Author's note: this is actually an older story that I wrote almost 15
years ago. A gentleman who has been encouraging me to write these sissy
stories suggested that I post some of my older work online here, so that
all of my stories would be available to read in one place.
It gets a little dark, and I can see how my tastes have changes since
2003, but I still enjoy the story. I hope that you will as well.
Enjoy;
Sissy Michelle
Cheerleader's Panty Boy
Steve began crossdressing when he was a young teenager. At first he liked
to masturbate into his sister's panties, but that quickly progressed to
the point where he was masturbating while wearing his sister's panties.
By the time he was a sophomore in high school and his sister Staci had
moved away to college, Steve would lock himself in his room when his mom
was off at work. He'd dress up fully, wearing panties, bra (he and poor
Staci were roughly the same chest size) plus a frilly dress that Staci
had left behind when she moved out and a pair of his mom's pantyhose that
he'd rescued from the trash.
Steve would sometimes sneak down to the kitchen and steal a carrot from
the vegetable bin. Then back up to his room where the carrot, liberally
greased in Crisco, would be forced into Steven's bottom while he jerked
off. It never took more than just a few pokes by Mr. Carrot-dick and
Steven was shooting off into his panties.
Sometimes Steven wondered if he was gay or something, and the thought
really disturbed him, but he justified his actions saying that everybody
jerks off. And as long as he didn't do it with a real man, a carrot
wouldn't make him into a homo.
His dress up sessions became more frequent and more daring. Once, when
his mother was away for the weekend, Steven had gone all out. He painted
his fingernails and toes. It was a dark-red mess; splattered all over his
fingers, but Steven thought the red nails looked extra sexy stroking up
and down his cock. He had chosen a larger carrot this time, and he loved
the way it's bumpy ridges made him feel.
In a fit of passion, Steven turned the vegetable around and shoved the
thick end inside him. He winced a bit, but there was no denying that the
thicker end felt better than the thin pointy one. And it made him feel so
sexy! Steven was furiously pounding away at his cock and bottom, and he
was so caught up in his fun that when he reached his climax, Steven
straightened up and the carrot snapped off inside him.
At first he panicked, thinking that he'd have to go to the hospital and
everybody would think he was a queer! But then he realized that the
carrot wasn't stuck, although it did make him feel all nice and full.
Usually after an orgasm, Steve would clean up and put everything away,
but this time with the carrot still inside, he just didn't want to stop.
So he sauntered to the bathroom and helped himself to some of his mom's
makeup. Lipstick, mascara, blush and blue eye shadow. He looked like an
over-made up whore, but Steven loved the look, especially as he stroked
his cock for his second and third orgasm of the past fifteen minutes.
After that, Steven decided that he would be a little more daring.
Steven started wearing his sister's stolen panties to school twice a week
on the days he didn't have gym. He thought that nobody had noticed, but
Mary Ramses had spied his visible panty lines one day while he stood in
front of her and a few of her friends in the lunch line. She smiled as a
plan formed in her head, and then she tapped her prey on the shoulder and
asked him to grab a lunch tray for her.
When Steve reached up to get the tray his shirt rode up and Mary was
looking directly at his waistband. Sure enough, there was just a sliver
of pink material showing through. "Thanks for they tray," she said and
then leaned forward and added, "Nice panties too."
Steve went into pre-adolescent shock right there and then. Mary was one
of the most popular girls in school. She was a senior, the head-
cheerleader to boot. Steve hadn't ever even had a girlfriend, and now
Mary Ramses was going to humiliate and make Steve's life into a living
hell.
He sleep-walked over to an empty lunch table and sat picking at his food,
unable to do anything other than think about the many ways in which Mary
Ramses could torture him. His life was over, although his penis was rock-
solid thinking that maybe it was just beginning.
He looked over at Mary and her cheerleader friends and was embarrassed to
find that they were all looking over at him and laughing. Mary smiled and
gestured for Steven to come over, but Steven turned away with a shudder
and went back to picking at his meal.
But Mary wasn't so easily deterred. She detached herself from her friends
and strutted over to the sophomore that she ordinarily would never have
even noticed, she being a senior and all. Mary leaned in close so that
Steve was enveloped in the cloud of her perfume, then putting her hand
right on the panty line on Steve's inner thigh, she said, "I like a man
who's in touch with his feminine side." Noticing the bulge growing next
to her hand she added, "it looks like you do too."
Mary stood up and looked down at Steve, who still sat in a stupor. When
she realized that he was unable to respond, unable to even look at her,
she laughed at her power over the poor kid. She took a moment to consider
her next move, and then she pulled a ballpoint pen out of her purse and
scribbled her phone number on his hand. "Call me tonight at seven," she
whispered and then wheeled and walked away.
Steve spent the rest of the hour staring at his hand. Mary Ramses had
given him her phone number! It was simultaneously the very best and the
very worse thing that had ever happened to him! Mary Ramses had noticed
him! Oh, Yes!!! Oh, God No! Did she like him? No, that couldn't be it.
She was only going to humiliate him--after all senior girls only went for
senior boys, and cheerleaders only went for football players.
Still, hope springs eternal. Maybe, just maybe Steven thought, hoped and
prayed, maybe Mary Ramses had really liked Steve! Maybe she didn't care
about his panties! Maybe she thought it was a turn on!
Maybe he was out of his mind and his life as a normal high school kid was
over.
The bell rang and startled Steve out of his conflicting fantasies. He
stood up and trudged off toward class. Mary and several of her
girlfriends sat by the entrance, giggling and pointing as he passed. Just
as Steve got to the door, Mary suddenly called out, "Steven, come here
for a moment."
Slowly Steve turned to face the girls. Five senior cheerleaders. It was
worse than a firing squad. He summoned his courage, cleared his throat
and said "Yes, Mary?" His voice cracked in nervousness, and the girls
burst out into laughter once more.
Mary took pity on the obviously petrified boy and pulled him off to the
side. "Steven, I think I might have made a mistake," she said. Steven
deflated and quickly offered to go wash the numbers from his hand. "No,
silly," she teased. "I gave you my phone number, and I expect you to call
me tonight at seven on the dot. But I'm not sure I like having it on your
hand, out in the open for everyone to see like that."
Steven could understand her sentiments, and immediately stammered that he
would write on a piece of paper and never show it to anybody ever. Or he
would memorize it. Anything she wanted. "No, Steven. I don't want to run
the risk of you forgetting my number." Mary pretended to think for a
moment before a wicked gleam filled her eyes. "I've got it," she smirked
and then her eyes suddenly went ice cold. "Why don't you go to the
bathroom and write my number on your little pee pee. I'm sure it's big
enough by now to get all seven digits on it."
Steven immediately went into a blustery but incoherent affirmation of his
manhood. Mary silenced him with a finger to his lips and looked him
sternly in the eye. "Then it's settled. Go write my phone number on your
penis, pull up your panties, wash your hands and call me tonight at
seven."
"Oh yes," she added almost matter-of-factly, "you'd better not jerk off
or else it might rub off."
More laughter from all the girls and Mary almost seemed to be skipping as
she rejoined her group and left the lunchroom without giving Steven a
backward glance.
Teachers ushered students off to class, but Steven snuck off to the
bathroom. He entered a stall and lowered his pants, making sure that his
sister's panties didn't fall past his knees.
Now Steven had the sex drive of a normal teenager, and he was always
ready to masturbate, but never before had he ever been so rock hard and
horny. His cock throbbed in synch to his heartbeat, which was pounding a
mile a minute. Steven stared down at his shaking cock, the pretty pink
panties he was wearing and at Mary's phone number etched on his hand.
He wondered what color panties Mary wore, and his penis twitched
violently at the thought. He wondered if she liked lacy panties? (twitch)
of pretty silk ones? (twitch, twitch). Even plain cotton panties would
be fine. Maybe one day, especially since Mary knew and liked it when boys
wore panties (twitch), maybe one day Steven could steal a pair of Mary's
panties (twitch, twitch). He wouldn't wash them ever, but wear them
while they still smelled all girly.
Twitch! Twitch! Twitch!
Steven threw his head back in fantasy and moaned as he ejaculated. He
came so powerfully that some of his jizz rebounded off the partition door
and splattered across his upturned face. It was the most amazing orgasm
of his young life, and he hadn't even touched his still-pulsing penis.
Steven sat there panting for quite some time, and when the droplets
dribbled down into his mouth, he swallowed them before he could realize
what he was doing.
The salty goo snapped him out of his post-orgasmic bliss just as it
disappeared down his throat. Steven panicked. "Oh my God," he whispered
to himself, "I just ate cum! That makes me gay!" And at that thought,
Steven suddenly began vomiting.
In between his retching, he heard the door to the bathroom opening and
heavy footsteps stepping up to the stall. There was a pregnant moment
while Steven lay paralyzed with his head still in the toilet. If whoever
was on the other side of the door looked down, he would surely see
Steven's pink panties now pooled around his ankles. Steven tried to keep
very still, but he could hear breathing just outside the stall door. Then
a deafening knock slammed through the bathroom. "Son," a deep voice
asked. "You okay in there?"
Steven found he couldn't answer. He had just turned gay and now this man
knew it. He had seen the panties, and could probably smell the jizz
dripping down the partition. As soon as he opened the door one of two
things would happen. The man would look at Steven and immediately know
that he was gay and either beat him up if the man was straight, or if he
wasn't, then he would shove him up against the wall and rape him. That's
what homos did. Steven was only sixteen, and his inexperienced mind could
only see these two nightmare possibilities.
His world was spinning out of control. Things were getting dark.
Somewhere off in the distance, somebody was knocking, but it sounded like
the sound was coming through water. It was so faint, so far away, and
getting farther, and farther...
Steven woke up in the nurse's office. He was lying on the couch with a
felt blanket spread out over him. He moaned and tried to sit up, but
Nurse Schmidt slowly pushed him back down. "Zere, zere," she said in the
German accent that she hadn't been able to lose since coming to American
ten years ago. "Stay down, mein dear. You had us all vorried. I called
your muzer. She'll be here soon, ya? You just lie zere und rest."
Steven had finally calmed down, and he even fell asleep for a moment
while the nurse wiped the sweat off his face with a warm wash cloth. A
bell woke him, and he could hear the roar of student feet stampeding just
outside the door. The nurse's office was just off the reception area, and
he froze up once again when he heard the door open and the school
secretary call out "Hello, Mary."
"Hi Mrs. Beardall. I heard Steven fainted."
"Really? How do you know Steven?' Mrs. Beardall asked warily.
"We're friends," Mary answered confidently and brushed past the woman and
into the nurse's office. She laughed softly as she saw Steven; wide-eyed
and shaking in terror with the blanket pulled up to his chin. "Oh,
Steven," she mused. "What are we gonna do with you?"
It was at that moment when the tornado that was Steven's mother whirled
into the room. Mary stood aside and let mama claim her baby boy,
smothering him with kisses that were far too embarrassing for a high
school student. After getting a few instructions from the nurse, she drew
Steven to his feet and ushered him out the door. There was a moment as
Steven passed Mary when she smiled at him and mouthed "Call me."
Steve's mom took him home and put his straight to bed. Stevie was her
baby, and after her divorce she found that she had become even more
maternal then ever. Steven was a bit groggy, so his mom started to help
him take off his shirt and pants. Suddenly Steven snapped out of his funk
and twisted like a greased pig. "I'm fine mom, let me go," he cried out
in panic.
Mother's intuition kicked in and she suddenly realized what was going on.
Steven was wearing those damned panties again and didn't want her to know
about it. Well, too late honey. A mother notices these things. She sighed
and closed the door, thinking that very soon she was going to have to sit
him down and have a long, difficult talk with her boy.
Steven lay in bed wearing nothing but the panties, fingering the cum that
had dried on them. He watched the clock and wondered what else could go
wrong today. Soon the whole school would be calling him queer-boy! He
just knew it!
At 6:00pm Steven began to feel woozy again, although his cock was still
rock hard. By 6:15pm his head was aching and so was his cock. At 6:30pm
he had to lie down to keep from passing out in frustration. Finally, he
locked the door to his room and began to trace the outline of his cock
through the sheer pink material that had gotten him into so much trouble.
He hated that these panties turned him on so much, but he was unable to
do anything about it. He reached out and no sooner did he touch himself
than he was wracked with a violent spasm and a single drop of cum started
to ooze through the silky underwear. He stopped just on the brink of his
orgasm, remembering that Mary had told him not to play with himself. So
he steeled himself and obeyed, but was still left with a tantalizing need
to reach a climax soon.
Steven closed his eyes to ward off temptation, but was left with visions
of Mary, stripped down to her bra and panty, and Steven wearing a
matching set. They were fucking each other. It was too much. It was 6:45
and he was in agony. "Fuck it," he told himself and reached for his cock.
But just as he touched himself the phone rang. Steven froze. He somehow
knew that it was Mary. Sure enough, his mother was calling up the stairs,
"Steven! Telephone. Are you feeling well enough to talk?"
"Got it, Mom," Steven screamed and lunged for the phone in his room. He
waited until he heard his mother hang up the downstairs extension, then
he ventured a tentative "Hello."
"Hi Steven," came Mary's full voice through the telephone line and
directly into his head. "I hope you're feeling better, honey, 'cause
we've got some things we'd like to discuss with you."
Steven swallowed and tried to find the remnants of his masculinity. "Oh,
sure Mary," he ventured, "I was just faking that. Wanted to get out of a
History test."
Mary wasn't buying it. The sweetness in her voice disappeared and was
abruptly filled with a deadly seriousness that told Steven that she
wasn't to be trifled with. "Listen, you little sissy punk. Who do you
think you're fooling? You're nothing but a little panty boy, and probably
went right home and jerked off into your pretty panties. That's why I
called, I figured that you'd rubbed my phone number off from beating your
meat so hard. You'll have to be punished for that, but the important
thing, you little punk-ass fuck, is that you realize that if you piss me
off, I can make your life into a living hell. I can have you beaten up. I
can make sure that everybody in school thinks your gay..."
"Please, no, Mary!" Steven cried out from the depths of his heart. "What
do you want? I'll do whatever you say."
Suddenly Mary's voice was all sweetness and light. "That's better honey.
Listen, Steven, we can be best of friends or we can be bitter enemies. If
you want to be our friend, you should come back to the school. We'll be
waiting at the gym. Be there in 20 minutes"
"We'll?" Steven squawked.
Mary ignored him. "And don't forget to wear your pretty panties. And I'd
love it if you could find a bra to go with it."
"But I'm sick. My mom won't let me..."
Mary had already hung up.
What to do? Steven saw disaster on every path. If he showed up wearing
panties and a bra, he'd probably find the football team waiting there to
fuck him. If he didn't show, Mary would probably tell the football team
that he was gay and tell them to track him down and fuck him.
Either way he was fucked.
And then Steven's mom made his choice for him. She knocked softly on the
door and asked "Sweetie, are you going to be okay? I've got to go back
into the office."
Steven recognized fate and mustered up his confidence. "Yeah, Mom.
Everything's fine. Thanks."
His mom sighed and realized that he was probably masturbating again.
That's all he seemed to do these days. She took some small measure of
comfort in the thought that if he was jerking off again after such a
traumatic experience, well that certainly meant that he was going to be
okay.
Steven waited until he heard the car pull out of the driveway and then he
exploded into his sister's room where he found a sexy leopard print bra.
Staci had never been all that big, so the bra cups actually cupped his
flesh nicely. And while he was rummaging through the lingerie drawer, he
spied the matching leopard print bikini. Steven discarded the cum-spotted
pink panties and slipped into the fresh pair. In for a penny, in for a
pound he thought, and shimmied into a pair of his mom's pantyhose. Then
he threw on some jeans and a sweatshirt and ran out the door.
Too bad I didn't have time to do my nails, he thought. I bet Mary would
really like that.
Fifteen minutes later he was standing outside the gym, watching as Mary
and the other cheerleaders went though a late-evening practice. He was
terrified, but unable to stop himself as he slunk into the back shadows.
Mary spied him immediately. She turned practice over to her co-captain
and then bounced over with a few of her friends. They seemed positively
giddy to see him. Melody, who Steven thought was by far the best looking
of all the senior cheerleaders came right up and hugged him. "Oh my God,
Mary. You were so right!" She said. "He'll be darling!"
Steven was enveloped by a whirling mass of femininity in cheerleader
uniforms. They pushed and pulled him forward, and before he knew what was
happening, Steven found himself standing in the high school holy-of-
holys: the girl's locker room.
Mary forced him to his knees as Melody locked the door. They surrounded
him and before he could object, they stripped him down until he was
kneeling in his sexy lingerie, looking up at the five most popular girls
in school.
"Look, Steven," Mary finally began, "You like wearing panties. Pantyhose
too, I see. Which is okay. I never could understand why guys would want
to wear those itchy boxers when they could wear silky, pretty panties
like mine." At that, Mary dropped her skirt. Steven's jaw followed it to
the floor.
Melody added "I usually like to wear lacy thongs, but we have to use
these stupid Lycra bottoms with our cheerleading uniforms." And from
behind him Jancey agreed, "I hate these fucking bottoms. They rub me raw
and leave me itching for a little relief." Steven turned to acknowledge
her comments and was stunned to find that all five girls had completely
removed her cheerleader uniforms. Steven had never seen a vagina before.
Here were five, and they were closing in on him.
Mary pulled him around to face full front. There was something in her
eyes that kept his attention riveted on her, even though he could tell
that the other four cheerleaders were fingering themselves just off in
his periphery vision.
"Here's the deal," Mary said while pulling off her top to expose a
perfect pair of milk-white breasts. "We're the senior cheerleaders. We
could date anybody we wanted to, but we only date the starters on the
football team. Which is fine if you just want to be seen, but those guys
only want one thing..."
"Slam, bam, no thank you ma'am" came the answer from Tiffany behind him.
Melissa laughed and pulled Steve's gaze back to the front. "Well, we need
our fun too. And that's where you come in. You're a nobody in this
school, but we can make you into the most popular boy here."
"But not some jerk who goes running to his friends saying that he fucked
a cheerleader," Tiffany spat.
"Fucking David Billingsly!" Jancey agreed.
"That's where the panties come in," Mary said. "You're going to wear our
panties everyday from now on, so we know that you'll be on your best
behavior. Every morning, we'll give you a new pair to wear during the
day. You can jerk off into them at night, just as long as you hand wash
them at home and give them back to us the next day."
"Wait a minute," Jancy interjected. "How do we know that he's worth it?
I'm not going through all this if he can't bring me off."
Mary was laughing once again. She knelt and looked Steven square in the
eyes, spreading her knees so that the scent of her arousal wafted up to
Steven's nose. "Here's the deal," she said. "We know that you love being
dressed up in frilly lingerie. The hard-on underneath the pantyhose tells
me that you will love what we've got in store for you. We will make your
dreams come true. But you've got to give something back to us. You'll
make love to us with your mouth whenever we want you to. Wherever we
want. We'll keep it all discrete, but basically you'll be our little sex
slave."
"You take care of us, and we'll take care of you," Melody added and
snaked her tongue into Steven's ear.
"Hell, if you do me right, I might even let you fuck me one day" Melissa
said.
"Then again, do me right enough, I might let my boyfriend fuck you," Mary
said and was pleased to see Steven's cock jerk once underneath her hand.
Soon, there was a dark pool spreading across the front of his panties,
and all five girls were clapping and saying "Looks like we have a
winner."
Steven was then put to the test. He was pushed down onto the bench and
Jancey straddled his face and commanded him to "lick." Steven did his
best, and was finally rewarded with a flush of musky juices that he
swallowed down.
"Not bad," Jancey said as Melody pushed her aside and mounted up. Melody
was much more instructional, and Steven found that she was easy to
please. Tiffany quickly followed, but she had been fingering herself as
she watched the preceding action, so she flooded his mouth with her
juices just moments after she straddled his face.
Melissa was a much tougher nut to crack. By this time Steven's untrained
tongue was worn out and protesting its unexpected workout. But Melissa
was relentless, and she rode Steven until he was ready to drop. Finally,
she screamed out in victory and collapsed in an orgasmic heap, her vagina
still covering Steven's now-raw mouth.
That left only Mary, who strutted over to Steven and took his face in her
hands. "How you doing, honey?" she asked. Steven caught his breath and
told her that he was fine, and then the juice-smeared grin plastered
across his face told her that he was actually doing much better than
fine.
"Do you trust me?" Mary asked and Steven nodded "Yes."
Mary smiled and then handed Steven her sweaty uniform. "Put it on," she
commanded.
Steven felt a bit silly, but also ready to burst out in joy. He was all
grins as he noticed that Melissa and Melody, and Tiffany and Jancey had
paired off and were licking each other like some lesbian sideshow.
Melissa came forward with a tube of lipstick. "Close your eyes," she
commanded.
The lipstick felt so sensual. The only thing that felt better was the
feeling of Mary's thickly-painted lips rubbing up against his, and soon
she had forced his head back and was darting her tongue in and out of
Steven's mouth.
And then a deep voice froze Steven in his tracks. "Well, what do we have
here?"
It was the voice from the bathroom, and Steven turned to find the Janitor
standing there leering at the girls. "Six pretty girls. Looks to me like
they're only missing one thing. A big fat cock and two balls that are
overflowing with my love juice." With that, the janitor dropped his pants
and a huge mound of meat sprang upward. It was as big as anything that
Steven had ever seen in any of the porno magazines that he had stolen
from his sister. That cock was certainly many times bigger than the teeny
peenie that Steven had trapped in his panties.
And that massive cock was pointed right at Steven.
Mary put her arm around him and explained. "Steven, meet Mr. Jones. He's
got the best cock in school, but the problem is that he only likes boys."
"What a shame," Melody added from the background.
"So we're going to play a little trick on Mr. Jones."
"Yeah, trick me baby!" Mr. Jones commanded.
Steven started to stammer and protest as Mary pushed him to his knees.
"Don't worry," she said, "You're not ready to take his monster, but I
am."
"Me too," "Me Three," "and me" added the other girls.
Mary continued her instructions. "We've found that if a little sissy boy
will lick his penis, he gets real hard, just the way we like him. And he
can stay hard enough to fuck us all, just as long as the sissy boy keeps
licking his balls while he fucks us."
"What do you say?" Mary asked, and she seemed genuinely ready to accept
his decision.
"Please Steven, I need it so bad." Jancey pleaded and started kissing his
neck.
All the girls crowded around, pleading for his help and planting kisses
all over his body. But Steven knew that if he licked this man's cock then
he would really be gay. From now on and forever. And that was just too
much, especially when he looked at Mr. Jones' cock. How could anybody
ever get that much meat into them? And Oh Shit! Steven suddenly realized
that the monster hanging two inches away from his face wasn't even fully
hard yet.
He lowered his eyes in shame. He just couldn't do it. He would have to
tell the girls "no" and risk the consequences later.
But as he looked down he saw a sexy bra and he could almost imagine tiny,
budding breasts swelling to fill the cups. His belly was flat, and while
there was an obvious bulge in his panties, it didn't detract from the
illusion that he was now a girl. And a girl sucking on a cock wasn't gay.
In fact, a girl sucking on a man's cock was really hot, and it was making
him hot just thinking about it.
He lifted his face to Mary and took the step that would change his life
forever.
"Okay, but I want a girls name first, so you don't think I'm gay" he said
and then sank to his knees and began enthusiastically kissing Mr. Jones'
penis. All five girls clapped in glee, and Steven was quickly renamed
Stephanie.
So Stephanie started to give the first blowjob of her new life She tried
to take the cock into her mouth, but it was far too big. She finally gave
up, gasping in breath and looked up at the janitor to apologize. "Don't
worry about it, Stephanie" he said. "You'll learn how soon enough."
With that he growled and turned to Melody, threw her over the back of a
bench and slammed into her from behind. Stephanie scooted in underneath
them and tried to catch the heavy balls as they slapped up against her
face and Melody's cunt. She never caught them, but she did lick up all
the juice that poured out of Melody when she came.
Jancey was next, and this time Stephanie found herself sucking on
Jancey's and Mr. Jones' nipples. But she only had one mouth and two
hands, so Melissa crept up beside her and soon they were alternating
between Jancey's tits and Mr. Jones' nipples. Jancey moaned out as orgasm
overtook her. Melissa bent down to French kiss Jancey, and Stephanie slid
down to lick up her pussy juices.
Mr. Jones' sticky cock prodded against her face, and Stephanie turned to
give it a good tongue bath as well. This time she swallowed almost half
of it, which got the janitor all worked up again, and he tore away and
threw Mary down and started to violently fuck her. Mary had her orgasm
even before Stephanie could get there to lick it up. She got to her pussy
just as Jones started to cum. He pulled out of her and shot thick streams
of cum all across Mary's abdomen and tits.
Without even being told to do so, Stephanie licked it all up. It wasn't
gay, Steven told himself from somewhere in the back of his mind. Girls
like cum. And I'm going to be the best girl ever!
Mr. Jones was getting hard again just watching Stephanie. "Damn girl," he
said, "I knew when I saw you wearing those pretty panties in the bathroom
that you would be something special, but God damn girl..."
He didn't finish his thought because Stephanie attacked his cock, and as
it was less than full mast, she managed to swallow it all the way to the
base. The girls were in shock. Stephanie had just done what most of them
could not do.
This time it was Mary who bent down and started licking the man's balls.
Stephanie's eyes bulged out when he felt the penis start to expand again,
but she willed herself to relax and found that she was able to deep
throat the cock. The girls gathered 'round and started clapping, saying
"Go Girl!" Stephanie was so proud that she didn't realize until it was
too late that her mouth and throat were being filled-to-overflowing with
cum. She lost her breath and choked, coughing sticky semen up through her
nose.
As she lay trying to regain her composure, all the girls were patting her
on the back and asking if she was okay. All Stephanie could think about
was that she had missed some spunk and that she needed to suck it all
down before it got cold. Stephanie smiled and went back to work as the
girl's cheered her on.
As she licked up the spilled cum, Mary dropped down further. Ripping a
hole in Stephanie's pantyhose and pushing her panties aside, she engulfed
Stephanie's penis to the hilt. Mary had obviously done this before, and
Steven came within seconds.
Without swallowing, Mary came up and started French kissing her new
girlfriend. Stephanie could taste her semen as it coated their tongues.
They groped at each other and made out until Tiffany cautioned that the
practice was over and they had to clean up before the other cheerleaders
came into the locker room. So it was one last cum-drenched kiss and then
all six girls jumped into the shower while Mr. Jones started mopping up
the locker room.
Later that night as Steven lay in his bed unable to sleep, he decided to
call Mary. She had a private line in her room, and had said that it was
okay to call at anytime. She had written the new number on his penis
personally. So at 2:00am, they found themselves talking softly on the
phone.
"Are you wearing the nightgown I gave you?" Mary asked.
"Plus your sticky panties and my sister's bra" Steven answered.
"What about the dildo?"
"I had it in for almost a half hour, but then it hurt too much and I had
to take it out," he replied with shame in his voice.
"That's okay sweetie. You keep practicing on it until you can go all
night with that baby lodged in your sissy pussy. Take as much time as you
need," she said.
"I can't take too long," he replied, "I don't think that Mr. Jones will
wait much longer for my ass to get stretched out."
They both giggled like naughty little schoolgirls.
"Well, I guess we'll find out in Friday," Mary finally said.
"Why? What's happening on Friday?"
"Oh, my parents are out of town so I'm having a slumber party. Just us
six girls. But this time we're going to dress you up all the way with a
wig and makeup and fingernails--the whole thing. You meet us at the mall
at five so we can get your ears pierced. And don't forget, you've got to
shave your legs before Friday."
Stephanie giggled guiltily "I already did. The hairy legs just felt so
icky against the nightgown"
"Good girl," Mary said. "Just for that, I give you permission to jerk
off, but only if you fuck yourself with the dildo while you're doing it."
Stephanie had started masturbating and fucking herself even before Mary
finished the sentence.
Oh, and Stephanie, just once and then right to bed young lady. You're
going to need your strength for Friday."
"Why? What else is happening on Friday," Stephanie asked in between gasps
of pleasure.
"After we get you all dolled up, we've invited the football team over to
meet the new cheerleader."
In the days that followed the birth of Stephanie at the hands of the five
senior cheerleaders (and one well-endowed janitor), Steven's life was
radically changed. He had started out as just another one of the unknown
sophomores at his high school. Within two weeks he was the cool new kid
who hung out with all the cheerleaders. All the boys in school were
jealous of this relationship, and all the girls wanted to know just what
made Steven so appealing to that select handful of the most popular girls
in school.
Just what was his secret?
If they only knew.
Steven was quickly getting used to his role as the senior cheerleader's
panty boy. He would arrive at school early and find a soiled pair of
panties hanging in his locker. At first, he didn't know for sure which of
the cheerleaders had donated today's pair, but after spending a few weeks
crouched in between their legs as Stephanie, Steven was quickly getting
to the point where he could identify each girl by the smell of her
panties.
Steven would immediately go to the restroom and put on the panties.
Sometimes there would be other "toys" to go along with the feminine
finery. Butt plugs were quite common, and they were getting larger and
larger as each day passed. There had also been cock-and-ball sheaths and
once there was a simple bicycle padlock with a note attached saying "Lock
me around those girly-balls of yours."
Once Steven was locked in tight, the cheerleaders left the padlock in
place for one week straight. It didn't get in the way of his penis, but
the hard-steel weight of the padlock as it rested in his panties was a
constant reminder that even though he was Steven on the outside, he was
really Stephanie on the inside.
Every day Steven was given a schedule to follow. Mostly he would go to
his classes as usual, squirming to concentrate on his studies while a
butt plug stretched him out or a clamps bit into his nipples. After
school he would report to the gymnasium, where he had volunteered to be
the school mascot. This meant that Steven no longer had to take gym, as
he got a P.E. credit by becoming an official member of the cheer squad.
That was important, because Steven's entire body below his neck was now
completely hairless and his toenails were kept painted a deep red--"Slut
Red," Melody had laughed. "Stephanie-Slut Red," Mary had corrected.
Previously, Steven had gym for his first period, so he was now able to
transfer into a different class. Mary snickered and suggested that he
take up art. Now Steven had never thought of himself as the artistic
type, but he filled out the paperwork at Mary's insistence. "Trust me,"
she said, "You're going to love Mr. Mason."
The next day Steven transferred into basic art, and was immediately bored
by the whole class. Mr. Mason sat him at the back of the room where he
found himself daydreaming, anticipating the lunch hour when he would get
together with the other cheerleaders. Steven wasn't allowed to eat much,
as the girls were helping him develop a more respectable figure.
Actually, he never got to eat lunch, but he usually got dessert when they
would steal away to a special janitorial closet that Mr. Jones let them
use for their lunchtime quickie sessions.
Sometimes Mr. Jones would be there waiting for them and Stephanie would
get an extra filling meal. Mr. Jones was hung like a horse, and it had
taken a while before Stephanie had learned to accommodate him in her boy-
pussy. The first time that Mr. Jones fucked him, Mary and Melissa had to
hold his hand and help him to keep from crying out in sheer agony.
Afterwards Steven felt as if he had been ripped in two, and when he
reported to cheerleader practice after school, Mary had found blood in
his panties. She had immediately taken him home where she gently rubbed
oil into his ravaged backside. She held him in her arms and consoled him.
"You'll be fine. All of us take some time getting used to Mr. Jones, and
you're doing better than most."
She kissed him, being sure to grind her lipstick firmly around his lips.
"And besides," she grinned, "once you get used to him, nobody else will
do." Steven laughed weakly at the thought.
Now that a week had passed, Steven had to agree with Mary's assessment.
He had spent the night dreaming wildly about Mr. Jones and "the Bull," as
the girls had christened his cock. In his dreams, the bull had found a
twin, and so they were free to stuff Stephanie from both ends. It was
such bliss dreaming about it that Steven woke with cum spattered all over
the inside of his nightgown.
The dream had returned night after night, and the cheerleaders decided
that Stephanie was having too much fun at night. But even when she was
tied down one afternoon and locked into a metal chastity device, she
still managed to stain her panties every few nights. Finally Melody gave
in and admitted defeat. "That little slut is just too horny," she
laughed. "No Wonder she shows up every morning ready to ride the Bull!"
Such was the case this morning. Steven woke up and immediately started to
think about sex. Mary had pulled him aside before classes started and had
him give her a quick licking, but there wasn't enough time to give
Stephanie any real pleasure. There wasn't even a butt plug this morning,
and so his ass twitched as it yearned to be filled.
And now he sat in a boring art class, daydreaming about the Bull and
knowing that it would be hours before Stephanie would have her chance to
get gored. It was frustrating, and Steven thought of a fun little
scenario. He would stand up and scream out, "I want to be a girl full-
time. Won't somebody please get over here and fuck me!" And just like
that, some fifty high school boys would descend on Stephanie and each of
them would be hung like Mr. Jones and spurt gallons of semen with each
thrust.
It was a delicious fantasy, but unfortunately Steven would have to wait
until lunch to get any real relief.
The class was working with clay, and Steven decided to pass the time by
making a "totem pole," one that was the exact same size and width of Mr.
Jones' real life tribute to male virility. He found himself getting
excited as he ran his hands up and down the pole, wishing once again that
the girls had given him a plug to use today. He felt so empty inside.
Class had only been going for fifteen minutes, and Steven came to the
realization that he wouldn't be able to make it through the whole period
without getting some relief. He raised his hand and asked to be allowed
to use the restroom. Mr. Mason didn't seem to care, and Steven was soon
running through the halls in search of the maintenance office.
He burst in and found Mr. Jones working on something electrical. He was
surprised when Steven burst through the door, as this was his private
area and students weren't allowed entrance. But he smiled when he saw
that it was Steven. The bull liked Steven better than Stephanie, and
always knew that it was a hot young boy hiding underneath those frilly
panties that he wore.
Still, rules were rules, and so the janitor started to warn the student
about having to be discrete during the day. The boy just growled at him
with a hunger-laden voice. "Shut up and fuck me!" he said and was out of
his pants even before he had locked the door. "I've only got a few
minutes, so do me hard and fast."
Jones barely had time to get up from his stool before ten teenaged
fingers were ripping his pants open. He gasped at the heat that burned
his cock as Steven swallowed it whole in one quick swoop. Tiny muscles in
the boy's throat came alive and quickly coaxed the bull into coming out
to play.
Now it was the bull's turn to give off heat, as blood rushed in and
engorged the organ. As per the little vixen's request, the Janitor picked
the boy up as if he were a rag doll and slammed him down across the
stool. Steven was already holding his ass cheeks apart, so with nothing
more than a well-aimed dollop of spit, the bull charged in and was
greeted by the Steven's hot little love tunnel.
God, this kid was hot. A few weeks ago he was some nobody-sophomore. Now
he was the best fuck that Jones had ever had, and that included some
transvestite hookers who made their living by being a hot piece of ass.
Steven, or Stephanie, or whatever the cheer-sluts were calling him this
week, this kid was amazing because he oozed raw, feral sexuality. He was
a natural-born cocksucker, and his ass was so tight.
The Bull roared and Steven mewed in pleasure as he was filled up with the
janitor's semen.
"Now," Jones panted, "go clean yourself up and then get back to class."
"If you don't mind," the little minx replied, "I'm going to leave it all
inside me so I can feel it dripping down my legs all morning long." Then
Steven pulled up his panties, blew the janitor a kiss and practically
skipped out the door.
Art class was much easier to take now that Stephanie's sexual hunger had
been sated. Steven even got into the spirit of the class and started to
mold a figure of a cheerleader. He gave the statue a tiny waist, huge
breasts, and plump ass and hair that went half way down her back. The
details weren't very good, but Steven wished that whatever gods were out
there would turn this day into an episode of "The Twilight Zone" and
suddenly turn him into the girl he had sculpted.
Stephanie was getting worked up again, and by the time the bell rang, she
was wondering if there might not be time for a quick visit back to the
janitor's office. Steven smiled as he relived this morning's quickie. As
if on cue, his ass twitched at the memory and Steven felt a dribble of
semen dripping down his leg.
The memories were a pleasant distraction, and so Steven took a little
while to gather his things and was the last one out of the class. But
just as he was at the door, Mr. Mason suddenly reached out and clamped an
iron grip on his shoulder. "Steven, I think we need to have a little talk
before you go." Steven was abruptly pulled out of his memories, but
before he could reply, Mr. Mason threw him roughly to the ground. "My
supply room! Now!" he growled in a soft voice that was much scarier than
it would have been if he had been yelling.
Steven scrambled in fear to his feet, but Mr. Mason kicked him back down
to his knees as he turned and locked the door. "Crawl!" he barked, and
Steven was too frightened to argue.
No sooner was he inside the art supply room than Mason lifted him with
surprising strength and threw him across a workbench. Steven trembled in
fear for his life as the teacher crushed his face against the bench and
whispered in his ear in a voice that dripped with malice. "Do you think I
don't know what you're up to?" he hissed. "Sitting in the back, making
that 'totem pole' and then rubbing it like you were a common whore!"
Steven started to protest, but Mason ground his face into the bench.
"Don't you dare deny it! I can smell the sex on you." It was at that
point when Mason noticed that the wet puddle of semen had soaked through
the back of Steven's pants. "What the fuck is this?" Mason dipped his
finger in the moisture and brought it to his nose and sniffed.
"Why you little whore," he growled. "I've got just the punishment for a
slut like you."
Mr. Mason quickly produced four handcuffs and had Steven's wrists and
ankles locked to the four corners of the workbench within moments. He was
bound up expertly, and by the time that Steven thought to struggle, it
was already too late. Steven considered screaming for help, but it was if
Mr. Mason could read his mind. He produced an inflatable penis gag and
shoved it down Steven's throat and buckled it in place.
"Is the little slut scared?" asked when he saw tears start to form in
Steven's eyes. Steven nodded, hoping to gain some sympathy, but Mason
just smiled and said "Good. You should be." Then he pumped the gag up
until it felt like Steven's mouth would burst.
Mr. Mason pulled a box cutter out of a drawer and brandished it before
Steven's terror-filled eyes. Steven thought that he was about to be
killed, and was almost relieved when the teacher simply sliced his
clothing off of him, leaving him only his flimsy panties for modesty.
Mason did however, cut a large hole in the panties where his finger
immediately snaked through and into Steven's cum-slick ass.
"So you like getting fucked in the ass, do you?" Mason asked as he
laughed to himself. "Well I'm sure that we can give you what you want
before the day is through." Then Mason strode out of the room and locked
the door behind him.
All through the next class period Steven struggled to get free, but it
was no use. The handcuffs bit into his wrists and ankles, and the awkward
position in which he was tied to the workbench had given him a muscle
cramp. Still he struggled loudly until finally he heard the door being
unlocked. Mason sauntered in and turned on the kiln and a fan that was
loud enough to drown out all of Steven's noise. Then he pulled out a
leather wrapped crop and slashed it loudly through the air. "This is what
happens to bad girls who make too much noise when they should be quiet,"
he said and then immediately commenced beating Steven's unprotected
backside with the crop.
It took only a moment before Steven's back, bottom and thighs were criss-
crossed with angry red welts. Mason leaned in close and whispered
directly into Steven's ear, "Now be quiet, or I'll really give you
something to cry about." And then he was gone again, locking the door and
leaving Steven alone in the room with a kiln that was quickly making the
temperature unbearable.
By the time second period ended, Steven had fallen asleep due to physical
exhaustion and the now sweltering heat. He awoke to feel cool hands
rubbing some sort of ointment into the welts that burned on his ass.
Another set of hands worked the ointment into his thighs, and then Jancey
snuck into view and gave him a tender kiss on the cheek. "Mason's a bit
rough," she whispered, "but I think you'll have fun before the day is
over."
Just then Mason came into the room. "So, I see you bitches have a new
slutty friend," he said. "Well then, let's show her just what happens to
sluts in my classroom."
On cue, Jancey and Tiffany stepped forward and began undressing the
teacher. They began licking and sucking on his nipples while Melody knelt
in front of Mr. Mason. She lowered his pants and began sucking on his
cock. As soon as he was hard he shoved the three girls away. He came
around behind Steven and rammed his erection without fanfare into
Steven's still-slick asshole. He wasn't very big, but Steven still winced
with every thrust because of the crop marks that lined his ass.
"Come here, slut," Mason spat in the general direction of Melody, "suck
my balls while I fuck this whore." Melody quickly complied with the
teacher's directive, frantically trying to capture his testicles as they
continually slapped against Steven's backside. For his part, Mason was
like an animal, pistoning rapidly into Steven who was still stretched out
and gagged and unable to do anything other than allow Mason to fuck him
like a piece of meat. Steven was still terrified by what was going on,
but he was unable to deny that the feral nature of this fucking had him
turned on even more than he had been this morning in Mr. Jones' office.
Suddenly Jancey stepped into view holding the crop. "Oh, Mr. Mason," she
taunted," look what I found." She stepped out of view and all three girls
started laughing. And then Mason cried out as Jancey began whipping him
viciously. If anything, he began fucking Steven harder as Jancey beat him
without mercy. Tiffany found a paddle and started spanking Mason's behind
while Jancey concentrated on his inner thighs. But it wasn't until Melody
finally captured Mason's balls in her mouth and started to bite down and
growl that Mason went crazy.
The teacher screamed out in a mixture of pain and ecstasy and flooded
Steven's bowels with so much semen that it squirted out as he continued
to pump into him. Finally he collapsed, spent and gasping for breath
while his cock deflated in Steven's ass and the cheerleaders continued to
whip him with the crop and the paddle.
And then it was over. Mason collected his clothing and left without
saying a word. Jancey, Tiffany and Melody also left, but they didn't
release Steven from his bondage. When he muffled something into his gag,
Jancey turned around and told him, "Don't worry Stephanie. You've got all
day to have fun with Mr. Mason. We'll come and get you after school."
And so Steven spent the day strapped down against the workbench in the
prep space just off of the art classroom. After third period Melissa
stopped by and unlocked Steven. She gave him a drink of water and let him
work the cramps out of his arms and legs, but then she dragged him down
across the workbench and locked him up even tighter than before.
Just before lunch, Mr. Mason stopped by and fucked Steven once again. He
didn't say a word, but as he left he taped Steven's eyes closed. Moments
later, Steven felt the presence of several people in the room. He only
heard one boy's voice say "cool!" but he quickly felt three new cocks
ravaging his backside. Mason undid the penis gag and allowed Steven to
suck his cock while he was being fucked by the three mystery guests.
Steven realized that Mason would like it if he bit down a bit as he
sucked his cock, and by doing so, was rewarded with a weak trickle of cum
dribbling into his mouth.
After all four had spurted into Steven, he was unbound and manhandled
into the corner. Steven's muscles screamed at their sudden use, and so he
was in no condition to fight as he was quickly mummified with several
rolls of duct tape. From neck to toe, he was immobilized, with only his
ass, genitals and face remaining free from the tightly wrapped tape.
He was wrapped so tightly that Steven couldn't bend a single joint at
all. So a rope was tied off around his balls and Steven was propped up in
a corner, held erect only by his testicles.
Sometime later, Mary stopped by to see how Steven was doing. She didn't
say a word, but Steven could identify her by her smell, and was comforted
by her presence. Mary unbuckled his gag and gave him a drink of water.
Steven tried to speak, but Mary silenced him with a deep kiss and then
put the gag back on him. As she left him she said, "Have fun. I'll see
you after school."
Mr. Mason returned moments later. He pulled the tape off of Steven's eyes
so that he could see that there were four other men in the room with him.
"Gentlemen," Mason began as if he were addressing a distinguished
gathering of intellectuals. "I came across this boy-slut earlier today.
She already had a load of cum deposited in her ass-pussy by the time I
found her, and I added a few spurts myself. Now the question is, what
shall we do with her to show her the error of her ways."
The first man stepped forward and kissed Steven on the cheek. "My dear,"
he said, "I think the chair would do you some good." One by one, the
three other men came up and repeated the same sentence. "So the chair it
is," Mason smiled and pulled Steven toward him by the rope wrapped around
his balls.
The tape was quickly ripped off of Steven's body, taking a good deal of
skin with it. The four men took turns holding Steven tightly while they
fucked him, one-by-one, until Steven could no longer feel them as they
thrust into his ass. No sooner had one man spurt his semen than he came
around to Steven's front and forced Steven to lick his cock clean while
the next man mounted him from behind.
When all four had cum, Steven was dragged into a back closet. Inside
there was a wooden framed chair with a large pole jutting out of the
seat. Steven had been fucked so much that morning and was so stretched
out that it was no problem at all to lower him down onto the pole.
Leather buckles were quickly secured around his arms, legs, chest and
head, and then he was ungagged only long enough for a long rubber phallus
to be slid into his mouth. It bent Steven's head up at an awkward angle,
which allowed the fake cock a straight shot into his mouth and down his
throat.
Two clamps were attached to Steven's nipples and pulled taught, and then
a leather strap was wrapped around his testicles. It too was pulled
tightly away from his body.
Steven sat there unable to move a muscle. He had a pole rammed up his ass
and a dildo crammed down his throat. His nipples and testicles were being
pulled cruely away from his body, and still he managed to sport an
erection.
Mr. Mason noticed that the little sissy was erect. "Well slut," he said,
"Let's see if you're still as excited after a couple of hours in the
chair." And then he attached a pair of headphones to Steven's ears and
closed the door to the closet.
No sooner had the door locked closed than the chair sprung to life. The
pole stuck up into Steven's ass began to pump up and down, expanding in
girth as it went. The same held true for the dildo that assaulted
Steven's mouth. The only difference was that every fifteen minutes or so
the dildo spurted a concoction that tasted remarkable like a man's cum,
and it ejaculated so much of the substance that it overflowed Steven's
mouth and ran down his chin and splashed on his chest.
But the worst pain of all was located in his nipples and balls. They were
pulled so tightly away from his body that Steven feared that the chair
might do permanent damage to his more delicate areas.
Steven could barely hear the school bell ring and he was aware of the
general sound of students leaving for the day. It seemed like an eternity
passed while he sat impaled on the chair, wondering if he had been
forgotten.
Then he began to hear hushed voices approaching. There were two men
coming. One was scared, the other was pretty angry.
The door flew open and the angry voice cried out, "Motherfucker, Mason, I
warned you to knock this shit off."
It was Mr. Jones, and he towered over Mason in rage. "Get ready,
mother," he spat, I'll deal with you next.
Mr. Jones carefully untied Steven and helped him out of the chair. He had
a flask in his back pocket and gave Steven a small sip while he gathered
his strength.
By this time Mason was naked, and shaking as he wondered about his fate.
Mt Jones wasted no time in picking the teacher up and slamming him down
onto the chair. He tightened all the straps down tight and started the
fucking machine portion of the contraption into motion.
A wicked gleam came into his eyes. Mr. Jones left, but came back a few
moments later with his lunchbox. He opened it and handed Steven a warm
Coke. Then he took out a bottle of hot sauce and began rubbing it into
Mason's cock.
The pain must have been overpowering as tears poured out of Mason's eyes.
The smell was overwhelming in the confined space, especially when Mason
shot his load so hard that it nearly hit the ceiling.
Then Mr. Jones went to one of the lab sinks and yanked hard on one of the
pipes. It sprang a leak and started to flood the backroom.
"Well fuck," the Janitor growled, "looks like I'm gonna have to close
this room down for a few days while I fix the plumbing. I should be able
to get students back in here by Friday, but don't expect me to release
you before Monday."
Mason moaned as he knew that he would be spending that whole time being
punished for his assault on Steven. For his part, Mr. Jones just stood
menacing over the art teacher, trying to think of the best way to make
him pay.
That was when he felt a soft pair of hands wrapped around his legs and
slowly squeezing up toward his cock. Jones looked down and saw the naked
boy looking up at him. "My hero," he said as he unzipped the janitor's
pants.
Steven was still too sore to move much, but he needed to give his rescuer
a reward. Mr. Jones was leaning back against the wall while Steven
devoured his cock when the cheerleaders made their way into the room.
"So what's going on here," Mary asked as the girls entered. They all
quieted down as they surveyed the scene. No one said anything for a few
moments while Steven finished giving his reward. Then the girls helped
him to his feet, and finding a blanket in a closet, helped the naked boy
into the gym locker.
Steven sat under the hot shower spray and cried. Mary and the girls had
stripped down and held him. Pretty soon they were all crying.
Steven cried from the physical pain, but he also cried because he was
scared that he liked it so much. He cried that he was just a dumb kid,
and while the girls were his friends, he cried because he knew now that
he would never fully be one of their gang.
Mr. Jones found some clothes and helped Steven get dressed. Then he drove
everybody back to Mary's house. The girls helped Steven into a nightgown
and put her to sleep in Mary's bed. They called the football players and
explained that the party would have to wait. When some of the players
started to complain, Mary shut it down quickly with an icy tone that left
little doubt that they would respect her command or else they would never
see any action from any girl in school, ever again.
Mary called Steven's mother and said that they were having a cheerleading
party, and the needed their mascot to help with some stuff. "Not to
worry," she lied, "Stevie can crash in my brother's old room."
Mom didn't really buy it, so Mary eventually gave in and told her what
was going on. Naturally she freaked out and drove right over, but calmed
down when she saw her little angel sleeping so peacefully in her pink
nightie. She started to cry. Then the girls all started to cry. They
cried until late in the night.
And so it was that all five girls spent the night sleeping in a huddle
around Steven while his mom crashed in the room next door. She slept
soundly knowing that the cheerleaders would protect her baby.
After some much needed sleep and a good breakfast in bed, the girls all
made their way down to the living room. Mom and Mr. Jones were waiting
for them as the filed down the stairs. He stood and offered Steven a
bunch of flowers as he asked, "how ya doing, honey?"
Steven smiled a little and crawled into Mr. Jones' lap while the group
discussed Mason's fate. They could get him fired. They could blackmail
him for the rest of his life. Jones even knew a few "serious brothers"
who could make him disappear forever.
They talked all morning and eventually came up with a plan. Sometime
after midday they made their way to the classroom back prep space. Mason
was still there, strapped to the chair and moaning. There were two men
who had spent the entire night rubbing him down with hot sauce, and his
cock looked like it might never recover from the torture.
Steven stood in front of Mason and slapped him until he had his
attention.
He removed the gag and Mason started to cry and beg for forgiveness, but
Steven slapped him again and again until he quieted down.
"Okay, here's the deal," Steven spat out with a new-found authority.
"We've spent this entire time thinking about how to punish you, but I
have a better plan. You're gonna help me instead."
Mason gawked up, not understanding.
"I like being a girl." He looked over at his mother, saying "I want to be
Stephanie for real. But there's no way I can afford that, but you can."
And so the deal was struck. Mason agreed to confess to everything on a
video camera, which mom would then keep locked up tight in a safety
deposit box. He would quit his job and move out of the city, promising to
never teach again.
Every month he would get a bill for Stephanie's medical bills. She would
start getting the best hormone treatments and plastic surgeries until she
could pass as the perfect high school girl. When it came time for the
final sex change operation, Mason would pay to send the whole group for a
month long vacation to Thailand to help Stephanie recover fully.
The final punishment was a solid steel chastity belt which Mr. Jones
glued around Mason's cock and balls when he finally released him from the
chair. Mason was so numb that he didn't even feel the device being locked
into place.
One year later, Stephanie and her friends all came home from Thailand
just as college was about to start. The school district had heard some
rumors of Mason's activities, and fearing a lawsuit, they allowed Steven,
now Stephanie full time, to finish her studies up at home.
The girls all went to the same school--bonded by their love for Stephanie.
As frequently happens, the girls drifted apart a bit as they eventually
pursued their own interests and boyfriends. But they were all there five
years later on Stephanie's big day.
She looked drop-deal gorgeous in her wedding dress. It was top of the
line, but money was of no concern, as Mason was paying for the whole
thing.
Mother beamed as she watched her daughter walk down the aisle. She was so
happy that her baby boy had grown up to be such a strong young woman, and
knew that was because she was surrounded by her loving posse of friends.
Tears welled up when she heard Stephanie say "I do," before leaning in to
kiss the handsome janitor. Well former janitor, as he had used some of
Mason's seed money to start his own janitorial business. Stephanie was
already working for him while she finished her degree.
Well, maybe not actually working, she thought as she imagined how her
daughter might be spending her afternoons with her husband behind closed
doors.