Prom Sissy Ch. 03

This story has homoerotic and forced-sex themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned!

All characters in this story are over the age of 18. The entire story is fiction as are all characters. Any likeness a character has to someone in real life is merely circumstantial.

This story may not be copied without the direct permission of the author (me!)

If you enjoy the story or have any (positive or constructive) comments, please let me know.

*****

It was the morning. The night before felt like a dream but from the sticky mattress beneath me, I knew it had been real.

I was alone in the room. Still wearing the slutty outfit from the night before, i slipped a little as I tried to sit up. My hands, feet, ass- hell- everything was slick with either oil or cum.

I reached back and felt my ass. It was still tender from the night before and as I felt around it I felt it give way and a small stream of cum leak out onto the mattress below me.

I looked up, my eyes re-adjusting to the light. I slowly and wobbly got to my feet. I staggered over to the door.

At the foot of the door was a towel and a fresh set of clothes. The clothes weren't boys clothes, mind. They were another set of slutty lingerie, no doubt 'borrowed' from Norm's mother.- Where the fuck was his mom anyway?

Taking initiative, I used the towel to wipe the oil off from my body. I also rubbed my face clean of whatever make-up I could and climbed out of the sticky latex clothing and lacy panties.

I picked-up my newest outfit: a lacy partially-see-through three-quarter dress (I think it's called a 'babydoll'?); again, in pink. There was also a pink pair of panties to go with this one, but this time it was a thong. They had chosen to omit the bra this time...

I slowly pulled the outfit on, not wanting to walk out in the nude, and gave one last look around Norm's bedroom-turned-sex-den. Without anything further I pushed open the door.

On the landing I heard sign of life: they were in the lounge shouting about something.

I made may way down the stairs and just as I had taken the final step onto the landing, I heard it... a video playing from the tv in the lounge. With a sense of horror, I tiptoed around to the doorway and my jaw fell open at the sight before me.

Zoomed-in, in full frontal view, was my gaping asshole. On Norm's parent's 70" flatscreen my wrinkled hole shone through in high definition, glistening with lube.

Looking around the room, I was shocked to see all 3 boys fully naked still, sat around jacking off. Darnel sat closest to the door and was beating-off slowly in a rhythm that matched the pace in which i was now being fucked on the screen.

Bill looked straight at.me. He practically drooled staring at me in my slutty outfit. Darnel noticed him and turned to see me.

"Ah, the entertainment is here" he jeered, standing and letting his cock stand straight out in front of him. I practically cowered as he approached me.

He let his hand come down brush my face. "Shame no pretty make-up today. But that's what the girls are for'.

Girls?... GIRLS?! No. No, more people couldn't see me like this.

"Oh," he started, sneering at me, "you would prefer everyone just saw your movie then?" gesturing behind him as he spoke. "No. We've got some girls coming around, so we might not even need you anymore sissy boy."

Might not need me...

It was several hours later. The boys had turned off the video, gotten dressed and were lounging around watching tv.

I was sat on a box in the middle of the room. Darnel had fetched a wicker chest from Norm's parent's room, which felt splintered beneath my bare lace thong-clad ass. They had all gotten dressed; or more like they had all put on underwear.

Bill and Norm both had on boxer shorts, but Darnel had decided to rock a black g-string male thong. He looked like a greek sculpture with the waistband hanging down from his abs. I felt myself staring at the bulge at his crotch as he walked around, preparing the room.

The doorbell rang and my heart stopped. Darnel went to answer it and I heard girls giggling in the doorway.

I turned to try get a view of the doorway, but Bill came up from behind me and stuck a blindfold over my eyes.

I felt him kneading my ass too. His oversized belly rested on my shoulder, as he reached down and fondled my ass, probing up my crack.

The giggling got closer and I felt the groping subside.

"Now this ladies," began Darnel "is our date for to the prom".

The first of the girls spoke: "What, like all of you?"

"Yes Mary, all of us".

Mary?! As in my sister's friend Mary?!

The girls giggled again. I practically felt Darnel's smirk at the thought of humiliating me in front of these girls.

"What's that?" another one of the girls said.

"That is his iddy biddy dicklet" Darnel said plainly, clearing referring to my caged cock. "Now that she's a girl, she doesn't need a cock and instead only needs to focus on receiving."

In a sweeping fashion, the blindfold was lifted away and I was blinded by the light of the room. As my vision came into focus, I began to take account of who was in the room.

Bill and Darnel were there. Norm was nowhere to be seen.

There were 4 girls, 3 of which I recognised.

Mary was in the year above me. She had graduated last year, but still hung around the school as she had nowhere better to be.

Stacey was in our class. She was an attractive-looking nerd, with bright ginger hair and pastie white skin. She always had the tone of someone who was more dangerous than she looked: like she knew self-defence or something.

Then there was Liz. Liz was an utter bitch. For years she had teased me and gotten me in trouble. She would tell our teacher that I had groped her or tried to kiss her when we were younger: making my school life a nightmare. In part, she was somewhat to blame for my low social status. Darnel knew all this and had clearly thought this through before inviting her along.

Lastly was a girl I was unfamiliar with. It turned out that her name was Erin. Darnel didn't introduce us any further, but something was definitely familiar about Erin.

Darnel went on to reveal why the girls were here. "You see", he began, "each one of these lovely ladies is here for a different reason. They aren't going to be told each other's purpose, but you'll get to know very soon." -and so I did...

First up was Stacey. The other girls vacated and went to the garden for some early morning sun, whilst Bill, Darnel and Stacey went about positioning me better over a weird looking piece of furniture, I didn't recognise. BIll called it a chaise - whatever that was.

He opened the wicker box I was sat on and begun pulling out various toys and devices used by Norm's pervert parents.

Once the contents was strewn over the floor, Stacey bent over and picked up a small dildo. Of all the monsters that were piled up, she couldn't have picked a smaller one at around 4 inches long.

Bent over the chaise, bill pulled my panties aside to reveal my ass. I heard Stacey laugh, stood behind me watching bill start to finger my hole. I'd learnt compliance by now and took his invasive fingers like the good bitch they'd made me into.

Bill's slippery fingers spread lube deep into my ass, before suddenly retreating. Next came a pressure as stacey pushed the toy up against my hole. It glided in with ease.

"Wow," she said with amazement as I took the little cock.

"Yeah," Bill said, also admiring my ass. "She took my cock last night."

Stacey ignored him and just kept pushing the toy in. Without any effort, it was all the way in and she was busy thrusting it in and out. Bill spanked my ass and began fondling it as Stacey fucked me.

Stacey very clearly was getting impatient, as she pulled the toy from my ass and went rummaging around on the floor for something bigger. I watched as she picked up several, some massive, placing them on the cabinet beside her.

Bill's cock was right at my eye line. His excitement was clearly shown through his underwear, the front slightly damp from pre-cum.

I felt once again the familiar pressure as Stacey readied her next toy at my ass. Still, my welcoming ass took the cock like a good slut and she was back to her usual thrusting.

Bill took off his boxer shorts to reveal his cock, rock solid and covered in veins. His balls looked bulging, no doubt full to bursting with cum.

Stacey seemed to pay him no mind, so focussed on fucking my ass. Bill went about popping his cock directly in my open mouth, pushing it straight down my throat to double-stuff me.

Once again, Stacey swapped over her cock for a bigger one. My ass was accommodating them well, but the size was starting to get too much.

"This is a doggy dildo," Stacey jeered, unable to keep the glee out of her voice.

Bill bucked slightly, pushing his cock the deepest he had put it down my throat. My gag reflex had apparently dissipated, as I took it like a trained hooker.

Stacey continued to push. I felt tears well-up in my eyes: a culmination of the pressure in my throat and up my ass. I suddenly felt an incredible bulge forcing my ass open and let out a silent scream on Bills cock.

"Oh my god, she's taking the knot, the little bitch."

Bill let out a moan and forced my head all the way down his shaft, so that my tongue tickled his balls. He erupted, cum pumping directly down my throat.

"Oh you fucking slut," Stacey chuckled in her high-pitched happy squeak. "You're gonna make such a good little prom date."

The pressure subsided and Stacey withdrew the doggy dick. She pushed another toy in my ass, but it didn't penetrate very deep: it was thicker far more than it was long.

Bill withdrew his cock. I'd have spilled his cum, if it wasn't injected directly down my throat. He stumbled backwards and sat down on the couch.

Stacey put down the dildo that had split my ass open directly in front of me so I could see it. It was massive enough without the giant bulb half way up to the balls. The shape did indeed look like a dogs...

Stacey pulled me up and returned my panties to cover my ass. The toy was still buried. It was at this moment I realised that it must have been a butt plug.

Bill sat panting on the couch. Stacey paid him no mind as she walked past him to go outside. I just stood there, ashamed of myself for what had just happened.

Liz walked in. She looked very different than when she had left. She was dressed only in a string black bikini. She was accompanied by Norm. Norm was totally naked himself and was frantically jacking his cock, whilst walking next her, his hand resting on her ass.

She carried a small black knapsack. They both stopped in front of me. Liz was grimacing, a menacing smirk. Norm was looking down at my body. My legs still sticky with lube, he took his hand from Liz to run up my thigh. I shivered at the thought of my friend touching me in a such a way.

Liz wasted no time. All business, she dropped to her knees and opened the knapsack. From within, she pulled out something small and baby-pink. It looked like plastic, but I couldn't make out what it was.

"Don't look so confused sissy," Liz started, "you should be made familiar with a chastity cage."

A 'chastity cage'? Oh fuck... I've heard of those before. Cuckolds get put in them to stop them having sex...

Norm's practically salivating over me at this point. His hand frantically jacking himself off as he gropes me. Liz reaches up toward my panties, to which Norm quickly lowers them for her. As Liz begins pulling my penis around as she attached the device, Norm begins to fiddle with the plug in my ass. He pulls slightly, forcing me to moan at the additional pressure.

For the first time since he came in, Norm lets go of his own cock and instead walks around behind me. He feels with both hands the massive toy buried deep in my ass.

With a final click Liz finishes with the cage. She Stands up, clutching the knapsack. Standing at my same height, she gives me a little kiss. Taken aback, I fall into her slightly, melting at her touch. She stops quickly and steps back to admire my whole form, all whilst Norm's still attempting to gape my hole with the toy.

"Darnel asked me to bring you some special treats, baby girl," she said. Reaching into the bag, she pulled out... I don't know what it was. At first I thought it was a bra, but it was flesh-coloured and looked like... tits?! She had a fake pair of tits in her bag. What the fuck?!

Norm stopped playing with my ass for a moment and stared at the fake tits. Liz smirked and stepped back to me, pulling the babydoll from my body. From there, strapped the tits onto me, sort of like a bra. They were so realistic... I felt... feminine.

"Give 'em a go, Norman."

Norm obliged and quickly began to feel up my new breasts. I couldn't feel it very much, but they certainly seemed to satisfy Norm, who was growing even more insatiable by the minute. Whist his hands explored my body; one making it's way down to clench around my locked penis and cup my balls, his cock was being pushed into my ass cheek. I felt the familiar wetness from his pre-cum as one of my best friends treated me like his newly-paid-for hooker.

"OK," Liz continued. "One last touch." She went on to pull out a mess of hair from the bag. She looked at me, reached out and took a tuft of my short brown hair, yanking hard.

"Ow!" I yelped.

Norm stepped back and slapped my ass hard. "Shut up slut!"

Liz rolled her eyes slightly at Norm's reaction, but her grimace widened all the same at the sound of my asscheek rippling.

"Yes," she spoke. "Yes, this will do nicely." I looked down at the dark red hair in her hands. Was she going to put that on me?

A few moments later, my question was answered. With 'wig tape', as Liz called it, she secured the hair over my own, decreasing my hairline ever so slightly. Norm had always said he was into redheads and the increasingly aggressive dry-humping of my leg told me that he may have had something to do with the choice in hair.

Liz proceeded to brush the hair out of my face and actually tied the hair up into little pigtails. When she was done, she stood back to admire her work.

"You look goddamn pathetic," she said. I looked down, ashamed at who I was becoming in front of my friends and the rest of the school.

To my surprise, Liz stepped forward, picked up my chin and stuck her tongue down my throat. She kissed me so patiently that my little cock began to strain in its new cage. I felt her hands cupping my balls and the other made its way to my butt plug, before pushing it in. After what felt like minutes, she pulled away, saliva dripping from her face.

"You are one slutty little cunt," she gasped, wiping the spit from her mouth. She turned on her heels, grabbed her bag from the floor and walked out the door.

Norm, apparently hurt at being so excluded through our makeout, turned me around.

"Right, bitch. You're gonna make me cum now." His energetic nature, whilst also horny, made for something a little scary. He looked down at my ass, still plugged. "Darnel said we've got to keep you plugged," he said slowly, "so I guess I'll have to use your mouth."

Without having to be asked, I lowered myself to my knees. It felt automatic to me now, to be subservient. It would be unnecessarily complex to need to think for myself. Norm looked taken aback, but smiled, as he quickly popped his cock into my open mouth and went to town face fucking me.

My gag reflex had been tested a lot these past days and I took Norm's cock to the base every time. He was a filthy dirty talker whilst he fucked me.

"Oh yeah bitch, I'm gonna rape your mouth." And "Fuck baby, I'm gonna breed your little hole when I'm done."

Honestly, Norm was perhaps the darkest closeted pervert I had ever met.

Through his trash talk, I heard footsteps behind me. I went to turn, but Norm held my head tight, so as not to release his cock from my throat.

I heard Darnel laughing with Mary. Norm finally exploded and; unlike Bill, encouraged me to withdraw his cock. As it left my mouth, his cum sprayed everywhere. It got in my eye, over my face, my new fake tits, down to my little chastity cage.

Darnel and Mary laughed. Norm, without another word, waddled out of the room, in search of a towel to clean himself off, leaving me knelt looking at the far wall. Mary walked around to face me. To my shock and to my pleasant surprise, she was completely naked.

Darnel walked around too. He too, was naked. The too of them exchanged evil and lustful looks at one another. I noticed Mary's ass was a little red and wondered whether she was getting her own spanking from Darnel outside.

"Right, to his mom's room?" Mary asked Darnel.

"Yeah," he said. "Mrs Jeffords keeps them in her wardrobe. Norm showed me."

What were they talking about? He wondered. I didn't get much time to think about it, before I was pulled up off the floor by Darnel, as strong as he was, and led back upstairs, still covered in cum.

When at the top of the stairs, Darnel led me, not into Norm's room, but into his parent's room. He pushed the door ajar to show a messy collection of clothes strewn over the floor. We walked over the dirty laundry and crossed the room to the closed wardrobe on the far side.

Opening the door, I was met with a wall of pink. Norm's mom seemed to have a lot of pink lingerie, but this was more than what I was expecting. Littered in were reds and blacks, but mostly it was just bubblegum and hot pink. What really caught my attention however, was that almost all of it was latex.

"Oh goodie!" Mary squealed, jumping up and down, her tits dancing as she did so.

Darnel smiled at her and pat her ass lightly. "Pick your favourite and go get her dressed. I'll deal with this one."

Mary picked a number of latex pink garments for herself and scurried off to Norm's sister's room to presumably get dressed.

"Darnel," I started, "if you have Mary to take to the prom, perhaps you don't need me to-" -*SLAP*- I fell to the floor with a bang. The slap wasn't particularly hard, but it had certainly caught me off-guard. More than anything, was the emotional response: I felt tears welling-up in my eyes.

"I'm not even going to explain to you what you did. You know what you did."

He was right. A part inside of me knew that I was not to talk unless he gave me permission. There was a silence between us, before I spoke again: "sorry, daddy." He really had broken me.

A fleeting look of compassion crossed his face before I proceeded to pull items from the rack. He threw me a towel from the floor. It looked as though it itself could use a wash.

"Clean yourself up," he said. "I can't be having my date looking like she just left a bukkake."

I used the towel to get the most of the cum off. Darnel then turned to me and began getting me dressed.

It felt like I was being poured into a mould. The clothing was so tight that I actually felt grateful that it was only a short dress so that my legs weren't constrained. Around my neck, he fastened a collar. My new tits bulged the dress out something fierce and the cleavage almost bursting from the front.

Just as I was stepping into the pink stripper heels that had been picked out for me, Mary returned. She was still naked. I looked at her perplexed, but her evil smile gave nothing away.

"Ah, we're just about done," Darnel said to her. "And you?"

"Ready for her play date."

Completely confused, I was led by a chain on my new collar forward and into Norm's sister's room. Bent over the bed, dressed similar to me, was a hot-looking girl. Much like me, her dress rode up as she bent over, but where one would see my chastity cage, I saw her pink pussy lips.