Thigh Highs Stories

119,171 results
Orientation
Length
Source
Infinite Scroll

Just a Little Daydream

by fairyprincess118 on Sep 13, 2017
Romance

I want to walk into a room, softly lit with candles, some romantic music playing in the background. I am wearing a short little black dress, sleeveless, of course. Strappy black heels adorn my legs with the flesh colored thigh-highs held up by a black garter belt. I saunter through the doorway, tilt my head and coyly look up and across the room to the bed, t...

Online Male Crossdresser for Male

by cautiouscc on Jun 26, 2018
Fetish

You all know that CL Personals are no more but a while ago you could meet others and this is one of them. The names and places have been changed and perhaps I am embellishing the event but this did happen to me and is one of my fondest memories. I lived in the high deserts of SoCal at that time. I had been out of work for a long time and had discovered the...

The Polaroid Pt. 01

by LAHomedog on Dec 14, 2020
BDSM

I wanted to try a less theatrical writing style, unlike what I usually post, and attempt a more stylized approach somewhat like the erotica of the 1960s and the 1970s. I set out to write a different story. One of a three-way between an older couple and a young woman, but the characters and the story took me down this road into BDSM - surprisingly to me. Thi...

Yes, Sir

by TheTroubleMaker on Sep 19, 2017
Erotic Couplings

I loved his long, dark hair. I thought about it while I was in the shower, how it would feel to run my fingers through it and pull. Then I thought about how he pushed it back when he really got into his lecture, as if his hair falling into his face would somehow block the point he was trying to make from his students. I thought about the bulge in his pants t...

The Spanking Ad...

by tulsaliza on Sep 12, 2017
Fetish

I read and reread His ad. For some reason, the thought of enduring a bare-assed, over-the-knee spanking turned me on like nothing else. I decided to respond to His ad, I wanted to begin a dialog and see where this would go. I wanted to know more, my pussy was so freaking hot and wet! All I could envision was going to a random office somewhere in one of thos...

Cumdump Boy

by slutgore on Oct 15, 2017
Transsexuals & Crossdressers

Dakota had turned 18 only a few months ago, and just started his first year of college today. He stood at only 5 ft. 6 inches, and could easily be mistaken for a girl at first glance. He had jaw-length bleached blonde hair, with big blue eyes and cute pouty lips. He was fairly slim, his body flaring at the hips with curvy legs and a shapely, squeezable ass....

Erotic Encounter Ch. 01

by GrnEyedRae on Aug 31, 2017
Erotic Couplings

She sat at her desk, engrossed in her work. Already a day from hell, things were hectic in her office; phones ringing, people needing to talk, and she was almost late for a meeting. As she left her office for the meeting, she bumped into a young man standing in front of her door. "Ms. Tremont?" he asked. With a puzzled look on her face, she nodded and he h...

The Party Ch. 2

by kallih2 on Sep 13, 2017
Group Sex

The music was loud as I sat there, feeling naked in my black teddy, matching thigh highs and 4-inch heels. Sammy, a close friend and suite mate, told me about the party and promised that it would be fun. "Besides Kallisti," she argued, "You need to let your hair down and forget about Brad." I knew that she was a bit wild and into orgies, and I think that thi...

The Party Ch. 1

by kallih2 on Sep 12, 2017
Group Sex

The music was loud as I sat there, feeling naked in my black teddy, matching thigh highs and 4-inch heels. Sammy, a close friend and suite mate, told me about the party and promised that it would be fun. "Besides Kallisti," she argued, "You need to let your hair down and forget about Brad." I knew that she was a bit wild and into orgies, and I think that thi...

Long Time Friends First Time Lovers

by wolfinnights on Sep 16, 2017
Transsexuals & Crossdressers

I had always had difficulty connecting with anyone or attracting women. Being 6' 5" tall and 140 lbs when I was 18 during my senior year of high school, my appeal to women wasn't very high. I was never the wrestler or jock material. Being from a small town in South Dakota if you weren't athletic you wouldn't get the ladies. So being the loaner I was I had al...