Nylon Stockings Crossdressing Stories

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Orientation
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Infinite Scroll

Family secret Ch. 02

by becky_buns on Jun 9, 2020
Transgender & Crossdressers

Peter and I had both been invited to his sister's wedding. It was quite a big do at a country hotel. It was held over the whole weekend and we had our own rooms with en-suite bathrooms... And big mirrors on the wardrobes... Of course after our last little encounter I saw this as a great opportunity to bring some sexy outfits, and take things to the next lev...

Barely Legal Ch. 05

by AntonioSanova on Jun 9, 2020
First Time

Now it was my turn to get her off manually. I sat in the chair next to the couch as I had been doing. I patted my hand so she sat in front of me, facing the laptop and Jakob as he eagerly awaited seeing me get his wife off. I wrapped my arms around her, playing with her boob and long nipple in one hand and her clit with the other. I was slow and gentle. She...

This is What I was Meant to Be

by boistockings on Jul 6, 2020
Transgender & Crossdressers

I had been struggling for a while to keep my urges at bay. Mostly by dressing up in my skirt and stockings while I was alone at home. I would parade around in it until my wife got home and just before she did I would jerk myself off, clean up, and put away my outfit. It had been quite some time since I had been with another male, but the urges were growing s...

A View from the Other Side

by RalphKing on Mar 18, 2020
Exhibitionist & Voyeur

I can taste his expectation, as I kiss him on the lips. As we part, he tries to reach inside my dressing gown. "No, peeking," I say, as I slap his hands away. "Not yet." He turns and reaches inside the wardrobe and moves some hanging clothes to one side, before squeezing himself though the door. Soon, he's settled on a chair. He places a glass of water on...

Fantasy to Reality

by fantasyCD65 on Apr 20, 2020
Transgender & Crossdressers

So there I was, my stockinged legs resting on his shoulders as he pumped me relentlessly with his thick hard cock. My panties were long gone, allowing my boy clit to slap rhythmically against my stomach. The suspender straps were still just about attached to my garter belt and my bra clung to my D size breast forms. And I was in complete heaven. — I suppos...

Naughty MILF Caroline Pt. 03

by scooter111 on Dec 9, 2019
Humor & Satire

Today, Caroline choses a white satin Basque underneath a prim butter-wouldn't-melt white blouse and goes to work with Peter, her husband. He is a boring, dozy fucker. Sex is almost non-existent with them and they don't talk all that much, it's a marriage of convenience. She's a fuckin' nightmare to live with also, stuck up, nasty, petty, authoritarian, but t...

Dress Up For The Girls Next Door Ch. 02

by JackorJill on Jul 15, 2020
Transgender & Crossdressers

“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it was this hot. “I have a few cold beers in the fridge,” she cooed. “Why don’t you take a b...

My Life in High Heels Ch. 09

by cdandie on Sep 14, 2017
Transsexuals & Crossdressers

For those of you reading my stories they are not in chronological order. Not any order for that matter. Just writing as I reminisce of my past. Also I appreciate all the wonderful responses. Thank you. If you enjoy reading them I appreciate the atta girl. This is how I got my serious start with groups of men. I had cross-dressed for many years. A wonder...

Gillian Newark's School Tales Ch. 07

by SylviaG on Sep 19, 2017
Mature

The phone rang downstairs in the hall. I heard the answer phone kick in, and then I heard Pete's agitated voice. "I can't make it at the moment, I, I'm stuck. I'll be as quick as I can, don't worry." I began to struggle but it was no use. Even if I had the key I wouldn't have been able to use it. The phone went again around 20 minutes later. "Don't panic...

Two Bi-Curious Couples Meet Ch. 05

by married40scouple on Sep 14, 2017
Group Sex

Hi All, Thank you all for reading our stories, voting, and your excellent comments and emails. The following is a stand-alone story so there is no need to read our other submissions to understand what is happening. Please note this story contains cross-dressing, same-sex, and anal sex scenes. If this is not your cup of tea, there is no need for you to read f...