Husbands First Tranny Cock Stories Stories

349,686 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Virgin Tranny & the Bride Ch. 03A

by yano on Sep 25, 2017
Transsexuals & Crossdressers

I’m still awaiting the next instalment from Roberta which seems to be as eagerly awaited by many of you too. May I thank you all for your interest, and also for your votes. In the meantime I have decided to write, in her absence, what I think Roberta, Margaret and John did. Here is chapter 3A of the The Virgin Tranny and the Bride. Hope you like it. By...

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...

Tranny Tales Ch. 03

by erectus123 on Sep 15, 2017
Transsexuals & Crossdressers

Maxie: The Tale of the Exploding Penis 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. ***** Did you ever see the old film, "The Tattooed Man" or maybe it was called" The Illustrated Man?" Was it Rod Steiger who stared in that film, I really can't recall anything...

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...

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...

Dream Bride Tranny Ch. 03

by yano on Sep 13, 2017
Transsexuals & Crossdressers

I was never allowed to forget that I had had sex with my 18 year old niece when she modelled a few bridal gowns for the KBG. Even her wedding day was hijacked and, in the final part of a wedding day shock for bride Kirsten, she has dressed her Uncle in her most amazing bridal gown and is about to embark on another kinky adventure. Hand in hand Kirsten and I...

A Few Notes from Mindy

by mindyrose on Sep 17, 2017
Non-Erotic

Dear Literotica Readers: Some random thoughts, in no particular order, about my story that don't seem to fit into my narrative but should help you know me better, which should help you understand the themes of my transition stories... Thank you to all of the people that have left me positive comments. I haven't been writing the stories for public approval;...

Filipina Cuckolds Her Sissy Husband

by nancyvasquez on Sep 14, 2017
Transsexuals & Crossdressers

If there's anything more sexy and exciting for a closeted sissy than dreaming about being a woman on your knees getting ready to serve a big black muscleman, it's actually having the balls to go out there and make it a reality. It happened to me! I was married, to a hot sexy girly-girl Filipina. When we got married I was still trying to be in denial about my...

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...

A Glory Hole for Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each days, growing into text messages each day, and more. No idea...