Wig Stories

6,038 results
Orientation
Length
Source
Infinite Scroll

The Wig Ch. 2

by Stormbringer on Sep 12, 2017
Loving Wives

"I'm worried about Candy honey," said Cindy into the phone. "I'm going to stay here until she shows up. I might not be home until morning." "Just remember," said her husband Larry. "Don't give her any more money." "I won't," replied Cindy hanging up the phone. After fucking the stranger, Cindy had showered and changed back into her dress. She had returned...

The Club Pt. 02

by RubberBudcus on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 2 First Night I spent the rest of that day sleeping and eating and the maid came and went at regular intervals. I felt no hostility towards this thing that served me but was irritated that it would not speak to me at all. It kept putting a finger to its lips and, at one stage, I really felt that it wanted to speak but couldn't for some reason be it...

Not Fantasy

by archchancellor on Aug 19, 2017
Exhibitionist & Voyeur

Recently I did a show in the south east that required a stage costume of sorts. So I chose a top hat, wig, and was going to wear either a woman's black bathing costume or black panties under fishnet tights, heels and some kind of top. Great giggle except it turned out it would be a family show, lots of small children, and a problem with an unexpected result....

Becoming Cassie Ch. 06

by TGJamie on Sep 18, 2017
Transsexuals & Crossdressers

I was walking across campus, kind of still in a daze from the Halloween party a week ago at the Warren's and singing White Rabbit when my cell phone rang. "Matt, is that you? Hi, it's me, your cousin Kate." "Wow, I didn't expect a call from you. Where did you get my number?" "I called your house and talked to your mom today and she gave it to me. I hope i...

Waited Too Long and Lost Everything

by Jayden_1 on Jan 6, 2020
Interracial Love

This story is motivated and inspired by a real event. The names of the characters have changed, but these are real individuals and a real event. ***** Liam lives with his mom and dad in a ghetto in Los Angeles, California. He is 20 years old and studies in college. He had studied hard all year and now it was finally Christmas break and he would be free fr...

It All Started... Ch. 02

by trixie38cd on Sep 18, 2017
Transsexuals & Crossdressers

When we got home, Dina told me to take a shower, get dressed again, in clean women's underwear and wig. "Go wash the cum off yourself, for Christ's sake. You won't need makeup, just tits, hair, bra and garter with stockings. No panties, I want your clit hanging out so I can see it while I talk to you." I returned to the living room, where she had a drink an...

Freddie Becomes a Cross-Dresser Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

Now, that I bought everything that I needed to transform myself from a handsome and modest man to a beautiful and sexy woman, I realized that I had completed the easy part in buying the clothes, the makeup, and the perfume. The difficult part, of course, would be dressing up like a woman without having a woman there to help me. I certainly did not want to as...

Jail Bait

by Deborah on Sep 1, 2017
Humor & Satire

by Amazing Grace (a/k/a Deborah) My entire family has spent at least some time in the slammer, except my mother; she's dead. My older brother James is a transvestite and got busted for soliciting which caused him to become the black sheep of the family (see the story “A Maze & Grace”). Doing hard time is one thing, dressing up like a girl and sucking cock...

Kitty's Debut

by emmakaufmann on Sep 15, 2017
Fetish

"Oh Kevin, how many times do I have to tell you – red and green should never be seen," said Jade, dropping her carrier bags on the floor. She watched as Kevin, who had been lounging in an armchair, his legs propped up on the coffee table and his knuckles grazing the floor like a gorilla, jumped to his feet. "Didn't hear you come in," he said, pulling at t...

My New Life Ch. 02

by quietguyin_tn on Sep 16, 2017
Transsexuals & Crossdressers

(Thanks to all for the positive feedback and encouragement.) My head was buzzing, I could hardly think, let alone feel and sort through all that was going on in my mind. Had I really just played with and sucked a dick? Waives of shock passed through me, am I gay? What the heck is going on? In a short time it all turned into laughter. What does it matter?...