Sissy Boy Hotwife Stories

109,316 results
Orientation
Length
Source
Infinite Scroll

The Making of a Mistress Pt. 04

by EiryCGar on Jul 13, 2020
BDSM

Author's note: The saga of Mistress-in-Training Marie and her sissy Charles has reached the point of their marriage. After the ceremony, Marie achieves her ambition and becomes a hotwife, making Charles a cuckold in the process As in all my fictional stories, all characters are over the age of eighteen, and all sexual practices described are performed conse...

The Guy in My Wife's Panties

by Candyboi on May 1, 2018
Transsexuals & Crossdressers

The catalyst for the paradigm shift in the relationship with my wife of twenty years was something that happened at the beginning of December - though, truth be told (as you'll see), there were several other naughty escapades throughout the autumn that really should have awoken me to the realisation that Carla was becoming the dominant one in our relationshi...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

The Making of a Mistress Pt. 03

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This fictional series about a character first introduced in my "Coming Home; Coming Out" serial continues with Marie, now engaged, is going to meet Charles's parents. She also takes Charles to meet her mentor, Dr Sara Walters and her sissy cuckold, Paula. As in all of my work, every character is over 18 years of age, and all sexual practices a...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...

The Making of a Mistress Pt. 06

by EiryCGar on Sep 14, 2020
BDSM

Author's note: 'All things must pass' and I feel that this series has reached a natural conclusion. As always, I must point out that all players in this fictional saga are aged 18 or older, and all sexual acts are consensual. The Making of a Mistress Chapter 6: Cwm Pechod's Cuckold Community The invitations to the party for the combined wedding anniversary...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Types of Cuckolds

by cuckwhofucks on Sep 14, 2017
Reviews & Essays

What does it mean to be a cuckold? It actually means many different things to different cuckolds. But let's start at the beginning: The truth vs. the Truth. The Truth, or an absolute Truth, is actually unnamable, or rather it exists, but when you try to interpret it and put words to it, it becomes one of very many truths, as many truths as there are peopl...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

The Perfect Handjob

by Ricky_writes on Sep 13, 2017
Loving Wives

I've been married for 20 years. It didn't take my wife Tammy and I too long to figure out that I had a much stronger sex-drive than she did. Frankly I have thoughts of sex about 5 times an hour and my wife has the same thoughts about once every 5 days. I'm sure it is a rare occurrence when two married people have the exact same desired level for sex. The way...