kink + sissy-training Porn (73)

Watch 73 videos tagged kink and sissy-training. Curated compound tag listings sorted by popularity.

kink + 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
Sissy Humiliation JOI 10:15

Sissy Humiliation JOI

Faith Rae 441.5K
You'll Wear Panties Forever 11:47

You'll Wear Panties Forever

280.6K
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
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
Full-Time Sissy Slut 8:12

Full-Time Sissy Slut

100.9K
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
Sissy Training Mindfuck Mesmerise Femdom 18:27

Sissy Training Mindfuck Mesmerise Femdom

62.7K
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
GF encourages you to be her sissy Quickie 2:57

GF encourages you to be her sissy Quickie

51.7K
GF helps you transform into a woman Quickie 3:01

GF helps you transform into a woman Quickie

44.9K
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: A Slut Documentary 1:11

Sissy: A Slut Documentary

21.2K
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
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 17.3K
Sissy Feminization Encouragement POV 11:11

Sissy Feminization Encouragement POV

12.3K
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
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
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
Cum Cube - Sissy Training CEI CBT Chastity - TRAILER 1:04

Cum Cube - Sissy Training CEI CBT Chastity - TRAILER

Star Nine 7.6K
Sissy slut wearing latex pounded hard by fucking machine. 2:17

Sissy slut wearing latex pounded hard by fucking machine.

6.8K
Cum Cube 2 - CEI Chastity Sissy Training Star Nine Teaser 0:51

Cum Cube 2 - CEI Chastity Sissy Training Star Nine Teaser

Star Nine 6.0K
Be My sissy Valentine 1:12

Be My sissy Valentine

Ezada Sinn 5.6K
Preview of Showing Sissy how to Cum from Anal 1:18

Preview of Showing Sissy how to Cum from Anal

5.5K
Extreme Anal Gaping Sissy Bimbo Brandynette First Latex Outfit 19:51

Extreme Anal Gaping Sissy Bimbo Brandynette First Latex Outfit

Brandynette 4.9K
Angel Black the sissy maid plays with her blow up girlfriend 1:37

Angel Black the sissy maid plays with her blow up girlfriend

Angel Scarlett Black 4.2K
Sissy's Electric Release - Chastity Orgasm Control Femdom POV Trailer 0:38

Sissy's Electric Release - Chastity Orgasm Control Femdom POV Trailer

Star Nine 4.0K
Her 43cm Black Deep Anal insertion - Pink Latex Bimbo Brandynette 27:23

Her 43cm Black Deep Anal insertion - Pink Latex Bimbo Brandynette

Brandynette 3.7K
Sissy's Electric Training - Star Nine Femdom POV Electric Play Trailer 0:54

Sissy's Electric Training - Star Nine Femdom POV Electric Play Trailer

Star Nine 3.3K
Chinky Chelsie Under Mindcontrol 3:23

Chinky Chelsie Under Mindcontrol

3.2K
Sissy in chastity training asshole with big dildo 1:58

Sissy in chastity training asshole with big dildo

2.8K
Escape - POV Strap-On Sissy Training Star Nine TRAILER 0:35

Escape - POV Strap-On Sissy Training Star Nine TRAILER

Star Nine 2.5K
Willenloses Sissy Spielzeug Strapon Blowjob Assfuck Chastity Training 7:25

Willenloses Sissy Spielzeug Strapon Blowjob Assfuck Chastity Training

2.2K
CEI Sissy Training - Femdom POV Star Nine TRAILER 0:39

CEI Sissy Training - Femdom POV Star Nine TRAILER

Star Nine 2.1K
Emotional Freeing Technique For Sissies 4:29

Emotional Freeing Technique For Sissies

2.1K
Making you sniff our coworkers shoes TEASER 2:07

Making you sniff our coworkers shoes TEASER

1.6K
tgirl's throat training week: day 1 1:25

tgirl's throat training week: day 1

997
30 Year Old Sissy Virgin 8:51

30 Year Old Sissy Virgin

Ceara Lynch 930
Close up sissy sloppy anal pounding fuck machine 1:12

Close up sissy sloppy anal pounding fuck machine

891
Pimping Out Sissy Whores 8:04

Pimping Out Sissy Whores

677
Sissy Searching for Daddy 2:22

Sissy Searching for Daddy

602
Sissy Panty Boy Quick Cumshot 2:06

Sissy Panty Boy Quick Cumshot

596
D 11:30

D

Mandy Flores 347
Beginning sissy faggot jerking! 0:58

Beginning sissy faggot jerking!

302
Ride BBC Dildo for Goddess 9/5/18 1:10

Ride BBC Dildo for Goddess 9/5/18

278
Ride BBC Dildo for Goddess 9/5/18 my big one 2:13

Ride BBC Dildo for Goddess 9/5/18 my big one

268

About kink + sissy-training

This page combines the tags kink and sissy-training to target a specific long-tail search intent. Instead of browsing each tag separately, you get 73 videos that match all selected themes. Listings are ranked by views with pagination rules that keep deeper pages out of the index. Use related single-tag hubs below to explore broader or adjacent niches.

Frequently Asked Questions

How many kink + sissy-training videos are listed?

There are currently 73 videos tagged with all of: kink, sissy-training.

Why combine tags like kink + sissy-training?

Compound tags help narrow results when a single tag is too broad. This page only appears when enough videos match.