High Heels, Bra Stories

250,180 results
Orientation
Length
Source
Infinite Scroll

The Cottage Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Mike Harris was seventeen years old when the worst blizzard ever to hit Chelmsford forest struck in December 1986. That is when this story really begins. But first we need to learn a little about Mike Harris before that fateful winter's day. Mike's father had left the family home when he was still a baby. He lived at home with his mother Doris and his older...

Being Taught To Wear a Garter Belt

by pantycladlad on Sep 13, 2017
Transsexuals & Crossdressers

BEING TAUGHT TO WEAR A GARTER BELT & HIGH HEELS After that special Sunday afternoon, where i tried dressing fully in girl's clothing, i had managed to amass a fairly good sized wardrobe of feminine things to wear. Within months my hidden cache' included several pairs of silky sheer panties of different styles, a Jantzen "Postage Stamp" pantygirdle, anothe...

D Looking For S Ch. 01

by Bloke1 on Sep 15, 2017
BDSM

The posting read, "Dominant looking for submissive". You have seen it before, many times. You have seen it once or twice a year, for many years now. It is up for just a day or two and then is gone. The posting reads "Dominant white gentleman looking for submissive single white woman to serve. Age between 40 to 55. Experience not necessary. Willing to train...

Caught by the Past Ch. 01

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1 - Dress to impress Your latest girlfriend, Karen is very kinky and she introduces you to all manner of strange people. You on the other hand are rather naive and innocent. You found one handsome guy, James strangely attractive. He has long muscular legs, a washboard stomach, dark skin, blond hair and an impeccable speaking voice. Having met many o...

Under the Gaze of the Sirens 01: My Girlfriend Thinks You're Gay

by jakladd on Dec 2, 2019
Transgender & Crossdressers

"My girlfriend thinks you're gay." "What?!! What did you just say?" Bobby said incredulously to his friend Carl. "You heard me,"...."Sarah thinks you are gay," Carl smirked. "Well she's wrong," Bobby replied. "We'll see," Carl continued. Bobby sat there and stewed inside as the two boys sat on the couch watching the game. "When she comes home we'll ask...

College Bound: Summer to Remember Ch. 04

by shoguy on Sep 13, 2017
Mature

Chapter 4: Allison's Rock Star Uncle. The BIGGEST of the BIGGEST! My Uncle Jimmy is a member of a very famous rock band from the late 70's. Although he is 62 now, he is still extremely sexy, and I do mean very HOT! He stands 5'11" tall and has a slim, tight body, weighing just 150 pounds. He still has his rock style long hair and has tattoos all over his a...

MILF Lives Her Fantasy

by MilfMaid on Sep 14, 2017
Exhibitionist & Voyeur

As a teenage exhibitionist I had a diary where I could write all the dirty little things I did that I could not even tell my best friend. That was never very satisfying because I wasn't really sharing anything with anybody. But it was all I had. Since my teen years, however, I haven't needed a diary because I haven't had any dirty secrets to worry about. In...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Cheating and Rivals Pt. 06

by xleglover on Sep 13, 2017
Loving Wives

Continuing Book 1: Cheating. This Part 6 continues the flashback from Part 5. ***** "What's with you?" Allie asked the following Saturday. "What?" Jen said. "You've got a bounce in your step today," Allie pointed out. She added with a teasing grin, "Getting over Mike?" "I'm not getting over Mike," Jen said frowning at Allie. "I don't know. Maybe I'm adj...

The Girls from Work Ch. 02

by lulu_dools on May 1, 2018
Transsexuals & Crossdressers

I woke up to two giggling girls. They were lying on the bed with me in the middle and they were smoking a joint. Annie lying there like a goddess in her black negligee and Denise in her red outfit. I was already hard and this is what they were giggling about. As soon as they realised I was awake Annie was first to speak as she said "Lulu, your panties look...