Beauty and the Bully
Caution: This BDSM Sex Story contains strong sexual content, including mt/ft, mt/mt, Reluctant, Coercion, Blackmail, BiSexual, TransGender, CrossDressing, DomSub, MaleDom, FemaleDom, Spanking, Rough, Light Bond, Humiliation, Gang Bang, Oral Sex, Anal Sex, School,
Desc: BDSM Sex Story: Chapter 1 - Jason is tormented, caught, blackmailed and fucked but does that all really sound that bad? Maybe not for Jason.
The sun was high in the sky, yet a cool breeze blew over the busy metropolitan city of Kingston, California. The students at the local high school, Kingston High, were outside enjoying their half hour of lunch under the warmth of the sun high overhead.
Jason Lane darted nervously between the buildings on his way to his next class. Most of the other students were in the quad where the lunch lines and picnic tables were. Jason wasn't trying to avoid those kids. No, he was trying to avoid the bullies. Clifford Johnson and his friends to be exact. Cliff had been picking on Jason for a few weeks now and Jason was fed up with it. It had been easy to ignore at first, the rude comments and teasing about his looks, but now he was getting physical and threatening. Jason had considered going to the principal but Cliff had threatened to beat him within an inch of his life if he ever did that. Jason didn't think he would ever do that but he preferred not to test the theory. So far he hadn't gotten more physical than some occasional jostling so it was worth not saying anything.
Jason was a small boy. He was about 5' 6" and only weighed around 130 lb. He had long brown hair down to his shoulders that he had started growing out his freshmen year. He passed it off as a heavy metal grunge look but in truth he was very proud of his locks and thought they looked great when he straightened them. He was quite skinny and tended to avoid physical activities as a rule and therefore never developed the musculature that men tend to have. Jason had delicate, almost girlish features that, many people often commented, made him look beautiful. They were also the focal point of his torment. He had a small, round nose, a rounded chin and a soft jawline. When his hair wasn't pulled back into a ponytail it would fall gracefully around his face. Besides his head, his body was naturally devoid of hair; he had yet to used a razor.
Since he stayed away from most of the athletic groups, people tended to label him as a nerd. This was partially true since he was a smart kid and he studied hard and got good grades. But Jason never really thought of himself as a nerd. He was an introvert certainly, but he never used a pocket protector and he wore his backpack on his two shoulders like everyone else. However, at school he had very few friends and he tended to spend his lunches alone. At home he spent much of his time with a group of friends he played online games with.
Jason snuck past the library and skirted around the edge of the main quad. He caught a glimpse of Cliff on the other side as he was leaving the lunch area. Thankfully Cliff hadn't glanced toward him.
Jason was heading for his next class already. He liked to sneak in during lunch so he didn't have to deal with anyone else while at the same time getting some homework done so he wouldn't have to do it at home. Jason and his friends were deeply involved in the latest first-person shooter that had come out for Xbox. They spent most of their time playing the game, Jason less than the others because he tended to study and do more homework than they. Yet since they were his only real friends, he looked forward to when he could sit down after school and play with them.
The sounds of the kids in the cafeteria dwindled as Jason entered the vacant classroom block. The block consisted of one large building in the center with ten newly constructed classrooms, five on each side of the building with their entrances opening into a common hallway running between them. Around this were several rows of individual classrooms. It was dim and cool inside the building and the only sound was the air conditioning humming in the background as if fought off the midsummer heat.
Jason slipped quietly into the building. He walked down the hall and peered through the small window into the classroom at the end. It was empty and dark except for the spears of sunlight that slashed across the classroom as the shades swayed back and forth.
Jason entered and took a seat in the corner, out of direct sight from the door. He unzipped his backpack, ruffled through some papers to find his report and began to work on it. It was a history report on cars and their effect on the economy. Jason had been working on it for a few weeks now.
He glanced at his watch. Twenty more minutes until lunch is over.
The sound of a door opening echoed down the hall. Jason looked up, watching the door. He waited for someone to walk by but the window remained empty. Whoever it was, they must not have come down this far, he figured. He went back to working on the report.
The click of the door being open startled Jason from his daydreaming a minute later. He looked up to see Clifford Johnson walk into the dim classroom. This lunch hour had just taken a turn for the worst, he groaned.
Clifford Johnson was about six foot tall. He was a big guy seeing as he was on the football team. His cut off t-shirt revealed the large muscles that wrapped his biceps and forearms. He had a taunting smile on his face, a grin of satisfaction at having caught his prey. His clean-shaven scalp gleamed as he passed through a blade of sunlight.
Jason swore to himself and tried to ignore Cliff. He found this impossible, though, as Cliff walked up and snatched the papers from Jason's desk.
"Hey Jason, I didn't see you outside with everyone else so I decided to look for you. I was concerned our little girly nerd had gotten herself into trouble or something. Good thing I found you, 'cause you look pretty lonely. How about I hang out with you for a bit and see if I can't cheer you up."
"No Cliff, I have homework to do. I need to concentrate. Can you give me back my report, please?" Jason replied, avoiding Cliff's eyes. He hated when Cliff did this to him. A quick glance at the clock told him he would have to endure Cliff for another eighteen minutes or so.
"Ah, come now. A smart girly boy like you shouldn't need to study so much. It's not good for you. Besides, if you want your papers back, you're gonna have to come over here and hang out with me." Cliff sat down in a chair next to Jason and started to shuffle through the homework.
"Cliff, no, give those back. Come on, I need those papers, that was a lot of work!"
"Ohhh, this sounds important, 'The History of Modern Transportation and Its Importance to Our Economy.' Are you sure you shouldn't be writing about the history of men and how they shouldn't look like girls? You might find out what happens to boys when they look like girls."
"Fuck off Cliff, that's gross Cliff, what are you gay? Give me back my report and I won't tell on you," Jason said, angry now but at the same time trying to fight back tears of humiliation. He hated it when Cliff made fun of his looks. He silently cursed his parents once again for bestowing him with such feminine features. They had caused him nothing but trouble since the age when boys became interested in girls.
"Give me back my report or I'll tell on you," Cliff whined, imitated Jason in a squeaky, high pitch voice. "Shut up dweeb. If you want your report back, do as I say or I'll shred it right in front of you. Come over here and sit in my lap like a good little girl. If you're nice enough to me I'll give it back to you."
Jason signed and walked around his desk to Cliff. He stood before him for a moment until Cliff, watching him silently, patted his knee. Jason blinked back tears and sank down onto Cliff's lap. He couldn't help but feel humiliated that he, such a small guy, was sitting delicately on Cliff's knee. Cliff slid a hand up Jason's back and pulled the hair tie from his hair. Jason's long brown locks fell to surround his face, hiding it from Cliff's gaze.
"There, now you look much more like the girl you secretly desire to be. All you need is a little skirt and some make-up and you could be such an adorable little girl. Hey, why don't you try on some of your cute sister's clothes? I remember seeing her in a few hot numbers before."
"Fuck you Cliff, leave Megan alone," Jason snapped. He loved his sister and didn't want this cocky Neanderthal anywhere near her.
"Oooh, a little touch aren't we? Hey, I think it's time for a little education now. Then I'll give you your paper back. You need to learn you place as a woman if you are gonna look like one." He stared down Jason, daring him to disagree. "Get on your knees and suck my cock," Cliff commanded. Jason shook his head violently, horrified at the thought of his mouth anywhere near Cliff's dick. He wanted to say no, to get up and run from the classroom but the fear of getting beat up held him back.
"If you don't get on your knees right now I will rip your paper to shreds and I will punch you so hard you won't be back to school for a week," Cliff threatened, his hand sliding up Jason's back to grip his hair painfully.
Jason whimpered in resignation as Cliff pulled his head back, exposing his slender neck. He bit his lip to hold back tears but failed, a few managed to escape and rolled down his cheeks. Cliff let go of his hair and Jason slid off his lap to kneel in front of him, sobbing quietly. Cliff leaned back in his chair; knees spread wide and waited Jason.
"Tell me you want to suck my dick now," Cliff demanded, his hands clenching into fists. Jason saw them and knew he had no choice. Another tear burned a trail down his cheek.
"Please, let me suck your dick Cliff, I really want to," Jason said, sobbing and reached for Cliff's crotch. Suddenly Cliff batted his hand away and stood up. He towered over Jason, who fell back onto the flour stunned.
"Fuck no, you little queer. I ain't letting you suck me off, I'm not gay. But thanks to my friends," he indicated the two people walking into the room holding a video camera, "everyone will know that you are." The bell signaling the end of lunch chose that moment to ring. "Enjoy being known as a faggot, little sissy," Cliff jeered at Jason. He threw Jason's paper on the floor and left the room laughing with his friends.
Jason covered his face and cried. He was horrified that anyone would see that video now. Too terrified to face his fellow classmates, he hurriedly crammed his stuff into his backpack and ran from school not caring that he was ditching for the first time in his life.
Jason fled to his room as soon as he made it home. He turned his stereo on, blasting Muse, and crashed onto his bed. He buried his face in the pillow and cried. He tried his hardest to wish it all away. Prayed that it was all a dream and he would wake up shortly. Yet Stockholm Syndrome continued to course through his body.
He didn't wake up, he was not dreaming and he lay in bed crying for a while until there were no tears left. He didn't want to face another day at school. He didn't think he could return knowing that everyone had seen him on his knees, begging to suck Cliff's cock.
Eventually he picked himself up off the bed, drying his eyes with his shirt. He looked around at his room; it was a tribute to all that was heavy metal. He had band posters covering much of his walls. All his furnishings were painted in black and he had a number of gothic and horror icons scattered around the room, on his desk and shelves.
It was all a facade though. He was not the heavy metal rocker that people would assume he was if they ever saw his room. He wasn't the nerdy bookworm that kids at school saw him as either. Jason loved these bands with all his heart but deep down he knew he was meant to be something else; a girl just like everyone made fun of him for. That's why he tried so hard to look different. In truth, he hated the dark colored clothes he normally dressed in. He wanted to wear his hair long and pretty like a girl and dress in pink and bright colors. He hated the fact that when he had knelt before Cliff and begged to suck his cock, part of him really wanted to find out what it was like.
Jason began wandering the house, wondering what to do until his family came home. He knew he would be in trouble when they did but until then he needed to find something to do, something to take his mind off the thoughts of the humiliation he would face from his fellow students.
His wandering brought him past the open door of his sister Megan's room. It was a very feminine room full of everything he secretly wanted for his own. Pink coloring and posters of popular bands adorned the walls. What caught Jason's eye, though, were the panties lying in the middle of the room. They were fascinating to him because they were the physical representation of his deepest desires. He pushed the door further open and entered his sister's room.
The panties were a soft black lace thong style cut and had pink polka dots and a little pink bow on the front. He felt a stirring in his cock; he wanted to put them on. He hurriedly stripped off his clothes and slowly slid the panties up his legs, enjoying the soft material as it clung to his body. He loved the feeling of the smooth lace tight around his butt and encasing his hardening cock. He needed more.
He dug into his sister's drawers and picked out a little pink and black skirt she owned but rarely wore. It was short, barely coming down to mid-thigh and showed off his smooth, skinny legs. He knew the panties would be seen underneath if he were to bend over. He found a black baby doll t-shirt that completed the ensemble and stood in front of Megan's full length mirror to admire his new look.
He twirled around. The skirt flared out a bit, showing off his cute butt covered in the polka dotted panties. He groaned with desire for the sultry vixen in the mirror, his cock straining to get out of the tight material it was trapped in. His narrow waist and rounded butt gave him an hourglass shape. However, without breasts he still looked like a boy but he could definitely see where a little make-up and hair styling would turn him into a beautiful young girl. He was scared to try any though, having only caught glimpses of his mom and sister applying theirs. He had no idea where to start.
With the music pumping loudly in his room across the hall, Jason never heard the front door open. He also didn't hear the girls coming up the stairs. But he certainly noticed the cries of the three teenage girls as they burst into the room, shocked to discover a boy dressed in women's clothes.
"Jason! What the fuck are you doing?" Megan shouted. She was standing just inside the room, shocked to find her younger brother dressed in her shirt and miniskirt. Her friends Casey and Becca were with her. She and her friends had their backpacks with them and since school still had two more hours to go, Jason assumed they were ditching as well. Of course today would be the day she ditches also, Jason thought. He stood frozen, mouth hanging open and eyes darting back and forth, completely unsure of what to do.
"Na, na, nothing M-Megan," he stammered. "I was just ... seeing if we still wore the same sizes! That's all"
"Oh this is good," Casey muttered. She held her iPhone up and started snapping photos of Jason while Megan berated him.
"Bullshit, you have a fucking woody under that skirt, I can see tent. It looks rather small though, I guess you really are my little brother," Megan smirked. She strode into the room and slung her backpack onto the bed. Her friends followed her, snickering to each other and laughing at him. They were all wearing their cheerleading uniforms. There had been a school spirit demonstration during lunch today, Jason remembered. They must have ducked out soon after. "I think you look lovely dressing up as a girl though. Have you finally admitted to yourself that you should have been a girl?"
"No, honest Megan, I," Jason tried to get out before Megan interrupted.
"No you don't like it, or no you haven't admitted it to yourself yet. Cause from here it looks like you're sure enjoying that skirt. What do you have on under there anyways?" Jason tried to keep the skirt pulled down as he moved away from Megan but she trapped him and yanked it up anyways. "Ohhh, the pretty panties I wore yesterday. Don't they just fit you so well, honey?"
"No Megan, stop it, stop making fun of me. I'm a boy, let me go. I don't want to wear this anymore. Just let me go to my room, please!" Jason glanced wildly around the room and then darted for the door. The girls jumped into his path, blocking him and backing him up to the bed. Megan pushed him down and leapt onto him, pinning him to the mattress with her muscled cheerleading legs.
"Nope, you're my little sissy now Jason and I'm gonna make you pay for being such a little brat to me. What are you doing here anyways? I thought you were like, a super nerd and into school and all that," Megan said.
"Yeah, I heard from Derek, who heard from Daniel, who talked to Justin, who said that you get A's on all your tests and ruin the curve for the rest of the class every time," said Casey. She was grinning at Jason, enjoying the feeling of having power over the boy. The girls all loved this feeling. That's why they joined the cheerleading squad in the first place, for the power their position granted them over the male population of the school. All the boys and many of the teachers simply bowed to their wishes when they came sashaying by in their cute little skirts and tight blouses.
"That doesn't even make sense Casey. I don't have a class with Justin, so how would he know anything?" Jason said, scowling at the pretty girl.
"Justin probably heard it from someone else, you dweeb," answered Becca. She sat down at Megan's desk and dug a little plastic bag out of her backpack. She opened it and the smell of weed filled the room. She expertly rolled it up and took a hit, a look of pleasure settling over her face. "You're not gonna tell on us for smoking this shit are you dweeb?"
Jason shook his head. He hadn't had much experience with pot since he had no one to smoke it with and he didn't know anyone that sold it. Right now he really wanted to try it though, if only to calm his nerves a little.
"Who gives a fuck about Jason and his tests, the little shit is dressing in my clothes. I think we should teach him all about being a girl, what do you girls say?" Megan stated.
"Sure, I'm down for making him look like a slut," Casey snickered. "Serves him right for being a shit to you so often."
"No, I'm not putting any makeup on. I've had enough, I'm out of here," shouted Jason. He jumped up and dashed out the doorway. The girls were hot on his heels. He could hear their pounding footsteps as they chased after him.
"Hey stop! Come back here Jason!" he heard his sister bellow.
In a straight away run he would never have a chance but Jason was hoping he could loose them in the twists and turns of the house. The front door of the house was just a head of him and he figured he had enough leeway to get away. As he reached for the doorknob he realized one thing that stopped him dead in his tracks. He was still dressed in his sister's clothes.
That one moment of hesitation was all it took for Casey and Becca to catch up. They each grabbed him by and arm and pulled him back away from the door.
"Nope, you aren't leaving until we say so. Remember, we have pictures of you in that skirt with a fuckin' woody, so you better sit down while we make you look nice and fuckable," said Megan as the two girls brought Jason back into the room.
Jason's resistance crumpled and he let Megan steer him to the vanity. He sat down and the girls surrounded him, pulling out various make-up items as they passed the joint around.
"By the way, you never answered our question, what are you doing ditching school?" Megan had a brush out and was running it through Jason's long hair.
"It's nothing, I just wanted a break that's all," Jason said, avoiding looking at the girls. He didn't want them to see the shame he felt at having been shown up by two girls or to figure out that he too wanted to see what make-up would do to his looks.
Casey had a jar of primer out and was spreading it over Jason's face. Jason never thought he would be this close to Casey much less for such a reason as this. He had lusted after Casey for years, admiring her tight, toned body every time she visited Megan and hated it when she had ridiculed him like all the others. Like most boys, however, he'd ignored that and did his best to worship the ground she walked on. His little cock was rock hard in his panties as her fingers caressed his face.
"You're lying again, I can tell. What's the real reason," Megan pulled Jason's hair back into a tight ponytail high on her head just like all the cheerleaders did. Jason had often worn his hair tied back but it was always at his neck, never high on his head. He liked the way it pulled his skin tight and made him look more girlish.
"I don't wanna talk about it," Jason said, not meeting their eyes.
"Ahh, don't be like that honey. Did you get made fun of again? Was it Cliff? Did he call you a girl?" Jason didn't answer but he blinked hard, fighting back tears. "Oh honey, I'm so sorry," Megan said, wrapping her arms around Jason and hugging him when she realized that that must have been exactly what had happened. She was feeling a little different about Jason now. He wasn't just some perv who was dressing in her clothes to get off. He was a victim now and by god he was also her brother.
"He ... he made get on my knees and ask to suck his dick! And then he got it all on videotape! I'm fucked!" he wailed. "Everyone will laugh at me at school now, I can't ever go back." He broke down into tears.
"Shhhhh," Megan said, gently stroking his back to calm him down. "It can't be that bad. Girls," she said to her friends. "This is more than just Cliff being a jerk. He is doing something wrong now and if this gets out it will ruin more than Jason. What do you think people will say about me if they see him begging to suck cock? We need to get that tape from Cliff and we need to get him back too, he has been a bully at school for far too long."
"Ya, but what can we do about it?" Becca asked. She was holding Jason's hands and applying a coat of pink polish to each nail.
"Hmm, this may be a hard one but it needs to be done," Megan paced back and forth behind Jason while Casey moved on to applying foundation to Jason's face. "Do we have anything we can use against him? Girls? Do you know any secrets we could try to exploit?" The girls shook their heads.
"No, he's the one that has secrets against me," Jason moaned in distress. Megan paced back and forth trying to think of something. The girls were almost finished with Jason and when Megan caught a glimpse of him in the mirror she broke out in a grin, as if an idea had suddenly come to her.
"That's it. We'll use the fact that we want to get that back to trap him. It might be tricky but I know we can pull it off; we have to pull it off. Quick, Becca, get Cliff's number from one of the football players, I have a plan." Becca snatched up her phone and began making calls as Casey finished applying the eye shadow and eyeliner. She brought out some mascara and brushed it onto Jason's long eyelashes.
"Alright, I got his number, what do we do now?" Becca said after she hung up the phone. Megan handed her cellphone to Jason.
"Here, you're gonna call Cliff now and tell him you want to meet him in private to get the videotape back. You need to stress that you will do anything he wants to get it, alright?"
"But Megan, I don't wanna do that, he is gonna make me suck his dick for real this time or something!" Jason complained.
"Don't worry, we won't let it get that far. The girls and I will be hiding nearby. We'll sneak up on him while you have him distracted and knock him out. We have a few toys we need to try out that I'm sure will convince him to give us back the tape." She grinned at the girls and they both giggled. "Plus, we are gonna videotape what we do to him and hold it over him for the rest of the school year."
"Oooo, this is gonna be fuuuun!" cheered Casey.
"Fuck yeah, always wanted to use those toys on some boys," giggled Becca.
"Here Jason, make the call," ordered Megan. Jason took the phone with apprehension. He dialed the number and held the phone up to his ear. The phone rang a few times and just when he though it would go to voicemail, someone answered.
"Hello?" Cliff's voice came through the speaker.
"Umm, hi Cliff, it's Jason."
"Oh hey sissy faggot; I'm just about finished putting together your coming out of the closet video. You ready to be a superstar?"
"Look Cliff, I don't want anyone to see that video. Can we meet, like in private? I'll do anything you want, anything. Even ... even suck your dick for real if you want," he said in a wavering voice.
"Anything huh? Well I guess if you're not any good I can always just post the video online anyways. Guess it's worth a shot then. You better meet me now though, right here at my place."
"Your place? But what about your parents?"
"They are gone for the weekend, don't worry about them, we'll have plenty of privacy. Come over to my house now, or else the video gets released. Oh and dress up nice and sexy and bring some booze too." There was a loud click as he hung up. Jason sat there nervously.
"Alright, I wasn't expecting him to want to meet you at his house but it won't be a problem. We should be able to sneak in there just as easily but try to unlock the back door to make it easier for us. Hurry up and finish with his make up while I get all the stuff we need together," Megan said. She removed a bag from her closet and started packing equipment into it. She dug out some cute sneakers and no-show socks for Jason to wear. Casey finished applying a coat of pink lipstick to his lips and Becca applied nail polish to the last finger. Megan found a little purse for Jason to put his phone and wallet into. The girls all dressed in dark sweats and they grabbed a case of beer from the fridge before heading out.
A moment later they were all piled into Jessica's car and heading off to Cliff's house. Megan was fiddling with the camera, making sure it worked. The girls in back were giggling to each other and Jason drove nervously, constantly looking around as if he was worried about being followed. He was afraid someone would find out what he was about to do more than he was afraid of what Cliff might do to him. There was a small part of him that was eager to find out what Cliff had in store; the part of himself that Jason had always avoided and tried to suppress.
Cliff's house was about fifteen minutes away and Jason drove the whole way in silence, only nodding every now and then to instructions Megan gave him. He parked a block away from the house and let the girls out. Megan stopped at the window.
"Jason ... how are you feeling, little bro?" she asked him, concern evident in her eyes.
"I'm nervous. I don't really know what to do in there," he admitted.
"Don't worry, just keep him distracted, make him happy, and we'll sneak up on him and knock him out," she patted his arm reassuringly. He nodded in answer, avoiding her gaze as she hurried off after the other girls.
Jason drove the car the rest of the way down the street to Cliff's house. It wasn't very big, only one story and looked to have at least three bedrooms, though he couldn't see behind it. It sat back a little from the street with high floral hedges surrounded it and hid it from the houses nearby.
Jason took all this in as he walked to the front door. He grew more confident in their plan since the privacy would keep anyone from seeing their activities. His confidence lasted until the door opened. Cliff towered over him, his chest at face level. Jason glanced up at him briefly only to see a sardonic smirk on Cliff's face, like he knew something that Jason should really, really know.
"Well well well, the little sissy sure dresses up nice. And you did your make-up! Did you do this all for me? Probably not, you probably ditched school to go play with your girly shit. Well come on it faggot, we haven't got all day. Take that beer to the fridge and bring one to me and my buddies."
Jason's heart lurched at his words. Buddies? This was supposed to be a private meeting where the girls could sneak up and overpower Cliff. Suddenly Jason wasn't so sure their plan was going to work and he wasn't at all sure that he was going to escape from this unscathed either.
Jason forced himself to strut through the door and into the kitchen. He tried to put a good act on for Cliff. It was imperative that Cliff kept his attention focused on Jason and oblivious to everything else. Jason refused to look into the living room or acknowledge the catcalls and whistles coming his way. Cliff went to sit in the living room, yelling after Jason to hurry his little ass up. The kitchen, fortunately, was down the hall from the living room, isolated and empty.
Jason glanced out the backdoor. He couldn't see the girls but he hoped desperately that they were there. He pulled four beers from the case and put the rest into the refrigerator. He carefully carried all them out to the living room where the boys were waiting.
Cliff sat in a recliner while the other two were relaxing on the couch. There was a porno on the TV, a gangbang scene featuring three guys fucking the shit out of a tiny brunette. Jason's stomach turned at the thought that they might try that with him. He felt he could handle sucking off Cliff's dick, maybe even his friend's, but just thinking about a gangbang made his asshole quiver in despair.
Jason recognized Cliff's two friends from school. Paul and Jordan, he thought. They were on the football team too and looked like carbon copies of Cliff. They were the ones that had videotaped him earlier at school.
"Jason, why don't you take a seat between Paul and Jordan and we can discuss this," Cliff said. Jason obeyed Cliff, handing out the beers and sitting on the couch between the two linebackers, who dwarfed him by a hundred pounds each. He wrapped his lips around the lip of a beer bottle and guzzled it quickly, hoping the alcohol would make this a little easier.
"I get the feeling we aren't gonna need to discuss anything, huh Cliff?" Paul said, watching Jason suck down the beer.
"Haha, you're right. He looks like a natural born cocksucker. Well, since I'm the gracious host as always, Jason, why don't you start by taking care of my two boys?" Jason didn't have to ask him what he meant by that.
He slid off the couch and knelt between the two men. They both quickly pulled down their pants to display their hardening cocks. Both were much bigger than Jason's little penis. Paul's cock was about seven inches while Jordan's looked to be almost eight. They were both thick and Jason could barely get his hands around either.
He chewed his lip nervously, not sure how he should start this. He leaned forward tentatively and stuck his tongue out to lick under the head of Paul's cock. It tasted like sweat and something else. He looked down to see a large drop of precum ooze out of the tip. Jason licked across the swollen glands, collecting the drop on his tongue and savoring his first taste of cum.
Paul groaned in appreciation and slid his hand behind Jason's head. Jason tried to resist the pressure of Paul's grip at first but Paul was insistent and he finally gave in and let Paul guide him. He stroked the shaft softly as he sank his mouth down onto it.
"That's right slut, fill that hot little mouth with hard cock. You look like you were made to do just that," Cliff sneered.
Jason groaned around the dick in his mouth. It felt hot and soft yet firm in his hand. He flicked his tongue over the head and teased the tiny hole at the top. The precum dripping out of it told him how much Paul was enjoying his mouth. He had one hand wrapped around his cock, stroking it up and down while the other fondled Jordan's hardon.
After a minute he switched to Jordan and licked his shaft from the balls to the head, coating it in saliva. He wrapped his lips around the head and let it slide deep into his throat. He swallowed and felt the head of cock slide further down his throat. Jordan moaned in delight as Jason's throat massaged his member. He continued to switch back and forth between the two boys until they were both close to cumming.
"Stop," commanded Cliff. Jason froze, Paul's dick half way into his mouth. "You both should cum on the sluts face at the same time. Make him look like the faggot slut he is."
"Oh yeah, that would be hot," Paul agreed.
The boys stood over Jason and started jerking off. With simultaneous groans they both released their loads on Jason's upturned face. He moaned, the boy's hot cum splashing all over his face, coating his lips, cheeks and little button nose. His cock stiffened, leaking precum in a sissy simulation of orgasm. He parted his lips and caught a few strands in his mouth, swallowing them all down, and stuck his tongue out to lick their cocks clean.
With a sigh he let the newly cleaned cocks fall from his lips. He used his fingers to scoop the cum coating his face into his mouth. It was still warm and only a little salty. He closed his eyes and reached down to softly run his rock hard sissy cock through his panties.
Jason opened his eyes to see Cliff holding up his cellphone.
"What a dirty little whore you make." Cliff turned the phone to show Jason. The picture captured Jason with his eyes closed in ecstasy; one hand thrust down to stroke his cock and the other scooping cum into his mouth. He certainly did look like a dirty little whore.
"I think it's my turn now," Cliff said and removed his clothes. He stood before Jason, his hairy chest, arms, and legs a stark contrast to Jason's hairless body.
"Kneel over the coffee table," Cliff ordered. Jason obeyed with a look of fear on his face. He bit his lip, knowing better than to question him. Cliff knelt behind him. He pushed Jason's skirt over his waist and pulled his panties down his smooth ass to reveal his tight pink hole. Jason moaned in surprise as a sudden cool liquid dripped down his butt crack. Cliff snickered and a moment later his finger was sliding up and down Jason's ass crack. He flinched every time Cliff touched his anus, letting out a low moan of fear.
"Let's get you loosened up slut," Cliff said as he slipped a finger into Jason's anus, coating his insides with lube. He fingered Jason's ass roughly, making him squirm and cry out. Jason gripped the coffee table, fighting back against tears brought on by the pain of his asshole being stretched so suddenly. Cliff's fingers probed deeper, brushing against Jason's prostate and he grunted, his body responding to the conflicting feelings. He was beginning to enjoy it when Cliff pulled his fingers free and positioned his rock hard cock at Jason's entrance.
"Don't tense up or it will hurt more," he instructed Jason. Jason tried to relax and push out as Cliff slid his large throbbing dick into him. He groaned in pain as his asshole stretched to accommodate Cliff's two inch girth. It felt as if a hot rod was being shoved into him. Cliff moaned in delight as Jason's ass clamped down tightly around his cock. "Oh fuck, you're so fucking tight," he grunted, gripping Jason's hips tightly as he pushed in.
"Slow down Cliff, let me get used to it, please," Jason begged, a few tears running down his face. Cliff decided to have mercy on him and held still.
"Fine, but it will cost you," he said grinning. He brought his hand down, spanking him roughly on the ass. Jason cried out, his ass stinging from the sharp blow. Cliff laughed and quickly spanked him a few more times.
"Oh Cliff, please stop, fuck me please, just fuck me!" Jason yelled, trying to stop Cliff's assault on his ass cheeks. Cliff obliged and began to piston in and out of Jason hard. He pounded his cock into Jason savagely, not caring if it hurt him anymore or not. Jason lay across the table and cried as his asshole was brutalized. But pretty soon his asshole began to numb and he could feel the cock in him pounding against his prostate. His body couldn't help but respond to the feeling. Wave after wave of pleasure washed over him. His stomach twisted into a knot and his pelvis rolled back onto Cliff's cock as his body was wracked with dry orgasms. He was crying and gripping the edge of the table, thrashing back against Cliff, trying to achieve a real orgasm.
"Look at that boys, he is fucking me back, such a little anal slut," Cliff and the guys laughed at Jason but he was past caring, all he wanted was to cum. He tried to hump the table but only managed to brush the tip against it as Cliff held his hips back. He tried to reach down to grab his cock but Cliff pinned Jason's arms behind his back, pulling on them as he brutalized Jason's butt.
"Please let me cum, Cliff," Jason screamed in frustration.
"Tell me you love my cock in your ass," he ordered Jason.
"I fucking love it, Cliff. I love your cock. I love it in my ass. I want you to cum in my tight asshole Cliff. Please, please, please, cum in me!" Jason babbled out as his body begged to orgasm.
"Very well, but you can only rub yourself as if you had a clit," Cliff said. Jason immediately reached down and grabbed the head of his cock, rubbing it with two fingers against his pelvis. He moaned as a new pleasure washed through his body.
"Oh fuck I'm gonna cum," groaned Cliff. Jason followed right behind as Cliff slammed into him, shooting jet after jet into his hot quivering asshole. Jason came with a scream, sissy cum spilling into his palm and onto the floor. He collapsed onto the table, heaving, totally exhausted from the fucking.
"Lick your hand slut," Cliff commanded. Jason submissively obeyed, bringing his cum filled palm to his mouth and licking the cum from it. Cliff grabbed Jason's hand and made him rub it all over his own face, mixing it with the cum from the other boys. He stood over Jason, grinning at his own handiwork and then spit on his face.
"Fuckin' slut," he said in disgust. Jason cowered on the ground, afraid to anger Cliff more, waiting for him to tell him what to do next.
Cliff sat back in his seat, enjoying the sight of Jason's gaping ass slowly shrink back to normal size. A small stream of jiss ran down out of it and down his leg, pooling on the carpet.
Cliff jabbed Jason in the side with his toe. "Go get us more beers, whore."
Jason groaned and stumbled to his feet. He walked gingerly to the kitchen, his tender asshole was sore from the fucking and he felt beaten and broken, humiliated by what Cliff had made him do and the fact that he had liked it so much.
He took a moment to wet some paper towels and clean himself up as best he could before grabbing four more beers from the refrigerator. There was a soft sound from the backyard and when he turned to look, he saw Megan hiding just around the corner, peering in through the backdoor. He tiptoed over to the door, glancing quickly towards the living room to make sure no one was coming his way and opened it to let her in.
"Where the fuck have you guys been! I just got fucked in there," he whispered angrily, close to tears.
"I'm so sorry Jason. We saw the other two guys there and didn't know what to do. We couldn't overpower all three of them. I ran home and got mom's sleeping pills. Here, I crushed them for you, put them in their beers and when they fall asleep we will come in."
Jason nodded in agreement, still furious that they had left him in that situation. He was furious with himself too for going along with this plan in the first place. He was even angrier that he had cum so hard from getting his asshole ravaged.
He closed the door after her and went back to the kitchen. He carefully pored the crushed pills into three of the beers, making sure to remember which one was his. After straightening his outfit, he picked them up and walked as casually as he could out to the living room.
"What the fuck took so long, slut?" Cliff asked angrily. "Did I hear the back door open?"
"Uh, yeah, I just needed to get some fresh air, that's all," Jason lied, avoiding his gaze. He set the three drugged beers on the table before the boys and sat down between Paul and Jordan again.
"Ew fuck, don't sit over here, slut," Jordan said.
"Yeah, sit on the floor like a good little sex slave," Cliff ordered. Jason obeyed, curling his feet under him and leaning against the couch at the boy's feet. "Hey, that's a good idea. We should get a collar for him. Like 'Sissy Slut' or 'Bitch' or something." Jason let his long hair fall around his face and prayed the boys would drink their beers soon so that his torment would be over. They did, guzzling them down quickly. Jason figured the drugs would take effect within the next fifteen minutes or so.
"Hey slut, take your clothes off," Cliff yelled at him. Jason hurried to obey, throwing the clothes into a pile off to the side. "Now lie on the floor here," Cliff said, pointing at the floor at his feet. He handed Jason one of the empty bottles.
"Keep your mouth busy and suck on this for a while," he commanded. Jason took the bottle and slowly slid it into his mouth. Suddenly, a sharp blow slapped across her limp cock. Jason screamed in pain and tried to turn over and crawl away but Jordan pushed him back down with his foot on Jason's chest. Jason looked up at Cliff with tear filled eyes. Cliff was holding his belt and preparing to hit him again.
"Keep sucking," he sneered and brought the belt down hard on his penis again, encouraging Jason to follow his orders. Jason continued to tongue the bottle, screaming and crying out every time Cliff landed a blow on him.
"Lift your legs up slut!" Cliff said and Jason obeyed. "Stick the bottle in your ass now." Jason froze in fear, his legs pulled up to his chest. They couldn't possible want her to do that could they?
"Hurry up slut," Cliff said again, bringing the belt down on Jason's balls this time. He screeched and quickly brought the bottle down to his ass. He pushed it slowly in, hoping that there was enough saliva for it to slid in easily. Tears ran down his face as the boys watched him fuck himself with the bottle.
"Fuck, I'm getting tired Cliff," Jordan said.
"Ya me too," Paul agreed.
"That's what happened when you fuck a cock slut like him," Cliff said and whipped Jason's cock again.
"Dude, I'm gonna go pass out," Paul said. "But I gotta take a leak first."
"Do it on him."
"What?" Paul asked.
"Fuckin' piss on his face," Cliff said. "The slut needs a bath anyways."
Paul looked at Cliff for a minute before unzipping himself and letting loose a stream of pee onto Jason's face. Jason closed his eyes and mouth, resisting the sudden urge to vomit from the stench. Jordan joined Paul in pissing on him a minute later. Jason lay there, tears leaking out of his tightly shut eyes, crying from the shame of being pissed on. He felt the lowest he ever had in his life but his dick was rock hard again.
"Haha, the slut likes being pissed on," Cliff jeered.
"Fucking disgusting," Jordan said. Paul and Jordan left the living room, going off to sleep in the rooms in the back of the house. Cliff ordered Jason to stay were he was. He left the room and returned a minute later with a pair of handcuffs that he used to bind Jason's hands behind his back. He took all his clothes and left Jason lying on the couch.
"Enjoy your nap if you can even sleep, we'll have some more fun when the boys and I return."
Jason cried to himself as Cliff left the room.
Jason was shaken awake by someone leaning over him. He woke slowly, blinking through teary eyes up at the person. It was Casey. She was reaching around him, fiddling with the handcuffs to unlock them.
"Jason, come on get up, we got the boys all tied up. Come see us punish them!" she said in excitement.
Jason got up off the couch slowly. Pins and needles shot down his arms where the blood had been cut off from being secured behind his back. He picked up his filthy, cum stained shirt and miniskirt and pulled them on awkwardly. He looked as awful as he felt, his makeup was a ruined and streaked mess down his face and his hair was in complete disarr
He followed after Casey as she hopped excitedly down hall to the one of the rooms in the back of the house. The first thing Jason saw when he entered were the three boys, each secured to a different piece of furniture.
Paul was squirming on a chair, a pained look on his face. Jason could see some tape around the seat of the chair.
"He's sitting on a dildo!" Casey said, barely able to contain her excitement. Casey's exclamation drew the attention of the other two girls, who hadn't heard them come in. Becca hurried over and gathered Jason up into a hug.
"I'm so sorry we had to leave you with these monsters," she said. "But we're gonna get them back now, I promise. And you won't ever have to fear them again," She patted Jason's back and kissed him on the cheek. Jason was grateful for her kindness.
Megan was standing behind Cliff, who was naked and bent over a desk that had been moved to the center of the room. His hands were tied to the feet of the desk on the opposite side of his body. He was faced away from Jason and the girls. Jason could clearly see his dangling cock and balls and an odd metal devise wrapped around them.
"That's a chastity devise," Becca explained. "He won't be able to cum with that on or even get hard. The three of us all have keys to the lock, which he can't get off without possibly seriously hurting himself." She giggled, obviously enjoying the thought of the torture he would be enduring.
Jordan was lying on the bed, his arms and legs spread wide, tied to each of the four posts. All three of the boys had gags in place.
"We put our panties in their mouths!" Casey cheered, jumping up and down in excitement. "I peed a little in mine. It was the all excitement, I swear." That must be why Jordan has a sick look on his face. Jason took it all in in silence. A small part of him felt bad for the boys but then his asshole twitched and he remember what they had made him do.
"Go easy on Paul and Jordan, they didn't do to much. But you can do anything you want to Cliff."
Jason climbed up on the bed and stood over Jordan. He lifted his skirt, pulled his panties aside to expose his cock and let loose a stream of piss onto Jordan's face, making sure to further soak the wadded up panties in his mouth.
"That's for what you did to me," he hissed into Jordan's ear and reached down to squeeze his nuts until Jordan screeched into his gag.
He got down off the bed and walked over to Paul. He reached down and fondled his penis. Paul looked up into Jason's eyes pleadingly, begging for mercy through the gag in his mouth.
"I know you were just following Cliff's orders too but you need to realize that you can't just blindly follow someone like that," Jason said and gave him a sympathetic smile.
He held Jordan's cock up against his stomach and slapped each of his balls in turn. Jordan screeched through the panties in his mouth and a few tears escaped his eyes to roll down his cheeks. Jason left him there, a pain in his balls and a dildo up his ass, and joined the girls behind Cliff.
"Girls, I want to have first crack at his ass if that's ok," Jason asked. The girls all grinned and nodded. Jason stepped up behind Cliff. He spread Cliff's ass cheeks and spit on his hole. It looked very tight and his cock hardened at the sight. He stroked it lightly, rubbing it up and down his butt, coating his hole with saliva.
Cliff strained at his bindings, trying to get away. He grunted and groaned, trying to talk through the gag but the girls ignored him.
Jason positioned his cock at Cliff's backdoor. He pushed in steadily and with a sudden pop, the head of his dick was inside Cliff's ass. He let out a sigh, enjoying the feeling of a hot tight hole wrapped around his dick. Cliff screamed into the gag from the pain of his virgin ass being violated but Jason ignored him and pushed harder, sliding the rest of the way in. He had no doubt that Cliff was in less pain than he had been in for his cock was only about an inch wide compared to Cliff's two inches.
Slowly he began to fuck Cliff, pulling his cock all the way out and shoving it back in hard. He built up speed, not caring if he hurt Cliff or not. He started screaming at him.
"This is for fucking me Cliff! This is for making me suck your dick! Who is the faggot now? Oh fuck I'm gonna fill your ass with cum!"
The pleasure of Cliff's tight ass was too much for him and he slammed into Cliff hard and came with a scream. He collapsed onto Cliff's back and the girls helped him onto the floor. He buried his face in his hands and cried. Becca knelt next to him and cuddled with him against the wall.
"Come on Megan, let's fuck him some more for Jason," Casey said. They had already lubed up the massive strapons they were wearing. Megan took lead and shoved her fake cock into Cliff's ass. It was big enough that it was guaranteed to rip his hole open. Cliff was balling into the panties now. His hands gripped the edge of the desk and his forehead was pressed down against the top.
The girls took turns raping him. When one took a break she would sit on the desk in front of Cliff and rub her cunt against his face. Becca and Jessica sat on the floor and watched for a while.
Soon they all grew tired and decided it was time to leave. Megan told the other to sneak out while she stayed behind to unlock the boys. Giving the girls enough time to get to the car, she knelt next to Cliff and talked to him.
"Cliff, this was all for what you did to Jason today and before. We've recorded you taking our dildos in your ass. If you ever, and I mean EVER, touch Jason again, or say a mean thing to him, we will let this video out. Also, we have the only keys to your chastity belt. From now on you will need to come to us in order to feel release. If you ever want to cum again, you will obey every order we give you, without hesitation or complaining. This is what happens when you bully people. Do you understand?"
Cliff nodded his tear stained face. Jessica stood, walked over to Jordan and unlocked one of his hands. She placed the key into it and left the room in a hurry. Jordan would be able to get himself out in a few minutes and so she hurried out of the house and to the waiting car.
The rest of the year passed without incident. Cliff stayed away from the girls and left Jason alone. After a week of avoiding them he approached Becca one day, meekly asking for a chance to cum. Becca agreed to let him out. She had him meet her at her house that afternoon. All the girls were there for his first release.
Megan tied him to the bed before releasing him. She teased him mercilessly for over an hour, running a feather up and down his hard cock, making it constantly leak precum. Each of the girls made him eat their pussy until they orgasmed before Megan finally took his cock into her hand and jacked him off, spilling his cum all over his chest and clothes. He didn't care as he nearly passed out from the pleasure. Megan secured him after cleaning him up and sent him on his way. She knew he would be back much sooner this time.
Jason's experience had changed him significantly. His darkest fantasies and secrets had been brought out into the open and made him realize that he was not meant to live as a boy. All his pretending had only brought him pain. He felt that he was meant to be a girl and cursed the fact that he had wasted so much of his life already. He loved dressing in girl's clothes, chatting with other girls, shopping for clothes, and most of all, getting fucked like a girl.
And so, though he finished out the year as Jason, he became Jessica at home. He told his parents some of what had happened. His dad was slightly disappointed that he no longer had a son but they both only wanted the best for him. They helped him by taking him to the doctors and getting him on hormone therapy. Jason was happy to know he would be developing breasts of his own soon. He knew he had to leave this town so he could reinvent himself as a woman. He decided college would be the best place to do this.