Tranny Gloryhole Literotica Stories

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A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

A Cuckold's Tale

by CastleDJK on Sep 14, 2017
BDSM

Based on Chaucer's Canterbury Tales Prologue Three Mistresses are lounging around the pool, chatting and laughing, while their three sissy maids stand by to attend to them. Big breasted in a white string bikini, redhead Mistress Reeve is enjoying a foot massage from one of the sissies at the side of the pool. Lady Night, raven-haired with an alabaster whit...

Brittany's Holiday Encounter

by cdbrittany4bbc on Sep 12, 2017
Transsexuals & Crossdressers

I will start off by saying that I am a 42-year-old married, successful businessman that travels four to five times a year each trip typically last three or four days. And did I say I am a closet cross dresser? I've never ventured out in public- and I don't maintain a dressing stash or keep any clothes at the house. If caught I would most likely lose everythi...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

The Gloryhole

by wizard666 on Sep 13, 2017
BDSM

Brad and Janet had been together for many years and although they had an open relationship, they had never been to a party like this one before. As they drove to the house, Janet was trembling in nervous anticipation. She had never done anything this adventurous before, but despite her fear she could still feel the excitement building! Janet had worn a slink...

December Diary

by Benny024 on Sep 1, 2017
Group Sex

What started out as an innocent lark - a so-called Christmas present to myself, turned into an uncontrollable, sexual inferno. My sexual desire and lust could not be satiated the month Christians celebrate the birth of baby Jesus. My sexual odyssey, during this timeframe was not intended to be sacrilegious. It was just a co-incidence or so I thought. Anywa...

Gloryhole Addiction Ch. 02

by Brittni4u on Dec 19, 2018
Fetish

It has been a several years since my dirty yet amazing gloryhole experience. At that time, I was 18 years old and still in high school. It was supposed to be a sneaky one time experimentation which turned into a nine month long, multi-visit, wonderful cock sucking experience that has never left my memory. I have always had an oral fixation when it comes to...

First Time for Everything

by qazwaz on Sep 12, 2017
First Time

My wanting cock throbbed around my hand as I glanced down at my illuminating phone in my dark car. "Just got here" I replied, before switching internet tabs to the previously-loaded video of a blonde girl in a gloryhole. I had a long drive that day, about 3 hours to my hometown destination. Having broken up with my girlfriend a few weeks back and not having...

After School Ch. 02

by Faye_Skylark on Sep 25, 2017
Erotic Couplings

Crystal McLaren stood anxiously in the cramped backroom office of the local adult book shop. She could never quite work out why they were called book shops, since they she didn't see many books in the store. Instead it was mostly filled with adult DVDs, toys, outfits and miscellaneous products. Crystal was eighteen years old and a student in her final year...

Date Night with My Wife Pt. 02

by amadbaker on Aug 31, 2017
Group Sex

As we entered the bookstore we realized how late it had become, without noticing it was already after 2 in the morning. That was OK since our favorite store is out away from towns and city's so it doesn't get more than trucker traffic and since it's the weekend there are not a lot of them out and about. Shawn and I were following my sexy wife Debbie around w...