Training Videos - Trans (86,613)

Indian Crossdresser Gaurisissy Feeling Horny in Purple Saree Looking and Fucking Like a Housewife

Indian Crossdresser Gaurisissy Feeling Horny in Purple Saree Looking and Fucking Like a Housewife

xHamster 11 months ago

Mouth fucking a deepthroated sissy bitch while watching porn

Mouth fucking a deepthroated sissy bitch while watching porn

xHamster 4 years ago

Osa Lovely Private Show

Osa Lovely Private Show

Flirt4Free 3 years ago

Mistress Training CD Foot Slave Chinese Femdom Chinese

Mistress Training CD Foot Slave Chinese Femdom Chinese

FetishShrine 1 year ago

Two hot leggings asses! Tranny girls fucking instead of a workout!

Two hot leggings asses! Tranny girls fucking instead of a workout!

xHamster 11 months ago

Goddess Tangent FemDom Strap-on Training

Goddess Tangent FemDom Strap-on Training

AbTranny 5 years ago

Sex Training

52% 4K 0:30 / 13:20

Futanari 3 years ago

Lesbian Shemale Making Love in Japanese College Uniform

63% 1:01 / 35:44

Lesbian Shemale Making Love in Japanese College Uniform

FapHouse 10 months ago

Master & Ithan & Aleex Private Show

41% HD 2:00 / 33:20

Master & Ithan & Aleex Private Show

Flirt4Free 6 months ago

TGIRLSHOOKUP: Bella Bates Gapes And Fills Her Sissy Hole!

TGIRLSHOOKUP: Bella Bates Gapes And Fills Her Sissy Hole!

xHamster 2 years ago

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

FreePorn8 1 year ago

She's Going to Get Her Ass Fucked in the Kitchen

She's Going to Get Her Ass Fucked in the Kitchen

xHamster 6 months ago

Cute femboy in cow bikini takes a big black dildo

HD 1:01 / 17:59

Cute femboy in cow bikini takes a big black dildo

FapHouse 2 years ago

Lisa Flirty Private Show

HD 2:00 / 17:33

Lisa Flirty Private Show

Flirt4Free 3 years ago

Bottom bitch Faggot! Dress up!

Bottom bitch Faggot! Dress up!

xHamster 1 month 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

Sissy rosebud teaching

Sissy rosebud teaching

TrannyGem 3 years ago

Alicia Akbar Private Show

HD 2:00 / 25:27

Alicia Akbar Private Show

Flirt4Free 3 years ago

Milf Breeder - part 3 - Gloryhole With A Massive Dick by Foxie2K

Milf Breeder - part 3 - Gloryhole With A Massive Dick by Foxie2K

xHamster 5 months ago

Glazing Her Lil' Inverted Pearl In Sissy Juices

Glazing Her Lil' Inverted Pearl In Sissy Juices

TrannyGem 1 year ago

White girl gets trained to lick black pussy

White girl gets trained to lick black pussy

Ebony8 7 years ago

MISTRESS DRILLER TRAINING HER PUPPY’s PUSSY

MISTRESS DRILLER TRAINING HER PUPPY’s PUSSY

aShemaleTube 3 years ago

G074 - Lr Creampie 4 (just the Tip)

G074 - Lr Creampie 4 (just the Tip)

FapHouse 5 months ago

Sissy Challenge

58% HD 0:10 / 5:14

Sissy Challenge

LoyalFans 3 years ago

Trans Damsel Enjoys Railing

Trans Damsel Enjoys Railing

Gayhaus 2 months ago

Imagine You Are Fucking a Boy!

Imagine You Are Fucking a Boy!

xHamster 2 months ago

Enormous black trouser snake plumbing sissy hoe Lola Crystals

Enormous black trouser snake plumbing sissy hoe Lola Crystals

TrannyGem 3 years ago

Sissy Trainer - Sissy - Feminization - Sissification

Sissy Trainer - Sissy - Feminization - Sissification

TrannyGem 3 years ago

Just me having pleasure ^^=

Just me having pleasure ^^=

ShemaleSin 1 week ago

Grubby String on fake penis Bum to Mouth Sissy Slut Gets Pegged and Humiliated by Latex Goddess Domme Mercer

Grubby String on fake penis Bum to Mouth Sissy Slut Gets Pegged and Humiliated by Latex Goddess Domme Mercer

TransTube.tv 1 year ago

Luke Hardy & Cristian Ford Party on Jan 16, 2026 - Part 3

57% 4K 2:00 / 1:55:10

Luke Hardy & Cristian Ford Party on Jan 16, 2026 - Part 3

Flirt4Free 2 weeks ago

Trans on a Fuckmachine for Her Neighbor

Trans on a Fuckmachine for Her Neighbor

xHamster 4 months ago

Osa Lovely Private Show

Osa Lovely Private Show

Flirt4Free 3 years ago

Builder job at work anal stimulating BDSM public

Builder job at work anal stimulating BDSM public

xHamster 6 months ago

oiled braceface BBC anal ballbusting and chastity cum

61% 4K 0:12 / 11:12

oiled braceface BBC anal ballbusting and chastity cum

Clips4sale 10 months ago

nude pathetic white thrall during outdoor party entertain guests, got enema, ejaculation, sex toy in homosexual booty, CMNM

nude pathetic white thrall during outdoor party entertain guests, got enema, ejaculation, sex toy in homosexual booty, CMNM

SortPorn 1 month ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 8 months ago

Direct Training by the Trainer No.31: Vibrator Play Feels so Good

Direct Training by the Trainer No.31: Vibrator Play Feels so Good

xHamster 1 month ago

I'm Man in Nice Lady's Figure 💌

I'm Man in Nice Lady's Figure 💌

WebcamBros 4 months ago

Treat Me Like a Sissy-slut

66% HD 0:39 / 18:39

Treat Me Like a Sissy-slut

FapHouse 2 months ago

charlotte sins jade venus zariah aura victoria grant lesbian in training

charlotte sins jade venus zariah aura victoria grant lesbian in training

PornOne 1 month ago

FULL VIDEO Lena Vesper Railed By Hankeys Seahorse Fuck Machine

FULL VIDEO Lena Vesper Railed By Hankeys Seahorse Fuck Machine

Pornzona 1 week ago

”Trans mistress Emma Rose trains mommy”

”Trans mistress Emma Rose trains mommy”

TransHero 2 years ago

Good morning, yoga class with handsome trainer

HD 1:01 / 22:32

Good morning, yoga class with handsome trainer

FapHouse 3 years ago

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

xHamster 2 years ago

barely legal twunk attempt his anal invasion to sqiurt and squealing for the very first time

barely legal twunk attempt his anal invasion to sqiurt and squealing for the very first time

Gayhub 6 months ago

Dominant Blk Trans w/ 11” inches BIG BLACK COCK Bully Dallas Vixen Controlling The Tramps

Dominant Blk Trans w/ 11” inches BIG BLACK COCK Bully Dallas Vixen Controlling The Tramps

TransTube.tv 1 year ago

Latex Mistress Verbally Humiliates and Strapons Rubber Sissy Doll. Arya Grander

Latex Mistress Verbally Humiliates and Strapons Rubber Sissy Doll. Arya Grander

xHamster 3 months ago

Gym training

AbTranny 6 years ago

Jessy Reed TS

62% HD 0:39 / 36:35

FapHouse 6 months ago

AB104 Sex toy tester surrender (English subtitles)

AB104 Sex toy tester surrender (English subtitles)

xHamster 2 years ago

”TGIRLS.XXX - Boss Hoe Training”

”TGIRLS.XXX - Boss Hoe Training”

StarWank 8 months ago

Pissing on Own Mouth and Face It and Wash Face with Piss

68% HD 1:01 / 8:47

Pissing on Own Mouth and Face It and Wash Face with Piss

FapHouse 1 year ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 14

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 14

xHamster 1 year ago

Sissy Enema Submission

63% HD 0:39 / 33:16

Sissy Enema Submission

FapHouse 1 year ago

AB105 Christmas Girl's Bondage Party-squiting cumshot

AB105 Christmas Girl's Bondage Party-squiting cumshot

xHamster 2 years ago

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

65% HD 0:39 / 13:39

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

FapHouse 1 year ago

Ftm Pegging

xHamster 3 weeks ago

hung oiled tgirl pumps her huge cock and shoots lots of cum

66% 4K 0:14 / 9:25

hung oiled tgirl pumps her huge cock and shoots lots of cum

Clips4sale 6 months ago

Play with My Pet Evolved Fights

61% 0:39 / 11:25

Play with My Pet Evolved Fights

FapHouse 2 months 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 3 years ago

Mature Mistress fucks a girl slave here male slave must watch her

Mature Mistress fucks a girl slave here male slave must watch her

12Milf 1 year ago

Japanese tranny shamelessly faps in motel lobby

Japanese tranny shamelessly faps in motel lobby

TrannyGem 2 years ago

AB085 Lustful Abby Kitty be Master's sissy slave -chastity 堕落成为主人的淫荡人妖锁奴母狗

AB085 Lustful Abby Kitty be Master's sissy slave -chastity 堕落成为主人的淫荡人妖锁奴母狗

aShemaleTube 2 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

Hot Trans Girl Tutor Trains You

Hot Trans Girl Tutor Trains You

xHamster 8 months ago

Asshole Stretching Good Time!!

Asshole Stretching Good Time!!

xHamster 1 month ago

”Those are five nasty creampies!”

”Those are five nasty creampies!”

TransHero 1 month ago

Marily Daniela Private Show

60% HD 2:00 / 16:16

Marily Daniela Private Show

Flirt4Free 2 years ago

FemGape Creamy Big Anal Training With Dildo

FemGape Creamy Big Anal Training With Dildo

TubeOn 1 week ago

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

4K 0:11 / 33:28

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

Clips4sale 5 days ago

”TGIRLS.XXX - Boss Hoe Training”

”TGIRLS.XXX - Boss Hoe Training”

Trashreality 6 months ago

Humiliating Cock Sucking Training for Sissy

Humiliating Cock Sucking Training for Sissy

Tranny.one 4 years ago

Crossdressing gay torn up in the bootie

Crossdressing gay torn up in the bootie

TrannyGem 7 months ago

Fucking your trans best friend surprise

52% HD 1:01 / 9:35

Fucking your trans best friend surprise

FapHouse 2 years ago

Huge ass tranny gaping

Huge ass tranny gaping

xHamster 1 year ago

TS Dominated and Assfucked by Mistress - TS Bimbo Pet Training with Sasha de Sade

TS Dominated and Assfucked by Mistress - TS Bimbo Pet Training with Sasha de Sade

aShemaleTube 6 years ago

Complete Cute Blonde Tgirl Lactating Her Tits and Punishing Her Puffy Nipples with a Vacuum Pump

HD 0:39 / 15:39

Complete Cute Blonde Tgirl Lactating Her Tits and Punishing Her Puffy Nipples with a Vacuum Pump

FapHouse 1 month ago

Master Trainer's Personal Training No. 30: Outdoor Restraint Vibrator Training

Master Trainer's Personal Training No. 30: Outdoor Restraint Vibrator Training

xHamster 1 month ago

◆ 3D FUTA Beauty’s First Time Turns Into Intense Pleasure as Toys & Big Cock Bring Her to Orgasm

◆ 3D FUTA Beauty’s First Time Turns Into Intense Pleasure as Toys & Big Cock Bring Her to Orgasm

SleazyNEasy 3 days ago

Marily Daniela Private Show

63% HD 2:00 / 19:59

Marily Daniela Private Show

Flirt4Free 2 years ago

”Emma's ballet training pays off as Ryan goes balls deep, hitting her beaver just right with his jizz.”

”Emma's ballet training pays off as Ryan goes balls deep, hitting her beaver just right with his jizz.”

TransHero 1 month ago

Sarah and Lucy Feminize You and Mega-breezy You Out

Sarah and Lucy Feminize You and Mega-breezy You Out

TransTube.tv 1 year ago

Julia Molligan Sissy Training In Red Dress JOI

Julia Molligan Sissy Training In Red Dress JOI

VipTube 1 week ago

Do You Like to See a Shredded and Muscular Body ?

51% HD 2:00 / 13:57

Do You Like to See a Shredded and Muscular Body ?

Flirt4Free 3 years ago

Elias & Elix Private Show

52% HD 2:00 / 16:27

Elias & Elix Private Show

Flirt4Free 5 months ago

A Bullied Girl Who Gets Creampie Training Teachers Who Know Students' Weaknesses

53% HD 1:01 / 37:36

A Bullied Girl Who Gets Creampie Training Teachers Who Know Students' Weaknesses

FapHouse 1 year ago

AB135 Excited nun in heat

AB135 Excited nun in heat

ShemaleSin 1 year ago

Super Hot transgender princess with good-sized bosoms romps in rear end

Super Hot transgender princess with good-sized bosoms romps in rear end

TrannyGem 2 weeks ago

Strapon on the way home from the cinema

Strapon on the way home from the cinema

xHamster 1 year ago

Double Stuffed w Girl Cock feat Ava Venom & Giselle Driller

74% 0:25 / 12:06

Double Stuffed w Girl Cock feat Ava Venom & Giselle Driller

Clips4sale 7 months ago

Skinny trans girl with pig tails has butt sex in locker room

HD 1:01 / 23:18

Skinny trans girl with pig tails has butt sex in locker room

FapHouse 5 years ago

Anal gape complications

Anal gape complications

xHamster 1 month ago

korean femboy kimono nailed

korean femboy kimono nailed

Gayhub 11 months ago

My Hotwife Gameplay - Part 6 - the Book of Cuckolding

My Hotwife Gameplay - Part 6 - the Book of Cuckolding

xHamster 3 months ago

korean slim femboy drilled (utter movie on fansly)

korean slim femboy drilled (utter movie on fansly)

Gayhub 11 months ago

”BRAZZERS My Fucking Crazy Cosplay GF - Natalie Brooke, Luna Baby, Seth Gamble”

”BRAZZERS My Fucking Crazy Cosplay GF - Natalie Brooke, Luna Baby, Seth Gamble”

TransHero 1 month ago

Small Trans Kawaii Fiona Screws a Compliant Trans Puppy-Beauty

Small Trans Kawaii Fiona Screws a Compliant Trans Puppy-Beauty

ShemaleSin 1 year ago

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

TrannyGem 4 years ago

Trans? Sissy? Both? Sissification Female domination Autogynaphillia AGP POINT OF VIEW Grubby Chat Femboy Instructing Jerk Off Instructions

Trans? Sissy? Both? Sissification Female domination Autogynaphillia AGP POINT OF VIEW Grubby Chat Femboy Instructing Jerk Off Instructions

TransTube.tv 1 year ago

Polska trans Compilation training to be good sissy slut. Trenuje by zostać posłuszną suką

Polska trans Compilation training to be good sissy slut. Trenuje by zostać posłuszną suką

aShemaleTube 7 months ago

Sissy, feminized, femboy, Chastity

Sissy, feminized, femboy, Chastity

ShemaleSin 2 weeks ago

Blowjob and Cumkiss for Sissy Husband

Blowjob and Cumkiss for Sissy Husband

xHamster 1 year ago

Slutty Students Accident Turns To BBC Fuck 😨 Look up my skirt!! Student LOVES To suck and fuck Uni Classmate's HUGE BBC 😈

57% HD 0:10 / 12:51

Slutty Students Accident Turns To BBC Fuck 😨 Look up my skirt!! Student LOVES To suck and fuck Uni Classmate's HUGE BBC 😈

LoyalFans 7 months ago

Self Facial Cumshot spunking from super-steamy sissy

Self Facial Cumshot spunking from super-steamy sissy

TrannyGem 3 years ago

Review: Chastity Cages for Sissies

Review: Chastity Cages for Sissies

xHamster 3 months ago

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass

xHamster 2 months ago

Mrs Horsecock Pt.3

Mrs Horsecock Pt.3

Hentaied.Pro 6 months ago

Periodentraining f&uuml_r Sissybitches von Domina Lady Julina

Periodentraining f&uuml_r Sissybitches von Domina Lady Julina

XVideos 3 years ago

Trix Bell Private Show

61% 4K 2:00 / 10:54

Trix Bell Private Show

Flirt4Free 5 months ago

Long machine fuck for bi slut with huge fake tits

Long machine fuck for bi slut with huge fake tits

xHamster 2 years ago

Turning My Boyfriend Into A Sissy Slut

Turning My Boyfriend Into A Sissy Slut

Pornzona 3 weeks ago

Bubble butt dildo training

Bubble butt dildo training

aShemaleTube 1 year ago

Sissy Kanisa Is Playing with Her Pussy

63% HD 1:01 / 9:46

Sissy Kanisa Is Playing with Her Pussy

FapHouse 8 months ago

Girth with XXXL Atlas

Girth with XXXL Atlas

xHamster 3 months ago

Door To Door - Cassie Cummings And Sinn Sage WMV

68% 0:22 / 35:55

Door To Door - Cassie Cummings And Sinn Sage WMV

Clips4sale 3 years ago

Doggy style sissy training in a red dress and white pumps

Doggy style sissy training in a red dress and white pumps

xHamster 2 years ago

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

TrannyGem 1 year ago

The first female orgasm - sissy behavior training with the lady of feminization Lady Julina

The first female orgasm - sissy behavior training with the lady of feminization Lady Julina

Pornzona 2 months ago

Take off Your Panties and Take Them All in Your Mouth.

Take off Your Panties and Take Them All in Your Mouth.

xHamster 2 months ago

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