to try the candle
first, as it looked the thinnest.  Quickly he greased the end of it, then
drew his legs up, and pointed the greased end of the candle as his butt.
Lowering it toward himself, he hit a little above his anus, so he
adjusted it slightly so that it was pressing right on his pucker.  Slowly
then he began pushing.

Not realizing that if he pushed against the candle with his muscle that
he'd slide in easier, he felt resistence, and ended up pushing harder.

"AWWWW!" he cried, when the candle finally pressed through his tight
sphincter.  "Shit... how come it hurt?"

Although it'd hurt going in, once it was there, after a few seconds
passed, it felt OK.  Once he'd fully recovered, Sam began sliding the
candle up inside himself.

"Shit!" he thought.  "I wonder how far in it'll go?"

Suddenly, as he continued pushing, he hit what felt like a solid wall.
Up inside himself, he felt the candle run into something in his body.
Looking down, Sam realized he had a lot of the candle inside himself.
Curious, he held his finger and thumb up against his pucker, squeezing
the candle.  Then, he slid the entire thing out of himself.

"Fuck!" he said, his eyes growing huge when he saw how much of the candle
had been inside him.  He also crinkled his nose.  It smelled a little
shitty, and there was some shit stuck to the end of the candle.

"Might as well try these other things," he said.

Sam tried the ladle handle next.  He managed to get the entire handle
inside himself, but the cold metal part of the handle felt funny being
left sticking out of his asshole.

"Awww!!!  Too fat!" Sam gasped, as he tried to push the screwdriver
handle up inside himself.

Finally, Sam picked up Felix's rubber toy.  He greased it up good, them
placed the round 2" diameter ball end of it against his rosebud.  A
gentle push, and the toy slid easily through his ring muscle.  The ball
felt good inside him, and the 1" cylindrical shaft wasn't too thick for
his hole.

"Mmmmm!!!" Sam murmured, as he shoved the rigid, yet somewhat flexible,
toy deeper inside himself.

"OH YEAH!" he gasped, as he felt the rubber ball on the end rub against
the spot that felt so good.

Grinning, Sam began to slide Felix's toy in and out of himself, pulling
it all the way out to when the ball end of it hit the inside of his
asshole.  Then he pushed it all the way inside himself, as far as he
could, each time, rubbing against his prostate, and sending a thrill
through his body.

"Mmmmmm!!!" he moaned happily, as he stopped and reached for his tube of
hand lotion.  He squirted some into his hand and resumed fucking himself
with his new-found dildo.  At the same time he began masturbating again.

"Fuckkkkk!!" he gasped, as he worked on himself.  This jack-off was even
better than the one he'd had earlier, when he'd used his finger up his
ass instead!

Moaning happily, with a look of extreme passion on his face, Sam slid
Felix's toy in and out of himself, and slowly masturbated.  It was the
singular most pleasant experience of his life to that point!

Slowly, Sam felt his orgasm building.  He worked on himself slower than
usual, hoping to prolong the pleasure he was feeling as long as possible.

After a minute though, he couldn't hold back any longer.  Groaning, he
sped up both hands.  Soon his fist was flying up and down his stiff,
greased rod, and Felix's toy was slamming in and out of him, rubbing back
and forth over his prostate.

By the time Sam's orgasm hit, his body was trembling in an almost
seizure-like fashion.  His mouth was open as he gasped for breath, and
his eyes had a wild look in them.

It was a good thing Cindy wasn't home when his orgasm hit, because Sam
wasn't able to control himself.  He cried out loudly as the first spasm
of joy washed through him, and his dick erupted like a volcano, spewing
the biggest gush of semen he'd ever ejaculated.  He blew his load so
forcefully, it hit the headboard of his bed, with a bit of it streaking
over his pillow, and the end of the string, landing in his hair.

"Fuck!" he gasped a second later, jerking passionately, as he blew a
second load, that landed on his cheek and ran down to his ear.

"Awwwww!!!" he groaned, as his third spasm sent a glob of cum flying in
an arc, which landed on his right shoulder.

"UUmmmmmm!!" he grunted, squirting more jism onto his chest.

"Ooohhhh!!!" he groaned more softly, as his orgasm began to fade in
intensity.  His ejaculate his his belly that time.

Sam's orgasm faded quickly then.  He spasmed a couple more times,
spraying dots of semen onto his belly, and oozing a last larger glob,
that ran down over his thumb and puddled in his pubic hair.

As his orgasm ended, he pulled Felix's toy from his ass, and lowered his
legs.

"Fucking Christ!" Sam whispered, gasping for breath, his eyes wide open
with delighted surprise.  He couldn't believe how awesome an orgasm could
feel.

Sam rested for a few minutes, then let Felix lick him clean.  After he'd
showered, he washed off all the implements he'd used as dildos, and put
them back.  Felix's rubber toy he put in the drawer of his night stand
though.

"That's mine now!" he said, smiling to himself.

From then on, whenever Sam had the opportunity to masturbate leisurely,
he usually always greased up Felix's rubber toy and fucked himself with
it as he pleasured himself.  When he did, his orgasm was always bigger
and better than when he didn't...

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Watch for the next chapter of this story to be posted shortly...