Sex Stories About Picking Up A Tranny 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 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...

Master is Going to Cum Now

by Manndee on Apr 28, 2020
Transgender & Crossdressers

I had searched online for months to find a friendly like-minded group of people that I could communicate with and share my unique desires. I thought I had seen them and signed up to several dating type agencies that offered me the perfect match. The agencies then sent me non-stop emails from people that matched me. The people were not interested or simply di...

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...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

Birthday Surprise

by vinyldolls6666 on Sep 16, 2017
Transsexuals & Crossdressers

My girlfriend and I have the same fetishes and interests for the most part. We both find latex irresistible. We love the site of a tranny with a big cock. Robbie knew everything about me. For my birthday she went well out of her way to make me happy. The date rolled around. I figured it was just another birthday. I Thought nothing of it. Another year with...

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;...

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 Young Man's Sexual Odyssey Pt. 02

by erectus123 on Sep 16, 2017
Transsexuals & Crossdressers

Note-All characters are mature adults who participate in consensual sex, there is no sexual violence and all scenes conform to Literotica guidelines. * A Young Man's Sexual Odyssey - a 3 part series Part One -The Faithless Fiance and The Spider Gals Part Two -The VibratingTranny Hooker Part Three -The Korean Love Fandangle * Note - this is the second...

Twenty Questions

by DrLuverotica on Sep 19, 2017
Transsexuals & Crossdressers

THURSDAY I was just settling down to watch a movie when my wife arrived home after a night out with her girlfriend's. "You're home early," I said. "Lucia had to be back by ten. She's on the early shift." "Meet anyone else?" "Just a couple of hunks - they're coming over for supper later." "Very funny." "Actually I wanted to come home because I was feel...