Stories

After-Hours Hookup with a Trans Lady

Man Undressing Woman

It was 4am and we’d just finished closing up the bar, which meant I was pretty drunk and ready to keep my buzz going for a few more hours.

“Let’s go to that after-hours again!” I shouted at John, my friend and co-worker, as we drank down our the last dregs of beer.

“Oh forget that, I’m heading home,” he managed through a burp. We locked up the bar, punched in the alarm code, and headed out into the night.

“Stay out of trouble” was the last thing he said to me as we parted.

“Ha. Yeah right.” 

I found myself at a familiar after-hours booze can, where I was raring to sneak in a couple games of pool with a few more beers before sunrise. The spot was located at the end of a seedy alley, down a dark flight of stairs. The doorman met me with his usual grim cheerless stare, with his hand held out for the cash. I nodded, shelled out the twenty bucks, and headed into the basement.

A thick cloud of cigarette smoke and sour waves of spilt beer hit me dead in the face. My eyes began to water as they adjusted to the gloom.

I grabbed a beer and a shot at the bar, and headed over to the crowd around the pool table at the back of the room.

That’s when I noticed her. She was leaning over the table aiming at a ball.

From behind I could tell she was super curvy, and her skirt was hiked up just below her voluptuous ass. In the front there was a distinctive bulge that set my mind racing. I’d watched trans porn, and had fantasized about being with a trans woman, but I didn’t know if I was ready to make the leap from fantasy to reality.

Her wavy dark hair fell to the small of her back. She pushed a tendril out of her eyes to make the shot. She sank her ball. Then she stood up and turned around. I held my breath when her eyes met mine. And then she smiled.

Play it cool, I thought to myself, taking a swig of my beer. She walked around the table holding my gaze, and slowly leaned in to sink the eight ball. She definitely had game! The muscles of her arms flexed, as she fired the ball into the corner pocket. Game over… for me.

I found myself walking up to her, hoping to catch that smile one more time.

“Nice shot,” was all I could muster.

“Thanks” was her reply, with traces of a Latin accent.

Smiling now, she leaned in closer and asked if I wanted to play a game. Her husky and rich voice sent tingles up my back. I told her I’d love to play, but asked what the stakes?

Closer to me now, she whispered, “If I win, you take me into that back corner and give me a rub down.”

“And if I win?” I gasped, her fingers tracing my side just above my belt. “What happens if I win?”

She winked at me and smiled.

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