Literotica - Couple Surprised By Tranny In 3-some Stories

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The Path to Happiness Pt. 09

by brendachaplin2000 on Sep 28, 2020
Transgender & Crossdressers

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman". On a positive note David had started a relationship with Adam, and...

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...

Wife catches husband doing what!?

by Storymaster252580 on Jul 14, 2020
Fetish

Jeff and Lauren have been married for 3 years now. They met in college and dated for 2 years before eventually getting engaged and married. They are a fit and active couple always going to the gym. Jeff is 6-1 200 lbs and has a six pack and is packing a nice 8 inch cock. Lauren is 5-5 130 lbs with nice perky C cup tits and a firm round ass that gets all the...

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...

The Ballad of Barry

by AngelaK on Sep 16, 2017
Transsexuals & Crossdressers

Part 1 - The young man Barry was in his early fifties. He stood about 6ft-1, and weighed nearly 300 pounds. He had brown hair going to gray, and green eyes. In his youth, he'd been considered handsome. Barry was also very lonely. He was struggling to cope after the loss of his wife nearly five years ago. His wife of 25 years was a companion he sorely misse...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

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...

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...

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...

Self Service Ch. 05

by prickasso on Sep 12, 2017
Illustrated

It was 3 weeks since the party where I performed in front of 2 dozen transvestites, sucking my own cock until I came. After that, Sonja, one of the she-males had propositioned me to film this as an instructional video for a porno company she worked for. I had just received an e-mail message from her company saying they would pay me a pretty good figure for a...