Ladyboy Fuck Guy Stories

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Barrack Room Betty Ch. 14

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fourteen – Supergirls Bangkok "I've fucking had it with Jason!" Michele spat at Rod Latham "That fuckwit tracked me down and found me in a bar in Naples and created an absolute shitfight. And every night I'm here in the club he carries on like a petulant child whenever I work a punter and in particular Lieutenant Steve Winters who is one of our...

Friend in Need is a Friend Indeed

by StarfireMayo on Sep 12, 2017
Loving Wives

Episode eight of the erotic photo journals of an English Teacher in Thailand. * Noi held me tight. I felt her warm body press against my back. I counted myself very lucky indeed to have settled down with this particular girl. Noi is always very attentive, loving, and obedient. Thai women are very shy and prude in public, and make up for repressing their e...

Shemale Orgy

by xploring96 on Nov 14, 2017
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. Feedback on my stories is always appreciated. ***** All Ron could think about while he stared into her sultry eyes with their smoky dark eyeshadow was, how lucky I am that I am a faggot....

My First Ladyboy Ch. 02

by 69plus1 on Sep 19, 2017
Transsexuals & Crossdressers

We had just fucked ourselves senseless and Billi was leading me to her shower. After she adjusted the temp we got under the spray. First off was to clean my cock of the lube and cum. I leaned back to the shower wall and spread my legs like a slut as she covered me with soft soap from cock tip to balls and back to my ass. I was sexually spent but she easily...

Seduced and Hoodwinked Ch. 05

by walterio on Jan 10, 2018
Transsexuals & Crossdressers

AN EROTIC SUNDAY On Sunday morning Darin woke up with Nin and Lawan in bed with him. They were on either side of him and he had his arms around them. As much as he would have liked to fuck them before he got out of bed, his bladder was ready to burst. He made his way to the bathroom and took his morning piss. After peeing and washing, he returned to his bed...

My First Ladyboy

by 69plus1 on Sep 19, 2017
Transsexuals & Crossdressers

I was in my forties and was bored with life. My job sucked, my night life was the same over and over. Bar hopping hoping to get lucky and pick up some woman who would fuck me and not be crazy in the morning. Or maybe a hot guy just for the change of pace. Guys were just about the sex and usually didn't bring any baggage. So I was surfing the internet and ge...

Jamie's Descent Pt. 04

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

Fiona stood in front of me and said sharply, 'Stand, slut!' It was a tone of voice that made you think arguing about it wasn't such a good idea. I got up as quickly as I could, nearly falling over in my haste to obey. The tip of her pink tongue appeared and slid along her full lips. She had seemed tall before, but now she towered over me. I saw that someho...

Delectable Debbie

by Pussrider on Sep 16, 2017
Transsexuals & Crossdressers

I can't explain why it was that I fancied having sex with a transsexual. I mean I'm a perfectly normal happily married man, couple of kids, mid-40s, a stone or so overweight but reasonable looking, my own hair and teeth and everything. I must admit, I've been with one or two...escorts, hookers, whatever term you prefer, over the years, but always very womanl...

Cockatoo Pt. 10

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** We woke early as Alex had to be at the airport to catch the flight with Kritsada at 7am. He was going to pick Alex up from the flat in his car as he headed off to the airport. I was going to follow a bit later as I had to collect Samantha from her flight for our planning meeting. I lay in bed and watched as Alex got ready to leav...

Surreptitious Love Ch. 57

by BenGarland on Sep 14, 2020
Erotic Couplings

CHAPTER 57 -- A NICE SURPRISE Nguyet asked me last Monday short and crisp—using her full name again from her office email—if I was interested in another meeting with her. We had role-played that I was interested in the cookie-cutter houses her company was selling, and the first house viewing—our last role-play—had turned into a two-hour-long ribald rumpus,...