Date: Wed, 11 Jan 2012 09:56:56 -0800 (PST)
From: Beautiful Creamer <beautifulcreamer@yahoo.com>
Subject: Sissyboy Matchup (gay adult-youth)

Sissyboy Matchup
By Beautiful Creamer


Josh Pantydropper shook his head when his mother gave him the news.

Could she have really said what he thought she said?

She could.

"It's time you started dating, Josh.  My special friend, Carlos, and I need
some time together and it'll do us all good if you're dating while Carlos
and I are...talking about things.  You're plenty old enough to date."

Old enough?

Josh would be eleven in five weeks.

He hadn't even really thought about dating.  Though he was starting to feel
the rumblings of puberty in his pretty, pink testicle bag.

Josh knew that boys and girls..."did it"...to make babies.  Though "it" was
a concept still unclear to the boy.

Girls weren't looking in Josh's direction yet.  The ones who were looking
at boys were looking at the bigger, muscular, jock boys.  Especially the
older 12- and 13-year-old boys at their middle school.

Josh didn't get that kind of attention.  He was smaller.  Skinnier.  Not
really manly handsome.

Josh was pretty.  As pretty as the girls.  Prettier.

As pretty as his gorgeous mother.

All of which could have distressed him if he'd overthought it.

Josh didn’t.

He had plenty on his mind already.

His single mom was young and sexy.  Men were circling the house in packs.
And Josh knew that he was a cramp in her style.

But he never thought she'd be matching him up with some girl he didn't
know, handing him a $20 bill and dropping them off at the mall for eight
hours while Mom and her latest mantoy did the dirty.

That was how Josh envisioned his fate.

He couldn't fight Mom.

So he surrendered.  Working with her to fill out accurately the matchup.com
questionnaire about his likes and dislikes.  Even the age part.  Which Josh
figured would end things right there.  No reputable online dating service
would match a 10-year-old boy with anyone.

Wrong again.

Three weeks later, at four o'clock on a Saturday afternoon,
Mrs. Pantydropper gave her son the news.

“You have a date tonight, Honey.  And so do I.  So get ready.  Your
date will be here at 5:30.  And Dieter, my date, will be picking me up at
5:45.  Take a nice bath and put on the clothes I left on your bed.  Let's
go now.  Move it!”

Move it?

Josh was frozen with fear.

Matchup.com had arranged a date with Josh through Mom?

How was that possible?

What kind of girl would be showing up in 88 minutes?

And who was “Dieter?"  Wasn't Mom dating Carlos?

Mom could be quite insistent.  So Josh proceeded to his bathroom and took
the ordered bath.  Filled with dread and confusion, the boy then wrapped a
towel around himself to go to his room and get dressed in the clothes Mom
laid out.

Until he saw them.

It had to be a mistake.

No girl, addled enough to use an online dating service at age ten or not,
would want to see Josh in that!

Mom had purchased an ensemble that screamed "Sissyboy!"

Tiny, denim short-shorts that would barely cover Josh's bottomcheeks.  A
frothy-pink baby tee that was at least a size too small.  Sandals with
thin, girlish straps.  And, worst of all, a pair of what looked like the
kind of panties a girl would wear.  And they were pink!

Josh's knees were weak with fear!

Mom wanted to humiliate him in front of a girl.  But why?

Josh rarely confronted the Pantydropper matron, but enough was enough.

Still wearing the towel from his bath, Josh knocked on Mom's door, waited
for permission, then entered.

Josh loved his Mom, Amber Pantydropper.  The sight of her in full feminine
battle array still stunned him now and then.

She was seated on her vanity stool in front of a large mirror that was
probably enjoying what it had for reflection.

The 29-year-old woman was stupefyingly beautiful.  Her magnificent visage
was framed by a thousand natural-blonde curls.  Men would gaze upon her
full, red lips and instantly envision the presence of those lips on their
cocks.

Mrs. Pantydropper was dressed only in her lingerie.  Lacy, black bra that
was straining to contain her 44-DD breasts.  Black, seamed,
fully-fashioned, reinforced-heel-and-toe stockings that encased her long,
shapely legs.  Matching panties and garter belt.  An ensemble that would
probably inspire...Dieter, was it?...to unmatched achievements later that
evening.

Josh sighed.  His Mom was so beautiful.  The boy imagined what it would be
like to be the object of so many men's sexual desire.

Josh knew he would never have that in his life.  From girls, anyway.  And
the thought had never formed of men desiring him in ways that men desired
his Mom.

"Yes, Honey.  What is it?" Mrs. Pantydropper asked her son as she
interrupted the finishing touches of her makeup application.

Josh decided to play the sniffle card.  "Mom," the boy sobbed, "I can't put
those clothes on.  I couldn't leave the house like that, let alone go on a
`date' dressed that way."

Mom smiled.  “Of course you can, Honey.  And you will.  The people
at matchup.com suggested those clothes for maximum success on your date.
Now run along and get ready."

One last try.  "But, Mom.  I'll be humiliated.  No girl would want to be
seen with me dressed like that.  Who is this girl anyway?"

Mom patted her son on the head and said, "All in good time, Josh.
Don’t be so impatient.  Scoot.  Now!"

Having no apparent choice, Josh surrendered.

He dried his hair and combed it.  Then slid on the panties.

Which felt surprisingly good.  Silky.  Rubbing nicely against his boy's
things.

Then the short-shorts.  Which looked even shorter on him than they had
looked on the bed.

Ick!

He was showing double bumcheek.

And while he had very lovely bumcheeks, Josh was going to be mortified to
show them off to his "date."  And everyone else they would see.

Maybe they could go to a dark movie.  A really bad, long movie with almost
no one in the theater.  Then skitter home to end the whole fiasco.

Josh put on his shirt and strappy pink sandals and looked at himself in his
full-length mirror.

Which was mostly depressing, except that...

Josh saw something in that mirror that he didn't expect at all.

Josh was hot.  Really hot.

The wrong kind of hot.  The most wrong kind of wrong hot.

But hot.

Some of the people Josh saw that evening, Josh concluded, would see that
wrong hotness as well.

Which was 90% terrifying and 10% thrilling to Josh.  Who wanted to be
desirable.  But certainly not in a faggy, sissyboy way.

Josh pondered this and that for a while until he heard, "Josh, your date's
here."

An icepick of fear stabbed Josh's heart.

He took a huge breath, disconnected himself from the mirror, and slowly
walked downstairs to meet his date.

Where was she?

Mom was standing in her big heels and little black dress, talking to a man.

Who had to be Josh's date's father.

The man was the right age for that -- 40-ish. Too old to be Mom's
boyfriend.  She liked them aged 18-23.  Prime spunking years.

Good, Josh thought.  The girl's father would see Josh tarted up, recognize
that he was bad for his daughter, and abort the mission.  Mom would call
one of the regular babysitters, who would sit and text all night while Josh
watched TV and played video games and that would be that.

But there was a disturbance in the Force.

Josh could sense it.

The man was standing two feet from Mom and he wasn't aroused by her.  No
lump in his pants.  No fawning admiration.  No dreamy smile aimed in her
direction.

Oh no.

The man was turning his head and looking at Josh.  Giving Josh that dreamy
smile that Mom always got.

And Mom was saying, "Oh, there you are, Josh.  This is Mr. Longthrust, your
date for tonight.  Say hello, Honey."

Josh couldn't say anything except emit a loud gasp.

Through the frozen fog of fear, Josh could hear Mom saying to
Mr. Longthrust, "...my emergency number, but I trust you won't need it.  I
see you brought a bag with everything you need.  Dieter and I should be
home around ten tomorrow morning.  I'm sure you and Josh will get along
very well on your date."

Then Mrs.  Pantydropper kissed her son-statue goodbye, shook
Mr. Longthrust's hand and scooted out to the curb where Dieter was waiting
with both the car's and his motor running.

Leaving her ten-year-old, virgin son alone for 16.5 hours with a
dating-service-avowed boylover.

Josh's every corpuscle was alert to opportunities for flight or fight.

Neither would be necessary.

But Josh didn't know that yet.

"I'm very pleased to meet you, Josh," the man said to the boy.

Josh's eyeballs unlocked just enough to allow the boy to see
Mr. Longthrust's hand extended for a shake.

Reflexively, Josh took the crazy pervert's hand and shook it.

Oh my!

The man's palm was sweaty.  He was as nervous as Josh was,

Somehow that relaxed Josh just enough that he was able to breathe without
mechanical assistance.

Why was Mr.  Longthrust, if that was his real name, nervous?

Men were nervous around Mom all the time but that was because she was so
gorgeous and sexy and desir...

Wait!

Did this man think that Josh was gorgeous, sexy and desirable?

Apparently so!

Josh was getting his wish.  But in the wrongliest wrongness of wrong ways.

Josh released Mr.  Longthrust's hand.  And waited.  Warily.

“Your mother told me you were beautiful,” the man said,
“and I saw the pictures she posted of you on the matchup.com web
site [WHAT PICTURES!?!?!], but you are just miles prettier than any
prettiness I could even imagine."

Josh blushed crimson at what was the greatest single compliment of his life
so far.

Which was not entirely unpleasant.

The boy knew he deserved praise for his beauty, but not from a man.  A man
who was probably figuring out a way to kiss Josh.  Right on the lips!  And
maybe even [gasp] try to do other stuff too.

Like the kind of stuff Mom and her men did on their dates.  When Mom would
roll in at three a.m. with her hair and makeup all messed and walking
stiffly. But really happy.

Well Josh wouldn't be one bit happy if this man tried anything with him.

But apparently, his "little man" had other ideas.

The man's praise of the boy's beauty had "stirred things up" a bit in
Josh's pubic area.  And despite all the boy's rational thoughts, Josh's
already tight short-shorts had tented.

Not a Barnum and Bailey's Big Top.  More like a pup tent.

But a tent.

A shameless tent.

Mr. Longthrust noticed.

The boy's blush deepened.

How would he ever survive the next 16.4 hours?  Maybe if he grabbed a
butcher knife, he could defend himself and his honor for a 16.4-hour
standoff.

Mr. Longthrust changed the subject.

"I'm not much of a cook.  But I thought we could go out for pizza.  Unless
you want to order pizza in.  Do you like pizza, Josh?"

How to answer that?

Josh liked pizza.  He didn't like going out in public looking like Miss
July on that year's sissyboy calendar.  Nor did he relish the thought of
staying in with Mr. Pervo all night.  What to do?

As Josh pondered his response, Mr. Longthrust said, "I want to thank you so
much for spending some time with me, Josh.  The computer at matchup.com
said we were perfect for each other, but you never know until you meet
someone.  I guess your mother told you that she was worried that you were
entering puberty and had no Daddy to teach you what a boy should know about
sex.  So I guess the computer sent me to be your stand-in Daddy."

There was a new wrinkle, Josh thought.  If it was true.

Mr. Longthrust went on.  "When girls reach puberty, they need a Mom to tell
them about menstruation and breast care and the nagging, manipulation and
emasculation of every man they meet.  Boys need to learn about their
changing bodies too.  And your Mom, who does your laundry, says you've been
having wet dreams for a couple of months now.  So it was time."

Did Josh have no privacy?

It was true.

He was ejaculating.  Involuntarily at first.  But then, three days earlier,
Josh had been in bed thinking about the girl he would be meeting if Mom's
date craziness ever came through.  He touched himself that night.  And it
happened. And then...

"Do you ever play with yourself, Josh?

The man was a mindreader.  And a nosy beast!

But maybe, just maybe, Mom was right about him needing a grown-up male
advisor at that time in his life.

So taking a small leap of faith, he answered truthfully.  "Just once.
Three days ago."

Mr. Longthrust beamed.

That was the icebreaker.

By his estimate, his manly rammer would be splitting this young beauty's
peach in less than three hours.

"Did you make boy's cream?”

Josh nodded shyly.  His face beet red and his cock at its full, glorious
4.27-inch stand.

"Did you enjoy it?"

Another shy nod.

"Of course you did, Buddy.  Every boy needs relief.  Your Daddy would have
told you all that.  I'm sorry you never has a Daddy.  But now we're going
to get you on the right path.  Did you use any kind of lubricant when you
were rubbing yourself down there?"

Josh looked puzzled.

Mr. Longthrust smiled.  "It's better with lubricant.  Even if you just spit
on your hand.  Wait just a minute.  I have some stuff right here."

The man reached into his bag and extracted a plastic bottle of "Slickyboy
Masturbation Cream" (a Spermbutt Industries product).

"This stuff is great.  Let me show you.  Are you circumcised?  [Chuckle] I
guess I'll see for myself in a second.  Let’s just pull these down.
Oh my! Nice panties!"

THE MAN HAD PULLED JOSH'S SHORTS DOWN!

EXPOSING HIS PANTIES!

AND JOSH HAD LET HIM!

It had just seemed so natural.  Mr. Longthrust was here to help Josh
mature.  Step one was better masturbation through lubrication.  Practical
exercise to follow verbal instruction.

Before Josh could form a proper objection in his mind, his panties were
down to his knees and Mr.  Longthrust was admiring the boy's stiffie with a
look and manner that, had Josh a better vocabulary, the boy would have
defined as "lupine."

Josh was alone and half naked in the house, for 16.3 more hours, with a man
whom he had just met and was smearing some creamy stuff onto his hand in
order to...

Oh!!

The man was running his strong, warm, slippery fingers all along Josh's
erect penis.  In ways that Josh had never imagined.

Nor had the boy ever imagined the delicious sensations he was feeling as
the man handled his precious parts lovingly and expertly.

Despite his usual good sense, Josh surrendered to the man’s
attentions.

The boy groaned softly as he felt his foreskin pulled this way and that.
And the rubbing of the exposed pink knob fired his libido in a way he had
never known.

Josh actually whimpered when the man interrupted his "molestation" to apply
more lubricant.

Then he was surprised to feel the man's relubed hand cuddling his
testicles.

Which was also incredibly thrilling.

The man even made a small joke.  "I was a basketball player in high school,
Josh.  A good ballhandler."

Josh wanted to snicker in socially dutiful appreciation, but he felt the
first delicious pang of an oncoming crisis.

The man recognized what the boy was feeling and returned his hand to Josh's
tender knob.  Reveling in the boy's squeaks and grunts until, 15 seconds
before the arrival of Josh's legshaker orgasm, Mr.  Longthrust did two
naughty things:

He entered Josh's bottomhole with the middle finger of his free hand.

And he leaned forward and kissed Josh -- right on his cherubic lips.

Josh screamed.

Not in fear.

In a lustful agony of delight.

Shooting his boy's cream in thick arcs.  All over his own belly and the
shirt of the fully clothed man whose tongue had just entered Josh's
startled mouth when he opened it to scream.

Ecstatically confused, Josh's brain desperately sought to sort out what was
happening to him.  The tongue in his mouth.  The [blush] finger in his
bottomhole -- the most confusing act of all.  Who knew that a violation of
one’s boyish anus would be so terrifyingly thrilling?

The man was a horrid beast for taking advantage of the boy.  Josh knew
that.  And he knew that many would see what just happened as stunningly
gay.

So why did it all feel so good?

So much better than anything he had ever experienced?

Josh's orgasm reached his toes.  He wiggled them to make sure they were
still attached.

Then he whimpered and grunted his way through the indecent reward for gay
behavior until only a feeling of perfect relief was left.

At which time, Shame and Guilt made their unwelcome appearance.

Mr. Longthrust knew them well.

He had met them on all his first dates with a boy.

They had met their match with Mr. Longthrust, however.

The man finished the kiss and said, "I've been wishing I could meet someone
like you all my life.  You're a perfect angel.  I hope you liked that.
There's lots more where that came from if you want it.  I'll be in your
room when you're ready."

At which point, he grabbed his bag and went upstairs.

Leaving Josh, naked from the waist down, stomach wet with sperm, chest
heaving with excessive breathing, to his choices.

Mr. Longthrust found the boy's room and went in.  Slowly, unhurriedly, he
undressed.  All the while thinking about the old joke about the young nun
who was seduced by a man.  They were both naked, lying in bed, having just
fucked and the enormity of her sin had just slammed into Sister Ann.

The man watched as his lover fell to her knees and begged God's
forgiveness.  Crying and sobbing, Sister Ann said, "Please forgive me,
Lord, for my two horrible sins!"

Puzzled, the man asked her, "What two sins?"

Her answer: "Well, we're going to do it again, aren't we?"

That was what Mr.  Longthrust was counting on with Josh.  Fear and loathing
at the "sin" he had just committed, but an irresistible urge to "sin"
again.

The man folded his clothes neatly and laid them on a chair.  Then he
extracted a fresh bottle of Spermbutt Anal Lubricant from his bag and laid
it on Josh's nightstand.

Mr. Longthrust sat on Josh's bed.  Naked, hairy, erect and expectant of
Josh's imminent arrival.

He didn't wait for long.

Josh had considered his options.  The most "practical" being to get dressed
in his panties and short-shorts and make a run for it.  Perhaps to the
police station.  Where he would report Mr.  Longthrust and his Mom.  Then
watch as they were hauled off to the slammer.

Then he would live with a foster family for seven years or so.  In seven
years or so, Josh would find a girlfriend who would do some of those things
Mr. Longthrust had done so well moments earlier.

Seven years?

Or right now?

Hmmmm.

Mr. Longthrust watched the door.  And smiled to himself as he saw Josh peek
in, then withdraw when he saw the man's hairy nakedness.

Seven years?

Or right now?

Josh chose right now.

Tentatively, the still-half-naked boy entered his own bedroom.  Shyly
avoiding eye contact with his ravager-to-be.

While getting a good look at the man's toned body and massive cock.

Oh!

Was it too late to run?  He could just...

"I'm glad you joined me, Josh," Mr. Longthrust said.  “You're my
every dream come true.  And I want to be yours.  Let me help you out of
that shirt."

Docilely, Josh raised his arms and allowed the man to remove his last item
of clothing, the sandals having been kicked off before he climbed the
stairs.

So they were both naked.

And Mr.  Longthrust was gently seating the boy on his hairy lap.

They were kissing again.  Open-mouthed and hungrily that time.  Both fully
into it.

Josh felt Mr.  Longthrust's erect cock rubbing his thigh and, without
considering further consequences, he laid his soft, warm hand on the man's
stiff beast.

Mr. Longthrust groaned in appreciation.

Which delighted Josh.

And the ice was completely broken.

Man and boy kissed and wanked each other slowly.  Making it all last.
Pulling foreskins just the right way for maximum pleasure.

Josh felt his pleasure warnings and welcomed them.

Mr. Longthrust felt Josh feeling his pleasure warnings and stopped
pleasuring him.

Which made Josh whimper, until...

"I'm not wasting any more of your delicious cream, Baby.  Stand up and face
me.  That's it."

What was the man doing?

He was slicking up the three middle fingers of his right hand with some
stuff from a new bottle.

Then, as the man stayed seated, Mr. Longthrust was positioning the standing
Josh right in front of him.

"You're going to like this a lot, Sweetie," Mr. Longthrust said.

And then he took Josh's cock into his mouth and began to lick and suck it!

Josh squealed with surprised delight.

He had never felt anything half as good in his life.  And then it got
better.

Way better.

Mr. Longthrust entered Josh's anus with his lubed middle finger.

Still rolling his tongue over the boy's exposed knob, the man found the
boy's prostate.

No one had ever touched Josh's prostate.  Josh didn't even know he had a
prostate.  And no one had ever sucked his cock.

The effect was nuclear.

With additional megatons when Mr. Longthrust slid the other two fingers
into the Forbidden Zone.  And began to prostate-massage and cocksuck in
rhythmic earnest.

Josh's testicles detonated.

As the boy emitted both a loud squeal and a creamy spurt.  Right into
Mr. Longthrust's delighted mouth.

Josh didn't know such pleasure was possible.

It was so intense, it was almost painful.

The boy shuddered and spasmed as he shot his seed into his man's throat.

He was exhausted.  Yet eager for anything the man would propose.

In fact, when Josh became capable of rational thought, he realized that,
rather than wait for the man's next move, it was time for Josh to do
something for Mr. Longthrust.

But what?

He decided to show Mr. Longthrust that he was "giving himself" to him.

Best way to signal that would be to get onto his knees.

Between the seated man's legs.

Which brought Josh eye to eye with a very large, very stiff object.

A pearl of clear liquid was oozing from the man’s peelips.

Josh knew that it was the stuff that came out when one gets aroused.

It pleased Josh that Mr. Longthrust was fully, almost agonizingly aroused
by being with Josh.

Maybe he and Mom weren't that different after all.

In for a penny, in for a billion dollars, Josh stuck his tongue out and
licked the liquid off the man's pouting peelips.

Which wasn’t half as yucky as it could have been.

Mr. Longthrust's nice, deep moan made it a pleasure for Josh too.

The kneeling Josh pushed his luck.  He gave the man's cockhead a nice,
all-over suck, removing his mouth with a loud "pop."

Mr. Longthrust liked that too.

Experimenting further, Josh used his tongue to "polish the knob" over every
hot pore, then added a bonus bit by cuddling the man's fat, hairy balls as
he tongued his cockhead.

That, as little extras often do, did the job.

"Oh, shit!" the man called out as he lost control of his "cargo."

Josh wasn't allowed to use words like that, but he didn't blame
Mr. Longthrust for saying it.

The things Josh and his date were doing were pretty exciting, and one could
be excused for minor transgressions like spontaneous swearing.

But attempted drowning of one's cocksucker was a more serious offense.

And Mr.  Longthrust was fortunate to avoid indictment on that charge.

Josh choked as he suffered the first hot blast of manly seed into his
mouth.  He withdrew reflexively, then felt blasts numbered two through
seven coat his face and chest, then dribble all the way down to the pillow
he was kneeling on.

Men, apparently, make a lot more sperm than boys do.

To his surprise, Josh wasn't put off by any of that.  He looked at
Mr. Longthrust's sperm deluge as an expression of his manly admiration for
Josh's beauty, charm, and growing capability as a lover.

And swimming in sperm was kind of sexy -- not yucky at all.

It appeared that Mr. Longthrust shared that view, since he had drawn Josh
to a standing position, laid him oto his back on the bed, and covered him
with kisses all the way to each pretty toe.

That was cool!

Josh really liked when Mr. Longthrust licked and sucked his boyish nipples.

Unlike his prostate, Josh had always known that he had nipples.  He just
didn’t know until that Saturday evening WHY he had nipples and a
prostate.

So much to learn.

But Josh was pretty sure that anything else he and his "manfriend,"
Mr. Longthrust, did that evening would be variations of wanking, kissing
and cocksucking.

Which was a delightful prospect to the newly awakened lad.

But the best was yet to come.

After a delicious half-hour of surrendering to all-over kisses, Josh was
hard and needy.

But how to ask Mr. Longthrust for "relief" without seeming "slutty?"

Relief was not on the man's immediate agenda.

"I'm going to call for pizza.  We can get cleaned up, including changing
these sheets, have our dinner, then see what else you might like.  OK?"

Well, it wasn't fully OK to Josh.  He would have rather had his cock sucked
than eat pizza.  And cleanliness was still not his highest need.  But the
man was the man.

"OK, Mr.  Longthrust," the sweet angel said.  "Baggiagalupe's has the best
pizza and I like sausage.  On my pizza." He giggled.

Double-entendres are the most fun when you're ten, almost eleven.

Mr. Longthrust smiled, kissed Josh on the lips, and ordered an extra-large
cheese and sausage pizza for delivery.

"It'll be here in 35 minutes, Honey. Just enough time for a nice shower.
You go start the water and I'll change the sheets.  Your mother left us
three clean sets, bless her."

Josh winced.  He wasn't happy that his mother thought he was such a
sissyboy slut that he would stain the sheets three times.  But he was eager
to stain them three more times at least.

Josh got the shower water just right then stepped in.  He would hurry so
that Mr. Longthrust would have plenty of time to shower before the pizza
delivery man...

Whoa.

Mr. Longthrust was getting into the shower with Josh!  They were both naked
and were soon erect.

Another sweet surprise.

Two washcloths were well-soaped and there was lots of kissing and cuddling
and fingers in Josh's bumhole.

But the man stopped short of making Josh cum.  And didn't cum himself, even
though naughty Josh slid a naughty finger into his man's bumhole during one
passionate shower kiss.

Bummer.

Josh was a bit heated up and unsatisfied after they dried off and padded
downstairs naked.

Mr. Longthrust hastily put on shorts and a tee when the pizza came, then
got naked again as they ate.

The pizza was good.  And so was the conversation, mostly about Josh's life,
likes and dislikes.

But Josh wanted more.  Soon.  After all, Mom would be back in only 14.3
hours.

After the last morsel was eaten and cleanup was underway, Mr. Longthrust
asked, "Do you know what `fucking' is, Josh?"

A startling question, even in the midst of what they had been doing.

"Fucking is when a man puts his penis into a woman's vagina and they make a
baby," the boy answered with schoolbook precision.

Mr. Longthrust smiled broadly.  "That's one kind of fucking, you're right,
Sweetie.  But there are more kinds.  Men don't just fuck to make babies.
They fuck for fun.  And they don't just fuck vaginas.  They fuck women's
bottomholes.  [pause] And boys' bottomholes."

Josh saw where this was going.

And it scared the poopie out of him.

Did Mr.  Longthrust intend to try shoving that colossus into his tiny bum?

Oh!!!

That sounded awesomely dirty!  Thrillingly sexy.  And life-threatening.

If Josh hadn't been so needy for relief at that point, he probably would
have run to his room and locked the door.

But the notion of "being fucked" seemed like a way to please his man as he
pleased himself.

Still, he had to ask.  “Does it hurt?"

Mr. Longthrust smiled, sat, and drew Josh to his lap.

"I'm afraid so, Baby.  But only at first, I understand.  Then it's pure
pleasure for both of us.  And I really want to make you happy."

Josh was beginning to think that he wasn't the first boy Mr. Longthrust had
ever "dated."

But he trusted Mr. Longthrust.  A man would never lie just so he could fuck
someone, right?

So he kissed the man's lips and said, "Whatever you want, Mr. Longthrust."

And thus Josh put his ass into Mr. Longthrust's hands.  And cock.

The naked couple retired to Josh's room once again.  And the preparation
began.

"I'm going to get you ready in two ways that I know you'll like, Baby,"
Mr. Longthrust said.  "I'll just lie on my back and you just kneel, facing
my feet, straddling my shoulders.  That's it, Honey.  Just lower your bum
down and sit right on my face.  That's it.  MMMMM!!!"

Oh my goodness!!!!!!!!!!!!

Mr. Longthrust had his tongue up Josh's bumhole!!

Licking it out!!

So nasty.

So exciting.

So dirty.

So thrilling that, after grunting and squealing his way through five
minutes and 36 seconds of expert, loving analingus, Josh shot his boy's
cream all over Mr.  Longthrust's hairy chest.

Which pleased them both.

And began Josh's real education about the delights of the anus.

Josh eased off Mr. Longthrust's face after his shudders subsided and
offered to suck his man's cock in gratitude.

"No thank, you Sugar," Mr. Longthrust said.  "I'm saving that stiffie for a
bigger occasion.

Gosh, Josh thought.  Did 40-year-old men need to husband their erections?
Josh seemed to have one all the time.

Hmmm.

Anyway, the lovers lay side by side, kissing deeply as Mr. Longthrust lubed
three fingers with Spermbutt Anal Lubricant, then slid them into the boy's
well-eaten asshole.

Josh cried out as the man found that prostate thing again and tormented it
as they kissed.  Making the boy puddle-weak and coaxing yet another creamy
load from his aching balls.

No one has ever had a date as good as this one, Josh thought.

But the first bump was about to appear in the date's superhighway.

Mr. Longthrust had prepared the boy's anus as well as he could and he meant
to fuck him or expire in the attempt.  But as a man who had introduced 26
boys to the joys of anal sex, he knew what was imminent.

The man positioned the boy face down on the bed, then slid three pillows
under his tummy.

The position was right.  The boy eager for his first fucking.  Lubrication
and dilation were accomplished.  Check, check, check and check.

What a beautiful, loving boy, Mr. Longthrust thought as he lined up his
cock with Josh's gorgeous asshole.

What a privilege to take his virginity.  But wasn't it only fair that he,
the founder of matchup.com, would have first choice of all the boys whose
moms sign them up to his service?

Best investment he ever made, Mr. Longthrust reminded himself.

He grabbed Josh's hips firmly -- critical to prevent escape -- and pushed
hard.  Lodging the head and two inches of shaft inside the sweet canal.

Wait for it.

The moment of shock and then the scream of near-death agony.

There it was.

With the boy distracted by his own scream, Mr. Longthrust shoved the other
six inches into paradise and was in to the hairs.

The man held the boy's hips firmly as he screamed and bucked and tried to
get away.

To no avail.

"It's OK, Baby," the man said as he leaned forward and kissed Josh's neck.
"I won't move it yet.  Just letting you get used to it.  There we are."

The fires in Josh's bowels were subsiding a bit.  And the man had reached
around and was wanking him very nicely as he said sweet things about his
beauty and charms.

Soon the pain was bearable.

And then it was gone.

Replaced by a lovely feeling of pressure on that prostate thing.

Josh sighed with pleasure as Mr. Longthrust proceeded to active measures.
Running his thick log back and forth in Josh's stretched boypussy.

Josh was pleased to hear Mr. Longthrust's grunts and moans of pleasure as
he fucked the young beauty.

Josh was every bit as beautiful and desirable as his Mom.

Which would give him the confidence he needed to get through life.

Though the rest of his life wasn't what was on his mind at that moment.

The boy felt yet another orgasm brewing.  A big one that time.
Prostate-centric.  Only pillowcase friction on his penis.

Mr. Longthrust had picked up the pace as well.  Which told Josh that the
man was about to shoot a big load of that stuff he had shot on Josh's face
inside his bottom.

The thought of that naughty nastiness pushed Josh off Cum Cliff.

The young angel squealed and squirted.  Though all he could manage was a
few watery drops, his spasms were severe.

Mr. Longthrust was delighted that he had given the beautiful boy such
first-fuck pleasure.  Which set him off.

Through an orgasmic haze, Josh felt his bowels being filled with sperm.

And a good time was had by all.

Five minutes later, Josh lay in Mr. Longthrust's loving arms.

Both their chests were heaving.  Both cocks were limp and drooling.  Josh's
asshole was drooling sperm.

What a great first date this was.

Ten minutes later, Mr. Longthrust said, "I think you like being fucked."

Josh giggled.  "I like it all, Mr.  Longthrust."

And to prove it, he slid down and took the man's limp, poop-coated,
cum-dripping cock into his mouth and nursed on it, rather than sucked it.

Both lovers fell asleep at that, even though it was only 9:12 p.m.  And
12.8 hours until Mom came home.

Josh awoke at 12:37 a.m. with a raging stiffie and an urge to do something
with it.

Mr. Longthrust was snoring lightly and his manly rammer was at half-staff.

Time to raise the flag.

Josh located the bottle of Spermbutt Anal Lubricant and lubed three fingers
of his right hand with it.  Then he entered his man's anus with his tiny
fingers as he capped the man's cockknob with his wet mouth.

Mr. Longthrust awoke in what had to be the most pleasant way a man can
awake.

Oh my.  The little scamp liked anal games with his man.  Maybe on their
second date, he'd offer Josh's cock his hairy hole.

Should he let Josh suck and swallow a nice, thick,
three-hours-in-the-making load?  Or should he call a timeout and shove his
new stiffness into that heavenly channel?

He decided to be lazy.

"That's so good, Baby.  So sweet and loving.  So generous.  Move your
fingers left.  That's it.  Right there!  Oh!"

Mr. Longthrust "endured” the sweet agony of a simultaneous
knob-licking and all-out prostate assault.

Josh enjoyed it almost as much as his man did.

Giving pleasure can be as much fun as getting it, Josh discovered on his
first date.

The boy was more prepared that time for the inevitable sperm tsunami.

He managed to swallow a million or so spermies before another million
dribbled out of both sides of his pretty mouth.

Mr. Longthrust drew him for a deep, long kiss, then had Josh straddle his
shoulders, kneeling in a position where he could fuck the man’s
mouth as the man finger-fucked the boy's anus.

That was very nice indeed!

When all that was duly entered into the history books, Mr. Longthrust
insisted on changing the sheets and showering yet again.

Which gave the man additional time for recovery.  Since he intended to give
Josh's anus another nice fucking before they went back to sleep.

And a very nice, clean-sheet fucking it was.  Long and slow.  Thirty-four
minutes of in and out.  With the boy on his back, on the bottom, calves on
Mr. Longthrust's shoulders.

There was slight pain that time.  But it passed quickly.  And the fucking
that followed was one for the ages.

The innocent sheets suffered.

OK.

Time for another snooze.

Which ended when Mr. Longthrust awoke at 4:28 with a stiffie and a dream.

He awoke Josh with kisses and, lying on his back, eased Josh down until the
boy was sitting on the man's cock.

They kissed and fucked for 43 minutes that time and, when they orgasmed,
stayed in position until they fell asleep again.

Until 8:24.  Only 1.6 hours until Mom's return.

Mr. Longthrust sucked Josh to a creamy conclusion, then put him on all
fours and doggie-fucked the boy until he screamed out his love for
Mr. Longthrust.

"I love you too, Baby," the man said truthfully.  But in truth, he loved
just about every boy he fucked.  "I'll ask your mother for another date.
Maybe next Friday."

Friday!?!?!?!

Josh couldn't wait for sex until next Friday.  How would he ever...

And then it hit him.

Josh could have sex any time he wanted.  With just about any man...or
boy...he wanted.  He would just have to wiggle his bottom and bat his eyes.

Which was exactly what he did with Mr. Longthrust at 9:01 to eke out one
last fuck before they hurriedly showered and changed the sheets one last
time before Mom's arrival.

Life is good for a beautiful sissyboy.


I welcome your comments at beautifulcreamer@yahoo.com.

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