Training Videos - Trans (87,237)

Crossdresser Rough anal fuck with rock hard red monster dildo

Crossdresser Rough anal fuck with rock hard red monster dildo

xHamster 11 months ago

Japanese tranny shamelessly faps in motel lobby

Japanese tranny shamelessly faps in motel lobby

TrannyGem 2 years ago

Lick the taste of ass from my finger KellyAErick

Lick the taste of ass from my finger KellyAErick

Tranny.one 2 years ago

Bombshell

xHamster 5 months ago

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

67% HD 1:01 / 26:52

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

FapHouse 1 year ago

Jacob Malik Private Show

46% HD 2:00 / 16:32

Jacob Malik Private Show

Flirt4Free 4 months ago

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and Transgender Identity

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and Transgender Identity

xHamster 7 months ago

Ivy & Headmistress; Sissification & Humiliation Punishment

59% 0:39 / 26:37

Ivy & Headmistress; Sissification & Humiliation Punishment

FapHouse 1 year ago

Sophia Loreen Private Show

HD 2:00 / 10:44

Sophia Loreen Private Show

Flirt4Free 1 year ago

Amannda Skye Party on Dec 10, 2025

54% 4K 2:00 / 50:18

Amannda Skye Party on Dec 10, 2025

Flirt4Free 2 months ago

Femdom POV: Humiliating My Cuck Ex Ep 3

HD 0:39 / 12:34

Femdom POV: Humiliating My Cuck Ex Ep 3

FapHouse 15 hours ago

GENDER X Tranny cheerleader rides on BBC - Smash Thompson,Ella Hollywood

GENDER X Tranny cheerleader rides on BBC - Smash Thompson,Ella Hollywood

Fapnado 4 years ago

Sexy Sissy Dancing and Posing in New Lingerie

Sexy Sissy Dancing and Posing in New Lingerie

FapHouse 2 years ago

What a pathetic sissy slut - Time for punishment

What a pathetic sissy slut - Time for punishment

xHamster 2 weeks ago

Playtime 69

xHamster 4 months ago

Fitness Influencer Gets Creampied During a Training Session

54% HD 1:01 / 2:01:05

Fitness Influencer Gets Creampied During a Training Session

FapHouse 2 months ago

Nyxi Leon Fucked in 5 Different Positions by TS Mistress Bailey Love & More!

78% HD 1:01 / 19:53

Nyxi Leon Fucked in 5 Different Positions by TS Mistress Bailey Love & More!

FapHouse 1 year ago

I NUTTING from RIGID CABLE ON SMASH

I NUTTING from RIGID CABLE ON SMASH

TrannyGem 3 years ago

Inflatable plug to make my sissy ejaculate

Inflatable plug to make my sissy ejaculate

xHamster 3 months ago

Teacher Reina's Alphabet Lesson of Sexual Terms

68% HD 1:01 / 28:18

Teacher Reina's Alphabet Lesson of Sexual Terms

FapHouse 2 months ago

Anal Slut Ryan74 Inserts Cold Coca Cola Can in Ass

Anal Slut Ryan74 Inserts Cold Coca Cola Can in Ass

xHamster 1 year ago

BIG BLACK COCK Neighbor Back For More Dirty Head From Pretty Trans Woman

BIG BLACK COCK Neighbor Back For More Dirty Head From Pretty Trans Woman

Transvids.tv 1 year ago

Chastity Sissy Maid Service Training With Ria Bentley

Chastity Sissy Maid Service Training With Ria Bentley

Amateur8 3 months ago

A Girl Is Going to Get Her Ass Fisted

A Girl Is Going to Get Her Ass Fisted

FapHouse 2 months ago

Tied Up Sissy Gets Wanked Off

Tied Up Sissy Gets Wanked Off

xHamster 2 years ago

Dripping Sissy Slut

55% HD 0:10 / 16:20

Dripping Sissy Slut

LoyalFans 3 years ago

Sissy For Alphas

60% HD 0:10 / 5:18

Sissy For Alphas

LoyalFans 1 year ago

Alexxa A Private Show

63% HD 2:00 / 15:39

Alexxa A Private Show

Flirt4Free 1 month ago

Sophia Loreen Private Show

58% HD 2:00 / 13:50

Sophia Loreen Private Show

Flirt4Free 7 months ago

A Dominant Woman Will Use This Submissive Tgirl for a Medical Examination

54% HD 1:01 / 16:50

A Dominant Woman Will Use This Submissive Tgirl for a Medical Examination

FapHouse 3 months ago

Bunny-butler Reina Hanno Sucking Two Dildos

55% HD 0:39 / 23:41

Bunny-butler Reina Hanno Sucking Two Dildos

FapHouse 4 months ago

A Day in the Sissy Life

66% HD 0:39 / 15:11

A Day in the Sissy Life

FapHouse 11 months ago

Sissy training for your feminization

68% HD 0:39 / 7:27

Sissy training for your feminization

FapHouse 2 years ago

Sissy Anal Training by Latex Dommes

Sissy Anal Training by Latex Dommes

FapHouse 9 months ago

SLENDER RESIGNED LADYBOY SELF ANAL FISTING AND THRALL TRAINING

SLENDER RESIGNED LADYBOY SELF ANAL FISTING AND THRALL TRAINING

ShemaleSin 8 months ago

Self-Training No70 Outdoor Masturbation Machine

Self-Training No70 Outdoor Masturbation Machine

xHamster 1 month ago

Feminising my sissy boi husband and pegging his tight hole and filling his mouth with cum

Feminising my sissy boi husband and pegging his tight hole and filling his mouth with cum

xHamster 2 years ago

She Trains Her Sissy Friend to Receive Cocks

She Trains Her Sissy Friend to Receive Cocks

FapHouse 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

Shemale Jane Glory Hole Handjob & Blowjob From Seiko

Shemale Jane Glory Hole Handjob & Blowjob From Seiko

FapHouse 1 month ago

Long Machine Fuck for Bi Slut with Huge Fake Tits

HD 1:01 / 19:05

Long Machine Fuck for Bi Slut with Huge Fake Tits

FapHouse 2 years ago

Long Machine Fuck for Bi Slut with Huge Fake Tits

HD 0:39 / 19:05

Long Machine Fuck for Bi Slut with Huge Fake Tits

FapHouse 2 years ago

GOONTARD FOR SHEMALE BIMBOS

60% HD 0:10 / 33:34

GOONTARD FOR SHEMALE BIMBOS

LoyalFans 6 months ago

Honeypot Teaching

Honeypot Teaching

TrannyGem 4 years ago

Worship Superior Foreskin

57% HD 1:01 / 13:16

Worship Superior Foreskin

FapHouse 1 month ago

Post Op Trans Woman Masturbation - Compilation 2

53% HD 0:39 / 20:08

Post Op Trans Woman Masturbation - Compilation 2

FapHouse 1 year ago

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

55% HD 0:39 / 25:09

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

FapHouse 7 months ago

Sissy Caned by Two Cruel Mistresses

65% HD 1:01 / 15:23

Sissy Caned by Two Cruel Mistresses

FapHouse 2 months ago

Sophia Loreen Party on Jan 22, 2026 - Part 2

61% 4K 2:00 / 48:40

Sophia Loreen Party on Jan 22, 2026 - Part 2

Flirt4Free 1 month ago

FISTING OUTDOOR COMPILATION

FISTING OUTDOOR COMPILATION

aShemaleTube 8 months ago

Teaching my SPANDEX SISSY whore GUTS with my NURSE MITTENS

Teaching my SPANDEX SISSY whore GUTS with my NURSE MITTENS

TrannyGem 1 month ago

Sissy Fuckdoll

xHamster 1 year ago

RUINED TWICE!!! Post Orgasm Handjob

RUINED TWICE!!! Post Orgasm Handjob

xHamster 3 years ago

Rachael Belle In ass-fuck Trainer

Rachael Belle In ass-fuck Trainer

TransTube.tv 5 months ago

Mrhankeys PIN-CLOP 4XL very first time

Mrhankeys PIN-CLOP 4XL very first time

MenGem 1 year ago

Mistress Trains Her Sissy Gurls

Mistress Trains Her Sissy Gurls

BeMyHole 5 years ago

Viky & Master Private Show

60% HD 2:00 / 10:29

Viky & Master Private Show

Flirt4Free 2 months ago

Trans Dresses as Teacher, Cosplay, Wants to Play with His Students

73% 1:01 / 5:40

Trans Dresses as Teacher, Cosplay, Wants to Play with His Students

FapHouse 1 year ago

Sissy tranny takes a smoke and gives head to daddy

Sissy tranny takes a smoke and gives head to daddy

Tranny.one 8 years ago

Cage Loser, You Stay Locked up - While Im Masturbating! German Deutsch

Cage Loser, You Stay Locked up - While Im Masturbating! German Deutsch

FapHouse 3 weeks ago

Sissy Having Fun on the Swing

Sissy Having Fun on the Swing

FapHouse 5 days ago

Cute Succubus Wants to Take All Your Cum This Halloween

57% HD 0:39 / 22:08

Cute Succubus Wants to Take All Your Cum This Halloween

FapHouse 2 years ago

Sissy squirts from her caged clit while riding her BBC dildo

Sissy squirts from her caged clit while riding her BBC dildo

xHamster 9 months ago

Wild Sabrina Members-Only Show

45% HD 2:00 / 12:20

Wild Sabrina Members-Only Show

Flirt4Free 5 years ago

Peter Is Wanking Over Lady Boys

Peter Is Wanking Over Lady Boys

FapHouse 1 year ago

Greedy Cock Taking Slut Gets Her Sissy Ass Destroyed!

HD 1:01 / 28:18

Greedy Cock Taking Slut Gets Her Sissy Ass Destroyed!

FapHouse 3 weeks ago

Salimur BJ training for big cocks💋

Salimur BJ training for big cocks💋

aShemaleTube 1 year ago

Sissy Secretary: Submissive Male Feminized Into Bimbo for Job Interview, Learns How to Pee Like a Girl, Bonus Pegging & Fisting

52% HD 1:01 / 8:31

Sissy Secretary: Submissive Male Feminized Into Bimbo for Job Interview, Learns How to Pee Like a Girl, Bonus Pegging & Fisting

FapHouse 10 months ago

21yo Femboy Viii penalized

21yo Femboy Viii penalized

TransTube.tv 8 months ago

She Dreams So Much It Was Hers That She Ejaculates

She Dreams So Much It Was Hers That She Ejaculates

TrannyGem 4 weeks ago

Dildo Dick Down Vol 1

HD 1:01 / 39:39

Dildo Dick Down Vol 1

FapHouse 1 week ago

Sissy Stacy First Spring Days Walking at the Railway

Sissy Stacy First Spring Days Walking at the Railway

FapHouse 10 months ago

AB121 Lustful succubus extreme training

AB121 Lustful succubus extreme training

xHamster 1 year ago

AB104 Sex toy tester surrender (English subtitles)

AB104 Sex toy tester surrender (English subtitles)

Tranny.one 1 year ago

S043 - Anal with Big Dildo 8

66% HD 1:01 / 16:08

S043 - Anal with Big Dildo 8

FapHouse 6 months ago

Sissy In A Green Bikini Riding A Black Dildo

Sissy In A Green Bikini Riding A Black Dildo

xHamster 9 months ago

Lana Page gape training - amateur crossdresser debut (part2)

Lana Page gape training - amateur crossdresser debut (part2)

xHamster 4 years ago

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

FapHouse 16 hours ago

Sissy Lovelaska - hot anal games. Balls and big dildo

Sissy Lovelaska - hot anal games. Balls and big dildo

xHamster 4 years ago

Pissing on my cute femboy GF Hayley

Pissing on my cute femboy GF Hayley

xHamster 4 months ago

Jeni Justice Trained And Turned Into A Sexy Sissy

Jeni Justice Trained And Turned Into A Sexy Sissy

AbTranny 2 years ago

French Sissy Destroys Her Ass

French Sissy Destroys Her Ass

xHamster 1 month ago

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

TransTube.tv 1 year ago

Trainer's Training No90 Swollen Anal Play

Trainer's Training No90 Swollen Anal Play

xHamster 3 weeks ago

”GENDER X Shemale cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

”GENDER X Shemale cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

Fapnow 4 years ago

Sexy Trans Secretary Discipline Encounter With The Boss

Sexy Trans Secretary Discipline Encounter With The Boss

FreePorn8 1 month ago

Massive group sex of trans fucking females with MILF Dee

Massive group sex of trans fucking females with MILF Dee

Yeswegays 3 years ago

Intense cumshot amateur porn compilation

Intense cumshot amateur porn compilation

AnySex 2 years ago

Trans Anal Training with Dildo

Trans Anal Training with Dildo

xHamster 8 months ago

Shemale Jane Glory Hole Handjob & Blowjob From Seiko

63% HD 1:01 / 9:12

Shemale Jane Glory Hole Handjob & Blowjob From Seiko

FapHouse 1 month ago

Lick up Every Drop of Pre-cum! Only Then Can You Cum on My Jeans Ass! JOI CEI German

Lick up Every Drop of Pre-cum! Only Then Can You Cum on My Jeans Ass! JOI CEI German

FapHouse 3 weeks ago

Advanced Anal Stretching with Jasmine-dlight: Part 2 - Standing Position

69% HD 1:01 / 9:57

Advanced Anal Stretching with Jasmine-dlight: Part 2 - Standing Position

FapHouse 5 months ago

The bondage and feminization of a slave by a blonde queen

The bondage and feminization of a slave by a blonde queen

xHamster 1 year ago

Seduced By Silk - Star Nine

58% HD 0:10 / 13:41

Seduced By Silk - Star Nine

LoyalFans 2 years ago

In Sissy Clothes, This Is How You'll Soon Look

In Sissy Clothes, This Is How You'll Soon Look

FapHouse 1 week ago

Sissy Femboy

48% 1:01 / 5:47

FapHouse 2 years ago

Even More Chilling Out with Some Porn..

Even More Chilling Out with Some Porn..

xHamster 9 months ago

Sexy Lace Lingerie Dildo Playing

HD 1:01 / 14:58

Sexy Lace Lingerie Dildo Playing

FapHouse 4 days ago

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

TrannyGem 4 years ago

Hot Training, Come See Ass Warming At Prezotte’s House With Personal Trainee Breno Dias And Sabrina Prezotte.

Hot Training, Come See Ass Warming At Prezotte’s House With Personal Trainee Breno Dias And Sabrina Prezotte.

BeMyHole 4 months ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 1

63% HD 1:01 / 20:07

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 1

FapHouse 1 year ago

blowing pricks compliation and getting a facial cumshot

blowing pricks compliation and getting a facial cumshot

TransTube.tv 1 year ago

Gtavanessabitchx the Beautiful Little Whore of the Neighborhood. She Loves Licking the Guys' Cock. Sperm Discharge

HD 1:01 / 40:46

Gtavanessabitchx the Beautiful Little Whore of the Neighborhood. She Loves Licking the Guys' Cock. Sperm Discharge

FapHouse 2 months ago

Hanna Ven Private Show

56% HD 2:00 / 10:55

Hanna Ven Private Show

Flirt4Free 1 year ago

Orgy and trains of the CentoXCento with the trans Sabrina Pa

Orgy and trains of the CentoXCento with the trans Sabrina Pa

xHamster 4 years ago

YOU’RE GAY & THAT’S OK

60% HD 0:10 / 7:56

YOU’RE GAY & THAT’S OK

LoyalFans 2 years ago

Isabella fucked by 2 guys in pink

Isabella fucked by 2 guys in pink

aShemaleTube 1 year ago

Riding a dildo in a miniskirt

65% 0:39 / 5:14

Riding a dildo in a miniskirt

FapHouse 2 weeks ago

Crossdresser Latex Mini Skirt Fishnet Anal Gape Training Monster Dildos Plugs

HD 0:39 / 10:48

Crossdresser Latex Mini Skirt Fishnet Anal Gape Training Monster Dildos Plugs

FapHouse 2 years ago

YOU LOVE SHEMALES

56% HD 0:10 / 18:43

YOU LOVE SHEMALES

LoyalFans 5 months ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

xHamster 1 year ago

Intense Bondage Training: Duct Tape Spanking with Fetish Slut and Luciaskywalker

Intense Bondage Training: Duct Tape Spanking with Fetish Slut and Luciaskywalker

JuicyVid 3 weeks ago

Sarah and Lucy Feminize You and Breezy You Out

Sarah and Lucy Feminize You and Breezy You Out

TrannyGem 3 years ago

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

aShemaleTube 3 months ago

女装OLアナル調教(1/4)

女装OLアナル調教(1/4)

TrannyGem 3 years ago

Viky & Master Private Show

58% HD 2:00 / 14:49

Viky & Master Private Show

Flirt4Free 5 months ago

AB105 Christmas Girl's Bondage Party-squiting cumshot

AB105 Christmas Girl's Bondage Party-squiting cumshot

xHamster 2 years ago

Nanny instructing Day

Nanny instructing Day

TransTube.tv 1 week ago

Turning the Straight you into a GAY sissy Cumslut

Turning the Straight you into a GAY sissy Cumslut

TransTube.tv 1 year ago

Compilation Sissy Training Super Huge!

Compilation Sissy Training Super Huge!

xHamster 1 year ago

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