Sissy Training Tube (154,326)

Dominatrix Pegging Chastity

64% 0:39 / 5:09

Dominatrix Pegging Chastity

FapHouse 1 month ago

Ruby Reeds Private Show

4K 2:00 / 19:51

Ruby Reeds Private Show

Camster 1 week ago

Viky & Mateo Private Show

59% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 8 months ago

Training Your Useless Sissy Clit in Chastity

Training Your Useless Sissy Clit in Chastity

Itsrealamateurs 3 weeks ago

First Anal Experience-wmv

53% HD 1:01 / 9:15

First Anal Experience-wmv

FapHouse 2 months ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 2 months ago

He's been asking for so long. I saw for the first time what a male anal orgasm is.

He's been asking for so long. I saw for the first time what a male anal orgasm is.

XHamster 4 years ago

Strict Group Anal Training Under Supervision

68% HD 0:39 / 14:39

Strict Group Anal Training Under Supervision

FapHouse 1 month ago

Isadora Dunkan Private Show

4K 2:00 / 32:58

Isadora Dunkan Private Show

Flirt4Free 1 week ago

Going sissy is the only way to please Me

HD 0:15 / 14:02

Going sissy is the only way to please Me

IWantClips 3 months ago

Elizabeth Whiler Private Show

56% HD 2:00 / 9:53

Elizabeth Whiler Private Show

Camster 3 years ago

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

57% 1:01 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 2 years ago

Slut training (SD Video)

62% 0:16 / 18:08

Slut training (SD Video)

Clips4sale 2 years ago

Amber Fletcher Private Show

62% HD 2:00 / 5:11

Amber Fletcher Private Show

Camster 2 years ago

Kinky Carmen In Sissy Bitch Training By

Kinky Carmen In Sissy Bitch Training By

AbXXX 4 years ago

Ariane Elisse Party on Sep 20, 2026 - Part 5

HD 2:00 / 35:18

Ariane Elisse Party on Sep 20, 2026 - Part 5

Flirt4Free 4 days ago

Slavena puts the ANACONDA into Lusinta`s pussy-hole

HD 0:11 / 23:45

Slavena puts the ANACONDA into Lusinta`s pussy-hole

Clips4sale 4 years ago

You Will Beg Me To Link You To This Video. Big Compilation.

You Will Beg Me To Link You To This Video. Big Compilation.

XHamster 3 years ago

Oh Yep - Cum Coach

Oh Yep - Cum Coach

Amateur8 4 years ago

Carolina Betancur Private Show

HD 2:00 / 29:17

Carolina Betancur Private Show

Flirt4Free 4 weeks ago

Femdom Pegging Latex Sissy by Dominafire

Femdom Pegging Latex Sissy by Dominafire

XHamster 2 years ago

Glossed Beyond Your Reach: Latex Pool Party Edition

Premium HD 7:26

Glossed Beyond Your Reach: Latex Pool Party Edition

Clips4sale 1 week ago

Blonde Sex Slave Inseminated in Steel Shackles

Blonde Sex Slave Inseminated in Steel Shackles

XHamster 3 weeks ago

Electra Joness Party on Apr 13, 2026 - Part 3

56% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 5 months ago

Sissy Slut Session

HD 0:10 / 10:16

Sissy Slut Session

LoyalFans 3 years ago

Intro To Sissification 4 - Anal Play

Intro To Sissification 4 - Anal Play

Clips4sale 2 years ago

Mind Fuck And Sissy Throat Training

HD 0:30 / 15:23

Mind Fuck And Sissy Throat Training

Clips4sale 1 year ago

Your New Life as My Free Use Sissy

45% HD 0:39 / 16:13

Your New Life as My Free Use Sissy

FapHouse 7 months ago

Vilu Vidish Makes a Boy Into a Girl to Peg Him

Vilu Vidish Makes a Boy Into a Girl to Peg Him

XHamster 4 months ago

My cum eating chastity slave gets to clean my feet

My cum eating chastity slave gets to clean my feet

XHamster 1 year ago

The Ultimate Sissy Training by Miss Brat

The Ultimate Sissy Training by Miss Brat

PornoXO 10 years ago

Cute Sissy Cumming Hands Free

Cute Sissy Cumming Hands Free

XHamster 2 years ago

Humbled sissy gets a 72 stroke caning from expert caner Nikki Whiplash WL1779

Humbled sissy gets a 72 stroke caning from expert caner Nikki Whiplash WL1779

Clips4sale 1 year ago

Sissy Clit Versus Big Black Cock

Sissy Clit Versus Big Black Cock

XHamster 2 weeks ago

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

72% HD 1:01 / 5:45

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

FapHouse 4 months ago

Big-dicked sissy takes it up the ass and swallows his own cum

Big-dicked sissy takes it up the ass and swallows his own cum

XXXShake 3 years ago

Elizabeth Whiler Private Show

57% HD 2:00 / 6:03

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

Lesbian8 1 year ago

Betty Sandra Private Show

60% HD 2:00 / 4:25

Betty Sandra Private Show

Flirt4Free 3 years ago

Deep Strap-on Lesson for a Sissy Slut’s Ass

Deep Strap-on Lesson for a Sissy Slut’s Ass

FapHouse 1 week ago

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

64% HD 0:39 / 47:50

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

FapHouse 3 weeks ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 2 months ago

Jhanne Cherry Private Show

60% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

We Love Spreading and Playing with Our Big Asses.

We Love Spreading and Playing with Our Big Asses.

XHamster 4 months ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 year ago

Baby in paradise part 1

63% HD 0:39 / 9:01

Baby in paradise part 1

FapHouse 4 years ago

Sissy Bitch Pegging Compilation. Femdom Chastity

Sissy Bitch Pegging Compilation. Femdom Chastity

BigTitsLust 2 years ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Take It Like a Slutty Whore! - Femdom POV with Strap-on, Slut Training, Masturbation with Miss Adrastea

53% HD 0:39 / 15:49

Take It Like a Slutty Whore! - Femdom POV with Strap-on, Slut Training, Masturbation with Miss Adrastea

FapHouse 2 weeks ago

Sissy Training- Blowjob CEI HYP

Sissy Training- Blowjob CEI HYP

Eporner 4 months ago

Strap-on fucking and latex sissy training: a day in the life of a Matriarch Ezada Sinn’s sissy husband

Premium HD 15:10

Strap-on fucking and latex sissy training: a day in the life of a Matriarch Ezada Sinn’s sissy husband

Clips4sale 2 months ago

Femdom: Sissy feminization training!

Femdom: Sissy feminization training!

Itsrealamateurs 2 months ago

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

XHamster 2 years ago

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 year ago

Lost Another Bet?

Lost Another Bet?

LoyalFans 2 years ago

Sissy Date Night

59% 1:01 / 19:30

Sissy Date Night

FapHouse 2 months ago

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

67% HD 1:01 / 47:50

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

FapHouse 3 weeks ago

Sweet & Daaniel Private Show

64% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 3 months ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

Sissy dress : Mistress Lily Dupont dresses his sissy

HD 0:25 / 16:29

Sissy dress : Mistress Lily Dupont dresses his sissy

Clips4sale 1 week ago

Sissy-Training – Daran solltest du dich gewöhnen!

Sissy-Training – Daran solltest du dich gewöhnen!

LoyalFans 1 month ago

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

XHamster 6 months ago

Sunday Humiliation for Sissy husband Full

Sunday Humiliation for Sissy husband Full

XHamster 1 year ago

Bi Cuckold Transformation

Bi Cuckold Transformation

Clips4sale 1 year ago

Sabrina Velvet Private Show

60% 4K 2:00 / 12:52

Sabrina Velvet Private Show

Flirt4Free 5 months ago

sissy joyce - goddess annie i love their helpless porn video

sissy joyce - goddess annie i love their helpless porn video

BDSMShip 1 year ago

Dressing up Sissy

Dressing up Sissy

XVideos 1 year ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

58% 0:39 / 25:09

JOI Echo in Latex with My Big Black Strapon - Luna Doll

FapHouse 11 months ago

Sissy & cuckold training

52% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 years ago

Cruel BBW Goddess Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piss Drinking!

Cruel BBW Goddess Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piss Drinking!

XHamster 4 months ago

Adara Smith & Elver Rodriguez Private Show

64% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Camster 3 years ago

Jen Holly Private Show

53% HD 2:00 / 8:35

Jen Holly Private Show

Flirt4Free 1 year ago

Jen Holly Private Show

67% HD 2:00 / 7:50

Jen Holly Private Show

Camster 1 year ago

April Benson Private Show

57% HD 2:00 / 8:59

April Benson Private Show

Flirt4Free 2 years ago

Reven Mayers Private Show

64% HD 2:00 / 4:09

Reven Mayers Private Show

Flirt4Free 3 weeks ago

Viuda Nagra Private Show

59% HD 2:00 / 29:45

Viuda Nagra Private Show

Flirt4Free 3 years ago

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Yesvids 2 months ago

Isadora Dunkan Private Show

4K 2:00 / 16:35

Isadora Dunkan Private Show

Camster 1 month ago

Leather Cum Show

HD 2:00 / 27:41

Leather Cum Show

Camster 8 years ago

Viky & Mateo Private Show

51% HD 2:00 / 4:35

Viky & Mateo Private Show

Flirt4Free 8 months ago

Sissy Panty Slut Sph JOI

Sissy Panty Slut Sph JOI

XHamster 4 months ago

Tita Madurita Private Show

64% HD 2:00 / 4:20

Tita Madurita Private Show

Camster 3 years ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

XHamster 2 years ago

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Amateur8 10 months ago

From Business Man To Serving Girl (4KUHD MP4)

60% HD 0:30 / 14:13

From Business Man To Serving Girl (4KUHD MP4)

Clips4sale 4 years ago

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

XHamster 2 years ago

Femdom POV Sissy Training Pleasure Him

46% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 5 months ago

WELCOME YOUR BLACK MASTER - BBC CUCOLDING - YOU GET A BLACK FEET IN YOUR MOUTH AND A SUPER SIZED COCK IN YOUR ASS - THE DIRTIEST SISSY SLUT TRAINING (720p)

49% HD 0:11 / 14:20

WELCOME YOUR BLACK MASTER - BBC CUCOLDING - YOU GET A BLACK FEET IN YOUR MOUTH AND A SUPER SIZED COCK IN YOUR ASS - THE DIRTIEST SISSY SLUT TRAINING (720p)

Clips4sale 5 years ago

Sissy Slut School: Sissy Whore Trained to suck men's cocks and Take Deep Pegging Head Mistress Stellina Obscura

Sissy Slut School: Sissy Whore Trained to suck men's cocks and Take Deep Pegging Head Mistress Stellina Obscura

StiefMutter 1 month ago

Jhanne Cherry Private Show

54% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Elizabeth Whiler Private Show

52% HD 2:00 / 4:23

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

XHamster 1 year ago

Halloween Custome, Pennywise

60% HD 2:00 / 7:33

Halloween Custome, Pennywise

Flirt4Free 3 years ago

Post-Op Feminization Sissy Claimed By Femdom Ding-dong

Post-Op Feminization Sissy Claimed By Femdom Ding-dong

Ebony8 1 month ago

Jen Holly Private Show

65% HD 2:00 / 7:30

Jen Holly Private Show

Camster 1 year ago

Jhanne Cherry Private Show

52% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Anorganix Private Show

HD 2:00 / 17:36

Anorganix Private Show

Flirt4Free 8 years ago

Viky & Mateo Private Show

56% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 8 months ago

Jhanne Cherry Private Show

52% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Camster 1 year ago

Femdom Republic Sissy Training And Feminisation a Feminine

Femdom Republic Sissy Training And Feminisation a Feminine

DrTuber 1 month ago

Leena Sky Private Show

HD 2:00 / 11:36

Leena Sky Private Show

Flirt4Free 3 years ago

Jhanne Cherry Private Show

64% 4K 2:00 / 4:55

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Sienna Starlight Party on Sep 15, 2026 - Part 2

4K 2:00 / 50:08

Sienna Starlight Party on Sep 15, 2026 - Part 2

Flirt4Free 1 week ago

Viky & Mateo Private Show

66% HD 2:00 / 4:46

Viky & Mateo Private Show

Camster 8 months ago

Emily & Stesha Private Show

62% 4K 2:00 / 4:08

Emily & Stesha Private Show

Camster 7 months ago

Top 10 Pegging Cumshots Vol.1

Top 10 Pegging Cumshots Vol.1

XHamster 11 months ago

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Lesbian8 1 month ago

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

XHamster 1 year ago

Brittney & Elvis Private Show

63% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 3 years ago

Training my wife to anal. First anal stretching. Enema. Ep 24943

Training my wife to anal. First anal stretching. Enema. Ep 24943

XHamster 7 months ago

Chastity tutorial - how to wear a chastity cage - part 1

Chastity tutorial - how to wear a chastity cage - part 1

XHamster 7 months ago

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

57% 4K 0:25 / 16:22

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

Clips4sale 11 months ago

Sissy chastity training for lifetime slavery

61% 0:28 / 5:40

Sissy chastity training for lifetime slavery

Clips4sale 4 years ago

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

KAMS 1 year ago

Punished Sissy Husband (FULL): Femdom Wife Punishes Sissy Whore with Pegging & Fisting with Stellina Obscura in Latex

HD 0:25 / 49:13

Punished Sissy Husband (FULL): Femdom Wife Punishes Sissy Whore with Pegging & Fisting with Stellina Obscura in Latex

Clips4sale 4 weeks ago

Evil big beautiful woman Domina Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

Evil big beautiful woman Domina Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

SortPorn 2 months ago

Viky & Mateo Private Show

60% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 8 months ago

Jen Holly Private Show

61% HD 2:00 / 8:35

Jen Holly Private Show

Camster 1 year ago

1 2 3 4 5

154,326 results found

Related searches

Narrow your search

sissy anal training

Categories Pornstars

Parents

Tubeporn.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Tubeporn.com. All rights reserved.

© 2026 Tubeporn.com. All rights reserved.