Prom Sissy Ch. 01

Story Info
No date for Prom leaves the boys desperate for a date.
1.6k words
4.35
31.8k
45

Part 1 of the 3 part series

Updated 06/14/2023
Created 07/26/2022
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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 senior year and prom was coming up fast. All around us people were getting dates but my friends and me were still without any prospects.

My name is Michael. I'm 18, 5'5'' and 140 pounds. It sounds like a shitty dating profile- i know; or perhaps a bio before a fight. I have longer brown hair and a lean body type. I think I'm a pretty attractive guy, but I guess not enough to get a prom date...

My friends are Bill, Norman and Darnel.

It's not a surprise that Bill didn't have a date. He's a nice guy and all, but he's hugely overweight. He must weigh twice as what I do, but he's only 6ft.

Norman's got a different problem: the guy is just overly creepy. He's got this look that puts girls off. He frequently tries to engage in conversation over girls: pointing out their tits or postulating what their favourite sex position is. He's the kind of guy we all expect to be fucking hookers as soon as he leaves for college.

I don't get why Darnel has problems. He's tall, handsome and athletic. He plays for the football team and is built like a machine. Maybe it has something to do with that he's black?- I don't think much about racism, but maybe girls just aren't into that around here... He was my friend friend and we'd known each other since kindergarten.

In all respects we really are the losers of our school. We hang out with just each other and don't get a second look from any of the girls.

It was 2 days before prom and we were getting desperate. We were hanging out at Norman's, with him showing us the condoms he had in his wallet.

"You've got to make sure you have a selection", he was saying. "I've got ribbed, flavoured, extra lube - for when they're so horny they'll put it in their ass".

"Who are you kidding yourself Norm? No one's letting you touch them, let alone fuck their ass", Bill interjected.

"Well if I do get asked at least I'll be prepared," he bit back. "We've got to be competing against all the big fat dildos they've got lying around, haven't we?"

"What the fuck are you talking about?" My comment came out of nowhere. It was uncharacteristic of me to be so aggressive.

He looked back at me, a little hurt. His expression quickly changed to anger as he went on. "Well all these big dicks they take now. Their probably sat at home every night fucking themselves with big ones, long ones, ones that vibrate..."

"Girls don't masturbate," Bill cut in again. "And even if they did, I thought they just used their fingers?"

Norman scoffed. He turned tail and walked out the room. We all looked at each other perplexed by his sudden disappearance. As he re-entered the room, I stumbled back in horror. In his hand, he had a large veiny black dildo.

"What the fuck Norm?!" I found myself spurting out, "why do you have that?"

"It's from my sister's room" he shrugged.

"That's messed-up, man" Darnel took a step back as Norman re-approached them all.

"Nah. It's just a toy."

Bill was mesmerised by the veiny cock flapping in Norm's hand. "Uhh..." he stammered. "Is it clean?"

Norm gave it a sniff. "No," he shrugged.

"That's nasty," Darnel said with a disgusted look on his face.

"What does it smell like?" I asked, without thinking.

"Here," Norm held out the toy in front of me.

I hesitated, unsure what to do. Everyone was silent, waiting.

Slowly, I reached out and took the dildo from Norm. It was heavy. It must have been twice the size of my own and three times as thick. It felt rubbery and sticky to the touch.

I raised it to my nose and gave it a sniff. It smelled great. A potent musky aroma filled my nostrils and I brought it closer to my nose to inhale again. The others just watched mesmerised by the strange scene.

It was touching the tip of my nose as I breathed deeply a third time. Without thinking, without considering, I opened my mouth and brought the toy to my lips.

"What the fuck, bro?" Bill exclaimed, but the others both stayed quiet. Norm looked like he might salivate over the floor: clearly turned-on by the idea of someone tasting his sisters pussy juices. Darnel just stood there, intrigued.

Snapping myself out of it, I quickly withdrew the dildo from my mouth and away from my face.

Everyone just looked at me, stunned. "Why'd you stop?" Norm said, quietly.

Speechless, I just looked back at him.

"Is it because it's a black toy?" Darnel followed-up, his face challenging.

"What?" I said, exasperated.

"You don't like pussy when it's black, is that it?"

"Wha-, I-" I didn't know what to say to this. "No, it's not that Darnel..."

"Then what?" now he was getting increasingly hostile as he took a step towards me. Both the others stood silently cowering themselves. We didn't ever talk about it, but Darnel was very imposing. We all knew that even between all 3 of us, he would beat the shit out of us no problem, if it ever came to a fight.

He grabbed the dildo from my hand and raised it to eye level, pointed at me. "Go on then. Show you're not racist."

"Darnel..." I began to implore, but he had already thrust it into my open mouth.

Whereas I had almost ticked the end before, he practically chocked me with the huge toy. I stumbled back from the sheer force as it penetrated my mouth, but Darnel pushed forward, following me.

Tripping backwards, I found myself on my back. Darnel was on top of me, continuing to push it into my mouth.

I felt my eyes watering, my breath leaving me. Looking around frantically I saw Bill and Norman just watching me, not attempting to help whatsoever.

In final resignation, I closed my lips around the dick and began sucking, making slurping sounds to indicate to Darnel that I had submitted.

His pressure eased off a little and I felt my airway open once again. Able to breath, I double-downed on my efforts and slurped louder.

"Norm", Darnel turned on him, making him jump. "Has your sister got any more toys?"

Taken aback, Norm nodded slowly.

"Go get them."

Norm scurried from the room, quite excited. Darnel looked back on my, smiling. His smile quickly faded as he snapped at me "Stop looking at me whilst you do that," he said.

"Bill," he called over to the now-completely-silent-BIll almost cowering in the corner.

Quickly Bill jumped up: "Yes?"

"Get me a blindfold".

It wasn't long before my vision was covered and I was being force-fed rubber cock.

Why as Darnel doing this? He knew I wasn't racist... I'd ask him, but I was unable to say anything whilst choking on the toy.

Suddenly Darnel's onslaught quickened and he began to go deeper. Once again I found myself without air and I began to panic.

I started to struggle with my arms to no avail, all sound became muted as I flailed helplessly.

In an instant, the dildo was pulled from my mouth and I let in a grateful gulp of air, only to feel my mouth be replaced by other much smaller dildo. This one was less rubbery and instead taste of salt.

Despite having my mouth filled once again with another toy, I could feel myself breath.

"What do you say?" Darnel posed the question loudly, so that I could hear it over my own heartbeat thundering through my ears.

"Thmck yynoo" I mumbled.

"Good slut", Darnel went back.

I ensured another 5 minutes of throat fucking, all the while with muted noises sounding out from all around me. I heard the sound of Bill and Norm, but got nothing except grunts.

"Now?" I heard Darnel say from on top of me. "OK, do it."

I felt a warm jet hit the back of my throat as the blindfold was torn from my face.

The light blinding me, I looked up to see Norm's face contorted as he came into my mouth. Also looming over me was bill, now also letting ropes of cum cascade over my shirt.

Darnel looked triumphant sitting on top of me. I looked down to see him too playing with his cock as he watched my friends defile me.

With one last grunt from Norm, he fell backwards onto the floor, utterly spent. I coughed-up what cum was left in my throat, but I had already instinctively swallowed most of it down.

Bill too sat down. Unlike Norm, he still had his shirt on.

I looked up, speechless to Darnel. He smiled back down at me, biting his lip.

"OK sissy, it's been decided," he started. "You're going to be our date."

I looked around at all of them, Norm and Bill conked-out after their most recent orgasms.

As I spoke, I felt my throat dry and raspy. My lips spluttered over the cum still in my mouth: "All of your dates?"

He smiled back down at me menacingly. "All of our dates".

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AnonymousAnonymousover 1 year ago

Ughhh this is so hot bruh fucking hot loved this good ass job

AnonymousAnonymousover 1 year ago

Amazing start please keep

It up!

JD2100JD2100over 1 year ago

so hot i can't wait to see the next chapter.

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