Chastity Tranny Stories

8,131 results
Orientation
Length
Source
Infinite Scroll

A Very Special Club

by LorenzoAbajos on Aug 31, 2017
Group Sex

We met at a different house every time the club met. We might meet only once a month with all the members, but some members would meet in smaller groups more often if they cared too. We were young and old, male and female, beautiful and average, gay and straight, and we all loved masturbating. It had all began slowly, of course. I was the instigator. I love...

Sub Rosa Ch. 02

by Margotcul on Oct 6, 2020
Transgender & Crossdressers

3. Needless to say my night was -- again -- troubled. I removed and cleaned the vibrator before I went to bed, but the cage remained in its place. I woke up numerous times during the night to painful erection attempts. After my second night with little sleep, I was in ruins. I got out of the bed and left my bedroom. There was no sign of Mael yet. I did my...

The Virgin Tranny & the Bride Ch. 03A

by yano on Sep 25, 2017
Transsexuals & Crossdressers

I’m still awaiting the next instalment from Roberta which seems to be as eagerly awaited by many of you too. May I thank you all for your interest, and also for your votes. In the meantime I have decided to write, in her absence, what I think Roberta, Margaret and John did. Here is chapter 3A of the The Virgin Tranny and the Bride. Hope you like it. By...

Mistress Dusty

by justincbenedict on Sep 15, 2017
BDSM

BUTTERMILK BOWL (possibly Sadistic Spouse in Buttermilk Falls) "But I've not cum in six weeks, Dusty" Crake Ingledew said to his demure spouse. Dusty looked up from her "Cosmo" long pink nails tapping an article discussing depilatory body hair removal. She is so beautiful! Crake thought. Languid hazel eyes with long lashes, the dark eyebrows frowning irrit...

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...

Cherry Popped

by Koth19 on Sep 11, 2017
Transsexuals & Crossdressers

I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I met a very beautiful woman. She was tall and slender with b...

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...

Emily and Steve Ch. 09

by Travel_by_day on Sep 16, 2017
Transsexuals & Crossdressers

Over the next few weeks things really started to settle in at work. Emily was being more than accepted, she was being lauded. Emily, feeling much more comfortable as a woman, started being a much better worker. The quality of work that Emily was producing was far superior to Mike's work. She was featured on the company's intranet site as an inspiring story....

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...

The Superbowl Party

by justincbenedict on Sep 14, 2017
BDSM

Scrip didn't get Marigold. First she'd asked him to bring home other men for threesomes, then she'd told Scrip, after a few session that she didn't want him to participate. Really, but to "just watch" which was fine with Scrip, as it seemed most of the time when there was a three-way. Marigold did almost all the sucking and attention on the other guy while...