Wife Sissy Stories

124,824 results
Orientation
Length
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Infinite Scroll

Yes, Mommy Ch. 03

by searic on Sep 17, 2017
BDSM

Here is the third installment of a story of loving spouses, the husband a sissy submissive to his Mistress/Mommy. She has invited over a girlfriend to witness and perhaps participate in his humiliation and degradation. At the end of Part II, the women were on the couch and the little sissy was on the floor. He obeys his wife's command to beg. * "Oh, please...

The French Trip Pt. 01

by DrLuverotica on Sep 16, 2017
Transsexuals & Crossdressers

We'd only arrived in the South of France late the night before, but already Jo my sexy, blonde 40 year old wife was gagging for it. We were driving along a fairly quiet road populated by overhanging trees with the Pyrenees providing a dramatic backdrop. Jo was dressed in a short blue skirt, white button down top which was undone giving me a very distracting...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

This is What I Want

by bisissystephenie on Jan 22, 2020
Fetish

My wife Pam has started going out for a "Girls Night Out" and this time she came back a little tipsy. And very late! She knows how I love to give oral sex to her and she hardly ever says "No". We went to the bedroom and she laid back on the bed. I got in my position, on my knees and between her legs. I started kissing her knees and going up. She stopped m...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...