Sissy Cuckold Crossdress Cream Pie Eating Stories

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Orientation
Length
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Infinite Scroll

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Becoming a Sissy Cuckold Ch. 01

by Pantieslave on Mar 27, 2019
Fetish

Beth and Dan were married very young, just 20 years old each. As such both were virgins when they married. Beth wasn't an outstanding beauty but very attractive with a nice body and very nice breasts, 36D. Dan, on the other hand, was rather feminine looking and wore his hair long, in a ponytail. Being slightly built, on more than one occasion he was mistaken...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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Coming Home, Coming Out Pt. 05

by EiryCGar on Mar 30, 2020
BDSM

Author's note: This fictional series continues with part five. Both Dr Sara and Paul and Dr Mary and Clarice (Cee) have secrets to share. The narrative in this chapter takes place in the week prior to Dr Mary and Cee leaving their respective jobs in the city, and moving go the village of Cwm Pechod, to take up new posts in the medical practice headed by Dr S...

Three Loving Wives

by donaldelliott11 on Mar 2, 2020
Loving Wives

This story contains three loving wives. I counted them. *** "I don't know why you haven't been able to seal the deal with Nancy," Peter Johnson said to his best friend. "She just doesn't seem interested in fucking me," Michael Dodson replied. "I'm like stuck on your wife's friend list." They were sunbathing next to the Johnsons' pool, naked, as they did...

Slut Wife - One Woman's Guide Pt. 03

by policywank on Nov 30, 2017
Loving Wives

So now you are hot wife and cuckold. Hopefully you have both taken the time to adjust to this new reality, but there is still much to be done to establish a true paradigm shift. My previous guides talked about how to lead your husband to this point by establishing the necessary understanding and acceptance as well as providing some thoughts for him and how...

The twisted DM

by Nobody567 on Nov 21, 2019
Fantasy

Authors notes: please like and comment my stuff I desperately desire your feedback and approval. I am new at this and recently redid the intro hope you like it. A being beyond space and time whose goal is to torture, torment, pleasure and change his players in ways that you cannot begin to fathom for his entertainment and pleasure. He sits at multiple tables...

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Fucked a New Hotwife Pt. 01

by MattieG on Sep 14, 2017
Loving Wives

Last night I met a new Hotwife/Cuck couple for the first time. He is very submissive to her, and she was craving someone very dominant that she could let go with. We had chatted by text for a couple of days and I figured we would meet in a few days have coffee and maybe meet and play in a couple weeks. With all of the talk her cuck was super excited and was...

Limp No More Pt. 03

by notunique on Jul 10, 2018
Loving Wives

As Roger and his well fucked wife made their way toward their hotel suite, he was filled with anticipation of more first time sexual experiences with her. Although she rarely viewed porn with her husband, she knew all about the kinds of themes and content of cuckold porn that Roger favored. She knew that almost every cuckold hubby longs for the same thing -...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...