Thigh High Boots Stories

231,842 results
Orientation
Length
Source
Infinite Scroll

Unexpected Pleasures

by kisinurkitty on Sep 14, 2017
Group Sex

It started out as my boyfriend's idea of course, but I must admit it sounded pretty good to me. Jason said he always wanted to see me sucking his cock and fucking me at the same time, but since he could not be in two places at once, he needed help. That is where his friend Jim came in. Now I liked Jim ok, he was pretty good looking, and nice besides, but I d...

You Never Know

by Shady_Lady on Sep 16, 2017
Letters & Transcripts

Note from the Authoress: For any one who has read the Julie Journals they will know I always mention that my stories are a mixture of fact and fantasy. The content of this story is pure fantasy but the characters are fact. For that reason I have not included this as part of the Julie Journals. It is dedicated to a woman who I know and love very dearly. * *...

Santa Takes Back What is His

by RedHairedandFriendly on Sep 16, 2017
Sci-Fi & Fantasy

Eyes that normally twinkled with merriment stared at the woman who had just told her brother that Santa wasn't real. A smile, usually showing warmth, laughter, cheerfulness, now held a frown; rosy cheeks, burned a brighter red from anger. Kris Kringle watched young Tommy walk away from his older sister, his heart broken and his dreams shattered. He would mak...

Death Gestured Toward a Grave Ch. 01

by mvicious on Sep 13, 2017
NonHuman

He watched her from the shadows as she hurried across the street. Her six inch heels forced her tight little ass to tilt upward, causing the bottom of her buttocks to peek crudely from beneath her short plaid skirt. A well dressed, handsome man in his 40s held the door for her and she ducked inside and shook off the cold. She slowly peeled off her jacket as...

The Plan

by SexyNoises on Sep 17, 2017
Group Sex

Joe sat in the corner of the club and watched the woman at the bar as he'd done for many nights now. She'd been in every night for over a week and had become a form of entertainment for him. It was his club and he made it his business to know his guests, especially ones as gorgeous as her. She had made no attempts to hide her assets in the past and tonight...

Like Father, Like Son

by caramelgirl_2 on Sep 12, 2017
Interracial Love

Nick was home from his junior semester of college for winter break— out of the balmy, short-sleeves- and-sweater weather into the goose-down, wool coat bluster of the northeast. He was reminded of what he was in for when his flight was almost canceled. His mother wouldn't be the one picking him up from the airport, not if it was as bad as everyone indicated....

Role Reversal for My 50th Pt. 02

by Lifeinlingerie on Aug 20, 2019
Fetish

This is a continuation of the story of my 50th birthday in New York with my wife of over 25 years. We've been exploring my submissive side. I hope there is more to come after this... We were walking through Times Square mid-morning, dressed casually and gawking at the sights like the tourists we were, when Gwyn noticed the sign and mentioned it to me. It si...

Valerie in New York Ch. 02

by gunhilltrain on Jan 8, 2019
Celebrities & Fan Fiction

[Chapter One is in my profile. The scene on the roof is an expansion of a much shorter one in the movie.] *** Rooftop Sojourn In late May of 1967 Valerie wanted to change rooms but she had a couple of weeks until a new rental became available. She stowed most of her possessions with her friend Stevie but she figured she could get through the gap by sleepi...

Silence is Golden Pt. 02

by Itsalljustforfun on Apr 23, 2019
Erotic Couplings

The next day was another typical English April day, damp and still cold so there weren't many people about. I head towards the cafe and, walking around the corner of the building, I see her sitting on a bench about 50 metres ahead. The instant she spotted me she stood and walked away, following the path bordering the lake. I followed. And as I followed I t...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...