Tranny Stories

1,301 results
Orientation
Length
Source
Infinite Scroll

Erin & Jeremy Ch. 03

by JDay on Sep 16, 2017
Novels and Novellas

Erin & Jeremy Chapter 3: And She Thought The Ride Was Over . . . Author’s Note: I would again like to thank agirl2envy for her help in this project. The name has remained changed to protect the sexy one. Erin sped up as she pulled on to the nearly deserted road. As she drove, the events of the last few days replayed themselves for her: Meeting her cyber-l...

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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...

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A Tranny Virgin No More

by Creamyirish on Sep 12, 2017
Transsexuals & Crossdressers

Fantasy became reality for my gal, Tranny G. She has finally started to come into her feminine persona. She has more confidence, is buying more outfits, and when she leaves HIM at work, she comes home and dresses. She starts with wearing short skirts and cami's, then sexy lingerie at night. She began playing with make-up and based on tips I gave her by e-mai...

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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...

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Tranny G is a Nymph

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

It has been a long winter and I have not seen Chris or Tranny G in a long time. Chris lives in a place too cold and it is difficult for him to travel. During those cold months, and without my being near, G has been in hiding. I have hinted, begged and pleaded with Chris to find a weekend to travel to see me. He needs a break from work and the cold and I need...

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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...

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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...

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TS Madison Simply Rocks!

by Samuelx on Sep 16, 2017
Celebrities & Fan Fiction

African-American porn legend, amateur Rapper, YouTube sensation and all-around brilliant entrepreneur Brian Pumper smiled smugly as he slid his long and thick ebony dick into Lethal Lipps tight butt hole. The big-bottomed, caramel-hued porn starlet with the infamously thick, luscious lips and ever-hungry pussy purred contentedly as Brian Pumper's big dick fi...

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Tranny Fantasy World

by panopticind on Sep 15, 2017
Transsexuals & Crossdressers

If I were not afraid of shame and assuming practicality is no issue, I'd turn myself into a piece of fuck-meat for well-hung trannies. I'd have an army of the world's most beautiful and well-hung chicks with dicks living in my mansion. I suppose they'd receive a salary as an employee of mine and not be slaves or something. But I'd say I'd need about 500 tran...

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Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

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