10 Inch Heels Sissy Stories Stories

215,808 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

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...

Few of My Ultra-Perverted Fantasies

by whiteboibbclicker on Sep 16, 2017
Transsexuals & Crossdressers

Hello, I am a white boi who's addicted to sissy porn and have a lot of wicked and perverted fantasies. In this list, I will enumerate some of them. I would ask the readers to name the one that they like the most in the comments section so I can write a story about it. Authors are more than welcome if they want to write about any of the themes mentioned here...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Mistress Chantel, Tranny Dominatrix Ch. 15

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fifteen: We Meet Each Other's Parents and There Is A Wedding Ready to Go. [Sunday late morning]. "How many sissy maids have agreed to come clean for us Hun?" Kerri asks. "Three little sweetie maids Babe." I smile and reply. "They will be by on Wednesday before our Friday wedding. They are all so excited to play sissy house maids for us while t...

Sissy Pool Wager Pt. 01

by maxy007 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself! As you could imagine, an 18-year-old horny boy like myself really got into my porn, which f...