Pantyhose Crossdress Stories

6,922 results
Orientation
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Infinite Scroll

The Surrogate Ch. 02

by MicheleNylons on Jan 20, 2020
Transgender & Crossdressers

Chapter Two - Becoming Mila Mila slept in a satin nighty and panties that night but she was untucked of course. There was no sign of Peter Randal and she had the apartment to herself. She had practiced her makeup for a while and walking in heels and then after a light dinner she retired. She had tried on her sister's clothes and divided them into two piles...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Sissy life

by Kaori_chan on Jan 21, 2021
Fetish

So Ive always had this fetish. I love wearing panties. My name is Jake and Im a twin with my sister Jane. Ever since I was young I would sneak into the laundry room and wear my sisters panties. Being twins, we were always around the same size. She always had the cutest underwear. It was pink, frilly, and sometimes had cute designs all over them. My fetish de...

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Sissy Perfection

by cornthuxton on Dec 23, 2019
Transgender & Crossdressers

Hello. I had done just about everything there was to do mature, lesbians, trannies. And several times each variety. So I thought it was time for a twink. As with my previous adventures Hong Kong was my hunting ground. Two, week long trips a year made it easy for me to indulge me desires. I guess I am pan sexual...whatever that means. I'm open to lots of...

Caught My Husband...in Lingerie

by TheGenderBender on Sep 16, 2017
Transsexuals & Crossdressers

I had been away on a spa weekend with my girly friends so was going to surprise my husband by arriving home 4 hours early. He had been so happy for me to spend two nights in a luxury spa hotel I had to repay him the favour, and I knew just how to do it. I crept slowly into the house, and by the sounds of it he was upstairs in our bedroom, probably doing som...

Wet Dreams

by TheNextGamer on Jul 15, 2018
Fetish

For two entire weeks, you, John Doe, have researched tirelessly on a place that historians and philosophers have secretly called... The Labyrinth. A special location that links the psyche of every living being on Earth. The place where you can traverse in people's dreams and do whatever you've wished. Out of sheer luck, you've managed to find a way to enter...

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Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Sissy Academy

by Cynthia Sissy on Jan 2, 2019
Transsexual

(feel free to message me about anything! I'd love to hear from my readers :)) The alarm beeps away as you groan at the sound of it. A cool breeze rustles the curtains, letting the sun peek through. Pushing your hair to one side, you check the time. "Oh, it's still early," you say, pushing the sheets away to reveal your blue satin panties and chemis...

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Relax

by BoredTBDL2 on Jan 7, 2021
Fetish

“Jesus man, that’s a lot.” Mike stared at the old metal table between you two in the middle of his backyard patio for what felt like several minutes. You couldn’t blame him for taking his time though; you two were just gonna meet up for drinks, but the alcohol had other plans, and now you feel like you need to pay your friend for being your therapist. “I don...

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Confiding in My Hairdresser

by Leighharding on Dec 19, 2018
Transgender & Crossdressers

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The cha...