Smooth Sissy Stories

1,000 results
Orientation
Length
Category
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Infinite Scroll

Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...

Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

Finally Found Her Ch. 02

by hyperpress on Aug 18, 2017
Fetish

Switching from "you" to "she" for effect. She moved from the vanity chair to the bed. I've covered the bed with pillows and the room is lit with candles. "You're such a good little girl, now go get us a bottle of wine," she is lovely on the bed. I'm standing at the bedside and your mouth is irresistible and I bend at the waste to kiss you. Softly we kiss a...

Mistress Marisa's Estate Pt. 11

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** The matron sits at the front of the room, gorgeous and tailored perfectly. She's wearing a tight short black dress and nee...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

How I went from Domme to Slut Ch. 03

by Ms_Allison on Mar 7, 2018
BDSM

Another night of not knowing and torment was coming, this time I would have company, amber would be with me. This would be new. Ms. Linda had contacted me during the day via text. Her instructions were quite simple, amber and I were to bring a selection of slutty lingerie for her to choose from, our highest heels, and not bring any attention to ourselves as...

Bukakke Sissy/Angel

by hyperpress on Sep 14, 2017
Fetish

He's wearing his favorite outfit. A nylon/spandex blended thong that encased his fullness, shaved and smooth in a delightful caress. A bustier girdle with four straps (he wanted six but the cost was exponentially increased for those two extra straps), and wolford thigh high stockings, his legs and bottom were completely shaved...he was delighted with how fem...

Sorry Sissy You Lose Pt. 02

by LittleDickSissy on Jan 22, 2019
Fetish

Mistress enjoyed watching herself primp in the mirror. Music playing in the background, a glass of alcohol to sip from, and the knowledge she was going out on a date with George - the older gentleman she had been fantasizing about. As she slid her smooth legs into a pair of crotchless hose purchased by her sissy slave she looked at her trimmed bush. The si...

My sissy boss.

by mally01 on Apr 22, 2025

Craig was in his office at Lingerie International watching the wall clock his left drifting under his shirt stroking his soft hairless skin. He was waiting for five thirty knock-off time to come. His secretary Charlotte came in and asked if he needed anything else, and he gruffly replied that she could leave for the day. After he had witnessed Chantelle get...

Alex Taiman Sissy

by sissysub34 on Apr 29, 2025

Alex had always been a little different from most other kids for starters instead of growing in muscles or body hair growing on him he remained smooth then his preference of clothes were all more Unisex than others thought as such most didn't always get along with him which lead to him getting bullied were it not for his family he wouldn't have known what to...