Sissy Boyfriend Stories

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Sarah had to Wear Little Panties

by SarahCD on Dec 25, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ------------------------------------------------------- It was Saturday morning and I decided to get my laundry done before going ou...

Pat's Panty Slave Ch. 03

by Sissyfreak on Sep 16, 2017
Transsexuals & Crossdressers

Having been humiliated for a second time, I thought things couldn't get any worse, how wrong could I be! I was sat at home one day, kids at school, Wife out shopping, when there was a knock at the front door. Jo was standing there with a carrier bag. She threw the bag to me and ordered me to put on the items within, then come to her house next door. I looked...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

A Girl And Her Sissy

by TollWard on Sep 18, 2017
Transsexuals & Crossdressers

Life is good. Life is really, really good. As I write this I'm sipping on a very expensive wine and wearing a very expensive dress while sitting in my very expensive apartment. I no longer work, having not needed to earn my own income for little more than a year now. That probably leads you to wonder how I pay for all my nice things. Well while I enjoy my lu...

Little Panties for a Little Cock

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed they belonged to the you...

My Girlfriend's Sissy Roommate Ch. 03

by SEVERUSMAX on Sep 16, 2017
Transsexuals & Crossdressers

I had to admit to myself that Larissa had never looked as sexy and drop-dead gorgeous as she did right then, bent over as I fucked her from behind and she took me deeper inside her twat. I fucked my new girlfriend so hard that she moaned and pushed back at Rain and me. He could feel the force of her hips and ass as she bumped her crack against his tongue. I...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

Making a Cuckold

by jessijazz66 on Sep 19, 2017
BDSM

Brandi spoke nervously to her friend Jessica before she hung up the phone, "you're sure this will work?" Jessica understood her friend's fears, ever since they had begun discussing this plan of action. Jessica knew that Brandi was just starting to explore the depths of female dominance, and she knew that Brandi was worried about how her boyfriend, Brian, wo...

Sarah was Humiliated

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I got myself into trouble the other day. I live on the second floor in a little apartment building. I was just starting up the stairs when I looked up and saw that my neighbors were out on the landing. She had her back to the railing and was talking to her boyfriend. She was wearing a short white cheerleaders skirt. I froze and stood there trying to look up...