Pegging Crossdressing Stories

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Orientation
Length
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Infinite Scroll

Your Adventures in Mixed Wrestling

by EugPad21 on Nov 20, 2020
Fetish

You walk through the doors. Excited to begin your first day as part of the Mixed Wrestling Federation. You walk up to the desk where a receptionist is waiting for you. "Hello, How can I help?" She asks "Hi my name is (Insert your name). I'm here for to sign up for the Mixed Wrestling Federation" "Ahhh yes" she said, "We got...

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Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

Pegging Fantasies

by the_shires on Sep 25, 2017
Fetish

Alan looked over at Jill. As usual her face was buried deep in a stack of books. Not one book, or even two. At least four. She was studying for her exams, and her face showed intense concentration. He sighed. They had a matter of weeks left before they were out of college and working full-time jobs. There was a lot of anxiety written around them and he knew...

Somali Queen In Ottawa Ch. 05

by Samuelx on Sep 12, 2017
Fetish

The things I do for love never cease to amaze me, ladies and gentlemen. The other day, after a night of passion, I tossed my girlfriend Yasmin Hussein my house keys, mainly because I wanted more access to her pussy, and the sexy Somali chick got it into her Hijab-wrapped head that I wanted her to move in with me. I was terrified of Yasmin moving in with me b...

Interracial Pegging : Amen!

by Samuelx on Sep 11, 2017
Interracial Love

Hey, there. My name is Barry Etienne. A big and tall young Black man of Haitian descent living in the City of Nepean, Province of Ontario. And for the longest time, I've been desperately lonely. Almost to the point of wishing my existence would end. My life seemed that dull, man. I felt like I had nothing real going on. From my classes at Carleton University...

White Women Got Big Dicks Too

by Samuelx on Sep 17, 2017
BDSM

My name is Susan Edgar. I'm a six-foot-tall, blonde-haired, green-eyed, forty-something Irishwoman living in Boston. I'm happily married to Stuart Lemond, a tall and good-looking, red-haired gentleman of French-Canadian descent. Lately, our relationship has been rocky. Partly because the passion is gone. So, we decided to spice things up. Bringing new people...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

My First Pegging Experience

by doncamillo on Nov 19, 2018
Fetish

When I mentioned my interest in pegging to my professional dom friend her eyes sparkled. We were out drinking and have had quite a lot of drinks already. So it wasn't surprising that we ended up in her studio to satisfy my curiosity. After we got in she put her bag to the side, took off her jacket, helped me take mine off and stood in front of me. Looked u...

A late night at the office

by morpheus_arms on Aug 30, 2019
Miscellaneous

This is a Hub Page to make it easier to select a path the reader would enjoy most right from the start and as such very much a WIP. {Morpheus here: This story is what Germans call a "Fingerübung", a finger excercise to test out how to structure and maintain a first complex story all of my own. As such, expect some newbie mistakes and such, even tho...

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