Seduced Into Sissyhood Erotica Stories

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Infinite Scroll

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Thoughts On Writing Erotica

by slitlicker69 on Sep 13, 2017
Reviews & Essays

Thoughts On Writing Erotica: POVs, Plots, Pacing, And Pudendas To begin this discussion, I would like to start with MY definition of Erotica vs. Pornography, and Erotica vs. mainstream fiction. Many people are confused over the lines between mainstream fiction that has erotic elements in it, and true erotica. Likewise, there is great confusion, and differen...

What Every Sissy Knows

by BelissimaSissy on Jul 31, 2018
Transsexuals & Crossdressers

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy! ***** I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could he...

Seduction to Hell

by iRoNic on Jun 19, 2017
Fantasy

**Disclaimer: All characters are aged 18 and above, all characters and locations are fictional, and content will be removed if given a reasonable request with a reasonable reason** *Conditionals are used and custom names are available* Welcome to Seduction to Hell. This is my first story about the protagonist (You) having to select your choices throughout th...

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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...

Another Sissy Shopping Adventure

by sissysherry2 on Jul 18, 2018
BDSM

In my last story, I related a story about a mistress who gave me a sissy assignment several years ago. This involved going to a mall and getting a makeover and getting girly clothes. Like the other story in this topic, there's no sex just some good old fashioned humiliation. This is the latest adventure and I hope you enjoy it! ********************* I h...

The Feminisation Initiative Ch. 02

by Slipperylock on Oct 30, 2018
Transgender & Crossdressers

The room was quiet and dark - the only illumination spilled from the Observation Room window over the eight beds and their occupants. The only sound in the room was the whirring of the machines, and the occasional muffled moan. In the Observation Room booth, the Director of the F-center fiddled with the control panel nervously and jogged her leg. The Presid...

Sanjay to Sanjana Ch. 01

by smalltownsissy on Mar 11, 2019
Transgender & Crossdressers

A luxury apartment on the banks of river Yamuna. When his parents talked about a gift as he was readying for college, he didn't expect them to go all out and buy him an apartment. Sanjay, being the only son was pampered enough by his parents already that he never felt short of anything. Like most Punjabi (a state in Northwest India) boys, Sanjay was fair....

How To Write Lesbian Sex Scenes

by Colleen Thomas on Sep 14, 2017
How To

As the title implies this little article is intended for guys who wish to write lesbian themed sex scenes that appeal to women. While I claim no more expertise at it than other writers, I have been asked by a few people to look at their submissions in the category and one of these prevailed upon me to write this little piece. Thanks Rumple. The first thing...

Tax Day Relief

by ThinkingDog on May 29, 2018
Toys & Masturbation

This is a true story as all mine are. I hope you enjoy! *** Sometime ago I commented on a post that a gal (Suzanne) made online and she replied back to me. It wasn't anything naughty at all. We emailed back and forth a couple times and I found out that she is Asian and petite. Eventually the subject of each others naughty sides came up and I learned a lit...