Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Sandra and Stevie Ch. 35

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the thirty-fifth installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty-four episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I st...

The Chief Pt. 01

by Aunt_Joanne on Sep 14, 2017
Transsexuals & Crossdressers

When I was 19, I was still trying to figure out what I wanted to do with my life. I had just dropped out of college and was working construction in my home town. Construction work was hard, but I liked it. The guys I worked with were cool. It was honest work and it paid enough for me to keep my head above water. It was also a "manly" pursuit, and that was im...

Casey's Submissive Journey Pt. 07

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Note: This part of the story, and those to follow, occur after Karen had been accepted into the Lady's Club. ***** Karen spotted Betty Jean from across the room and she looked interesting. The ladies were all watching their husbands sucking and fucking each other in full drag, it was Fag Night at the Lady's Club and the sissies were giving them a really go...

Sandra and Stevie Ch. 28

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the twenty-eighth installment in a series entitled "Sandra and Stevie". If you have not read the previous twenty-seven episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I...

Girlboy Diary Day 01

by Hartford on Sep 16, 2017
Transsexuals & Crossdressers

Day 1 It might never have happened if my aunt hadn't caught me wearing girl clothes at the mall, clothes plus a wig and make up. How she knew it was me is a mystery because I can pass like nobody's business. Hate to brag but it's a fact. Anyway, my aunt followed me, got some still photos and video on her blackberry, and showed it to Mother. I found out six...

Randy's New Life

by Rich5Spot on Sep 14, 2017
Fetish

Noreen is a 29 year old lovely married woman who has been working in my office for the last 7 years. She has been married for the last five years to and seemed to lead a fairly normal, but dull lifestyle. She is also a gorgeous brunette, 5' 1" tall, 100 lbs with a pretty smile, perky A cup breasts, a great ass and super sexy legs. I have been drooling over h...

Louis Makes a Decision Ch. 03

by Goodhusband on Sep 19, 2017
BDSM

Note: This story is the third episode in a short series entitled "Louis Makes a Decision". If you have not read the previous two episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories I strongly r...

Sandra and Stevie Ch. 27

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the twenty-seventh installment in a series entitled "Sandra and Stevie". If you have not read the previous twenty-six episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I s...

How I Cucked My Husband Ch. 03

by wifelvrman on Sep 17, 2017
Loving Wives

Probably the final part of my story. To continue from Part 2. Bob and I were driving down the highway, my blouse unbuttoned, and his cum leaking out of my pussy from just having been fucked in public. Bob had me put the blindfold back on. I heard him pull off the highway. He drove a little further, stopped, told me to wait in the car, and he got out. I cou...

Sorority Switch Pt. 01

by Sissy_simone on Sep 11, 2018
Transsexuals & Crossdressers

The summer leading into sophomore year at the university was like any other, until my I accidentally broke my twin sister's jaw. We were inseparable since birth and frequented many of the bars a few times a week, except for one fateful Saturday 2 weeks before work week started for her. Work week is the week before rush week when all of the sororities reunite...