Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

PARTYBOY and His Bitch Wife

by Goddess_Meanie on Mar 13, 2018
BDSM

I'm didn't take the time out to describe myself. I often skip over my features. They are both a gift and a curse. Young girl, very timid, secretive and shy. Early masturbator, enjoyer of porn and as my youth went about, and more and more aggressive, into my teen years. At that same time I found boys to be boring as hell, and always needing to be led. I had a...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

Confession Pt. 04

by holukukkar on Apr 17, 2019
Transgender & Crossdressers

We both were lying on the bed naked, when I felt a kick on my back on turning I noticed that Shivani was hitting me, when I asked her "what happened?" Shivani:- We have a long day today. Me:- Means? Shivani:- We will be going to some place and have many things to do. Now sleep and wake up by 11:00 AM and then wake me up by licking me and then we have to g...

From Submissive to Slave Pt. 01

by HerBetaBoy on Sep 25, 2017
BDSM

So I sat there, my wrists and ankles bound to the chair I was sitting in. My mouth forced open by the pink ball gag wrapped around my head. My cock, as pitiful as it looked at the moment, was locked in its cage covered by pink lace panties. The view in front of me was both humiliating and exhilarating at the same time. My wife of 4 years was on her back, her...

Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...

Rediscovery

by Nyccd on Jul 10, 2018
Transsexuals & Crossdressers

Summer was winding down to a close. I had just finished my sophomore year of college and decided to take the fall semester off to work and save some money before I continued. I decided to work twelve hour shifts at the university lab to give me some free days during the week on which I could delve into my true desire: crossdressing. Having just moved back i...

A Latex Trap

by Lifeinlingerie on Sep 21, 2020
Fetish

I had been perfectly set up. All the pieces fell into place, and I followed each part of their plan as if I'd had step by step instructions - all leading me to my current predicament. To set the scene... I am currently tied to a soft, red-leather covered bench. My knees, thighs, and arms are bound and clipped to the frame of the bench. I'm wearing a bright...

Slave Ch. 09

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: This is about a bisexual submissive man and his journey as he explores his sexuality. I put it in the fetish section because that seems to be the best fit. There is piss and scat. There is bondage and crossdressing. There is fisting. There is group, gay and bisexual sex. There is non-consensual and reluctant sex. There are even elements of reali...