Nylon Stockings Crossdressing Stories

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I Love My Breasts!

by grgy56 on Dec 17, 2018
Transgender & Crossdressers

I Love My Breasts! Yes, that's what I said. "I love my breasts! Boobs! Knocker! Honkers! Fun Bags! Tatas! Tits!" It all started many, many years ago. I loved stealing glances of my father's Penthouse and Playboy collection. I could barely wait for my parents to leave so I could sneak a copy back to my room, lay naked on my bed and beat one out. I had to ta...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

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...

Michele And The Predator Ch. 03

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

The Predator was stunned; it dawned upon him what had happened; he had fucked and been fellated by a transvestite. A man dressed as a woman! He looked at the pathetic sight lying before him on the bed and laughed. He thought to himself that she was just as good as any 'real' woman he had fucked; and she sure wasn't going to be telling anybody about this even...

Maid to Order Ch. 01

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele Ascending My wife had left me a year ago. I'm surprised she waited as long as she did really. We were married when we were both eighteen when I was in the army. She had been my only girlfriend and I was scared she wouldn't wait for me because I was being deployed overseas. It was a whirlwind romance. I'd heard rumours that she'd been a bit loose be...

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 Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Busted

by nikkiesilk on Sep 13, 2017
Transsexuals & Crossdressers

"Happy is what happens when all your dreams come true," Stephen Schwartz. Sandy came into the bedroom where I was still dozing, holding a pair of tights in her hand. 'Babe, I wouldn't ask, but I'm so pushed for time and I've just laddered my last pair of clean tights. I desperately need some before I go to this client meeting.' She held them up as if to p...

She Snuck Me a Pair of Her Panties

by anonymouspeggy on Mar 2, 2020
Transgender & Crossdressers

I woke up on Christmas Eve to the sound of someone knocking on the door. It was after nine o'clock. I was in a guest room in my uncle's basement sleeping in a tee shirt and pair of silky black panties with a red floral print. Next to me was another pair of panties that were stiff with my dried cum. Angela had used them the night before to give me a handjob...

My Brother, My Sister Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

I wrote this story originally under the title "Be Careful In the Park" about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find t...