Training Videos - Trans (87,622)

Sasha's Dollhouse Angel & Sissy Training

Sasha's Dollhouse Angel & Sissy Training

ShemaleSin 4 years ago

Luke Hardy & Cristian Ford Private Show

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

The Well Used Hole @missavablack & @obeyladymk Use Jasmine Dlight's Bottomless Pit

57% HD 1:01 / 19:05

The Well Used Hole @missavablack & @obeyladymk Use Jasmine Dlight's Bottomless Pit

FapHouse 1 year ago

Glamour Girls Humiliation 257 wmv

Glamour Girls Humiliation 257 wmv

Clips4sale 11 months ago

MILF Fucked for Mistress

MILF Fucked for Mistress

Clips4sale 8 months ago

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 4 OF 6

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 4 OF 6

Clips4sale 2 months ago

No.113: a Crossdresser Being Trained in the Sunlit Spot

HD 1:01 / 11:06

No.113: a Crossdresser Being Trained in the Sunlit Spot

FapHouse 3 days ago

Il contratto di Sissy - The Sissy's slut contract #2 (PART 2) (MOBILE VERSION MP4)

57% HD 0:11 / 17:53

Il contratto di Sissy - The Sissy's slut contract #2 (PART 2) (MOBILE VERSION MP4)

Clips4sale 1 year ago

Cum slut training pt. 3 - pent up for you

HD 1:01 / 17:51

Cum slut training pt. 3 - pent up for you

FapHouse 5 years ago

FemDom Feminization- Dick Sucking Lips Enhancement

68% 0:31 / 5:09

FemDom Feminization- Dick Sucking Lips Enhancement

Clips4sale 2 years ago

Bad Slut needs more Training

Bad Slut needs more Training

TrannyGem 7 years ago

Brazzers Exxtra: Latina LaSirena69 ass to mouth

Brazzers Exxtra: Latina LaSirena69 ass to mouth

HDPornVideosTV 4 years ago

Trans PAWG trains her butt for a massive sex toy

Trans PAWG trains her butt for a massive sex toy

ShemaleSin 1 year ago

Sissy Trainer - Sissy - Feminization - Sissification

Sissy Trainer - Sissy - Feminization - Sissification

TrannyGem 3 years ago

Captured feminized latexed & enslaved

40% HD 0:30 / 8:57

Captured feminized latexed & enslaved

Clips4sale 1 year ago

MaureenNadh - Hijab Sissy Squirt While Anal Training Using Chastity Cage

MaureenNadh - Hijab Sissy Squirt While Anal Training Using Chastity Cage

xHamster 2 years ago

Mistress Lady Renee - Dressed to suck - mp4

57% 0:16 / 11:09

Mistress Lady Renee - Dressed to suck - mp4

Clips4sale 1 year ago

sissy maid has the best boipussy

65% 0:11 / 26:37

sissy maid has the best boipussy

Clips4sale 2 years ago

Sissified blowjob training MP4

HD 0:25 / 13:15

Sissified blowjob training MP4

Clips4sale 1 week ago

Feminization Fashion Show Training Part 2

HD 0:15 / 19:12

Feminization Fashion Show Training Part 2

Clips4sale 4 years ago

Pussy Free Sissy Pillow Humping JOI

49% HD 0:21 / 10:14

Pussy Free Sissy Pillow Humping JOI

Clips4sale 1 year ago

POINT OF VIEW Tgirl Trains Transgender Princess Pet how to Deepthroat Girlcock and Gulp Jizz

POINT OF VIEW Tgirl Trains Transgender Princess Pet how to Deepthroat Girlcock and Gulp Jizz

KeekAss 5 years ago

Sissy hubby stashing in Douche frolicking with a BIG BLACK COCK

Sissy hubby stashing in Douche frolicking with a BIG BLACK COCK

Gayhub 6 months ago

Extra skinny amateur Thai ladyboy teen Kitty training on her lovers BWC

Extra skinny amateur Thai ladyboy teen Kitty training on her lovers BWC

SleazyNEasy 1 week ago

POV Hard Pegging Jasmine Dlight From Mistress

73% HD 0:39 / 4:10

POV Hard Pegging Jasmine Dlight From Mistress

FapHouse 1 year ago

Mikes Hanon Private Show

HD 2:00 / 13:11

Mikes Hanon Private Show

Flirt4Free 5 years ago

Jessica Bloom Sucks Huge Trans Dick Swallows Two Loads of Cum

73% HD 1:01 / 10:17

Jessica Bloom Sucks Huge Trans Dick Swallows Two Loads of Cum

FapHouse 7 months ago

Leyla Steel Private Show

56% 4K 2:00 / 12:27

Leyla Steel Private Show

Flirt4Free 8 months ago

Sissy get fucked by sex maschine on table again.png

Premium HD 10:55

Sissy get fucked by sex maschine on table again.png

XVideosRed 8 months ago

When your sissy is missing parent's rod

When your sissy is missing parent's rod

TrannyGem 1 year ago

Pegging a Cute TS Whore 1080p ft Mistress Youko - trans strapon sissy

67% HD 0:30 / 17:40

Pegging a Cute TS Whore 1080p ft Mistress Youko - trans strapon sissy

Clips4sale 1 year ago

Hole Stretching, Spanking, and Wax Play w Mia &amp; Bia

Hole Stretching, Spanking, and Wax Play w Mia &amp; Bia

Clips4sale 2 years ago

Anal Creampie Workplace Harassment

Premium HD 37:13

Anal Creampie Workplace Harassment

Clips4sale 2 years ago

4K - Ichigo Femboy Pervert Panties Sucking + Cum Swallowing Play ~Ichigo x Strawberry Festival~

4K 0:18 / 18:09

4K - Ichigo Femboy Pervert Panties Sucking + Cum Swallowing Play ~Ichigo x Strawberry Festival~

Clips4sale 1 month ago

Ass To Mouth Sissy Training (MP4)

Ass To Mouth Sissy Training (MP4)

Clips4sale 1 year ago

Wear My Panties and Rub, Sissy Slut!

53% 0:10 / 10:15

Wear My Panties and Rub, Sissy Slut!

Clips4sale 1 year ago

Maid Into A Slut - Erica Cherry And Sinn Sage WMV

57% 0:20 / 31:42

Maid Into A Slut - Erica Cherry And Sinn Sage WMV

Clips4sale 3 years ago

Sophia Loreen Private Show

63% HD 2:00 / 10:58

Sophia Loreen Private Show

Flirt4Free 1 year ago

Anal Training #11

HD 1:01 / 19:35

Anal Training #11

FapHouse 1 year ago

8K UNMASKED - Koakuma Femboy Temptation Anus Side

8K UNMASKED - Koakuma Femboy Temptation Anus Side

Clips4sale 5 months ago

Duan Anal Training Topping Bareback

Duan Anal Training Topping Bareback

AbTranny 6 months ago

Sissy teasing and dildo riding on balcony

Sissy teasing and dildo riding on balcony

XVideos 6 months ago

Tori Anisston Private Show

Tori Anisston Private Show

Flirt4Free 3 years ago

Girldicks Are Bigger 2 : Small Penis Humiliation JOI POV Triple Domination Goth Girls

Premium 4K 10:10

Girldicks Are Bigger 2 : Small Penis Humiliation JOI POV Triple Domination Goth Girls

Clips4sale 8 months ago

Want to warm up this morning? (fire) JOIN the group and get a sexy show with my body, strip, spanks, twerk, and RIDE TOY... lets get wet and hot (yummy)

Want to warm up this morning? (fire) JOIN the group and get a sexy show with my body, strip, spanks, twerk, and RIDE TOY... lets get wet and hot (yummy)

Flirt4Free 1 year ago

”Goddess Kyaa & River Enza in Gape Training 3”

”Goddess Kyaa & River Enza in Gape Training 3”

Faptor 9 months ago

Cupcake Journey

43% HD 0:42 / 8:56

Cupcake Journey

Clips4sale 2 years ago

Sissygasm, Slut’s Caged Training, Massive Cumshots & Anal Milking – Jessica Bloom

Sissygasm, Slut’s Caged Training, Massive Cumshots & Anal Milking – Jessica Bloom

xHamster 3 years ago

Peter Is Wanking Over Lady Boys

Peter Is Wanking Over Lady Boys

FapHouse 1 year ago

Stepdaddy Wanted to See My Ass Open

Stepdaddy Wanted to See My Ass Open

FapHouse 9 months ago

Diabla Rivers & Rouse Morgan Private Show

63% HD 2:00 / 7:11

Diabla Rivers & Rouse Morgan Private Show

Flirt4Free 2 years ago

”Shemale aerobic trainer fucks blonde milf - Kenzie Taylor & Kayleigh Coxx”

”Shemale aerobic trainer fucks blonde milf - Kenzie Taylor & Kayleigh Coxx”

429Men 11 months ago

She Caught You Jerking to Cock – Now Her New Man Is Coming to Break You Forever

HD 0:30 / 39:17

She Caught You Jerking to Cock – Now Her New Man Is Coming to Break You Forever

Clips4sale 1 month ago

Addonis Smith & Huber Nicols Private Show

58% HD 2:00 / 32:11

Addonis Smith & Huber Nicols Private Show

Flirt4Free 1 year ago

YOUR NEW STEP-MOM IS A SHEMALE

57% HD 0:10 / 13:40

YOUR NEW STEP-MOM IS A SHEMALE

LoyalFans 8 months ago

Cum-Soaked Devotion: Serving My Divine Shemale BBC Pastors

Premium HD 12:28

Cum-Soaked Devotion: Serving My Divine Shemale BBC Pastors

Clips4sale 1 year ago

Sissy Slut Uses Cum as Lube and has Anal Sissygasms in Chastity Jessica Bloom

Sissy Slut Uses Cum as Lube and has Anal Sissygasms in Chastity Jessica Bloom

xHamster 6 months ago

FUTA CUSTOM 4 POV: I'm Making You Surrender

FUTA CUSTOM 4 POV: I'm Making You Surrender

Clips4sale 3 years ago

Futa Mistress Fucks Your Throat & Ass with CEI

65% 4K 0:30 / 11:46

Futa Mistress Fucks Your Throat & Ass with CEI

Clips4sale 2 months ago

Sissy Kanisa Play with Her Metal Anal Plug

Sissy Kanisa Play with Her Metal Anal Plug

FapHouse 1 week ago

Sissy Hole Training (Super Hot Anal Trainer) - AmberSis

Sissy Hole Training (Super Hot Anal Trainer) - AmberSis

BeMyHole 5 years ago

I Used to Think I was a Man

HD 0:29 / 11:42

I Used to Think I was a Man

Clips4sale 8 months ago

Ultimate Sissy Fuck Doll Trainer

Ultimate Sissy Fuck Doll Trainer

FapHouse 2 months ago

Rectal instructing

Rectal instructing

TrannyGem 4 months ago

Hot Submissive Tgirl Slut Hired to Take Down Dictation Pissed On Eat Ass Swallow Cum

60% HD 0:22 / 14:02

Hot Submissive Tgirl Slut Hired to Take Down Dictation Pissed On Eat Ass Swallow Cum

Clips4sale 1 year ago

bnwo ai training xhgzq5c

bnwo ai training xhgzq5c

FetishShrine 5 months ago

SISSY TRAP - XXL RECTAL FAKE PENISES GAME

SISSY TRAP - XXL RECTAL FAKE PENISES GAME

TrannyGem 3 years ago

Sophia Loreen Party on Mar 2, 2026 - Part 4

4K 2:00 / 39:17

Sophia Loreen Party on Mar 2, 2026 - Part 4

Flirt4Free 1 week ago

The Reward for the Locked-up Sissy

66% HD 0:39 / 12:56

The Reward for the Locked-up Sissy

FapHouse 3 months ago

Shemale Fucked Her Personal Trainer

HD 0:39 / 27:00

Shemale Fucked Her Personal Trainer

FapHouse 1 month ago

See me take this ample nine" node, Dire Cub silver silicon fuck stick

See me take this ample nine" node, Dire Cub silver silicon fuck stick

TrannyGem 2 years ago

Hottest Cock Milking Ever

55% HD 0:39 / 12:34

Hottest Cock Milking Ever

FapHouse 1 month ago

Flabby clitty in pants on the screwing machine

Flabby clitty in pants on the screwing machine

ShemaleSin 7 months ago

FISTING ANAL EM PUBLICO

FISTING ANAL EM PUBLICO

XVideos 6 months ago

Denim Girl

FapHouse 9 months ago

Sissy Having Fun on the Swing

Sissy Having Fun on the Swing

FapHouse 2 weeks ago

Two Dommes and the Delivery Boy - Throat Trained

63% HD 1:01 / 5:15

Two Dommes and the Delivery Boy - Throat Trained

FapHouse 1 year ago

Fat Dildo Stretches Skinny Femboy

Fat Dildo Stretches Skinny Femboy

FapHouse 1 week ago

HD Ziva Fey - Obedient Overalls Mesmerization FULL LENGTH

HD 0:30 / 1:08:38

HD Ziva Fey - Obedient Overalls Mesmerization FULL LENGTH

Clips4sale 4 months ago

Gorgeous transsexual Venus Lux fiercely bangs a hot young guy

Gorgeous transsexual Venus Lux fiercely bangs a hot young guy

Tranny.one 8 years ago

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 2 OF 6

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 2 OF 6

Clips4sale 2 months ago

Huge 9in Dildo Fucking Compilation Vol.5

Huge 9in Dildo Fucking Compilation Vol.5

xHamster 7 months ago

Sissy Slut Makeup Training Session

HD 0:10 / 31:34

Sissy Slut Makeup Training Session

LoyalFans 1 week ago

Sissy Shower Series - Cleansing Ritual

Premium HD 22:05

Sissy Shower Series - Cleansing Ritual

xnxxGold 2 years ago

Dungeon Doings w Goddess Cleo Jane

51% HD 0:56 / 13:04

Dungeon Doings w Goddess Cleo Jane

Clips4sale 1 year ago

Foot Worship With Ashley Vega

Foot Worship With Ashley Vega

Clips4sale 3 years ago

Brutus Private Show

61% HD 2:00 / 19:28

Brutus Private Show

Flirt4Free 3 years ago

Master & Christian Mckenzie & Christian Rey Private Show

61% HD 2:00 / 11:48

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Wifey Instructs Flawless Bi-Atch for her Hubby. Me, A Sissy.

Wifey Instructs Flawless Bi-Atch for her Hubby. Me, A Sissy.

TrannyGem 5 years ago

TURNED ON BY TRANNYS

TURNED ON BY TRANNYS

Clips4sale 2 years ago

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Propper Way

HD 1:01 / 48:52

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Propper Way

FapHouse 1 year ago

Straight men don't do things like you!

45% 0:11 / 8:42

Straight men don't do things like you!

Clips4sale 4 years ago

My friend Ts Girl Dani Marks humiliates my husband and has a Sissy

My friend Ts Girl Dani Marks humiliates my husband and has a Sissy

Clips4sale 1 year ago

Gay porn addiction programming mov

63% 0:11 / 6:07

Gay porn addiction programming mov

Clips4sale 2 years ago

Jasminedlight & Valentina Rosa - Outdoor Garden Extreme Anal Training Footing

65% HD 1:01 / 8:54

Jasminedlight & Valentina Rosa - Outdoor Garden Extreme Anal Training Footing

FapHouse 5 months ago

I put my entire hand up a trans woman&#039_s ass in public

I put my entire hand up a trans woman&#039_s ass in public

XVideos 3 months ago

BBC Training the Soggy Sissy: ThePrincessLuxy Reinforces and Threatens to Expose your True Place in the Sexual Heirarchy with Shemale Affirmations, Wet Diaper Humping, and Anal Preparation

HD 0:25 / 18:00

BBC Training the Soggy Sissy: ThePrincessLuxy Reinforces and Threatens to Expose your True Place in the Sexual Heirarchy with Shemale Affirmations, Wet Diaper Humping, and Anal Preparation

Clips4sale 1 month ago

Unexperienced Sissy breezy fellate that big black cock and got butt total rock hard poked

Unexperienced Sissy breezy fellate that big black cock and got butt total rock hard poked

Gayhub 9 months ago

I Woke up My Sissy and Fucked Her Hole with Fisting

HD 1:01 / 25:19

I Woke up My Sissy and Fucked Her Hole with Fisting

FapHouse 5 months ago

Sissy School (1080)

HD 0:21 / 10:04

Sissy School (1080)

Clips4sale 2 years ago

Playing with monster black dildo

Playing with monster black dildo

xHamster 2 years ago

Trans Femboy Solo Anal Masturbation Dildo

HD 1:01 / 13:16

Trans Femboy Solo Anal Masturbation Dildo

FapHouse 10 months ago

Sissy Slut Training Anal Pegging

Sissy Slut Training Anal Pegging

XVideos 4 years ago

Preparing Our Sissy For A Pounding!

45% 4K 0:11 / 11:30

Preparing Our Sissy For A Pounding!

Clips4sale 4 years ago

CHEAT WITH A SHEMALE

CHEAT WITH A SHEMALE

Clips4sale 8 months ago

Bustforcapri Anal Training With Dildo

Bustforcapri Anal Training With Dildo

VivaTube 1 month ago

Sissy School

Clips4sale 2 years ago

Stinging Tits, Thudding Ass: Femme Sandy Paddle & Clamp Session with Queen Elena

57% 0:39 / 3:09

Stinging Tits, Thudding Ass: Femme Sandy Paddle & Clamp Session with Queen Elena

FapHouse 1 month ago

Self-training No. 94: Wearing Sanitary Pads and Tampons for an Exposure Walk - Part 1

Self-training No. 94: Wearing Sanitary Pads and Tampons for an Exposure Walk - Part 1

FapHouse 3 weeks ago

Bottom bitch Jes fuck like a Girl

Bottom bitch Jes fuck like a Girl

xHamster 1 month ago

Deepthroat Training: Submission Takes Shape

Deepthroat Training: Submission Takes Shape

FapHouse 2 months ago

Il contratto da Sissy - The Sissy's slut contract #2 (MOBILE VERSION MP4)

58% HD 0:11 / 35:01

Il contratto da Sissy - The Sissy's slut contract #2 (MOBILE VERSION MP4)

Clips4sale 1 year ago

Nymph TEAR UP T-MODEL NUN compilation

Nymph TEAR UP T-MODEL NUN compilation

TransTube.tv 1 year ago

Good Girl Fucked, Bad Girl Cucked

68% HD 1:00 / 29:25

Good Girl Fucked, Bad Girl Cucked

Clips4sale 3 years ago

Bladder Training Time! 1.5 Liters made me cum!

Bladder Training Time! 1.5 Liters made me cum!

ShemaleSin 9 months ago

Angel Reina Hanno Stimulates Cream with Golden Butt Plug

66% HD 1:01 / 27:31

Angel Reina Hanno Stimulates Cream with Golden Butt Plug

FapHouse 3 months ago

Golden Rain. No Rights Day in Da House

Golden Rain. No Rights Day in Da House

FapHouse 1 year ago

Training Before New Year's Eve

Training Before New Year's Eve

FapHouse 2 weeks ago

ENCOURAGED BI FETISH Sissy Pantyhose Crossdressing Humiliation Trailer Compilation PREVIEWS

ENCOURAGED BI FETISH Sissy Pantyhose Crossdressing Humiliation Trailer Compilation PREVIEWS

Juicexxx 3 months ago

Pink Satin Maid Stretching Sissygasmsissy Maid Training

Pink Satin Maid Stretching Sissygasmsissy Maid Training

FapHouse 3 months ago

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