Sissys Pussy Sex Stories Stories

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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...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

Ultimate Sissy Weekend Ch. 01

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet littl...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

I Adore Crossdressers Pt. 04

by Ab9095 on Dec 3, 2018
Transgender & Crossdressers

Day 3 When she left last night she was a very happy girl. I have her clean up. Redo her makeup. Get her pretty. And then she has to leave like that. She makes me promise she will see me tomorrow. I actually have a hard time sleeping that night. She's running through my mind and I'm thinking about tomorrow. I send her a text in the morning telling her to...

Quarantine Queers Pt. 03

by secondsamuel on May 13, 2020
Transgender & Crossdressers

Author's Note: This is not to make light or minimize the clusterfuck that's going on right now. It's just my creative way of coping. If you like it, please let me know in the comments sections. * Our weird Quarantine rules had been in place for two weeks. A few times a day, Paul and I would switch our flatscreen over to Pornhub and suck each other dry. Ye...

Mrs. Branchbaum Fucks

by ILienBagby on Sep 17, 2017
Loving Wives

In the car, all was quiet. No one spoke. The chauffeur watched the road., both his hands on the wheel. Hedda Branchbaum, wife of Right wing broadcaster Swift Branchbaum for five months now, sat in the back seat of Branchbaum's Bentley Mulsanne. She was quiet, her back stiff, her stance upright, her eyes focused on the shaved neck of Moses Williams, the cha...

Elizabeth's Confession Pt. 04

by georgekaplan on Jun 4, 2019
Mature

I left the hotel around 5:30 am, having serviced with cunt & mouth three of the night boys. All paid me 100 euros. In financial terms, my first night as a whore had been excellent. My meeting with my very estranged husband less so. Why was I married to the only straight man who didn't want to fuck me? Still onwards as they say... On the down side I had not f...