Shemale On Guy Stories

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Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Amanda and Me Ch. 03

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

The sudden ringing of my alarm clock woke me up at 6:30AM sharp. Rolling over I turned it off and then rubbed at my eyes as I began to wake up. Slowly the events of the night before came back to me and I smiled as I thought about Amanda and how wonderful another night with her was. We had great conversations and another round of mind-blowing sex and I wonder...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

A Night with a Sexy Shemale

by MajesticLVR87 on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story which goes deeper into my explorations of my sexuality in my younger years many people may not have the guts to share so much about their past I don't have that problem because I have met the love of my life and plan on sharing the rest of my life with her my adventures with other partners or random partners is over I have settled down s...

Since that day....

by Ssrd33 on May 5, 2019
Transsexual

The weekend I finished and my whole body felt heavy, my ass felt more open and empty at the same time, I slept all the rest of the day. The next morning I woke up and had Melany's penis full of milk, I took it out and I felt that my mouth was very sticky, I went to the bathroom to take a shower because I could only smell the semen all over my body. When I ge...

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Amanda and Me Ch. 02

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. As I lay there thinking about the night before I was surpris...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

Male or Shemale, Still a Slut

by yeaimbored on Sep 11, 2017
Transsexuals & Crossdressers

So this is a 2 part story. Part 2 is strictly shemale and takes place a few years after Part 1. Part 1 is how Brandon became Brenda, although without the "I took bath and did my nails and shaved" stuff because that's not my thing. It's more tranny sex than anything, so if you're only looking for full on shemale skip to Part 2, they're pretty much standalone...