The Punishment

Fucking fantasy football.

I knew there was going to be a punishment for finishing last in our fantasy football league. I didn't know my friends were going to be so extreme about it.

Maybe I should've known. Now that we're all 30-somethings, I had seen the punishments escalate over the years. It started innocently enough-we made Greg sign up for and run a 5K when he finished last eight years ago. All of us being friends for so long, we had no hesitation in upping the penalty year after year, resulting in a situation where, two years ago, Tom had to go on a cruise that we'd paid his ex-girlfriend and her new husband to also go on, and last year, we paid a detailer to paint Elliott's car pink with all our faces on it.

Stupid bro-y shit that, yes, made us all laugh. And that took advantage of our intimate knowledge of each other-and the things we all care about-to exploit the loser into doing truly humiliating things.

I should've known what was coming for me. I don't know how I'll look them all in the face next year.

We dish out these punishments when we all meet at Greg's house to draft our teams for the upcoming season. Now that we're all older, we have to arrange the draft months ahead of time so we can fly or drive in and spend the weekend together.

Yeah, I bought a plane ticket and took work off for this.

I was the first to arrive for the weekend so I went to Greg's and his wife, Rachel's, house to hang out until all the guys came in. While Greg showered, I sat on the couch and Rachel came over and handed me a beer.

"So how's life?" she asked, sitting down beside me.

"Oh fine," I said. "Kristin's good. Kids are good."

I must've seemed distracted because Rachel said, "You're worried about your punishment, huh?"

"No, no," I said. "As long as they don't mess with my job or my family, I'll be fine."

"I know what it is," she said.

"You want to tell me?"

"You'll find out soon enough."

"Oh c'mon, what's that supposed to mean?" I asked.

Rachel rolled her head back and laughed dramatically. She even twiddled her fingers.

"Greg told you what the punishment was?"

"Uh huh," Rachel said.

"After all these years, you won't tell me?"

Like everyone else in the league, Rachel went to high school with us. She knew me as well as anyone in the league did, and I could tell from her stifled giggles that this was going to be a good one.

"Well he had to ask me if I'd participate," she said.

"What?"

"That's all I'm going to say. I don't want to ruin the surprise."

"I thought you were heading out of town or something," I said.

"I am. After your punishment," she said.

"Please, just tell me."

Rachel laughed like a cartoon villain again and then bounced off the couch and walked toward the stairs.

"See you in a bit," she said.

"Fuck me," I muttered under my breath.

I should have known.

"Sam, buddy," Greg said, thundering down the stairs.

I stood up to give him a hug, and he came in hot, grabbing me in a bear hug.

"Hey man," I said.

"You're looking good," he said.

"Shut the fuck up."

Greg was a personal trainer. For as long as I've known him, through all the years of gym class and football and gym sessions, he'd always been able to bulk up more than I had, so whenever he said, "Looking good," it was a not-so-subtle nod to the fact that I look waifish next to him. It had always been a friendly competition between he and I to see who could run fastest, lift the most weights, throw balls the farthest. In short, he took delight that he was still, after all these years, bigger than me.

"No, I mean it, man," Greg said.

"Well, thanks. You look normal."

"That's the spirit," he said.

"Hey, let me ask you something," I said.

"What's that?"

"Rachel said she knows what my punishment's going to be. What the fuck's up with that shit?"

"Oh yeah she knows," Greg said.

"That's not how we do this."

"Well, Sam," he said, stepping back and picking at his teeth. "I wanted to pull out all the stops this year being that you've never finished last before."

"What's she got to do with it?"

"You'll see," he said.

"Well, when's everyone getting here? I want to get this over with."

"Tonight."

"Ugh," I said.

"But your punishment starts in a couple minutes," he said.

"Oh no."

"We've been friends a long time."

"Uh oh," I said.

"We know things about each other," he said.

"What are you getting at?"

"All I'm saying," Greg said, "Is I think you're going to like this."

"I don't believe that."

"Eh. We'll see about that."

"You want a beer?"

"I have one," I said.

"Better finish it."

I picked up my beer from the coffee table and chugged it. Whatever my punishment was, I thought, it's going to be easier if I'm drunker. By the time I finished, Greg had a fresh one to hand me.

"Oh, Sam," Rachel sang from the top of the stairs.

"What?" I said.

"Will you help me with something up here?"

"No," I said.

"You better go help her," Greg said.

"You can't?" I asked.

"Just go, will you?"

I put my beer down and Greg immediately picked it up and handed it to me.

"If you're drunk, this'll be a lot easier," he said.

"Yeah," I agreed.

I took the bottle and walked toward the stairs. Greg slapped my ass with full force, and I yelped.

"Go," he said.

"That fucking hurt."

"It begins," he said.

I walked toward the stairs and staggered up them. "It begins" echoed around in my head and the weight of those words dropped my heart into my stomach.

"What do you need?" I asked from the top of the stairs.

"I'm in here," Rachel said from around the corner.

I walked around the corner and into the bathroom, where Rachel sat on the closed toilet. Her hand swirled water around in the tub. She giggled.

"Close the door," she said.

"What the hell is this?"

"I said close the door."

I obliged and said, "Now what?"

"Strip," she said.

"You're kidding me."

"Why would I be kidding you?"

"Because you're sadistic and trying to get me in trouble with Greg."

"This is all his idea."

"You're going to see my dick."

"Sam. Take your clothes off."

I looked to the door, hoping Greg was walking by so he could see what was going on and put a stop to it.

"Girls go into the bathroom together all the time."

"Yeah but..."

Oh, I thought. Oh no. They know. How do they know?

"And I wouldn't call what you have a dick, by the way. Not tonight at least."

"This is fucked up."

"You love it. I've seen pictures."

"Of what?"

"Of SammySlut."

My username for a couple sites I use to post photos of me dressed as a woman. Oh no. Look, I've always had a crossdressing tendency, a compulsion, but I've never acted on it with anyone else. I always dress up at home, take some photos, jerk off and then, you know, throw my clothes in a dumpster to erase all the evidence. I started dressing up when I was really young, before I can remember probably, stealing my sister's bras and panties, then dresses. Then, when I grew taller, way taller, I borrowed my mom's. Then I started dressing in my girlfriends' clothes, then ultimately started to buy my own. It was always a wholly self-gratifying experience that I was ashamed of and happy to keep to myself and some anonymous users online. This was crossing a bridge way too far.

How did they find those photos? The only way they could've found them is with access to an FBI database or else they were on the same sites I was.

"Where'd you find them?"

"It doesn't matter."

"No it does. I need to take them down so more people don't see them. I mean if you guys saw them..."

"Relax, Sammy," Rachel said. "Your photos are safe. Unless, that is, you don't get in the tub and do every little thing I say."

I sighed. My heart was beating out of my chest, anxious that my photos, which could ruin my marriage and, likely, career would get leaked to other people. I mean there are a lot of photos of my face, that's probably how they knew it was me, but there were also some dirtier photos of me in compromising positions with some compromising toys. Oh god.

I took off my shirt and slid my pants and boxer-briefs to my ankles. I stood up and Rachel giggled, covering her mouth.

"Yeah, that's not a dick anyway."

"Get in the tub?"

"That's right, Sammy."

I stepped into the tub, which was scented with lavender and filled with bubbles. My friend, true to form, really did know how to humiliate me. Fantasy football isn't even that fun, why was I in this goddamn league?

"What now?" I asked.

"Just soak for a little bit," Rachel said. "Here."

Rachel reached over to the counter and pulled a magazine off it. She handed it to me. Cosmopolitan, with a subhead in big pink letters "The Sex Issue."

"Read up," she said.

My eyes scanned over another title, "50 tips for great oral sex." When I opened the magazine, it naturally opened to that article. Of course.

"Now, have you ever shaved your legs before?" Rachel asked.

"No, why would I-"

I stopped myself remembering my cover had already been blown. Ironically, I was reading about how to blow.

"Yeah."

"No, I haven't shaved my legs."

"Use this. Start at the foot, and go nice and slow."

I grabbed a pink razor from Rachel and lifted my foot out of the water. I held it to end of my leg.

"Do I really have to do all this? I mean, my wife is going to think something's up with this."

"I have explicit instructions to make you the most passable, sexiest, sluttiest girl I can. You can't have hairy legs and be a sexy girl, can you?"

"No," I said. "Dammit."

I slid the razor over my leg, and washed off the hair in the tub. I made quick work of each leg, going all the way up to waist. I appreciated the cool respite of sticking each leg back in the sudsy water after they were smooth.

"Perfect," Rachel said. "You're a natural. Now get out, shave your face and meet me in the bedroom."

Rachel left, and I got out of the tub. I thought I could just run. Cut all ties from my friends, blame the photos on photoshop. But instead, I brought the razor to the counter, lathered up my face and shaved. Some deep part of me was betraying my instincts to get out before I got in too deep.

"'Nother beer?" Greg called from outside the door.

"Don't fucking come in here," I said.

"Take it easy, SammySlut," he said, then laughed. "Grab this beer on your way to the bedroom."

I finished shaving and downed the rest of the beer I had brought up to the bathroom. I opened the door, grateful not to see Greg there. I reached for a towel, and seeing only a pink one, of course, wrapped it around my waist. I picked up the beer Greg had left and walked to their bedroom. Rachel sat at her makeup table, with an extra seat beside her. She patted it twice.

"Have a seat."

I walked over to the makeup table and looked in the mirror. I could see the anxiety on my face. Rachel must've seen it too.

"Listen, Sam," she said. "I know this is hard. Cruel even. But I also know you could've blown this whole thing off by now. It must've been tough living with this secret."

"It has been."

"So," she said. "Just for one night, let's see what happens when Sammy comes out."

I was silent.

"I'll be there every step of the way," Rachel said.

"You will?"

"Uh huh. They may think this is a punishment, but I think this is a chance for your true self to shine."

"Are you good with makeup?"

"Am I good-Sammy, do you see me? I'm fucking great with makeup."

I laughed, and felt my heart start to ascend to its normal location for the first time in a while.

"Close your eyes," Rachel said. "When you open them, you'll be a new person."

"OK," I said.

I closed my eyes and felt the heat of the makeup table's lights on my face. Then I felt the familiar coolness of foundation and Rachel's soft hands. I smelled the talc-y smell of powder. I felt the familiar sharp edges of pencil over my eyelids. Then, brushes over my eyes, my cheeks. I felt pencil go around my lips, then wet firmness against my lips. I felt the delicate application of lashes to my eyes, and their long wisps brush against my cheeks. I had never done makeup like this before, and I was glad that if I was going to be subjected to public humiliation or whatever the punishment was, that Rachel was taking good care that I looked alright.

"Well," Rachel said. "I think you'll be surprised."

"Can I open my eyes?"

"Please."

I opened my eyes and stared at my reflection. I knew it was me; I was under no illusion I would create a, you know, perfect female illusion, but I looked good. I looked feminine. Even with my wispy, short hair, I looked more female than male, more light than heavy, more pink than blue. I felt my cock stir.

"Hold on," Rachel said.

I saw in the mirror Rachel walk to the dresser behind us and grab a long, straight, brown wig. It matched my natural color and was longer and lusher than I could have ever gotten on my own. She affixed it to the top of my head and I almost cried at how good I looked. How complete the transformation felt at that point. I forgot all about fantasy football, and thought only about the girl in the mirror.

"Better than SammySlut, huh?"

"I'd say."

I ran my fingers through my hair.

"Don't fuss with it too much, or we'll have to run a comb through it every five minutes."

"I'm sorry," I said. "I can't help it."

"I know." Rachel said. "You look great, girl."

"Thank you."

"Now drink up, I'll go grab you another one."

I forgot all about needing alcohol to curb my anxiety. Being made into this passable female goddess, at least in my eyes, had calmed my nerves. When Rachel opened the door, the sound of my friends laughing raucously filled the room. I hadn't realized they had arrived while I was being transformed.

"They're all here," Rachel said, coming back into the room. She handed the beer.

"So, what?" I said. "I'm going to go down there and look like this all weekend? That's the punishment?"

"You'll see, Sammy."

Rachel walked into her closet and rummaged around while I positioned my face in different directions, trying to cast favorable light on my new visage.

"Now, we're about the same thickness," Rachel said, coming out of the closet, "but you're much taller than me. So you can wear my bra and panties, but I got you a special item just for you."

Rachel stood in the mirror dangling a matching pink satin bra and thong set. Just the shimmer of them and the thought of them being on my body made my stomach stir.

"Put these on. I know you know how to do that," Rachel said.

I stood up and slid the satin pink thong up my smooth legs. I affixed the bra behind my back like I'd done it before, because, well, I had.

Rachel walked into the closet and came back with a ribbed pink corset. Garter straps dangled, as did a lacy pink ribbon that would tie around my back.

"I'll help you with this," Rachel said. "We're going to give you curves like you never dreamed of."

I lifted my arms and Rachel wrapped the pink corset around my waist. Rhinestones on the ribs shimmered in the light of the makeup table. Just as I started to smile, Rachel pulled the strings and my breath left my stomach.

"No one said being a real girl is easy," Rachel said.

"No kidding."

Rachel threaded the lace ribbon through the corset, pulling often, and tied it into a bow at the top. I regarded myself in the mirror: I could be a model, I told myself. Tall and skinny, with enough curves to make my hips and butt look enticing.

"Now have a seat, if you can, and slide these on," Rachel said, handing me two latex stockings.

I sat down and felt the restrictiveness of the corset as I struggled to pull each stocking up my leg. I stood up, and Rachel fastened the clasps.

"Wow," I said, looking at myself in the mirror.

"One more thing," Rachel said.

She went back into the closet and came back with some clear high heels that only a stripper would wear.

"We had to find these in your size. Greg remembered it," Rachel said.

I remembered only then Greg was in on it. I wondered what he was telling all my friends downstairs.

I slid into the heels, using Rachel's arm for balance.

"Now you can practice walking, Sammy," she said, "but my guess is you'll be on your knees quite a bit."

"Huh?"

"It'd be a shame to parade around such a pretty slut and not put her to use, don't you think?" she said.

"What's going to happen?"

"Relax, pretty girl."

I walked around the room, remembering to go heel-to-toe, like everytime else I had tried walking in heels. A few close calls for my ankles and I felt comfortable. I learned to move my hips to maintain balance, which also gave my gait a feminine style.

"I think you're ready," Rachel said.

"Ready for what?"

"Your punishment," she said.

"This wasn't it?"

Rachel giggled.

"I'm going to go downstairs and see if they're ready for you," Rachel said.

"Oh god."

I thought about jumping out the window. Other people seeing me in public would be better than all my closest friends, who would never let me live it down. My friends would surely see what I felt in my gut-that I loved the way I looked. I'd be outed as the sissy slut I am.

Instead, I took a deep breath and remembered what Rachel had said. This is a chance for Sammy, not Sam, to live a little. Separating myself from my regular identity was liberating.

Rachel came back in with a couple double shot glasses.

"Tequila," she said. "Drink up."

I took the shot glass and dumped it down my throat.

"Now it's loose," Rachel said.

"It?"

Rachel laughed.

"Let's go."

Rachel opened the door and I took a deep breath. I walked across the bedroom and to the stairs. I put my hand on the railing. As soon as my first heel clacked against the wooden stair, I heard a roar from my friends downstairs.

"Oh my god," I heard Elliott say.

"This is going to be ridiculous," Tom said.

I walked down the stairs and was surprised to see the living room empty. I stood petrified at the end of the staircase, and Rachel turned to grab my hand. She led me into their kitchen, which itself had been transformed. The open frame leading to the den had been sectioned off. A thin white sheet had been taped to the frame, and I felt the presence of seven guys in the room on the other side. Their energy caused the sheet to rattle. That's when I noticed the hole three feet off the ground.

"Wait here," Rachel whispered.

"Now you guys are in for a real treat," Greg said.

"Isn't this a little gay?" I heard Vic say.

"Why is this gay? This girl, I'm telling you guys. I found her on Tinder. She lives for this kind of stuff. Take a look."

I waited and heard the guys laugh in chorus. I think I heard a high-five.

"See, she's super hot," Greg said. "Amber?"

My heart dropped. Rachel looked at me and nodded.

"Yeah?" I said. I was surprised at how high my voice came out.

"You ready for a good time?"

Rachel nodded again.

"Yes, sir," I said, again surprised with my voice but also my natural submissiveness.

"Sir," I heard Elliott say, laughing.

"Hey wait," Tom said. "How do we know this isn't just fucking Sam?"

The room burst out into laughter. Rachel looked at me with kind eyes.

"His punishment is that he doesn't get to join in," Greg said.

"Oh my god," Tom said. "This is nuts."

"Or maybe it's Rachel," Vic said.

The room laughed again and I saw Rachel blush.

"You wish," Greg said. "Amber are you ready?"

Rachel looked at me.

"Are you ready, Sammy?" she whispered.

I thought about what was ahead of me. I looked in the hole. I saw the shadows of seven grown men, no longer my friends, just horny dudes behind the sheet. I looked down at myself and then into my reflection in the glass patio door. My cock had begun to spring in Rachel's satin pink panties. Sammy was ready.