Valerie, 30-something crossdresser

"Hi there, big boy," she said with a smile. Her lips were painted bright red and instantly drew your eyes. "I was afraid you weren't going to show."

You slid into the booth opposite her, taking her all in. Valerie had a pretty face, but otherwise was only moderately passable as a woman. She was tall and thin with a flat chest and was currently wearing a long black wig. You could only see her from the chest up, but you'd seen the rest online. She had nice legs and an amazing ass (even for a woman). She also had a massive cock.

"I'll admit, I was nervous," you said.

"Everyone is their first time," Valerie said and you felt her foot slide up your calf. "Its hard to step out on a life and a life style you're used to."

You laugh nervously.

"Sooner or later, most guys find their way to gay, trans or crossdresser porn," she said. "It usually goes no further than them jerking off to cocks in the bathroom while their wife is asleep in the bedroom. Most of them would never admit it. But if a shemale with a big swinging cock walked in that bathroom with them, they'd be on it quick."

You nod in agreement. Her toes find your crotch and start to tease your cock and balls, almost tickling them.

"For me it was different," she said. "One night while jerking off, I grabbed a pair of my wife's panties from the hamper and put them on. God they felt so good against my skin and made me feel sooooo sexy. I put down the porn and jerked off looking at myself in the mirror."

"How did that lead to this?" you ask.

"It started with panties, then a bra and then her clothes," she said. "Now I have a storage unit full of women's clothes of my own. Each step felt better than the last! Then I bought my first wig. Thats when I started posting pics online, and the responses I got from guys were just so fucking hot. The first video I got from a guy tributing my photo had me hooked."

Finally her foot stopped teasing your now slightly hard cock and seriously attacked you.

"What about your family?"

"They have no idea," she said. "During the day I am a mild mannered CPA named Steven. And before you ask, I really don't do labels. But since I am sure you want to know...I still consider myself a man. A straight man, actually. Except when I'm Valerie, she ia all woman. She might have a cock, but she is just another cock hungry slut."

She is now stroking your fully erect cock through your pants.