Training Videos - Trans (119,515)

Sexy Sissy Deep Anal Fisting!

Sexy Sissy Deep Anal Fisting!

Tranny.one 10 months ago

Ftm Pegging

XHamster 7 months ago

Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

XHamster 1 year ago

Sophia Loreen Party on Jul 31, 2026 - Part 3

HD 2:00 / 42:34

Sophia Loreen Party on Jul 31, 2026 - Part 3

Camster 2 weeks ago

fresh Pet Amber Shock acquires roped Up And caboose ravaged By Ciren Verde And Lora Cross

fresh Pet Amber Shock acquires roped Up And caboose ravaged By Ciren Verde And Lora Cross

TrannyGem 5 years ago

Saggy Tits Humiliation Dom Training Bra

57% HD 1:01 / 6:22

Saggy Tits Humiliation Dom Training Bra

FapHouse 1 year ago

Sissy Let out of Purity For Her Deep Urethral Sounding

Sissy Let out of Purity For Her Deep Urethral Sounding

TrannyGem 3 years ago

reward pegging for latex futa mommy's trained chastity submissive - full video on Veggiebabyy Manyvids

reward pegging for latex futa mommy's trained chastity submissive - full video on Veggiebabyy Manyvids

XHamster 10 months ago

Celeste & Liz Private Show

Celeste & Liz Private Show

Camster 3 years ago

Two Asses for Your Cock

59% 4K 2:00 / 5:05

Two Asses for Your Cock

Flirt4Free 1 year ago

Sissygasm for Domina

64% 0:39 / 4:11

Sissygasm for Domina

FapHouse 1 year ago

Jennifer Skanes Private Show

HD 2:00 / 19:02

Jennifer Skanes Private Show

Camster 1 month ago

Prego domme Is worshiped by her sissy after her ass-fuck instructing

Prego domme Is worshiped by her sissy after her ass-fuck instructing

TrannyGem 2 years 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 1 year ago

Instructions Anal Training

Instructions Anal Training

AShemaleTube 2 years ago

Side View Ritual - Peg Unlock Edge Slap Relock Denial

Side View Ritual - Peg Unlock Edge Slap Relock Denial

XHamster 5 months ago

Two creampies in one morning from two strangers! Filling up Sonya&#039;s hole in a rented apartment. Clip 1

Two creampies in one morning from two strangers! Filling up Sonya&#039;s hole in a rented apartment. Clip 1

XHamster 4 months ago

Sissy Strap-on Fucked by Asian Mistress Dominafire

Sissy Strap-on Fucked by Asian Mistress Dominafire

XHamster 5 months ago

FULL MOVIE The New Black Neighbor

41% HD 0:30 / 1:07:03

FULL MOVIE The New Black Neighbor

Clips4sale 1 year ago

Gaymer Workout

HD 0:29 / 21:31

Clips4sale 4 years ago

[ Full Version ] Serve My Ladyboy Friend 2 ft Mari Ayanami

58% HD 1:02 / 54:29

[ Full Version ] Serve My Ladyboy Friend 2 ft Mari Ayanami

IWantClips 2 months ago

Stepmom sex training

Stepmom sex training

XHamster 1 year ago

Luxurious reality

Luxurious reality

TrannyGem 4 years ago

Husband dressed up like a sissy bitch & pegged in his tight ass hole

Husband dressed up like a sissy bitch & pegged in his tight ass hole

XHamster 3 years ago

Sorority Girls StrapOn Hazing

60% HD 0:10 / 13:01

Sorority Girls StrapOn Hazing

LoyalFans 1 year ago

Lewd sissy CD slut anal training live stream - Unfathomable and massive anal toys inflatable screw machine smokin' corset satin

Lewd sissy CD slut anal training live stream - Unfathomable and massive anal toys inflatable screw machine smokin' corset satin

ShemaleSin 3 years ago

Beauty Shemale Anal Training Using Cucumber

Beauty Shemale Anal Training Using Cucumber

XHamster 4 years ago

A Supreme Dude Ejaculates in Your Donk The Hottest Dude Jizzes in Your

A Supreme Dude Ejaculates in Your Donk The Hottest Dude Jizzes in Your

Gayhub 11 months ago

Sophia Loreen Private Show

61% HD 2:00 / 4:23

Sophia Loreen Private Show

Camster 3 years ago

Suck Jessica Bloom's Trans Jock - Big Buttplug Training + Drink My Load Then Your Own CEI

Suck Jessica Bloom's Trans Jock - Big Buttplug Training + Drink My Load Then Your Own CEI

Lesbian8 3 months ago

First time Sissy MixyXXX training FIST with hands free orgasm!

First time Sissy MixyXXX training FIST with hands free orgasm!

AShemaleTube 2 years ago

Sophia Loreen Private Show

62% HD 2:00 / 31:53

Sophia Loreen Private Show

Flirt4Free 2 months ago

Sissy crossdresser bent over, humiliated & pegged

Sissy crossdresser bent over, humiliated & pegged

XHamster 1 year ago

SPOILT MUSLIM WIFE FOR A SISSY COCK

66% 0:11 / 20:48

SPOILT MUSLIM WIFE FOR A SISSY COCK

Clips4sale 3 years ago

Mistress Fingers Me in Gloves

Mistress Fingers Me in Gloves

FapHouse 1 week ago

Feminization : Your new Life as a Sissy Slave - Transformation - Ep4 I Turn a Compulsive Wanker into a Slave - Maitresse Julia

Feminization : Your new Life as a Sissy Slave - Transformation - Ep4 I Turn a Compulsive Wanker into a Slave - Maitresse Julia

XHamster 2 years ago

Alejandra Fox Private Show

63% HD 2:00 / 4:02

Alejandra Fox Private Show

Flirt4Free 3 years ago

Outdoor workout with vibrator for ass and cock! Tranny cums straight into her shorts!

72% HD 0:30 / 5:40

Outdoor workout with vibrator for ass and cock! Tranny cums straight into her shorts!

Clips4sale 1 year ago

Sissy Transformation: The Ultimate Step-by-Step Fuckin' Guide

Sissy Transformation: The Ultimate Step-by-Step Fuckin' Guide

XXXShake 2 years ago

Sissy training deepthroats cock with sloppy wet blowjob

Sissy training deepthroats cock with sloppy wet blowjob

AveXXX 1 month ago

get on your knees sissy

get on your knees sissy

ShemaleSin 1 year ago

hot teen trans in chastity gapes ass with BBC and farts cum

65% 4K 0:19 / 11:21

hot teen trans in chastity gapes ass with BBC and farts cum

Clips4sale 11 months ago

Honeypot Teaching

Honeypot Teaching

TrannyGem 5 years ago

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

60% HD 1:01 / 19:05

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

FapHouse 1 year ago

Sissy Lucy Anal Training In Chastity With Huge Dildos And Getting Pegged By Lisa

Sissy Lucy Anal Training In Chastity With Huge Dildos And Getting Pegged By Lisa

GetTranny 3 years ago

becomingfemme - clarice darling showing off her progression

becomingfemme - clarice darling showing off her progression

TransDoe 2 years ago

AB104 Fucky-fucky fucktoy tester give up (Japanese and English subtitles)

AB104 Fucky-fucky fucktoy tester give up (Japanese and English subtitles)

Transvids.tv 1 year ago

Office Training

Office Training

FreePorn8 4 years ago

TS Fetishista

50% HD 0:39 / 21:58

FapHouse 8 years ago

Bondage blowjob training

Bondage blowjob training

XHamster 3 months ago

Accomplishments in your Mistress's name [1080p, mp4]

71% HD 0:14 / 10:03

Accomplishments in your Mistress's name [1080p, mp4]

Clips4sale 3 years ago

Blind Date gone wrong - Sissy seduces a BBC

57% 0:11 / 20:06

Blind Date gone wrong - Sissy seduces a BBC

Clips4sale 2 years ago

POV Demon Futa Warps Your Subconscious to Worship Cock - Shapeshifting Giantess

POV Demon Futa Warps Your Subconscious to Worship Cock - Shapeshifting Giantess

XHamster 1 year ago

Extremes Sissy ANAL Training

Extremes Sissy ANAL Training

XHamster 1 year ago

Cheating wife fucks her personal trainer in the gym, cheating wife with gym trainer,gym sex,fitness sex,no protection sex,cum in

Cheating wife fucks her personal trainer in the gym, cheating wife with gym trainer,gym sex,fitness sex,no protection sex,cum in

XHamster 2 years ago

8K - OCEX - Dark Egyptian Queen

55% 4K 0:23 / 29:39

8K - OCEX - Dark Egyptian Queen

Clips4sale 1 year ago

Black Boy Got Turn on by His Coach at the Training Section

Black Boy Got Turn on by His Coach at the Training Section

XHamster 6 months ago

Sissy Trained And Owned By Big Black Penis Bull

Sissy Trained And Owned By Big Black Penis Bull

GetTranny 3 years ago

FISTING compilation 1.0 - Anuskatzz dominate her sissy whore anal SADOMASOCHISM fist

FISTING compilation 1.0 - Anuskatzz dominate her sissy whore anal SADOMASOCHISM fist

ShemaleSin 1 month ago

Egyptian Wife With Arab Shemale

Egyptian Wife With Arab Shemale

Tranny.one 3 years ago

This Was So Humiliating Mistressmurmur Gave Me Self Facial Training With Sasha Desade

This Was So Humiliating Mistressmurmur Gave Me Self Facial Training With Sasha Desade

AbTranny 2 months ago

Natalie Mars Helps Bestie Explore Anal Fantasies With Toys And Strap-On

Natalie Mars Helps Bestie Explore Anal Fantasies With Toys And Strap-On

Eporner 1 year ago

Cute Tgirl Variety Itsol gets her big butt plugged & anal trained with a chastity cage

Cute Tgirl Variety Itsol gets her big butt plugged & anal trained with a chastity cage

TrannyMovs 11 months ago

Aria Faye Anal Training With Big Dildo

Aria Faye Anal Training With Big Dildo

IcePorn 6 months ago

Suck Hole+dick

64% HD 2:00 / 19:43

Flirt4Free 2 years ago

The Truth About Your Waiters

The Truth About Your Waiters

Some.Porn 11 months ago

HD Trans Sissy Femboy Ballet Nearly 4K (2160x2160) Safe for Work

Premium 4K 10:40

HD Trans Sissy Femboy Ballet Nearly 4K (2160x2160) Safe for Work

XNXXGold 1 year ago

Solo Honeymoon Muscle Bitch

66% 1:01 / 13:05

Solo Honeymoon Muscle Bitch

FapHouse 11 months ago

The Grand Finale of Me Cumming Twice After Fucking My Sissy Pussy... It Felt so Damn Good...

The Grand Finale of Me Cumming Twice After Fucking My Sissy Pussy... It Felt so Damn Good...

FapHouse 2 years ago

Kinky Bitch - sissy training part 1

68% 4K 0:43 / 12:10

Kinky Bitch - sissy training part 1

Clips4sale 3 months ago

brace face trans teen sucks cock and deep throat while caged

68% 0:15 / 12:54

brace face trans teen sucks cock and deep throat while caged

Clips4sale 1 year ago

Latex Mistress Training Anal Sissy in Chastity

Latex Mistress Training Anal Sissy in Chastity

XHamster 2 years ago

becoming femme - riley jay being a hot blonde is so much fun porn video

becoming femme - riley jay being a hot blonde is so much fun porn video

TransDoe 11 months ago

Locktober - 28 October changing penis plug

Locktober - 28 October changing penis plug

XHamster 2 years ago

Fuck Machine Playtime Vol Ii Emery Lune

Fuck Machine Playtime Vol Ii Emery Lune

XHamster 2 months ago

Lady Twinks gone wild for jizz and dick

Lady Twinks gone wild for jizz and dick

MyTransfix 2 months ago

Atlanta Domme Fuck-A-Palooza (MP4 HD)

66% HD 0:30 / 9:03

Atlanta Domme Fuck-A-Palooza (MP4 HD)

Clips4sale 1 year ago

My Shemale hentai Tennis Coach Trains Me Hard Everyday

My Shemale hentai Tennis Coach Trains Me Hard Everyday

ShemaleSin 6 months ago

AB084 The training path to becoming a geisha - squirting tickle cumshot

AB084 The training path to becoming a geisha - squirting tickle cumshot

XHamster 2 years ago

Mey Evanson Private Show

Mey Evanson Private Show

Flirt4Free 4 years ago

Training Camp No More Pussy – Only She-Cock

Training Camp No More Pussy – Only She-Cock

Clips4sale 2 weeks ago

anese slave facefucking training

anese slave facefucking training

Tranny.one 4 years ago

sissypov - natty mankini magic

sissypov - natty mankini magic

TransDoe 2 years ago

See the best ride and the best ass cheekcs bouncing!!

See the best ride and the best ass cheekcs bouncing!!

Camster 3 years ago

Totk-005 Pervert Training, Bukkake And Swallowing! Shemale Anal Fuck Orgy, Riri Momotani

Totk-005 Pervert Training, Bukkake And Swallowing! Shemale Anal Fuck Orgy, Riri Momotani

GetTranny 1 year ago

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and

Becoming a Woman: The Ultimate Guide to Feminization, Female Transformation, Trans, Bisexuality and

PornoXO 1 year ago

my best birthday

61% 0:30 / 33:46

my best birthday

PornBox 2 years ago

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

IFuckedYourGF 9 months ago

Training my booty by jumping on a biggest anal pyramid sextoy

Training my booty by jumping on a biggest anal pyramid sextoy

ShemaleSin 1 month ago

I Cumming on BBC! Free Hands!

66% HD 0:39 / 1:43

I Cumming on BBC! Free Hands!

FapHouse 3 months ago

Full Crossdressing Transformation

Full Crossdressing Transformation

XHamster 4 years ago

Sexy Trans Ria Bentley Worships Her Super Hung BBC Grindr Match Like Perfect Sissy

71% 4K 0:34 / 17:46

Sexy Trans Ria Bentley Worships Her Super Hung BBC Grindr Match Like Perfect Sissy

Clips4sale 2 years ago

Shemale butt fucking fucks police cadet

Shemale butt fucking fucks police cadet

Analdin 5 years ago

Aliens Making Gender Bender Sex

Aliens Making Gender Bender Sex

HentaiGem 3 years ago

My Desire - A.B.C. = Always Be Cumming - Dee Angels Cums for You!!!

My Desire - A.B.C. = Always Be Cumming - Dee Angels Cums for You!!!

XHamster 4 years ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 2 weeks ago

dolly gets destroyed by ria bentley - extreme version

69% HD 0:24 / 36:15

dolly gets destroyed by ria bentley - extreme version

PissVids 10 months ago

Ultra-kinky Sissy College Friends getting BIG BLACK COCK

Ultra-kinky Sissy College Friends getting BIG BLACK COCK

Transvids.tv 1 year ago

Sophia Loreen Party on Jul 9, 2026 - Part 4

HD 2:00 / 46:25

Sophia Loreen Party on Jul 9, 2026 - Part 4

Flirt4Free 1 month ago

Adell Goddess Private Show

62% HD 2:00 / 12:25

Adell Goddess Private Show

Flirt4Free 2 years ago

Blonde Femdom Futa Girl Filling Her Submissive Boy With Cum

Blonde Femdom Futa Girl Filling Her Submissive Boy With Cum

BoyFriendTV 3 months ago

The Ultimate Chastity Cage Review and Guide Video

The Ultimate Chastity Cage Review and Guide Video

XHamster 5 months ago

Femboy Gaping Her Hole with Massive Pink Buttplug.

Femboy Gaping Her Hole with Massive Pink Buttplug.

FapHouse 2 years ago

EXPOSING MY FAGGOT

HD 0:19 / 10:25

EXPOSING MY FAGGOT

IWantClips 2 months ago

Training der Lady O - Tag 6 mit Louisa, Master &amp_ Lady A.J. - Teil 1 von 2

Premium HD 20:02

Training der Lady O - Tag 6 mit Louisa, Master &amp_ Lady A.J. - Teil 1 von 2

XVideosRed 7 years 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 4 months ago

Good Girl Sissy Pegging WMV

68% HD 0:29 / 10:11

Good Girl Sissy Pegging WMV

Clips4sale 4 years ago

New toy MAX XL from John Thomas Toys mounted on a Hismith machine

New toy MAX XL from John Thomas Toys mounted on a Hismith machine

XHamster 10 months ago

”TS Aspen Brooks trains Mickey OBriens tight butt with her heavy dick”

”TS Aspen Brooks trains Mickey OBriens tight butt with her heavy dick”

4Wank 1 year ago

Sasha Earth solo fap her rectal solo fucktoy

Sasha Earth solo fap her rectal solo fucktoy

4Gay 11 months ago

Tgirl Slut Training Teaser and BTS Chat

Tgirl Slut Training Teaser and BTS Chat

XHamster 1 year ago

Dimitri Caruso Private Show

HD 2:00 / 25:09

Dimitri Caruso Private Show

Flirt4Free 4 years ago

How to Put on a Chastity Cage and Train Your Ass with a BBC

How to Put on a Chastity Cage and Train Your Ass with a BBC

XHamster 2 years ago

Asian Shemale Virgin Ass Anal Training and Ass to Mouth

Asian Shemale Virgin Ass Anal Training and Ass to Mouth

XHamster 4 years ago

Mike Swift & David Golden Private Show

63% HD 2:00 / 5:10

Mike Swift & David Golden Private Show

Flirt4Free 1 week ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Flirt4Free 2 weeks ago

Sophia Loreen Party on Jul 30, 2026 - Part 3

57% 4K 2:00 / 42:41

Sophia Loreen Party on Jul 30, 2026 - Part 3

Camster 2 weeks ago

Some sissy training!

Some sissy training!

XHamster 8 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 1 week ago

Uber-uber-cute Transgirl Assets-suit Try-On - Trans Figure Positivity Butt Full salute Gorgeous

Uber-uber-cute Transgirl Assets-suit Try-On - Trans Figure Positivity Butt Full salute Gorgeous

TransTube.tv 1 year ago

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