Pigtails Stories

2,970 results
Orientation
Length
Source
Infinite Scroll

Cockwhore's Total Gangbang

by Freeyourmind on Sep 19, 2017
Transsexuals & Crossdressers

As I waved goodbye to my wife as she pulled out of our driveway for a weekend business trip a smile began to grow on my face. Anticipating another entire weekend all alone, and thinking of my plans to indulge my deepest fantasies, caused goosebumps to run up and down my arms. Heading back into the house I grabbed a cool glass of water to quench my thirst and...

Dwelling in Desire Ch. 07

by joodle on Apr 11, 2018
BDSM

There's nothing quite like the feeling of a safety being disengaged at the back of your head. I felt it before I heard it. The heaviness. The coldness. It's twice the rush when someone else's finger is on the trigger. "So fucker, what the hell did you say to Kate? There's little opportunity for bullshit right now." "Put the gun down Joe," I warned. More p...

How I Became A Whore for Black Cock

by timewarp69 on Sep 13, 2017
Transsexuals & Crossdressers

(Some prior notes about me and this story: If MALE bisexuality, crossdressing or interracial sex bother you, don't bother reading further. I am someone who considers himself a fairly "masculine" or normal guy, in many aspects. I think, however, that many straight, gay, or bi guys have always had secret fantasies,whether or not they'd actually admit to it, ab...

A New Direction Ch. 03

by MyUncensoredSelf on Sep 15, 2017
Transsexuals & Crossdressers

Our new beginning was going swimmingly; we still had traditional sex most of the time, although it was wilder and more passionate now, but we'd set aside every second weekend for me to dress and her to be more dominant. It was fantastic and we both felt more engaged with life in general we found. Well, it was that time and I got home from work on the Friday...

A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...

The Visit Ch. 2

by The don on Sep 13, 2017
Loving Wives

The week before Mark showed up for his visit was one long fuck feast. It seemed that my wife Bren just couldn't get enough sex. I would come home from work and she would be dressed in a different outfit every night. She had pull out all of her old mini skirts and mini dresses. Since she had put on a little weigh in her great ass it caused the skirts to becom...

Four Words Ch. 02

by tom6432 on Sep 11, 2017
Fetish

Elizabeth, my 41 year old wife, sat at her desk in her punishment PJ's. The PJ's consisted of a one piece Dr. Denton footed sleeper complete with a drop seat. The zipper ran down the front all the way to her drop seat flap for easy access. It fit her snugly accenting her fantastic figure. It was a white outfit trimmed with pink and Disney characters on the f...

Stephanie's Secret

by Instinct84 on Sep 14, 2017
Erotic Couplings

Stephanie Nickleson looked at herself in the mirror, her long strawberry blonde hair was done in braided pigtails, her makeup was perfect and made her skin look beautiful, her blue eyes sparkled and she loved the way her boobs looked in this outfit. Her 24B tits looked spectacular in the push up bra and this tight top they had given her and her ass looked am...

The Costume Party

by Electra042 on Sep 17, 2017
Loving Wives

Tying the second pink ribbon into a big bow on my pigtail, I have to smile at my reflection. Not one for parties, I couldn’t resist this Halloween one after you suggested our costumes. My sweetheart pink dress is cut very short, as is the starched white apron that criss-crosses in the back, barely covering the frothy lace of my crinoline. When I move, the dr...

Tiana's Toy

by vootvoot on Sep 14, 2017
Sci-Fi & Fantasy

This is my first ever piece of erotic fiction! Any feedback you have would be greatly appreciated, and it may decide whether or not I continue to write. Cheers, and enjoy! ***** The tall, lightly tanned girl walked through the door, and took in the circular room with her right eye. Several benches lined the walls, strewn with an assortment of half finished...