Training Videos - Trans (117,466)

P2 FETISHTRANSEXUAL WITH HER NEW TOY BOI FUCKING HIM IN STRAIT JACKET CLOSE UP

65% HD 0:21 / 10:10

P2 FETISHTRANSEXUAL WITH HER NEW TOY BOI FUCKING HIM IN STRAIT JACKET CLOSE UP

Clips4sale 1 year ago

My sissy knows that every day she must come and suck my feet to make me rest after the gym.

My sissy knows that every day she must come and suck my feet to make me rest after the gym.

xHamster 2 years ago

Jessica Bloom Takes Fist And Foot Up Her Slutty Asshole Until She Cums Anal Fisting And Footing

Jessica Bloom Takes Fist And Foot Up Her Slutty Asshole Until She Cums Anal Fisting And Footing

xHamster 1 year ago

Sissy Playing With A Black Dildo

Sissy Playing With A Black Dildo

xHamster 1 year ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19

xHamster 5 months ago

Cock And Cum Slut For Mel Fire (MP4)

Cock And Cum Slut For Mel Fire (MP4)

Clips4sale 11 months ago

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

xHamster 1 year ago

Shemale Cock The****-Fantasy

66% HD 0:21 / 11:03

Shemale Cock The****-Fantasy

IWantClips 1 week ago

Your Therapist Marissa Sweet Mesmerizes You Into Becoming A Cock Sucking Crossdresser

Your Therapist Marissa Sweet Mesmerizes You Into Becoming A Cock Sucking Crossdresser

Pornzona 1 month ago

German Crossdress Babe Melinda James

German Crossdress Babe Melinda James

xHamster 3 months ago

Trans Marily Daniela Trains Billiards, Giant Arse, Smallish Manmeat, Rock-hard Anal invasion, Rubber []

Trans Marily Daniela Trains Billiards, Giant Arse, Smallish Manmeat, Rock-hard Anal invasion, Rubber []

KeekAss 1 month ago

Vocaloid Cosplayers in striped maid outfit anal training with long dildo part 3(4k Remaster)

Vocaloid Cosplayers in striped maid outfit anal training with long dildo part 3(4k Remaster)

aShemaleTube 11 months ago

The Boy's Word Remake NOCAP

The Boy's Word Remake NOCAP

aShemaleTube 5 months ago

Baseball Training

69% 1:01 / 12:03

Baseball Training

FapHouse 1 month ago

Huge Ass Shemale Caulifla Ssj Massive Anal Creampies and Cumfarts After Being Fucked by Big Dildo

HD 1:01 / 27:25

Huge Ass Shemale Caulifla Ssj Massive Anal Creampies and Cumfarts After Being Fucked by Big Dildo

FapHouse 2 weeks ago

Bound Orgasms and Anal in Sundresses and Ropes Ft Aerie Rei

Bound Orgasms and Anal in Sundresses and Ropes Ft Aerie Rei

xHamster 1 month ago

Trans Slut Gets Fucked By Mistress Until She Squirts Cum Into Own Mouth

Trans Slut Gets Fucked By Mistress Until She Squirts Cum Into Own Mouth

xHamster 7 months ago

Sophia Loreen Private Show

56% HD 2:00 / 9:58

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Turning into a human sex toy for my mistress's pleasure

Turning into a human sex toy for my mistress's pleasure

xHamster 11 months ago

Jasmine_dlight & Mistress Luciana - VR Shoulder Deep Anal Fisting & Gape

65% VR 0:08 / 2:19

Jasmine_dlight & Mistress Luciana - VR Shoulder Deep Anal Fisting & Gape

FapHouse 3 months ago

Part 1 Sunday Humiliation for Sissy husband

Part 1 Sunday Humiliation for Sissy husband

xHamster 1 year ago

Sissy crossdresser // Observe my rectal getting off and plow me

Sissy crossdresser // Observe my rectal getting off and plow me

TrannyGem 1 year ago

Rite of Passage for Real Sissies

Rite of Passage for Real Sissies

ShemaleSin 2 weeks ago

Zapping and buzzing the Dragon tattoo sissy Charlotte

Zapping and buzzing the Dragon tattoo sissy Charlotte

xHamster 10 months ago

French Cuckold Wife and Lesbian Anal Sissy

44% 1:01 / 5:08

French Cuckold Wife and Lesbian Anal Sissy

FapHouse 2 years ago

Shady Spa - Victoria Shiatsu Massage Therapist

46% HD 1:01 / 15:12

Shady Spa - Victoria Shiatsu Massage Therapist

FapHouse 1 year ago

Trans Demon Punishes You with Her Huge Dick and Massive Load of Hot Cum

HD 0:39 / 25:52

Trans Demon Punishes You with Her Huge Dick and Massive Load of Hot Cum

FapHouse 1 month ago

Columbian Boys Wedgie War

54% HD 2:00 / 15:54

Columbian Boys Wedgie War

Flirt4Free 9 months ago

Destroy My Hole

Destroy My Hole

xHamster 3 months ago

Carnal Sissy Anal Fisting - Unfathomable Gape and Prolapse Training

Carnal Sissy Anal Fisting - Unfathomable Gape and Prolapse Training

ShemaleSin 1 week ago

Sophia Loreen Private Show

72% 4K 2:00 / 13:07

Sophia Loreen Private Show

Flirt4Free 7 months ago

Sissy Kanisa in Sexy Purple Nightwear Ep1

Sissy Kanisa in Sexy Purple Nightwear Ep1

xHamster 5 months ago

Sissy Slave Is Riding on a Huge Dido

Sissy Slave Is Riding on a Huge Dido

FapHouse 7 months ago

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

61% HD 0:39 / 22:20

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

FapHouse 3 months ago

Pt.3 Deepthroat Toy - Training Slut

Pt.3 Deepthroat Toy - Training Slut

xHamster 8 months 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 11 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

Fuck Pussy

65% 4K 2:00 / 29:58

Flirt4Free 5 months ago

Relent to Your Trans Mistress

Relent to Your Trans Mistress

xHamster 2 months 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

Sissy cross dresser pegging compilation 🍆

Sissy cross dresser pegging compilation 🍆

xHamster 1 year ago

Sissy Jizzes with Emasculation Dog Collar on -Elastrator Have Fun

Sissy Jizzes with Emasculation Dog Collar on -Elastrator Have Fun

TrannyGem 3 years ago

Bizarre Anal Training of cute sissy locked in flat metal Chastity Cage riding large BBC sex-toy!

Bizarre Anal Training of cute sissy locked in flat metal Chastity Cage riding large BBC sex-toy!

ShemaleSin 7 months ago

Sissy 80 day chastity cum

Sissy 80 day chastity cum

xHamster 5 years ago

TS Lola Crystals (TrulyByL) bouncing on BIG BLACK COCK

TS Lola Crystals (TrulyByL) bouncing on BIG BLACK COCK

TransTube.tv 1 year ago

Bukkake Training for Two Tranny Sluts

Bukkake Training for Two Tranny Sluts

aShemaleTube 7 years ago

Trans Latina Teen Loses Virginity

58% 1:01 / 14:55

Trans Latina Teen Loses Virginity

FapHouse 4 months ago

Being a Hotty is Greater amount Pleasure! Sissy Feminization T-Hotty Training POV Femdom by Dominant-bitch Kyaa

Being a Hotty is Greater amount Pleasure! Sissy Feminization T-Hotty Training POV Femdom by Dominant-bitch Kyaa

ShemaleSin 3 months ago

Sissy Juvia does some encouraging Sissyfication Training JOI

Sissy Juvia does some encouraging Sissyfication Training JOI

xHamster 3 years ago

fastened up transgirl with oral machine and vibrating plug struggles to focus on game

fastened up transgirl with oral machine and vibrating plug struggles to focus on game

ShemaleSin 2 months ago

Sophia Loreen Private Show

61% HD 2:00 / 12:04

Sophia Loreen Private Show

Flirt4Free 4 years ago

'Jessica Bloom's Mind-Blowing Compilation of Self-Sucking and Sissygasm'

'Jessica Bloom's Mind-Blowing Compilation of Self-Sucking and Sissygasm'

Jizzberry 2 years ago

Serving Mistress

Serving Mistress

xHamster 4 months ago

Gender Transformations: Magic Makes You a Free Use Big Tit Bimbo Whore and Me a Big Cock Futa

47% HD 0:39 / 8:08

Gender Transformations: Magic Makes You a Free Use Big Tit Bimbo Whore and Me a Big Cock Futa

FapHouse 2 months ago

Pay Back Your Debt

Pay Back Your Debt

ShemaleSin 2 months ago

Sophia Loreen Private Show

HD 2:00 / 43:05

Sophia Loreen Private Show

Flirt4Free 1 month ago

Step-Daddy Kyaa's Dick

59% HD 0:10 / 10:58

Step-Daddy Kyaa's Dick

LoyalFans 2 years ago

Jogging with a Full Bladder! Great Tranny Wetting with a Huge Beam Straight Down!

66% HD 1:01 / 5:59

Jogging with a Full Bladder! Great Tranny Wetting with a Huge Beam Straight Down!

FapHouse 5 months ago

Girly Sissy Bitch! Jes Brinch Is a Weak Loser!

Girly Sissy Bitch! Jes Brinch Is a Weak Loser!

xHamster 2 months ago

Alexxa A Private Show

63% HD 2:00 / 8:27

Alexxa A Private Show

Camster 4 days ago

Special: Bloopers and Deleted Scenes of Anal Gaped Femboy in Cosplay Fucking His Ass and Jerking off Until She Cums

HD 0:39 / 14:00

Special: Bloopers and Deleted Scenes of Anal Gaped Femboy in Cosplay Fucking His Ass and Jerking off Until She Cums

FapHouse 3 weeks ago

Anal: big fake penis Training

Anal: big fake penis Training

Transvids.tv 1 day ago

Using your ass like a pussy

HD 1:01 / 20:25

Using your ass like a pussy

FapHouse 5 years ago

Sissy GOING KNUCKLE DEEP! Mitt puppet!

Sissy GOING KNUCKLE DEEP! Mitt puppet!

TransTube.tv 1 year ago

Matt & Oliver & Andres Private Show

53% HD 2:00 / 7:43

Matt & Oliver & Andres Private Show

Flirt4Free 3 years ago

Anal Training Night

Anal Training Night

xHamster 11 months ago

Sissy therapist HollyLou

Sissy therapist HollyLou

xHamster 1 month ago

AB071 Sissy tranining and pumping out(tickle,cable on ,Ruined Climax,S/M Jizz-shotgun-head responsibility)

AB071 Sissy tranining and pumping out(tickle,cable on ,Ruined Climax,S/M Jizz-shotgun-head responsibility)

TransTube.tv 1 year ago

8K - OCEX - Dark Egyptian Queen

55% 4K 0:23 / 29:39

8K - OCEX - Dark Egyptian Queen

Clips4sale 10 months ago

Crossdresser in High Heels Gets Anal Pussy Machine Fucked

Crossdresser in High Heels Gets Anal Pussy Machine Fucked

xHamster 11 months ago

He Fists His Trans Neighbor

64% 0:39 / 17:34

He Fists His Trans Neighbor

FapHouse 9 months ago

Horny Latin Boys

Horny Latin Boys

Flirt4Free 3 weeks ago

Nightshade Defeats Superman

Nightshade Defeats Superman

FapHouse 5 months ago

Fucked Outside Serving as an Ass to Mouth Slut in Sissy Clothes with Cumshot

Fucked Outside Serving as an Ass to Mouth Slut in Sissy Clothes with Cumshot

FapHouse 1 week 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

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

xHamster 2 years ago

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

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

xHamster 2 weeks ago

Bang My Fat Femboy Ass!

55% 0:39 / 8:33

Bang My Fat Femboy Ass!

FapHouse 3 weeks ago

Sissykanisa Crossdresser Play with Inflatable Anal Plug and Pinky Cock Cage

Sissykanisa Crossdresser Play with Inflatable Anal Plug and Pinky Cock Cage

xHamster 1 year ago

Doggy Training Part 2

Doggy Training Part 2

xHamster 1 year ago

Group of Guys Having Fun

54% HD 2:00 / 25:47

Group of Guys Having Fun

Flirt4Free 8 years ago

First-time Experience as a Submissive Sissy

First-time Experience as a Submissive Sissy

xHamster 1 week ago

TRANS GIRL ON HER KNEES: Cleaning Tigh-High Boots For Ebony MahoganyQen

65% HD 0:26 / 14:00

TRANS GIRL ON HER KNEES: Cleaning Tigh-High Boots For Ebony MahoganyQen

Clips4sale 7 months ago

Very Hot at the Campsite

Very Hot at the Campsite

FapHouse 1 day ago

teenie femboy attempting for sissygasm then gigantic popshot

teenie femboy attempting for sissygasm then gigantic popshot

TrannyGem 4 years ago

Sophia Loreen Party on Jun 18, 2026 - Part 4

HD 2:00 / 58:05

Sophia Loreen Party on Jun 18, 2026 - Part 4

Flirt4Free 1 week 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

Your Goddess Desires Ass Worship. A sure way to Earn your Place!

Your Goddess Desires Ass Worship. A sure way to Earn your Place!

TrannyGem 5 years ago

Sissy In Blue Riding Her Dildos

Sissy In Blue Riding Her Dildos

xHamster 5 months ago

Watch this if you're GAY

60% 1:01 / 11:20

Watch this if you're GAY

FapHouse 3 years ago

Warming up with Big warmup dildo in sexy PVC

Warming up with Big warmup dildo in sexy PVC

xHamster 1 week ago

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

AbTranny 5 years ago

feminisation training xhG8IAC

feminisation training xhG8IAC

FetishShrine 2 weeks ago

Double Stuffed w Girl Cock feat Ava Venom & Giselle Driller

76% 0:25 / 12:06

Double Stuffed w Girl Cock feat Ava Venom & Giselle Driller

Clips4sale 1 year ago

Sophia Loreen Private Show

61% HD 2:00 / 38:25

Sophia Loreen Private Show

Flirt4Free 5 days ago

Elias & Elix Private Show

43% HD 2:00 / 13:09

Elias & Elix Private Show

Flirt4Free 10 months ago

My First Handjob to a Stranger - Sissy Dream

46% HD 1:01 / 9:23

My First Handjob to a Stranger - Sissy Dream

FapHouse 1 year ago

Brutus K Private Show

57% HD 2:00 / 6:01

Brutus K Private Show

Flirt4Free 9 years ago

Sissy breezy pulverizes Domina on top

Sissy breezy pulverizes Domina on top

2BGay 2 years ago

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

65% HD 1:01 / 9:37

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

FapHouse 1 year ago

[ASMR] Positive Sissy Reinforcement- Audio Only

65% HD 0:30 / 12:03

[ASMR] Positive Sissy Reinforcement- Audio Only

IWantClips 1 year ago

Miad has to gobble jism facialed food

Miad has to gobble jism facialed food

TrannyGem 2 years ago

Sissy Hope is really horny, gets fucked by a huge dildo and rubs her little clitty with vibrator.

Sissy Hope is really horny, gets fucked by a huge dildo and rubs her little clitty with vibrator.

xHamster 4 years ago

Femboy Sissy Slut Sucking Dldo Hoping for a Real Dick to Lick

Femboy Sissy Slut Sucking Dldo Hoping for a Real Dick to Lick

FapHouse 2 weeks ago

Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails

Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails

xHamster 1 year ago

Sissy riding dildo in escort appartment

Sissy riding dildo in escort appartment

GayJaVu 9 months ago

Collared Tgirl Gets Attitude Adjustment

HD 1:01 / 16:05

Collared Tgirl Gets Attitude Adjustment

FapHouse 1 week ago

Sapphire Dresses You in Her Uniform

57% HD 0:39 / 10:54

Sapphire Dresses You in Her Uniform

FapHouse 8 months ago

Teen T-girl College Screw Anal SEX TRANS CUTIE cums trans porn

Teen T-girl College Screw Anal SEX TRANS CUTIE cums trans porn

Amateur8 9 months ago

Sissy Whiteboy takes 8 inch BBC dildo balls-deep

Sissy Whiteboy takes 8 inch BBC dildo balls-deep

xHamster 3 years ago

I came home from the gym sweaty, I came in my socks, licked all my cum and swallowed it all.

I came home from the gym sweaty, I came in my socks, licked all my cum and swallowed it all.

xHamster 2 years ago

caged goth sissy fucks herself with huge BBC leaks and cums

66% 4K 0:18 / 9:34

caged goth sissy fucks herself with huge BBC leaks and cums

Clips4sale 1 year ago

Pledge and get spot for my group show..start now!!

64% HD 2:00 / 19:52

Pledge and get spot for my group show..start now!!

Flirt4Free 6 years 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

HER FIRST REAL BBC PT 2 *HD 1080*

65% HD 0:10 / 15:26

HER FIRST REAL BBC PT 2 *HD 1080*

LoyalFans 3 years ago

Mistress Thursday and her sissy boy play the role of femboy for their horny mommy

Mistress Thursday and her sissy boy play the role of femboy for their horny mommy

Deviants 3 weeks ago

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

xHamster 1 year ago

I Love BBC! Fuck My Asspussy Deep and Rough!

I Love BBC! Fuck My Asspussy Deep and Rough!

xHamster 2 months ago

The Sissygasm

xHamster 1 year ago

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

65% HD 0:39 / 30:56

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

FapHouse 6 months ago

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