Sissy Chastity Training Stories

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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...

My Master was a Matchmaker

by justincbenedict on Aug 8, 2018
BDSM

SAID THE SPIDER TO THE FLY JULY 2018 STORIES THE MAN FROM MOUNT EIDERDOWN Cheverus Glass knelt before Specs, looking a little ill at ease out of his gray suit from Rogers Peet. Cheverus began stroking his penis slowly, biting his tongue as he did it. "Haven't touched this in a long time." Cheverus said, looking up at Specs, who was a little bored. Chever...

Letter from the Rocky Mountains

by justincbenedict on Oct 8, 2019
BDSM

Dear Shoeblossom Men call me a tease. I guess I come by it naturally. I love getting guys in trouble. I remember when I was about nineteen or twenty, getting to know my new stepbrother. Mom had married a fire-and-brimstone preacher type, he was rich, and I think later she got sick of him monitoring her TV time and then she took him for a lot of cash. But...

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...

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...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

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...

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...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

The Training of Sissy Paula Ch. 2

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress carolyn patted me on the head and said i did good. Then she sent me home. The chastity belt still on me, and the cucumber still in my bottom. I logged on line yet no e-mails from Mistress carolyn. It was 4 days before she sent me another e-mail. Hello my pet i bet you thought i had forgot about you. i replied with a yes Mistress i was be...