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Sissy Training (264,191)

Spit drinking and cock sucking, best treats for a sissy slut! starring Mistress Luna

65% HD 0:40 / 15:10

Spit drinking and cock sucking, best treats for a sissy slut! starring Mistress Luna

Clips4sale 2 weeks ago

becomingfemme - natty is a beautiful blonde sissy

becomingfemme - natty is a beautiful blonde sissy

TransDoe 2 years ago

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

XHamster 1 month ago

Self Facial Cumshot spunking from super-steamy sissy

Self Facial Cumshot spunking from super-steamy sissy

TrannyGem 4 years ago

Valentin Durand Private Show

72% HD 2:00 / 18:40

Valentin Durand Private Show

Flirt4Free 6 months ago

Doll's trainning to throatfuck with silicone mask

Doll's trainning to throatfuck with silicone mask

XHamster 2 days ago

Lady Lads gone nasty for jizz and meatpipe

Lady Lads gone nasty for jizz and meatpipe

Transvids.tv 1 year ago

Bigdaddy8inchz Trains a Mesh Sissy

Bigdaddy8inchz Trains a Mesh Sissy

FapHouse 1 week ago

Switching to even more negative cell

Switching to even more negative cell

Gayhub 11 months ago

Anal Gape Training in chastity cage

Anal Gape Training in chastity cage

XHamster 9 months ago

Ebony TS slut assfuck her before deepthroating cock

Ebony TS slut assfuck her before deepthroating cock

Some.Porn 1 year ago

Sissy Hope teasing in pantihose

Sissy Hope teasing in pantihose

XHamster 2 years ago

Putting Big Toys in a Sissy Butt Hole - Regular Anal Traning for Tiffany with Mistress J

Putting Big Toys in a Sissy Butt Hole - Regular Anal Traning for Tiffany with Mistress J

XHamster 1 year ago

Archie Blossom Private Show

61% HD 2:00 / 5:06

Archie Blossom Private Show

Flirt4Free 6 months ago

Sissified by Step-Mommy

65% HD 0:15 / 13:28

Sissified by Step-Mommy

IWantClips 3 months ago

CHECKING PEGGING SISSY HOLES

Premium HD 11:05

CHECKING PEGGING SISSY HOLES

Sheer 1 year ago

Feet Foot Sucking, Cuming and Play

51% 4K 2:00 / 30:38

Feet Foot Sucking, Cuming and Play

Flirt4Free 7 months ago

Katryn Anal Training N.1

Katryn Anal Training N.1

XHamster 4 months ago

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53% HD 2:00 / 9:53

hot show, blowjobs and fucking

Flirt4Free 2 years ago

Sophia Loreen Party on Aug 22, 2026 - Part 3

64% 4K 2:00 / 1:33:22

Sophia Loreen Party on Aug 22, 2026 - Part 3

Flirt4Free 1 month ago

Kassidy Moonshine Private Show

HD 2:00 / 20:00

Kassidy Moonshine Private Show

Flirt4Free 11 years ago

Naked and Burning

42% HD 2:00 / 5:21

Naked and Burning

Flirt4Free 7 years ago

Sissy Challenge

Sissy Challenge

IWantClips 3 months ago

korean killer femboy three-way (utter movie on fansly)

korean killer femboy three-way (utter movie on fansly)

Gayhub 1 year ago

Sissy Strip Tease

65% 4K 0:25 / 9:31

Sissy Strip Tease

Clips4sale 2 weeks ago

Stuard & Briann & Stivens Private Show

63% HD 2:00 / 4:15

Stuard & Briann & Stivens Private Show

Flirt4Free 3 years ago

Sissy Slave Training

HD 1:01 / 11:53

Sissy Slave Training

FapHouse 2 weeks ago

Femboy Pet in Warmth Played and Smashed

Femboy Pet in Warmth Played and Smashed

Gayhub 1 year ago

A Show in My Native Language :)

A Show in My Native Language :)

Flirt4Free 7 months ago

How to make a Lovely Servant Sissy 8: Grad Asst. Teaching another Sissy

How to make a Lovely Servant Sissy 8: Grad Asst. Teaching another Sissy

TrannyGem 6 years ago

DP Fetish Fun

66% HD 0:39 / 13:12

FapHouse 6 years ago

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

48% 1:01 / 5:38

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

FapHouse 7 months ago

Pushing Out My Wet Rose and Fisting It

Pushing Out My Wet Rose and Fisting It

FapHouse 3 weeks ago

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

XHamster 8 months ago

Rubber sissy transformation fantasy part2

Rubber sissy transformation fantasy part2

FapHouse 7 years ago

Sissygasm Reward

55% HD 0:10 / 12:47

Sissygasm Reward

LoyalFans 1 week ago

Brayan Andrade Private Show

66% HD 2:00 / 8:02

Brayan Andrade Private Show

Flirt4Free 11 months ago

Nacho Vidal Private Show

54% HD 2:00 / 12:37

Nacho Vidal Private Show

Flirt4Free 1 year ago

Bad Dragon Pounding and Gaping - original early web camera show by Mistresse Mercer

Bad Dragon Pounding and Gaping - original early web camera show by Mistresse Mercer

Lesbian8 4 months ago

Krys Brown Private Show

59% HD 2:00 / 5:14

Krys Brown Private Show

Flirt4Free 7 years ago

Turning My Boyfriend Into A Bi Sissy Cuck

55% 0:30 / 17:28

Turning My Boyfriend Into A Bi Sissy Cuck

Clips4sale 1 week ago

Alpha male turned sissy by Petra Hunter!

Alpha male turned sissy by Petra Hunter!

Fetishpapa 1 month ago

Butt Slut Halloween Makeup

HD 1:01 / 11:45

Butt Slut Halloween Makeup

FapHouse 1 day ago

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Eporner 3 years ago

Emily & Stesha Private Show

64% 4K 2:00 / 13:27

Emily & Stesha Private Show

Flirt4Free 8 months ago

Anal training part 4 of 5

Anal training part 4 of 5

XHamster 1 week ago

Two Powerful Women, One Helpless Sub- Brandi Mae, Taperedphysique and CJ

Premium HD 14:21

Two Powerful Women, One Helpless Sub- Brandi Mae, Taperedphysique and CJ

XNXXGold 4 months ago

Drake Smiths Private Show

53% 4K 2:00 / 13:12

Drake Smiths Private Show

Flirt4Free 9 months ago

Guided Sissy JOI - Cock Sucking, Spit & CEI

Guided Sissy JOI - Cock Sucking, Spit & CEI

XHamster 8 months ago

Alexis Amadahy And Jade Sissy Training And Strap On

Alexis Amadahy And Jade Sissy Training And Strap On

AbXXX 3 years ago

Husband dressed up like a sissy bitch & pegged in his tight ass hole

Husband dressed up like a sissy bitch & pegged in his tight ass hole

XHamster 3 years ago

Ass-fuck Hooked Sissygasm during cuffed Gullet Teaching

Ass-fuck Hooked Sissygasm during cuffed Gullet Teaching

Gayhub 2 months ago

Luke Hardy & Cristian Ford Private Show

64% 4K 2:00 / 22:12

Luke Hardy & Cristian Ford Private Show

Flirt4Free 7 months ago

Drag Queen and Woman Makeover Transformation - Cleavage and Eyeliner

Drag Queen and Woman Makeover Transformation - Cleavage and Eyeliner

XHamster 1 year ago

Huge Dildo Anal Slut

Huge Dildo Anal Slut

XHamster 3 months ago

Show me how you pleasure yourself in front of me?

Premium HD 1:38

Show me how you pleasure yourself in front of me?

XNXXGold 2 years ago

Making My Husband into a Cuckold Sissy!

50% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 3 years ago

My Sissy, My Rules, Your New Life

66% HD 0:10 / 18:24

My Sissy, My Rules, Your New Life

LoyalFans 1 week ago

Hung Trans Mistresse Punishes Inactive Sissy Maid

Hung Trans Mistresse Punishes Inactive Sissy Maid

BigTitsLust 1 year ago

Playing Pee

FapHouse 5 months ago

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

69% HD 1:01 / 10:12

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

FapHouse 1 year ago

Shemale Black Widow Anal Destruction and Massive Creampie with Huge Dildo in Mating Press Position

59% HD 0:39 / 26:28

Shemale Black Widow Anal Destruction and Massive Creampie with Huge Dildo in Mating Press Position

FapHouse 4 months ago

Trans Cuckold Foot Slave Fucks Mistress's High Heel And Licks Cum From Her Toes - Jessica Bloom And Pineapple Punk

Trans Cuckold Foot Slave Fucks Mistress's High Heel And Licks Cum From Her Toes - Jessica Bloom And Pineapple Punk

XHamster 2 weeks ago

Erick Carre Private Show

63% HD 2:00 / 10:00

Erick Carre Private Show

Flirt4Free 4 months ago

Ass to mouth sissy training

73% HD 0:26 / 21:21

Ass to mouth sissy training

QueensOfKink 1 year ago

Time to Submit Sissy

Time to Submit Sissy

XHamster 3 months ago

NO MERCY - Prostate orgasm anal probe vibrator postorgasm

NO MERCY - Prostate orgasm anal probe vibrator postorgasm

XHamster 5 years ago

Destroy Your Own Cock Tutorial

HD 1:00 / 10:41

Destroy Your Own Cock Tutorial

Clips4sale 4 weeks ago

Sissy Whore Gets Ding-penis Experience - Full Version

Sissy Whore Gets Ding-penis Experience - Full Version

PornFreeNow 2 weeks ago

Soft Cock Training By Doctor Nicole (Prone Masturbation JOI)

Soft Cock Training By Doctor Nicole (Prone Masturbation JOI)

Clips4sale 9 months ago

Camilla Polls Private Show

47% 4K 2:00 / 7:05

Camilla Polls Private Show

Flirt4Free 1 year ago

Sissy Slave Training MyFreeShemale.com

Sissy Slave Training MyFreeShemale.com

Fapcat 4 years ago

Sexi Dance

62% HD 2:00 / 6:01

Flirt4Free 3 years ago

Gammers Boys

HD 2:00 / 26:49

Flirt4Free 2 years ago

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

XHamster 2 years ago

Adara Smith & Elver Rodriguez Private Show

HD 2:00 / 11:37

Adara Smith & Elver Rodriguez Private Show

Flirt4Free 3 years ago

Locktober Begins

Locktober Begins

FapHouse 1 week ago

Jasmine_dlight - Sexy Shemale Extreme Deep Anal Dildo Ride on 28inch Monster Vr180

64% VR 0:08 / 7:46

Jasmine_dlight - Sexy Shemale Extreme Deep Anal Dildo Ride on 28inch Monster Vr180

FapHouse 2 weeks ago

Let's give your damn hole a good massage with my strap-on and my fingers, my trans slut!

Let's give your damn hole a good massage with my strap-on and my fingers, my trans slut!

XHamster 2 weeks ago

Vends-ta-culottte - Anal training and pegging for submissive man by experienced brunette dominatrix

Vends-ta-culottte - Anal training and pegging for submissive man by experienced brunette dominatrix

XHamster 3 years ago

Breaking Her Sissy Doll Part 4 of 4: Anal Training with Fuck Machine, Huge Cock & Cum Eating with Mistress Stellina Obscura (1080p)

53% HD 0:30 / 27:09

Breaking Her Sissy Doll Part 4 of 4: Anal Training with Fuck Machine, Huge Cock & Cum Eating with Mistress Stellina Obscura (1080p)

Clips4sale 1 year ago

Anal Training, Learning

Anal Training, Learning

XHamster 8 months ago

Sissy Kate learns how to use the anal fucking machine with Lisa

Sissy Kate learns how to use the anal fucking machine with Lisa

XHamster 2 years ago

Trying to Stretch Myself on My Huge Fist Dildo I Just Got the Hand Inside Before Accidentally Squirting Cum

HD 1:01 / 11:23

Trying to Stretch Myself on My Huge Fist Dildo I Just Got the Hand Inside Before Accidentally Squirting Cum

FapHouse 2 years ago

Lika Kai Private Show

4K 2:00 / 17:34

Lika Kai Private Show

Flirt4Free 1 day ago

Maskedloki BBC breed trans sissies (Compilation)

Maskedloki BBC breed trans sissies (Compilation)

XHamster 2 years ago

Viky & Master Private Show

50% HD 2:00 / 25:32

Viky & Master Private Show

Flirt4Free 1 year ago

Pegging Session with My Chastity Slave

HD 0:39 / 10:51

Pegging Session with My Chastity Slave

FapHouse 4 years ago

Pink cock bondage fun for my sissy slut

Pink cock bondage fun for my sissy slut

XHamster 1 year ago

Stretched in more ways than one

Stretched in more ways than one

XHamster 2 years ago

Double Cock Sucker POV

Double Cock Sucker POV

Clips 3 weeks ago

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

46% HD 2:00 / 4:52

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

Flirt4Free 2 years ago

Helena Red Private Show

64% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 4 years ago

Perverted Anal Task Femdom POV

51% HD 0:39 / 18:58

Perverted Anal Task Femdom POV

FapHouse 6 months ago

Japanese tranny shamelessly faps in motel lobby

Japanese tranny shamelessly faps in motel lobby

TrannyGem 2 years ago

Sissy Maid Has the Best Boipussy

Sissy Maid Has the Best Boipussy

XHamster 1 year ago

Sissy Stuffing Perverted Tasks for Feminization Gay Training

Sissy Stuffing Perverted Tasks for Feminization Gay Training

FapHouse 1 month ago

Dungeon Bondage Trans Gets Anal Training

Dungeon Bondage Trans Gets Anal Training

FapHouse 6 months ago

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

55% HD 0:39 / 5:38

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

FapHouse 9 months ago

She-creature oral jobs the jizz out of GINORMOUS DARK-HUED MAN SAUSAGE

She-creature oral jobs the jizz out of GINORMOUS DARK-HUED MAN SAUSAGE

TransTube.tv 2 years ago

Jhordy & Maxx Private Show

64% HD 2:00 / 1:24:58

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Deep-Throating out his blossom with vacuum

Deep-Throating out his blossom with vacuum

GayCK 3 years ago

Even More Chilling Out with Some Porn..

Even More Chilling Out with Some Porn..

XHamster 1 year ago

My Femboy Roommate - 18 Year Old Femboy Wakes Me up with a Sloppy Blowjob

My Femboy Roommate - 18 Year Old Femboy Wakes Me up with a Sloppy Blowjob

XHamster 9 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

I Train Sweet Sissy Hole with My Strap-on

I Train Sweet Sissy Hole with My Strap-on

XHamster 1 month ago

FEMINIZED- Encouraged Feminization Play POV- Slut Training with Chastity Lock Up

44% HD 0:33 / 16:20

FEMINIZED- Encouraged Feminization Play POV- Slut Training with Chastity Lock Up

IWantClips 2 years ago

Muscular ebony domina pounding guy

Muscular ebony domina pounding guy

Some.Porn 10 months ago

Frisky night into the parking lot

Frisky night into the parking lot

XHamster 1 year ago

Anal Femdom: Mistress Jenna Turns Sissy Into a Filthy Ass to Mouth Slut!

Anal Femdom: Mistress Jenna Turns Sissy Into a Filthy Ass to Mouth Slut!

XHamster 5 months ago

I Dare You To Suck Cock For Me! Ft Miss Roper - 4K

I Dare You To Suck Cock For Me! Ft Miss Roper - 4K

Clips4sale 1 year ago

Big StepMommy loves to train her submissive sluts: bi encouragement and sissy training

Premium 57% HD 11:11

Big StepMommy loves to train her submissive sluts: bi encouragement and sissy training

XVideosRed 2 years ago

Dimitri Caruso Party on Aug 9, 2023

HD 2:00 / 36:16

Dimitri Caruso Party on Aug 9, 2023

Flirt4Free 3 years ago

Femboy dominates & TALKS DIRTY (Sissy Training JOI)

Femboy dominates & TALKS DIRTY (Sissy Training JOI)

Tranny.one 5 years ago

Total Transformation - HD

41% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 1 year ago

I Gave Him a Priceless Fleshly Prostate Massage and Pegged His Butt Hard

I Gave Him a Priceless Fleshly Prostate Massage and Pegged His Butt Hard

FreePorn8 2 weeks ago

Two Dommes And The Delivery Boy - Throat Trained

Premium HD 5:11

Two Dommes And The Delivery Boy - Throat Trained

XVideosRed 1 year ago

Sissy Girls Day: Makeover and Feminization Training - Part 2.mp4

63% HD 1:01 / 15:12

Sissy Girls Day: Makeover and Feminization Training - Part 2.mp4

FapHouse 3 months ago

Asian Dommes Training White Sissy Slave Kassie

Asian Dommes Training White Sissy Slave Kassie

XHamster 1 day ago

Be Ready for the Really Big Cocks Part2

Be Ready for the Really Big Cocks Part2

XHamster 1 year ago

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