Sissy Wedding Stories

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My Sissy Wife Pt. 01

by IcelandSpar on Feb 11, 2019
Transgender & Crossdressers

I beep my car and ring the bell, holding the flowers I've just picked up on my way. Roses or lilies, I wondered, before settling on a combination of both. The door opens, and there you are, with your smile that cheers me up. We kiss there on the threshold, a peck that turns into a short kiss, then a longer one. You take the flowers from me, "aww, thank you,...

Siss the Bride

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

I was nervous. I mean, of course I was, how could I not be? Everyone is nervous on their wedding day, it's a big day, a commitment, especially when you're 26. I mean, it's not like I'm afraid of commitment, many of my boyfriends in the past would be able to tell you that; I wasn't exactly the type of person who would be reserved when it came to going all out...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

Outed and Married Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I entered the room with their drinks on the tray I was carrying I thought I would be pleasing to my husband. I made sure that my skirt was properly adjusted the way he likes me to wear skirts in the house. He insists that my rear not be covered below my tight little hole, insists that he have instant access to it if he wants to use it for his pleasure....

The Anniversary Present

by DrLuverotica on Sep 15, 2017
Transsexuals & Crossdressers

My wife, Jo, is a very hot, very sexy 40 year old doctor. For the past few years I've found it really difficult to please her sexually. That all changed when I bought her a Rampant Rabbit vibrator from Ann Summers for our tenth wedding anniversary. When Jo unwrapped the box containing the 8 inch silicon black vibrator she was giddy with excitement. I was de...

My Girlfriend's Sissy Roommate Ch. 04

by SEVERUSMAX on Nov 21, 2017
First Time

"So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it's between you and Rain, and I think that it's rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn't go so far as to call him a cuckold in the typical...

I Love Men to wear my Satin Panties Pt. 01

by Manndee on Apr 25, 2018
Transsexuals & Crossdressers

I was a quiet unassuming lad from the East end of London; I was 22 years old when I left home, it followed a number of pure flukes that all happened back to back, because of this I had had an amazing start to my life in my first job as a City trader. Unfortunately, things at home with my girlfriend were getting difficult after me losing my job. It was now 4...

Michelle's Hotel Bondage Experience

by michellelakes69 on Sep 13, 2017
Transsexuals & Crossdressers

As a timid and closet cross-dresser, my biggest fantasy was to have a sordid meet in a hotel room, where I left what happened up to another person, with only major limits discussed and agreed first. After months of search and waiting for the right person to come along, I finally met 'Sylvia' online, and I had finally decided to take the plunge to meet up wit...

Briefs No. 03: My Wife's Friends

by PatriciaFCartier on Jul 15, 2019
Transgender & Crossdressers

While sliding my silk stockings up my newly shaved legs, I thought about what got me here. My wife, Madison, told me after I'd been transformed that she'd planned this since before we married. She said she'd dated a boi in college for a while until the boi had been stolen from her by one of their professors. Said she'd liked the concept, if not the result. S...