Halloween Slut

By Amie Doucet

Published on Sep 12, 2023

Transgender

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+++++

This chapter begins with a cock in my mouth.

A fat, ginger cock, and a message from an old compatriot of mine flashed in my face:

"keep him there. I wanna fuck that bitch in the ass."

I thought about what that meant to me. The man who sent it, Jesse Winkler, bullied me when we were in high school. He saw me as vulnerable. I wasn't the lowest on the totem pole, so I let him go after weaker subjects just so his time would be taken up and he wouldn't be able to get to me.

But in a way, I'd been waiting for this all my life. Jesse Winkler was my superior. He knew it. That's why he bullied me. And I knew it. That's why I accepted his bullying.

Now he knew I had chosen to show my inferiority to him. Now he knew that I took dick in my mouth, and in my ass. He could exert himself upon me if he wanted.

Did I want it too?

A deep and dark place in me--a scary place--knew that the answer was 'yes.'

But most of me thought that he was coming here just to humiliate me.

Would I allow it to happen? Could I prevent it if I tried?

Meanwhile, my head is moving up-and-down on this idiot Gavin's cock. I slurped on his dick. I'm out of control of the situation. I've put myself here. I'm dressed like a fucking slut. I'm shaved, perfumed, and made up, all so I can suck on the cocks of my maybe-boyfriend Brendan's friends, who are not my friends at all.

If I have any pride at all, I'm not demonstrating it now.

Gavin was making a show of taking that pride from me.

"Brendan, you should make this one get tits."

"Yeah, that worked out so well last time."

That was Dominic. It was a clue. Had Brendan forced another CD to suck these guys' dicks? Had she gotten a set of breasts? That's what it sounded like. Made me just a twinge jealous. Well, she wasn't here blowing these guys--I was.

As I sorted through this intel, I focused on what I wanted--to get this man to blow his load inside my mouth.

I used my tongue, my lips, and the tension in my jaw, to make it feel like Gavin was fucking the tightest pussy of his life. The most responsive. The most attuned.

He began to breathe deeper. He was in less control of his body.

I went harder after him. The desensitization training was working: I could take his cock to the hilt. And I did, thrust after thrust.

His hips did this cute little pump just as I got him near the depths of my throat. I thought that he probably was not a very good fuck--he just did not put much into it from his side.

That's fine. I don't mind doing the work.

I'm getting pretty good at it.

Gavin seemed to agree.

"Oh... fuck..."

His big dick began to tense even more. I felt like I was throating a fat cucumber, shiny and taut, thick and fat, and about to burst.

And burst he did... right into my throat. He pulled a last one of his cute little thrusts, pointed it straight down my throat and shot a wad of semen. Probably shot another one, maybe two, before he pulled back into my mouth.

By then, I could taste his load. It was grosser than Dominic's or Brendan's... like it had been kept in a gym sock for a week before it splooged in my mouth.

Still, it was the essence of a man, and I realized that I now love to receive that in my mouth.

His load was huge. I knew based on how much cum I swallowed, but also by his face, that I had floored him. I had given a better blowjob than any bitch had before.

Who knows? It might have helped that he knew I was a faggot, a bitch he had just set up for the assfucking of a lifetime. I can't know what was going on his head. But that might have turned him on too.

Either way, by the time Gavin finished blowing his load in my mouth, he was basically knocked out as fuck.

I leaned back, wiped my lips with the back of my hand, swallowed what cum was still in my mouth.

Dominic and Brendan laughed good-naturedly at how knocked out their friend appeared. "What do you think, brother? Is she worth keeping?"

Gavin was so knocked out he couldn't even reply. He had his forearm over his eyes to protect him from any sensory input at all.

"Let's get some fucking dinner, fam. Some Lebanese. Or Thai, if that's what sounds good."

That was Dominic. He was still the coolest of these three.

They sorted out where to go. I got to my feet, started to get dressed so I could join them.

"The fuck you think you're going?"

That was Brendan, my probably-not-actually-my-boyfriend.

"Uh. I thought I'd come with you to dinner."

"You look like a fucking tranny slut. You think you're going to sit with us for dinner? Sit and wait. Maybe we'll bring something back for you. If you're good."

I sat back down on the floor on top of my platform heels.

"Oh, and don't put on your clothes--you'll be back in your panties in 45 minutes."

The boys had a laugh, got their shit together, and left. They locked up.

I was alone.

+++++

Whatever. Those dicks left me behind. Starving and dressed like a slut. Nervously waiting for the arrival of her high school bully--the one who just discovered she's a crossdressing fag.

For five, maybe ten minutes, I sat right there on the floor. Like an obedient dog.

Then curiosity got the better of me. Like a cat.

Meow.

I looked at Dominic's desk, covered in random bills, notes, to-do lists, receipts. It was such a boy's desk.

I flipped through some of it. Ah! An envelope from the Georgetown alumni association. I figured that Brendan had gone to Georgetown with Jesse. They all seemed to act like college buds.

The rest of it was boring. I didn't need to know that Dominic ate at Carl's Jr. last night, but now I did. Wonderful.

Then, fuck... I found his laptop, buried beneath all the papers.

Do I look at it?

If I got caught, it would mean hell to pay. It might mean physical violence. I didn't think these guys would kill me, but the fact that I had to ask myself that question might tell you how little I knew about the situation I was in.

The feline impulse in me was too strong.

Besides, he'd probably have a password, right? Everybody has a password these days.

Except... he didn't.

On Dominic's screen, his email program was wide open. I scanned for Brendan's name.

There it was. Brendan Rogers. Rogers. I knew his name now.

I read a couple of messages. Just boring, bro stuff. Some inside jokes. Double entendres. References to pussies they'd just fucked. Sports games they'd just watched.

One caught my eye. The subject... "re: new bitch."

Fuck... that was me.

There were six recipients, so seven people in total on the message chain.

And there was a photo. Of me, with my lips wrapped around Brendan's cock, and a look in my eye that says, "this is exactly what I want to be doing right now."

The other guys, i.e. the four that were NOT here tonight, seemed to live elsewhere. But they were definitely interested in fucking me.

Brendan threw out a possibility. "Why don't we meet in Vegas? We can bring our bitches. It'll be a proper gangbang. They might even like watching each other get fucked."

I guess I'm going to Vegas soon.

I heard some noise from the front sidewalk. I scrambled to close the laptop, cover it up with all the paper, and get back onto my knees.

As I did, I found myself in a position of extreme longing. I could feel a slight pain in my knees, but I felt even more than that a desire to be in that position. I had learned a little bit about my captors, if I can call them that, but nothing that did not make me want to be here less. In fact, I wanted to be here even more now--in this vulnerable position, ready to be violated however they wanted to violate me.

The boys were loud as they came up the stairs.

I heard a new voice.

Jesse was here.

Dominic opened the door, but Jesse was first through it.

He strode in. He didn't take off his sneakers, or anything. He looked... good, I have to say. Designer jeans. A t-shirt that showed his muscular chest. He's been working out since high school, I thought.

He stood directly in front of me. I looked up into his eyes.

"Look at you. Aren't you cute?"

I didn't know what to say to that.

"Man I wish I had known you were a faggot back in high school. We had tons of fun with Andy. He was a real pussy. But look at yourself. My god. I'm not sure if I've ever seen a bigger sissy faggot than you right now."

I let him continue. I just stared plaintively at him.

"Andy... now that kid was almost too much. He was so horny, we'd fuck him every day after practice. Kid couldn't get enough. I must have blown 100 loads in his mouth, and just as many up his asshole.

"You two faggots ever get together?"

I kept staring up at him. I somehow did not know how to speak.

"I said, Did you two faggots ever get together??"

I shook my head.

"Figures. You'd have a hard time figuring out who was going to fuck who. He was a little bottom bitch just like you."

I nodded slightly.

"So. What you want to do? You want to be my little bottom bitch? Jeremy, the cute little faggot doubles player?"

I nodded again, slightly.

"I wanna hear you say it."

I found my voice. Just in time to say something I never would have dreamed I'd say to my high school bully.

"I want you to fuck me. Up the ass. I want to take your whole big dick up inside me. I want to make you feel great. And I want you to pump your whole self in me until you shoot your load inside my ass."

"Wow. You're well trained. Well, I'm gonna. But there are just a few things left to discuss. Two notes, really.

"One, it's not your ass--it's your pussy. Practice that."

I nodded.

"No, SAY it."

"I want you to... fuck my pussy."

"Perfect. Second, isn't there a step before the fucking? Don't you want to get me hard first?"

"Yes, I'm sorry, Jesse."

He slapped me down my face. It didn't hurt too bad but it was embarrassing. The guys standing around the room gave a chuckle.

"Don't EVER refer to me by name. To you I am 'SIR' only. Now practice that."

"I'm sorry, sir. Before you fuck... my pussy, I want to take you into my mouth. I want to make you feel amazing. So that you're hard enough to pound my pussy."

"Very good. Take off my jeans."

I began to reach up for his black leather belt.

"Uh uh. I did not say you could use your hands."

I pulled my hands back to my thighs. I kept looking up at him. I gently used my teeth to free his belt. It took me thirty seconds to pull it all the way out. His friends tittered.

Now the button at his tight waist. Of course it had to be a button fly rather than a snap. I nipped at the fabric. Finally I got a hold. Then I tugged at it like a dog to get it free of the button.

This was torture.

Finally, I unzipped his pants, the zipper grazing the tip of my nose as I slid it down. His jeans were so well-fitted I had to pull them down with my teeth too.

He stepped out of the jeans and patted me on the head. "Good girl."

Under his jeans he had on a pair of dark green briefs. I don't know why it did not surprise me that he wore briefs. He was the guy who was so masculine he could pull them off.

I had an instinct, one I wish I didn't have, and I acted on it. I buried my nose and face into the side of his bush so that his cock and balls rested on my face through the underwear. I inhaled deeply through my nose to take in his essence.

"What a fuckin' slut, Brendan."

I think Jesse was truly surprised. Or impressed. Or disgusted.

I nodded a bit more deeply as I pulled the top of his briefs down with my teeth. As I dragged them down over his legs, the length of his hardening eight-inch cock dragged down across my face. He was dripping precum. It painted a line from my forehead to my chin.

"OK, baby, it's showtime."

It sure was.

Jesse's cock was straight as an arrow. It reminded me of cocks I'd seen on some Reddit forum for dudes with big dicks. I thought for a second about how much I'd changed in the past few weeks. That I would surf for "dudes with big dicks" online was new. A month ago, I would never have imagined it. Now I could compare Jesse's fat cock with a half dozen I'd seen (and worshipped) online.

I surrendered fully to Jesse, to this moment. I looked up at his face as I licked him from base to tip, carefully wetting his underside with my saliva, telling him with no words that I would take care of his cock the best way I knew how.

"Oh, you're fucking slutty too, huh?"

I took that as approval. I moved my tongue around the outside of his head. I licked the glans with just the soft wet tip of my tongue, let it bounce there once, twice. Then I plunged my mouth down onto his cock, taking it as deep as I could.

I wish I could say I could swallow the whole thing in a go. I could not. Eight inches is a lot, folks. But I got deep enough that I could smell the sweat in Jesse's pubes. The scent was familiar. Jock sweat. Alpha man. Deep masculinity. Sweet, and ripe, and as sexy as anything I had ever smelled.

I was in love.

With my bully's cock.

"Oh... fuck yeah, baby."

I started to work his dick harder. One thing you cocksuckers might not know? Pay attention to what your tongue is doing. It's not just about the thrusts--it's about what's happening while he is thrusting. I made love with Jesse's dick each time it slid into my mouth. I couldn't afford not to. I needed to give him the best blowjob he's ever gotten.

Maybe I'm a perfectionist. Maybe I'm a hardcore cocksucker. It's likely that I'm both.

Just as I got into a rhythm, he pulled my head off of him with two hands.

"Whoa whoa whoa! You trying to make me cum just with your mouth babe? I need to feel this baby all the way inside you. Turn around, spread your legs, and stick your pussy up in the air so I can see it!"

I did as I was told.

My shoulders down, my ass up, and Jesse's dick as hard as a fucking diamond, I waited. Waited for my opportunity to get drilled--hard.

Jesse got down on his knees. He pulled my panties down off my ass, hard. As my panties clenched my knees together, I spread my feet to the side to make room for him. He dropped in and lined up his cock.

"You know, I've been waiting a long time for this, bitch."

He thrust his cock into me.

He didn't wait for me to be ready for him. He didn't think about the fact that a man's anus can take an intruder, but only if it's delivered gradually past the second sphincter.

No, he just railed right on into me.

I moaned out in pain.

The boys laughed.

I sank deeper into pain and self-pity. Jesse's pubes were pressed up against my shaven ass.

"You feel me, Jeremy? That's what it feels like to have a real man up inside your pussy. You like that?"

I knew I needed to respond.

"Uh... huh."

"That's what I thought. Now let's party."

Jesse started his fuck. It began with long, hard thrusts that didn't give me a chance to recover. I would, eventually... but that process would be slowed by how long he was giving it to me now.

I moaned in wounded, animalistic pain. I was non-verbal, to be honest. I clutched onto his dick, squeezed it as best I could in my injured state. I'd been hate-fucked once already today; I don't know if I have a second one in me.

Jesse got into long-dicking me, and the pain began to subside. My verbal skills came back, but only in a basic way: "fuck me daddy, fuck me daddy." That seemed to turn Jesse on.

"You like that, huh? I like giving it to you, baby."

We got into a rhythm together. He would bounce off my ass cheeks. I'd raise my shoulders up just a bit, he'd thrust forward, I'd meet his incoming dick with a big pump of my ass back towards him.

Onward we fucked. It got so hot that the other guys started jerking off.

Somehow, this made sense. My bully was always meant to fuck me. That's what he'd been doing all those years ago--flirting with me so he could fuck me. Now, submissive as I was, I could take it from him.

It was my problem all those years ago. I could have been his sex partner, his toy, his ally, if I had just bent over at the waist, arched my back, and let him fuck me.

Hindsight is 20/20, I guess.

In the meantime, I had business to attend to--namely, making him cum. Inside me.

I continued to bounce back on him. The blowjob I'd given made him as hard and as horny as he'd ever been. I just needed to keep up the momentum.

My mouth did some of the work.

"Oh my god... oh my god... you're fucking HUGE. Oh fuck... fuck... you're so fucking deep inside me! Oh my god... fuck me, Jesse, fuck me!"

I think I did the job. Soon Jesse was thrusting deeper and harder. He was about to cum.

"Get ready for this, bitch! I'm gonna fucking cum... inside your fucking ass..."

Jesse blew his wad while he was thrusting. I could tell from how thick he was that he had lost his load inside me. He thrust four or five more times, then collapsed on my back. He pumped a few more times inside, leaving me plenty full for the evening.

"Fuck... you're one hot fuck, Jeremy."

I took that as the highest praise of the night.

"Excuse me, I just need to freshen up a bit."

The boys let me use the restroom. I thought they might force-fuck me right then. But I think I'd earned a measure of their respect with how well I'd fucked Jesse. And the promise that I'd fuck them the same way about a minute-and-a-half later.

+++++

What do you think? Drop me a line at sexyamie@hotmail.com if you're turned on.

Next: Chapter 9


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