Sissy Husbands Stories

24,164 results
Orientation
Length
Source
Infinite Scroll

Sam's Panties Ch. 02

by Quietoldie on Sep 19, 2017
Transsexuals & Crossdressers

At the end of their holiday the two couples exchange email addresses and phone numbers. Jean and Ken live in the North East part of England whilst Mike and Sam live near London. The 250 miles separating them is no bar to them meeting up from time to time when Jean can enjoy her new found desire for extramarital sex with both Mike and Sam. Her cuckold Ken is...

Creating Ginger Ch. 07

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. Hopefully you've read the previous chapters to understand the nuances of this storyline. ~~~~~~~~~~~~~~~...

Cuckold CEO Ch. 07

by drdick69 on Oct 16, 2018
Fetish

I awoke Saturday to the sounds of running water. My wife was already up and in the shower. My head was still swimming from that activities of the night before. Our playful cuckold game had taken us to a different level, with me being submissively used for the pleasure of my wife and her lover. More worryingly, the comment my wife made, before I went to bed,...

The Challenge - Wear a Thong

by taraterry on Oct 11, 2017
Transsexuals & Crossdressers

There is something deliciously naughty about a boy wearing women's thong panties for a day, after all, the first time you wear a thong all day long, especially on a week day, you will be going about your normal routine. Whether it be to class, to work, or whatever you normally do, you will have it on all day, even when you're not fully sexually aroused. Why...

The New Swim Team Pt. 02

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this story in late 2015. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever happened in real life. All the names, places, or events living or dead are purely coincidental. ***** Part 2~ The Teams First Practice. Steven turned of...

Wendy The Haitian Cuckoldress

by Samuelx on Sep 16, 2017
Interracial Love

My name is Wendy Stephania Polydor and I'm a 29-year-old Black woman of Haitian descent living in the City of Boston, Massachusetts. I work as a Nurse at a certain hospital and I am the proud mother of a son, Jefferson, and a daughter, Lilandra. Life as a single mother isn't easy, and the fact that my ex-husband Alan Stephenson, a Boston-area cop, is a miser...

Out Shopping with Lisa

by sissyboytoview on Sep 16, 2017
Transsexuals & Crossdressers

Ever since the day she caught me wanking, dressed in her bra and panties, my partner Lisa had made the rules that allowed me to wear female underwear - always when we go out together, sometimes when I go out on my own, and always when I go to the pub with my mates, (in case I fancy my chances with another woman). She has also developed a habit of tying up my...

Finding Her Secret Emails Ch. 03

by Quietoldie on Sep 26, 2017
Transsexuals & Crossdressers

Our sex life continues as before and I'm very happy about it. Occasionally Carol lies on her back and asks me to mount her or suggests we do it doggy fashion with her kneeling and me taking her from behind. This usually coincides with my badminton night so I assume she's pretending that it's Mr Police Person fucking her. If I'm behind her I pretend to be all...

Counselling Changed Our Marriage Ch. 02

by Quietoldie on Dec 1, 2017
Transsexuals & Crossdressers

I am grateful to another member of Literotica for the story line and about half the content of this story. I have thoroughly enjoyed the collaboration and have found working with a woman has informed my own writing. Chapter 3 will follow shortly. ***** Third Joint Interview Emily and I arrive at their marriage counselling session a bit earlier than their...

Black Man One Ch. 20

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

I could hardly comprehend how nervous I felt as I began walking down to the first floor of the condo building. The greater part of me wanted to know how the other 11 white husbands still living here felt, and why I had not seen them more than a few times in weeks. Another part of me was truly afraid to know. My purpose was unclear to me at the time. I supp...