Wig Stories

6,038 results
Orientation
Length
Source
Infinite Scroll

Alley Fuck

by little sebastian on Sep 12, 2017
Transsexuals & Crossdressers

I lay on the ground on my side in the alley listening to the grunts and moans. My skirt was too low and was restricting movement so I lifted it up a bit, then reached back down to my panties and continued rubbing my cock through the lace. My head bobbed up and down, my wig bounced its bangles against my forehead as my lips clenched the cock in front of me. T...

Saturday Night Fun

by kayla69 on Sep 26, 2017
Transsexuals & Crossdressers

This is a true story. Feedback is definitely welcomed! ***** I made sure that all my body hair was removed. I feel so sexy when my skin is smooth. I had attached my new breast forms earlier, and feeling their weight pulling on my chest is always enticing. I put on a cute white bra and white cotton panties, then pulled on my favorite "Naughty Kitty" t-shir...

Sissy Housewife Learns to Eat Cum

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

Only a few days after Miss Jennifer agreed to let me be her housewife, she informed me that now that I was "pretending to be a girl" and was required to always be dressed completely as a girl, she expected me to service her the way one girl would service another, with my mouth and tongue. At least three times every day (always in the morning before she left...

Becoming Cassie Ch. 03

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

For the next two weeks all I could think about was being Cassie again. All my life I've always had dreams of being dressed but the people in those fantasies were never real. My fantasies were now becoming realities. And I had to wonder what were the Warrens thinking this week. I had really been expecting the absolute worst scenario if I got caught in real...

A Wife in Venice California Pt. 2

by AnnabelleandJay on Sep 13, 2017
Loving Wives

WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are under age, PLEASE EXIT. IF YOU ARE UNDER THE AGE OF 18, or otherwise forbidden by law to read electronically transmitted erotic material, please EXIT.NOW!!!! All characters in this story are the creation of the author, and any resem...

Michele And The Predator Ch. 03

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

The Predator was stunned; it dawned upon him what had happened; he had fucked and been fellated by a transvestite. A man dressed as a woman! He looked at the pathetic sight lying before him on the bed and laughed. He thought to himself that she was just as good as any 'real' woman he had fucked; and she sure wasn't going to be telling anybody about this even...

The Theater Pt. 01

by Stephisissycd on Sep 15, 2017
Group Sex

About a mile from my apartment is a porno theater. It plays hardcore porn films and is as seedy as it gets. Most of the people there are black and Latin men. I'm a petite white guy who has recently started to crossdress. Something about wearing slutty girls clothes makes me really horny. I'd drive past that theater and imagine walking in dressed like a tot...

The Teacher and the Bus

by bigrimmstales on Aug 19, 2017
Exhibitionist & Voyeur

The inspiration for this story comes from 'Stangers on the Bus' by SubmissiveVirginSlut. I thought about her story and wondered what would happen if the person the young girl thought she was using for her own gratification saw it a different way... She'd tasted so good when I licked my fingers as I left the bus. That slut had been coming to my lessons for w...

Change of Fate

by Neorotoxin on Sep 16, 2017
Transsexuals & Crossdressers

Foolish choices fill most every persons life at least part of the time. Most of these choices are harmless enough, and don't leave much of an effect on our lives. Other times, like this, we make a choice that forever changes our lives... I used to be a normal guy, like many others, at least for the most part. I dated normal women, and did normal things. The...

Peg'n' Elvis

by convict2shave on Mar 30, 2020
Fetish

Peg'n' Elvis "You're back for another drink already, Mr. Presley?" The bartender, wiping the counter in front of him, winked at Harry McComber. "You realize this is the third time I've served you in the last fifteen minutes? At this rate, I'm going to have to cut you off soon." Harry glanced around the room. "Really, two other guys came as Elvis?" He turne...