A gay story: Sex with Married Guys Ch. 02 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.
MarriedCD closed the door. With his man tits shoved into the cups of the bustier and his cock pitching a tent in his panties, he was perfect. He was a little overweight but not huge and clean shaven with a standard suburban haircut. He totally looked like a dude in lingerie.
“Let’s just fuck,” he said. “No kissing. I’m already lubed.”
He slipped off his panties and bent over the desk. He had a nice, smooth ass. MarriedCD reached back with both hands and spread his cheeks. I unbuttoned my cargo shorts and slid them down to the floor, along with my boxers.
I put my cock between his ass cheeks like a hot dog sliding into a bun. He flinched a little but quickly settled in as I worked my prick up and down.
“You like dirty talk?” I asked.
“Yeah,” he said, barely audibly.
“I thought so, slut,” I said.
The head of my throbbing love rod found its way to his pucker-hole. I pushed forward, applying just enough pressure to let him know I was there without going in.
“Only faggots take it up the ass,” I said. “Did you know that, bitch?”
“Yes,” he said breathlessly.
It flashed in my mind that I should probably put on a condom. But I didn’t have one and didn’t know if he did.
“Ready to get barebacked, whore?” I asked.
“Shoot your cum in me,” he said.
With that, I pushed myself inside him. His ass pipe enveloped my prick like a silk glove. MarriedCD grunted just a little.
“That’s a good whore,” I said. “You like having a man inside you?”
He nodded vigorously.
I started pumping his hole like I was a derrick drilling for oil, slowly at first but steadily picking up the pace. MarriedCD’s tense body started to relax. I started to say whatever came to my mind.
“You should be ashamed of yourself, faggot,” I said. “Real men don’t have sex with men.”
That seemed to set him off. He started saying “uh, uh, uh,” and his whole body went limp. I was pretty sure he was blowing his load.
“Cum inside me,” he moaned.
That’s all it took. Even though I’d gotten in only maybe 10 or 15 strokes, I just couldn’t hold back. I fired what felt like gallons of jizz inside of him. In that moment, it was pure nirvana. All the stress in my life was gone. If I could put that in a pill, I’d take it every day and never come down.
But, alas, an orgasm drug is still a dream.
As soon as I drained my balls, I pulled out, and the old, familiar shame washed over me. I hurriedly pulled on my boxers and shorts without even cleaning off my cock. MarriedCD stood up, pulled a rag out of a desk drawer and started wiping the cum dripping down his thighs. He was still wiping when I started heading for the door.
“Let’s chat later on Grindr,” I said.
MarriedCD nodded without looking at me. I had been right– he did cum. His love juice streaked the side of the desk. He was cleaning it up when I closed the door behind me.
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It’s official, guys. I am on a major porn-and-hookup bender. Publishing that last story was a major trigger for me. I loved reading the comments and emails I have received. Knowing that so many other guys are into the same thing as I am is a huge turn on. When I get like this, I am totally out of control. In the two days since the story went online, I have sucked two dicks and fucked one guy up the ass.
And I am not done yet.
One thing I’ve noticed is my benders keep getting longer. When I first started hooking up, I would jack off with a dude and quit for months. The shame would be too much, and I just couldn’t bring myself to start looking again. Now jack-off sessions hardly even seem like cheating anymore, and my benders go on for days, sometimes weeks. I think this one is going to go for a month or more.
Sometimes I am asked if I am a top or bottom. The truth is that I am totally versatile. What matters most to me is that there be what I call a “feminine presence” while we hook up. That usually means the other guy, myself or both of us need to play the role of the woman. Panties and lingerie are often involved but not always. It isn’t necessary to look or sound like a woman. It’s more about channeling feminine energy. Some guys get it, some don’t. Those who do usually make for good hookups.
Porn is also very important to me. I need to warm up with it before hookups, and I love to have it playing during them. A lot of guys like gay or bi porn, but I have a strong preference for straight and transsexual videos. I love the idea that my hookup buddy and I are becoming the sluts on the screen. I have a wide range of porn tastes, most relatively vanilla compared to what’s out there. Stripteases, blow jobs, pussy fucking, anal, cum shots and bukkake all work for me.
I’ve been logged into Grindr while writing this, and my phone has buzzed three times in the last five minutes. It’s time for me to go, but keep the comments and emails coming. Faggots like us need to stick together.