Sissy Girlfriend Stories

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Caught by My Bully and Exgf Ch. 01

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

Dear readers, this my first erotic story, all of protagonists here are fictional consenting adults, I hope you enjoy reading it! ***** I was 21 year old student with part-time job, living in a small flat in big city when this all happened. I broke up with my girlfriend Michelle, after seven month long relationship with her, because I received a video from...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Mum & Sister Dress Him Up

by Quietoldie on Sep 14, 2017
Transsexuals & Crossdressers

"This is my rented flat you know Michelle. It's not fair you being like this with me. I've always been good to you haven't I?" Peter says. He often seems to get into situations like this. He was never very good about sticking up for himself. Now his girlfriend is chucking him out just because she found him dressing up in her things. "I just don't want to l...

Tranny G is a Nymph

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

It has been a long winter and I have not seen Chris or Tranny G in a long time. Chris lives in a place too cold and it is difficult for him to travel. During those cold months, and without my being near, G has been in hiding. I have hinted, begged and pleaded with Chris to find a weekend to travel to see me. He needs a break from work and the cold and I need...

Thank You For My Life

by darklace on Sep 16, 2017
Transsexuals & Crossdressers

It was an unseasonably warm and sunny February day and so I didn't feel cold even though my legs were only covered by my black seamed stockings. Taking the keys out of my purse, I walked up the snowy steps to his house and let myself in. It was a lovely house, decorated with sports memorabilia and photos of him in faraway countries on his aid trips. He was a...

The Vixen

by TheEroticProspero on Oct 11, 2017
Transsexuals & Crossdressers

Simon first saw her as he walked through one of the rougher streets in town. He couldn't help but stare at her long red hair, sharp facial features, milky white skin and the tight velvet jacket she wore over an even tighter leather dress. He looked her up and down, admiring her modest but perky bust, her thin but shapely body and her simply perfect legs. Si...

A New Way Of Life

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, blue eyes and jaw length blond hair. They loved me in high sch...

Trapped as a sissy in a fanasy world.

by Duke Montefort on Nov 14, 2019
Fetish

Eugene has an obsession with video games almost shutting out his friends and family. Feeling they have no choice the family begs a videogame company to help them bond with him. The company agrees they test the family can beta test the game, and bond. They even promised that he could not come out until he had properly bonded with each family member seprately....

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Casey's Submissive Journey Pt. 04

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part Two After putting on the movie Angie walked to the side of the bed and carefully removed her hat, gloves and shoes. As she did she called Debbie over and told him to lie down and get comfy. He took a sip of his drink, put it on the nightstand, then laid down on his side and watched the video. Soon after he felt Angie's w...

Ashley Gets a Real Fucking

by Equinox31 on Sep 13, 2017
First Time

*This story is fictional. Don't read if things such as cuckolding, and male on males offends you* * This is the story of how a college girlfriend turned her wimp boyfriend into a cuckold. Mike and Ashley started dating when we were both 16 and they were now 21 but went to different colleges. All of Mike's friends would tell him to watch out, and that she m...