Sissy School - Chapter 2 - 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 my face.

It was the morning of August 1st, the day after I 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. 

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

I heard the front door to the house creak open and my 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!" Amy's voice said.

My confidence faltered as I saw the huge shadow approaching. Still I stood crouched and hopped like a boxer about to go into the ring.

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

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

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

"Y-yes!" I said, standing there in just my filthy cum-crusted tighty-whities. My voice sounded small, not nearly as intimidating as I would have liked.

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

"Like hell I am!" I squealed, and I swung my right arm as hard as I could, connecting with the man's jaw.

It felt like I hit a brick of hard steel. It sounded like a slap rather than a closed-fist punch, and it made my 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 my left arm, then, with a small smirk, he tilted his head back, and roared with laughter.

The other's joined in apprehensively, still unsure what was going on.

Finally the man stopped laughing, tilted his head back down at me, 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 my wrist and spun me around painfully and pushed me up against the wall.

I tried to wriggle and scream, but he was incredibly strong and held me firm as if I were just a wiggling puppy.

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

He turned me around so that I was facing everyone with my back against the wall.  Sherry, Tom, and Amy all took one look at me and erupted in laughter.

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

Sherry was in tears, Amy pulled out her phone and was snapping pictures, even Tom (who I was no looking at 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 sense. They were going to put me in diapers!

The reality of the situation all started crashing down on me. I was being taken to this crazy mythical school, and now there was nothing I could do about it. I slid to the floor and sat in my soaked undies, then hung my head and started 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 as she glanced at me.

"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!" again she winked at me.

"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 said, glancing at me, though even I could tell she was only saying it to make me jealous. She had showed 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 barked, 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 roar.

"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, glancing at you.

"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 me. Call me crazy, but I could swear there was still a hint of love for me in her eyes.

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

Please Sherry, save me from this. I 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!"

My stomach dropped. Amy clapped excitedly. Tyrone smiled, then walked over to me and grabbed me by the hair.

I tried pitifully to get away from him, but he easily drug me like a rag doll over to the couch, my knees dragging along the carpet. 

He sat down on the couch and bent me over so that my knees were still on the floor, and my 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 was pointing to the are on the floor behind me.

"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 me.

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

Despite the horror of my situation, I still had to glance around to see what Tom was working with. For some reason I had to know if he was bigger than me. Unfortunately (?) it was hard to tell, as his 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, we never kissed in public, and we surely didn't do anything remotely sexual in front of other people, back when we were actually doing stuff, that is. But without hesitation (perhaps because she knew I was watching) Sherry crossed the room, got down on her knees, and immediately started sucking Tom's cock.  Amy just looked away...

"Look at your wife you little bitch!" Tyrone said, grabbing me by the hair again and forcing my 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 me, 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 me. She made sure this was the best blowjob she'd ever given, and that I 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 mine. Maybe 5 or 6 inches. Average. Nothing special. Nothing to write home about. That small tidbit made me feel a little better, until I 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 me and grabbing the waistband of my 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 my ass was exposed.

I guess the cool air hitting my bare bottom reminded me of what was about to come. Because this was when I started going into panic overdrive.

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

The begging had the opposite effect of what I intended though, as I glanced back I 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 me.  I heard her spit onto my back around my tailbone, then felt it run down the crack of my ass to my hole.

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

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

I felt so exposed, I felt so helpless as I struggled against the cuffs and Tyrone's grasp. "Honey PLEASE!" I 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 to my poor, virgin asshole.

I felt it poking lightly against me, like a blind snake looking for somewhere to burrow. Then slowly I felt it press harder as Sherry pushed Tom in. All i felt was the tip of his head enter me, spreading me open. He pushed harder, but hole wasn't having it, trying to ward off the unfriendly invader. Again he pressed in painfully, and again my 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!" I felt Sherry withdraw the cock and heard her spit again. Then jam the wetter head of the cock into my ass. This time at least 3 inches of it entered, and I squealed like a pig.

"Nooo!! Noo! NOOO!!" I screamed. Tyrone held me firm, but still I screamed. "NOO!! NOO!! NOOO-mmppHHH!"

My screams were cut short as Amy snatched up my piss-soaked underwear and shoved them in my 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 I 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. My sphincter had finally relaxed and allowed Tom all the way in, but that didn't make it feel any better. He definitely didn't feel 'average' sized. It felt like his dick was filling all of my insides.  I couldn't help but bite down into the piss soaked undies in my mouth each time he pulled back and pushed it back in. The taste in my 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 pleasureful part of him had taken over. He started getting a rhythm as he fucked me now. In and out, in and out, left, right, side to side. It was like he was playing a pinball game with my insides, and all I could do was just lay there and take it.

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

I turned my head and tried to will this all to be over. From what I 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 my bare ass as he pounded me.

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

Both Tyrone and Amy were furious! Amy started smacking my face as she stuffed the undies back in, and Tyrone's grip on my 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 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, and Amy hastened to obey, running up the stairs faster than i'd ever seen.

Tom continued to fuck me 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 me by the head and flipped me over onto my back. His giant fingers peeling around my head and into my 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 my helplessly pried open mouth. Tyrone held me steady as I helplessly tried to wiggle away. Then 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 my mouth.

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

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

"OWWW!!" Tyrone roared, pulling his hands from my mouth and pushing my head as I choked and spit out the load in my mouth.

"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 me by the hair, he jerked my head back and forced the ring inside my mouth, keeping me from being able to close my lips. Then he wrapped the belt around my 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 me 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 my 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 I had a big load of snot in my mouth. Amy immediately clapped her hand over my mouth and pinched my nose.

"Swallow it, Bitch!" She ordered.

I don't know if you've ever tried to swallow something without closing your mouth, but it's not easy. Believe me, I wanted to swallow it, I wanted the taste to go away.  But it was not easy. I choked and sputtered as I used every muscle in my mouth I could 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 my mouth. Even emptying 3 at once to "see how much they could fit in there" before making me 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 my legs in the air and held them tight while I lay back against the couch, exhausted. Tom apparently was eager to get back in, being blue balled before, he spat on his dick and reentered me easily. I already felt like a whore. 

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

Tyrone just laughed 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 my mouth, allowing my jaw to relax and the ends of the condoms to flop out, which Sherry happily stuffed back in. I was given very little respite before I saw the ball of the gag cross my eyes and stop in front of my mouth. 

"Pleasshh no..." I pleaded, that was the last thing i said before the ball was pulled into my mouth and the strap around my head was tightened, trapping the used condoms within. 

It was a disgusting mixture inside my mouth. Dick sweat and dick juice with a latex casing, all being churned and sloshed with every thrust from Tom between my legs. 

Each breath brought one of the condoms to the back of my throat, and i was constantly in fear that i would die from choking on someone else's used condom. I did my best to only breathe through my nose. 

"Jesus Tom, hurry up and cum already." Amy barked, still holding one of my legs in the air. It was the first time Amy said something i could get behind. I just wanted this to all be over.  

Sherry smiled, holding my other leg, and leaned over to whisper something in Tom's ear. 

I don't know what she said, but whatever it was it got Tom's attention. I could feel his cock getting harder in my ass as his pace increased. It felt like the head of his cock was inflating like a balloon. 

As it did, it started pressing against something inside of me. I don't know what it was, but suddenly a pressure was building in me. 

Tom was thrusting as hard and fast as he could now, and to my surprise, it actually didn't feel as bad as it did before. For the first time since this ordeal started, i paid attention to my own dick. It was still flaccid and tiny as ever, but it started leaking precum!

As Tom continued to pound me, the pressure inside me intensified. His cock felt huge inside me now, rubbing against that weird spot even more. I felt his dick pulse, followed by a slightly warm feeling in my insides as he started cumming. he pounded even harder as he came. My eyes rolled back in my head, something inside me was pulsing, and before i knew it, MY dick started shooting cum all over my chest, without me or anyone else touching it! And of course, this was all in full view of everyone. 

"Oh my god!" Amy squealed. "Did he just...cum?!"

Sherry just looked on in utter disbelief. "I...didn't think that was possible!" she said. Then they both erupted with laughter. 

"Yes it's possible," Tyrone said, rubbing my sweaty, matted hair as one would a pet "and if he trains properly, he can learn to harness it!"

"So..." Sherry asked me as Tom withdrew his now slimy cock from ass, "Did you enjoy your first time?!"

"I'd say he did!" said Amy, referring to the pool of cum on my stomach. Again they laughed. 

I wanted to curl into a ball and die. Any shred if horniness within me was gone. 

As I tried to turn away Tyrone grabbed my head, bringing my hair back. I saw his eyes land on the dickshaped birthmark on my head, and for the first time, his expression changed from that of boredom to pure surprise. 

"Is that? Is that?! A dick on your forehead?!" he exclaimed. I paid no attention, thinking it was just another person to make fun of my unfortunate birth defect. "Y-you're the chosen one!"

And everyone laughed. 

"Please..." Amy scoffed "Dickhead? Chosen for what? To be the one with a tiny dick? Or a tiny dick that spurts when he gets fucked in the ass?! Hahaha!!" Again everyone laughed, except Tyrone. His expression was serious. 

"You don't understand. We've been looking for him for EVER! And I'M the one who found him!" he sounded like a giddy kid on Christmas morning. When he looked around and saw everyone's befuddled looks, he explained "Legend has it, that the man born with this mark will hold the power to make any other man cum within 7 seconds!"

"Well obviously that's not true..." said Sherry, referring to how long it took Tom to cum in my ass. 

"Maybe not yet! But he will be!" said Tyrone, jumping off the couch and fiddling with his belt buckle. 

"What are you doing?" Tom asked, speaking up for the first time, he looked like he was worried Tyrone was about to take HIS ass.

"I'm going to fuck the Chosen One! You're not gonna be the only one who gets to say that! Oh i KNEW i should have fucked him first! Imagine if i could say I was the one who took his virginity!" Tyrone dropped his pants, exposing his huge dong. It had to be at least 8 inches,  and it was still flaccid!

Amy jumped up and ran over to him like a hungry school girl. "Do you need...help?" she asked, biting her bottom lip as she ran a finger down his chiseled abs. 

Tyrone smacked her hand away, "Sorry honey, not interested. I'm gay!" Then he closed his eyes and squinted hard. As if by magic, his cock started poking up and was fully erect in seconds. 

And with that he knelt down in front of me, raising me up like a rag doll. I was too tired to protest, even though his massive python scared the ever living out of me. 

He pressed the huge head of his cock to my hole, Tom's cum slowly leaking out. He used that as lube to force his giant member inside of me. I felt like i was getting torn in half from the inside as he slowly forced as much of his 12 inches in me as he could. They all watched (Amy crossing her arms in jealousy) as he used me. 

It was an extremely taxing day, and it wasn't even noon yet. There was still much MUCH more to come...

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End of Chapter 2. If you enjoyed this Chapter, head on over to find out what happens to Larry in Chapter 3 "Guyagon Alley"!