sissy-training Porn (193)

Videos tagged sissy-training.

sissy-training Videos

SISSY Mindcontrol TRAINING - Sasha de Sade & Mistress Murmur 33:02

SISSY Mindcontrol TRAINING - Sasha de Sade & Mistress Murmur

Sasha de Sade 927.6K
My Sissy Girlfriend is a Cock Whore 6:23

My Sissy Girlfriend is a Cock Whore

777.7K
Making Mommy's Boy Bi - Mrs Mischief taboo fauxcest mom pov 8:10

Making Mommy's Boy Bi - Mrs Mischief taboo fauxcest mom pov

617.3K
Sissy Humiliation JOI 10:15

Sissy Humiliation JOI

Faith Rae 441.5K
Sissy Cuckold Cleans Bulls Cock 2:43

Sissy Cuckold Cleans Bulls Cock

291.3K
You'll Wear Panties Forever 11:47

You'll Wear Panties Forever

280.6K
Slut TGirl Sasha de Sade in Chastity Cock Cage 3:38

Slut TGirl Sasha de Sade in Chastity Cock Cage

Sasha de Sade 240.1K
Podcast Ep10: Sissy Bimbo Slut Confessions (Audio) 32:04

Podcast Ep10: Sissy Bimbo Slut Confessions (Audio)

213.8K
FIRST SISSY TRAINING ASSIGNMENT 4:55

FIRST SISSY TRAINING ASSIGNMENT

201.3K
Pegging his ass 0:57

Pegging his ass

174.4K
SISSY FAGGOT TRAINING VIDEO Erotic audio ONLY story to get your dick hard! 13:29

SISSY FAGGOT TRAINING VIDEO Erotic audio ONLY story to get your dick hard!

152.9K
SISSY TRAINING ASSIGNMENT 2 3:44

SISSY TRAINING ASSIGNMENT 2

129.9K
Sissy Training: one week in pink panties! 11:20

Sissy Training: one week in pink panties!

107.3K
Sissy Makeup Tutorial and Pheromone + Hormone Instruction 12:37

Sissy Makeup Tutorial and Pheromone + Hormone Instruction

103.9K
Full-Time Sissy Slut 8:12

Full-Time Sissy Slut

100.9K
Step Son Sissy Whore Training 15:05

Step Son Sissy Whore Training

97.9K
Sissy Sex Erotic Audio by Tara Smith. Sissy Bi Encouragement & Dirty Talk 7:21

Sissy Sex Erotic Audio by Tara Smith. Sissy Bi Encouragement & Dirty Talk

89.3K
Sissy Bimbo Sucks Strangers Dick Femdom Session 1:44

Sissy Bimbo Sucks Strangers Dick Femdom Session

85.9K
Mistress Makes You a Sissy 9:36

Mistress Makes You a Sissy

73.5K
Amateur Cumshot after 3hrs of edging - Sasha de Sade British TS 3:46

Amateur Cumshot after 3hrs of edging - Sasha de Sade British TS

Sasha de Sade 65.1K
Sissy Training Mindfuck Mesmerise Femdom 18:27

Sissy Training Mindfuck Mesmerise Femdom

62.7K
Gay Faggot for BBC - CUM EATING INSTRUCTIONS - SISSY TRAINING (PREVIEW) 1:29

Gay Faggot for BBC - CUM EATING INSTRUCTIONS - SISSY TRAINING (PREVIEW)

56.0K
Transforming you into My sissy prostitute 0:26

Transforming you into My sissy prostitute

Ezada Sinn 56.0K
Lesbian Femdom Has A Bigger Dick Than You 4:15

Lesbian Femdom Has A Bigger Dick Than You

53.0K
Fucking Myself & Riding HUGE Dildo For My Mistress - Part 2 3:00

Fucking Myself & Riding HUGE Dildo For My Mistress - Part 2

53.0K
GF encourages you to be her sissy Quickie 2:57

GF encourages you to be her sissy Quickie

51.7K
Piss Drinking and Feminization Lipstick 6:45

Piss Drinking and Feminization Lipstick

51.1K
Leya Falcon Extreme Cock and Ball Torture inside The Hurt Room 4:26

Leya Falcon Extreme Cock and Ball Torture inside The Hurt Room

Leya Falcon 45.7K
Watch me ride REAL COCK BBC ONLY 13:31

Watch me ride REAL COCK BBC ONLY

45.5K
GF helps you transform into a woman Quickie 3:01

GF helps you transform into a woman Quickie

44.9K
Ruined orgasm marathon 0:53

Ruined orgasm marathon

Ezada Sinn 38.7K
Feminization and Sissy Training for Smooth Soft Skin 9:41

Feminization and Sissy Training for Smooth Soft Skin

32.7K
FemDom Mindcontrol - Black Boots Black Dress Stockings 5:32

FemDom Mindcontrol - Black Boots Black Dress Stockings

31.7K
You Need Cock To Cum. Tara Smith Smoking Narrative Male Bisexual Sexy Tease 10:13

You Need Cock To Cum. Tara Smith Smoking Narrative Male Bisexual Sexy Tease

31.6K
Sissy slut eats cums while fucking ass with huge bbc dildo 3:23

Sissy slut eats cums while fucking ass with huge bbc dildo

26.4K
you Know you Crave Huge Black Cock & Worship Heels sissy 9:09

you Know you Crave Huge Black Cock & Worship Heels sissy

21.5K
Leya Falcon Sissy Training a slave inside The Hurt Room 3:02

Leya Falcon Sissy Training a slave inside The Hurt Room

Leya Falcon 21.3K
Sissy: A Slut Documentary 1:11

Sissy: A Slut Documentary

21.2K
Sissy trap tranny anal training cum. 16:15

Sissy trap tranny anal training cum.

20.5K
Sissy's Hopeless Addiction - Latex Femdom POV teaser ft. Star Nine 0:47

Sissy's Hopeless Addiction - Latex Femdom POV teaser ft. Star Nine

Star Nine 19.6K
The banana trigger 0:49

The banana trigger

Ezada Sinn 19.6K
Sissy Training Instructions for Fuckable Feet like Mine! 13:06

Sissy Training Instructions for Fuckable Feet like Mine!

19.0K
Be My Barbie Bimbo - Teaser Clip 2:33

Be My Barbie Bimbo - Teaser Clip

Faith Rae 18.6K
Femdom Goddess Dresses You Up & Shows You Off Like a Sissy Slut 2:13

Femdom Goddess Dresses You Up & Shows You Off Like a Sissy Slut

Amber Haze 17.2K
Sissy getting Ready for the Streets 0:46

Sissy getting Ready for the Streets

14.7K
Bigger Blacker BBC Sissy Training Verbal Humilation 0:22

Bigger Blacker BBC Sissy Training Verbal Humilation

14.3K
Sissy Feminization Encouragement POV 11:11

Sissy Feminization Encouragement POV

12.3K
sissy training from naked male to sexy female ready to get fucked 2:52

sissy training from naked male to sexy female ready to get fucked

12.1K
sissy humiliation tasks made for mistress 9:01

sissy humiliation tasks made for mistress

11.5K
Domination Instruction with Mistress Allura 7:29

Domination Instruction with Mistress Allura

Allura Skye 10.8K
Sissy Deborah have her first Sissygasm 3:37

Sissy Deborah have her first Sissygasm

10.6K
FemDom Goddess Dahlia trains u 2 be a cocksucking SISSY STREETWALKING WHORE 6:07

FemDom Goddess Dahlia trains u 2 be a cocksucking SISSY STREETWALKING WHORE

10.0K
Put your lipstick on for me slut 10:54

Put your lipstick on for me slut

9.4K
Cucky Cock Fluffer Short Story - Audio Only 2:30

Cucky Cock Fluffer Short Story - Audio Only

9.4K
deep anal training of a young Femboy big dildo in his ass ( sissy boy) 3:54

deep anal training of a young Femboy big dildo in his ass ( sissy boy)

8.7K
Perversions Ep1: Sissy Chasti with Janet Deluna 37:27

Perversions Ep1: Sissy Chasti with Janet Deluna

8.6K
Dominated By The Submissive Woman 2 - Ashley Lane Sissy Training TRAILER 0:50

Dominated By The Submissive Woman 2 - Ashley Lane Sissy Training TRAILER

Ashley Lane 8.6K
Mistress Kennya: Sissy training preview 0:33

Mistress Kennya: Sissy training preview

8.3K
Sissy Bitch Face Sitting Session Femdom 2:37

Sissy Bitch Face Sitting Session Femdom

7.7K
...And You Thought My Last Dildo Was Big! 5:01

...And You Thought My Last Dildo Was Big!

7.6K

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About sissy-training

The sissy-training tag groups niche clips that share a specific theme or keyword. Unlike broad category hubs, tag pages target long-tail searches where viewers already know the exact flavor they want. This listing includes 193 tagged videos ranked by views, with related tags and categories for deeper discovery. Trending picks within the tag highlight what other users watch most, while pagination keeps older uploads accessible without bloating crawl paths.

Frequently Asked Questions

What does the sissy-training tag include?

Videos tagged sissy-training share a common theme or keyword. This page lists 193 matching clips sorted by popularity.

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Categories cover broad browsing intent (e.g. amateur, POV). Tags are narrower labels that describe specific themes within those categories.