The Penalty

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The moment that Brian and Jeremy both withdrew from me seemed to be a cue for the rest of the guys present, as they immediately started to push forward from the periphery of the room. Just as I was about to be beset by a horde of horny men though, Jeremy raised a hand and signaled them to wait. I was on my knees, breathing hard when Jeremy reached down and pulled me around to face him. Jeremy is a big guy, six foot three and two hundred twenty pounds of well honed muscle. I'd always known he was a big guy but until he stood looming over me that afternoon I had never really felt the difference in our sizes. As I looked up at him I was shocked to see a look of absolute contempt etched across his features. I opened my mouth to speak, but he raised another hand, cutting me off.

"Look at you, 'Chris'. You're on your fucking knees, both holes filled with cum, ready to be gangfucked by another eleven dudes. Is that a fucking guy to you?" Jeremy shook his head, impatience washing over his features. "When we lived together it took me all of two weeks to turn you into my goddamn maid. I fucked pretty much every girl you were ever interested in while we were under the same roof. Is that a guy to you? I always knew you were a little beta, but when you turned up here in town all down and lonely my heart fucking broke for you. There's a reason why you could never find a girl, or find a group of guys to hang with: you're not supposed to be a guy! So yeah, I set you up. I gave your name to Brian, I told him to press the right buttons to get you here. I did it for you. And lets be clear, you've had every opportunity to walk the fuck out of here, but you haven't, have you? You're still here. Maybe it's the money you want, or just the hard cocks. Either way you're a whore or a slut." Then Jeremy stepped towards me and raised his hand a third time, so rapidly that I flinched back. Instead of striking me though, Jeremy brought his hand to my face, dripping with saliva from the back to back face fuckings I'd received, and caressed me. When he spoke again his voice was infinitely softer and gentler.

"Look at you, Chrissy. You're such a hot little slut. You're fucking made for this girl, and if you want you'll never have to be lonely again. I can take care of you, like Brian does Allie. Think about it." Then he stepped back and motioned to the rest of the guys in the room, and after that I did very little thinking about anything for the next while.

This is another section of the night where my memory fails. Fortunately for this part of my story there is photographic and film evidence surreptitiously recorded by Brian. I've watched the videos and looked at the pictures many times since then, and every time it felt like I was watching a completely separate person from myself. The person in those videos is a cock hungry sissy slut. Watch her there, desperately trying to suck three guys at the same time, mouth and hands a constant flurry of service and pleasure. Watch her here, getting spitroasted by two guys while another two guys stand by and slap at her face with their hard cocks. Watch her bouncing on a huge black cock, her own raging erection betraying how much she absolutely loves what she is doing. Watch how the BBC inside her finds just the right spot at just the right speed, and see her explode, cumming all over her own chest without anybody touching her. Watch her in the aftermath, her face a plaster mask of cum, her asshole a gaping wreck. Watch the other girl in the room, her guide in the ways of sissydom approach and whip out her own girl dick. The gangbang slut is tired, drained, worn out, the X starting to wear off and a hangover approaching, but she sees the girl dick in front of her face and, in what is already starting to be a bedrock instinct, she sucks it off. For this sissy slut, being tired doesn't matter when there's another cock to service.

I've watched that video so many times and I only have vague snatches of memories. I think back and I only recall scattered peaks of sensation, high points on a tide of submissive oblivion. I remember lying curled up on the couch in the tattered remains of my outfit, wig askew and spent cock poking out of my thong. Almost all of the guys had left at this point, there was just me on the couch and Allie sitting on a recliner in Brian's lap, both of them dozing off. Jeremy approached me then, and that is my strongest memory. I looked and felt like a disgusting mess, like a used up fucktoy ready to be discarded. As Jeremy shook me awake though, the expression on his face wasn't the contempt he'd shown me earlier or the feigned pity he'd shown me throughout the past sixteen weeks, it was clear genuine admiration. At first I thought he wanted to use me again, but as I was beyond spent I put out a hand and shrinked away from him. He just laughed and shook his head, before reaching for his wallet and pulling out a thick wad of cash. "For you, milady. For a job excellently done." He placed the cash on the side table next to the couch and turned to walk away.

Fantasy Football always comes to chance. We do the research, listen to the analysts, but we ultimately leave it all up to strangers. It turns out that my experience had not been up to chance, not really, but as I lay on the couch, my tired mind turning slowly over what Jeremy had said to me earlier, I realized that it could still be up to choice. I spoke, a single word forced out of my very strained throat. "Wait." Jeremy stopped, waiting, so I spoke again. "I thought you said I wouldn't be alone." Jeremy turned back around, examined my face and then laughed, a genuine bright bark of delight. He stepped back to the couch, went to pick me up, but then he paused, a bright glint passing through his eyes.

"You won't be alone," He said, "But that doesn't mean there's going to be a free ride. You'll have to earn your keep. Some more events like this maybe."

From the recliner where he had been dozing off, Brian stirred and called out, his voice sleep clouded but very amused, "Having a girl like Chrissy can be very useful for a career in sales." Allie stirred too then and playfully slapped Brian on the shoulder.

Jeremy for his part continued to look at me, one eye cocked in an unspoken question, waiting for me to respond. I was tired, I was wrecked, I had just quintupled my lifetime number of sexual partners in a single afternoon, but despite all that the thought of being Jeremy's live-in whore caused one more stirring in my spent cock. I let out an exaggerated sigh and then I nodded to Jeremy. In response he let out a bright delighted laugh before picking me up in his arms and carrying me bridal style out to his car, and towards my new life.

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AnonymousAnonymous2 months ago

A very interesting story. I couldn't have been in it but it's an interesting story. And I definitely couldn't have been so blase about the whole situation at the end. Maybe it's the fact that I spend way too much money on fantasy football to allow something like that to slide. Maybe it's The minute they rig the game for me to lose I don't care how big they are they'd caught my hands. Or they each would have mysteriously been attacked and kneecapped in the following weeks. But good story very well written

SissyBoy1WarszawaSissyBoy1Warszawa3 months ago

A great story showing personalities that are like fire and water, like two different shores... from an ordinary boy to submission and passing as a servant to becoming a sissy used by a dozen or so men. You wonderfully showed mentality, emotions and, to a large extent, mental and physical dependence on dominant people. I like Chris/Chrissy very much and I even got close to him and I would like to become a sissy like him/her. I hope you will write more about Chris/Chrissy and what happened to her/him? How did he/she serve Jeremy and what sexual experiences did he/she experience?

ps. Sorry for any errors and linguistic inaccuracies, I don't speak English.

Best regards, SissyBoy from Warsaw, Poland. 🧒🏻⚧️👧🏻❤️👱🏻‍♂️🧑🏻💦👅🥛🍦🍼💋💦👨🏻🧑🏻👨🏻‍🦱

donaldelliott11donaldelliott113 months ago

I love the premise. I also enjoyed https://www.literotica.com/s/the-punishment-40

latinarita4latinarita43 months ago

Immediately my new favorite story on literotica

Literally one of the all-time greats

This was...unparalleled

Not just the development, not just the story, not just the inner-workings of the mind

It was this line that showed me you are the top writer: "high points on a tide of submissive oblivion"

This story deserves a sequel...nay an entire series! a whole book!

please continue this!!!!! i beg of you!!!

AnonymousAnonymous3 months ago

As much as I love being the slut I can be, I have to say this. These guys would have to worry about going to sleep

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