The last time I fucked a guy up the ass was just yesterday. It was a Monday afternoon, and my wife was at the office. I was supposed but working but was actually reading the comments on my last story, seeing how many other guys are into the same thing as me, and getting deep into porno. I'd started with my customary striptease videos, moved to lesbian and then made the jump to transsexual porn. By the time I got to bukkake, I was psychotically horny. That's when my phone buzzed with a Grindr message from MarriedCD.
We exchanged a few messages, and I learned MarriedCD was three years younger than me. He liked to cross dress, and his wife had no idea. She thought he was catching up on paperwork at the office. He was indeed at the office, but he was watching porn while wearing his wife's lingerie.
"Want to come over? he asked. "I'm alone."
My cock stiffened. I was excited but knew from hard experience that we were still a few crucial steps away from a hookup. First, we had to exchange pictures. We agreed to trade body shots only, no face. I sent MarriedCD a shot of my hairy chest and hard cock. He replied with a shot of a total dad bod stuffed into a hot pink bustier and panties. The skin of his ball sack was sticking out one leg hole. A mound in the lace outlined his big cock.
"Perfect," I wrote.
And I meant it, too. There is something uniquely attractive about a non-passable crossdresser. The ones who just throw on some women's undies without any thought to attractiveness or lifestyle are the ones who are motivated by shame and like to be feminized and humiliated. I love that because I get off on shame and humiliation, too.
The next step to a hookup was a big one. He had to give me his address. This is where most hookups falter. One guy just disappears or comes up with an excuse for why he can't meet that day. I know the game because I've played it. But sometimes magic strikes, and both guys want it and have a place to play.
"Address?" I asked.
To be honest, I was waiting for the bullshit excuse because MarriedCD seemed too good to be true. But then to my total amazement, he sent the address almost immediately!
"There's some construction," he said. "Just park by my Volkswagen and come in the side door. Go to suite C. I'll be waiting. I want you to just fuck me and go."
"Got it," I wrote.
Little more than 15 minutes later I was in my pickup on a four-lane suburban parkway connecting several office parks. Google Maps guided me to one called Interstate West, and I quickly found Building B, a squat, three-story affair made of steel and glass. MarriedCD's black Volkswagen hatchback was parked next to a Dumpster topped with chunks of drywall and mounds of pink insulation. His car was the only one in the lot. I eased my pickup into the spot next to his and hustled through the summer heat to the building.
A blast of air conditioning hit me when I opened the side door. The hallway inside was half-lit by sunlight streaming in from a window on the other end of the building. The place was silent except for the low whoosh of the central air.
A head poked out of an office as I made my way down the hall.
"Over here," he said.
MarriedCD stepped aside to let me into into suite C. It was an interior office with no windows. A plastic plant and a couple of photos were pushed to the side on the desk. A couple of colorful abstract paintings hung on the white walls. A laptop played a video of transsexual porn star Daisy Taylor getting fucked up the ass by a stud.
