High School Musical: Blackmail (mf,ff,inc,anal,BDSM,bmail,humil,reluc)
by Hamster ([email protected])
"Pleeeeease Sharpay, Please...please." Ryan whined.
"No." Sharpay said firmly.
"Please I'll die if I don't." Ryan said.
"I'll be sure that you get a very nice funeral." Said Sharpay.
"God Sharpay I really have to have it." Begged Ryan.
"There is no way in hell that I am going to let you fuck me in the ass."
"But I let you fuck me in the ass with your strap-on." Ryan countered.
Sharpay grabbed him from the front of the shirt and pushed him against the
"That was to show you just who the hell the boss is. Apparently you failed
to grasp that." She said.
Ryan was rock hard now. He was turned on anytime his sister got all rough and
assertive. He desperately wanted her ass. It was so pleasingly shaped...it
was all that he could think about. But she wouldn't let him fuck her there,
she wouldn't give him a blowjob either. Sharpay wouldn't engage in any sex
she found demeaning, at least demeaning to her. Sharpay had no problem
demeaning Ryan. She WOULD ride his cock sometimes though. Those times made
it all worth it.
"What if I did something for you?" Ryan said.
"There isn't anything you can do for me that I couldn't just take from you if
I wanted it." Sharpay pointed out.
"Uhhh OK, but what if I came up with something?" Ryan asked.
"Like what?" Asked Sharpay as she let him go.
"Well you hate Gabriella right?" Asked Ryan.
"Passionately, what's your point?" Sharpay said.
"What if I could get you some really good dirt on her? Something you can
really use against her?" Ryan said.
"Yeah right, that girl is squeaky clean." Sharpay laughed.
"Nobody is perfect Sharpay. There has to be something that she's hiding."
Sharpay thought for a minute. If she agreed, his odds of success were quite
slim. The added benefit would be that Ryan would be off her back for a while.
"OK Ryan, here's the deal. You get something that I can use against her and
I'll let you fuck me in the ass just once." Said Sharpay.
"Deal." Ryan agreed before they both shook hands.
* * *
Ryan had been following Sharpay for a solid week. He had become a sort of
amateur detective. He had recording devices and several disguises all of
which he used in his efforts at stalking Gabriella. It took very little time
for his efforts to pay off big. Ryan followed Gabriella to a gentlemen's club
on Sunday night. He tried to get through the front door but he was greeted by
"ID?" Demanded the rather large ape-like man.
"Uhh I forgot it, but I have a friend in there I just want to talk to her
real quick and I will be right back out." Said Ryan.
"Go away punk." Said the bouncer.
"Look do you know who I am? I'm Ryan Evans, my family owns half this town."
"You know who I am? I'm the bouncer Tom. Tom says no ID no entry." Tom
"I’m going in there on way or the other." Said Ryan.
"KNEEL BEFORE TOM!" Tom cried before knocking out Ryan cold.
Ryan woke up in the trash dumpster behind the club.
The next week Ryan was better prepared. He had a fake ID with him as he
followed Gabriella who once again showed up at the club. Tom once again
confronted Ryan at the door.
"ID?" Tom asked.
Ryan presented him with his fake ID.
"It's fake." Tom said flatly.
"How could you possibly know that?" Ryan said.
"If you had a real one you would have just given it to me last week." Tom
"Does this help." Ryan said as he passed the big man a 100-dollar bill.
"Step right in sir." Said Tom.
Ryan sat at a table and ordered a drink.
He watched two girls strip and noticed that both of them looked like
teenagers. The third girl he was certain was a teenager because it was
actually Gabriella. He watched as she came out and started doing a really
hot pole dance in a skimpy outfit. Eventually she lost the top, the bottom
and finally all she was wearing was her g-string. He was snapping pictures
with his digital camera during her entire act. Afterwards she did lap dances
for several customers. Ryan wanted a lap dance but he figured it would be a
bad idea to tip his hand and let her know he'd seen her.
* * *
The next day he provided the pictures to his sister Sharpay.
"OMIGOSH!!! This, this is fucking perfect. This is exactly what I wanted.
This is something I can really use. Gabriella is going down so fucking hard,
she doesn't have a clue." Sharpay was practically moved to tears.
"Great, now you can give me what you owe me." Said Ryan.
"Huh? But I didn't think you'd...what I mean is that I wasn't....I uh,"
Ryan walked over to her and put a hand on her hip, he slid it over her ass
"A deal is a deal," he said.
He was right, she was stuck. No way out. Now Ryan was the aggressor. He
pushed his hot, blonde sister over to her bed and bent her over it. He rolled
her skirt up and then pulled her underwear down. His sister's ass was now
exposed and ready for his enjoyment. He couldn't believe how hot Sharpay's
body was. Now the magnificent ass that had been so unfairly denied to him for
such a long time would finally be his. He guided his rod to the entry point
and then grabbed her full gorgeous hair. He pulled back hard as he thrust his
cock in good and deep. Some girls liked getting fucked in the ass and some
didn't mind it, Sharpay was not one of those girls. She bit her lip and dug
her nails into the mattress as her brother pounded her booty with relentless
strokes. With each thrust he pulled back on her hair and she was wailing and
tearing up as he did so.
"OH FUCK! SHIT! HELL!!! DAMMIT!!!" Sharpay cried.
"YES! YES! IT'S SO GOOD, SO DAMM TIGHT!!!" Ryan cried as he pounded her.
He let go of her hair and gave her ass a good hard smack before blowing his
load in her. Sharpay crawled away from him then pushed him away.
"OK you got what you wanted now get the hell out of my room." Sharpay cried
Ryan exited with a dopey smile on his face. Sharpay was crimson with rage.
Somebody was going to have to pay for this humiliation. Sharpay looked over
at the pictures of Gabriella getting her stripper act on. She had a pretty
good idea who.
* * *
Gabriela was walking down the hall when suddenly she was tapped on the
shoulder. She turned around and was confronted be the sight of Sharpay and
Ryan, both of whom were looking quite smug.
"Uhh hello." Gabriela said.
"Hey." Said Sharpay. "I have something that you should see."
Sharpay handed Gabriela a plain manila envelope. Gabriela looked confused,
she opened the envelope and found that inside was a set of pictures. The
pictures made her eyes pop wide open.
"How did you get this?" She demanded.
"Doesn't matter, what does is that if you don't come to my house tonight
at 7, the entire school is going to find out what a filthy slut you are."
Sharpay said. Ryan and Sharpay walked away from the poor, horrified Gabriela.
Sharpay stopped in her tracks then turned towards Gabriela. "Oh and Gabriela,
please were something nice."
* * *
It was 7pm and Gabriela rang the doorbell nervously. She wondered what
Sharpay had planned. What was she going to do to her? Sharpay opened the
door and Gabriela's heart sank. Time to face her doom.
"Hello Gabriela, come on in." Sharpay.
Gabriela was wearing a red dress and looked nauseatingly cute.
"Sharpay, I...I only danced at that club because my family really needs the
money." Gabriela started.
"I see you want to get right down to business, so here you go. I will give
you double whatever you make at that club." Sharpay said.
"What?" Asked Gabriela as she blinked in shock. "Why?"
"Because you are going to be me and Ryan's own personal slave. You are going
to do everything you did at that club and a whole lot more for us." Sharpay
"Forget it, I won't do it." Gabriela said.
Sharpay stood and slapped her across the face.
"I get what I want. Do you understand that? If you don't do what I say, the
whole school will see those pictures. Even your precious boyfriend Troy.
Understand?" Sharpay yelled.
Gabriela rubbed her cheek and a tear rolled down from her eye. "I understand.
I understand that you are a heartless bitch."
"That's right, and I'm the last heartless bitch that you ever want to fuck
with. So do we have a deal?" Asked Sharpay.
"Yes, yes we do." Gabriela said a she looked downcast.
"Good, follow me." Sharpay said before she led Gabriela up the stairs to her
Ryan was already waiting for them. Sharpay went and sat down next to her
"Alright Gabriela strip." Sharpay ordered. Gabriela reached back to the back
of her dress but was having trouble with the zipper. Sharpay rolled her eyes.
"Ryan help her."
Ryan got up and unzipped the back of her dress then sat down next to his now
slightly impatient sister. Gabriela let her dress fall to the ground and
stood there wearing red panties and a red bra. Gabriela took off her bra
next. Then slid her panties down. She stood there naked and self-conscious
while Ryan and Sharpay appraised her like a piece of meat. Sharpay stood up
then walked over to Gabriela and squeezed her tits.
"Hmmm, not bad." Said Sharpay. "Ryan you should feel them."
Gabriela's humiliation deepened further as Ryan stood up and fondled her
"Nice." Ryan said.
"Glad you like them." Said Gabriela sarcastically.
Not liking her attitude, Sharpay decided to get mean(er).
"Ryan you like anal right?" Sharpay asked.
Gabriela's eyes grew wide with alarm.
"Hell yes." Ryan.
"Well why don't you try some of this sweet ass." Sharpay said as she gave
Gabriela's butt a nice hard slap.
"OH HELL YES!!!" Ryan exclaimed with excitement.
Gabriela turned to Sharpay.
"Please not that." Gabriela begged.
"You need to improve your begging skills girl. Get on the bed before I make
things REALLY unpleasant for you." Sharpay actually intended to make things
very unpleasant either way. Fighting tears, Gabriela got on the bed, face
down. "Good little whore. Now beg him for it. Beg him to stick it in your
"Please, please Ryan. Please stick your cock in my ass." She said
pathetically through a haze of tears.
"You got it, no problem." Ryan said with considerable enthusiasm.
Ryan undressed in a hurry.
"Ryan make sure you use her hair as reigns." Sharpay said as she thought back
to her own humiliation on at her asshole brother's hands.
Ryan didn't need a whole lot of encouragement. Gabriela, who just wasn't used
to rough treatment, wailed and clawed at the mattress as he plumbed her ass
with his cock while yanking back on her hair with each and every stroke.
After several strokes he was filling her ass with his chunky man-chowder.
"Nice work, Ryan." Sharpay said approvingly. "Now get out."
"What? But, but why I want to..." Ryan began to protest.
"I want some alone time with little miss sugar-sweet and innocent." Sharpay
"But Sharpay please..." Ryan stammered.
"Just shut up and leave." Sharpay ordered.
As soon as Ryan slunk out, Sharpay took her index finger worked it into ass.
She slid out the cum-soaked finger and then held it in front of Gabriela's
lips. She shook her head. Sharpay slapped Gabriela's ass hard and held it in
front of Gabriela's face once again. This time she opened her mouth and
sucked the cum-coated finger like a baby with a bottle. Gabriela started to
think quickly. She knew with absolute certainty that Sharpay had some plans
for her and that she would NOT like them. She formed a plan in her head for
defusing whatever pain and humiliation Sharpay intended to visit upon her.
"Sharpay please let me eat your pussy." Begged Gabriela.
Sharpay blinked. Sharpay was shocked by Gabriela's sudden cooperative
"Hmm, that sounds like a very good idea." Sharpay said as she sat on her bed.
"Take my shoes off."
Gabriela obediently removed Sharpay’s shoes. At Sharpay's command Gabriela
then unbuttoned Sharpay's pants and unzipped them. Gabriela pulled her blonde
mistress's pants off and then her panties. Gabriela proceeded to lap away at
"Mmmm yes, good girl." Moaned Sharpay while stroking Gabriela's hair.
Gabriela took great care to thoroughly eat out the blonde's hot, wet pussy
in the hopes that she'd be in a better mood once she came. Sharpay's body
started to shudder as she came to an orgasm. "Hmm yes Gabriela that was
very nice. It's your turn now."
Gabriela thought that Sharpay meant she'd return the favor but her
blackmailer actually just got up and went to a drawer where she retrieved a
"Please Sharpay not that! I'm a virgin I'm saving myself..." Gabriela begged
"Awe that's so sweet. But it looks like you were saving yourself for ME.
Doggy-style, now." Sharpay ordered. Reluctantly the miserable girl obeyed.
Sharpay approached Gabriela as she strapped herself in for the ride.
"Sometimes I fuck Ryan's ass with this. It's never tasted sweet pussy
Sharpay began slowly sliding the false cock into Gabriela's pussy until she
met with resistance. Viciously she thrust in as hard as she could and made
Gabriela wail in agony. Pain gave way and soon, despite herself she was
enjoying the repeated strokes on Sharpay's hungry dildo. One of Sharpay's
hands went to her pussy and she began to finger herself as she fucked the
virginity out of Gabriela. Victim and victor were both cuming together.
Afterwards they lay next to each other on the bed.
"Poor Troy is going to be so disappointed when he slides his cock in your
cunt and finds that somebody beat him to the cherry. Listen up, you will be
here once a week. Each time you 'visit' I am going to do whatever the hell
I want to you. And, if I'm feeling especially generous, I'll let Ryan fuck
you in the ass understand?" Sharpay asked.
"Yes." Gabriela whimpered.
"Yes what?" Demanded Sharpay.
"Yes, mistress." Gabriela replied timidly.
"Good little slut." Said Sharpay. "I think that sluts need to be punished,
don't you? You like to dance naked for strange men don't you? Then you
definately need some punishing. Put your hands on the wall."
Gabriela got up and slunk over to the wall put her hand up against it.
Sharpay found one of her belts and begand to whip Gabriela across the ass
with it. Gabriela howled as the belt struck her ass over and over. Sharpay
whipped viciously but Gabriela was becoming aroused in spite of herself.
Once Sharpay was satisfied with the savage assault on Gabriela's butt she
put her finger up Gabriela's cunt then licked them.
"Tasty." She said. "Now get your cloths on and get the fuck out of my house,