Peekaboo Boi! By Brian Masters (63 pages) (Patreon)

Peekaboo Boi!

By Brian Masters

(Concept by Devin Dickie)

© 2019-2021 QoS Comix All Rights Reserved

No part of this publication may be reproduced, distributed or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law. For permission requests, email to ​Devinwhitegurl@gmail.com 

This is a work of fiction. Names, characters, places, and incidents are a product of the author’s imagination. Locales and public names are sometimes used for atmospheric purposes. Any resemblance to actual people, living or dead, or to businesses, companies, events, institutions, or locales is completely coincidental.

***DEVIN DICKIE NOTE***

All characters are OVER 18 years of AGE! This is a bullying fantasy and not real.  The acts in the following written work are only consensual  sexual choices and fantasy humiliation scenarios.

Bullying is NOT OKAY and If you or someone you know is being bullied, please alert the authorities. 

****SPOILER ALERT!! for upcoming comic... if you don't want to know what is happening with this comic, PLEASE DON'T READ!

SPOILER ALERT!!

Peekaboo Boi!

By Brian Masters

Conceptualized by Devin Dickie

Part One

Sept 1st 

Hey Journal it’s me Kenny Stubbs again. Well no kidding huh? I mean who else would it be? I know it’s been a while since I wrote anything new but, Holy Cow! It’s the first day of school for my senior year, I’m 18 at last, and I’ve finally worked up the nerve to do it! I’m going to wear a pair of panties under my uniform! Isn’t that crazy? Just think what old Principal Wood might say if he knew one of his students was defiling his school uniform in such a way. There would be a scandal of epic proportions if anyone at BBC Preparatory Academy were to be found crossdressing in even such a minor way. Think of all the senators, astronauts, ambassadors, and presidents who went to this stuck up school before me and what they would think of the way I’m disrespecting their alma mater. This is going to be incredible! I have to sneak around a bit this morning so I’ll catch you up later Journal. Bye for now.

Sept 1st, Later that night

Well it was certainly a weird day journal. To start with I snuck a pair of my step mom’s panties from the clothes hamper and took them into my room before breakfast. I’ll admit I couldn’t help but take a few quick sniffs just to set the mood. After all you and I both know it wasn’t the first time I’ve ‘played’ with a pair of the Stepmonster’s underwear and after today it definitely won’t be the last. I chose the most feminine pair I could get and boy was I lucky. There was a pair of pink, satin, bikini cut panties rolled up in the leg of her yoga pants and they were still damp from her morning workout. The smell was amazing! That mixture of sweat, pussy juice, and swamp ass made my head spin. I almost came just from the feeling of sliding them up my legs and pulling them tight against my crotch. The silky material felt amazing against my skin and the cool dampness from my step mom’s bodily fluids against my balls felt like being kissed by an angel. 

I had to stand very still for almost five full minutes to get myself under control again and make sure my dick went soft so I didn’t have an accident. I know I don’t have a very big dick but in those panties I have a difficult time staying soft and an almost impossible time not shooting my load. I have no illusions of being any kind of stud as you know, journal, but I still have needs that are hard to suppress. 

I know I haven’t written in a while so maybe I need to fill you in on how I’ve filled out. I’m not fat, let’s get that out of the way right now. I’m heavy. I can’t seem to shake this, well step momma calls it baby fat. I tend to jiggle when I walk and it’s pretty embarrassing. My butt got big and round. The Stepmonster says I have a real booty back there and I could twerk like a pop star if I wanted to. I guess that’s not too bad but I also have a pair of rather noticeable “man boobs”. Oh man it’s so humiliating seeing how they bounce around if I try to run or jump or play any kind of sports. That’s why I don’t take gym class. I stole a notepad from my doctor’s office and forged a note. Pretty clever right?

Anyway, the boobs and the puffy nipples that cap them are the reason I hate to take off my shirt in front of anyone. On top of all that I still have to contend with the freckles that never went away and the curly red hair. I look like a chubby Raggy Andrew doll! Oh and here’s something I never knew about gingers, we don’t have a lot of body hair. I mean when I look down in the shower I might as well be a chick! No chest hair, no armpit hair, no leg or arm hair, just a small tuft of bright red, curlies above my too small pecker. 

And while I’m on a roll let’s talk about that! You would think with all the other things I have going on with my body at least I’d get a big dick right? Wrong! When it’s soft you can barely see the damn thing and when it’s hard it only measures four inches. I mean four fucking inches? What the fuck?

Ok Journal I’m sorry. I’m digressing from the original point. Let’s get back on track. When I finally calmed down enough to get dressed I was in heaven knowing the dirty secret I was hiding. I had on a pair of damp, smelly, stained, pink panties just like a slutty little sissy from those nasty interracial stories, cartoons, and videos I’ve been getting into. It felt wonderful.

I skipped out on breakfast and practically ran to school. The faster I moved the more I could feel that wet, silky material rubbing against my marble sized balls. It was divine! When I got to school I took my time walking through the crowded halls smiling to myself, happy in the knowledge of the naughty game I was playing. 

Then I saw her. Jennifer Dillon, the most beautiful girl in school was walking toward me with her entourage following close behind. Cheerleaders, like beautiful birds, flock together in the wild and they are a beauty to behold. But just as the group was passing me that bastard Rick Jefferson tripped me and I barely caught myself before falling on my face. I landed on my knees and as I was getting back up I felt my shirt become untucked by just an inch or so. I moved quickly to pull it back into place and I’m certain no one saw anything but just as I looked back at Jennifer I thought I saw a knowing smirk cross her perfect face. 

Did she see the panties? Was she just amused by what that stupid jock had done to me? Or, could she possibly have been smiling AT me? Oh god please let that be it! Maybe she likes me. Oh Journal could it be? More tomorrow my faithful companion.

Sept 2nd

Ok, this didn’t go the way I’d hoped. I’m sitting here in the last stall in the boy’s toilet writing to let you know what happened Journal old friend. Jennifer was not smiling at me, she was smiling because of me. That became obvious when a group of her friends started following me around after homeroom laughing and pointing. I’m used to the abuse from the cool kids but this was different, like they knew some secret about me that they couldn’t wait to exploit. Maybe I’m just being paranoid but it seems like the jocks are taking an interest in me and that’s never a good thing. I’ve caught several of them pointing at me and smirking then turning away like they don’t want me to see them. I’m getting really nervous, Journal. I just want to get through this day and have a good wank in front of my laptop. The only thing making me feel comfortable today is the pair of panties I’m wearing. It’s strange how comfortable they make me feel, how sedate and relaxed. Today I got lucky again and found a good ripe pair in the laundry. These are more of a bikini cut so they’re a lot tighter and are giving me a wedgie but man do they smell great! So sweaty and funky with B.O. and swamp ass and definitely a little bit of piss mixed in. I’m getting hard just sitting here since I can smell them even though they’re pulled down to my knees. Oh shit! There’s the bell, gotta go, more later.

Sept 2nd, Lunchtime

Oh no, oh no, oh no! This is bad Journal, really bad. I got called into the principal’s office after 4th period to find out someone told him I faked the note to get me out of gym class. He said a group of “concerned students” came to him and told him they were suspicious of my excuse since I seem to be quite capable and not at all hindered by any health issues. They said it wasn’t fair to those people with real health concerns if someone was faking and taking advantage of the school’s good graces. He pulled the note from my file and compared it to one of my homework assignments right there in front of me. I almost pissed my pants, I was so scared. I thought for sure he would suspend me or expel me and now that it’s over I wish he had because what he’s done to me is far worse. He’s making me attend gym class. Not tomorrow or next week but today, as in next period. Oh fuck, what am I going to do? And here’s the worst part, I know who it was that narced on me. It was Jennifer and her band of lowlife friends with Rick Jefferson leading the charge. They were all waiting outside Principal Wood’s office when I came out and were giggling in a huddle while watching me walk away. I’m terrified!

Sept 2nd, Later that evening

Oh Journal it was so much worse than I ever expected. I honestly thought I could get away with not changing clothes or at least not taking a shower but the coach told me I had to participate in every Phys Ed activity. I waited till everyone had left the locker room before changing into my gym clothes and I actually thought I could do the same after class. Oh fuck was I ever wrong. We played basketball of course so it was basically just a game of smear the queer with me being the targeted queer. That fucker Rick kept pushing me and dunking over my head like I wasn’t even there all the while laughing and jeering at what a wimp I am. I’ll never forget his taunts.

“Hey bitch tits! I thought you could handle balls better than that!” Or “Yo fire crotch quit staring at my dick and try to defend against me.” And my personal favorite, “Shoot the ball Chubby Stubby you can fondle all the balls you want after class!”

Even the coach laughed at that one. I was so relieved when class ended I practically ran to the locker room to change before the coach could make me take a shower. If only he’d been there maybe things would have gone differently but he left early today and never came to the locker room. I was surrounded before I knew it. Rick and his goons were all standing around me just waiting for me to take off my shorts. They didn’t even try to hide it. I waited and stalled as long as I could but Rick was on to me and put an end to my stalling with a simple command.

“Coach left me in charge guys so I gotta make sure everyone showers. It’s the rule after all. Let’s go bitch tits, that means you too!”

The guys all laughed and started to take off their clothes. They were all standing around me blocking my exit and in just a minute or so they were all naked. There were six of them. Six tall, muscular, confident, black guys gleaming with sweat and smelling like body odor and unwashed crotches. I stared straight ahead and tried desperately to not look down but just knowing all those dicks were out in the open made me so nervous I was shaking. I pulled off my shirt first and they all had a good laugh at my pudgy body.

“Damn boy you ain’t got no hair on your chest at all, you sure you ain’t a girl?” Shouted one of them. “Look at those nipples! They all puffed out and shit! Damn bitch tits you making my dick twitch with them smooth, hairless, puffy titties.” From another. And from Rick, “Fuck I can’t believe you Stubby, you look like a fucking shemale wimp. I hope you make up for it between them legs. Let’s find out. Drop them shorts sissy boy.”

My hands were shaking so hard I couldn’t grab both my shorts and the panties at the same time. I really tried to pull them down together so maybe the guys wouldn’t see but all I got was the waistband of my gym shorts so the panties stayed on when the shorts came off. And the crowd went wild! They were laughing and shouting all at once so I had trouble catching every word but I got the gist. 

“Oh shit sissy are those panties?” “Holy shit the boy is wearing panties! He’s wearing girls underwear!” “What a faggot!” “What a fucking wimp!” And, “What a sissy bitch! Jennifer was right, she did see a whale’s tail on this bitch! He’s a fucking fag crossdresser!”

I tried to argue, tried to tell them I was wearing European men’s underwear. I tried to tell them it was a joke, that I had been dared by a friend, but nothing worked. They knew that I’d worn panties more than once so it was definitely by choice. I was ruined. I started to cry and pulled up my shorts as I ran to the door, but strong arms stopped me and before I knew it they had pulled off my shorts and pushed me out into the hall in nothing but my step mother’s dirty panties. Thank god the bell had not rung yet. I bolted for the nearest exit and ran into the woods behind the school. I kept running till I was out of breath, which I’m ashamed to say was about two minutes. Then I crept through the woods till I got lucky enough to find an old tarp draped over a tree limb, probably some homeless person’s bed, who knows? I wrapped it around myself and made my way home and have been hiding in the garage all afternoon till my stepmom got home. I sneaked into the garage while she was unloading groceries and ran to my room and I’ve been cowering here since. Oh Journal, I can’t go back there! I just can’t! I need to think, I’ll write more tomorrow. I’m so tired.

Sept 3rd, Morning

Oh god Journal I feel like screaming but I don’t dare make a sound. I’m actually hiding in the bathroom writing this. I heard the doorbell early this morning just as I was waking up. My plan was to fake sick and hide out in my room all day but you’ll never believe who was at the door. It’s Rick! Rick Fucking Jefferson is downstairs talking to my stepmother! I can’t believe what I’m hearing. First of all he’s telling her he’s worried about me being bullied so he came here to make sure I’m alright and to give me a lift to school. He’s acting like we’re friends and he’s looking out for my well being! Oh Journal, the stepmonster is falling for it too. She’s telling that prick what a nice young man he is and how much she appreciates his help with poor Kenny. She fucking said I was uncomfortable with my body and needed a positive male role model like Rick to look out for me. My life is over! They’re laughing and talking to each other like they’re old friends or like they’re on a first date or something. This is horrific! 

Oh fuck, she’s calling me downstairs! She knows I’m here. Hopefully I’ll be right back, Journal. I need to play this sick card and get back to my room. More later.

Sept 3rd, That Night

I’m going to take my time tonight Journal because I’m still kind of in shock and I don’t want to leave anything out. Ha! As if I will ever forget a single second of today. It all started when I went downstairs to tell the stepmonster I was sick. She was standing there in the kitchen offering Rick a cup of coffee and they looked like old friends grinning at me like I was the fucked up elephant in the room. Stepmother Celeste went to sit at the kitchen table and Rick pulled out her fucking chair! What a psycho this guy is. I mean this guy is the bane of my existence and here he is making nice with my step mother and smiling at me like we’re having a family moment. It was surreal for me and I had to just stand there for a few seconds to make sure I wasn’t having a stroke or something. But no, I’m not that lucky. 

I just started to speak when Rick cut me off with, “So Ken old buddy I was just telling Celeste about the trouble you’ve been having in school with those awful bullies and how I wanted to help you out in any way I could. So I’m going to make sure you get to and from school every day without any trouble. I told her I was going to help you out with some after school activities too so you don’t have to hide away in your room playing video games all the time. I mean it’s our senior year buddy, we should be enjoying ourselves not worrying about a few bad apples ruining things. I’m going to stick by you my friend and make sure you get the most out of this school year.”

Celeste said, “Oh Richard you’re such a good friend to our poor Kenny. He’s lucky to have you in his life. I’m sure you two will have a wonderful senior year. But you boys better hurry or you’ll be late for school. Kenny, go get dressed and don’t keep Richard waiting now, shoo.”

I tried to tell her I was sick but she wasn’t hearing it. Rick had told her I faked sick sometimes to avoid my bullies and he said, “Now that I’m here to protect Kenny I’m sure he won’t have to do that any longer.”

And that was it. My perfect plan was ruined and I had no choice but to either admit to Celeste exactly what was going on or go along with my psychotic bully’s evil plan. So I got dressed and went back downstairs to find Rick standing behind my stepmom, pressed right up against her holding her arms, and showing her how to swing a golf club. I could see him grinding his crotch into her ass and she didn’t even seem to notice! The prick was smiling at me while he pressed his fat cock into my stepmother’s asscrack. And then she thanked him! Thanked him for helping her with her swing! What the fuck?

When she noticed me standing there she blushed and moved away from Rick and said, “Well you should take off now guys, after all you don’t want to spend your time with an old lady like me do you?”

“Old?” Rick said in faux surprise. “You are definitely not old Celeste. In fact when you first answered the door didn’t I mistake you for Kenny’s sister? I mean you are a young, attractive, vibrant woman so don’t talk about yourself that way. I won’t have it.”

“Oh Richard, you’re so sweet! I’ll bet the girls can’t stay away from you can they? You’re probably fighting them off with a stick.”

Then the prick said, “No, not at all. I mean sure there are a lot of girls interested in me I guess, but I’ve always been more attracted to more mature women. They always have so much more to offer of themselves.”

Celeste blushed and smiled at Rick and actually bit her lower lip like she was flirting with the creep. I mean sure she’s ok looking. I mean she’s tall for a woman, about five foot eight, and she has big boobs that still stand up tall. It’s not weird that I notice them, I mean they’re huge and she wears such tight tops with, what do you call it? Plunging necklines? Anyway she has one of those rap video asses too. Big and round and jutting out in her yoga pants. And yes I guess you could call her face beautiful, especially her blue eyes and long blonde hair, but still she’s my stepmom! And Rick, that fucking asshole, is actually hitting on her!

When she finally got herself together from her blushing and smiling, Celeste said, “Well Richard you are welcome here anytime you like. This house is always welcoming of a polite, handsome, young man like you. Stop by anytime at all.” She said in a whispery kind of voice and I swear she looked down at his crotch while she said it. Then Rick grinned at her and said, “Oh I will Celeste, I definitely will.”

I was so stunned I just followed the bastard out to the car and got in before realizing what I was doing and just how much danger I was actually in. 

Things went from bad to worse when I got in Rick’s car. He immediately reached over and grabbed my left nipple in his huge hand and started squeezing and twisting it really hard. He leaned in so his face was just inches from mine and said, “Now you listen to me you little bitch, I’m only gonna tell you this once, you will behave, you will obey me, you will do everything I tell you to do or I will beat seven shades of shit out of you. I’m not playing around here! We got all the pics we needed from our phones of your little panty run yesterday and unless you want them posted on every faggot website out there you will be a good sissy bitch and obey your superiors! Do I make myself clear?”

I’m ashamed to say I started to cry Journal. I couldn’t help it! My nipple was burning in pain and he was so close to me I could smell his sweat and feel spit hitting my face while he yelled at me. I gave in. Just like that I gave in and said, “Yes! I will do everything you tell me to, just please stop!”

Rick gave my sore nipple another strong squeeze then finally let go laughing the whole time. He called me a faggot and when I corrected him he reached for my nipple again and I quickly said I was sorry.

By the time we pulled into the school parking lot I had finally got my sobbing under control and my plan was to just run to homeroom and try to avoid Rick and his crew all day. Of course that was just stupid because he pulled in right next to Jennifer’s car and she leaned in my open window to talk across me like I wasn’t even there.

She said to Rick, “Hey baby I see you picked up the trash on your way here. You may have to disinfect your car seat if this sissy bitch is leaking from his little pindick. I’m sure being around a big strong man like you has this chubby fuck hard as a rock. Well a pebble anyway. Oh My God! You fucking bitch tit faggot are you breathing on me? Did I just feel cockbreath against my arm? So Gross! Hold your fucking breath faggot or lay your head on my man’s lap so I don’t have to feel the sissy air coming out of your doughy body.”

I was in a panic so I tried to hold my breath but Rick pulled me down so my face was right in his crotch. Then he repositioned the steering wheel so it pressed against me, pinning me in his crotch. Jennifer and her cronies laughed hysterically at my wiggling and squirming trying to extricate myself from Rick’s lap. I could smell his crotch through his expensive jeans, the scent was so strong I wondered if he ever bathed at all. His crotch smelled like sweat, B.O., and unwashed balls and it was making me lightheaded. Rick and Jennifer talked forever as if I wasn’t even there gabbing about the big game this weekend and how Jennifer’s parents would be out of town for a few days. It was hell being stuck there but I started to feel something rubbing against my backside and realized Jennifer was leaning so far into the car that her wonderful tits were brushing against my bubble butt. 

Again I panicked as I started to feel my traitorous little dick starting to swell. The position I was in meant my legs were rubbing together with my penis stuck between them. The feel of Jennifer’s tits on my ass was heavenly and she was talking so animatedly that her huge juggs were literally bouncing on my buttock. I tried to speak with Rick to make him let me go but my words were muffled by his lap. He must have become irritated by my movements so he pushed my face further into his crotch and I could now feel his cock pressed against my lips. Even soft it was enormous and I was forced to take a moment to appreciate the sheer size of it. But this distraction didn’t last long and I soon felt my penis start to twitch and pulse from the friction of Jennifer’s boobs against my body. I really started to squirm and tried to pull my legs apart to relieve the pressure on my dick. Jennifer saw me moving my legs apart and started laughing.

“Oh my god, Bitch Tits has a little stiffy from kissing your cock Rick!” She squealed with glee. This brought a round of uproarious laughter from the entire gang standing around Rick’s car. I could hear the distinctive laughs of the cheerleaders and jocks alike and I felt the tears building up in my eyes again. 

Then it happened. Oh Journal I couldn’t help it! Jennifer was still leaning in the car window while laughing and her tits were bouncing on me and, and, and I couldn’t stop it from happening! My little dick shot out the biggest load ever, staining my pants and quickly forming a wet patch on my crotch. 

“EWWW! The little faggot just squirted its sissy juice in its pants!” Jennifer screamed. 

Rick released my head from it’s prison and got out of the car running around to the passenger side and quickly pulling me from my bent over position and onto my knees in the parking lot.

“You fucking faggot, you got off sniffing my balls? What the fuck you queer?” Rick shouted at me. 

Luckily the crowd of popular kids encircled me so no one else was privy to my humiliation but even this small group was enough to ruin me. They were the kings and queens of the school and I was now completely destroyed. They would never let this go. I had to find a way out of this school forever.

I was sobbing openly now and tried to explain it was Jennifer’s tits and not Rick’s crotch that made me cum but that only angered them further. “Oh so you’re getting off on my girl’s tits, is that it sissy? Are you scamming on my woman? Do you think you have a shot with her?” Rick taunted me.

“No!” I said. “It was an accident! I didn’t mean it! I’m not gay! I just wanted you to know that I’m not gay and it was not your, um, your package that made this happen. I’m sorry, I’m so sorry!”

Rick bent over and grabbed both of my nipples between his thick fingers and twisted them so painfully that I cried out in a high pitched squeal like a little girl. They all thought it was funny and Jennifer said I sounded like the piglets on her uncle’s farm. This got a great laugh from everyone but me as I was still crying from the pain in my burning tits.

“Now you better tell me the truth faggot. See I don’t think it was my lady’s tits that made you cream your panties, I think it was the smell of a real man’s cock and balls. I’m gonna need you to tell the truth now so everyone here knows what a fag you really are. So, tell me, did the smell of my balls make you cum?” Rick said as he twisted and pinched my nipples harder and harder. I was crying openly now and trying to pry his hands from my chest but his grip was far too strong. I pleaded with him, telling him I was sorry again and that I’m not gay. I begged him to let me go but he just twisted harder and I thought for sure my poor nipples would never be the same from this torture. I tried to hold out, I really did, but it hurt so much. 

“Yes!” I screamed. “It was the smell of your crotch that made me cum. Please let me go! I’m sorry! I came from smelling your balls!”

Rick released my nipples and took a step back grinning like the arrogant prick he was before saying, “I don’t think that’s good enough. First of all you didn’t cum. Sissies don’t cum, sissies squirt. Also I didn’t hear you admit to being a faggot. Now try again and be sincere or it’s titty twisting time again.”

I leaned back and looked up at his smirking face and could feel my shirt pressing against my sore nipples making me cry out in pain. Jennifer said, “Eww, look at his puffy nipples. He looks like he’s growing a pair of sissy titties right in front of us.” Which of course made everyone laugh again.

So Journal, there I was on my knees on the hard pavement of the school parking lot surrounded by the worst people I’ve ever met, about to make a proclamation that will undoubtedly change my life forever.

“I’m very sorry Rick” He interrupted me saying, “Call me Sir from now on sissy.” So I started again.

“I’m very sorry Sir. I’m such a faggot that smelling the cock and balls of a real man made me squirt my sissy juices in my pants. Only a sissy faggot would squirt from smelling a man’s balls. I’m sorry for being such a useless sissy queer Sir.” 

“Whatever” Was all Rick said as he walked past me to put his arm around Jennifer’s shoulders and give her a long, wet, sloppy kiss before saying over his shoulder. “You meet the ladies in the girl’s locker room during homeroom sissy. They’re gonna get you cleaned up and presentable for your classes. Let’s go baby, the sissy can find its way or it can follow you and the girls. I’m done with it for now.”

I have to stop for a while Journal, I’m just too upset to tell you what happened next. I’ll write more later.

Sept 3rd, Later that night

Ok, I’m back. I just needed a little time to organize my thoughts. You see Journal when I followed the girls like Rick told me to, they led me to the girl’s locker room just like he said. I thought he was joking but there I was in the most forbidden room in the school for a guy to be in. I can’t even describe the feeling of being in that room where every girl I knew in school got naked. If those walls could talk. Well, after today I’m glad they can’t. Here’s what happened.

Jennifer and her friend Courtney took me into the shower and told me to strip. I told them, “No freaking way!” But then Jennifer slapped me in the face and I guess my face got red and I got tears in my eyes. I wasn’t crying! I wasn’t!

But she said, “Oh christ the little bitch is crying from a slap in the face. What a fucking faggot!”

Then all the girls laughed and Courtney grabbed both of my nipples and squeezed them both really hard, twisting them at the same time. She said, “This is how Rick controls the bitch isn’t it? Do as you’re told fag boy or I’ll twist these fat tits of yours right off!”

Ok, I did start crying then, but it really hurt! She kept twisting till I dropped to my knees in pain then finally let me go when Jennifer told her to. She said I wouldn’t be able to take off my shirt if Courtney kept hold of me like that.

“Strip” was all Jennifer said to me but the look in her eyes told me not to disobey. I was shaking as I took off my shirt and crying even harder at the mean taunts from the girls as they all laughed at me. 

I heard things like, “Jesus Court you turned his titties purple!” and “Look how puffy and swollen his nipples are, it’s like looking at a cow after it’s been milked.” also “This little slut must love the pain cause it’s still here. Hell a real man would never put up with this shit.”

Jennifer said, “That’s the thing about white boys, they’re wimps and sissies just like this one. None of them have the strength, intelligence, and shear strength of will that a black man possesses. Hell it only took a day for Rick to tame this one and now it’s learning its true place as a sissy bitch.”

I couldn’t believe it. This was the girl I’d obsessed over for years and here she was proclaiming me a sissy and an inferior white boy to the superior black men I now knew she preferred. She didn’t waste any time in furthering my humiliation either.

“Let’s go cow tits, strip off the rest of your dork clothes. Now! Move it!” Jennifer yelled at me.

I got up slowly on shaking legs and pulled off my sneakers and socks then I just stood there praying they would get tired of this game and let me go. No such luck though. Courtney made a move to grab my nips again so I quickly pulled off my pants revealing today’s panties. I thought I would be home all day! I swear! If I thought that bastard Rick would drag me off to school I would have worn my regular underwear. Instead I had on the bright blue thong Celeste wore to work out early this morning. I pulled it still steaming from the hamper and it was in fact still damp against my skin and smelled like overworked pussy and sweaty ass, a fact the girls didn’t miss. 

They laughed for a long time. None of them could speak; they were laughing so hard. I just stood there with my eyes on the floor, blushing from head to toe, and crying like a fucking wimp. I have never been so ashamed of myself as in that moment. What kind of man am I anyway? I guess not much at all.

Jennifer stepped forward and said, “Oh my god you smell like a whorehouse! How can you possibly have made your little panties smell like pussy! Are you that much of a feminized, sissy, faggot?”

I spoke without thinking. I mean my head was a mess. I mumbled, “They’re my stepmom’s.”

Courtney said, “What was that fag? Your stepmom’s? Are you telling us you’re wearing a thong that your stepmother wore first? Are you a panty sniffer too? Oh god you are pathetic!”

I couldn’t even look at her. Like all the other cheerleaders in the locker room she was beautiful. No, she was hot as fuck. They all were. Every girl there had a massive chest. It must be a prerequisite for joining the squad, having huge tits. Not one of them was smaller than a 38DD and I’m probably being conservative. They all had perfectly round bubble butts, you know the kind you see in rap videos? They all had perfect faces and perfect hair and perfect makeup. It was like they were all made in a porn factory. And here I was standing in front of them in my stepmother’s thong. A thong that smelled like her pussy and was soaked in the front with my cum. I wanted to die on the spot.

Jennifer held out her hand and told me to hand the thong to her. I just did it quickly so I didn’t have time to think about it. I whipped it off and placed it in her hand as fast as I could so I could get both hands over my package to hide it.

“So fucking gross!” Jennifer yelled. “This fucking thing is soaked with spooge and old lady cunt and swamp ass! Open your fucking mouth wimp!”

Again I obeyed without question because in my darkest most twisted thoughts I never imagined she would do what she did. She turned the thong inside out and shoved it in my mouth with the cum side right on my tongue. She forced my mouth closed with her hands and nodded to two of the other girls to hold it shut. While Britney and Zoe held my mouth closed Jennifer wiped her hands clean in my hair. I could feel my hair sticking to my scalp with the combination of mine and Celeste’s private juices. 

The girls all moaned and groaned and laughed at me saying how disgusting I was for eating my cum and my own stepmother’s pussy cream. They made jokes about how she’d probably fucked my dad that morning and I was eating his cum too. This was absolute hell. And it continued to get worse.

Jennifer stood in front of me and just stared into my eyes. By then I was a blubbering mess with tears running down my cheeks and snot running from my nose. Zoe cried out, “EWWW the freak’s snot just touched my hand!” And she and Britney let go of me.

I was just about to spit out the thong but Jennifer said, “You do and I’ll make you sorry you were ever born. Just hold that pussy sling in your mouth and suck on it for a while.”

I was terrified and disgusted but I obeyed. I was gagging a bit from the taste of the mess in my mouth but did everything in my power to keep from getting sick. 

“Move your hands sissy” Jennifer said.

I blinked at her stupidly even though I fully expected her to say that eventually. I stared at a spot on the wall behind her as I slowly moved my hands away from my crotch. The laughter was louder and harder than ever. Something I thought impossible. Oh Journal it was horrible! The things they said were so cruel. I’ll never forget it, never!

“What the hell is that thing?” one of them said. “It looks like a miniature model of a cock.” Another said. “How the hell does the sissy piss with that thing? There’s not enough of it to hold onto.” And then Jennifer chimed in. “It’s like I always tell you girls, white boys are useless, little, sissy fags that could never please a real woman. Just look at the proof before you. This tiny specimen is typical of the white race. That’s why Rick loves turning them into sissies and why I love helping him do it. We’re really just showing these white boys their proper place in the world.”

Those words stuck with me because they scared the hell out of me. What did she mean about her and Rick turning boys into sissies? This was getting way out of hand but just as I was about to say something two of the girls grabbed my arms and started pulling me toward one of the shower heads. They turned on the cold water and held me there under it till I was shivering so badly I thought I would die. The girls were all laughing at me as I struggled to free myself but these two slender cheerleaders were too tough for a wimp like me I guess. By the time they pulled me from the water I was a crying, shivering mess and just fell to the floor. My penis was even smaller thanks to the cold water and the girls started calling me Button Dick and then just Button. Jennifer said it was a great sissy name.

Before I could catch my breath they pulled me over to the lockers and sat me on a bench before opening several lockers and taking out a bunch of clothes and assorted small containers. I soon found out the containers all held makeup and before I could protest they were already working on my face. It was so strange sitting there naked in front of all these girls while they made up my face. I had no idea what they were doing and was too afraid to interrupt. Jennifer was the ringleader and gave directions to the girls telling them to apply more blush or smooth out the eyeshadow or use a sluttier lipgloss.

They were all having a wonderful time laughing and joking as they painted my face and after an interminable amount of time it was finally over. Well, the makeup part was anyway. Then came the clothes.

It started with underwear because the thong I was sucking clean was no longer fit to wear. They had several pairs of panties for me to try and they laughed and cheered as I tried each one. The first was a pair of white cotton boy shorts that everyone said were too normal for a freak like me. Then came a pink bikini cut, but no one liked the look on me. So they moved on to a pair of seamless, floral lace, butt hugging panties with the lacey floral pattern covering my ass and a solid front panel that was tight against my crotch and barely showed a tiny bump where my penis was. They thought it was perfect so here I stood in the sexiest panties I’ve ever worn, the effect being ruined by the girls taunts and laughter. 

But oh Journal that feeling of lace on my backside and the silky texture of the front panel rubbing on my tiny cock and balls was just too much for me and my traitorous penis stood up straight, mocking me with it’s useless size.

“Oh my god, the little freak has a chubby!” Courtney said. “No, it’s a button,” Zoe chimed in. “It’s his tiny sissy button,” Jennifer said laughing.

Courtney reached down and flicked my penis with her index finger making me wince in pain but the damn thing stayed hard. I wanted to cry again but I was warned not to smear my makeup so I held it in with sobs shaking my body and making my chubby tits bounce to my humiliation and the delight of the girls.

One of them, Reece, the owner of the panties, pulled out the matching bra and they all laughed harder at how well my tits filled it out. “It’s a gift for my little sister,” Reece said. “She’s just starting to grow her boobies and I wanted her to feel sexy. I figured the bra would fit our little Button here since he looks like he’s the right size for a training bra.”

Now I knew true humiliation as they started comparing my tits to those of a little girl. My shame was growing with each passing minute. A pair of white lace stockings with a frilly band around the top finished the look and the girls led me to a mirror and showed me the finished product. I looked like a girl. No, really. I looked just like a girl. There was no sign of masculinity anywhere to be seen. It was awful! The makeup was so subtle it looked perfectly natural, except for the very slutty red lipstick that made me look like a whore. I pleaded with my eyes and struggling moans through my panty gag for the girls to let me wash it off and change clothes but they said not to worry since no one in authority would see me. I was puzzled by this and terrified at the same time. Then Zoe pulled out a pair of handcuffs from her locker and they locked my hands behind my back. Courtney pulled off the pantyhose she was wearing and put the crotch right against my mouth before tying them around my head to secure the panty gag in place. I watched in horror as they threw my clothes in the trash and began pulling me toward the door. 

Jennifer led the way and as she opened the door leading into the hallway she looked both ways to ensure no one was coming before ordering the girls to bring me forward. She quickly led the group of us across the hall into the boys locker room and it still being 1st period, the room was empty. They dragged me to Rick’s locker and quickly shoved me inside. I was whimpering and crying as they all stood there laughing and mocking me ruthlessly.

Jennifer said, “Rick has Phys Ed later today as you well know but this locker room will be busy all day. You’d better stay quiet and stay hidden in here till Rick lets you out. You wouldn’t want anyone else to find you would you Button? That’s a good sissy. Bye Bye Button!”

And with that she slammed the locker door and put the padlock back on leaving me crammed in that stinking sweat box as she and the girls walked away giggling at my predicament. Then the bell rang and the first group of guys started banging and slamming their way into the locker room. I stayed as quiet as possible praying no one would notice me. And the worst part? I was hard the entire time! More later Journal. I need to go downstairs and spend a little time with dad or he’ll think something is wrong.

Sept 3rd, Even later that night

Things were weird downstairs Journal. Dad was sleeping on the couch and the stepmonster was acting strange. I heard her whispering to someone in the kitchen and when I walked in I noticed she was on her cell giggling and whispering to someone. I’m not sure but I swear I heard her say, “Here comes the sissy now, gotta go” before hanging up and smiling at me with this evil grin I’ve never seen before. Like she was taunting me or something. Then she said to me, “Why hello there, how was school today? Did you and Richard have fun together?” But it was the way she said it that freaked me out. Like she knew something. Like she knew exactly what happened to me today. I got flustered and just kind of ran back up here but she was laughing when I left. Maybe I’m being paranoid but I can’t help wondering who she was talking to on her cell.

Anyway, back to today’s torture. I don’t know why I’m writing this down but it just feels good to get it all out. It was such a horrible experience that I think writing it out is therapeutic in some way.

I was stuck in that locker for hours till I heard the bell for my gym period ring. Over and over the room filled with guys I’ve known all my life and I could hear them laughing and joking as they changed before and after each class. And through it all I was trapped in that stinking sweatbox dressed in women’s underwear. I hate to admit this but I kept getting aroused. I don’t know if it was the confinement, the chance of being caught, or the silky underwear but my tiny prick kept getting stiff. I have no idea how I ever managed not to squirt but thank heaven I kept my panties dry. I knew the schedule well enough to know Rick was about to enter the locker room. I started shaking in fear and embarrassment and I peed a little into my new panties. So much for dry.

When Rick opened the locker door they were all gathered around, all the jocks with their phones out and pointed at me. Some of them were filming and some were snapping pics but all of them were laughing. I was a sweaty mess at this point and the air felt cold against my skin as two of them pulled me out of the locker and pushed me down to my knees. 

“Well faggot we all knew you were a freak but we never guessed you were this fucked up.” Rick said to the laughter of his friends. The tall black man leaned over till his face was inches from mine and spit right into my face. He reached down and grabbed both of my nipples and lifted me up to my feet by pulling them and twisting them till I shot up like a rocket. I was in so much pain from what the girls had done to me and now Rick was making it so much worse. I started crying again and the guys made fun of me.

I was shaking in pain, fear, and humiliation and with my hands cuffed behind me I had no choice but to stand there and accept the torture being imposed by this strong, muscular, black man. I was the only white boy in the room and I was surrounded by the elite jocks of the school. Each one was over six feet tall, all had well defined muscles and rock hard abs, and each of these guys was handsome as well. The last time I was in this room I’d seen them all naked and I knew they were all hung like porn stars so I was also upset at having lost the genetic lottery as badly as I had. These guys were the top of the food chain and I was nothing to them but prey.

Rick finally let go of my nipples and said, “Well guys what should we do with this sissy bitch? I mean class was canceled since the coach had to go home early so we have the period free. Maybe we need to see just how much of a faggot this sissy is.”

My eyes opened wide and I started sobbing harder at his cruel words and the responding laughter from his crew. Rick started to turn me around in a circle as the guys made comments about my body.

“Look how well his bitch tits fit that bra! He’s got real titties!” one of them said, “Naw man look at that ass! He got an ass like one of them popstars or the Kardishimon girls.” Also, “I’m looking at those cocksucker lips and wondering if that lipstick will stain my dick!” Then Rick said, “Well we got all afternoon to see just what this bitch has to offer so step up gentlemen and let’s sample our gift from the cheerleaders. They tell me this bitch’s name is Button cause it has a little button for a clit in those panties. How bout it Button? You gonna show us your clitty and titties? We know you love to show off.”

I still had that damn thong stuffed in my mouth so I couldn’t say a word but I know the panic and fear in my eyes told them all they needed to know. But not one of them cared about me at all, they just saw a sissy faggot to use and they claimed it as a birthright or something. They just wanted to use and abuse a white boy as, I don’t know, some form of reparations? It’s like Jennifer was right and they were claiming their rightful place as my superiors. Me the inferior white boy with the tiny dick being forced to serve at the whim of these Alpha men. I had no fight in me at all by this point but I still struggled and tried to get away only to be grabbed by several hands and pushed against the wall of lockers.

Rick moved in quickly and pushed my bra down under my tits exposing the bruised flesh to my tormentors. They laughed and hooted at the sight of my puffy nipples and small breasts. Each one took a turn pinching and twisting my nipples as Rick rummaged around in the supply closet. When he returned the guys moved back to let him work. He’d found some weighted sandbags about the size of softballs along with some string and began tying them together with some sort of metal clips that I couldn’t quite make out. When he finished he turned to me smiling and said, “I know a way we can help Button to grow out his tits.”

He then moved in and clipped two alligator clamps to my nipples. The pain was blinding! I thought it was the worst thing ever. Until he let go of the sandbags. The bags were tied to the clamps and they hung about my waistline pulling my nipples toward the floor and making me scream into my panty gag. The guys were all thrilled with the result and loved the way it stretched my tits out. Rick pulled the bra back into place and stood back to admire his work.

“That’s a nice look for you Button. We’re gonna give you some real titties before we’re through. You’re gonna love it when you get to move up a bra size.”

Then he pulled my panties down to my knees and once again a group of popular people were laughing at my tiny dick. They made all the same jokes as before and took turns flicking my penis with their thick fingers. They laughed at the way it bounced back and forth and loved how red my face was getting from the humiliation of it all.

Then Rick stepped forward again with something new in his hand. He said, “Jennifer gave me this and told me I should be the one to use it on Button here so it’ll know who owns its ass.”

The bastard was holding a pink, plastic, chastity cage. Yes I know what that is Journal, I’ve watched a lot of porn. It’s a device that covers a man’s dick and keeps him from getting a hard on. It keeps him from having sex too. Well sex with his penis anyway. But when Rick explained it to the guys he said it was a device meant to keep sissies from getting too excited. He said sissies needed to have their clitties locked away so they couldn’t offend real men and women with the sight of such a pathetic little nubbin.

Without much preamble Rick placed the cage over my tiny penis and looked me right in the eye when he clicked the lock closed. He put the key in his pocket and said, “There are two keys faggot, one for me and one for Jennifer. We own your ass now and you will do as we say if you ever want to squirt your sissy juice again. You understand me?”

With tears running down my face I nodded to him in surrender and obedience. I had no choice, Journal! He has all the power now! He controls when I get to cum, and with the pictures and video they took today I’m completely at the mercy of Rick and Jennifer.

Rick pulled my panties back up and pushed me to my knees in the middle of all the jocks. He untied the pantyhose from around my head and told me to spit out the thong. It hit the floor with a wet slap and the guys all laughed when they recognized it for what it was. 

At a signal from their leader all the guys took off their shorts and underwear and soon I was surrounded by several black cocks of varying sizes and states of erection. None of them were completely flaccid which told me they got a sexual thrill out of abusing white boys like me. A thought that scared the hell out of me.

Rick said, “Now I think you know your place here sissy so I’m only gonna tell you this once. I want you to turn in a circle and plant a nice kiss on the head of every cock here and thank each one for the lovely gift we gave you. Thank us all for your new cage and for helping to grow your titties. Thank us with a nice open lipped kiss right on the head of our cocks.”

I whimpered like a little girl at that command and started to shake my head back and forth. Rick wasted no time in disciplining me as he reached out and tugged on the strings attached to my nipples. The pain was explosive and I’m ashamed to say this Journal but I did it. I did it. I started with Rick. I moved my face in close to his crotch and could immediately smell the ripe funk of his unwashed cock and balls. It smelled like sweat and stale piss and I moaned in disgust which Rick took as something else.

He said, “Listen to the sissy moaning like a slut. It can’t wait to taste my cock. Go ahead sissy, kiss that beautiful, black, dick!”

I leaned in and planted my lips against the head of his massive cock and was right away amazed by the soft texture of it’s skin. It was warm and soft, almost spongy in texture and it tasted like it smelled with the addition of salt. I tried to move away quickly but Rick warned me to show his dick some love. I kissed it for almost a full minute moving my lips open and closed the way I thought people kissed. It was so humiliating but Journal there’s something I’ll never admit to another soul. The combination of the smell, taste, and fee of that delicate skin along with the horrible abuse did something to me. I actually felt my penis starting to get hard and strain against its plastic prison.

Thank god for the panties or the guys would have seen it and made things worse for me. Instead they just continued the abuse they’d already started as Rick pushed me away saying, “If I let him, this fag will kiss my dick all day. Shit Button that’s enough, you gotta show my boys some love too.”

I moved around the circle as best I could with my arms behind my back and planted a kiss on each cock head with tears streaming down my face. When I finished Rick sat on the nearest bench and told me to move in between his legs. 

“Now that you’ve had a taste of cock bitch I want you to really think about it. Really think about how it tasted and felt. Remember the way my dick smelled, imprint it in your memory. I want you thinking about my dick all the time so I’m gonna make sure you never forget it.”

With those words Rick grabbed the back of my head and pulled my face into his crotch. He reached down and pinched my nose closed and held the head of his cock against my lips. I knew what this meant and I tried to hold my breath for everything I was worth. But Journal, I’m so out of shape! I couldn’t last very long!

I opened my mouth and took a deep breath and Rick took that opportunity to shove his cock into my mouth. It felt heavy on my tongue and just the head filled my entire mouth making my cheeks puff out to accommodate his massive girth. I wanted to bite down as hard as possible and even started to do so until I realized how futile that would be. It might hurt Rick but then his buddies would beat me senseless. So I sat there with that pulsing cock head in my mouth, eyes watering, hands shaking, staring up at my captor with a pleading look on my face. 

Rick said, “Just start swirling your tongue around Button and suck gently till I tell you different.”

I had to do it. I had no choice. I moved my tongue in circles around his piss slit and began sucking softly like pulling soda from a straw. I could feel his huge tool growing with each swirl of my tongue and with each suck the head moved further into my mouth.

Rick held my head in place so I couldn’t move at all and soon we built up a rhythm with me sucking and him moving my head up and down on his shaft. I’d heard about people choking on cock and have certainly seen enough porn where that happens but it didn’t happen to me. It’s weird but my gag reflex never kicked in. Before I knew it Rick’s cock was lodged in my throat and my nose was in his pubic hair. He was shocked and exclaimed, “This slut is deepthroating my cock! No bitch has ever been able to do that on the first try. Our little Button is a natural born cocksucker!”

The guys were so impressed they all started jacking off. How do I know this since my face was in Rick’s crotch? You’ll find out soon enough Journal.

I continued sucking on Rick’s cock unsure of whether or not I should feel pride in my skills at deepthroating while he moaned and continued thrusting his python down my throat. I was making noises like gluk, gluk each time his cock entered my throat and one of the guys said that was the mating call of the sissy white boy. Very funny.

Rick continued his assault on my face as I became accustomed to his length and girth and actually found myself calming down. It wasn’t as bad as I thought it would be. The taste of his cock was better after my saliva washed off all the sweat and old piss and I simply resigned myself to my fate. It never occurred to me what the natural ending to a blowjob was. Well, not until I knew it was about to happen. 

Suddenly Rick pulled my face up against his pelvis and my nose was crushed against his belly. I felt his huge balls against my chin and knew by the way they tensed up what was about to happen.

The first shot hit me out of nowhere. I was not ready in any way. I suddenly felt a thick shot of cum hit the back of my throat and slide down hotly into my stomach. I had to start swallowing as there was just so much of it I had trouble keeping up. Rick pulled his cock slowly out of my throat and each stream of cum was more difficult to swallow as a result. When his cock head cleared my throat my mouth soon filled with the bitter, hot, salty cream. There was so much of it I felt it running out of my nose as well as from the corners of my mouth. The heavy, earthy, salty flavor was making me lightheaded and I felt I might pass out if I had to ingest much more. Rick pulled out of my mouth and let the last three or four ropes of cum land on my face and in my hair. He picked up the pantyhose that had held my gag in place and used them to clean and dry his cock before shoving them into my mouth to ‘marinate’.

Then I felt it. Several thick hot ropes of cum slapping into my face, neck, chest and back as all the guys started cumming at once. See Journal I told you you’d find out soon.

It was like those bukkake flicks I watched on PornClps. I was soon covered in the cum of nearly a dozen black men. They all laughed and high fived each other as they looked down at my defeated features. I looked ridiculous kneeling there in a bra and painties with my makeup smeared, covered in cum like a common street whore. No, street whores have more dignity than I had at that moment. And it just got worse.

Rick got dressed and told his boys to clean me up. He said, “Hey guys I gotta go meet Jen so why don’t you boys take Button here into the shower and get him cleaned up. I’m thinking a low down, faggot, whore like this needs himself a nice golden shower.”

He laughed as he left and told his friend James to record it for posterity. The guys wasted no time in dragging me into the shower room and forcing me back to my knees. I tried to beg and plead with them but they had secured the pantyhose in my mouth with some filthy jockstraps from the locker room laundry basket. They tied a couple of them to my head and the smell of days old ball sweat made me swoon. 

Before I could even think the first stream hit me in the side of the head. I could smell the strong odor of piss right away and began to shake and cry. Nothing else in the world smells like piss and I now know how it tastes as well. Oh Journal they pissed on me! All over me! They pissed in my face and it soaked into the fabric of the jockstraps and pantyhose filling my mouth with the nasty flavor. I really can’t explain it with words. Salty for sure. Bitter. Earthy and raw like you know what it is but still can’t believe you’re tasting it. It was revolting! I had to swallow what got into my mouth because the gag prevented me from spitting. There was just so much of it!

The piss got in my eyes and burned terribly. It got up my nose and I can still smell it even now. It got into the holes the clamps made in my nipples and burned like crazy. And the laughter of those cruel men was like pure humiliation coursing through my veins. I was beaten. Defeated. 

The guys called me piss boy as they drenched me in their waste. They said I better get used to it because sissies made great urinals. They said they loved having their own personal human toilet when they partied and I realized they’d done this before. How many white boys had suffered this degradation?

As the last drops of piss dripped onto my shivering body the guys started leaving singly or in twos or threes, some of them spitting on me as they left. I could hear them talking and laughing as they got dressed and it was surreal how casual they all were after what they’d done to me. I cried and cried not even stopping when James came back in and uncuffed my hands. 

He said, “I’m sure Rick wanted you to stay locked up but I thought I’d give you a fighting chance to get home in one piece. You remember that when it’s time to suck my dick snowflake.”

With that ominous warning he left me there on the floor in a pool of stinking piss. I removed the clamps on my nipples and howled in agony as the blood returned to them. I spit out the gag and removed the panties and bra. After washing myself off I found some shorts and a tshirt in the coach’s office and made my way home barefoot. 

Now here I am Journal and I just know Rick will be back to take me to school tomorrow. I also know the stepmonster will be on his side again. But for now I’m just so tired. Until tomorrow old friend.

Sept 4th, Morning

I’ve been sent to my room Journal and I’m not really sure what’s going on. It’s been one bizarre morning so far and I have a terrible suspicion it’s far from over. Rick showed up this morning just like I knew he would but something strange happened and is still happening I guess. Ok, here’s what went down so far.

I got up this morning and got dressed for school, making certain to wear my regular underwear instead of Celeste’s panties. I decided not to take any chances. When I got downstairs Rick was already there and he and Celeste were sitting at the kitchen table drinking coffee, staring at something on Rick’s phone, and laughing away like old friends. When they saw me they both laughed even harder as Rick put his phone back in his pocket. I told them I didn’t want a ride to school today and since I didn’t want to be late I’d be leaving right away. Celeste stood up and told me I wouldn’t be going to school today, saying she’d already called me in sick. 

I suppose I should have immediately become suspicious but maybe I am as dumb as my stepmother thinks because I actually thought she was giving me a break and wasn’t buying into Rick’s ‘nice guy’ routine. At least I thought that way until she said, “So Kenny, what sort of underwear are we wearing this morning? Hmmm?”

As she and Rick began to laugh again I stuttered out a confused statement of denial that I’m sure sounded ridiculous. I stammered something like, “What? Underwear? Why? Underwear? What?”

They must have thought I was retarded because Rick walked over and knocked me on the head a few times with his knuckles and said, “Hello? Anyone home? Answer the lady sissy.”

When I tried to tell him not to call me that Celeste interrupted with, “Now Kenny, or should I say Button? Richard has already shared your predilection for your, shall we say, alternative lifestyle? And I think it’s about time you admitted your desire to explore your feminine side and your obsession with big, black, cock. You see little boy I’ve gone through your computer and have seen all the interracial porn, the sissy videos, the cuckold stories and cartoons. I know all about your secret love and admiration for all things dealing with black men and their amazing cocks.”

The room got completely still and silent as they both looked at me expectantly waiting for my response. Ok Journal I’ll admit to having a fascination with interracial porn but I look at it for the white women! I swear! They always get the hottest blondes to shoot the interracial stuff and that’s what gets me off, not the men. Never the men!

I tried to explain that to Celeste but she stopped me with, “Richard also showed me the pics and video from your time with him and the other boys in the locker room yesterday. It looks like you had quite a grand old time my little, sissy, son in law. You truly are a disgusting white wimp. I just knew Richard here was a real Alpha Man like all black men. I’ve been cuckolding your clueless father for years with a black stud of my own just biding my time till I can get my hands on his money. Now I find out you’re a sissy for BBC? Oh we are going to have so much fun with you dear little Button. I knew Richard had his eyes on you the minute I met him. I can always tell when a real man is about to break a new sissy in and I’m so glad it’s you. I’ve always known you were a weak, inferior, wimp but I never dreamed you were also a faggot for black cock. How delightful.”

My blood ran cold and I couldn’t move. He’s shown her the pics and video? Oh god! My life is over Journal! I was so shocked I just stood there staring at my stepmother like I was in a bad dream. Who knew Celeste was such a bitch? Who knew she was kinky like this or that she was into black men? 

Before I could get my head back together Rick stepped forward and said. “Go back upstairs into Celeste’s room and put on everything you find laid out on her bed. See me and Celeste here have been having a great time getting to know each other for the past 24 hours through texts and now we’ve decided that together we’re going to start your training right. If you speak right now I will beat your ass. Just do as you’re told. Now faggot!”

I was so scared I jumped when he said that last part and just sort of ran upstairs. I heard Celeste say, “Damn, you’ve already got the sissy trained rather well Richard dear.”

So I came in here straight away to make sure I documented everything while it was still fresh. I’ve locked the door and have no intention of going into Celestes room or back downstairs any time soon. My plan is to stay right here and wait them out. They’ll get bored before I do, I have my XStation in here after all.

Sept 5th, Morning

I haven’t slept much Journal so I’m not sure how long I’ll be able to write. I’m probably going to be able to recite the past 24 hours by heart since it’s all been burned into my brain in explicit detail. I’ll never forget a single second of it Journal, I swear. I need sleep so badly I might cry from exhaustion but I’m also too amped on the humiliation and pain of the past day to lay down. I’ll tell you as much as I can for now.

I wasn’t in my room more than 20 minutes yesterday morning before Rick came up and started pounding on the door. I was too afraid to answer so I just sat there cowering on my bed until I heard the key in the lock. That damned Celeste got the key from dad’s desk drawer. 

The two of them barged in and before I could even raise my hand to defend myself, Rick slapped me across the face and knocked me down onto the floor. It hurt like crazy and scared me to death. I was just laying there looking up at this towering black man praying he didn’t hurt me again when Celeste stepped forward and peered over his shoulder.

She said, “Now Button you be a good sissy and Richard won’t have to treat you so mean. After all he’s just trying to teach you to embrace your true self.”

I was rubbing my sore cheek and crying as I lowered my head to stare at the floor in defeat. Rick said, “I want to slap him around some more baby.”

Celeste responded with, “Now, now Richard dear we agreed to do this peacefully as long as the sissy obeys. Let’s give it the chance now instead of immediately resorting to violence.”

Rick said, “Then I’ll need an apology from the little faggot.” And Celeste said to me, “You heard a superior black man make a request sissy. If you know what’s best you’ll obey.”

I certainly didn’t want to be slapped again and I knew I had no chance against that muscular jock, so I just said, “I’m sorry Rick I’ll do what you tell me.”

He slapped the back of my head hard then said, “The fuck you just call me? You call me Sir you sissy ass faggot!”

“Yes Sir!” I whimpered. “I’m sorry Sir.”

“Not good enough.” The stepmonster said. “I think you should show more respect. Oh, I know! Kiss your better’s foot while you apologize.”

Rick laughed and the room took on a sinister tone as the two above me grew silent. I didn’t look up but I knew they were waiting to see if I would obey. Oh Journal, what could I do? Rick is so big and strong and I’m just a small, white, wimp. I'm quickly learning my place Journal. I really am. 

I bent down so my face was just above Rick’s shoe, leaned in till my lips touched the leather tongue and cloth laces, and planted a quick kiss on my hated bully’s foot. I was told that wasn’t good enough by Celeste and after a series of giggled instructions from that bitch, I tried again.

I was made to kiss, lick, and basically make out with Rick’s dirty shoe for nearly 10 minutes while the cruel couple above me laughed like it was the most amusing thing ever.

When they finally let me sit up I noticed Rick had his arm around Celeste’s shoulder and his right hand was cupping her right breast. He was squeezing and mauling her tit like he owned it and she was squirming into his chest like a schoolgirl with her hands roaming all over his abs and buttocks. I suddenly realized how much trouble I was in.

That’s when things got bad. Rick looked down at me and said, “Take off my belt sissy.”

I just blinked up at him for a couple of seconds and noticing the look on his face I quickly moved to comply. I reached up with shaking hands and unbuckled his belt then slowly began pulling it from around his waist. I feared he was going to beat me with it but what actually happened was much worse. 

He looped the belt around my neck and slid it into the buckle making a leash that squeezed my throat till I coughed and choked. Rick laughed at my discomfort and simply said, “Here sissy! C’mon sissy! Let’s go walkies!”

He and Celeste laughed loud and long at that as they led me crawling into her bedroom. I scrambled to keep up with my bully as the belt dug into my sensitive flesh. It was so humiliating to be treated this way in my own home. Crawling down the hall I looked at pictures of my dad and me in happier times. I had no choice but to look since I couldn’t lower my head so I was in tears by the time we reached the master bedroom just from imagining what my dad would think of all this. 

When we got to the king sized bed Rick let go of my leash and allowed me to stand. I was rubbing my neck and coughing from being choked. My eyes were watering so I had trouble focusing on whatever was on the bed. Rick had no patience for my recovery so he grabbed me by the hair and pointed my face to the bed forcing me to focus through the pain.

Oh Journal, it was too much. I knew what was expected and also knew I would rather die. Well, it never did come to that. Turns out I really am a wimp. Look, I have to lie down for a couple of hours. I’m just so tired. More later.

Sept 5th, Afternoon

It was an entire outfit Journal. That’s what was waiting for me on Celeste’s bed. It seems she’d done a little shopping at Rick’s behest and had purchased me my own clothes. There was a bright pink thong with matching bra and knee high stockings. A plaid, pleated skirt that was barely long enough to be called a skirt. It honestly looked about as wide as a scarf. A white button down top lay next to the skirt and I knew right away this outfit was a perverted version of a catholic schoolgirl uniform. The wig caught my eye next and my blood ran cold. It looked long, like shoulder length, wavy, red hair; an even deeper red than my natural hair color. There were assorted plastic hoop bracelets and gaudy rings laying in a pile along with what looked like pink, plastic, hoop earrings. It was all laid out in an orderly fashion that allowed me to see in true horror what was in store for me.

As I was taking in the scene I heard Rick’s voice from seemingly far away say, “Strip sissy.”

I turned to look at him and Celeste with tears running down my face and pleaded with them to have mercy. “Please Sir, please don’t make me do this. This has all been a mistake, a misunderstanding. I’m not gay! I’m not, I swear! I don’t want to dress like that, please Celeste think about what you’re doing. You’ve practically raised me and now you’re being so cruel. Please stop this.”

Celeste slapped me across the face and said, “Now you listen to me you chubby little faggot, I’ve barely tolerated you over the years and I’ve finally had enough! There’s a real man in this house for the first time and you will obey him in every way or I will destroy any chance of happiness you ever imagined having. I’ll see to it that your father sends you into the military. You think because you’re 18 you can make decisions? I have video and pics of you acting like a cumpig for a group of black studs so you’ll either join up or have them released online. Just think about what they’ll do to an overweight, out of shape, feminine, sissy faggot like you in the army.”

Then she reached out and grabbed my nipples and twisted them in opposite directions causing me immediate pain from all the abuse they’ve received lately. I squirmed and cried out in pain as my bladder released. 

“Fuck! This bitch is pissing his pants!” Rick shouted with glee.

Celeste glanced down at my crotch and the ever expanding stain of urine with a look of disgust on her face. “What a fucking loser you are Button.” She snarled. “Get out of those clothes right this instant you despicable little wimp.”

I had no choice. I pulled off my shirt first so she’d have to let go of my mightily abused tits and was shocked at the purple color of my flesh as well as the extra inch or so they stuck out from my chest. All this twisting and pulling and sand filled weights was having an effect on my poor puffy nipples and it looked like I’d moved up a cup size.

I pulled off the rest of my clothing with the exception of my underpants as I was terrified of Celeste seeing the cage that still imprisoned my tiny penis. I still hadn’t been able to remove it without the key.

Rick slapped my right tit then my left in quick succession and yelled, “Everything off bitch!”

I cried out in pain as I hurried to comply. I swiftly removed the last vestiges of my male attire and stood before my tormentors in nothing but a pink, plastic, chastity cage.

Celeste laughed for a few minutes before composing herself enough to say, “Oh my god that’s hysterical! I never imagined something so funny. Oh Richard when you break a white boy you really go all out. I love it! Maybe this loser’s father should have one of those too.”

I lowered my eyes in shame as Rick said, “That can be arranged baby.” And Celeste moaned as she stared at Rick with lust in her eyes.

I turned to face the bed and looked over the nightmare outfit laying there as Rick slapped my ass hard and said, “Let’s go sissy! Get yourself feminized!”

And so I did Journal. I did exactly that. I slipped on the thong and noticed how it just covered the cage between my legs letting the world know exactly what it was hiding. The bra was next and I felt myself becoming aroused thanks to my traitorous panty fetish. I kept my back to the awful couple so they wouldn’t see my tiny penis straining against the cage and making my panties shift.

I pulled up the stockings and nearly squirted in my cage from the silky decadence of it all. How wonderful nylon feels against bare, hairless skin. I almost moaned in pleasure at the feeling. The skirt and top were easy to slip on and I stood there like a fool hoping they’d forget about the wig. No such luck. Celeste helped me put it on and fixed it with a brush to make it look natural. From under the bed she pulled out a pair of black shoes with bows on them that she called Mary Janes. The damn things fit perfectly. There must have been 15 bracelets and 6 or 7 rings that covered my wrists and hands. Then the earrings. Thank goodness they were clip ons but Rick assured me I would be getting many piercings.

They each took hold of one of my arms and moved me to Celeste’s makeup bench making sure I never got a look in the mirror. Celeste then spent the next half hour making up my face as Rick slipped off his clothes and stood next to me with his half hard cock close enough for me to smell. I remembered that scent and am ashamed to admit it made my little prick twitch in anticipation.

When she finished my face Celeste turned me toward the mirror and I saw before me a slutty looking ginger with the look of a street whore. I could honestly envision the creature I saw in the mirror starring in one of those sissy hypno videos online with her mouth full of Big Black Cock.

Celeste disrobed while Rick stood me up and made me twirl around and show off my new look. When my stepmother was naked I couldn’t help but stare. She’d kept her body up nicely. Her hips and ass were tight from all the pilates and her tits, which I guessed as at least a 38DD, showed little sign of gravity’s effects. My little penis was pressed into my cage so hard I was in serious pain. 

Rick and Celeste sat side by side on the bed and had me kneel before them. Celeste said, “Now my little sissy son I want to make things clear for you. This strong, superior, Alpha, Black King next to me is your Master. But you already know that don’t you wimp? You’ve already submitted as his inferior and you know your place is on your knees at his feet. Now I want you to look at me. That’s it, look at mommy. I’m your mommy from now on. That’s all you’ll ever call me no matter who can hear you. Now I need to see my sissy suckle while I explain things so let’s go Baby Button, suck like a good sissy.”

I made as if to suck on her magnificent breasts and she quickly slapped me away saying, “That’s not what sissies suckle on. I think my naughty little Baby Button knows exactly what to suck.”

Rick laughed and my stomach dropped. Even though I knew this was coming I still felt sick. I tried the only out I could think of and said, “But mommy, your sissy isn’t gay! Your sissy wants to suckle on mommy’s beautiful boobies.” I tried to sound like a feminine little girl as I spoke to her in hope that her perverted nature would overcome her cruel streak. But to no avail.

She said, “My sissy is whatever I say it is, and I say my sissy is a Black Cock Loving Faggot. Now suck your Master’s cock and make it big and strong for Mommy’s pretty pussy.”

As Rick smirked at me and Celeste beamed with warped pride I crawled between my bully’s legs. I was sobbing again as I reached out with my hand to grasp his thick cock and was told by Mommy to only use my sissy mouth.

I needed my tongue and lips working in concert to welcome this hated appendage into my mouth and using the thousands of hours of porn I’ve watched as a guide I began to fellate my worst enemy as he squeezed and rubbed Mommy’s breasts.

Mommy moaned and said, “Now sissy here are the rules. When you are home alone with Master and Mommy you’ll always dress like the sissy you are and you will always address us as such. When you’re in school you’ll call Richard Sir at all times. You’ll get to learn that his wonderful girlfriend Jennifer is your Mistress and you will call her that in private and Ma’am in public. Every black athlete in your school is Sir to you and every white cheerleader is Ma’am. You are inferior to them in every way and will act accordingly.”

Master’s cock began to grow in my mouth and since his hands were busy on Mommy’s boobs she began pushing my head up and down in his crotch pumping his expanding cock in and out like she was fucking him with my face as wet, sloppy sounds came from my full mouth.

Mommy continued, “Here at home you will serve us in any way we command. You will keep this house spotless since housework is not for Mommies, but for sissies. We’ll buy you a nice maid’s uniform for cleaning days.” Master laughed at this but his laughter turned to a moan of pleasure as his cock reached its full length and slid down my throat.

“Every night you will watch videos of sissies submitting to Black Masters to reinforce your place in life.” Mommy went on. “We will train you properly and you will become a compliant sissy slave for us in short order or there will be dire consequences.”

She stood up and straddled my head with her hairy pussy pressed against the back of my neck. She began grinding her crotch into my head and she and Master were soon fucking with me in the middle acting as a weird sort of birth control or sex toy.

Mommy continued explaining my new life. “Now, as for your father. Well, we are definitely going to turn him into a sissy as well so we will need your help Button. We’ll come up with a plan and get started as soon as we are certain you are fully owned.”

I moaned in fear and helpless angst at the thought of my dear father becoming a cocksucking sissy like me but the constant thrusting of these cruel people quickly took over all of my attention as Master’s cock fucked into my throat at an ever increasing pace.

“Climb up here baby.” Master said to Mommy, “I need to feel that tight, white, married pussy wrapped around my dick right now.”

Mommy pulled me off of Master’s cock with a loud, wet popping sound and pushed me back onto my fanny as she climbed up onto that amazingly huge cock.

In one swift motion she sat herself balls deep on to her lover’s cock and began riding him with wild abandon. Before she was too caught up in their frantic fucking she spoke to me one last time saying, “Now Button, put your little nose in Mommy’s rosebud and start licking the spot where Master’s cock is sliding in and out of Mommy’s pussy. That’s your default position when we’re fucking.”

Resigned to my fate and fearing retribution if I failed I did as ordered and spent the next hour with my nose up Mommy’s ass and my tongue busily licking her pussy and Master’s cock. I knew this would become an everyday occurrence and as my tiny clit sized penis began to spurt it’s sissy juice I wondered briefly what other submissive horrors awaited me as a newly made sissy.

THE END?