Sissy Training (1,780)

Viky & Mateo Private Show

Viky & Mateo Private Show

Flirt4Free 2 weeks ago

Emily & Stesha Private Show

46% 4K 2:00 / 4:08

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Amelia Sweety Private Show

Amelia Sweety Private Show

Flirt4Free 4 weeks ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 2 weeks ago

Emily & Stesha Private Show

49% 4K 2:00 / 7:00

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Cornelia Adams Private Show

68% HD 2:00 / 4:51

Cornelia Adams Private Show

Flirt4Free 1 month ago

Sissy Anal Training by Domina Fire

Sissy Anal Training by Domina Fire

xHamster 1 week ago

Spanish audio JOI - Watch out! For gamers who love anal, don't miss this perverse JOI.

Spanish audio JOI - Watch out! For gamers who love anal, don't miss this perverse JOI.

xHamster 2 weeks ago

Emily & Stesha Private Show

57% 4K 2:00 / 7:33

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Emily & Stesha Private Show

70% 4K 2:00 / 15:23

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Emily & Stesha Private Show

58% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Emily & Stesha Private Show

55% 4K 2:00 / 4:20

Emily & Stesha Private Show

Flirt4Free 3 weeks ago

$Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES$ 11:58

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

SexTVX 1 month ago

The Secret of My Body

55% 2:00 / 5:16

The Secret of My Body

Flirt4Free 3 weeks ago

Dominant Play And Sissy Training With Badninax

Dominant Play And Sissy Training With Badninax

DrTuber 3 weeks ago

Emily & Stesha Private Show

62% HD 2:00 / 4:53

Emily & Stesha Private Show

Flirt4Free 4 weeks ago

Mafe Flex & Sebastiaan Private Show

58% 4K 2:00 / 7:01

Mafe Flex & Sebastiaan Private Show

Flirt4Free 4 weeks ago

Sissy Maid Hole Training - Miss Zara Fox and Sandy

Sissy Maid Hole Training - Miss Zara Fox and Sandy

VivaTube 2 weeks ago

Humiliating him for having small cock

Humiliating him for having small cock

xHamster 3 weeks ago

Isadora Dunkan Private Show

Isadora Dunkan Private Show

Flirt4Free 3 weeks ago

Evening Discipline for the Sissy Maid

HD 0:10 / 19:34

Evening Discipline for the Sissy Maid

LoyalFans 3 weeks ago

Olya Sweetie Private Show

Olya Sweetie Private Show

Flirt4Free 3 weeks ago

POV Cuckold vol 30

POV Cuckold vol 30

xHamster 4 weeks ago

Intense Dildo Playtime for a Submissive Partner: Part Three

Intense Dildo Playtime for a Submissive Partner: Part Three

JuicyVid 1 week ago

Sissy Anal Training by Domina Fire

Sissy Anal Training by Domina Fire

FapHouse 1 week ago

Sissy Anal Training by Domina Fire

Sissy Anal Training by Domina Fire

xHamster 1 week ago

Emily & Stesha Private Show

56% 4K 2:00 / 13:27

Emily & Stesha Private Show

Flirt4Free 4 weeks ago

Amelia Sweety Private Show

Amelia Sweety Private Show

Flirt4Free 3 weeks ago

Rough Strapon Pegging for Sissy Slut - [FHD mp4] | Kiro Queen, JustALimeBoi | Femdom

66% 4K 0:27 / 11:19

Rough Strapon Pegging for Sissy Slut - [FHD mp4] | Kiro Queen, JustALimeBoi | Femdom

Clips4sale 2 weeks ago

Vollständige Körperkontrolle als Nutte

HD 0:10 / 10:05

Vollständige Körperkontrolle als Nutte

LoyalFans 1 week ago

Son Sent Away to Goddess Snow for Proper Sissy Training

Son Sent Away to Goddess Snow for Proper Sissy Training

HD21 2 weeks ago

Vicky's Femboy Sissy slut practices sucking and throat training on her dildo then gets spanked

HD 0:10 / 14:37

Vicky's Femboy Sissy slut practices sucking and throat training on her dildo then gets spanked

LoyalFans 2 weeks ago

Full doggy anal training

Full doggy anal training

LoyalFans 2 weeks ago

Torri Texass Private Show

4K 2:00 / 19:18

Torri Texass Private Show

Flirt4Free 2 weeks ago

ride dildoo:P - Part 2

ride dildoo:P - Part 2

Flirt4Free 1 week ago

Sweet & Daaniel Private Show

HD 2:00 / 12:14

Sweet & Daaniel Private Show

Flirt4Free 3 weeks ago

Scarlet Barbieri Private Show

Scarlet Barbieri Private Show

Flirt4Free 2 weeks ago

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

65% HD 0:39 / 12:35

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

FapHouse 2 weeks ago

First time anal for virgin sissy

First time anal for virgin sissy

xHamster 2 weeks ago

Two Baldur's Gate 3 players having sex

Two Baldur's Gate 3 players having sex

xHamster 2 weeks ago

Sweet & Daaniel Private Show

Sweet & Daaniel Private Show

Flirt4Free 3 weeks ago

Electra Joness Party on Jan 24, 2026 - Part 7

HD 2:00 / 2:24:00

Electra Joness Party on Jan 24, 2026 - Part 7

Flirt4Free 3 weeks ago

Angelica Swiss Party on Jan 21, 2026 - Part 2

64% 4K 2:00 / 4:00:00+

Angelica Swiss Party on Jan 21, 2026 - Part 2

Flirt4Free 3 weeks ago

Isadora Dunkan Private Show

Isadora Dunkan Private Show

Flirt4Free 2 weeks ago

Santa Cooper Private Show

4K 2:00 / 22:59

Santa Cooper Private Show

Flirt4Free 3 weeks ago

Stuffed Woman. the Hole Overflows as It Is Full to the Top

65% 0:39 / 11:41

Stuffed Woman. the Hole Overflows as It Is Full to the Top

FapHouse 2 weeks ago

Sissy feminization CEI goo drinking instructions - FemDom POV free porn episode

Sissy feminization CEI goo drinking instructions - FemDom POV free porn episode

SortPorn 3 weeks ago

Sissy Training Part 2 - Oral

64% 4K 1:01 / 38:08

Sissy Training Part 2 - Oral

FapHouse 3 weeks ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

xHamster 2 weeks ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

Lesbian8 2 weeks ago

Julia Milky Private Show

Julia Milky Private Show

Flirt4Free 2 weeks ago

Turning YOU into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Turning YOU into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Dafreeporn 3 weeks ago

Samantha Fiire Private Show

HD 2:00 / 1:08:28

Samantha Fiire Private Show

Flirt4Free 2 weeks ago

Amiee Cambridge - Stamina training for sissy sluts

Amiee Cambridge - Stamina training for sissy sluts

DrTuber 1 week ago

Detained and Fucked by Sinstress

HD 0:10 / 12:42

Detained and Fucked by Sinstress

LoyalFans 2 weeks ago

Electra Joness Private Show

Electra Joness Private Show

Flirt4Free 1 week ago

SISSY TRAINING FOR FAGGOT LOSERS

SISSY TRAINING FOR FAGGOT LOSERS

LoyalFans 1 week ago

Zara Rousse Private Show

4K 2:00 / 2:57:38

Zara Rousse Private Show

Flirt4Free 3 weeks ago

Training Gimp Part 3: Total Sensory Overload

66% HD 0:10 / 13:35

Training Gimp Part 3: Total Sensory Overload

LoyalFans 2 weeks ago

Santa Cooper Private Show

Santa Cooper Private Show

Flirt4Free 3 weeks ago

Thamara Angells Private Show

Thamara Angells Private Show

Flirt4Free 1 week ago

Electra Joness Private Show

63% HD 2:00 / 54:46

Electra Joness Private Show

Flirt4Free 3 weeks ago

Stepmommy Turns U into a Little Bunny Sissy Floozy - Penny Barber Taboo

Stepmommy Turns U into a Little Bunny Sissy Floozy - Penny Barber Taboo

FreePorn8 3 weeks ago

Zoey Evans Premiere Show

4K 2:00 / 11:28

Zoey Evans Premiere Show

Flirt4Free 2 weeks ago

Alessia Lacroix Private Show

Alessia Lacroix Private Show

Flirt4Free 1 week ago

Olive Wilson Private Show

Olive Wilson Private Show

Flirt4Free 2 weeks ago

fuck this hot nun - Part 2

66% HD 2:00 / 7:54

fuck this hot nun - Part 2

Flirt4Free 2 weeks ago

His Dirty Orgasm in Pervy Girl Strap (MP4)

His Dirty Orgasm in Pervy Girl Strap (MP4)

Clips4sale 1 week ago

Sissy useless clitty locked in chastity cage and use arsehole to get climax, sissygasm, sissyfication.

Sissy useless clitty locked in chastity cage and use arsehole to get climax, sissygasm, sissyfication.

BigTitsLust 2 weeks ago

Sweet & Daaniel Private Show

Sweet & Daaniel Private Show

Flirt4Free 1 month ago

Asian Dominatrix Pegging and Stretching Her Chastity Sissy

Asian Dominatrix Pegging and Stretching Her Chastity Sissy

xHamster 1 week ago

Stepmommy Turns YOU into a Little Bunny Sissy Wench - Penny Barber Taboo

Stepmommy Turns YOU into a Little Bunny Sissy Wench - Penny Barber Taboo

Dafreeporn 3 weeks ago

Yashira Lennis Party on Feb 7, 2026

4K 2:00 / 1:30:15

Yashira Lennis Party on Feb 7, 2026

Flirt4Free 1 week ago

ItalianLace - Sissy Training

ItalianLace - Sissy Training

VipTube 1 week ago

Emily & Stesha Private Show

4K 2:00 / 14:40

Emily & Stesha Private Show

Flirt4Free 1 week ago

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

xHamster 2 weeks ago

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

xHamster 2 weeks ago

Zoey Evans Premiere Show

Zoey Evans Premiere Show

Flirt4Free 2 weeks ago

Lilith Fenix Private Show

Lilith Fenix Private Show

Flirt4Free 3 weeks ago

Emmalee Jones Spanks Her Ass While She Gets Fucked

Emmalee Jones Spanks Her Ass While She Gets Fucked

Flirt4Free 1 week ago

Sissy Submissive Embarks on Prostate Training Journey with a Dominant Mistress

Sissy Submissive Embarks on Prostate Training Journey with a Dominant Mistress

JuicyVid 2 weeks ago

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

HD 0:39 / 12:35

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

FapHouse 2 weeks ago

Sweet & Daaniel Private Show

Sweet & Daaniel Private Show

Flirt4Free 6 days ago

Amber Sweeett Private Show

4K 2:00 / 39:22

Amber Sweeett Private Show

Flirt4Free 1 week ago

Viky & Mateo Private Show

67% HD 2:00 / 7:37

Viky & Mateo Private Show

Flirt4Free 2 weeks ago

Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training

Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training

xHamster 3 weeks ago

Anal Training, Learning

Anal Training, Learning

xHamster 4 weeks ago

lets have a hot time - Part 2

lets have a hot time - Part 2

Flirt4Free 2 weeks ago

Silver Fairy Party on Feb 2, 2026 - Part 2

4K 2:00 / 16:49

Silver Fairy Party on Feb 2, 2026 - Part 2

Flirt4Free 1 week ago

Humiliatrix Cuckold Instructions

Humiliatrix Cuckold Instructions

Pornvee 3 weeks ago

Emmalee Jones Private Show

55% 4K 2:00 / 5:41

Emmalee Jones Private Show

Flirt4Free 3 weeks ago

Zoey Evans Premiere Show

Zoey Evans Premiere Show

Flirt4Free 2 weeks ago

Slave Dog Training

Slave Dog Training

xHamster 2 weeks ago

in this group show ill strip tease, rub pussy, and use fuck machine until I cum. ;) - Part 2

in this group show ill strip tease, rub pussy, and use fuck machine until I cum. ;) - Part 2

Flirt4Free 2 weeks ago

Femboy Hami Sissy Training For Blowjob

Femboy Hami Sissy Training For Blowjob

TubeOn 3 weeks ago

“Encouraged” Bi Session ~ Double Domme, ending in CEI! 😋🥛

HD 0:10 / 11:56

“Encouraged” Bi Session ~ Double Domme, ending in CEI! 😋🥛

LoyalFans 1 week ago

Lizzy Woo's First Real Domme Session Gagging, Spit & Strict Cock-sucking Training with Goth Mistress Ruby

50% 1:01 / 9:40

Lizzy Woo's First Real Domme Session Gagging, Spit & Strict Cock-sucking Training with Goth Mistress Ruby

FapHouse 3 weeks ago

play time - Part 2

play time - Part 2

Flirt4Free 1 week ago

Hotty pegging serf Sasha Earth

Hotty pegging serf Sasha Earth

SortPorn 6 days ago

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

55% HD 0:10 / 2:40:24

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

LoyalFans 1 week ago

Slut School : Sissy Cei Training

Slut School : Sissy Cei Training

AbBDSM 2 weeks ago

Humiliation, belt-on and unfathomable fisting

Humiliation, belt-on and unfathomable fisting

Lesbian8 2 weeks ago

Princess turn this loser into her human chair

HD 0:10 / 11:58

Princess turn this loser into her human chair

LoyalFans 1 week ago

Femdom Chastity Training For Anal Whore

Femdom Chastity Training For Anal Whore

Ebony8 1 week ago

Lillie Peach Private Show

Lillie Peach Private Show

Flirt4Free 2 weeks ago

Strap On Fucking, Mistress Luna destroys a happy sissy slut

HD 0:10 / 19:54

Strap On Fucking, Mistress Luna destroys a happy sissy slut

LoyalFans 4 weeks ago

Take a Cue From My Cocksucker!

Take a Cue From My Cocksucker!

FapHouse 2 weeks ago

The White Room - Humiliation and Milking - Part 1

The White Room - Humiliation and Milking - Part 1

xHamster 1 week ago

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

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

xHamster 1 week ago

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

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

xHamster 2 weeks ago

Delivery Guy Becomes a Sissy

63% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 4 weeks ago

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

63% 0:39 / 8:35

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

FapHouse 5 days ago

Compilated of Make me Bi - Cuckolding - Chastity - BBC - Double Humiliations - Double Dominations

66% HD 1:00 / 38:25

Compilated of Make me Bi - Cuckolding - Chastity - BBC - Double Humiliations - Double Dominations

Clips4sale 2 weeks ago

Stuffed Woman. the Hole Overflows as It Is Full to the Top

Stuffed Woman. the Hole Overflows as It Is Full to the Top

FapHouse 2 weeks ago

Turning U into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Turning U into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Lesbian8 2 weeks ago

Julie and Liza's Latex Doll

65% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 6 days ago

Male slave gets assfucked by hot Anastasia Mistress

Male slave gets assfucked by hot Anastasia Mistress

xHamster 6 days ago

Femdom Pegging Gangbang

HD 1:01 / 12:36

Femdom Pegging Gangbang

FapHouse 3 days ago

Sissy Atonement

Sissy Atonement

FreePorn8 3 weeks ago

Turning YOU into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Turning YOU into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

PornFreeNow 2 weeks ago

1 2 3 4 5

1,780 results found

Narrow your search

sissy anal training

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

Parents

Newporno.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 Newporno.com. All rights reserved.