Heels Stories

80,885 results
Orientation
Length
Source
Infinite Scroll

The Writer's Secret Ch. 03-04

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Thanks for all the wonderful comments on the first two chapters! Here are the next two chapters. It's time to teach Loren a bit about being Laura before their dinner party. Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of f...

Dianne in Panties

by eliasroticatwo on Sep 12, 2017
Fetish

If you're lucky, every once in awhile you fall for someone. Sometimes its love, sometimes its lust but its usually some sort of mixture. I was more than lucky when I first met a woman named Dianne B. Dianne was working at the company I'd just joined. She was assigned to mentor me and we got along well. I was pleased to have made a new friend, one I continue...

My Own Heaven Ch. 03

by DaniSub215 on Sep 13, 2017
Exhibitionist & Voyeur

This story is fiction based loosely on people, places and events mostly from my life. I strongly suggest that you read the previous chapters before you read this one. I love feedback, comments, criticism and ideas for future chapters; it will help me improve my writing, enhance the story line, and encourage me to continue writing. Also, take a moment and vo...

A Fateful Trip Pt. 01

by TTM86 on Mar 13, 2018
Transsexuals & Crossdressers

I had planned for weeks for this moment. I entered the sex shop and walked in confidently, my heart racing a million miles an hour. The only person in the store was the cashier, a tall blond woman. She was over 6 feet tall, dressed nicely in a tight white top, tight peach pants and some ankle boots with a medium heel that were in a matching peach color. She...

Caught in High Heels

by BigAndy922 on Sep 11, 2017
Transsexuals & Crossdressers

I couldn't believe the feeling as I slipped the pantyhose on over my legs. This was an absolute dream come true and I was living it right now. My friend Julie had gone out for the night with her 15yo daughter and she'd given me the spare keys to her house. She'd had a tradesman doing some work and needed to leave before he'd finished, so she'd asked me to...

The Fetish Shoe Shop: Laura

by fantasyboy on Sep 19, 2017
Fetish

Laura's boyfriend telephoned to make an appointment for them to visit The Fetish Shoe Shop. Laura was 18 years old, slim with long black hair. She had recently agreed to go the prom with her boyfriend and had persuaded Daddy to buy her an expensive black silk mini dress for the occasion. However, what she couldn't ask Daddy to buy her was some real nylons, a...

The Party

by smilecat on Sep 14, 2017
BDSM

Ding! The sound of the doorbell downstairs brought Kitty to attention, snapping her out of her nervous trance. Tonight they were hosting a dinner party to celebrate a breakthrough at Daddy's lab. Her first impulse was to head to the door and welcome their new guests to their home, but that was Daddy's job tonight. Her job was simply to get dressed nice, an...

Taking the Lad out of Alladin Ch. 05

by CaseyHeart on Sep 24, 2019
Transgender & Crossdressers

I was having the best dream. There was this hot, kinky, big tittied stripper laying underneath me, and I was fucking her brains out. I could feel her boobs pushing against my chest as I slid my cock back and forth inside her hot pussy with long, slow strokes. Her pubes were bristly and super rough, and for some weird reason her face looked just like mine, bu...

Sara Jane Submits Ch. 02

by Subone1 on Dec 2, 2019
Fetish

I woke up to use the restroom, it was 5:30 AM and still dark outside. As I swung my legs out of bed I almost stepped on Sara Jane! She was asleep on the floor next to my bed, curled up like a little puppy. She had her hair up in a towel on top of her head from the shower, not a stitch of clothing on her wonderful young body. "Jesus Sara, what are you doing?...

The Footjob

by Apollo3000 on Sep 11, 2017
Fetish

For some time I'd wanted my beautiful girlfriend Carolyn to give me a really unforgettable footjob. As a committed foot-fetishist, it was one of my biggest fantasies. And Carolyn knew it. So when I received an SMS message one dull afternoon in the office saying, "Tonight's the night you get my beautiful feet on your hard cock :) C xxx", I almost came there a...