Okay, I know what you might be thinking, but no, I’m not transgender. I’ve never felt dysphoric, I’ve never felt envious of women (except for the cheap drinks they get on ladies’ night at Cruiser’s Pub) and I have zero eye for fashion. Plus, I think I’m pretty decent-looking as a guy. I’m a straight-up t-shirt and jeans kinda dude. “But, Mike!” you might say. “Why are you currently wearing a black dress, high heels, and a wig? And what’s with that makeup?” It’s called cross-dressing, you plebian, and men have been wearing women’s clothing for performances for centuries. Look it up. “But why are you doing it right NOW?” you might insist.

It's just a fucking bet, all right? It's not a lifestyle!

It all started when I was shooting free-throws with my buddies Jeff, Chris, and Tim. I was lining up my shot, started to bend my knees, when Tim ran up behind me and began tickling my sides. I laughed, which came out as more of a girly giggle. Chris and Jeff pounced on this perceived flaw.

“Dude, when did you learn to laugh from your sister?” Chris called out teasingly.

“I think I’m a little turned on!” Jeff followed up.

I had dropped the ball thanks to the tickling, which was deftly retrieved by Tim who made a shot at my expense.

“Shut up, assholes! I can’t help that I’m ticklish!” I yelled, my face reddening between some combination of embarrassment and frustration.

Tim turned to face me. “Honestly, man, your voice is pretty androgynous anyway. Like, if I wasn’t looking at you, I wouldn’t know if you were a guy or a girl.”

Now my face was red hot. “Fuck you, dude! I sound plenty manly enough. I’ve scored more dates than any of you rejects!” I retorted, attempting to force my voice into a lower register.

Chris burst out laughing. “Now you just sound like an angry lesbian! Y’know, one of those really butch ones with the short hair and the flannel and shit?”

I ran a hand through my hair and mopped the sweat off my brow with the bottom of the tank top I was wearing. I didn’t really need to do this, but I didn’t want these jerks to see my face. I was really self-conscious about my voice and I didn’t want them to see how much this was all bothering me. On the one hand, I kicked ass in karaoke. On the other, I know I’ve gotten more than a few “ma’ams” on the phone and I was pretty uneasy about it.

Jeff got a sly smile on his face. “How about we put some cash on this?” Dude was born money. Like, his dad owned a huge construction company and he was prepping to take it over in a few years when he finished his business management classes. “I bet that if we took you someplace where people didn’t know you and you were dressed as a chick, no one would be able to tell the difference.”

Well fuck. He knew I was broke as hell. I was working part-time at a convenience store to pay my tuition at community college and honestly struggling to get by. I lived with my single mom and my sister, a junior in high school. Mom did her best to pay the bills and keep food on the table, but that didn’t leave anything left over to help us through school. I qualified for financial aid - a couple of grants and a scholarship, but I refused to take out any student loans. I didn’t want to start off my adulthood buried in thousands of dollars of debt. But it also meant I didn’t have any extra spending money for luxuries like cars, clothes, or a decent smartphone. I took the bait.

“How much money are we talking?” I asked cautiously, eyeing Jeff as Chris took his turn at the free throw line.

“Hmm. How about two grand?” Jeff offered.

I balked. “2K? Dude, you know I can’t afford that if I lose!”

“Well, it’s not really about the money, is it?” Tim said, grinning maliciously. “It’s about the fact that you know you’re gonna lose!”

Chris retrieved the ball and walked toward the rest of us, casually dribbling as he did so. “How about we make the bet proportional?”

I raised an eyebrow quizzically. “What do you mean?”

“Well, we make it a percentage of your income. Say like 10% of your next check,” Chris replied, dribbling the ball without making eye contact with any of us.

I was working at a hardware store for 16.50 an hour. I started there when I was 16 and had kept the job through the rest of high school and the beginning of college, worked my way up a bit. But still, I was only pulling about 25-30 hours a week. With my bi-weekly check, my net after taxes would be, I dunno, like $650? So… $65? That’s not so bad.

“Okay, that’s doable,” I said. Chris passed the ball to me and I dribbled it absently as I awaited Jeff’s response.

We all knew that Jeff didn’t currently work, but he did receive a monthly stipend from his parents. But none of us knew how much that actually was, just that he was already well on the road to being a millionaire. He looked at me thoughtfully for a moment (the time of twelve lazy dribbles of the basketball) before he finally said, “Okay. You’re on. Twelve hundred bucks from me. What have you got?”

Shit. He was seriously pulling 12K a month? What the actual hell? Would my sixty-five bucks even mean anything to him? I sighed. There was no point in hiding it. “Sixty-five,” I replied flatly and passed the ball to Jeff.

He dribbled the ball a few times and shot from where he stood. Swish. We all let the ball bounce at the edge of the court toward the wall as we awaited his response.

He smiled again. “All right. Ten percent is ten percent. Honestly, this probably hits you harder than it does me,” he quipped. Yeah, no shit, asshole. “So let’s set the rules,” he went on. “I pick the venue. Next Friday night. You have to put actual effort into this - so shave your legs, wear a dress, get a wig, and put on makeup. Have your sister help, if you need to. You can’t tell anyone you’re a guy and you can’t tell anyone this is a bet. Use your normal speaking voice. If more than three people figure out you’re a dude, you win. If less than three people figure it out, I win. Fair?”

I thought it over for a few minutes. What was one night in drag for twelve-hundred bucks? I’ve done stupider shit for free. I walked the handful of steps toward Jeff and extended my hand. “All right, you’re on.”

Jeff took my hand and shook it. “See ya Friday… Michelle.” Using the handshake as a grip, I pulled him toward me and lightly punched him in the shoulder. 

“Yeah, whatever. You’ll be eating your words Friday night,” I said.

***

So yeah, that brings us back to two hours ago. There I was, dressed like a sorority co-ed ready to party at the club, standing in a room full of people I’ve never met before. It was a house party at some upper crust neighborhood on the south side of town filled with trust fund kids and silver spoon brats. I felt uncomfortable mingling with the nouveau riche even on the best of days, dressed normally, let alone dressed in drag with my dick tucked between my legs like some overrated comedian on a sketch comedy show.

Jeff and Chris quickly abandoned me. Tim decided not to come because he didn’t want to see me in drag - thought it’d be too weird - but Chris was the judge for our wager. He’d be the one to make the final call at the end of the night.

Honestly? I was super nervous. I mean, I can hold my own in a fight, but if someone here took offense to me and started some shit I wasn’t sure how well I could fight back in my thrift-store heels and black mini-dress. I bought the wig from Amazon since it was the middle of summer and I couldn’t just walk into a Spirit Halloween to buy one. It was about shoulder-length, kind of a dirty blonde color. My sister styled the wig and did my makeup, although I think she went a bit overboard on the eyes. She even did my nails - a creamy pastel purple with white tips.

I looked hilarious.

Since I was on my own, I decided I would just have fun and do whatever. Whatever beginning, of course, with a red plastic cup rather generously-filled with berry-infused hard apple cider. The music was a rather entertaining collection of contemporary hits. What was this, Maroon 5? “Girls Like You?” Well, it’s a few years old, but not bad. I could dance to this.

A few other folks were dancing, so I decided to join them. “Hey, how’s it going?” I asked as I approached. One of the guys turned and looked me up and down with a smile. Not the reaction I was expecting. Or wanted. In a mild panic, I looked toward Jeff and Chris who were looking on from the other end of the room, knowing smiles on both their faces.

Before the guy could approach, I was intercepted by an arm from the side and a voice that called out loudly against the music, “Hey! Don’t get any ideas, Jordan! She’s off the menu!” I looked down to my right. There stood a gorgeous little lady. She was probably 5’ 5”, huge gorgeous brown eyes and long brown hair, dressed in a simple black v-neck and a white pencil skirt. I felt all the more ridiculous dressed up like this next to a girl like her. 

“What’s going on?” I asked as I leaned close to her.

“Girl, unless you wanna end up as another conquest broadcast on Snapchat, you should follow me!” she said directly into my ear. 

I laughed, about to tell her why I didn’t need to worry about that, when I remembered the terms of the bet. I just nodded and happily followed this cutie wherever she wanted to lead me.