The Penalty

The realization that really struck home was that despite all of those many slights, the pattern of the relationship, I had just accepted all of it. I had accepted it because Jeremy was the type of guy who pushed boundaries and I was the guy who let my boundaries get pushed. Thinking further, I could even picture the moment when Jeremy told Brian about me, his former roommate. Not gay or effeminate in the slightest, but a total pushover they could mold into whatever they wanted. Maybe he felt bad about it, and wore a hangdog expression on his face while he sold me out, or maybe he didn't and instead wore a self satisfied grin at the idea of me becoming a sissy gangbang slut. Either way, and this was the final realization, the final hammerdrop on my addlepated brain, I still couldn't muster the strength to even be mad at him. I looked back up at Allie, who allegedly had been a guy like me not too long ago, and was now a slutty bottle blonde grinding on a stranger.

"Are you happy?" The question tumbled out of my mouth in a soft slur. I blinked in surprise. I hadn't known that was what I wanted to ask her until I heard the words.

Allie pursed her lips, and shifted her position on top of me before answering a few moments later. "Like anything, it depends on the day I suppose. Before last January I was a low level sales associate with a mountain of student debt and a long bleak road of empty corporate striving ahead of me. I didn't have any long term ambitions, or short term ambitions, I was just going through the motions. Now I mostly just party and fuck who Brian tells me to fuck." I frowned, and Allie, upon seeing that, put a finger up. "Judging me Chris? Really?"

"I'm just surprised I guess. Paying the Penalty seems to have made a much bigger impact..." It bothered me more than I wanted to admit. By then a good portion of me was leaning towards going through with the penalty but the thought of my entire life becoming about this was daunting.

"Well it did for me, but it doesn't necessarily have to. I enjoyed The Penalty, a lot, and Brian saw an opportunity for both of us to make some money out of the whole thing. It's not like I'm some mindless slave or anything, I'm just a girl trying to have some fun and make some money. A couple of big events with Brian and his friends earned me enough to pay off my student debt, and now I've built up enough savings that I can begin to contemplate making some other life moves. Going back to school or buying a house. Do I love everything I've done over the past year? Nah, there are some gross ass dudes out there, and sex work IS work after all, but on balance? Yeah I'm alright." She paused, and pinned me with a quizzical glance. "But I think we're talking about the wrong topic entirely. This isn't about me at the end of the day, it's about you."

Allie leaned forward until she was centimeters in front of my face, and asked, in an intense and sultry little whisper. "Tell me Chris, and be so honest with me: when you jerked off to all that slutty sissy content that the guys sent you, did you ever, even just for a moment imagine that it was you in my place?"

The question hung in the air for several moments. Allie was still on top of me, still pressed against my cock, and with the X now fully active and coursing through my bloodstream, every point of contract was a tingly electric explosion. I closed my eyes, took a deep breath, and then told her the truth.

"Yes." That one word was enough to elicit an excited squeal from Allie, who grabbed my face and kissed me desperately. It was the truth. Maybe for just fleeting seconds here and there while I admired Allie's slutty form being used, contemplated and then discarded because it was so far outside of my ken. Those fleeting seconds had been looming ever larger and larger in my mind ever since Brian had revealed what The Penalty was. They loomed so large at that moment that I did not resist as Allie leapt to her feet, took my hand in hers, and dragged me away to her private bathroom.

I wish I remembered more of the hour that followed. It was probably the single most transformative hour my entire life, incredibly significant even amongst the collection of incredibly significant hours of that day, but between the alcohol, which there was more of during that hour, and the pot, which there was more of during that hour, and the X, which remained pulsing through my bloodstream reducing my experience down to a series of full body sensations, that hour is by and large gone. I remember creams and razors, lotions, and make-up, I remember that Allie punctuated each step with some of the most beautifully lurid dirty talk I'd ever heard up to that point, telling me as she shaved my legs, or waxed my asshole or perfected the lipstick on my already full and feminine lips how each one of my holes was going to be an instrument of pleasure, how my lips were going to look exquisite wrapped around Jeremy's cock, how Brian was going to fuck my slutty ass until I coudn't walk. My body responded to each and every single one of her direly sexy warnings and by the time she was done with me a final ingredient had been added to the cocktail that made me an ideal gangbang slut for the night: I was recklessly, desperately horny.

I remember looking into the mirror in Allie's room when she instructed me to, and being blown away. The man I had been when I came to the house earlier that day was gone, replaced by...well the words 'sex kitten' come to mind. She had fitted me with an elegant blonde wig and done up my makeup to rival any fashion model. She had dressed me in an outfit that screamed 'fuck me!': an artfully padded sleeveless halter top in which my always too skinny arms and shoulders were now enticingly feminine. A leather skirt came next, and fishnet stockings which were topped by a thong that had a pouch in which my manhood was now carefully tucked away. "Wow." I remember that word escaping my lips, as my mouth sat agape and a trembling hand reached forward to touch the strange and fascinating reflection that I saw. Allie only giggled in delight, coming up behind me and planting a sensual kiss on my neck that had my whole body shuddering once more, before resting her jaw on my shoulder.

"Mmm, yeah" She said, her voice soft and slurred herself. "I do fucking great work, don't I?" I could only nod in agreement. "Come on." She continued, casting a look at the electric alarm clock on her bedside table, "Let's go, I think the final game has already started." With that she led me back downstairs and brought me before the rest of the league.

It quickly became clear that in the hundred odd minutes Allie and I had been upstairs the rest of the league had been hard at work partying. They were louder than ever, hooting and hollering at a level that could be easily heard before we had even hit the stairs. When we actually entered the room however, an eerie quiet immediately set in, and I was distinctly aware of eleven sets of eyes boring into me. Seating arrangements in the room had changed, with Brian and Jeremy, the two finalists sitting on the same center couch that Allie and I had occupied earlier and the rest of the league sitting in other couches and chairs surrounding them. Brian let out an appreciative whistle as soon as he saw me, and he beckoned Allie and I to approach him. I stood in front of him and Jeremy, my hands clasped behind my back and my head tucked down in coquettish shyness. Brian was having none of that. He reached out to grasp my chin and yanked it up to see my face. He whistled again.

"Goddamn, Allie, you did a damn good job here. Maybe the best we've seen yet. Turn around for me sweetheart." It took me a second to realize that the last sentence was addressed to me. Nobody in my entire life had called me sweetheart, and certainly not in that tone, which spoke to both possessiveness and desire. I felt myself flush as I obeyed, spinning slowly in front of the two men, and when I felt a large hand reach out and grope at my thong covered ass as I presented it to them the squeak that emanated from my lips was high pitched and felt disconnected from anything I recognized. Brian laughed at my surprise as I finished my turn and faced them once again. "Oh yeah, a real good job. You're one hot little slut, aren't you?" It felt like a question aimed at me, but instead of waiting for an answer Brian kept on speaking. "Isn't she a hot little slut, Jeremy?" I subconsciously licked my lips as I turned to look at Jeremy. The picture I had seen of his cock just an hour ago still blazed in my mind, kept there by Allie frequently mentioning it as she conducted my makeover.

Jeremy had been quiet since I entered the room, but as I met his eyes the desire I found there was enough to make my knees knock. He was staring at me like a starving man looking at a steak dinner, a man in the desert at an oasis, like a man who...well like a man looking at a hot little slut he was desperate to fuck. His response to Brian was a simple word, soft but with a visceral edge to it that had me shuttering and Brian smirking. "Yeah."

"Well sluts, don't just stand there looking pretty. You have some hungry and thirsty men here and still two quarters of NFL action before we find out who owns your little cock hungry asses for the night!" That declaration from Brian finally broke the quiet of the room as he was met with a loud whooping from the rest of the room. I could see Allie roll her eyes as she led me away and to the kitchens, where we gathered up trays of snacks and drinks. All the men in the other room had been perfectly capable of getting their own refreshments a few hours ago, but this pantomime of servitude was apparently part of The Penalty ritual. Or, as Allie put it to me in a dry tone accompanied by another eye roll, 'just some power trip shit.'

After we had returned to the main room and dispersed all the snacks, dealing with several of the guys reaching out and groping at us as we did so, I returned to Brian and Jeremy. Brian was preoccupied, one eye seemingly on his phone and the other on the screen. Jeremy seemed more relaxed, lounging with two hands behind his head, staring at the TV with a smile on his face. It took a moment for Brian to realize I was there, but once he did he looked at me with a combination of a smirk and a sneer. "Get down bitch, on your knees." He growled at me. I looked at him quizzically, genuinely unsure of what he meant. "You're going to be the property of one of us in a little bit, you might as well get used to your place." He growled again, and then reached out a large hand to my shoulder and pushed me down. I ended up in a kneeling position on the floor between the two prospective fantasy champions, watching the television intently as the final quarter of the fantasy season played out.

I obviously by this point had a clear rooting interest. Allie had tempted me earlier by showing me that picture of Jeremy's cock, and as I sat on the floor mere inches aways from his crotch it was all I could think of. Brian was clearly sweating the result too, knocking back drinks while looking constantly at his phone. Occasionally he would reach down and grope at my well padded top, and mutter about how he was going to wreck my ass. After each time he did this, Jeremy would respond with a silent reassuring pat on my shoulder.

As we watched, the stakes of the contest soon became clear: Brian had his quarterback playing, and struggling, while Jeremy was ahead and had his tight end (the football position, get your mind out of the gutter) in the game. Brian crowed in pleasure as his quarterback threw a touchdown pass with five minutes left to play, while Jeremy's hand on my shoulder shifted from reassuring pat to a nervous grip. On the ensuing drive, Jeremy's tight end made a diving catch for twenty yards that had Brian cursing again, but that was all that team was able to accomplish before being forced to punt. The general raucousness of the rest of the league had quieted down once again, as everybody turned their rapt attention to the television screen for what would probably be the final drive of the game. Brian's quarterback handed the ball off to his running back for the first two plays, causing Brian to mutter angrily while leaving the team in a third and seven situation. On the next play the quarterback dropped back, was flushed out of the pocket to his right, and unfurled a pass deep across the field to the left. It hung in the air for several heart pounding seconds as it spiraled its way to a trio of players, the entire room so quiet for those seconds you could hear a pin drop, and then at the last possible second a player from the opposition team jumped in front of the intended receiver and secured the interception.

The crowd on the television exploded, the announcers of the game exploded, the rest of the league exploded too, several of them jumping up and rushing over to the couch to slap Jeremy on the shoulder or shout something rude to Brian. Brian and Jeremy for their part were quiet. Brian was fuming, staring at his phone with a deep set scowl that marred his otherwise handsome face. Jeremy on the other hand was staring directly at me again. I, still on my knees, looked up at him, that simple act and posture making me feel so very submissive. Jeremy hesitated for a second, and then he leaned down and captured my mouth in a kiss. It was my first time kissing a man, and immediately I was lost, as his tongue plunged into my mouth and his hand grasped the side of my head possessively. Our kiss garnered more loud cheers from the rest of the group, along with joyful shouts of "PEN-AL-TY!" "PEN-AL-TY!"

"Well, you hear the people." Jeremy said quietly after he broke our kiss, but his eyes held a question in them, as if seeking a final absolute confirmation that this is what I wanted. I didn't respond verbally, between the drugs and alcohol and the urgent stirring in my groin, my words weren't flowing naturally. I did reach out a hand and pat his crotch, feeling the massive piece of flesh that I knew lay there. I tried to seem more confident than I really felt as I shifted position and unzipped his pants. Suddenly the picture I had been fantasizing about for over an hour (had it only been an hour?) was right in front of my face. Eight inches long and as thick as a beer bottle I licked my lips reflexively, but at the last second I hesitated.

"Just kiss it." A whisper came from inches away. I turned and saw that in my distraction Allie had joined me and was now also on her knees in front of Jeremy. I did as she instructed, peppering the bulbous head of Jeremy's cock with soft kisses. "Good girl." Allie said affirmingly. "Now lick it." I complied again, licking from the base of his shaft all the up to the tip. "Mm, yeah that's right. Now suck it slut. Worship it." After taking one last deep breath I obeyed, plunging my head down on to the thick member in front of me. I operated mostly on instinct, and memories from not enough experiences, but I knew to keep my teeth out of the way and I was an enthusiastic amateur, bobbing and stroking and licking and sucking.

While I was hard at work pleasuring Jeremy in front of a rapturous audience of eleven other men, Allie was not idle. I was soon aware of my skirt being pulled up and my thong being pulled aside, the sudden presence of a cold liquid dripping onto my asshole, and then a skinny finger pushing its way inside. I was so surprised at this intrusion that I lost my pace and stopped sucking for a moment, but Jeremy was having none of it. He grasped my face in both hands and began to thrust away at my mouth while I was lost in the sensation of first one, then two, and finally three fingers sawing away at my virgin ass. I had only just gotten used to the sensation when Jeremy paused in his assault on my mouth.

"I don't want to cum in her mouth." He said, but not to me. "Is her ass ready?" The fact that he wasn't asking me but rather Allie if he could go ahead and fuck me turned me on to an insane degree. She must have nodded her assent because a second later he stood up and a few seconds after that I felt the tip of his massive cock poking at my tightest entrance. Jeremy did not take his time. A few seconds later my entire body was screaming at me in pain as eight inches of steel hard flesh slammed into me. I howled and tried to buck away, but Jeremy was implacable as he withdrew his rod and thrust it back in again. Out and in, out and in, lighting fast and spurred on by more cheers and the constant chorus of "PEN-AL-TY! PEN-AL-TY!".

In those first few minutes, even through the morass of substances I felt a sinking regret as the pain mounted and mounted. As that sensation reached a peak however, and I felt like I was going to pass out from the pain, a strange thing happened: the pain faded, replaced by a churning sensation in my groin as Jeremy's cock made contact with spots in my body that nothing had ever made contact with before. A few seconds after that I found myself humping my ass back towards him seeking more of that sensation. The crowd cheered even more upon seeing that, with catcalls of "SLUT!" and "LOOK AT THAT COCK WHORE GO!" joining the chorus.

While Jeremy continued to hammer away at my virgin ass, Brian had apparently noticed that I had an unoccupied hole. I heard him unbuckling his pants and a moment later I was presented with another long thick cock in front of my face. This time I did not need any coaching from Allie as I leaned forward to capture Brian's cock in my mouth. "Good girl." He purred to me as five inches of him slid into my mouth. Then I felt his hands gather up handfuls of the wig I was wearing, formed into handlebars for him to fuck my face. Suddenly then I was no longer a full thinking, acting body. I was cock sleeve, a double ended fleshlight with two huge cocks buried in me. I was starting to zone out, lost in the novel sensations, when I felt a sharp crack of pain on my face. "Look at me while you're blowing me, slut." Brian commanded cooly, while continued to fuck away at my mouth. "God you really did turn out perfect. Jeremy was right."

My eyes widened in surprise. I had already figured out that Jeremy had suggested me, of course, but I was bewildered that Brian was bringing it up while I was in the middle of being spitroasted. Brian misread my expression, and let out a laugh mixed with a groan of pleasure at my sucking. "Oh yeah, your friend sold you out." He grunted the words out. "And let me tell you slut, you actually had him pretty nervous. Usually when we pick a prospective sissy, they show up with no fucking idea how to play the game. It's the easiest thing in the world to just let things play out. You put in so damn much prep work that Jeremy approached me on the very first day, at the Draft, telling me we would have to go the extra step with you." That did surprise me, my eyes widened again and I tried to turn around and look at Jeremy, but Brian kept his grip on my head. "Messing with someone's first draft pick, we've pulled that move before, but you? Probably six different times your new daddy was blowing up my phone suggesting fucky things to do to make sure you'd end up right where you are. So congratulations, Jeremy, you won. You won the trophy, and you won the little fuck slut. Congratulations Chrissy, you were set up from the beginning."

All throughout Brian's little speech Jeremy had continued to fuck me, pistoning into my ass at a frenzied pace, not altered at all as we both listened to Brian talk. As soon as Brian had finished speaking, Jeremy approached his first climax of the night and he grabbed my hips and held me close as I felt his cock pulse inside the vice grip of his ass, depositing spurt after spurt of cum into me. Then he withdrew and I was suddenly, shockingly empty, my now gaping asshole contracting. Brian also approached his climax, grabbing my head and forcing it even deeper onto his shaft, ignoring my loud gags as he also deposited load after load of cum down my throat.