It was a Friday night, and I was dressed to fuck. I wore a pink bra, matching panties and black high-heels. It didn't matter to me if someone pounded my ass or if I did the pounding. As long as my partner dressed up like a girl and held nothing back, I was down for anything.
I turned on the computer in my living room and checked my email to see if anyone had responded to my craigslist personal ad. The first two messages were from guys who "thought" they wanted to try cross-dressing. (They never do.) I deleted them and moved on.
The third message sounded promising:
"Loved your ad! I'm also into cross-dressing. Clean, non-smoking white guy in decent shape. 27 years old. Available Friday night. Email me after 7 if you want to play. P.S. You can call me Cindy."
I checked the clock on the wall. It was 7:02.
I hit reply and typed, "Horny as hell here. Wanna play?"
While waiting for an answer, I watched a slideshow of soft-core porn I had saved on my computer. Pictures of tits and asses wrapped in lingerie flashed across my screen. I folded my arms and tweaked my nipples. As the pressure built in my groin, I resolved to fuck someone that night, even if I had to get a hooker.
But that wasn't going to be necessary. Cindy replied quickly, just as a series of Jenna Jameson bikini shots began parading across the monitor.
"Come on over," Cindy wrote. "It's going to be a 3-some. I'm at 1021 Van Buren, Unit 2. Please be fully cross-dressed and ready to fuck. Need directions?"
Van Buren was on my sales route for work. I knew exactly where it was .I replied: "Don't need directions. See you in 30 minutes."
Within 25 minutes, I was cruising through dark suburban streets in my silver BMW. I wore a tight, black cocktail dress that showed off plenty of chest and thigh. My face was done up in heavy lipstick and eyeliner. I wore a pink "fuck me" wig that fell almost to my shoulders and then curled in toward my neck.
My heart thudded against my chest as I struggled to keep my car at the speed limit. The last thing I needed was an overzealous cop booking me on a one-way ticket to the county jail.
A million questions ran through my mind, but I kept coming back to one: Cindy said it was going to be a three-some-- who was the third?
The address Cindy gave me was a two-story town home in a swank neighborhood about a mile off the interstate. A light was on behind the curtains in Unit 2. I parked on the street, opened the car door and put my high heels on the concrete.
To my relief, no one was out on the street. I practiced walking like a woman on my way to a green front door with a gold lion's head knocker. I took a deep breath and told myself, "you're a fuck-toy whore -- act like it" and then rang the door bell.
Light footsteps rapidly approached the door. Someone on the other side paused to look through a peephole. And then the door swung open.
It wouldn't have taken anyone long to figure out that the person holding the door knob was a man trying to look like a woman. He wore a lacy, black corset with thigh-high stockings and panties that bulged with an obvious hard-on. The long black hair swept over his shoulder was no doubt a wig. Even the liberally applied make-up didn't do much to hide his gender.
"Hi, I'm Cindy," he said in a husky voice straining to be feminine. "You must be our date for the evening."
"I believe so," I said in an equally ridiculous voice.
Our eyes locked together. I held Cindy's gaze while stepping into the doorway. Cindy gave a sexy half a smile.
"I don't remember inviting you in," he said.
"Me neither," I said.
I leaned in to give him a slow, passionate kiss on his apple-red lips. My cock rubbed against his as we embraced. Cindy's lips melted into mine. I playfully flapped my tongue at them. He did the same to me. We might've fucked right there in the doorway, but a horn honked out on the street. Cindy jumped back. I looked over my shoulder. Whoever it was kept driving. The street was empty. Cindy giggled nervously. But not me. I was ready to get to business.
"Well," I said, "are you going to let me in, or do I have to fuck you right here with the door open."
Cindy straightened out quickly.
"You know," he said, "I don't think I've ever met anyone quite like you."
Cindy stepped aside and let me walk into the living room. It was lit with about a dozen candles and smelled of incense. A smooth techno beat played on a stereo. A coffee table was pushed into a corner. Four dimples in the rug told it usually sat in front of the black, leather couch.
I don't think anything could've prepared me for what was lying on that couch.
She was the sexiest woman I've ever seen. She had long, black hair, cantaloupe-size tits and slender legs. All she wore was a silky, blue bra and matching panties. She lay on her side with an elbow propping her up and one leg crossed over the other. The girl didn't say a word. The half-smile on her face did all the talking.
"This is my sister, Amanda," Cindy said. "She's going to help us fuck each other."
Amanda bit her pinky finger and giggled. It was the same sound her brother had made in the doorway.
