Submissive Sissy Stories

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Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

He said "Call me Daddy"

by yvetteinpanties on Sep 12, 2018
Transsexuals & Crossdressers

His personal ad said: dom top daddy seeking submissive, trannies and crossdressers preferred. When I answered his ad as a submissive sissy offering full service as requested, attaching a picture of me in a short camisole and wearing a slave chain between my collar and handcuffs, captioned with "submissive sissy cocksucker can swallow 7 inches. Boi pussy trai...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Aztec Art - The Path to Submission Ch. 05

by Sputnik57 on Dec 23, 2017
BDSM

Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

The Prostate Exam Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...

Mama Mia Pt. 02

by grizzley123 on Jul 27, 2020
Fetish

This story contains many themes including cuckolding, gay sex, bsdm, incest and submission. If these are not your things, please skip. This is the second installment and it obviously helps to read the first part. The starting point here: I have just finished sucking off my temporary neighbor's cock. I have been set-up by my wife and her lover to be a submis...

Brad's Return Ch. 01

by grizzley123 on Sep 29, 2020
Loving Wives

Brad's Return, Chapter 1 ****************************************************** This is a continuation of the "Brad's Suggestion" stories I wrote a while back. It has similar cuckold and bisexuality themes, along with some lesbian and light BDSM fun thrown in. It emerged from my never-ending desire to put off the real work I should be doing. I hope you enj...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...