Tranny Fuck Story Stories

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The Evolution of Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

My beloved Tranny G was so devastated by the one night stand and had lost her confidence. First she was made fun of while shopping, ending the evening with the "perfect" man, having her first true intimate experience with a man, only to find that his promise to call her was false. I did not see her on my last trip, as she was devastated and in her own lovi...

Recruiting of a Sissy Maid Ch. 14.5

by Sissy_Chantel on Dec 16, 2017
Transsexuals & Crossdressers

Readers, I am adding another quick short story of tranny girl Bailey hungry for men and cock. Inserting this story between Chapters 14 and 15 of "Recruiting of a Sissy Maid". I hope you all enjoy it. ***** Title: Another T-girl Bailey out and on the Prowl for Men and Cock Story Friday night, I've been feeling a desire to dress up as Bailey all fucking day...

Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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A One Night Stand for Tranny G

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

The time had arrived for me to travel to see Tranny G, yet something felt different. I mentioned that HE is a soldier and really, I was never angry about the rape. It was such an experience, that I wander back to and repeat in my mind again and again, wet with the memories of the fear, the fight, the ultimate pleasure. I might as well tell you that I see mys...

Tranny Tales Ch. 02

by erectus123 on Sep 15, 2017
Transsexuals & Crossdressers

The use of the word Tranny is not meant to be disrespectful; it is used as it was in the past although not politically correct at this time. ***** There is a rare moment during an eclipse when the sky turns dark red and winds seemingly gather together from nowhere, as if to celebrate the celestial event. I had come from a business meeting that ran late tha...

Tranny G, Gang Bang Queen, 5

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I apologize - I had no idea I would continue to write about Chris and Tranny G or I would have numbered the stories. These two beloved people are so rooted in my life and there is so much to share. I never imagined I would share these stories with anyone. Since my husband and I became swingers, I had no idea what my interests would be, I just simply plunged...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

There's Something about Sarah Ch. 06

by MicheleNylons on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Six - Tina Tina drove me back to the Holiday Inn and we kicked off our shoes, put up our feet on my bed and lit cigarettes. I had poured us both a tumbler of Jack. We sat upright with our backs against the cheap headboard. "That wasn't so bad," Tina said. "Sloane looks fat," I replied. "Ouch! Bitch!" Tina laughed. "'You're the celebrity around...

I Wanna Both His Balls

by enfantterrible on Sep 14, 2017
Humor & Satire

The Brooklyn mob boss Joe Slow is sitting in Carlito's slurping on a bulging bowl of meatballs. The restaurant is dark and empty, just the way Joe Slow demands it everyday at the same time. A mobster with a habit like this is a Hitman's dream, but that's another story. So we see the scene and tomato sauce is smeared all around Joe Slow's fat chops, which fla...

A Sissy's Wish List

by slutty_lucy on Sep 16, 2017
Transsexuals & Crossdressers

Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how to best share my desires. I want to be a perfect little slu...