High Heels, Sissy, Wife Stories

245,606 results
Orientation
Length
Source
Infinite Scroll

Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...

Creating Ginger Ch. 06

by Ms_Allison on Jun 9, 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. In the below story I refer to the male character several ways but try to maintain a consistent in referr...

Wife in Control Ch. 06

by wifetoy on Sep 25, 2017
Fetish

I will bring you your Magic Wand and Trigasm. And suck on your toes, while you enjoy every spasm. Your humiliated sissy in panties, tights, and stilettos. This is the sixth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full...

Sissy Cuckold Husband

by bisissystephenie on Sep 16, 2017
Fetish

If you don't like sissy, cuckold, bisexual men stories, then please don't read it only to complain. You look stupid! ***** Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at...

Miss Jennifer Fucks Little Tiffie

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

The Saturday after Miss Jennifer had her boyfriend fuck my pussy/bottom, she called to me while I was doing her laundry and told me to come to her room. As I entered, she told me to come and stand in front of her, where she was lying on her bed. I was, of course, dressed like a proper little housewife, with my pink lace bra stuffed with my big 54DD falsies...

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...

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

Becoming My Wife's Sissy Slut

by SissyFaye on Jun 8, 2020
Transgender & Crossdressers

All alone, the kids are gone! My wife and I are cuddling naked in the bed. I'm all locked and stiff in my cage. She rolls over and kisses me deeply and forcefully good morning. She pulls away, both of us breathing heavily from the passionate kiss. She says "Good morning, my sissy, I see that made you strain in your cage. Do you wish to be released?" I...

From Her Ex-Boss to her Bitch Pt. 02

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

The day had been excellent, and the end of it was looking up. Pete had thought he might get a bit of fun with Rachel, but now he knew she was a true Domme and now that he'd admitted to her his submissive leanings, it looked as though it was going to be a very interesting few hours. Bring it on, he thought. Rachel looked at him as a predator looks at prey, h...

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. ~~~~~~~~~~~~~~~...