Nylon Stockings Crossdressing Stories

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Giving My First Blowjob

by SLMaid on Sep 16, 2017
Transsexuals & Crossdressers

After a few beers and chicken wings, I left Jim at Gunny's. As I got up to leave I handed him an envelope and told him to give me a half hour then come over to my hotel room. As I left I wondered if he would go through with this. In the envelope was a pair of black nylon full brief panties with a note that said "Put these on before you come over", Sara. Aft...

The Door to Door Stocking Salesman

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

In 1959 Brian Macklin was in his mid forties and was making just enough money to get along; his dreams of affluence were ruined when his marriage failed. He used to be a sales executive for an affluent London based firm but all of that came to an end when his wife left him; his father-in-law owned the firm where he worked; say no more. To make matters worse...

Stockings & Stalkings Pt. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Giselle applied the clear topcoat to her ruby-red lipstick; she pursed her lips as she looked at her reflection in the mirror. "There; finally finished," she smiled to herself. It had taken Giselle nearly one hour to transform from 'Gary', her male alter-ego, into Giselle, the hot transvestite staring back at her from the mirror. She smiled to herself as s...

A Night of Surprises

by StephaniePlayland on Oct 16, 2018
Transgender & Crossdressers

Back story. I've been crossdressing for many years. The reasons for it are not really important however, I know I enjoy escaping being me, and getting to be softer, submissive and docile. My friend, Sir caught me crossdressing a long time ago, he has never really cared what I do as he has lots of women. We both enjoy the friendship and no judgements about a...

Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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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...

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

Planet of Men Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

At 1600 Eastern Standard Time (EST) on September 27 in the year 2020 AD the UN announced that General Atomics Corporation (GAC) had saved the world. After years of panic in every country that the world was doomed due to the effects of global warming, GAC announced that, with funding provided by the UN, they had developed self-sustaining micro atomic reactor...

The Elephant in the Room Ch. 01

by MicheleNylons on Apr 3, 2018
Transsexuals & Crossdressers

Author's disclaimer: I am not a fan of 'Sissy' stories. Some crossdressed bloke dressed in taffeta and crinolines, frilly knickers, with blonde ringleted girly-girl hair being dragged along on a leash by some leather-clad dominatrix Mistress who forces him to be her sissy, spanking him and finally sticking a big plastic cock up his arse is not my forte. Tha...

My Need: Crossdressing

by TheBigVoyeur on Jul 27, 2020
Transgender & Crossdressers

Dear Wife: There was a list of things, my peculiar fetishes, that you said you were struggling to understand and accept. I hope that this note, my second of its kind, helps you get your head around another of my quirks. All I ask is that you hear me out, at least try to read all of this before galvanizing your opinion of me. And believe that I am opening u...