George entered his one-bedroom apartment, pulling Gene behind him by the hand. At least he said his name was Gene. It didn’t really matter, George supposed. Not that “George” was his given name either. It was par for the course, as they say.
This moment had actually been a long time coming for George, or “Madame George” as he called himself that evening. It took a long time to build up the courage to finally stumble into that sexy blue dress he bought so many months ago, strap on the perfectly matched heels it had taken him forever to find in men’s sizes, do his make-up like he’d been practicing and put on that shockingly pink wig he’d bought for the occasion.
He hit the bar scene in Ybor City that night, knowing which area would welcome him for what he was. Flirting with men made him nervous at first, but it got easier as the night went on. Apparently, he made an attractive woman, which made him feel more comfortable approaching or being approached. And it was nice when the men bought all his drinks for him.
And Gene was one such man. He approached innocuously enough with that old “I haven’t seen you here before” line. George thought he was handsome enough with his tight curls of light brown hair, face stubble, and just-a-little-doughy physique. They chatted for a while and, eventually, George decided to invite him home.
“I’ve got a bottle of wine if you’re interested,” said George.
“Sounds good,” said Gene as he put his jacket over a kitchen chair.
Gene seemed like a good fit for George’s first foray into this life. He was more masculine than the men George expected to encounter in the Ybor gay bar scene. But here was this man, a real man, who wanted him. It was exactly how George wanted the night to go.
As George turned the corkscrew he said, in his best womanly lilt, “I’m so glad you decided you come by. I thought it might have been a little forward for me to offer.”
“It’s all good,” said Gene.
The cork freed from the bottle. George pulled two glasses from the counter next to the sink and poured out two healthy servings. He turned to Gene, who was closer now than he realized, and handed him one. They stood facing each other in the small kitchen, clinked glasses and smiled at each other.
“To new experiences,” said George.
“Oh,” said Gene. “Is this your first time?”
George swallowed a sip of wine. “It is actually,” he said. “Is that okay?”
“Fine with me,” said Gene. “I mean, I’ve been with a trans woman before, just none as good looking as you.” He laughed nervously.
“That’s sweet of you to say, hun,” said George, actually feeling his face flush. “I’m not actually trans though, just saying.”
“Nope!” said George. “I’m just me; Madame George!” He smiled.
Gene didn’t return the smile. “Oh, I’m sorry,” he said. “I just assumed because you were at the bar in that dress that maybe you were transgendered. I’m sorry. Forget I said anything.”
“It’s fine,” said George, taking another sip of wine. He noticed Gene hadn’t been drinking his. “I like to dress as a woman, but I don’t see myself as a woman, if that makes sense.”
“It makes perfect sense,” said Gene. “There’s plenty of gay guys out there who like to crossdress at the bars.”
George knew he should have let it go, but now the wine was mixing with the various other cocktails of the night and he found it hard to keep his tongue.
“I mean, wouldn’t really call myself gay, either.”
Gene’s eyebrows contracted. “So, bi?”
“I don’t know,” said George. “I try not to think about it.” He finished off his wine in one final gulp. “It is what it is, you know?”
“Well, I mean, it’s one or the other right?” said Gene. “You’re not trans, you’re not gay, but you come into a gay bar in that dress and let me pick you up and take you home. It’s something.”
“I’m sorry,” said George. “I just never put a label on it is all.”
“But I just don’t see how you’d want to fuck a man while wearing a dress and not, at the very least, be bi.”
“Just don’t worry about it, okay?”
“I don’t know,” said Gene. “I just don’t get it.”
George lowered his voice. He reached out and took Gene’s hand. “You don’t have to get it. You got me, okay.”
Gene was looking down at George’s hand in his own. “I don’t know,” he said. “It’s just kind of like, what even are you?”
George let go of Gene’s hand. “Why is this such a big deal? It’s just something I want to do.”
“I just thought I was taking home a transsexual is all,” said George. “Transgendered. Shit. Sorry. And if you’re just a crossdresser, that’s fine and all, but now you won’t even say that you’re gay and I have no idea what you’re even getting from this.”
“I get it,” said George, forgetting the pretense of his feminine vocal act. “You’re one of those chasers. You just go around looking for transwomen. It’s just like a fetish to you guys. You don’t really care about the person at all, do you?”
“Look, I’m sorry okay,” said Gene.
George looked away, refusing to meet his glance.
“Come on, baby,” he said, taking George’s hand again. “You’re beautiful, okay? I couldn’t wait to get you home.”
“Yeah?” said George.
Gene moved in closer. “Yeah.”
Gene’s arms were around George’s waist now. He tried to kiss him but George turned his head away.
“Come on,” said Gene. “Don’t be like that.”
He kissed George’s neck. George inhaled sharply through his nose and closed his eyes.
“I’ve just been dying to suck your dick all night,” said Gene.
George pushed tighter into Gene’s body. “Oh yeah?”
Gene removed an arm from George’s waist and reached under his dress, stroking his hard cock against his silk panties.
George moaned softly in Gene’s ear. “That’s nice,” he said.
“You want it, don’t you?” said Gene.
“Mmmhmm,” replied George, feeling his breath become heavy.
“I knew it,” said Gene. “I knew you couldn’t wait to be my little cum-slut.”
George shoved Gene off of him and into the kitchen table.
“Okay,” he said. “You need to get the fuck out of here.”
Gene put his hands out to his sides. “What?!”
“This just isn’t how I wanted this to go,” said George. He swallowed the ball in his throat as best he could. “I wanted a real experience and not just to be someone’s fucking fetish.”
“Oh, you’re going to get all judgmental on me?” said Gene. “You get the high road here? You’re not even trans, you’re not even gay, so you say, and you’re out in a dress lookin’ to fuck a dude? And I’m the one trying to satisfy a fetish?”
“That’s not what this was about,” said George, unable to look at him.
“No?” said Gene. “Then I’m sure as fuck at a loss, because none of this shit makes sense to me. Seriously, what the fuck even are you?”
The tears came to George’s eyes. “I don’t… I don’t know, alright? I’m just… just…” He put his hands in the air. “Madame George.”
“Yeah, about that,” said Gene. “If you’re going out as a woman, why is that the name you go with? Why not a woman’s name for fucks sake?”
George had one hand on his elbow and the other covered his face. He shook his head. “It’s… it’s a song. ‘Madame George’ is a song. Van Morrison. It’s a song.”
Gene shrugged. “Well I ain’t ever heard it.”
George finally looked at him, his eyes a blotch of tears and make-up. “Can you please just go?”
“Fine,” said Gene grabbing his jacket from the back of the chair. “Whatever. If you’re just gonna bring me back here to be a fuckin’ dick-tease then whatever. It was nice seeing you. Thanks for inviting me over for your existential crisis or whatever this was.” As he walked out he said “Waste of a fucking evening,” and slammed the door behind him.
George pulled out a chair and collapsed into it. He hung his head and put his hands over his face. The memories of everything that lead to this night looped in his head:
The first time he masturbated wearing his girlfriend’s panties. Trading dick pics with random guys he met on the internet, sometimes with the panties on. His girlfriend leaving when she found out about it. All those months of dieting and hours in the gym just to be fit enough to pull it off. Shopping for months just to find the perfect blue dress, perfectly matched heels, and that vibrant, pink wig that would be absolutely perfect for Madame George’s debut.
And it all led to this night. This night. This is what it led to. And that was just too damn much.
George whipped off that pink wig and hurled it into the trash can across the small kitchen and brought his hand back to his face. He couldn’t help the heaving of chest as he began to sob. He couldn’t even say why.