Sissy Bukkake Stories

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Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

Julie is a Whore Ch. 05

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch. 5 I am a sissy cross dresser that has been living as a woman in Madame's brothel for about 3 years now. During that time I have perfected my skills as a cock sucker and a top notch prostitute. I have my own room in the brothel where I live and entertain clients in other parts of the House. My sister, Becca, does not live in the brothel, but whenever she...

Candy's Bukkake Moment

by Stillherer on Sep 17, 2017
BDSM

She had been so kind, so understanding of his needs, so nonjudgmental that he found himself gratefully allowing her to make him into the girl he had always wanted to be. When she hadn't freaked upon discovering his stash of female underwear and had honestly tired to understand what it was about them that excited him so he couldn't believe his luck. His bigge...

Julie is a Whore Ch. 10

by Pretty_Sissy_Julie on Sep 14, 2020
BDSM

This is a story about BDSM and pleasure. Please understand everything done was consensual The scenes are no worse than you might see in the movies. There is no actual "snuffing." All of the women involved savored the experienced and had intense orgasms. This story is for your entertainment only. My name is julie, I have been living as a sissy whore for year...

Julie is a Whore Ch. 11

by Pretty_Sissy_Julie on Sep 28, 2020
BDSM

This is a story about BDSM and pleasure. Please understand everything done was consensual The scenes are no worse than you might see in the movies. There is no actual "snuffing." All of the women involved savored the experienced and had intense orgasms. This story is for your entertainment only. If you really want to enjoy this story, you need to read Chapt...

The Naked Bleached Blonde "Sissy Barbie Bimbo"

by Crissy on Apr 22, 2025

Did You Know? According to a study conducted on 293 female college students at the State University of New York in Albany, exposure to semen can lower symptoms of depression. And it’s mighty healthy: One teaspoon of semen contains over 200 proteins and several helpful vitamins and minerals including vitamin C, calcium, chlorine, citric acid, fructose, lacti...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

HypnoSissy: Becoming a Cocksucker

by silkstockingslover on Sep 18, 2017
Fetish

Summary: Straight guy watches porn tapes that are not what they seem. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist in the first place. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to goamz86, Robert, DomMasterJim and Wayne for editing. Category: This...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy 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 by a very supportive girlfriend in pantyho...