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Review This Story || Author: Dr. Wu

Toying With Tiffany

Chapter 9 The one with tongues planted firmly in cheeks



Tiffany practically had to be carried from the SUV into the school cafeteria. Her
leg muscles had gotten sore from striding around the mall in the highest high
heels she had ever worn. Then she had endured the half-hour drive back from the
mall with her long legs obscenely spread into the widest possible splits, each
ankle trapped in a back seat window on either side. Her legs were killing her,
and she was having trouble walking.

In addition, she was still intensely focused on having an orgasm, and her four
tormentors were just as determined that she not have one just yet. Every time
they relaxed their vigilance, the 16-year-old cheerleader would steal a hand down
between the damp blonde public curls of her pussy and begin pushing her clit as
if it were an elevator button and she was impatiently waiting. The horrible
images from the stories that Mr. White had told her continued to spin in her
young, impressionable mind, making her hotter than she had ever been, and ashamed
at how they had affected her. She had to cum, dammit! the horny and confused girl
thought. She just had to. Maybe cumming would release the grip the stories had on
her, she rationalized with the part of her brain that was still capable of some
level of thought.

So it was for the best that John Brown and Tom Green each slipped one of
Tiffany's arms around their shoulder and half-walked, half-carried the glazed,
trembling girl into the deserted cafeteria, which Old Joe the janitor had gone
ahead and unlocked. They laid her down on a long table in the center of the room,
its fake-wood laminate cold against her bare skin.

"Pleeeze," she murmured, although she wasn't even sure any more what she was
asking them to do? Let her go? Let her cum? Some of both? She just knew that
right now she was in hell.

"How's that little pussy, Princess?" asked Principal White. "Does the little
Princess want to cum?"

Tiffany felt something wet trickle down out of her virgin opening and start
moving down her thigh. Oh God, was she starting her period? She was mortified,
but she had to find out. She reached down one index finger and wiped at the
sticky goo and looked at it. It was clear, so it wasn't her period. She was so
sexually over-stimulated that her pussy was actually leaking lubrication onto her
body, and running down onto the lunch table!

"Yes, sir, I want to cum," she answered. God, the shame, she thought. Nearly
nude, in her own school lunch room, begging this man for an orgasm.

"Well, as I told you, we're going to help you, Princess Tiffany. It's going to
feel so good. But we're going to trade orgasms. You make us cum, we'll make you
cum. And since we've promised you that we'll let you stay a virgin, we're going
to cum in your ass. That's right, Princess. It's time for a gang bang in Tiffany
Daniels' virgin asshole!" He was practically shouting in jubilation, power and

"Oh nooo!" Tiffany cried and started to get up from the table. Instantly powerful
male hands pushed her back down on her back. She struggled to get up, but Old Joe
was pinning her shoulders to the table while Mr. Brown slipped off the Spandex
miniskirt. Joe grabbed her halter, which was barely tied in place, and yanked
upward, pulling it off. The sweet teen was stark naked, pinned like a beautiful
to the lunchroom table.

"Don't, oh please don't do this!" she wailed in panic as Brown pulled on her
knees, moving them up to her chest. While he held them there, Mr. Green grabbed
her flailing arms by the wrists and pulled her wrists around her bunched-up legs
until her hands were underneath her legs. He quickly snapped the handcuffs that
had imprisoned Tiffany before onto her wrists.

Breathing heavily from the exertion, the men stood back to examine their beautilf
captive. She lay on her back on the table, her knees pulled up to her chest. Her
arms circled down below the backs of her knees, where they were locked in place
by the cuffs. She could not move her arms now, nor could she lower her knees. The
most important part of the arrangement, as Tiffany was about to find out, was
that it left her sweet little bunghole poking out between her gorgeous round ass
cheeks. The little rosebud was completely exposed and defenseless as it winked
nervously near the edge of the table.

Tiffany was moaning and shaking her head from side to side as the men rubbed
their erections inside their pants. They'd been playing with her all night,
exposing her in public, forcing her to give blow jobs to strangers at the mall,
teasing her sexually, bringing her to a fever pitch, then abandoning her sexual
needs the moment before her climax. All four men, although well into middle age,
were as rampant as teenaged boys.

"Shut up!" barked White at the moaning, squirming girl. "Listen to my voice!" he
commanded. Tiffany forced herself to be quiet.

"First of all, no one can hear you, Princess, which is why we haven't gagged you.
But you need to be quiet to listen to me. I want you to think very hard about the
stories I just told you, about what happened to Claire and Tara when they didn't
cooperate. I want you to know that we aren't fucking around here, and if you piss
us off you've got a visit to Dr. Wu coming, maybe even tonight. And you do NOT
want to go there, girl. Now take a couple of deep breaths, because this isn't
going to be nearly as bad as you think. Mr. Brown, would you like to do first

Tiffany stiffened her body, thinking that she was about to feel her teacher's
cock probing at the opening of her ass, trying to penetrate that too-tight hole.
But she didn't. Instead she felt something wonderful - smooth and warm and wet.
For a few second she resisted, but it just felt so good, and soon she began to
relax. As she let down her guard, her sphincter unclenched, and the warm, wet
object began to make little forays up inside her. It would push in a little, then
withdraw, and make lazy circles all over her asshole. It was beginning to feel
very good indeed.

Suddenly the girl realized what was happening at her backdoor. Her math teacher
was licking her asshole with his tongue!

"It's called analingus, Princess," Mr. White explained. "Also known as a rimjob.
It's a little more sophisticated sexual technique than you and your
clumsy-fingered boyfriends as probably used to, or have even dreamt of. The anus
is as full of nerve endings as the vagina, and properly stimulated it's one of
the most intense erogenous zones on the body. Plus saliva makes a wonderful
lubricant, as you relax, soon you'll be able to take in something a little harder
than a tongue."

Even though she knew what was coming eventually, Tiffany put it out of her mind
and concentrated on the good feelings. Her horniness had returned, and now it was
even stronger because of what her math teacher was doing. It was so wicked, but
so wonderful at the same time! While Brown licked, Tom Green the English teacher
reached between Tiffany's legs and placed his first two fingers on either side of
her clitoris and began massaging it gently. The feelings on her clit and the
feelings in her ass began to merge and mingle. She'd never realized how close the
two were, never thought of her own ass as anything erotic.

"How's that feel, Princess?" asked White.

"Mmmmmmm," was all Tiffany could reply. Her defenses were coming down, as her
math teacher continued to tongue her asshole. As she relaxed, he was able to push
his tongue further and further up inside her warm, moist rectum. Green,
meanwhile, continued to work over her hot, throbbing clit, careful not to tip the
horny youngster over the brink into an orgasm just yet.

Tiffany Daniels had forgotten that she was stark naked, that she was laying on a
table in her own high school cafeteria, that she was handcuffed. The sensations
on her clit and in her little bunghole were indescribable, better than anything
she had ever felt.

"How's that taste, John?" asked the principal.

"Tasty as can be," said Brown, taking a break draw a breath. "Her pussy's runnin'
like nobody's business, and the juice is like pure nectar."

"OK, Princess," said White. "Remember we were talking about a trade? Well, fair's
fair. You're getting a hot tongue stuffed up your ass, and now it's time to
reciprocate." Tiffany felt the table shift and opened her eyes, and realized that
her principal, Roger White, was now naked and climbing up onto the table. He
knelt so that one knee was on either side of her head, as he faced her feet. His
ass hovered above her face, and slowly he started to lower it.

"Come on, Princess. You can feel how good that tongue is working on your ass.
Turnabout's fair play. I want to feel your tongue up my ass." And he lowered his
bulky frame so that his big hairy ass hovered just an inch above the
cheerleader's mouth.

Tiffany drifted in a dream state of confusion and horniness. She knew what her
principal was asking her to do was grosser than gross, something that even a few
days ago would have made her run screaming from the room. But she also knew that
she had no choice, she had been reduced to a sex slave, she had to do it. She
stuck out her tongue as the principal lowered his buttocks the last inch and
settled his own ass crack right onto the beauty's mouth.

Her first thought was that it wasn't as bad as she thought. It tasted weird, like
apple cider or something, but it wasn't all that nasty, really, if she didn't
think about what she was really doing. She moved her tongue a little.

"Oh, yeah, Princess, that's right, use that tongue. Lick that ass," ordered
White. Tiffany complied, licking back and forth along White's ass crack. His
erection bobbed in the air out in front of him, and he bent slightly at the waist
so that he could rub the head of his cock, which was swollen with blood and
oozing pre-cum, over the girl's large, erect nipples. The sensation of having her
nipples stimulated added to the delicious massaging on her clit and the
incredible oral reaming of her asshole, and Tiffany felt herself getting closer
and closer to orgasm.

Tiffany moaned into her principal's asshole and continued to work her tongue. It
was all so nasty, so humiliating, and yet so wonderful. Her whole body was on
fire. Maybe soon, she thought, they'd let her cum.

She felt Brown's mouth leave her ass, and then something different. Something
much harder. She knew it must be the head of his cock pushing against her rectum,
knew she was about to be violated. But she also knew she had no choice. She
couldn't see a thing except her principal's ass, so she just concentrated on the
feeling of her clit getting rubbed.

Brown pushed slowly, gently, and eased his cock up into the cheerleader's ass. It
was so tight. So hot. So moist. But his analingus and the girl's own secretions
had gotten her plenty wet, and she was relaxed from the erotic attentions, and
didn't seem to be in any pain. Brown pushed forward, inch by inch, letting his
cock luxuriate in the feeling of Tiffany's rectum.

Finally, he was all the way in. His coarse pubic hair tickled her labia. Tiffany
Daniels, once the most stuck-up cock tease in school, was getting fucked up the
ass by her math teacher. Brown pulled out slowly, then pushed in again. As he
stroked, her ass relaxed and opened up even more. Soon he had a slow but steady
rhythm going, in and out, in and out, pumping his cock up inside her shitter.

White climbed off the table and Old Joe Black the janitor took his place. With
her eyes closed, Tiffany was only vaguely aware of the movement. But she realized
that a different male asshole was now plastered over her mouth, one that smelled
and tasted different - a little stronger, but still not bad. She didn't even
think about what was happening, she just plunged her tongue upward and began to
give a teenaged rimjob to the school janitor.

Brown plunged his cock into the girl over and over. Like all of the men, he was
so horny and the girl was so tight that he wasn't going to last long. He could
feel his balls churning and tightening in his scrotum, and he gaze Green a thumbs
up that he was about to cum. Green pulled out the pink vibrator they had used on
Tiffany in the Lincoln and jammed it up inside her pussy, already turned on and
buzzing madly. He pinched her clit between his thumb and forefinger and began to
squeeze it rhythmically, gently but firmly.

The beautiful young victim nearly went insane when the vibrator hit her sensitive
pussy and her English teacher upped the ante on her love button. She was getting
fucked up the ass with one cock, fucked up the pussy with a fake cock, her clit
felt like it was about to explode.

And then it did. Tiffany Daniels launched into her orgasm just as Mr. Brown's
cock swelled even larger and began to pump a huge load of sperm up into her

Tiffany screamed with pleasure, but the scream was trapped by Old Joe's buttocks
covering her mouth. The scream went right up into his asshole. Her hips bucked up
and down wildly, her entire body tensed and went rigid, the muscles in her rectum
clamped down ferociously on Brown's cock as he emptied gush after gush of hot
semen up into her bowels. Green could hardly hold onto the girl's slick clit as
she writhed frantically on the cafeteria table. It was as if her entire body was
being jolted by blasts of electricity as she jumped and wiggled.

"Mmmmmppffffffff!" the girl bellowed with pleasure into Joe's asshole. The
janitor raised himself up a couple of inches, depriving himself of the pleasure
of her rimjob so that everyone could hear her orgasm.

"Yessssss! Oh God yesssssss!" the cheerleader yelled as she continued to cum.
Finally, after about 10 long seconds, she began to subside, and Brown withdrew
his cock, which was still stiff, and now coated with his own jism and Tiffany's

"Who's next?" he asked with a leer. In a flash, Tom Green, her English teacher,
had moved to the edge of the table where her asshole, now gaping open somewhat,
waited, poised, to be filled again. He didn't wait, but plunged his tool in
immediately. Unlike Mr. Brown, he didn't have to ease her into the anal fucking.
He just shoved his cock in, as hard and as far as he could. Tiffany's eyes bulged
out in surprise, but she was well- greased enough that it didn't hurt. In fact,
it felt good to be filled up again.

"Oh yeah, oh yeah, oh yeah," she started muttering. Her head whipped from side to
side, banging against Black's thighs. White motioned for the janitor to climb
down off the table, and he did so. As soon as he was down, White aimed the video
camera at the young beauty's face.

"Tell us what you want, Princess," the principal said. "If you like that feeling,
tell us!"

"Feels so good!" Tiffany managed. "More! More! More!"

"Tell us exactly, Princess, or we're gonna stop and you won't be allowed to cum
anymore," the older man guided her.

"I want to cum!" she panted. "Cum! Cum! Cum!" The former cock tease had been
teased for so long that now, when she was finally being granted a sexual release,
she had entered another plane of existence. She was barely aware of the men
around her, focusing only on the incredible feelings coming from her pussy and
ass. Her eyes were squeezed shut, and White's voice seemed to come from some
distant place, an order that she had to follow to keep the good vibrations

As Green stood at the foot of the table, plunging his cock in and out of the
teenager's ass, he reached down between her upturned legs, between her handcuffed
wrists, and located her clit with his fingers. He began again to rub it, again
sending the girl shooting upward.

"Do you like the cock up your ass, Tiffany?" asked White. "Do you like having
your clit rubbed? Tell us what you like, Tiffany, or we'll stop."

"Don't stop!" she moaned. "Please don't stop! Make me cum! Fuck my ass! Play with
my clit! Please fuck me, fuck me, fuck me, fuck me, don't stop!" The more she
said it, the more she felt it. Her desire now permeated her whole being, became
her entire being. White focused the camera tightly on the girl's face as she
begged to be fucked in the ass. It would be the perfect climax, so to speak, of
the video scrapbook the men had been compiling, the one he was mentally calling
"Toying With Tiffany."

Tiffany wasn't the only one who felt as if she'd been teased for the past few
hours. Green and the other men were practically going out of their minds with
unslaked lust, and the juicy friction of his cock rubbing against the walls of
the cheerleader's rectum soon proved to be more than he could bear. Even though
he wanted to make it last, he was soon ready to blast her ass with another load
of sperm.

Tiffany felt her teacher's cock head swell inside her ass; it felt like it was
the size of a tennis ball. But it was the magic fingers diddling her clit that
had most of her concentration, as the youngster approached her second orgasm of
the night. She had forgotten about White's instructions, and was now just
screaming for more of her own free will.

"Yes! Yes! Fuck me! Fuck me! Make me cum!"

The English teacher obliged her, groaning loudly as he emptied his balls into the
student. He roughly gripped her clit and shook it from side to side, like a dog
playing with an old sneaker, and Tiffany once again went rigid with an
overwhelming orgasm.

White turned off the camcorder, having gotten the footage he wanted. He was dying
to fuck the blonde cheerleader, and had moved around to stand behind Mr. Green.
Mere seconds after Green had withdrawn, White rammed his hard-on deep into the
girl's bowels. In Tiffany's swirling, lust-crazed mind, it was as if the
ass-fucking had never stopped.

Joe Black looked at the girl laying on the table, the bitch-princess who had
never even noticed his existence as he pushed his mop and bucket around the halls
of Daniels High. Her mouth was open and she was breathing heavily, and he decided
he wanted to put that mouth to more good use. So he climbed back up onto the
cafeteria table, knees planted on either side of Tiffany's head again, and
lowered himself onto the cheerleader's face. His aim was true, and he managed to
maneuver his dangling scrotum right into her gaping mouth.

Tiffany was startled by having her mouth suddenly full of the janitor's heavy
balls, but by this point she was on automatic pilot, and just moaned. Her moaning
vibrated her mouth, which vibrated Joe's testicles, giving him the most exquisite
pleasure imaginable. He just knelt there, unmoving, letting his scrotum get a
hum-job from the teenager. His cock, huge and purple, waved in front of him like
a divining rod, one that sensed teenaged ass instead of water.

As Tiffany tickled the janitor's balls with her tongue, Principal White was
practically a blur between her legs. She was now slick enough from two massive
doses of semen shot up her butt that he could ram away on the girl as if she were
a piece of meat, which is exactly what he did. He did not neglect her pussy and
clit, though, knowing that if he could give her a third orgasm, she would clench
her muscles so tightly that he would have one of the greatest orgasms ever.

Joe pulled his balls, wet with teen saliva, from Tiffany's mouth, and scooted
down the table a short distance. He knew their time was growing short, and he
wanted some more rimming from the girl. He saw that Brown had picked up the
camcorder and moved in close, framing the shot so that all that could be seen was
Tiffany's face, glazed with lust and drool, and the anonymous midsection of a
middle aged black man hovering over her. Joe lowered himself down onto Tiffany's
face as the camcorder captured every moment.

"Lick my ass, Princess!" Joe commanded. "Ream me out with your tongue. The
farther you get your tongue up my ass, the bigger the orgasm you're gonna get."
Tiffany was at a point where everything said to her seemed like a command she had
to obey, and she obediently stiffened her tongue and drove it as far as she could
up between the janitor's butt cheeks. She penetrated his anus with her tongue,
and kept going, inch by inch, until her tongue began to ache.

"Now wiggle that tongue, Princess," Joe ordered, and Tiff again obeyed, moving
her tongue as best she could within Joe's tight asshole, giving the man the
sweetest rimjob he had ever had in his life. She was so insane with lust that she
was barely aware of the musky, sweaty odor and taste of the asshole she was
rimming wildly.

Inevitably, White's orgasm hit, just as Tiffany's third orgasm of the night
launched like a Saturn 5. For the third time, she felt wave after wave of
pleasure wrack her delightful young body as her principal emptied his seed into

Joe reluctantly climbed down from his perch on Tiffany's face. He had fucked
plenty of girls at Daniels High during his recent career of blackmail and
humiliation, but the rimjobs had been a recent addition to the gang's repertoire,
one that combined extreme pleasure for them with extreme degradation for the

But his monster cock needed satisfying, and he moved into position with the head
at the entrance to Tiffany's bunghole. Joe had gone last for a reason. Although
racial stereotypes frequently are false, in this case there was some truth. Joe
Black was hung like a stallion, and the other men had discovered a while back
that if they let him go first, he would ream the girl in question so far that she
wouldn't be tight enough for them. So Joe had become the clean-up hitter, and now
he rammed his baseball bat of a cock home into the cheerleader.

"Ahhhhhh!" Tiffany screamed, this time in pain. Even with a thoroughly reamed-out
asshole swimming in semen to provide lubrication, Joe''s Dirk Diggler of a dick
hurt. "Noooo!" she wailed. "Take it out! It hurts." But Joe ignored, and while
his comrades in torment watched, began to fuck the girl's ass in earnest. In and
out, in and out he pumped, and gradually Tiffany's protests subsided as she got
used to the ravishing.

White unlocked her handcuffs, which allowed her to spread her legs. He took her
hands and placed them on her pussy, and instantly her fingers began a frantic
dance on the surface of her clit, rubbing the hard, swollen nub for all it was
worth. Soon she was once again screaming "Yes! Yes! Fuck me! Make me cum!" as
another orgasm built in the girl.

When it hit her, it was the biggest one yet. Her blue eyes rolled back in her
head, her face went red, her whole body rigid. Green had leaned over her with
both hands and was tugging on her erect nipples, pulling them gently but firmly
upwards, adding to her pleasure. As her muscles tightened, her rectum clamped
down on Old Joe's prick, and he began to cum, gushing his hot sperm up inside
her, the fourth time in the evening she had gotten an assfull of thick, salty

After a few moments, the cafeteria was completely quiet. Tiffany and Old Joe were
both panting. White and Green were already pulling their pants on. It had been
quite an evening, but tomorrow was a school day!

"So Princess," asked Mr. Brown, "what did you think about your first fuck?"

Tiffany was coming back to reality, realizing where she was and what had
happened. The buzzing in her firm young body was dying down, and she was now very
aware that she was laying naked on a table in the school cafeteria, that she had
been fucked up the ass by four men. And the worst part was, she had wanted it!
She had begged for it!

Suddenly a wave of shame and humiliation washed over the confused girl. All those
names they had called her on the way to the mall, slut and whore. It was true!
She was a slut, a whore, a worthless scumbag. She hadn't wanted them to do this,
but when they did, she had liked it! How could she face them again? How could she
facer her parents, her friends, her little sister Stephanie?

The day had been a long one. It had started that morning with Principal White
putting ants up her ass and her pussy, which she had suffered with through the
school day. Then had come the humiliating trip to the mall, the blow jobs, being
forced to strip in front of other people, the horrible songs, everything. And
after all that had been done to her, her response had been to get excited and cum
over and over!

"Up you go, Princess Tiffany," said Mr. Green, helping her sit up on the table.
She was so embarrassed, and put one arm across her breasts to shield them from
the view of the men. They all laughed, and she realized how absurd it was to try
to cover herself.

"Here's the clothes you came to school in," White said, holding out a bag. "You
need to wear them home so nobody gets suspicious. We'll keep all the stuff we got
at the mall here at school. Now get dressed, and you can just make it home on
time." He patted her condescendingly on the head, as if she were a five-year-old
or a puppy dog that had successfully been paper-trained.

In a daze, Tiffany got dressed.

"Tomorrow morning, I want you to report to my office first thing in the morning,"
White told her. "Don't even think about calling in sick, or I'll plan an audio
tape of you begging to be fucked in the ass over the loudspeaker for the morning
announcement. It'll seem like an accident, and I'll be safely somewhere else when
it happens. But just imagine how your girlfriends on the cheerleading squad will
react when they hear your voice. Or even better, just imagine your sister
Stephanie sitting in freshman homeroom, listening to her big sister hollering
"Make me cum!

"So tomorrow morning, first thing, my office," he repeated to make sure she
understand in her dazed and confused state. "After all, tomorrow is another day!"

Review This Story || Author: Dr. Wu
Previous Chapter Back to Content & Review of this story Next Chapter Display the whole story in new window (text only) Previous Story Back to List of Newest Stories Next Story Back to BDSM Library Home