Wig Stories

6,038 results
Orientation
Length
Source
Infinite Scroll

The Landlady's Bedroom

by Lolli on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story that happened to me a few years ago. I was working in a small village down in Devon and was lodging with a woman in her early forties named Elaine. Elaine was very attractive for her age and she had many younger friends that were about my age (23 at the time). I got on well with Elaine and often thought about having sex with her if the o...

Please, Please Me!

by Harddaysknight on Sep 17, 2017
Loving Wives

"Please, Clint, please?" Barb begged as I prepared for bed. "I promise no one will know I am even there! I can get my mom to take care of Cindy and Kyle." "Barb, the boss was extremely clear on this. He wants no wives anywhere near this convention. He suggested that he would fire anyone that brought their wife," I responded. "I know you always wanted to see...

The Wig Ch. 1

by Stormbringer on Sep 12, 2017
Loving Wives

"I need help. I'm in trouble. Please come to my apartment," said the voice on the answering machine. Cindy sighed. It was her twin sister Candy's voice on the machine and it wasn't the first time she had called for help. However, there was a certain desperation in her voice this time. The two sisters were physically identical in every way, but not in perso...

Michele Nylons' True Stories Ch. 04

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite. This is the story of my latest encounter,...

Journey Through the Rabbit Hole

by NymphWriter on Sep 19, 2017
Erotic Couplings

I learned a long time ago, that life doesn't always turn out the way you plan or hope, and sometimes you've just got to roll with the punches. But for me to tell you my strange and erotic story, or as I jokingly call it, my "journey through the rabbit hole," you need to understand how I got to this juncture in my life. Robert Falcone and I were married just...

The Seduction of Peter

by airoralover on Sep 25, 2017
Transsexuals & Crossdressers

Peter stood at the front door of his parents' house and waved goodbye to his mom and dad as they drove off in their car to the airport and their two week vacation in the Caribbean. He closed the door behind him, ran up the stairs to his bedroom where he stripped off his jogging bottoms and tee-shirt and hurried into his bathroom. He had the house to himself...

Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

Sweet Alice

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

It is typical in these sorts of confessional stories to change names to protect the innocent, but in this case the concept of 'innocence' barely applies. That said, I will refer to my friend here as Sweet. If you're old enough to remember the singer Matthew Sweet, then hopefully it won't seem too odd to call him that. I think the gender ambiguity of that nam...

Truck Lot Bot

by DZiegler on Aug 27, 2019
Sci-Fi & Fantasy

"Come on you sturdy 'ol Bucket 'o Bolts! Suns down. It's time you got moving." Isabella's audio receptors decoded Jack's blunt request and immediately executed several subroutines to bring her systems out of hibernation. Before she could even reach for the charging cable snaking out from the small of her back, Jack reached behind her maintenance chair and r...

The Escort Ch. 07-08

by bunny3374 on Sep 13, 2017
Erotic Couplings

Part 7 Toni chose her outfit carefully after calling the service back. They were sending a messenger over to her with Adam's file and other information. She opened a drawer in her armoire where she kept her wigs, and chose a mid-back length wavy blond wig, since Adam had requested a blond haired woman. She laid the wig on her bed then went to the closet and...