Sissy Castrated Stories

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Orientation
Length
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Infinite Scroll

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

Sissy Downfall Ch. 02

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Revised version. all characters are adults. Part two. All Characters are over 18. * My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really...

You Knew

by TwistedPanties on Mar 18, 2020
Transgender & Crossdressers

You had willingly searched and jerked off to sissy porn for years. You regularly read Literotica fiction and would love to stroke yourself for hours. It was not uncommon for you to chat or flirt with other bloggers or online friends. You sought out a deeper role. The hypnosis of online flirts and short sissy skirts led to cravings, stronger and stronger with...

Tough Love Ch. 03

by justincbenedict on Sep 14, 2017
BDSM

Geneva smiled, looking at Kearney, who was snuffling in the corner. She knew how much he hated standing in the corner. Recently, she'd taken him to a BDSM party at the Scourge Society... Kearney had actually been involved with the Scourge Society even before Geneva, and was so excited about seeing his friends, and watching the gorgeous young girls get whipp...

Casey's Submissive Journey Pt. 07

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Note: This part of the story, and those to follow, occur after Karen had been accepted into the Lady's Club. ***** Karen spotted Betty Jean from across the room and she looked interesting. The ladies were all watching their husbands sucking and fucking each other in full drag, it was Fag Night at the Lady's Club and the sissies were giving them a really go...

The Fate of Her Lovers

by BigK10 on Sep 15, 2017
Loving Wives

Chapter 1 My wife, Juanita, set across the breakfast table from me, just as we had for the last twenty-four years of our married life. It was a Thursday morning in late September and the leaves of the trees in our backyard had begun to turn various shades of yellow and tan. She was enjoying that view through the window of our breakfast nook, while I read th...

Respect Ch. 01

by rachaelross on Sep 13, 2017
Loving Wives

Note: This story is significantly changed from the original post on ASSM and SOL particularly in Chapters 1 and 8 ...thanks for reading -rr =-=-=-=-=-=-=-=-=-=-= This story is composed of 4 chapters of approximately 10K words each. Copyright 2006 Rachael Ross all rights reserved. * I couldn't bear the thought of sneaking around all the time. Going behin...

A Pound of Flesh Ch. 05-06

by SEVERUSMAX on Sep 14, 2017
Group Sex

Chapter 5 When I awoke the next morning, it was to the sound of rather wild, raunchy sex, of course, but it wasn't what I thought. Nicky and Chelsea were getting it on, but she was hitting him from behind with a strap-on dildo. My fiancee was pegging my boyfriend, while his fiancee watched and pleasured herself in response. He didn't seem to mind it, either...

Cassy's Game Ch. 5

by wormwood on Sep 19, 2017
BDSM

Mistress Lindsay took no crap. Her orders were precise, her manner direct. I went from quiet subservience on the kitchen floor to quietly licking the grime from her street shoes in the living room. The taste was terrible and the grit on my tongue and my teeth made me nauseous. I took advantage of my actions to survey Mistress Lindsay, about forty years old...

Freedom and the Widow Ch. 16

by Sputnik57 on Sep 14, 2017
BDSM

Victoria was very gracious in her treatment of Eric after Marcel left them; he was summoned to her bed and she cuddled him lovingly between the sheets. She had truly shown him his place; he had accepted his duties and this had thoroughly stimulated her. Eric, for his part was also still excited with respect to his thorough degradation and utter humiliation b...