Tranny Surprise Erotic Stories 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...

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...

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;...

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...

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...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

Married to Anonymous

by storywriter2018 on Aug 29, 2019
Erotic Couplings

Vic and Marie had been married 8 years. They had 2 kids together and both worked full time jobs. Both in their mid thirties, they stayed in shape by going to the gym a few times per week and ate healthy. Their sex life was once very robust but was down to 2-3 times per month. It wasn’t that they weren’t attracted to each other. They just were both busy and t...

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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...

The Benefit of Plasma Television

by Kitkat103 on Sep 12, 2017
Toys & Masturbation

MaloMarz6969 -- Lol what a freaking idiot. So what are you up to? Sbarron85 -- Just waiting for Matt at his place. He is supposed to be working late. MaloMarz6969 -- Aha. I did not know that office drones had to work so late, honey its 11pm! Sbarron85 -- I know that, what are you implying? MaloMarz6969- Well I think he is out too late to just be desk joc...

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...