Stockings Heels Stories

98,395 results
Orientation
Length
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Infinite Scroll

Hotel Adventure

by Hosieryboy on Sep 13, 2017
Group Sex

We were introduced to swinging by a couple named Joe and Karen. They were both into garter belt, nylons and heels, which my wife and I both loved. Neither of the girls is bisexual but they use to love to put on a show for Joe and I. When we got to the hotel room, Joe and I set up the video equipment and the girls got some ice for the champagne we had brou...

The Adventures of G Ch. 06

by garterbelt on Sep 15, 2017
Mature

It was late in the day. I sat in my office, door closed. I had trouble concentrating all day. My thoughts went back to happened that morning. I kept seeing Jonathon lying on my bedroom floor, hard cock under the sole of my foot then the look of pleasure on his face when he came in my nylon foot pussy. His running his hands over my body as he helped me dress....

Michael's Exploration Continues

by cuckietex on Sep 16, 2017
Transsexuals & Crossdressers

The contents were now strewn on his bed. Michael decided to take a bath, and while the water was filling, he undressed, his mind filled with a compulsion to express his dark, unfulfilled feminine self. Naked, he walked with purpose to the cabinet that housed his shaving supplies, picked up a razor, some shaving cream and put them on the side of the bath. The...

Fun with Friends in Dorset Pt. 05

by Annatartywife on Mar 16, 2020
Group Sex

The rest of the journey only took about 10 minutes. During this time I remained spread legged with my tits out on display enjoying a gentle feeling up from Henry and Denzel. My stocking encased legs spread over my two hunks. Once we arrived at Ron's house we all piled out the taxi with me being the last to get out. With my tits still out, but having adjust...

Sinful Degrees of Separation Pt. 02

by shoguy on Sep 26, 2017
Mature

Special thanks to editor Hatsuada. In this segment of the Sinful Degrees of Separation in Beverly Hills the stunning seventy-five year old headmistress gets fucked by the enormous cock of the eighteen year old German transfer student. We also learn of her sexual side with females, such as an Asian storeowner and her husband's young teenage intern. *****...

From Heels Fetish to Cock-Sucking

by heelsfan1980 on Sep 16, 2017
Transsexuals & Crossdressers

It is with a sense of disbelief that I take my clothes off. It's like I'm watching someone else do it through my own eyes. I don't want to, not any more, but I'm here and he's left me alone in the room and I don't see what else I can do. I'm taking it a step at a time. Yes, I can put on the clothes I've brought with me in the rucksack. I've come a long...

My New Life in Lingerie

by Everyday2 on Jul 14, 2020
Transgender & Crossdressers

It started innocently enough. There was that time many years ago when I saw a pair of my wife's panties in the laundry hamper. I couldn't help myself and decided to try them on. They were amazing! The way they hugged my ass and balls is impossible to describe. I left them on most of the day as my wife was gone to work. Walking in the panties made me hard, an...

Birthday Breaking

by purekink on Sep 19, 2017
Transsexuals & Crossdressers

I had no idea what my girlfriend had planned for me that day - and if I did, I'd probably still have gone along with it. My birthday wasn't that special an occasion for me. I had no family and having recently moved, I'd no real friends in the city. But Gen was determined to give me a time to remember, and said she'd arranged a small gathering with her frien...

Discovering Amber

by Ms_Allison on Sep 25, 2017
Transsexuals & Crossdressers

Author's Note: This is My amber's foray into telling her recent life story. I have decided that her reward for this is an orgasm, feel free to let Me know if she is worthy of getting one. * I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it h...

Fasten Your Seatbelts

by addictedtonylon on Sep 17, 2017
Loving Wives

Thanks to Lustyleader for her editing of the story, she was a great help. This account is fictional and the persons in the pictures did not participate in the events below. +++++++ "We're going to Antigua" my husband, John, told me a few weeks ago. It was time for vacation and some time away from the kids and his stressful job. My husband is a business exe...