Feminizing First Step Stories

319,459 results
Orientation
Length
Source
Infinite Scroll

An Intimate Caning?

by deference on Nov 26, 2017
BDSM

An oxymoron is said to exist when two words are used whose meaning does not seem to fit together such as jumbo shrimp or government intelligence. No doubt, the words 'intimate caning' would also fit this definition. However, while a majority would view corporal punishment and domestic discipline as either sadistic or sexually deviant, a minority have found i...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...

Reversals Ch. 08

by RachelClark on Sep 11, 2017
Fetish

CHAPTER EIGHT Samantha's Surprise Julia sat alone in Samantha's office. It had been almost twenty minutes since she had left to fetch another document they needed to finalize Julia's promotion. Impatience was settling in. Oddly enough, Julia had never been in Samantha's office before, she never mentioned she even had one. Thinking on it, Julia realized th...

Reversals Ch. 04

by RachelClark on Sep 11, 2017
Fetish

CHAPTER FOUR AGen Julia took another sip of wine and gently rested the long-stemmed glass back to the table as Samantha smiled at her affectionately. The burgundy liquid looked regal in the soft lighting of the restaurant, sitting upon the pearl-white tablecloth adorning their table. Adding to the ambiance, a single rose rested in a slender, glass vase, in...

Impeccable Taste Pt. 02

by dreadknots on Mar 2, 2020
Sci-Fi & Fantasy

This story features a boy getting a pussy, threats of breeding by demon girlcock, and all kinds of dirty talk. So if that's your jam, read on fellow patrician! This is a sequel, or really a second unrelated part I suppose, to another story which you can read here! You don't need to have read the first one, but it might help to establish their relationship!...

The Writer's Secret Ch. 11-12

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? * Chapter 11: Pierced Over the next two days, Loren got used to life as a sexy maid to a woman of whim. Stephanie got used t...

Spanking Night Ch. 04

by Angelscuck on Sep 14, 2017
BDSM

I slowly rolled over to allow my wife access to my bare bottom. I was still in shock, my mind reeling from what she had just confessed to me. This was no mind game. I had the proof-positive taste still lingering in my mouth. Smack. Suddenly the sound and sting of the cane against my skin brought me back to reality. It hurt like hell! I didn't cry out but I...

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...

Five Positions Two Loads

by lynntg0444 on Oct 21, 2019
Transgender & Crossdressers

It took six months from my first blood test until surgery was prescribed. Unfortunately this was only a slightly feminizing surgery - I was diagnosed with prostate cancer, and the simplest solution was a radical removal of the whole organ. Needless to say, this was extremely depressing as I had become accustomed to mind-blowing orgasms through prostate stimu...

Getting It Off My Chest Again

by dirtyjoe69 on Sep 16, 2017
Reviews & Essays

Getting it off my chest again More rants from DirtyJoe Yep it is me again, DirtyJoe. How have you all been? Well I have been pretty darn good lately but that doesn't mean I still don't have issues to discuss. This time I will be asking questions that I hope I get answers too. Does anyone else find the United Nations a little messed up? I mean how do you g...