Nylon Stockings Crossdressing Stories

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Infinite Scroll

Mommy Goes Shopping with Me

by JhMcKn on Aug 18, 2017
Fetish

This takes place in late 1949 after WWII had ended. Sheer nylon stockings were worn by women everyday and some held them up with a girdle, some a garter belt, and some with 'roll garters'. No one in the story is under the age of eighteen. It was earlier in the afternoon than I usually got home. I saw Frank's car in the back of the house so I knew he was...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Just Do What The Nice Man Says Honey

by Michele Nylons on Apr 22, 2025

Julie Cashmore followed her gentleman caller downstairs and escorted him to the front door. She opened the door and looked both ways up and down Clifton Road and seeing that the street was deserted she nodded to her gentleman caller who bustled past her most ungraciously and quickly strode away. He did not want to be seen leaving 32 Clifton Road; none of her...

You Never Know

by lipsticked on Sep 13, 2017
Fetish You Never Know

I moved to Los Angeles from New York about eight years ago, right after my divorce. The marriage didn't last long and ended bitterly. I now live a block from the beach in Santa Monica in a fairly exclusive high-rise apartment building. I quit my job as a graphic artist with a top advertising firm in NY, when I moved and started my own business here. I have a...

Murder Misstery

by thrillerauthor on Sep 16, 2017
Novels and Novellas

(c) 2009 by Thrillerauthor When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the youngest traders at the Chicago exchan...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

A CROSSDRESSING APPRENTICESHIP

by rivi on Apr 22, 2025

I went to a boarding school . Contrary to public perception it was not a hotbed of buggery . Actually the only instance of it I knew of was hearing a slightly distressed call from another boy ( we slept in dormitories with eight beds ) when another more physically mature boy had climbed into his bed . I was falling asleep as this happened and did not track t...

Stacy and Matt

by mattpantyhose on Jan 28, 2020
Fetish

Matt's bliss ended almost as soon as it had begun. The girl he had met and who not only was pretty and smart, but also enjoyed his crossdressing decided that career was her priority after merely few weeks of their relationship; the two broke up as she moved to a different distant city. Matt still had a good job, amazing boss and sympathetic co-workers, but d...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...