Sissy School Ch. 02 - The Bouncer

BOOOOOM!!! BOOOOOMM!! BOOOOOOOOOOOOMMM!!!

There were 3 huge knocks on the door. So loud and hard it knocked dust off the underside of the staircase onto Larry's face.

It was the morning of August 1st, the day after he was supposed to report to Sissy School.

"THIS IS TYRONE FROM THE SISSY SCHOOL FOR MALE-WHORES AND ADULTERERS!" Said a loud, booming voice through the door. "I AM HERE TO COLLECT A LARRY PARKER..."

There was a flurry down the steps as Sherry came running down. Shortly followed by a slower Amy and an even slower Tom.

Larry stood up in his cupboard too. Well, as much as he could without hitting his head on the steps above. Whoever this was, he was prepared to fight.

He heard the front door to the house creak open and his wife Sherry's voice say "Hello! Please come in!"

Huge pounding steps, it sounded like a giant was entering the house.

"He's right over there!" Amy's voice said.

Larry's confidence faltered as he saw the huge shadow approaching. Still, he stood crouched and bouncing like a boxer about to go into the ring.

Larry heard the lock on the cupboard rattle as the key was inserted and turned for the first time in a week (the last time his chamber pot was emptied). He heard the lock come off and the mechanism slide.

He clenched his fists and prepared for what was next. The door opened and the light stung his eyes as the two connected for the first time in ages. He couldn't see a thing, until a huge gargantuan shadow came in to eclipse it.

"ARE YOU LARRY PARKER?!" The man roared, looking down at him. His wife, her lover, and her daughter gathered around behind, all smirking.

"Y-yes!" He said, pitifully, standing there in just his filthy cum-crusted tighty-whities. His voice sounded small, not nearly as intimidating as he would have liked.

"You're coming with me," he said, grabbing him by the left arm.

"Like hell I am!" he squealed, swinging his right arm as hard as he could, connecting with the man's jaw.

It felt like he hit a brick of hard steel. It sounded like a slap rather than a closed-fist punch, and it made Larry's hand erupt in pain as every bone inside felt like it shattered.

The spectators gaped in shock, waiting for what would happen next.

The man just stood there, stoic, still holding Larry's left arm. Then, with a small smirk, he tilted his head back, and roared with laughter.

The others joined in apprehensively, still unsure what was going on.

Finally the man stopped laughing, tilted his head back down, and narrowed his eyes.

"Do you know how many pathetic little beta-boys like you I round up a day?!" he said coldly. Then, in one fluid motion, he twisted Larry's wrist and spun him around painfully, pushing him up against the wall.

He tried to wriggle and scream, but the bouncer was incredibly strong and held Larry firm as if he were just a wiggling puppy.

Larry heard the clinking of handcuffs, but felt fuzzy things wrapped around his wrists. They were just like the fuzzy cuffs you would buy at a kink store, except much more durable.

He turned Larry around so that he was facing everyone with his back against the wall. Sherry, Tom, and Amy all took one look at him and erupted in laughter.

Larry assumed it was because of the ridiculous pink fuzzy cuffs he was locked in. But he realized they couldn't really see those. Instead, he looked down and noticed that the tighty-whities he was wearing were now soaked with piss.

Sherry was in tears, Amy pulled out her phone and was snapping pictures, even Tom (who Larry was now seeing face-to-face for the first time) couldn't help but chuckle.

"Don't worry" Tyrone, the giant black man, said. "They have something just for that at The School"

Suddenly the line in the letter stating "At least 500 Diapers" for required materials made more sense. They were going to put him in diapers!

The reality of the situation started crashing down on him. He was being taken to this crazy, mythical school, and now there was nothing he could do about it. He slid to the floor and sat in his soaked undies, hanging his head and starting to weep.

The trio laughed, but Tyrone wasn't amused, apparently he had seen all of this before. He pulled out a clipboard.

"So before I take him there are a few questions I'll need you to answer, Mrs. Parker..."

Sherry wiped the tears of laughter from her eyes, cleared her throat, and poked up. Her eyes sweeping Tyrone's chiseled build.

"Is this man currently still legally your husband?" Tyrone asked.

"Yes...legally..." she scoffed.

"And do you hereby relinquish all of his rights to the Sissy School of Man-Whores and Adultery?"

"Yes. Yes I do." She said, smiling triumphantly, glancing at Larry.

"You understand that your husband will be subjected to severe corporal punishment, to regression therapy, to hormone therapy, and you will most likely not be able to recognize him by the time he returns next Summer?"

"Oh...I'm counting on it!" she winked again.

"Okay...then just a few more questions. Has your husband ever partaken in anal sex? Specifically: has he ever taken any sort of object in his rectum?" Tyrone asked.

"Not that I know of..." Sherry replied.

"But I wouldn't doubt it!" Amy chimed in, giggling at her own joke.

"So your husband is essentially an anal virgin?" Tyrone asked, surprised.

"Yes...you could say that."

"And are you with this man now?" Tyrone asked, pointing to Tom. Even Tom started trembling when referred to.

"Yes. Happily!" Sherry added, eyeing Larry, though even he could tell she was only saying it to make him jealous. She had shown much more interest in Tyrone in the last few minutes than she had ever shown Tom in their entire relationship.

"And you mean to tell me that the two of you are essentially cuckolding this man, but never had him partake in any sexual acts in the bedroom with the two of you??" Tyrone roared, seeming somewhat offended.

"I just...never wanted to fuck Larry again after what he did to me!" Sherry said, taken aback at having to defend herself.

"You don't have to fuck him. He can be used for fluffing, receiving, for CLEAN-UP!" Tyrone started to yell.

"I-i'm sorry...I guess I just...never thought about it..." Sherry said, no longer chuckling the way she was before.

Tyrone sighed, perhaps realizing he had gone too far.

"In that case, would you like to witness your husband's deflowering? Or are you comfortable with not observing that particular point in his transition?"

"You...you want me to watch him get his ass fucked?" Sherry asked, watching Larry tremble.

"I'm asking if you'd like to see it." Tyrone replied, smiling.

Sherry genuinely seemed to contemplate it for a second, then looked at her husband. Larry could swear there was still a hint of love there in her eyes.

"You know, I was really hurt when I found out about him and that slut..." she rubbed her chin.

Please Sherry, save me from this. Larry tried to tell her telepathically.

"..and..." a wicked smile suddenly crossed her face "I want him to feel that pain. I want him to cheat on me again, but this time, I want him to take it, and I want to watch!"

Larry's stomach dropped. Amy clapped excitedly. Tyrone smiled, then walked over to Larry, grabbing him roughly by the hair.

He tried futile to get away, but he was easily dragged like a rag doll over to the couch, knees dragging along the carpet.

Tyrone sat down on the couch and bent Larry over so that his knees were still on the floor, and his face was in his lap.

"You...Tom is it? Come here!" Tyrone ordered.

Tom didn't know what to do, just stood there. "M-me?" he asked, unsure.

"Yes, you. Come here, you're going to be the one to do it." Tyrone said, pointing to the area on the floor behind Larry.

"B-but I...I'm not gay...and I don't...want any part of this." Tom mumbled.

"YOU WILL FUCK THIS SISSY'S ASS OR YOU WILL COME WITH HIM TO THE SCHOOL AND GET YOUR ASS FUCKED REPEATEDLY FOR THE REST OF YOUR GOD DAMN LIFE!" Tyrone yelled. "NOW GET OVER HERE AND PULL YOUR FUCKING PANTS DOWN!"

Tom hastened to obey the big black man. Walking across the room until he was directly behind Larry.

"I said DROP THEM!" Tyrone yelled again, and Tom started unbuckling his pants.

Despite the horror of Larry's situation, he still found himself glancing around to see what Tom was working with. For some reason, he had to know if Tom was bigger than him. But it was hard to tell, because Tom's cock was limper than a noodle.

"Sherry" Tyrone said, his voice changing to a softer tone "Would you be so kind as to get your lover hard so that he can fuck your husband's ass?"

Sherry had always been weird about PDA, her and Larry never kissed in public, and they surely didn't do anything remotely sexual in front of other people, back when they were actually doing stuff, that is. But without hesitation (perhaps because she knew Larry was watching) Sherry crossed the room, got down on her knees, and immediately started sucking Tom's cock. Amy just rolled her eyes and looked away...

"Look at your wife, you little bitch!" Tyrone said, grabbing Larry by the hair again and forcing his head around to watch. "Watch her suck a dick, you're gonna learn to do that REAL soon!"

It was painful to watch, even after all this time of hearing them fuck in the room above him, there was nothing quite like seeing your own wife take another man's dick in her mouth. She even moaned and slurped and stroked it while she did it. She never did that for Larry. She made sure this was the best blowjob she'd ever given, and that Larry had full view of it.

"Alright, I think that's enough, '' Tyrone said, and Sherry removed Tom's cock from her mouth with a 'Shhlloppp'.

Tom's cock was fully erect now. But it wasn't much bigger than Larry's. Maybe 5 or 6 inches. Average. Nothing special. Nothing to write home about. That small tidbit made him feel a little better, until he remembered what was about to happen.

"Someone pull down his pissy panties" Tyrone barked.

Sherry looked at Amy.

"Me?!" Amy asked, shocked. "I'm not touching those..."

"You handle the chamber pot..." Sherry retorted.

"Yea cause YOU make me!"

"ENOUGH!" Tyrone roared. "You! Young lady! This is your step-father correct?" He asked Amy. She nodded. "And you want to see him get buttfucked too right?" Again she nodded, smirking this time. "Then pull down his undies so he can take it!"

Amy obeyed, hesitantly kneeling next to Larry and grabbing the waistband of his undies with the very tips of her fingers, making sure to touch as little of the soaked mess as possible. she delicately pulled them down so that his ass was exposed.

The cool air hitting Larry's bare bottom must have reminded him of what was about to come. Because his panic started going into overdrive.

"No! Please! NO! Honey! Please! Stop this! PLEASE! DON'T LET THEM DO THIS!" Larry pleaded as he squirmed, but Tyrone held him firm.

The begging had the opposite effect of what he intended, though. When he glanced back, he saw her smile widen into a wicked grin. Then, without even waiting for Tyrone's command, she grabbed Tom by the cock and led him down on his knees behind Larry. He heard her spit onto his back around his tailbone, then felt it run down the crack of his ass to his hole.

"Amy spread his cheeks for me" It was Sherry doing the commanding now, taking charge of the situation.

Amy obliged, getting next to him, grabbing both of his ass cheeks, and spreading them wide.

Larry felt so exposed, so helpless as he struggled against the cuffs and Tyrone's grasp. "Honey PLEASE!" He cried into Tyrone's crotch, feeling his giant member stiffening under his shorts.

"Do it for me, baby" Sherry whispered to Tom as she aimed the head of his cock at Larry's poor, virgin asshole.

Larry felt it poking lightly against him, like a blind snake looking for somewhere to burrow. Then slowly he felt it press harder as Sherry pushed Tom in. All Larry felt was the tip of his head enter, spreading him open. Tom pushed harder, but Larry's hole wasn't having it, trying to ward off the unfriendly invader. Again he pressed in painfully, and again his hole pushed back.

"Do you need lube?" Tyrone asked.

"Nope..." Sherry replied immediately, "I want this one to be special for him! I want him to take it raw!" Larry felt Sherry withdraw the cock and heard her spit again. Then jam the wetter head of the cock into his ass. This time at least 3 inches of it entered, and Larry squealed like a pig.

"Nooo!! Noo! NOOO!!" He screamed. Tyrone held him firm, but still Larry screamed. "NOO!! NOO!! NOOO-mmppHHH!"

His screams were cut short as Amy snatched up the piss-soaked underwear and shoved them in Larry's mouth. Smiling the most evil of smiles as she did it. "How's that 'Daddy'? Enjoying losing your virginity?! Is it every bit as special as you'd hoped?!"

Amy always was a cunt, and Larry told her that right then, but all that came out were muffled sounds of "hrhmff fmgrr mgoarh cfugnt!" She just laughed like the wicked little witch she is.

It was not special though, it was especially painful taking a dick in the ass. Larry's sphincter had finally relaxed and allowed Tom all the way in, but that didn't make it feel any better. Tom definitely didn't feel 'average' sized. It felt like his dick was filling all of Larry's insides. He couldn't help but bite down into the piss soaked undies in his mouth each time Tom pulled back and pushed it back in. The taste in Larry's mouth was foul, even before the piss, 2 months of the same sweaty, cum-soaked underwear would make anyone gag.

Tom took over now, Sherry no longer guiding him in and out, the pleasurable part of him had taken over. He started getting a rhythm as he fucked him now. In and out, in and out, left, right, side to side. It was like he was playing a pinball game with Larry's insides, and all Larry could do was just lay there and take it.

Amy took out her phone and started videoing and snapping pics. Larry had no doubt that this would soon end up all over the internet and in all of her friends' (and maybe even his friends') inboxes.

Larry turned his head and tried to will this all to be over. From what he had heard of Tom and Sherry's sex life, Tom didn't last very long. But it was already feeling like it was taking hours.

"Harder!" Sherry cheered! "Harder!!"

Both the girls were clapping their hands as Tom's pelvis clapped against Larry's bare ass from pounding him.

Larry was out of breath, having underwear in your mouth doesn't exactly keep you from getting winded, and he must have wrung all the piss out of them because his mouth felt dry. He spit the undies out and gasped for air -- bad decision.

Both Tyrone and Amy were furious! Amy started smacking Larry's face as she stuffed the undies back in, and Tyrone's grip on his handcuffed arms tightened.

"I think the sissy is getting thirsty...do you have any used condoms around the house?" Tyrone asked.

Amy got that wicked smile. "I have some of my boyfriend's in the trash!" she squealed like a proud student who knew the answer in class.

"And there are some more of Tom's on the floor in our bedroom" Sherry chimed in.

"Go get them, and bring me the bag I came in with" Tyrone ordered. Amy hastened to obey, running up the stairs faster than Larry had ever seen.

Tom continued to fuck him until Amy returned with a handful of used rubbers, and Tyrone's giant black duffel bag.

Amy went to hand the condoms to Tyrone, but he waved his hand dismissively, "No no...you do the honors..." and with that, Tyrone grabbed Larry by the head, flipping him over onto his back. His giant fingers poking around Larry's head and into his mouth, prying it open.

"Empty them...one at a time, into his mouth. A sissy should know what cum tastes like before he gets to School" He commanded. Both Sherry and Amy gathered on either side, giggling like little girls.

There must have been at least 10 condoms in Amy's hands, all bulging at the bottom like little balloons with large, white loads inside.

She handed one to Sherry. "Open wide hubby!!" she said "It's time for you to learn why I never wanted to swallow!"

She turned the condom upside down so that it dangled right above Larry's helplessly pried open mouth. Tyrone held him steady as he helplessly tried to wiggle away. Sherry grabbed the tip of the condom with two fingers, and slid them down, pushing all of the cum and dick juice out so that it poured into her husband's mouth.

Larry immediately gagged as soon as the first drop hit his tongue. He didn't know if it was Tom's or Amy's boyfriend's cum, but it was salty, tangy, and disgusting.

He choked as the thick, creamy liquid migrated to the back of his throat. Biting down instinctively, and pinching Tyrone's fingers in the process.

"ARGGHH!!" Tyrone roared, pulling his hands from Larry's mouth and pushing his head as he choked and spit out the load.

"I knew that sissy would bite! I should have just gagged him from the start! Get me my bag!" Amy pushed the bag closer to him, even she looked frightened.

Tyrone unzipped his bag and dug inside until he found what he was looking for. He pulled out what looked like a belt with a little ring in between. Yanking Larry by the hair, he jerked his head back and forced the ring inside his mouth, keeping him from being able to close his lips. Tyrone wrapped the belt around Larry's head and cinched it tightly.

"There...let's see the little bitch bite now!" Tyrone barked. "As you were ladies..."

The girls circled back around Larry again, their smiles returning. It was Amy's turn now "This time you're gonna swallow it like a little slut!" She yelled, turning another condom upside down and emptying it into the little O-ring in his mouth.

This one was worse than before. It had a really funny taste to it, and was even more thick and bitter. It felt like he had a big load of snot in his mouth. Amy immediately clapped her hand over Larry's mouth and pinched my nose.

"Swallow it, Bitch!" She ordered.

If you've ever tried to swallow something without closing your mouth, you know it's not easy. Larry wanted to swallow it, he wanted the taste to go away. But it was difficult. He choked and sputtered and used every muscle in his mouth to get it down. After about a minute, Amy finally released her hand and checked inside. When she saw there was no cum left, she smiled.

They took turns emptying the condoms into Larry's mouth. Even emptying 3 at once to "see how much they could fit in there" before making him choke it all down. Tyrone just laughed while Tom watched in horror.

The girls, noticing Tom just sitting there, invited him back over.

"Oh sorry Tom! We've been having all the fun!" Sherry said. "Want to get back in there?"

The girls grabbed Larry's legs in the air and held them tight while he layed back against the couch, exhausted. Tom apparently was eager to get back in, being blue balled before, he spat on his dick and reentered him easily. Larry already felt like a whore.

The girls apparently grew bored of dumping loads in his mouth, so instead they just stuffed the three remaining used condoms entirely inside. The latex sticking to the insides of his mouth like gum.

Tyrone smiled at the way the girls took charge. "Get me the ball gag" he chuckled.

Amy must have known exactly what that was because she didn't ask and it took her very little time to find it in the duffle bag. She brought it to Tyrone, happy as a puppy bringing back a fetched ball.

Tyrone removed the ring gag from Larry's mouth, allowing his jaw to relax and the ends of the condoms to flop out, which Sherry happily stuffed back in. He was given very little respite before he saw the ball of the gag cross his eyes and stop in front of his mouth.