Chastity Sissy Stories

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Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

On the Hunt Ch. 03

by Lisa2506 on Jul 31, 2019
Exhibitionist & Voyeur

Hi, Madam Lisa again. This is day three of the ongoing story of my real life sub and myself. I have changed only the names of those involved. I do not mention any locations by name, but I will assume some of you will be able to figure them out. Please read P1 and 2 as doing so will help you follow along. *** Recap. Yesterday I found my subs ex-girlfriend,...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

The Sexy Cuckold Couple Pt. 14

by cuckcpl4play on Sep 26, 2017
Fetish

Part 14 Pool I As we departed the room, I was utterly shocked that Master was in fact going to make us walk through the hotel as we were. He walked with his slut in front and I brought up the rear, but following closely in tow. I kept my head down but could feel the stares and after walking by a large group I heard the individuals bellowing at our predicame...

Reversals Ch. 15

by RachelClark on Mar 27, 2018
Fetish

Alterations Bright lights and a murmur of women's voices poured into the hall as Pamala opened the beautifully carved door to the treatment room. Julia smiled broadly in anticipation as they entered. It was going to happen here, in this room. She could hardly wait to see it, to watch him get injected, and to see the look in his eyes afterwards. Julia could...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...