Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Finishing School For Ladies Ch. 08

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

Chapter Eight -- Passport To Eternity "So are you seriously thinking about getting tits?" Sally dropped her newspaper and snuggled up to Valerie. "But I thought the whole tranny deal was only for two or three years? Just until Tony stopped looking for you?" Sally said inquisitively. "Well it was. But now I don't want to live any other way. I can't tell yo...

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...

A Surprise Stripper for My Birthday

by dirtyjoe69 on Sep 12, 2017
Transsexuals & Crossdressers

\ My wife and I have always been a little on the kinky side. We have been swingers for seven years and have done many wild things during this time. Every Friday night we have a thing called dirty night where we go up to our room and watch two of our favorite shows Bliss and Kink. Bliss is a weekly series that has mild erotica in it aimed at couples. Kink i...

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...

Open in Reader

Black Couples Love Tranny Girls

by Samuelx on Sep 16, 2017
Toys & Masturbation

How does a brother like me gets into these situations? That's what Haitian-born Canadian stud and Carleton University student Jean-Claude Etienne asked himself as he lay on the king-sized bed, getting his ass filled with cock. The cock in question belonged to Trina Ishtar, a gorgeous Transsexual lady whom his girlfriend Evelyn introduced him to. Evelyn, a ch...

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...

Surprise, Durprise!

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

1 - Surprising an old friend It only started out about a year ago. Actually, really, it was much longer ago. But two years ago things REALLY got going. It was when Mike, my brother-in-law, asked me to have a look at his computer, the CDR wasn't doing what it should. So one evening when his wife, my wife's very best friend and business partner, was visiting...

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...

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...