Sissification Stories

145 results
Orientation
Length
Source
Infinite Scroll

Everything Has a Price Ch. 06

by MALIBUMAN666 on Sep 14, 2017
BDSM

Author's note: This story doesn't seem to be as popular as some of my others, I don't know why that is particularly... it's a lot more 'real', certainly more 'real' than 'Owned!' or 'Out of Your Hands' which are both quite far-fetched really... It doesn't bother me particularly I'm just interested to know people's opinion and so I really do welcome your feed...

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...

Journey into Feminization Ch. 01

by KneelingNancy on Jul 14, 2020
BDSM

***Chapter 01 - The Beginning Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.). During my chil...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

Thoughts on Cuckolding

by Youami on Apr 3, 2018
Reviews & Essays

Until a few years ago, I had only a vague understanding of the term "cuckold" as it related to sexual relations between couples. As ignorant as I was I thought it had something to do with cheating. However, thanks to the overwhelming number of cuckold stories contributed to Literotica, I have been able to build a better appreciation of this term and the many...

Dominant vs. Submissive

by tow2b on Sep 12, 2017
Reviews & Essays

Professionally Dominant, personally submissive The alternate titles: The title above represents the most succinct description for this article, but there is far more to this than the title suggests. This has been posted to reviews and essays for good reason; this is not about sex per se. Neither is it about dominance/submission as a fetish, lifestyle...

The Dominatrix Order Pt. 01 Ch. 10

by Jwwsmith on Dec 25, 2018
BDSM

Following the party at Isabella's castle, Nadia and Slave boy returned to Nadia's home. Nadia instructed Slave boy to rinse off with the hose while she went inside and drew herself a bath. Once Slave boy had washed the evenings work from his twenty year old body, he went inside. He saw his Mistress. Everything stopped. Nadia stood at the hallway's entrance,...

Contagion 63X - Viral Transformation

by Aroband on Feb 20, 2020
Fantasy

From the records of Advanced Bio-hazard Research Facility Psi Omega - Location **Redacted** ---===Virus 209-q===--- Codename: 63X Virus 209 was designed as a way to naturally incapacitate the human body by temporarily drastically increasing the production of certain hormones in the body. Strand q was a dangerous outlier in 209's evolution that went far beyon...

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Teasing Together

by Scarlet_Pen on Sep 14, 2017
BDSM

Ian was at work when an SMS message from Chrissie flashed up on his phone. "We've got mail. Got to open it together – hurry home tonight. Love you xxx." His face split with a smile, knowing both he and Chrissie would be spending the next few hours in feverish anticipation of what may lie in the mail message. A few weeks ago, they'd been chatting idly about...

Cucky Gets Lucky Ch. 03

by Tosshhh_ on Oct 5, 2020
Fetish

Things had really changed in our relationship. Now that we were open to everyone about Karen being my slut things escalated quickly. Karen sat John down and had a long talk explaining to him that he was now to be abstinent forever. After entertaining all our friends to the sounds of me fucking his wife's brains out he had resigned himself to his fate. The...