Pigtails Stories

2,970 results
Orientation
Length
Source
Infinite Scroll

How To Be a Good Mentor

by Voboy on Sep 14, 2017
Mature

For those who've read my other stories, Shannon's back; this is a prequel of sorts. And if you're new to my work, welcome! Hope you enjoy. * * * I was hesitant about whether I should talk to her about this. I mean, the school has a mentorship program for a reason: you're supposed to be able to talk to your mentor about anything, anything at all, and they'r...

The Nightclub

by Bandit1 on Sep 12, 2017
Erotic Couplings

When John went to the topless bar after work that day, all he had on his mind was having a couple of cold beers and looking at the pretty ladies. He stopped his apartment first to shower and change clothes. As he worked putting hot tar on roofs, he doubted that showing up at the club reeking of sweat and hot tar would make him very popular. At 28 years old...

My Pleasures Were Undignified

by optimizer888 on Sep 16, 2017
Transsexuals & Crossdressers

The source material's been done to death, of course. A few have even taken it in the direction this story goes. But none have been terribly faithful to the original, and commercial considerations prevented them from following things to their logical conclusion. My Pleasures Were (To Say The Least) Undignified by Optimizer I've finished preparing the next...

Loosening Up Bk. 05 Ch. 20-24

by SteveWallace on Feb 11, 2019
Group Sex

Chapter 20 - Ceremony Dave, Mike, Roy, and Ken sat together in the media room of the core, waiting to be called to the patio to form up for the weddings they'd each be in. They'd also be standing as each other's groomsmen. Dave said, "I seem to be as nervous for this one as I was when I married Alice." The other men nodded in agreement. Mike said, "I fuck...

Loosening Up Bk. 08 Ch. 01-05

by SteveWallace on Feb 24, 2020
Group Sex

Editor's note: this story contains scenes of incest or incest content. ***** This Book was written with a new reader in mind to the Loosening Up series. As events unfold there are references to place characters and events in the past well enough to follow the story. I thank my dedicated fans for their tolerance to past references. This Book starts with ab...

Nude Secretaries Day: Year One

by Totzman on Jul 2, 2019
Exhibitionist & Voyeur

Shari Kirshner always turned heads when she walked through the halls of the J.T. Levinson offices. Most of her coworkers considered the short, voluptuous redhead to be the most fetching of all the secretaries at the rising marketing firm. When they heard the familiar click of her high heels on the carpeted hallway, more often than not, they would find the ti...

Bought Ch. 02

by Jeremydcp on Jan 21, 2020
Group Sex

Chapter 2. "First" "When I was younger, I liked these to be slightly toasted, but now that I'm older, I like 'em... charred." "You obviously have a thing for flaming balls." Bella's laughter, sweet and melodious as it was to Jason's appreciative ears, filled the late morning air all around them. A rare, precious gem, his bride was brimming with spirit - u...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Senior Year Memories Ch. 31

by aimingtomisbehave33 on May 25, 2020
Erotic Couplings

(Usual Disclaimer Time: Even though this story almost entirely takes place in a high school setting, all the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it's all in good fun. This...

The Rise of AJ Long Ch. 01

by KaceyLoveington on Feb 11, 2019
Interracial Love

Warning: This story contains the use of language, racial slurs and racial stereotyping that many people may find offensive. If you do not like reading stories about hung black men with white women, this this story may not be for you. This story is fiction. The characters are fiction. The views of the author are not aligned with the themes of the story. ***...