Training Videos - Trans (89,638)

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

RedTube Unknown

MAKING LUNA A SLUT FOR OUR STRAPON COCKS 1080P - ELLIE IDOL, CHASTITY LYNN & LUNA LAIKA

68% HD 0:11 / 21:24

MAKING LUNA A SLUT FOR OUR STRAPON COCKS 1080P - ELLIE IDOL, CHASTITY LYNN & LUNA LAIKA

Clips4sale 3 years ago

Shaved humiliated and Sissified by 4 Ladies wmv

57% HD 0:30 / 14:14

Shaved humiliated and Sissified by 4 Ladies wmv

Clips4sale 1 year ago

Sophia Loreen Party on Apr 18, 2026 - Part 3

HD 2:00 / 34:42

Sophia Loreen Party on Apr 18, 2026 - Part 3

Flirt4Free 1 week ago

Subordination Training kicking balls DICK AND BALL TORMENT

Subordination Training kicking balls DICK AND BALL TORMENT

Gayhaus 1 year ago

BNWO Sissy Breeding Stables

42% HD 0:29 / 10:41

BNWO Sissy Breeding Stables

Clips4sale 7 months ago

Sofia Devero Private Show

HD 2:00 / 20:10

Sofia Devero Private Show

Flirt4Free 2 years ago

Tiffanny Lombardi Private Show

63% HD 2:00 / 15:57

Tiffanny Lombardi Private Show

Flirt4Free 2 years ago

On the beach I turn my spouse's ramrod into vagina

On the beach I turn my spouse's ramrod into vagina

MatureTubeHere 2 years ago

Sissy Maker 5 720

Sissy Maker 5 720

XVideos 7 years ago

Group Spanking Session and Sexy Oral Play

HD 2:00 / 49:13

Group Spanking Session and Sexy Oral Play

Flirt4Free 8 years ago

Your Angel Cynthia Anal Training And Throat Fucking

Your Angel Cynthia Anal Training And Throat Fucking

ProPorn 2 years ago

Japanese dominatrix Mikako trains two transvestite slaves

Japanese dominatrix Mikako trains two transvestite slaves

XVideos 2 years ago

Good Girl Sissy Pegging SD

Good Girl Sissy Pegging SD

Clips4sale 3 years ago

DIVINE FEMININITY FOR CROSSDRESSERS AND SISSIES - Feminization Training [Divine Feminity] [Feminine] [Sissy] [Sissification] [Crossdressing]

DIVINE FEMININITY FOR CROSSDRESSERS AND SISSIES - Feminization Training [Divine Feminity] [Feminine] [Sissy] [Sissification] [Crossdressing]

Clips4sale 1 year ago

Sissy Training 03 Get Your Asshole Ready For BBC

Sissy Training 03 Get Your Asshole Ready For BBC

Eporner 1 month ago

Turkish trans slut in red lingerie and heels gets her ass oiled up and fucked hard

Turkish trans slut in red lingerie and heels gets her ass oiled up and fucked hard

XGroovy 2 years ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 2 months ago

HOT SHOTS SISSY PEGGING FISTING TRENNING COMPILATION

HOT SHOTS SISSY PEGGING FISTING TRENNING COMPILATION

XVideos 1 year ago

Diaper Sissy Truth or Dare

Diaper Sissy Truth or Dare

Clips4sale 7 months ago

Sissified Male Suffering and Strung Up - Part 2

57% 0:30 / 9:59

Sissified Male Suffering and Strung Up - Part 2

Clips4sale 1 year ago

Lingerie Lover - Sissy Pegging POV

71% 4K 0:30 / 15:25

Lingerie Lover - Sissy Pegging POV

Clips4sale 1 year ago

The Art and Beauty Of Bondage / Shibari / Kinbaku

The Art and Beauty Of Bondage / Shibari / Kinbaku

XVideos 4 weeks ago

Sissy Step 3

34% 0:25 / 13:07

Clips4sale 2 years ago

STROKE FOR DICK FAGGOT

61% 4K 0:25 / 8:55

STROKE FOR DICK FAGGOT

Clips4sale 3 years ago

Big Cocked Tinder Date: Anal Fuck POV - Gwen Adora BBW Futanari Anal Training - hd mp4

HD 0:30 / 12:23

Big Cocked Tinder Date: Anal Fuck POV - Gwen Adora BBW Futanari Anal Training - hd mp4

Clips4sale 3 years ago

deep throat training with a big dildo

deep throat training with a big dildo

xHamster 1 year ago

”Blond mouth screwed & cummed in bdsm”

”Blond mouth screwed & cummed in bdsm”

TransHero 4 months ago

TRANSFORMATION INTO A GRANNY - CHEAP LOSER PRICE

65% 0:30 / 18:19

TRANSFORMATION INTO A GRANNY - CHEAP LOSER PRICE

Clips4sale 5 months ago

90 pumps on inflatable long dildo all the way in extreme anal training for sissy sub slut

90 pumps on inflatable long dildo all the way in extreme anal training for sissy sub slut

xHamster 3 years ago

negao pauzudo fodeu no pelo a trans loira em puplico

negao pauzudo fodeu no pelo a trans loira em puplico

PornBox 2 weeks ago

Tongue Fuck my Rubber Boots Preview - Oscar Thickk

Tongue Fuck my Rubber Boots Preview - Oscar Thickk

xHamster 3 years ago

Worship Girl Cock

39% 0:10 / 11:04

Worship Girl Cock

Clips4sale 5 months ago

secret sissy weekend with your homewrecker goth gf: Sunday

51% HD 0:28 / 10:56

secret sissy weekend with your homewrecker goth gf: Sunday

Clips4sale 2 years ago

Hot Submissive Tgirl Slut Hired to Take Down Dictation Drink Piss Eat Ass Swallow Cum

Hot Submissive Tgirl Slut Hired to Take Down Dictation Drink Piss Eat Ass Swallow Cum

XVideos 1 year ago

Mistress Elizabelle Dixie trains and fucks PuppyGirl Variety Itsol session: one

67% 0:30 / 13:02

Mistress Elizabelle Dixie trains and fucks PuppyGirl Variety Itsol session: one

Clips4sale 11 months ago

FEMDOM SISSY TRAINNING COMPILATION CUMSHOTS SISSYGASM

FEMDOM SISSY TRAINNING COMPILATION CUMSHOTS SISSYGASM

XVideos 1 year ago

Multiple Cums For My Demonic Aroma You Slut

Premium HD 10:56

Multiple Cums For My Demonic Aroma You Slut

Clips4sale 1 week ago

FemBoy caught on cam playing with Fucking machine

FemBoy caught on cam playing with Fucking machine

xHamster 1 year ago

FULL MOVIE The New Black Neighbor

41% HD 0:30 / 1:07:03

FULL MOVIE The New Black Neighbor

Clips4sale 1 year ago

HOT SHOTS ORGASM COMPILATION

HOT SHOTS ORGASM COMPILATION

XVideos 1 year ago

Lifestyle Rope Bondage Crossdresser Sissy Deanne - Stella Liberty - DID, rope play, femdom, sissification - 4K MP4

4K 0:15 / 22:20

Lifestyle Rope Bondage Crossdresser Sissy Deanne - Stella Liberty - DID, rope play, femdom, sissification - 4K MP4

Clips4sale 1 year ago

If You Want to Suck My Dick

70% 0:11 / 12:59

If You Want to Suck My Dick

Clips4sale 2 years ago

AB121 Lustful succubus extreme training

AB121 Lustful succubus extreme training

YouPorn Unknown

The Sissycdmish Situation Is Out of Control!

The Sissycdmish Situation Is Out of Control!

xHamster 8 months ago

4K - Fallen Vespers Femboy Double Confessing Cumshots

4K 0:19 / 31:08

4K - Fallen Vespers Femboy Double Confessing Cumshots

Clips4sale 2 weeks ago

Hellish Aroma Trapdoor Part 5

64% 0:42 / 7:52

Hellish Aroma Trapdoor Part 5

Clips4sale 7 months ago

4K- Horny Air Hostess - Original Character

65% 4K 0:19 / 18:16

4K- Horny Air Hostess - Original Character

Clips4sale 3 years ago

Talia Hot Private Show

Talia Hot Private Show

Flirt4Free 2 weeks ago

Foot Worship With Bella Hart

Foot Worship With Bella Hart

Clips4sale 3 years ago

Sofia Ferreira Private Show

Sofia Ferreira Private Show

Flirt4Free 9 months ago

Pure girl in a sailor dress and long socks trains her own anus with anal fisting and a huge anal plug

HD 0:39 / 12:00

Pure girl in a sailor dress and long socks trains her own anus with anal fisting and a huge anal plug

FapHouse 1 month ago

Your New Life: Hormones, Heels, and Getting Passed Around

Your New Life: Hormones, Heels, and Getting Passed Around

Clips4sale 5 months ago

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny lustful as fuck!”

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny lustful as fuck!”

HQBang 2 years ago

24h Stepbro & Sis Body Swapped & Maid Dress up

HD 0:20 / 10:15

24h Stepbro & Sis Body Swapped & Maid Dress up

Clips4sale 1 year ago

Princess Donna Snatches Good Girls Up In Cages (1 HR NO PEE)

Princess Donna Snatches Good Girls Up In Cages (1 HR NO PEE)

XVideos 1 year ago

”Tranny Gorgeous Aubrey Kate's Seductive Training & Passionate Pleasure”

”Tranny Gorgeous Aubrey Kate's Seductive Training & Passionate Pleasure”

LesbianBliss 3 months ago

Gag Reflex Training Failure for the stupid and dumbest Princesse "Pukie 🤮" Lumi

Gag Reflex Training Failure for the stupid and dumbest Princesse "Pukie 🤮" Lumi

xHamster 2 years ago

AB082 Bad Girl Miss 3 be spanking and training - deep throat crmpie (Chinese and English subtitles)

AB082 Bad Girl Miss 3 be spanking and training - deep throat crmpie (Chinese and English subtitles)

YouPorn Unknown

Valery Brett Private Show

HD 2:00 / 12:24

Valery Brett Private Show

Flirt4Free 1 day ago

Big tits blonde transsexual EMT trainer Jade Venus fucking her student

Big tits blonde transsexual EMT trainer Jade Venus fucking her student

Wankoz 1 week ago

Onyushka Anal Training With Big Sex Toy

Onyushka Anal Training With Big Sex Toy

VipTube 3 months ago

TRANSSEXUAL W I L L O W - Encaged Sissy Fap

TRANSSEXUAL W I L L O W - Encaged Sissy Fap

TrannyGem 1 year ago

Sissy Byron Cole Gasps Themself while they Jism!

Sissy Byron Cole Gasps Themself while they Jism!

GayCK 5 years ago

Cosplay slut Jenby Doll gets trained by Skye January (short version)

Cosplay slut Jenby Doll gets trained by Skye January (short version)

XVideos 3 years ago

THREESOME with Salome Salvi and Tantaly Sex Doll

64% 4K 0:30 / 30:54

THREESOME with Salome Salvi and Tantaly Sex Doll

Clips4sale 2 years ago

You are Diaper Sissy Step-Sisters

4K 0:30 / 16:30

You are Diaper Sissy Step-Sisters

Clips4sale 10 months ago

[Trans] Ass Training Lilia Lust!

VR 1:30 / 20:35

[Trans] Ass Training Lilia Lust!

VRPorn 10 months ago

Submissive Asian Ladyboy Firts Anal Casting & Slave Training

HD 1:01 / 38:36

Submissive Asian Ladyboy Firts Anal Casting & Slave Training

FapHouse 3 weeks ago

Feminized into surgeons bimbo sex slave - PART 1

46% HD 0:11 / 6:15

Feminized into surgeons bimbo sex slave - PART 1

Clips4sale 2 years ago

Im Intend To Turn u into a Cock Sucker and Put u on the Street Sissy Boi TGIRL PIMP VERSION

Im Intend To Turn u into a Cock Sucker and Put u on the Street Sissy Boi TGIRL PIMP VERSION

ShemaleSin 4 years ago

| JOI & ASMR | Dream Trans Goth GF clicker trains you Pt.1

| JOI & ASMR | Dream Trans Goth GF clicker trains you Pt.1

RedTube Unknown

PLUGGED + LOCKED = THE SISSY WHORE [Sissy Training Reinforcement] [Sissy] [Chastity] [Chastity Device] [ButtPlug] [Plugged] [Plugged in Chastity] [Plug] [Butt] [Chastity Training] [Locked in Chastity] [Chastity Cage] [Caged]

PLUGGED + LOCKED = THE SISSY WHORE [Sissy Training Reinforcement] [Sissy] [Chastity] [Chastity Device] [ButtPlug] [Plugged] [Plugged in Chastity] [Plug] [Butt] [Chastity Training] [Locked in Chastity] [Chastity Cage] [Caged]

Clips4sale 1 year ago

AB121 Lustful succubus extreme training

AB121 Lustful succubus extreme training

RedTube Unknown

Cum-Soaked Devotion: Serving My Divine Shemale BBC Pastors

Premium HD 12:28

Cum-Soaked Devotion: Serving My Divine Shemale BBC Pastors

Clips4sale 1 year ago

SEXY CROSDRESSER IN LINGERIE AND A SMALL chastity belt MAKES A VIDEO FOR HER LOVER.

SEXY CROSDRESSER IN LINGERIE AND A SMALL chastity belt MAKES A VIDEO FOR HER LOVER.

XVideos 3 years ago

Vulva dude maid attempts to keep composure while getting machine penetrated

Vulva dude maid attempts to keep composure while getting machine penetrated

Transvids.tv 9 months ago

Goth domina Dressing up her new crossdresser TV sissy slave pt1 HD

Goth domina Dressing up her new crossdresser TV sissy slave pt1 HD

XVideos 5 years ago

OnlyFans - Waltlovesyouxo And Bambifyme - Anal Training

OnlyFans - Waltlovesyouxo And Bambifyme - Anal Training

TubeOn 1 year ago

Jocks Show Off and Play with Dildo

HD 2:00 / 12:50

Jocks Show Off and Play with Dildo

Flirt4Free 8 years ago

Double dom with Lady Valeska: Sissy begs for cum

Double dom with Lady Valeska: Sissy begs for cum

Clips4sale 1 year ago

Jacob Malik Private Show

64% HD 2:00 / 8:00

Jacob Malik Private Show

Flirt4Free 5 months ago

4K - Femcock vs Vibrator Round 8 ~Intimate~

4K 0:20 / 10:48

4K - Femcock vs Vibrator Round 8 ~Intimate~

Clips4sale 1 week ago

”Sissy Dick Slut Training (Audio Erotica)”

”Sissy Dick Slut Training (Audio Erotica)”

TransHero 1 month ago

Rub Your Sissy Clitty for Cock

Rub Your Sissy Clitty for Cock

Clips4sale 3 years ago

Diapered sissy luvs gigantic faux-cock

Diapered sissy luvs gigantic faux-cock

TrannyGem 1 year ago

Lewd Stepdaughter Rides Massive 13 Inch Sex tool And Cums From Anal Screw Machine

Lewd Stepdaughter Rides Massive 13 Inch Sex tool And Cums From Anal Screw Machine

ShemaleSin 4 months ago

Janet Discloses Her True Raunchy Identity

Janet Discloses Her True Raunchy Identity

ShemaleSin 1 year ago

Femboy thighjobs go ULTRA-KINKY

Femboy thighjobs go ULTRA-KINKY

Gayhub 11 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 month ago

Sissy Compilation Public riding dildo

Sissy Compilation Public riding dildo

XVideos 1 year ago

Her Slave Uncaged - Chelsea Poe and Sinn Sage Trans Lesbian Domination With BDSM and Strapon Fucking WMV

HD 0:19 / 32:41

Her Slave Uncaged - Chelsea Poe and Sinn Sage Trans Lesbian Domination With BDSM and Strapon Fucking WMV

Clips4sale 6 months ago

FemGape Creamy Big Anal Training With Dildo

FemGape Creamy Big Anal Training With Dildo

TubeOn 3 months ago

Deep Training - Kasey Kei

Deep Training - Kasey Kei

XVideos 5 years ago

Trans Domme Trains her Male Sub 3

Trans Domme Trains her Male Sub 3

XVideos 3 weeks ago

”Veronica Avluv Messed Up Like A Cheap Bitch”

”Veronica Avluv Messed Up Like A Cheap Bitch”

ThePornstar 1 year ago

Sissy Sucks Daddy’s Large Ramrod

Sissy Sucks Daddy’s Large Ramrod

ShemaleSin 4 years ago

Alana Ebony & Matt Benett Private Show

HD 2:00 / 17:31

Alana Ebony & Matt Benett Private Show

Flirt4Free 3 years ago

Sissy Tgirl Kassandra gets bullied and trained at BBCU with Lady Anaconda and Lady Viper 🖤🎀

63% HD 0:10 / 25:59

Sissy Tgirl Kassandra gets bullied and trained at BBCU with Lady Anaconda and Lady Viper 🖤🎀

LoyalFans 2 months ago

Your just a fucking loser sissy

63% HD 0:30 / 13:02

Your just a fucking loser sissy

Clips4sale 3 years ago

Luna's mandatory arch training w/ humbler and metal locking anal hook and collar

Luna's mandatory arch training w/ humbler and metal locking anal hook and collar

ShemaleSin 1 year ago

Sasha Earth fuck on the bed at home different anal sex toys

Sasha Earth fuck on the bed at home different anal sex toys

XVideos 3 years ago

4K - Ichigo Femboy Pervert Panties Sucking + Cum Swallowing Play ~Ichigo x Strawberry Festival~

4K 0:18 / 18:09

4K - Ichigo Femboy Pervert Panties Sucking + Cum Swallowing Play ~Ichigo x Strawberry Festival~

Clips4sale 2 months ago

Top 10 Sissy Ideas 2023 (Pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

58% HD 0:29 / 21:54

Top 10 Sissy Ideas 2023 (Pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Clips4sale 1 year ago

Sasha Earth have anal sex at home with sex toys

Sasha Earth have anal sex at home with sex toys

XVideos 4 years ago

Jasmine Dlight & Hannah Blake & Mistress Ae - Double Dom - Extreme Anal Strapon Slut

Jasmine Dlight & Hannah Blake & Mistress Ae - Double Dom - Extreme Anal Strapon Slut

xHamster 8 months ago

SometimesNiki sissy maid anal training

SometimesNiki sissy maid anal training

xHamster 1 year ago

Victoria's New TV Slave - WMV - 1440

Victoria's New TV Slave - WMV - 1440

Clips4sale 2 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 11 months ago

TRANS AND GIRL ON ONE DILDO

TRANS AND GIRL ON ONE DILDO

XVideos 1 year ago

ryu Doll letting her machine do the work

ryu Doll letting her machine do the work

Pornzona 1 month ago

Фембой шлюшка компиляция оргазма анальные игры с дилдо сквирт шоу

Фембой шлюшка компиляция оргазма анальные игры с дилдо сквирт шоу

XVideos 1 year ago

Blasphemy Pump

Premium HD 14:56

Clips4sale 1 week ago

HOT ORGASM CUMSHOTS COMPILATION

HOT ORGASM CUMSHOTS COMPILATION

XVideos 1 year ago

Sissy Supah-mega-slut gets Drilled by BIG BLACK COCK

Sissy Supah-mega-slut gets Drilled by BIG BLACK COCK

TransTube.tv 1 year ago

Weg mit dem Schwanz &ndash_ Die Lady der Feminisierung verpasst Dir Sissyfotze ein h&uuml_bsches Cameltoe-H&ouml_schen

Weg mit dem Schwanz &ndash_ Die Lady der Feminisierung verpasst Dir Sissyfotze ein h&uuml_bsches Cameltoe-H&ouml_schen

XVideos 2 years ago

Become My Femme Bestie Fill-In To Date Me

Become My Femme Bestie Fill-In To Date Me

Clips4sale 2 years ago

Door To Door - Cassie Cummings And Sinn Sage MP4

63% 0:22 / 35:55

Door To Door - Cassie Cummings And Sinn Sage MP4

Clips4sale 3 years ago

Slut Training Session

Slut Training Session

xHamster 6 months ago

How to Teach Your Sissy Boyfriend

How to Teach Your Sissy Boyfriend

ShemaleSin 4 months ago

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89,638 results found

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