Dating

 A cross-post from Tumblr, inspired by the wonderful work done by Emma Says.

"What do you think?" Ashley, my best friend, asked me, taking the bra between her fingers.

"It...I...it's really cute," I said, "it's a nice color on you."

"I meant for you," she said.

"Ashley," I swallowed.

"Guys like girls in pretty lingerie," she said, "you're never going to get a boyfriend wearing bras now and then, you need to wear them all the time. Pretty ones."

"Ash..." I'd worked hard at training myself to ignore how pretty she was, to never think any lewd thoughts about her, to de-sexualize her. It was difficult at first, but over time it became second nature. A girl I'd lusted after for years became like...my best girlfriend. 

"I assume there are matching panties...yep...right there," she said, looking to her left.

I never said I wasn't heterosexual. I never told her I wanted to be feminine. But I never denied it when she implied it. I never said anything when we spent hours talking about girl stuff. I never said anything when she mentioned guys. I nodded along when she commented how cute some guy was. I let her dress me in cute clothes now and then.

In an effort to stay close to her, somehow I became, in her mind, her bestest, gayest friend.

The thing was, the longer I played along, the more often we talked about different guys, the more often I found myself not pretending, meaning it almost became second nature.

"Ash, I..."

"Did that guy from the party last week call? I know he thought you were cute."

"He...he texted, but..."

"Brittney says he's single. I bet she'd set you up."

"I don't...I'm not..." I wanted to say it, I wanted to tell her I liked girls, I wanted to tell her I wasn't gay, but the word wouldn't come out.

"You know at some point you have to lose your virginity, right?"

"Ash!" I said, looking around to see if anyone heard her.

"Listen, all you have to do is look pretty, he'll do the rest, trust me."

"Ash, I don't...I mean...I never."

"Can I tell you a secret?" she asked.

"What?" I asked.

"I kind of fibbed. Brittney already talked to him and, well, she kind of set you up on Saturday."

"On...on a date?"

"Of course on a date," she said. "I know you're nervous, but don't worry, Brittney told him all about you and he's totally into trans girls."

It was like a make or break moment. I either had to tell her I wasn't gay, tell her I'd been lying for months, or accept it. "Can...can we double date?" I said, stunned to hear the words come out of my mouth.

"Of course," she smiled, as if she was relieved that her bestest, gayest friend was actually gay.