Training Videos - Trans (117,246)

Chastity Sissy Throat Training And Plapping Orgasm - Huge Cum Squirt And Swallow Jessica Blooom

Chastity Sissy Throat Training And Plapping Orgasm - Huge Cum Squirt And Swallow Jessica Blooom

xHamster 1 year ago

Spun Sissy very first Web Cam Showcase Recorded

Spun Sissy very first Web Cam Showcase Recorded

TrannyGem 6 years ago

Blonde mistress humiliating with balls kicking her slave boy

Blonde mistress humiliating with balls kicking her slave boy

Tranny.one 4 years ago

centaur things 3 - (amy s big wish 3-3) - a futanari deertaur gets trained in the art of breeding!

62% 0:29 / 9:40

centaur things 3 - (amy s big wish 3-3) - a futanari deertaur gets trained in the art of breeding!

PornBox 2 months ago

Zara Clark Private Show

HD 2:00 / 10:34

Zara Clark Private Show

Flirt4Free 1 month ago

On-the-job Training: Shemale hentai Jenny Cums A Biggest Load in My Throat Beneath Coffee Counter

On-the-job Training: Shemale hentai Jenny Cums A Biggest Load in My Throat Beneath Coffee Counter

ShemaleSin 8 months ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Apr 25, 2026 - Part 3

63% HD 2:00 / 1:00:50

Sophia Loreen Party on Apr 25, 2026 - Part 3

Flirt4Free 1 month ago

Patric & Alexander & Lian Private Show

46% HD 2:00 / 33:17

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

kingnoirexxx - emma rose ts at kings altar

kingnoirexxx - emma rose ts at kings altar

TransDoe 2 years ago

FIST TIME IN THE ASS!!!!

Premium HD 19:16

FIST TIME IN THE ASS!!!!

XVideosRed 1 year ago

Bastian Maalouf Private Show

HD 2:00 / 25:12

Bastian Maalouf Private Show

Flirt4Free 3 years ago

Premature Handsfree Sissygasm - Cumshot in 30 Seconds!

Premature Handsfree Sissygasm - Cumshot in 30 Seconds!

Pornzona 3 months ago

Submissive Skinny Ladyboy Anal Casting & Slave Training

HD 1:01 / 28:53

Submissive Skinny Ladyboy Anal Casting & Slave Training

FapHouse 5 months ago

Hattabi4ik Super Hot Monstrous Caboose Gold Rain And Jizz Shot

Hattabi4ik Super Hot Monstrous Caboose Gold Rain And Jizz Shot

TrannyGem 7 months ago

White cross dresser bbc gangbang training

White cross dresser bbc gangbang training

SexTubeSpot 6 years ago

Surviving 24 Hours As The Beach Sex Slave

Surviving 24 Hours As The Beach Sex Slave

Pornzona 3 months ago

Naked Uncut Muscle Hunk Shows Off

66% HD 2:00 / 7:37

Naked Uncut Muscle Hunk Shows Off

Flirt4Free 9 years ago

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Pornzona 1 month ago

Cuck, His BBC makes my Tummy Bulge - 4K

55% 4K 0:27 / 15:44

Cuck, His BBC makes my Tummy Bulge - 4K

Clips4sale 1 year ago

Jolting convulsions while a sissy boy pleasures himself

Jolting convulsions while a sissy boy pleasures himself

JuicyTrans 1 day ago

Emo Femboy gets bred by BIG BLACK DICK

Emo Femboy gets bred by BIG BLACK DICK

MyTransfix 1 month ago

Bastian Maalouf Private Show

Bastian Maalouf Private Show

Flirt4Free 3 years ago

Lance & Christian & Master Private Show

63% HD 2:00 / 13:19

Lance & Christian & Master Private Show

Flirt4Free 3 years ago

Femboy ladyboy anal chair destroyed while riding dildo rough hardcore

Femboy ladyboy anal chair destroyed while riding dildo rough hardcore

JuicyTrans 2 weeks ago

Cumslut Training by Futa Mistress: Assplay, Cei, and JOI

Cumslut Training by Futa Mistress: Assplay, Cei, and JOI

Jizzberry 3 years ago

Latino Foursome Having Fun

61% HD 2:00 / 9:54

Latino Foursome Having Fun

Flirt4Free 8 years ago

White Sissy’s Throat DESTROYED by Uncut Trans BBC cum Load

White Sissy’s Throat DESTROYED by Uncut Trans BBC cum Load

JuicyTrans 2 weeks ago

BBC Sissy Lola Destroyed Gaping on 10in Black Beast

BBC Sissy Lola Destroyed Gaping on 10in Black Beast

JuicyTrans 3 days ago

Fucking The Teacher

Fucking The Teacher

Some.Porn 7 months ago

Perseo & Dafne Private Show

62% HD 2:00 / 11:27

Perseo & Dafne Private Show

Flirt4Free 1 year ago

Master & Ithan Private Show

43% HD 2:00 / 12:09

Master & Ithan Private Show

Flirt4Free 11 months ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 9 months ago

Enjoy my nude body and my round ass bouncing in a good dildo! lets cum together! - Part 2

Enjoy my nude body and my round ass bouncing in a good dildo! lets cum together! - Part 2

Flirt4Free 11 months ago

Anna Guisx Private Show

Anna Guisx Private Show

Flirt4Free 4 years ago

SHEMALE HUMILIATION

59% HD 0:27 / 10:24

SHEMALE HUMILIATION

Clips4sale 10 months ago

Three Femdom Cocks, One Fuck Doll Slut

53% HD 0:10 / 11:13

Three Femdom Cocks, One Fuck Doll Slut

LoyalFans 2 years ago

Ambar Collins Private Show - Part 2

HD 2:00 / 19:44

Ambar Collins Private Show - Part 2

Flirt4Free 1 year ago

Leyla Steel Private Show

65% 4K 2:00 / 33:05

Leyla Steel Private Show

Flirt4Free 11 months ago

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Pornfact 3 weeks ago

Ruby Astrom Private Show

Ruby Astrom Private Show

Flirt4Free 4 months ago

Ada Valentine fisting and huge toy play

Ada Valentine fisting and huge toy play

xHamster 3 months ago

Joe Body Private Show

Joe Body Private Show

Flirt4Free 4 weeks ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 month ago

Two sissy femboys wrecked HARD gangbang creampie anal threesome

Two sissy femboys wrecked HARD gangbang creampie anal threesome

JuicyTrans 2 days ago

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

xHamster 2 years ago

Sissy slave fuck and piss comp.

Sissy slave fuck and piss comp.

xHamster 1 year ago

Gabriella Bruni Private Show

Gabriella Bruni Private Show

Flirt4Free 10 months ago

Bastian Maalouf Private Show

Bastian Maalouf Private Show

Flirt4Free 3 years ago

Naughty Sissy and the lucky slave

Naughty Sissy and the lucky slave

Clips4sale 4 years ago

The Herta's Training

The Herta's Training

ShemaleSin 2 weeks ago

Latex Dehumanization and Training a Human Sex Doll

Latex Dehumanization and Training a Human Sex Doll

xHamster 9 months ago

Elvis & Alfonso & Master Private Show

63% HD 2:00 / 10:47

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

Pornzona 3 months ago

Femboy instructing part 1: The Back Arch

Femboy instructing part 1: The Back Arch

2BGay 2 years ago

Two doms encourage you to explore your bisexual side by sucking cock - Jaq Quicksilver and Sydney Screams - FtM Jaq and BBW Sydney coach you through your first blowjob while you jerk off - joi, bi, handjob, threesome, dirty talk - 720p mp4

65% HD 0:29 / 11:27

Two doms encourage you to explore your bisexual side by sucking cock - Jaq Quicksilver and Sydney Screams - FtM Jaq and BBW Sydney coach you through your first blowjob while you jerk off - joi, bi, handjob, threesome, dirty talk - 720p mp4

Clips4sale 1 year ago

BBC Transgender makes a Slut out of Tattooed White Stud

BBC Transgender makes a Slut out of Tattooed White Stud

ShemaleSin 5 years ago

Panty Sissy big toy anal gaping prolapse loose hole rosebud

Panty Sissy big toy anal gaping prolapse loose hole rosebud

xHamster 4 years ago

Trixie Mills Private Show

Trixie Mills Private Show

Flirt4Free 2 years ago

I make it for the first time with a cucumber anal 30CM

I make it for the first time with a cucumber anal 30CM

xHamster 5 months ago

Bryan is Pantied and Plugged

Bryan is Pantied and Plugged

Pornfact 2 weeks ago

Femboy training bussy on large sex toy~

Femboy training bussy on large sex toy~

ShemaleSin 11 months ago

Sissy caged fucking her ass with BBC

Sissy caged fucking her ass with BBC

xHamster 1 year ago

Anal Exam

61% HD 1:01 / 25:02

FapHouse 4 months ago

ryu Doll takes glowing Sinnovator  20in deep

ryu Doll takes glowing Sinnovator  20in deep

Pornzona 3 months ago

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

xHamster 1 year ago

Gabriella Bruni Private Show - Part 4

4K 2:00 / 23:50

Gabriella Bruni Private Show - Part 4

Flirt4Free 1 year ago

Rebeccah Gibson Private Show

HD 2:00 / 24:41

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

Sophia Loreen Private Show

HD 2:00 / 14:54

Sophia Loreen Private Show

Camster 2 years ago

Sissy attempting to get caught

Sissy attempting to get caught

TrannyGem 1 year ago

BBC Vs Clitty! Adreena Winters Mocks This Sissy Into Cock Sucking Submission

43% HD 0:39 / 3:25

BBC Vs Clitty! Adreena Winters Mocks This Sissy Into Cock Sucking Submission

FapHouse 6 months ago

Elix & Elias & Paulo Private Show

46% HD 2:00 / 11:00

Elix & Elias & Paulo Private Show

Flirt4Free 11 months ago

Miruplanttt Anal Training With Big Dildo

Miruplanttt Anal Training With Big Dildo

aShemaleTube 6 months ago

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

TrannyGem 4 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Luke Hardy & Cristian Ford Private Show

HD 2:00 / 29:53

Luke Hardy & Cristian Ford Private Show

Flirt4Free 5 months ago

Japanese trans star Julia Winston fucked hard

78% HD 1:01 / 25:05

Japanese trans star Julia Winston fucked hard

FapHouse 5 years ago

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION ROLEPLAY - AI GENERATED)

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster 1 year ago

Ubeer & Paulo Private Show

63% HD 2:00 / 8:13

Ubeer & Paulo Private Show

Flirt4Free 1 year ago

I Am Sissy in Manila Can't Resist Pinoy Trans

I Am Sissy in Manila Can't Resist Pinoy Trans

xHamster 1 year ago

Khalifa Gold & Lissa Hamilton Private Show

HD 2:00 / 13:01

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 10 months ago

Celeste Wembley Private Show

61% HD 2:00 / 4:59

Celeste Wembley Private Show

Flirt4Free 4 years ago

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

HD 0:26 / 10:05

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

Clips4sale 8 months ago

sissypov - ararity look how stiff i get when taking it up the ass porn video

sissypov - ararity look how stiff i get when taking it up the ass porn video

TransDoe 1 year ago

Fledgling Sissy Jizzes for First-Ever Time from Fleshlight

Fledgling Sissy Jizzes for First-Ever Time from Fleshlight

TrannyGem 2 years ago

SCIFI GENDER TRANSFORMATION FEMINIZATION BONDAGE SEX SLAVE

SCIFI GENDER TRANSFORMATION FEMINIZATION BONDAGE SEX SLAVE

Pornzona 2 weeks ago

Submissive Skinny Ladyboy Anal Casting & Slave Training

Submissive Skinny Ladyboy Anal Casting & Slave Training

xHamster 8 months ago

good-sized dark ten-Pounder Adore butt/bj Trainer Fo

good-sized dark ten-Pounder Adore butt/bj Trainer Fo

TransTube.tv 1 year ago

ryu Doll uses bad dragon on machine and monster can

ryu Doll uses bad dragon on machine and monster can

Pornzona 3 months ago

The Skewer Competition

68% 0:21 / 23:45

The Skewer Competition

Clips4sale 2 years ago

Dominatrix Sura penetrates her slave

70% HD 0:14 / 5:34

Dominatrix Sura penetrates her slave

Clips4sale 2 years ago

Trixie Mills Private Show

HD 2:00 / 25:51

Trixie Mills Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

HD 2:00 / 14:56

Sophia Loreen Private Show

Flirt4Free 3 years ago

Sissy In Chastity Anal Training With Njoy Wand

Sissy In Chastity Anal Training With Njoy Wand

PornUse 7 months ago

Sissy training you my slave, strap on and a sext Tranny, its yor dream, isnt it slave? ;) xx

70% 4K 0:50 / 24:39

Sissy training you my slave, strap on and a sext Tranny, its yor dream, isnt it slave? ;) xx

Clips4sale 1 month ago

Trixie Mills Private Show

Trixie Mills Private Show

Flirt4Free 2 years ago

Crossdresser gets rode by giant knob hump machine

Crossdresser gets rode by giant knob hump machine

TrannyGem 1 year ago

Trixie Mills Private Show

Trixie Mills Private Show

Flirt4Free 2 years ago

Military PolicePenis

Military PolicePenis

Some.Porn 1 year ago

FemDom Queen Cailey Katts and Dream Divyne Fuck Hard Rough Anal Sissy Training

FemDom Queen Cailey Katts and Dream Divyne Fuck Hard Rough Anal Sissy Training

JuicyTrans 1 week ago

Jade Venus, recently gave his office so hes had a private session

Jade Venus, recently gave his office so hes had a private session

Sheshaft 2 years ago

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

xHamster 1 year ago

Tits Out for Fitness

Tits Out for Fitness

Some.Porn 1 year ago

korean femboy kimono smashed

korean femboy kimono smashed

Gay4Porn 1 year ago

Sophia Loreen Party on Oct 31, 2025 - Part 2

54% 4K 2:00 / 6:28

Sophia Loreen Party on Oct 31, 2025 - Part 2

Flirt4Free 7 months ago

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

TrannyGem 7 months ago

Sissy feminization training for hot trans slut destroyed by femdom humiliation

Sissy feminization training for hot trans slut destroyed by femdom humiliation

JuicyTrans 2 weeks ago

Anal Invasion instructing with a ample, clear horsecock

Anal Invasion instructing with a ample, clear horsecock

TrannyGem 9 months ago

Khalifa Gold & Lissa Hamilton Private Show

66% HD 2:00 / 29:10

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 10 months ago

Anal Training Sissy Anal Orgasm Hands Free Guide

Anal Training Sissy Anal Orgasm Hands Free Guide

aShemaleTube 1 month ago

Training my tight transfem ass with a huge dildo until I’m gushing on cam

Training my tight transfem ass with a huge dildo until I’m gushing on cam

JuicyTrans 2 weeks ago

Pegged and Edged w Giselle Driller Ava Venom

72% 0:20 / 16:07

Pegged and Edged w Giselle Driller Ava Venom

Clips4sale 1 year ago

Chastity fag slave humiliation pet play bondage

Chastity fag slave humiliation pet play bondage

xHamster 5 months ago

Asian Trans Stroking and Cumming

HD 2:00 / 18:44

Asian Trans Stroking and Cumming

Flirt4Free 7 years ago

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Premium HD 33:02

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Sheer 1 year ago

Sissy femboy torn apart by monster dildos training session raw wrecked

Sissy femboy torn apart by monster dildos training session raw wrecked

GayPornWatch 2 weeks ago

Threesome Sissy Domination

HD 0:39 / 25:56

Threesome Sissy Domination

FapHouse 6 months ago

teenie femboy attempting for sissygasm then gigantic popshot

teenie femboy attempting for sissygasm then gigantic popshot

TrannyGem 4 years ago

Lisa Gets Destroyed By Charlotte In Sensory Deprivation Bondage

Lisa Gets Destroyed By Charlotte In Sensory Deprivation Bondage

JuicyTrans 2 weeks ago

Teen Sissy Already Knows Her Place

Teen Sissy Already Knows Her Place

xHamster 11 months ago

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