Training Videos - Trans (119,603)

Big Dildo Cock Fuck Ass

46% HD 0:39 / 2:34

Big Dildo Cock Fuck Ass

FapHouse 7 months ago

Femdom Mommy Mistress Milks Bound Sissy Crossdresser

Femdom Mommy Mistress Milks Bound Sissy Crossdresser

Eporner 7 years ago

Gay crossdresser slut sissygasm fuckwith big black dildo Clip 2

Gay crossdresser slut sissygasm fuckwith big black dildo Clip 2

XHamster 9 months ago

Trans Ria Bentley Trains StepDaughter Eden Espi For Anal Sex

Trans Ria Bentley Trains StepDaughter Eden Espi For Anal Sex

XVideos 1 year ago

It’s Just Curiosity, Right? IF IT FEELS GOOD, WHY FIGHT IT?

It’s Just Curiosity, Right? IF IT FEELS GOOD, WHY FIGHT IT?

Clips4sale 6 months ago

Sissified, degraded, humiliated & pegged cock whore slut

Sissified, degraded, humiliated & pegged cock whore slut

XHamster 11 months ago

Sissy Spitroast Training - Stretching My Ass While I Gag on Your Cock FULL VIDEO ON LAYNELOVEE MANYVIDS

Sissy Spitroast Training - Stretching My Ass While I Gag on Your Cock FULL VIDEO ON LAYNELOVEE MANYVIDS

XHamster 2 years ago

NEG&Atilde_O PAUZUDO FODEU NO PELO A TRANS LOIRA EM PUPLICO

Premium HD 11:02

NEG&Atilde_O PAUZUDO FODEU NO PELO A TRANS LOIRA EM PUPLICO

XVideosRed 3 months ago

Sissy maid trains her ass for BBC

Sissy maid trains her ass for BBC

Pornzona 2 weeks ago

Francis Malice Cheerleader 1h Anal Casting Part 1

Francis Malice Cheerleader 1h Anal Casting Part 1

XHamster 2 years ago

Ria Bentley Succumbs to Raw Anal by Gigantic BBC

Ria Bentley Succumbs to Raw Anal by Gigantic BBC

XHamster 1 year ago

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

Sissy Trainer and Encouragement BBC Anal Interracial Crossdresser Fiona Fortune

XHamster 8 months ago

Lick up Every Drop of Pre-cum! Only Then Can You Cum on My Jeans Ass! JOI CEI German

61% HD 1:01 / 9:10

Lick up Every Drop of Pre-cum! Only Then Can You Cum on My Jeans Ass! JOI CEI German

FapHouse 5 months ago

Sudden Ejaculation In Her Fufu Pinch

Sudden Ejaculation In Her Fufu Pinch

TrannyGem 2 years ago

Mistressae Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

61% HD 1:01 / 31:19

Mistressae Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

FapHouse 7 months ago

Two dominant trannies using a slave in their castle

HD 0:39 / 33:19

Two dominant trannies using a slave in their castle

FapHouse 4 years ago

Sissy Crossdresser Cat Walk Training

55% HD 1:01 / 5:10

Sissy Crossdresser Cat Walk Training

FapHouse 1 year ago

WEENIE SUCKING CROSSDRESSER

WEENIE SUCKING CROSSDRESSER

ShemaleSin 2 weeks ago

Squirty Dildo Filling up Bellas Ass

Squirty Dildo Filling up Bellas Ass

FapHouse 5 months ago

Day 8 of Sissy Training - Giggle Glitch

HD 0:39 / 21:59

Day 8 of Sissy Training - Giggle Glitch

FapHouse 6 months ago

Jerking and anal play starring a gay homo transgirl

Premium HD 15:11

Jerking and anal play starring a gay homo transgirl

XNXXGold 4 years ago

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

Premium HD 38:31

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

XVideosRed 2 months ago

Deep vibrating sound to tickle my prostate

Deep vibrating sound to tickle my prostate

XHamster 2 years ago

The Boss Gives Blowjobs for Christmas Bonus

HD 1:01 / 15:40

The Boss Gives Blowjobs for Christmas Bonus

FapHouse 1 year ago

Step-Bro Caught Crossdressing and Feminized

57% 4K 0:29 / 14:03

Step-Bro Caught Crossdressing and Feminized

Clips4sale 3 years ago

Lady Fee Is Feeling Stressed so Wants to Take It Out on Sissy

63% HD 0:39 / 6:18

Lady Fee Is Feeling Stressed so Wants to Take It Out on Sissy

FapHouse 1 month ago

Wear Silky Panties for Me

Wear Silky Panties for Me

FapHouse 11 months ago

Yoruichi Sissy Training Part 4 Joi Cbt Cei (Dildo Play, Self facial, Cum Eating, Ball Bust, Chastity, Crossdress)

Yoruichi Sissy Training Part 4 Joi Cbt Cei (Dildo Play, Self facial, Cum Eating, Ball Bust, Chastity, Crossdress)

XVideos 4 years ago

Giant Anal Cone Dildo Sitting and Bouncing Till the Base & Gaping Asshole

HD 0:39 / 11:57

Giant Anal Cone Dildo Sitting and Bouncing Till the Base & Gaping Asshole

FapHouse 5 days ago

Hattabi4ik sissy femboy trap splatter ejaculation self shag warm humungous bootie compilation

Hattabi4ik sissy femboy trap splatter ejaculation self shag warm humungous bootie compilation

TrannyGem 2 years ago

POINT OF VIEW housemate finds your underpants and feminizes you Jerk Off Instructions superior trans female

POINT OF VIEW housemate finds your underpants and feminizes you Jerk Off Instructions superior trans female

Transvids.tv 1 year ago

G083 - Blowjob 14, deepthroat Frenzy

HD 0:39 / 38:16

G083 - Blowjob 14, deepthroat Frenzy

FapHouse 9 months ago

Porque os homens tem tanto desejo por trans? [Trailer] - Ts Vanessa Rafaella

Porque os homens tem tanto desejo por trans? [Trailer] - Ts Vanessa Rafaella

XVideos 1 year ago

Luna Florez Private Show

4K 2:00 / 11:36

Luna Florez Private Show

Camster 1 week ago

Femboy Anal Training

Femboy Anal Training

FapHouse 1 week ago

Sissycdmish - BBC Loving Slut in Fishnets and Heels

Sissycdmish - BBC Loving Slut in Fishnets and Heels

XHamster 2 months ago

TRANSGENDER SISSY DROWNS IN DEEPTHROAT FUN AND URINATE

TRANSGENDER SISSY DROWNS IN DEEPTHROAT FUN AND URINATE

ShemaleSin 1 month ago

Trans Domina Mentally Breaks Her Sub GF and Slut by Slapping Her and Her Tits and Then Cum on Her with Sadistic Bliss

Trans Domina Mentally Breaks Her Sub GF and Slut by Slapping Her and Her Tits and Then Cum on Her with Sadistic Bliss

FapHouse 2 months ago

Sophia Loreen Party on Jun 4, 2026 - Part 3

HD 2:00 / 1:00:20

Sophia Loreen Party on Jun 4, 2026 - Part 3

Camster 1 month ago

Crhistian & Dereckk and 2 Hot Friends

65% HD 2:00 / 1:04:58

Crhistian & Dereckk and 2 Hot Friends

Flirt4Free 7 years ago

PRETTY EBONY TS JERKOFF COMPILATION

PRETTY EBONY TS JERKOFF COMPILATION

XHamster 3 months ago

Blonde Femdom Futa Girl Filling Her Submissive Boy With Cum

Blonde Femdom Futa Girl Filling Her Submissive Boy With Cum

BoyFriendTV 2 months ago

Emma & Zayden Private Show

HD 2:00 / 15:56

Emma & Zayden Private Show

Camster 1 week ago

I Fuck Lola Ass!!!

HD 0:39 / 11:02

I Fuck Lola Ass!!!

FapHouse 2 weeks ago

Sophia Loreen Party on Jul 18, 2026 - Part 3

HD 2:00 / 57:27

Sophia Loreen Party on Jul 18, 2026 - Part 3

Flirt4Free 6 days ago

10 Inch Dildo Chastity Sissygasm on Feet 007

66% HD 1:01 / 20:33

10 Inch Dildo Chastity Sissygasm on Feet 007

FapHouse 4 years ago

White Lesson

HD 1:01 / 23:40

FapHouse 1 year ago

Sissy's Feminization

Sissy's Feminization

Pornzona 4 months ago

Toy for Both. Threesome with Trans Sex Doll, Blowjob, DP Hot Sex

Toy for Both. Threesome with Trans Sex Doll, Blowjob, DP Hot Sex

FapHouse 5 months ago

Futa wolf demands forest toll

55% HD 0:23 / 7:44

Futa wolf demands forest toll

Clips4sale 2 years ago

PANTYHOSE BONDAGE LAPDANCE WITH ALBA ZEVON

PANTYHOSE BONDAGE LAPDANCE WITH ALBA ZEVON

Clips4sale 1 year ago

Travesti safada fica se alisando na pausa do trabalho mostrando seu cl&iacute_toris

Premium HD 10:01

Travesti safada fica se alisando na pausa do trabalho mostrando seu cl&iacute_toris

XNXXGold 2 weeks ago

We Laugh at Your Mini Cock! Fuck a Pillow Until You Come! Loser JOI German!

55% HD 1:01 / 8:39

We Laugh at Your Mini Cock! Fuck a Pillow Until You Come! Loser JOI German!

FapHouse 5 months ago

Feminization Sissyfication Sissy instructing - Trunk Adore - Utter version

Feminization Sissyfication Sissy instructing - Trunk Adore - Utter version

TrannyGem 2 years ago

Young Asian goddess dominates and fucks sissy's ass with a strap on

HD 0:39 / 10:17

Young Asian goddess dominates and fucks sissy's ass with a strap on

FapHouse 3 years ago

Now Her Life Has Purpose

Now Her Life Has Purpose

FapHouse 1 year ago

Zayra Ross Private Show

4K 2:00 / 15:23

Zayra Ross Private Show

Flirt4Free 1 week ago

Lika Kai Private Show

4K 2:00 / 40:16

Lika Kai Private Show

Camster 1 week ago

Sophia Loreen Private Show

HD 2:00 / 13:41

Sophia Loreen Private Show

Camster 1 week ago

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roped up my feminized sissy manmeat slut and plumbed her with a romping machine

Gayhub 9 months ago

Sex on a Motorcycle Anal Squirting

Sex on a Motorcycle Anal Squirting

FapHouse 2 years ago

Mistress Plays with Her Futanari Dolls

55% 0:39 / 41:16

Mistress Plays with Her Futanari Dolls

FapHouse 1 year ago

Big Dildo Fucking My Ass Hole Hard

Big Dildo Fucking My Ass Hole Hard

XHamster 1 week ago

Ladyboy Slut Showing Her Sweet Body and Posing on Cam

Ladyboy Slut Showing Her Sweet Body and Posing on Cam

FapHouse 2 years ago

Bisexual sissy husband pegging - check out my links for full video

Bisexual sissy husband pegging - check out my links for full video

Pornfact 1 week ago

Lust Academy - Audrey the Trans Succubus Fucks James in Doggy Style Part 5

55% HD 1:01 / 6:11

Lust Academy - Audrey the Trans Succubus Fucks James in Doggy Style Part 5

FapHouse 10 months ago

The Lust of Sissy Boy - Concerns About My Boy Friend

HD 0:39 / 11:35

The Lust of Sissy Boy - Concerns About My Boy Friend

FapHouse 1 year ago

Fvr - 33 - Feminize Him - Date 3 - Riley

63% VR 0:08 / 17:41

Fvr - 33 - Feminize Him - Date 3 - Riley

FapHouse 3 months ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

57% HD 1:01 / 13:21

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

FapHouse 5 months ago

Sissy BBC Painful Anal Training

Sissy BBC Painful Anal Training

PornoXO 6 years ago

Cute Shemale Anal Training

HD 1:01 / 34:55

Cute Shemale Anal Training

FapHouse 2 years ago

Sissy Dee and Lady Fee in Matching Outfits

63% HD 0:39 / 7:45

Sissy Dee and Lady Fee in Matching Outfits

FapHouse 3 weeks ago

Trans Sissy Whore disciplined by Mistresse Murmur compilation

Trans Sissy Whore disciplined by Mistresse Murmur compilation

ShemaleSin 7 months ago

Bondage blowjob training

Bondage blowjob training

XHamster 2 months ago

Sissy trying new dress with abilty to get fucked fast

Sissy trying new dress with abilty to get fucked fast

XVideos 1 year ago

CUM PEGGING and FISTING MISTRESS COMPILATION

CUM PEGGING and FISTING MISTRESS COMPILATION

XVideos 1 year ago

Feminization - Sissyfication - Sissy teaching - Support for the sissy

Feminization - Sissyfication - Sissy teaching - Support for the sissy

TrannyGem 1 year ago

Tied up and Gagged Sissy PIG Milking Slut MUST cum handsfree

Tied up and Gagged Sissy PIG Milking Slut MUST cum handsfree

XHamster 4 years ago

Training My Throat

Training My Throat

XHamster 1 month 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 2 weeks ago

Trans latina plugs herself raw until she gushes with a big dick anal creampie

Trans latina plugs herself raw until she gushes with a big dick anal creampie

JuicyTrans 1 month ago

CUMSHOT COMPILATION FREE HANDS SISSYGASM

Premium HD 5:10

CUMSHOT COMPILATION FREE HANDS SISSYGASM

XVideosRed 1 year ago

Trans Girl *** Orgasm

55% HD 1:01 / 19:44

Trans Girl *** Orgasm

FapHouse 1 year ago

Sissy Maid Playing with Herself with Bondage, Huge Dildos, and Chastity

Sissy Maid Playing with Herself with Bondage, Huge Dildos, and Chastity

XHamster 1 month ago

TGirl Gigi dildo fucked in the ass until she squirts lube out of her ass

TGirl Gigi dildo fucked in the ass until she squirts lube out of her ass

XVideos 3 years ago

sissy boi Bailey training her sissy hole

sissy boi Bailey training her sissy hole

XVideos 4 years ago

Anal Training 68 Part 4 - Dildo Riding

HD 0:39 / 11:17

Anal Training 68 Part 4 - Dildo Riding

FapHouse 1 year ago

Shemale Domina Throating her Ashtray Slave Boy

Shemale Domina Throating her Ashtray Slave Boy

XGroovy 2 years ago

Luke Hardy & Cristian Ford Party on Apr 11, 2026 - Part 2

HD 2:00 / 1:20:04

Luke Hardy & Cristian Ford Party on Apr 11, 2026 - Part 2

Flirt4Free 3 months ago

Edging My Girl Cock with My Clear Fleshlight

60% 1:01 / 24:43

Edging My Girl Cock with My Clear Fleshlight

FapHouse 2 years ago

Lady Twinks gone wild for jizz and dick

Lady Twinks gone wild for jizz and dick

MyTransfix 2 months ago

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

FapHouse 3 years ago

Tammysissy with Cum and Piss in Face and Body

Tammysissy with Cum and Piss in Face and Body

FapHouse 3 weeks ago

Uncontrollable Body Shaking Prostate Orgasm!!!

Uncontrollable Body Shaking Prostate Orgasm!!!

XVideos 3 years ago

Feminizaton - Sissy Training - COSMIC SISSY DESTINY

Feminizaton - Sissy Training - COSMIC SISSY DESTINY

ShemaleSin 2 years ago

Time to Submit Sissy

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Time to Submit Sissy

FapHouse 1 month ago

2 Sissy Latex Nurses Getting Pegged in Chastity by MILF Lisa

54% HD 0:39 / 36:16

2 Sissy Latex Nurses Getting Pegged in Chastity by MILF Lisa

FapHouse 2 years ago

TV Nutte Monique - out on the street again, showing myself in public

TV Nutte Monique - out on the street again, showing myself in public

XHamster 1 year ago

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Anastasia Mistress fuck strapon anal submission man amateur homemade Sasha Earth

XVideos 1 month ago

My sissy cumslut

51% HD 1:00 / 14:19

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Clips4sale 1 year ago

Full: Trans Dva Ass Clapping and Anal Fucked with BBC Dildo

HD 1:01 / 11:05

Full: Trans Dva Ass Clapping and Anal Fucked with BBC Dildo

FapHouse 6 months ago

Sissy Slave Interview

48% HD 0:10 / 9:32

Sissy Slave Interview

LoyalFans 2 years ago

I Want to Be a Barbie Doll

I Want to Be a Barbie Doll

FapHouse 1 year ago

Deep Throat Training with Dr. Justice

Deep Throat Training with Dr. Justice

FapHouse 6 months ago

Luna Florez Private Show

HD 2:00 / 10:04

Luna Florez Private Show

Camster 3 years ago

Waiting in the tunnel...

Waiting in the tunnel...

XHamster 4 years ago

Rectal Screw with Pound Machine 1

Rectal Screw with Pound Machine 1

TrannyGem 2 years ago

Sissy Training for Hotel Housekeeping Job

Sissy Training for Hotel Housekeeping Job

XHamster 2 years ago

Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.

Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.

XHamster 1 month ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Sissy Charlotte Deepthroat Training on Mikes Huge Cock

HD 1:01 / 16:02

Sissy Charlotte Deepthroat Training on Mikes Huge Cock

FapHouse 10 months ago

(s06e06) - the Slutty Adventures of Neetrasurik

HD 1:01 / 17:05

(s06e06) - the Slutty Adventures of Neetrasurik

FapHouse 1 year ago

Yei Vela Private Show

Yei Vela Private Show

Flirt4Free 3 years ago

Top Beautiful Trans Mistress Fucked Her Slave Ladyboy

58% HD 0:39 / 32:44

Top Beautiful Trans Mistress Fucked Her Slave Ladyboy

FapHouse 1 year ago

Feminized and Love it -- you will too

Feminized and Love it -- you will too

TrannyGem 7 years ago

Sabrina Smiith Private Show

HD 2:00 / 30:27

Sabrina Smiith Private Show

Flirt4Free 8 months ago

Anna Summerss Private Show

HD 2:00 / 49:59

Anna Summerss Private Show

Flirt4Free 4 years ago

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

66% HD 0:39 / 5:59

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

FapHouse 6 months ago

Lika Kai Private Show

4K 2:00 / 10:19

Lika Kai Private Show

Camster 1 week ago

Hottest Cock Milking Ever

55% HD 0:39 / 12:34

Hottest Cock Milking Ever

FapHouse 6 months ago

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