The Sissy Hotel

"Ethan. But can you call me Emily?"

"Sure no problem. Ethan's a nice name though. So what brought you to the hotel?"

"I just wanted to play at being a girl. I love the idea of dressing up but never had the opportunity."

"So you must be bisexual I guess? I mean, if you don't mind me asking?"

"I'm straight."

"Huh?" she said incredulously. "I saw you take more dick today than I have ever even seen in my entire life. How does that work?"

"I'm just not into guys. I don't find them attractive at all. It's just like, a kind of role play when I'm dressed up. I want to play at being a girl." I missed out the part about wanting to be emasculated. "How did you get this job? It's an unusual place to work."

"I met Gisèle at an LGBTQ event. I was having some questions about my sexuality. I think I am kind of bisexual. I'm on a spectrum."

"What like autism or something?"

"What? No. Well maybe a little. It would explain a lot now you mention it. But I meant a sexuality spectrum. I might like women, I'm not quite sure. I'm somewhere in the middle." She briefly glanced at me while smiling. "You know when I saw you earlier in your little French maid's dress, you looked just the cutest person in the world. You looked a million dollars but I only had a hundred." Her eyes lit up. "And when you did that curtsy, oh my." She touched her chest over her heart. "I just wanted to hug you on the spot. That outfit is a keeper you know."

"When I saw you dressed as a fairy with wings with your sweet little pixie haircut, you had me forever. I nearly wet my panties I was so excited." I'd been trying to scare her away. "The red dress you have now, you're sexy as hell."

I'd spent a lifetime being invisible. Compliments were like reaching an oasis after years in the desert. I stumbled over my words desperate to think how to compliment her back but she continued before I had the chance. "I once tried sleeping with a woman but didn't like it. I kind of want a man but I love the aesthetic of women so much more. Does that sound weird?"

"You sound perfect to me." She smiled and put her hand on my knee.

When we got to dinner, she had to coax me out of the car. I just couldn't move out of fear of being seen dressed as a girl in public, but I went through with it. No one called me out. We talked a lot over pizza and I got to know all about her life. She lived in New York and was just temporarily in the area to help out Gisèle. She was planning to fly back tomorrow.

After dessert she asked me what I wanted to do next. I thought for a moment but it didn't take me long to come up with an answer.

"I'd love to go shopping. I mean like real girl shopping. Trying on clothes."

"Big mistake!" Melissa shouted with some glee.

"Why? They're open late round here right?"

"No, I mean like in Pretty Woman. It's a pop culture classic. You must have seen it?"

I shook my head.

"Oh wow. We will watch that. It's about a rich businessman called Edward who encounters a prostitute called Vivian and falls for her. There's a famous scene where he takes her shopping at upscale stores." She paused for a second. "So what if a not exactly rich but middle income, doing OK, accountant girl takes the wannabe whore shopping?"

"Oh Edward, sweep me off my feet tonight." I had a realization that here was a woman who could be the man I wanted. I hoped I could be the girl she wanted.

We went to a half dozen stores, trying on dresses and modeling them for each other. I had the time of my life. I'd never had that experience before. In the end, Melissa bought me a cocktail dress, the first I'd ever owned, I would treasure it. We drove back to the hotel late in the evening. On the way she asked me something. "So I'm leaving tomorrow. I know its very soon and I don't know how you feel, but would you like to come with me?"

She surprised me with the question and I didn't immediately answer.

"Besides, my apartment is messy and I could use a good maid," she added. That made me laugh. "We could see how it goes?" she said, almost in a pleading voice.

I leaned on her shoulder. "There's nothing I'd rather do." Did I really have a girlfriend?

Back at the hotel, Melissa picked up the keys to my cage.

I lost my third virginity.