The Penalty

Allie gave me another apologetic look as she rose and went to stand next to Brian, who draped a possessive arm around her as she began to speak. "When Brian first came into this league, The Penalty changed every year. It was normal types of things: 24 hours in a diner, having to chug nasty concoctions, having to wear a chicken suit at the next year's draft, that type of thing." It sounded rather like she was reciting an often repeated presentation. "It was fine, the league was just your typical fantasy football experience, but Brian didn't want a typical fantasy football experience. He wanted commitment from every manager in the league, he wanted excitement, he wanted real stakes. See at that time there were a couple of bottom feeders who didn't even really try to compete each year. They just paid in their minimal dues and showed up to the draft and championship parties to drink and eat for free. Most of all Brian wanted to get rid of those types. Three years after he joined, he finally had a chance to get what he wanted: the old commissioner retired and appointed Brian to replace him. Brian had a devious and pretty out there scheme in mind to change the league, and went about persuading the other members to get on board or drop out. His new idea for the league centered around a new Penalty, The Penalty, a penalty so extreme that whoever paid it would probably never want to play again, and the rest of the league would be so scared of it that they would give the league their all week in and week out." Allie paused, and looked between me and Brian. While she had been speaking Brian's hand had drifted from her shoulder down to her chest, where he was now casually groping her petite tits.

"Don't stop on my account Babe. Keep telling the story." Brian instructed her, without pausing his assault on her chest. I was still pissed and frustrated and now more than a little scared, but I couldn't help but agree with Brian. I wanted to hear the rest.

"The new Penalty, the thing he had to lobby the rest of the league so aggressively for, was that the loser each year would be forced to dress up like a girl, and be...at the disposal of the rest of the league for the night."

Allie's final senstance hung in the air, even as I felt their weight drop on me like an anvil. All of a sudden my mouth felt dry and my fists clenched unconsciously as I struggled to absorb the meaning. Even after several long moments turning the words over in my head all I could manage was a single croak of a word. "What?"

"I'm sorry if this little slut was too delicate in her words." Brian said, his coarse words causing me to involuntarily flinch in place. "What she means is that in a few minutes Allie here is going to lead you upstairs and work her magic. A couple of hours from now you're going to come back down here transformed into a passable looking piece of ass, and then me and Jeremy" He nodded over to Jeremy, who was standing on the far side of the room watching the scene with a slightly pained expression, "And all the rest of the league, are going to fuck you until we are all satisfied." He looked back at me, and then barked out a sharp laugh. "Ah, man, the look on your face. I'll never get tired of it. Allie here had the same look on her face about a year ago when she lost too."

All of a sudden it clicked into place: where I recognized Allie from. I had actually seen her before today, dozens of times in fact. She was the most frequent model in the images my league had bombarded me with. I had most recently seen her bouncing eagerly on a big black cock, presumably belonging to Rick, hanging around in the background of the room, watching the scene play out with an anticipatory smile on his face. My mouth dropped open slightly, causing Brian to laugh again. "Yeah that's right, this hot little slut here used to be a dude like you. We took care of that though, didn't we?" Allie blushed and lowered her head but didn't respond. Brian scowled and I could see his hand tighten in its grip on her breast. "I said, didn't we?"

Finally Allie spoke, just a single word, soft and meek but tinged with an undercurrent of lust that surprised me. "Yes, you did." As she said that, she seemed to sink backwards slightly into Brian's embrace.

"See?" Brian asked me, sounding very pleased with himself. "It's really not so bad. Hey I almost forgot to mention, you will get paid for your services tonight." I tried to muster a response to that, but my mouth felt dry and heavy, so I settled for just blinking at him, eliciting yet another chuckle. "Yeah, our reward structure is a little weird. The champion and the runner up don't actually get any money, they just get first dibs on using your slutty little body. The entire league pot, $1200 dollars, goes straight into your pocket...IF you're a good little girl and play your part."

I swallowed again, still not able to summon any verbal response, but my mind was reeling. Too many big revelations had assaulted me over the past five minutes, but that sum was a concrete thing, a solid figure that flashed bright in my mind. Twelve hundred dollars, two weeks of pay, for a couple of hours of...I shuddered again, but for the first time there was a small sliver of my brain that was open to the possibility. Like a predator sensing the first hint of weakness, Brian pressed his attack, but in an unconventional manner.

"Hey I can see you've got a lot to think about." He said, his tone now back to the friendly and charming salesman patter I had first been introduced to. "The final game won't wrap up for a couple of hours yet, and Jeremy and I both have players involved. Why don't you go upstairs with Allie for a bit. The two of you can talk, chill, whatever. You can decide what you're going to do." Despite the implication of his words, the look in his eyes told a different story. He did not look like there was any doubt about my decision.

Part of me, a large part of me, wanted to bolt from the house right then and there. I felt too hot, and the stares of the other eleven men in the room seemed to be blazing into me like laser beams. A small motion drew my attention to Allie. She had brought her hands together in a pleading motion, her wide face open and disarming. Despite my better judgment I nodded to Brian.

"Excellent." Brian practically purred the word as he released Allison from his possessive grasp. She immediately darted forward and grabbed my hand in her own, pulling me away from the crowd and towards the stairs. As we climbed I could hear Brian say something just barely inaudible to the rest of the room, followed by a wave of very audible raucous laughter.

Allison led me up to her room, a very neat, very feminine space full of pink and flowery accents. Her bed was a massive and luxurious King, and that was where she deposited me. I sat on the edge as I watched her cross to the dresser and start searching through various drawers and cubbies. As I watched I observed her intently. She was wearing a short denim skirt and thigh high boots, and a tight sleeveless tee. Her every movement, even as I examined each one for traces of the man I'd been told she used to be, screamed 'this is a woman!'. Moreover, it screamed 'this is a hot woman!'. How did she end up like this?

I didn't realize I'd spoken that last thought out loud until I saw Allison stop and stiffen, and then suddenly turn to face me. "I ended up like this because I had the...I was going to say misfortune, but I genuinely don't think of it like that. I had the curious fortune to be an intern at Brian's company, for his sales team, the summer before last. I had just finished college and was working for free, for the chance at a permanent position. Um, hold on." She turned back to the dresser and pulled a couple of small baggies from a bottom dresser drawer. As she bent over to fish them out, she gave me a good view of her ass, framed to perfection by a pink thong. I swallowed and averted my eyes even as my cock began to stir in my jeans. "Anyways," she said, as she stood up and crossed the room to sit next to me on the edge of her bed. "I didn't think I was going to get the permanent job, I didn't have that great a time during my internship. A lot of the guys on that team, a lot of them are in this league, but they loved to give me a hard time. I wasn't macho enough, wasn't alpha enough, wasn't into sports and hunting and going out to the bar and getting laid every weekend. Brian at least was nice to me most of the time, he's very good at that you might have noticed." I raised my eyes at her. "He's good at knowing when and how nice to be to people." I thought back to my interactions with the man, all the early red flags that had been smoothed away by his sugared words and charming smile. I nodded.

"Anyway," Allie continued, "I was really surprised that August when Brian approached me and offered me a permanent job as a junior sales associate. He mentioned that he knew there had been tension between me and the rest of the team at times, but, wouldn't you know it, he had a solution." I nodded to myself, more of the pattern now falling into place.

"Let me guess," I murmured, "He suggested you join his fantasy league." Allie broke into a grin as she opened one of her plastic baggies and pulled out two little pills.

"You bet your ass he did." She said, her tone rueful. "That's how this whole thing keeps itself going. Every year, The Penalty must be paid, and so every year he needs to find a new target, someone he thinks has the right..temperament to be what he needs them to be." She popped one of the two pills into her mouth, and dry swallowed it, before screwing up her face in disgust. "Fuck I always forget how nasty this tastes. One second." With that she hopped up fully onto the bed and crawled on all fours to her bedside table, where she snapped up a water bottle and took a big swig. As she crawled I got another good look at her thong clad ass, and my cock gave another twitch. After she had drunk she spun around rapidly. I tried to avert my eyes, but I guess I wasn't quick enough because she let out a little laugh, a devious gaze appearing in her eyes.

"Now, Chris, were you just checking out my ass?" Her voice was mock stern, her eyes were bright and teasing.

"So..sorry." I stammered out. "I just-" I was interrupted by another peal of high pitched laughter from the girl in front of me.

"Relax, I was just teasing you. It's fine. Flattering, even." She said, as she slowly crawled back to the edge of the bed. "In fact," As she retook her perch next to me on the edge of the bed she palmed the second pill. "You want?" She asked, waving it in front of my face.

"I don't know...I'm not.." I was stammering again. All the alcohol I'd had over the course of the afternoon was still swimming around my bloodstream, rendering my thoughts fuzzy. I didn't hate the idea, but I'd never been a drug person. Allie, seeming to sense my hesitation, smiled another devious smile as she placed the pill in her mouth and then grabbed my head, pulling me in for a kiss.

Her lips felt amazing, full and soft and welcoming. Her tongue danced against mine, bringing with it the small foreign object that she pushed onto my tongue. Lost in the thrill of sensation, I swallowed it, and then immediately almost gagged at the foul taste that came with it. I broke away from the kiss. "Sorry about that." Allie said with a laugh. "Here." She handed me her water bottle and I drank deeply, still scowling in displeasure.

"What the hell was that?" I asked.

"Just some X." Allie replied, too casually. "It'll help you relax. It makes this whole thing feel so much better, trust me."

"I still haven't decided that I'm going to do it." I told her, though maybe at that point I was already lying to myself.

"Sure." She said, not sounding convinced. "Anyways, even if you're not going to do it, we can still have fun, can't we?" Her voice was soft and coy and pleading. Before I could respond, Allie shifted and suddenly had gone from perched next to me on the bed to sitting in my lap. "The two of us can have fun." She said again, no longer a question, as her hands found their way to my shoulders and her lips once again pressed against mine. I opened my mouth to the kiss and then a soft push had me laying flat on my back with this beautiful girl on top of me.

She was electric against me, small movements of her hips against my groin causing my cock to spring fully to life, her lips roving along my smooth shaven jaw line and against my neck taking my breath away. My own hands were moving too, sliding behind her to grab at the taut ass I had been admiring, and then coming up to touch the tits that Brian had so possessively groped in front of me. I thought for a second that I had crossed a line, because as soon as I made contact with her breast Allie stiffened, and then straightened back up into a sitting position. "Nah ah ah" She said, as she slapped my hand away from her breasts. "No touching, at least not right now. Let me do the touching." With that she clambored off of my lap and down to the floor, coming to a rest between my knees. Without missing a beat she started to unbuckle my pants and pulled them down, revealing my (perfectly within the average) five and a half erect inches. "Mmm, that's so cute! And it looks so yummy!" Allie exclaimed, before plunging her head down and engulfing all of me into her mouth.

I could count the number of blowjobs I had ever received at that point on one hand, and certainly nobody had ever deepthroated me before. Allie on the other hand devoured me down to the root, causing me to let out a thundering moan. That moan was met by a soft gag, and then Allie released me from her mouth and came back up spitting, with a mildly disgusted look on her face. "Ugh!" she exclaimed. "I hate getting hair in my mouth when I do this." She took my cock into her hand and cocked her head as she looked at it, speculatively, and then her gaze darted back up to meet my eyes. "I'm not pushing you to make a decision on anything, but do you mind if I just clean you up a bit down there? Even if you decide to leave, it will make things feel so much better. Trust me."

I was still on my back, but I propped myself up on my elbows and looked at Allie speculatively. With everything that had happened that day I was on high alert for manipulation, and those alarms were ringing loudly. But my cock was still rock hard and throbbing and slick with her saliva, and her expression radiated nothing but an honest desire to enhance my own sensations. I groaned softly, but I gave in with a minute nod to the young woman in front of me. The sunshine bright grin that I got in return was almost worth it, as Allie jumped up and dashed away into an attached room to the right. I could hear her banging around in there for a couple minutes and then she was back with a rather hefty case in tow.

"Oh, before I begin, here." Allie said, as she grabbed up the other baggy she had gotten from her dresser. A second later she presented me with a thickly rolled joint. "Spark this up." She said, an order rather than a suggestion.

A few moments later acrid weed smoke filled the air and Allie was hard at work. It should have been a weird tense moment, but between the pot, the x, and all the alcohol I had consumed, I felt light and detached from my body as she worked to remove my pubic hair. Once that thick folic patch had been cleared, Allie, true to her word, took me into her mouth again. Suddenly that light detachedness was coupled with a swooning euphoria at her touch. I remember reaching my hands out to her shoulders because without an anchor I would have drifted away completely. Allie was skilled, and eager, working my shaft with both hands, and running her tongue along my now smooth testicles. When, an indeterminable amount of time later, I moaned out my impending orgasm, Allie diligently held her lips in place to catch every last drop. She did not swallow however. Instead, after opening her mouth to show off the thick globs of my seed, she gave me another sly grin before slithering back up onto the bed and, before I had a chance to react, kissing me deeply. I opened my mouth to the kiss reflexively, and that was the opening Allie needed to push my load of cum back to me. I recoiled in surprise, my face twisted into disgust, but Allie only giggled at me. She leaned forward and with two hands and all her body weight, she pushed me back down so that I was flat on my back.

"You need to make a decision, Chris." Allie said, her voice now flat and serious. She climbed back on to my lap, her tantalizing ass once again rubbing up against my cock. "Again, it's all really up to you, but if I'm going to have you ready on time, we need to get a move on."

I swallowed heavily, my head still swimming in a concoction of foreign substances. Allie didn't help things, instead she leaned forward until she was flat against me, her tits pressing into my chest, and began to murmur things into my ear.

"I know the guys have been sending you 'taunts' every week, pictures and clips of me, and others. Did you watch them?" My nod was tiny, minute, but it was all the encouragement Allie needed to keep going. "Did you jerk off to them? Those pictures of my sexy, slutty little body taking and serving and pleasing all those big hard cocks?" I didn't nod, but I think the way my cock was rapidly hardening again beneath her was confirmation enough. "Mmm, yeah you did. You jerked off to clips of little sissy sluts like me getting fucked and sucking cock. Hmm, there was one picture...oh here! You can't see his face in there obviously, but this is me sucking Jeremy." She waved her phone in front of my face, and it was a familiar picture to me: Allie, on her knees, tiny cock barely visible at the bottom of the frame, with her mouth stretched around a truly impressive cock. It had to be a good four inches longer than my own and almost twice as thick. I gulped. I remembered this picture. I had actually looked at it several times while stroking myself in the past.

"I see you recognize it." Allie was practically purring by now. "What do you like most about it? Do you like how slutty I am in this?" I nodded, but Allie wasn't done. "Or, do you like looking at Jeremy's big hard cock." With every word Allie undulated on top of me, rubbing her ass against my cock, now once again fully erect. Without waiting for me to answer, Allie continued. "Jeremy's an interesting guy, isn't he? He was your roommate right?" I nodded yes again. "That's what I thought. "And how did you find out about this fantasy football league?"

My answer was soft, hesitant. Although my mind was clouded and buzzing, a realization was setting in, about how I had ended up in this position. "Jeremy told me."

Allie's reply was uncharacteristically grim and serious. "Mm. Yeah, that's what I thought. It's part of how Brian has this whole thing arranged, you know? The first person who did The Penalty actually liked it so much that they started to deliberately tank the following year. That defeated the entire purpose, so Brian made a rule that the loser is out after they're done. That means that he needs new targets every single season. The other guys know it too, so they're always keeping an eye out for potential candidates. Guys who are...I guess 'beta' is the term. Wimps, submissives. Dudes who just aren't that manly."

"Jeremy suggested me." I murmured softly. It wasn't a question. Suddenly my mind was flashing back to our time living together in college, and more realizations started to crash down on me like hammer blows. How I had always done the lion's share of the housework and the cooking, because 'I was so much better at it than him'. How he had gotten laid practically every weekend, while I was usually in the other room beating off or playing online RPGs. The time I had mentioned the cute blonde I had a crush on in my calc class, only for him to sleep with her two weeks later. 'Bro, I didn't even know that was the girl you were talking about!' All those moments flashed into my head, but they weren't the realization.