Training Videos - Trans (117,548)

Cam Crest Gets his Cunt Trained by Sindy Memo

Cam Crest Gets his Cunt Trained by Sindy Memo

aShemaleTube 1 year ago

Woman Encourages Guy Transformation Makeover into Woman

Woman Encourages Guy Transformation Makeover into Woman

xHamster 1 year ago

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

65% HD 1:01 / 26:52

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

FapHouse 2 years ago

feminisation training

feminisation training

ShemaleSin 5 months ago

STRAIGHT GUYS LOVE SHEMALES - ENCOURAGED BI

55% HD 0:10 / 25:08

STRAIGHT GUYS LOVE SHEMALES - ENCOURAGED BI

LoyalFans 8 months ago

Hole Training

Eporner 1 year ago

Sissy femboy bi-atch Pleasing monster gigantic dark-hued lollipop and servicing him fellate and kissing giant dark-hued pipe passionately

Sissy femboy bi-atch Pleasing monster gigantic dark-hued lollipop and servicing him fellate and kissing giant dark-hued pipe passionately

2BGay 2 years ago

trans sissy instructing delicate satin guts wanking screwing, finger-banging, and jerking

trans sissy instructing delicate satin guts wanking screwing, finger-banging, and jerking

TransTube.tv 1 year ago

She Trains Her Sissy Friend to Receive Cocks

She Trains Her Sissy Friend to Receive Cocks

FapHouse 1 year ago

Train

xHamster 8 years ago

Kendall Penny Gives Throat Training

Kendall Penny Gives Throat Training

Nuvid 4 months ago

Cataphase of my pleasure.

Cataphase of my pleasure.

xHamster 5 months ago

Ultimate Sissy Fuck Doll Trainer

55% HD 1:01 / 7:05

Ultimate Sissy Fuck Doll Trainer

FapHouse 5 months ago

Pissing on my cute femboy GF Hayley

Pissing on my cute femboy GF Hayley

xHamster 8 months ago

Charlie Cano Private Show

58% HD 2:00 / 7:16

Charlie Cano Private Show

Flirt4Free 3 years ago

Long intense machine fuck for crossdresser anal cunt

Long intense machine fuck for crossdresser anal cunt

xHamster 9 months ago

Playtime 69

xHamster 9 months ago

Sissy In A Green Bikini Riding A Black Dildo

Sissy In A Green Bikini Riding A Black Dildo

xHamster 1 year ago

Crossdresser Fucks Her Sissy Ass with Huge Toys

55% HD 1:01 / 16:50

Crossdresser Fucks Her Sissy Ass with Huge Toys

FapHouse 1 month ago

Advanced Anal Stretching with Jasmine-Dlight: Part 4 - Miss Hannah Blake Joins The Training

Premium HD 16:44

Advanced Anal Stretching with Jasmine-Dlight: Part 4 - Miss Hannah Blake Joins The Training

xnxxGold 7 months ago

Time to Submit Sissy

60% 1:01 / 13:18

Time to Submit Sissy

FapHouse 2 weeks ago

Sissy Riding a Large Anal Toy

Sissy Riding a Large Anal Toy

FapHouse 7 months ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

xHamster 2 months ago

Daniel Schmidt Private Show

55% 4K 2:00 / 13:29

Daniel Schmidt Private Show

Flirt4Free 4 weeks ago

Sophia Loreen Party on May 13, 2026 - Part 3

HD 2:00 / 34:53

Sophia Loreen Party on May 13, 2026 - Part 3

Flirt4Free 1 month ago

Bukkake Training for Two Tranny Sluts

Bukkake Training for Two Tranny Sluts

aShemaleTube 7 years ago

Wife Sissifies You - Sissy Training with Rebelle Hart

50% 0:25 / 16:59

Wife Sissifies You - Sissy Training with Rebelle Hart

Clips4sale 1 year ago

Sissy Feminization (wmv)

Sissy Feminization (wmv)

Clips4sale 10 months ago

Susan is playing with Cameron's bum

Susan is playing with Cameron's bum

TransTube.tv 1 year ago

Femdom Humiliation Sissy Training My Maid

57% HD 1:01 / 12:37

Femdom Humiliation Sissy Training My Maid

FapHouse 2 months ago

Emmy Angeles Will Receive Facesitting, Breast Pain, CBT in a Bondage Toilet Chair

HD 0:39 / 15:08

Emmy Angeles Will Receive Facesitting, Breast Pain, CBT in a Bondage Toilet Chair

FapHouse 1 month ago

Chantal Sweet Lets the Jordan Hung Dildo Pound Hard in Her Ass on the Sex Machine

59% HD 1:01 / 5:18

Chantal Sweet Lets the Jordan Hung Dildo Pound Hard in Her Ass on the Sex Machine

FapHouse 2 months ago

Ryan Boness & Eduar Senni Private Show

55% HD 2:00 / 6:55

Ryan Boness & Eduar Senni Private Show

Flirt4Free 4 days ago

Cum-and-pee Drink For a Sexy Tranny With a Fisted And Zucchini-stretched Anus

Cum-and-pee Drink For a Sexy Tranny With a Fisted And Zucchini-stretched Anus

Tranny.one 2 years ago

Giving My Juicy Rosebud Some Attention, It Wants to Grow, Become a Huge Prolapse, Falling From My Wrecked Asscunt

Giving My Juicy Rosebud Some Attention, It Wants to Grow, Become a Huge Prolapse, Falling From My Wrecked Asscunt

FapHouse 1 month ago

Rachael Belle In ass-fuck Trainer

Rachael Belle In ass-fuck Trainer

TransTube.tv 9 months ago

Double Anal Prolapse Making Sissy Girl Asshole Lose

Double Anal Prolapse Making Sissy Girl Asshole Lose

xHamster 3 months ago

Let's Jerk off Together JOI

56% HD 0:39 / 11:51

Let's Jerk off Together JOI

FapHouse 4 months ago

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

HD 0:39 / 23:31

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

FapHouse 5 months ago

Checking Locked Dick and Strapon

Checking Locked Dick and Strapon

xHamster 2 years ago

Mistress fingering and giving prostate massage to her Sissy

Mistress fingering and giving prostate massage to her Sissy

xHamster 5 months ago

Femboy fists gaping ass with gloves, rides big dildo and jerks big cock to cumshot

Femboy fists gaping ass with gloves, rides big dildo and jerks big cock to cumshot

xHamster 1 year ago

Submissive male slave pegged by his dominating mistress

Submissive male slave pegged by his dominating mistress

XGroovy 2 years ago

Sissy caged fucking her ass with BBC

Sissy caged fucking her ass with BBC

xHamster 1 year ago

Melting Homo - Sissification Training Teaser

Melting Homo - Sissification Training Teaser

ShemaleSin 1 month ago

Anastasia Mistress female Domination homemade strapon sissy amateur

Anastasia Mistress female Domination homemade strapon sissy amateur

xHamster 2 months ago

Isabel Moon Training Day Extra

Isabel Moon Training Day Extra

Eporner 4 months ago

Dildo Distracted

76% 1:01 / 10:11

Dildo Distracted

FapHouse 1 year ago

Long machine for worn out crossdresser anal

Long machine for worn out crossdresser anal

xHamster 1 year ago

【汚デブ女装肉便器】ド変態★淫乱ダイジェスト【女装マゾ】【みけぽ】【GMPD】【精液便所】【性奴隷】【調教】【乳首ピアス】【露出】

【汚デブ女装肉便器】ド変態★淫乱ダイジェスト【女装マゾ】【みけぽ】【GMPD】【精液便所】【性奴隷】【調教】【乳首ピアス】【露出】

TrannyGem 2 years ago

Shemale slut training in sexy lingerie and stockings

Shemale slut training in sexy lingerie and stockings

xHamster 4 years ago

Sissy Enema Submission

63% HD 0:39 / 33:16

Sissy Enema Submission

FapHouse 2 years ago

Deep Sissy Fisting

57% HD 0:39 / 3:16

Deep Sissy Fisting

FapHouse 1 year ago

Sissy Cable-On Pegging Spitroast by Dual Dominatrixes Domina Mercer and Coral

Sissy Cable-On Pegging Spitroast by Dual Dominatrixes Domina Mercer and Coral

TrannyGem 4 years ago

G083 - Blowjob 14, deepthroat Frenzy

HD 1:01 / 38:16

G083 - Blowjob 14, deepthroat Frenzy

FapHouse 8 months ago

Jaquelin Braxton fucking after training

Jaquelin Braxton fucking after training

AbTranny 7 years ago

Unexpected sissy boy orgasm .

Unexpected sissy boy orgasm .

xHamster 2 months ago

SISSY TRAINING Amateur Crossdresser Anal Dildo Big Black Dildo Riding

SISSY TRAINING Amateur Crossdresser Anal Dildo Big Black Dildo Riding

aShemaleTube 2 years ago

Slut Training Part 1

Slut Training Part 1

xHamster 2 years ago

Sissy GOING KNUCKLE DEEP! Mitt puppet!

Sissy GOING KNUCKLE DEEP! Mitt puppet!

TransTube.tv 1 year ago

Reality Porn Theatre

65% 0:39 / 53:42

Reality Porn Theatre

FapHouse 3 months ago

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

AbTranny 5 years ago

COCK IN A FROCK 7 - + EXTRAS

COCK IN A FROCK 7 - + EXTRAS

Pornzona 6 days ago

Crossdresser Sissy Chastity Sex

61% 1:01 / 14:45

Crossdresser Sissy Chastity Sex

FapHouse 1 month ago

Whiteboi Bitch Jes!

Whiteboi Bitch Jes!

xHamster 1 day ago

He Slowly Became a Very Good Girl

He Slowly Became a Very Good Girl

FapHouse 11 months ago

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

xHamster 7 months ago

T-Girl tugging and screaming

T-Girl tugging and screaming

TrannyGem 3 years ago

Rite of Passage for Real Sissies

Rite of Passage for Real Sissies

ShemaleSin 2 weeks ago

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

TrannyGem 4 years ago

Sophie Fantasy Private Show

Sophie Fantasy Private Show

Flirt4Free 1 month ago

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

HD 1:01 / 15:12

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

FapHouse 6 days ago

Hot Trans Girl Tutor Trains You

55% HD 0:39 / 41:53

Hot Trans Girl Tutor Trains You

FapHouse 1 year ago

Tranny Gives JOI and CEI While Making Laundry! Stop & Go! Pre-cum Licking! Ruined Orgasm!

49% HD 1:01 / 6:34

Tranny Gives JOI and CEI While Making Laundry! Stop & Go! Pre-cum Licking! Ruined Orgasm!

FapHouse 4 months ago

SPECIAL: Fat ass Femboy Cumfarting Anal Creampie after being Gaped and Fucked by Black Dildo

SPECIAL: Fat ass Femboy Cumfarting Anal Creampie after being Gaped and Fucked by Black Dildo

xHamster 1 month ago

Matsumine Kohaku - Deepthroat Training! Massive Swallowing! a Perverted Circle of Trans Lovers.

55% HD 0:39 / 22:33

Matsumine Kohaku - Deepthroat Training! Massive Swallowing! a Perverted Circle of Trans Lovers.

FapHouse 5 months ago

Our Anniversary Show Free Hands Cumshot!!! the Best

HD 0:39 / 12:34

Our Anniversary Show Free Hands Cumshot!!! the Best

FapHouse 1 week 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

SisK being fucked by fucking machine

SisK being fucked by fucking machine

xHamster 3 years ago

Sissy Trained And Owned By Big Black Penis Bull With Sasha Desade

Sissy Trained And Owned By Big Black Penis Bull With Sasha Desade

AbTranny 3 years ago

All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody

All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody

xHamster 1 year ago

Trannies in training - (Episode #05)

Trannies in training - (Episode #05)

xHamster 1 month ago

Simon & Juseph & Alejandro Private Show

56% HD 2:00 / 1:02:40

Simon & Juseph & Alejandro Private Show

Flirt4Free 2 years ago

Puppy Play Slave. Sniff Master's Balls and Feet.

HD 1:01 / 14:53

Puppy Play Slave. Sniff Master's Balls and Feet.

FapHouse 5 days ago

Luna Florez Private Show

Luna Florez Private Show

Camster 1 day ago

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

62% HD 0:39 / 3:07

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

FapHouse 1 year ago

Sissy Slut Fuck Doll Takes Anal Fisting, Pegging & Fuck Machine with HUGE DILDO Hardcore Femdom Porn!

Sissy Slut Fuck Doll Takes Anal Fisting, Pegging & Fuck Machine with HUGE DILDO Hardcore Femdom Porn!

xHamster 10 months ago

Sasha De Sade's BDSM training ends in a hot and heavy humiliation session

Sasha De Sade's BDSM training ends in a hot and heavy humiliation session

TrannyMovs 6 months ago

weekly anal workout for crossdresser DWT slut

weekly anal workout for crossdresser DWT slut

xHamster 1 year ago

Anal Training 105

HD 0:39 / 43:37

Anal Training 105

FapHouse 2 days ago

New Violet Dildo for My Sissy Bitch

New Violet Dildo for My Sissy Bitch

xHamster 1 year ago

Orianna Dunn Private Show

46% HD 2:00 / 4:33

Orianna Dunn Private Show

Flirt4Free 2 years ago

Happy Birthday Lola

65% HD 1:01 / 28:52

Happy Birthday Lola

FapHouse 2 months ago

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

62% HD 0:35 / 20:42

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

PissVids 1 year ago

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

66% HD 0:39 / 9:57

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

FapHouse 9 months ago

Emery Lune Anal Solo Play Vol Ii

67% HD 1:01 / 44:06

Emery Lune Anal Solo Play Vol Ii

FapHouse 1 month ago

Whorish Femboy Maid in Innocence Takes Harsh Assfucking Teaching ~oscar20xxx~

Whorish Femboy Maid in Innocence Takes Harsh Assfucking Teaching ~oscar20xxx~

GayCK 6 years ago

She Gonna Have to Learn How to Become a Good Girl

62% 0:39 / 7:02

She Gonna Have to Learn How to Become a Good Girl

FapHouse 1 year ago

Tranny Tease And Pantyhose Footjob (MP4)

54% HD 0:13 / 12:12

Tranny Tease And Pantyhose Footjob (MP4)

Clips4sale 4 years ago

Drivers class ends with a hard anal - Finn Harding , Amanda Riley

Drivers class ends with a hard anal - Finn Harding , Amanda Riley

Fapnado 3 years ago

The Krystal Swift Experience

The Krystal Swift Experience

Some.Porn 1 year ago

POINT OF VIEW-Trans gf attempts to get him to stop dinking around with her girlfriend- inhale-job and plumbed

POINT OF VIEW-Trans gf attempts to get him to stop dinking around with her girlfriend- inhale-job and plumbed

Transvids.tv 11 months ago

Pretty Femboy Bitch Serving Cocks

52% 1:01 / 7:22

Pretty Femboy Bitch Serving Cocks

FapHouse 1 month ago

Zapping and buzzing the Dragon tattoo sissy Charlotte

Zapping and buzzing the Dragon tattoo sissy Charlotte

xHamster 10 months ago

I'm so happy to get a butt plug in my sissy pussy.

I'm so happy to get a butt plug in my sissy pussy.

xHamster 2 years ago

Sissy Faggot Cocksucker JOI

55% HD 0:25 / 18:16

Sissy Faggot Cocksucker JOI

Clips4sale 2 years ago

Warning on Chastity Pt. 2

78% HD 1:01 / 7:25

Warning on Chastity Pt. 2

FapHouse 1 year ago

River Enza dominates and punishes her sissy with hardcore rough sex and face cumshots

River Enza dominates and punishes her sissy with hardcore rough sex and face cumshots

TrannyMovs 2 weeks ago

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

58% HD 0:39 / 5:12

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

FapHouse 2 months ago

Mistress Plays with Her Futanari Dolls

52% 1:01 / 41:16

Mistress Plays with Her Futanari Dolls

FapHouse 1 year ago

The Future of Maya Luxx Is to Be a Trans Sex Toy

57% 0:39 / 21:57

The Future of Maya Luxx Is to Be a Trans Sex Toy

FapHouse 3 months ago

Ballbusting Testicular Percussion Massage

Ballbusting Testicular Percussion Massage

xHamster 1 year ago

Fucking my buttplug and gaping my sissy hole

Fucking my buttplug and gaping my sissy hole

xHamster 3 years ago

Sissy Wife Eats Her Cum Out of Her Panties - Clara Dee JOI

Sissy Wife Eats Her Cum Out of Her Panties - Clara Dee JOI

xHamster 2 years ago

Biggest Clear Sextoy screws my butt cunt making me gape #anal #artporn 4K

Biggest Clear Sextoy screws my butt cunt making me gape #anal #artporn 4K

ShemaleSin 3 weeks ago

Sissy Training by Queen Daralis Part 3

56% HD 0:39 / 9:18

Sissy Training by Queen Daralis Part 3

FapHouse 4 months ago

French amateur doggy training

French amateur doggy training

xHamster 2 years ago

Sophia Loreen Private Show

63% HD 2:00 / 4:42

Sophia Loreen Private Show

Flirt4Free 4 weeks ago

Bimbo Sexy Trans Transformation

Bimbo Sexy Trans Transformation

xHamster 11 months ago

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

59% 0:39 / 14:02

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

FapHouse 2 years ago

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