Crossdressing Aunt Stories

13,440 results
Orientation
Length
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Infinite Scroll

Sissy Constructs for the Manly Man

by _Rinaldo on Nov 16, 2019
Fetish

Alpha males all have an image to uphold. They spend decades, perhaps even their entire lives honing their bodies and personalities to achieve a higher standing in society: to be viewed as the perfect example of what the ideal male should be. Handsome, strong, muscular, confident, etc. The perfect breeding candidate, in essence: desired by all women, and envi...

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Costume Store

by Zekar on Nov 23, 2016
Fantasy

The Costume Store is an indiscreet shop in the mall. Few people paid it any mind and many walked passed it without giving it a second glance. If they knew what wonders were inside they might have given more thought to going inside. Inside the shop walls were racks and racks of costumes. But not just any costumes. There were costumes that turned the wearer in...

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Big Booty Goth BF

by Furry-god69 on Dec 7, 2020
Transsexual

You are Damien Smith a 18 year old high school senior who's really into goth culture, your parents say it's just a phase, but you don't think so. you look like a regular teen save for you're dark hair, and very feminine figure. For as long as you could remember you always a very girly frame, which many people made fun of, except for, Avery, the love of your...

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Sweet Treat

by SaucyMasquerade on Sep 14, 2017
Transsexuals & Crossdressers

I As the water streamed across the window pane, I watched Jayne pull her coat tight, dashing from the car, through the torrential rain into the house, cursing the British summer in all its soaking glory. "Steve," she called, as she hung up the coat to dry, "I've an invite here, to a fancy dress party, Helen is holding on Friday" "I'm in here," I called...

All I Want for Christmas, Is You! Ch. 01

by grgy56 on Dec 17, 2017
Transsexuals & Crossdressers

"Open mine first!" Cheryl gleefully shouted as she handed me a beautifully wrapped Christmas present. It was a cold, crisp, white Christmas morning. But much later in the morning than I would usually get up for Christmas. For some reason, I slept in regardless of my excitement to open the presents under the tree. As a kid, we would open our gifts on Chris...

A Taste Of Lace

by AdamZasse on Sep 13, 2017
Transsexuals & Crossdressers

By Adam and Evie Zasse The authors would like to extend our thanks to volunteer editor 'Larry in Seattle' for his help in proof reading this story and for his insights and suggestions I've never been into crossdressing. Oh sure I swiped a few pairs of panties from my mom over the years. But they were only something to wrap around my dick when I jerked o...

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 Awakening Ch. 04

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Part Four – Michele Returns The woman is slim. She is wearing a cerise satin blouse, black leather skirt and black high-heeled pumps. Flesh-toned fully-fashioned stockings sheath her long well defined legs. She is wearing a blonde bob, her bangs direct your gaze to heavily madeup eyes, and she's wearing glistening ruby-red lipstick. She is mature but sexy...

My Wife Cheated, But I Liked It

by Jackb120 on May 6, 2019
Interracial Love

I've always been the average guy. I'm into normal things like working out, watching TV, and drinking beer with my friends. That said, I was shown porn as a teenager and found myself into interracial cuckolding and even crossdressing before I had my first real girlfriend. After highschool I moved away from home and stopped the crossdressing but kept the porn...

Tales of The Great Shift.

by joshman110 on Aug 2, 2019
Fantasy

On a other-wise average day on planet Earth, a strange force of energy passed through the planet. This force was The Great Shift, A supernatural that shifted the minds of 90% of the worlds population into different, random bodies. Say, an 80 year old man is shifted into the hot college co-ed down the street and his old body now has the mind of a twelve year...

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