Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

The Retirement Party

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

April 3 Jo had been singing it for days and it was driving me mad! "It's all about the bass, about the bass..." On and on she went until finally I screamed: "Enough already!" "Oh hubby. Do you not like my song?" "Well, I like the way you move to the song." Jo looked hot swinging her big sexy curvaceous ass in a short micro skirt and flicking it up occasi...

Mando & Lek

by Purple_Raihne on Sep 16, 2017
Romance

(I was writing this story when I was involved with two people. The three of us were the character basis. But they ended up committing to each other and forgetting I even exist, so I have no desire to bother trying to finish this story in the slightest. No names need to be changed as I already changed their names and Marie is my own middle name. To whomever d...

The Dresser Files Ch. 1

by rapidran on Sep 12, 2017
Fetish

"Can I get you anything?" she said with a slight smile. "Sure, let me have a bourbon and ginger ale." I replied. She turned and walked back up the aisle. I leaned over and looked at her as she walked away. I just love flight attendants. She had a tight ass and a cute sway as she walked. I envisioned her sweet ass covered in a tight pair of silk panties. I ha...

Where did My Damn Key Go Pt. 02

by PascalSage on Sep 24, 2019
BDSM

It didn't take me long to find something to wear. The lucky choice of attire was a sexy school girl's outfit I used to wear in a lot of my "private" encounters. It was complete with a blouse and plaid mini skirt. To make sure I was up to bitch's standards, I threw on some makeup here and there to give me a bit of an edge. A little bit of lipstick here, some...

Just Look at Me Now Ch. 02

by GFfan on Mar 2, 2020
Transgender & Crossdressers

When I arrived at my first scheduled play date with the kinky lesbians Jude and Becky, I was extremely well prepared logistically. I had triple-checked the items I'd been instructed to bring and completed all my assigned tasks, including shaving my legs. Emotionally and psychologically, however, I was shakier. I had loved the impromptu feminization we had in...

Julia, Ben and Lisa Ch. 15

by chloejacobs83 on Mar 23, 2020
Transgender & Crossdressers

Ch 15: Tuesday A few quick notes: 1. this is the fifteenth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned * I slept till 9:15 and still groggy, pleasantly sore, went into...

Maid to Order Ch. 06

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele and Bill talked late in the night stopping whenever their lust for each other overtook their need to converse. Arrangements were made, compromises reached and finally a mutually beneficial arrangement was entered into. "Ok Bill let's call it a night and tomorrow we give our plan a try," Michele said yawning as she stood. Her maid's uniform was quit...

Jolene's Momma Pt. 02

by ValoryG on Oct 6, 2020
Transgender & Crossdressers

After Brandi left, after I had willingly signed my privileged life away, I also had some nagging fears. Like, would Jolene be able to carry out her role, since she was usually so sweet and caring, and she usually gave in to what I wanted? Or would she take after her mom and become a merciless taskmaster and sadist whom I would hardly recognize? After we ha...

Crossed

by komrad1156 on Sep 19, 2017
Mature

"Do we really need to run 20 miles today? Why can't we do 18 again?" "Look, Phil. If you're serious about running your first marathon, then we stick to the schedule. Today is 20, not 18. You've got to get these longer runs in because the difference between 18 and 26 is huge. Trust me." "How many have you run? Five, right?" "This'll be number six. So it's...

A Boiled Frog Pt. 02

by noobdude on Sep 18, 2017
Transsexuals & Crossdressers

Part Two -- Simmering in Las Vegas Author's Note: I was literally blown away by the positive comments I got from my first part. This is my first story attempt and I am enjoying the process. Any constructive criticism would be appreciated. I can only get better if I know what I did wrong. Chapter 1 Tuesday I woke up with all 12 coins in my possession. This...