Sissy Castrated Stories

7,169 results
Orientation
Length
Source
Infinite Scroll

A Cuckold's Diary Ch. 24

by Paul Pines on Sep 19, 2017
Loving Wives

Making it Real A Cuckold's Diary, Chapter 35 May, 2012 PLEASE, folks: this is a story about cuckolding. Honest, I wouldn't lie to you! If you read it, you are going to hear about cuckolding. If this will upset you, may I suggest that you either a) don't read it, or b) don't get your nose out of joint when you get upset. I post this in the Loving Wives Sect...

Requiem: A Love Story

by Royal_Prince on Sep 16, 2017
Romance

Beneath the requiem lies eloquent verses; its tenants transgress while in mourning. Yet bequeathed of its passerby’s there are dormant cries that echo. I am there among them. We envision plains and grains of gold dancing westward into the receiving winds. We can hear thunder of past and present as they come together in a splendid display of courage and con...

50 Shades Of Pale Pink Sissy Ch. 03

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Fiction with adult themes. All characters are over 18. * A splitting headache greeted me as I awoke. The soft surface I was lying upon seemed to be moving beneath me, rolling from side to side with occasional pitches from front and rear. In my confused state I wondered if the feeling was related to the headache and the vague memory of being drugged. The r...

Clara: Summer Rose Conquers All

by caprine on Sep 14, 2017
Erotic Couplings

[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. As such, the story may or may not totally conform to reality. With some occasional historical exceptions, all other locations, events, and characters are entirely fictitious and any resemblance to actual persons,...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...