Sissys First Blowjob Stories

318,519 results
Orientation
Length
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Infinite Scroll

My Wellhung (15"BBC) StepDad

by BibiBimbo on Apr 22, 2025

2 days after Bibi's 18th. birthday, the Sissys Mum brought her new NiggaMaster/Husbond-to-be with her home where Bibi was introduced to Rex, the WimpWuzz's next NiggaStepDad, who was 2m high, Wellbuild & Muschular weighing 125kg & Extremly Wellhung having 15" looong & 4½" thick Big Black NiggaCock.. He liked how the Bibi dressedUp as 'B...

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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...

und zur Sissy erzogen

by Yukyrei on Apr 29, 2025

In dieser Geschichte bist du ein 18-23 Jahre alter hetero Mann. Der in das Visier von Entführern geriet die junge Männer zu Sissys erziehen und diese werden für Kunden vermietet oder verkauft. Zur Sicherheit bekommt jeder ein Hypnose die verhindert das man etwas über die Organisation oder deren Taten verrät. Wer einmal von ihnen **** wurde ist auch nicht meh...

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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...

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...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

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...

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...