Wig Stories

6,038 results
Orientation
Length
Source
Infinite Scroll

The Rest Stop

by Skimpylilpanties on Sep 16, 2017
Transsexuals & Crossdressers

I was sitting in my dorm room one night bored as ever. I so wanted someone to chat with online, but there seemed to be no one interesting as usual. Just random bots and webcam offers that annoy the shit out of me. Now I enjoy talking to women and having sex with them, but I also have a passion for being one. There is something so great about dressing as a g...

How I Became Alison

by JayDeviant on Jul 10, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I was just getting used to the fact that I was a gay slut, when things really escalated way out of my control, in ways I could have never imagined. It was due to Mister Spandwick, an old man whom I had met through some friends-of-friends. I was used to the fact that old men found...

Glass Bauble

by AlexiaAlexander on Dec 10, 2018
Transgender & Crossdressers

Being secretly Transgender in a rural area can be frustrating. I live a life of quiet desperation and a whole lot of masturbating to porn. Reading and watching transformation stories stir my imagination for my own dreams. Finding a weird glass purple gem allowed dreams to become reality. It all started at the Flea Market. I was really on the low money side...

Arabian Nights Pt. 02

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Michele remained tied to the chair, covered in semen, defiled and confused. She isn't stupid; she knows that she has been kidnapped and is being held as a sex slave and knows that there is going to be worse to come. The door opens. A voluptuous dark-skinned woman enters; her heels click-clacking on the tiles. She is tall, at least six feet, she wearing a bl...

Choose Your Costume Wisely

by Bethyboo on Sep 14, 2017
Erotic Couplings

Happy fucking Halloween. That was his thought as the alarm bell clanged this cold autumn morning. A costume, where the hell was he going to find a costume on Halloween day. The memo from the office booster club arrived in his inbox at exactly 5:55 pm last night. It was a lucky thing he even saw it. What the hell were they thinking springing a costume day a...

Cockatoo Pt. 26

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

Shane's lips brushed mine so gently I wasn't sure he had kissed me at all, as if he was still giving me the chance to back out. I closed my eyes and pressed my lips onto his and I felt the pressure increase and we were kissing properly, his lips crushing mine. I felt lightheaded, and the blood began to pound in my ears as I felt his arm pull me closer. I hes...

Caught For the Last Time Ch. 07

by TGJamie on Sep 15, 2017
Transsexuals & Crossdressers

We awoke in the morning almost identical to how we both fell asleep. I was still in the babydoll nightie she had given me and she was still in her palazzo pants, heels and pony tail, and no top. "That was quite a night," she said as she sat up and unstrapped her heels. "When was the last time I woke up with heels on?" We both laughed as I shook my head. Th...

Our Dinner with our Hostess

by wifestoy on Sep 16, 2017
Transsexuals & Crossdressers

After a very relaxing bubble bath I shaved Renee's legs and her sweet pussy, she gave me some pampering and shaved me. This was a real treat. I got a very sweet reward by Renee. She allowed me to eat some serious pussy after the bath. As we lay down on the rose petals the soft skin and mix of fragrance from the bath oils and rose petals was intoxicating. I g...

Jimmy Olsen Shemale Bimbo Ch. 01-02

by tawnysuede on Sep 17, 2017
Celebrities & Fan Fiction

Chapter 1 - Junior reporter on the job! Jimmy ran the brush through his shoulder length hair one more time and stepped back to admire himself in the full length mirror. The wig looked good. It was the same wig he wore each time he dressed up. He took the cap off of the lipstick tube and applied a generous coating of the scarlet wax to his lips, and then bl...

On Display: A Mannequin Fetish Ch. 02

by Chameleongirl on Sep 2, 2017
Fetish

Michelle was a model employee at Vivienne's Boutique and had worked her way up to assistant manager. She enjoyed the store discounts, especially the new lines of clothing and arrivals for each season. It was easier to stay in fashion, and she didn't have to spend as much of the money given to her by her parents, who strictly forbade her to work during her st...