Training Videos - Trans (119,857)

He so Wants to Cum, but His Hands and Head Are Shackled!

He so Wants to Cum, but His Hands and Head Are Shackled!

XHamster 2 years ago

SHEMALES MADE YOU IMPOTENT FOR PUSSY

58% HD 0:23 / 14:01

SHEMALES MADE YOU IMPOTENT FOR PUSSY

Clips4sale 11 months ago

My New Best Toy

62% HD 1:01 / 21:22

My New Best Toy

FapHouse 1 year ago

Merciless Hotel Throatfuck Marathon, angle 2

Merciless Hotel Throatfuck Marathon, angle 2

XHamster 1 month ago

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

57% HD 0:39 / 13:54

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

FapHouse 6 months ago

squirt show ! - Part 5

64% HD 2:00 / 9:49

squirt show ! - Part 5

Camster 1 year ago

Pissy Sissy

69% HD 0:25 / 18:02

Clips4sale 1 year ago

Nicolle & Christian Private Show

50% HD 2:00 / 5:47

Nicolle & Christian Private Show

Flirt4Free 1 year ago

Sasha Fucked Rough by Goddess Tangent

Sasha Fucked Rough by Goddess Tangent

AShemaleTube 8 years ago

TASK FOR SISSY JIZM ON STOCKINGS SANS ELIMINATING THE BELT OF V-CARD JIZM ON TIGHTS

TASK FOR SISSY JIZM ON STOCKINGS SANS ELIMINATING THE BELT OF V-CARD JIZM ON TIGHTS

GayCK 4 years ago

Nvh-021 Strengthening Anal Development Training Camp In A Competitive Swimsuit! Transsexual Reverse Anal Sex! Chibitori

Nvh-021 Strengthening Anal Development Training Camp In A Competitive Swimsuit! Transsexual Reverse Anal Sex! Chibitori

GetTranny 2 years ago

Take this fucking test and see if you're a sissy (FEMINIZATION ROLEPLAY - AI GENERATED) Clip 1

Take this fucking test and see if you're a sissy (FEMINIZATION ROLEPLAY - AI GENERATED) Clip 1

XHamster 1 year ago

Master & Christian Mckenzie & Christian Rey Private Show

54% HD 2:00 / 13:53

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Slut Training Part 1

63% HD 0:39 / 6:18

Slut Training Part 1

FapHouse 2 years ago

Deepthroat training while hard like a good trans girl should

Deepthroat training while hard like a good trans girl should

AShemaleTube 3 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Flirt4Free 10 years ago

Jhordy & Maxx Private Show

51% HD 2:00 / 53:16

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Sissified by my recent Roomate (Sissy caption Story)

Sissified by my recent Roomate (Sissy caption Story)

ShemaleSin 5 years ago

Anime Girl Training My Ass with Strap on Femdom

Anime Girl Training My Ass with Strap on Femdom

FapHouse 1 year ago

Post Op Trans Woman Masturbation - Compilation 2

Post Op Trans Woman Masturbation - Compilation 2

XHamster 1 year ago

Assfucked Maid Jasmine

63% 1:01 / 6:41

Assfucked Maid Jasmine

FapHouse 6 months ago

Riding a Dildo in Special Panties - Anal Training 57 Part 2

HD 1:01 / 10:49

Riding a Dildo in Special Panties - Anal Training 57 Part 2

FapHouse 1 year ago

Sasha Earth femboy cum hands free on a sex machine homemade amateur

Sasha Earth femboy cum hands free on a sex machine homemade amateur

XHamster 2 months ago

Transsexual Training - Bukkake Gokkun! Shemale Anal Fuck Orgy 2

Transsexual Training - Bukkake Gokkun! Shemale Anal Fuck Orgy 2

GetTranny 1 year ago

Big Test In Test Big Plug Tunnel , Anal Dilatation Training

Big Test In Test Big Plug Tunnel , Anal Dilatation Training

AbTranny 3 months ago

Large Boobs Transsexual Gwen Tennyson Lactating Her Teats with Vacuum Milking Machine

Large Boobs Transsexual Gwen Tennyson Lactating Her Teats with Vacuum Milking Machine

ShemaleSin 4 months ago

Christmas Spirit Turns You And Your Wife's Body How it Should Be [Futa Anal JOI]

Christmas Spirit Turns You And Your Wife's Body How it Should Be [Futa Anal JOI]

HentaiGem 1 year ago

Exhibit Mini-robe Dchire, Le Retour De La Belle & Le Clochard. Vanessabitchx Parischiennetrvprod

Exhibit Mini-robe Dchire, Le Retour De La Belle & Le Clochard. Vanessabitchx Parischiennetrvprod

XHamster 2 months ago

AB097 Trampy nun degraded Sexual transformation -Edging,wring (Asian and English subtitles)

AB097 Trampy nun degraded Sexual transformation -Edging,wring (Asian and English subtitles)

TrannyGem 2 years ago

Super-Sexy Cub Messy Soles Adore - Jizz on 12.five shoeless

Super-Sexy Cub Messy Soles Adore - Jizz on 12.five shoeless

4Gay 2 years ago

Sophie Fantasy Private Show

58% HD 2:00 / 6:08

Sophie Fantasy Private Show

Flirt4Free 5 months ago

Treat Me Like a Sissy-slut

61% HD 0:39 / 18:39

Treat Me Like a Sissy-slut

FapHouse 9 months ago

Female Domination homemade strapon sissy amateur

Female Domination homemade strapon sissy amateur

XHamster 4 months ago

Dani M Love Tied, Hogtied and Tickled in Her Japanese School Uniform

69% 0:29 / 6:41

Dani M Love Tied, Hogtied and Tickled in Her Japanese School Uniform

Clips4sale 3 years ago

Femboi Kara Gets Pegged and Ejaculates

Femboi Kara Gets Pegged and Ejaculates

TransTube.tv 1 year ago

Doggy Training Part 2

Doggy Training Part 2

XHamster 1 year ago

Alejandra Fox Private Show

HD 2:00 / 12:30

Alejandra Fox Private Show

Camster 1 month ago

Sabrina Smiith Private Show

67% 4K 2:00 / 10:26

Sabrina Smiith Private Show

Flirt4Free 8 months ago

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

Transvids.tv 1 year ago

Sophie Fantasy Private Show

Sophie Fantasy Private Show

Flirt4Free 1 month ago

Sissy Tries Booty To Throat For The 1st Time And Love It

Sissy Tries Booty To Throat For The 1st Time And Love It

ShemaleSin 1 month ago

Katy Ling Private Show

61% HD 2:00 / 9:04

Katy Ling Private Show

Flirt4Free 1 week ago

Anal Training in Chastity

Anal Training in Chastity

TrannyGem 7 years ago

Blow Him For Me

67% 0:11 / 9:26

Blow Him For Me

Clips4sale 3 years ago

Pegging and Cum Watching, Mistress Deep Throat and Fucks Crossdresser Masochist with Strapon and Makes Him Masturbate

HD 0:39 / 25:43

Pegging and Cum Watching, Mistress Deep Throat and Fucks Crossdresser Masochist with Strapon and Makes Him Masturbate

FapHouse 1 year ago

She’s never had it like this before, his cock takes her over the top until her eyes roll, and this country bumpkin gets creampi

65% HD 1:01 / 1:00:37

She’s never had it like this before, his cock takes her over the top until her eyes roll, and this country bumpkin gets creampi

FapHouse 4 years ago

Sophia Loreen Private Show

66% 4K 2:00 / 14:17

Sophia Loreen Private Show

Flirt4Free 1 week ago

TRANS ANGELS - Ella Nova - Learning the Joys of Anal

TRANS ANGELS - Ella Nova - Learning the Joys of Anal

ShemaleSex 1 month ago

Anal stretching and insertions training with big ball crossdressers in lingerie and nylons

Anal stretching and insertions training with big ball crossdressers in lingerie and nylons

ManPorn 1 year ago

Latina teen gets anal fucked outdoor in the mountains

Latina teen gets anal fucked outdoor in the mountains

Fapcat 2 years ago

Kaella can be a Highly Attentive Stupid Devotee of Anime Porn

Kaella can be a Highly Attentive Stupid Devotee of Anime Porn

TrannyGem 3 years ago

Facefuck Training of my compliant girlfriend

Facefuck Training of my compliant girlfriend

Amateur8 3 months ago

Emma Devereaux Private Show

HD 2:00 / 10:47

Emma Devereaux Private Show

Camster 2 years ago

Foursome Group Sex Fuckfest

Foursome Group Sex Fuckfest

XHamster 5 months ago

Carter Rains Private Show

Carter Rains Private Show

Camster 1 month ago

Sex machine and fist bang a slut's aperture

Sex machine and fist bang a slut's aperture

ShemaleSin 3 months ago

anal playtime for the horny trans giantess

HD 0:29 / 19:43

anal playtime for the horny trans giantess

PornBox 1 week ago

Naked sissy in high heels rides her dildos

Naked sissy in high heels rides her dildos

XHamster 3 years ago

Sissy Lucy Anal Training in Chastity with Biggest Dildos and Getting Pegged by Lisa

Sissy Lucy Anal Training in Chastity with Biggest Dildos and Getting Pegged by Lisa

ShemaleSin 4 years ago

Blonde Stepmom Cumshot

Blonde Stepmom Cumshot

FapHouse 1 week ago

My Femboy Roommate #1 - Helping My Femboy Lover Moving Into Our New Flat

My Femboy Roommate #1 - Helping My Femboy Lover Moving Into Our New Flat

XHamster 8 months ago

Sissy Yu Doll gets her ass lubed and fucked by bad dragon on a fuck machine

Sissy Yu Doll gets her ass lubed and fucked by bad dragon on a fuck machine

TrannyMovs 11 months ago

Marily Daniela Private Show

63% HD 2:00 / 4:40

Marily Daniela Private Show

Flirt4Free 3 years ago

40 cm monster strapon anal fucking tight legged sissy slave

40 cm monster strapon anal fucking tight legged sissy slave

AveXXX 1 month ago

My sissy bitch dressed up and pegged in his tight hole

My sissy bitch dressed up and pegged in his tight hole

XHamster 3 years ago

Amannda Skye Party on Aug 18, 2026 - Part 2

HD 2:00 / 48:29

Amannda Skye Party on Aug 18, 2026 - Part 2

Flirt4Free 1 day ago

Nin: Asian Orgasm

Nin: Asian Orgasm

Some.Porn 1 year ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

XHamster 1 year ago

Compilation Sissy Training Super Huge!

Compilation Sissy Training Super Huge!

XHamster 2 years ago

Deep Fisting & & Huge Strapon - Shemale Tearing Anal Slut Elbow Deep Anal Insertion Gape

71% HD 0:39 / 27:59

Deep Fisting & & Huge Strapon - Shemale Tearing Anal Slut Elbow Deep Anal Insertion Gape

FapHouse 1 year ago

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

FapHouse 4 months ago

Fuck My Tranny Hole

66% HD 0:39 / 13:31

Fuck My Tranny Hole

FapHouse 10 months ago

Latex TS Queens Jamie French Aspen Brooks Roxxie Moth Femdom Pegging SPH Sissy Training

Latex TS Queens Jamie French Aspen Brooks Roxxie Moth Femdom Pegging SPH Sissy Training

Eporner 9 months ago

Amazone Lady Naina fists a students ass

Amazone Lady Naina fists a students ass

FapHouse 6 years ago

Lillith xoxo Anal Training With Dildo

Lillith xoxo Anal Training With Dildo

IcePorn 5 months ago

BLACK TGIRLS - Tools of Temptation Vixen Coxx & Papi

BLACK TGIRLS - Tools of Temptation Vixen Coxx & Papi

XHamster 11 months ago

Sissy Jessica Bloom Spitroast Teaching With Screwing Machine And Faux-cocks - Ass-fuck Sissygasms and Cumswallow

Sissy Jessica Bloom Spitroast Teaching With Screwing Machine And Faux-cocks - Ass-fuck Sissygasms and Cumswallow

TrannyGem 4 months ago

Sissy Riding a Huge Dildo and Pumps Her Dick with Penispump

61% HD 0:39 / 4:00

Sissy Riding a Huge Dildo and Pumps Her Dick with Penispump

FapHouse 6 months ago

QOS Lola Crystals gets banged by Ali Da Reaper 's BIG BLACK COCK

QOS Lola Crystals gets banged by Ali Da Reaper 's BIG BLACK COCK

Transvids.tv 1 year ago

Training a Twink Femboy Noisy Ass with BBC

Training a Twink Femboy Noisy Ass with BBC

XHamster 1 month ago

The Hot Wives 5 Scene 3

The Hot Wives 5 Scene 3

Some.Porn 10 months ago

Taboo CBT Confession

54% HD 0:39 / 19:48

Taboo CBT Confession

FapHouse 3 years ago

becomingfemme - ivy chaos whats the best place to get cummed on porn video

becomingfemme - ivy chaos whats the best place to get cummed on porn video

TransDoe 1 year ago

Pretty Femboy Bitch Serving Cocks

56% 1:01 / 7:22

Pretty Femboy Bitch Serving Cocks

FapHouse 3 months ago

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

65% HD 1:01 / 11:09

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

FapHouse 4 months ago

Ftm Pegging

XHamster 7 months ago

Fat Transsexual Sestina Shay Tries PAINFUL Anal Training with a Plug

Fat Transsexual Sestina Shay Tries PAINFUL Anal Training with a Plug

ShemaleSin 1 year ago

Sissy Maid Is Taught Proper Manners

63% 1:01 / 25:25

Sissy Maid Is Taught Proper Manners

FapHouse 8 months ago

Rider shoes TGirl marionette stomping bootfetish and socks idolize

Rider shoes TGirl marionette stomping bootfetish and socks idolize

TrannyGem 1 year ago

Step Mommy Dresses Him up in Panties and Makes Him Cum Twice

66% HD 1:01 / 13:57

Step Mommy Dresses Him up in Panties and Makes Him Cum Twice

FapHouse 1 year ago

Sultry Brittany Andrews’ Boot Worship With TS Ariel Demure

Sultry Brittany Andrews’ Boot Worship With TS Ariel Demure

Clips4sale 11 months ago

”Katya Rodriguez stretches his private parts”

”Katya Rodriguez stretches his private parts”

ThePornstar 2 years ago

becomingfemme - squid raven tell me how hard and good you will use me if given the chance porn video

becomingfemme - squid raven tell me how hard and good you will use me if given the chance porn video

TransDoe 1 year 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 6 months ago

Sophia Loreen Private Show

72% 4K 2:00 / 13:07

Sophia Loreen Private Show

Flirt4Free 8 months ago

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

XHamster 4 months ago

Anal Training with BBC Dildo

Anal Training with BBC Dildo

AShemaleTube 3 years ago

30 Days to Become a Barbie - Sissy Transformation

66% HD 0:24 / 12:54

30 Days to Become a Barbie - Sissy Transformation

Clips4sale 4 weeks ago

Celeste & Liz Private Show

63% HD 2:00 / 4:37

Celeste & Liz Private Show

Flirt4Free 3 years ago

Kink Studios Tour Guide Porn

Kink Studios Tour Guide Porn

XHamster 1 month ago

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

57% HD 1:01 / 30:56

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

FapHouse 8 months ago

Sissy Princess Is an Oral Expert

Sissy Princess Is an Oral Expert

FapHouse 8 months ago

Long Machine Fuck session for Crossdresser slut with nipple pumps

Long Machine Fuck session for Crossdresser slut with nipple pumps

XHamster 2 years ago

Devin and Wendy Williams

Devin and Wendy Williams

XHamster 2 years ago

JOI: Sissy Nurse in Chastity Teaches You How to Become a Good Sissy Clip 1

JOI: Sissy Nurse in Chastity Teaches You How to Become a Good Sissy Clip 1

XHamster 7 months ago

Submissive Ladyboy First Anal Casting & Slave Training

Submissive Ladyboy First Anal Casting & Slave Training

XHamster 1 week ago

Femdom Sissy Photoshoot

Femdom Sissy Photoshoot

XHamster 2 weeks ago

Delivery man gets fucked by a transexual and a mistress

56% 0:46 / 14:50

Delivery man gets fucked by a transexual and a mistress

Clips4sale 1 month ago

”Ebony Personal Trainer Fucks Nadia Love”

”Ebony Personal Trainer Fucks Nadia Love”

Zatube 2 years ago

Pegging Couple Pink Sissy Girl With Hungry Hole

Pegging Couple Pink Sissy Girl With Hungry Hole

XHamster 1 year ago

Sissy bitch crossdresser get screwed

Sissy bitch crossdresser get screwed

2BGay 3 years ago

AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)

AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)

XHamster 2 years ago

Sissi Training - You will be transformed into a feminine slave by me and finally feminized Clip 1

Sissi Training - You will be transformed into a feminine slave by me and finally feminized Clip 1

XHamster 9 months ago

Sissyfication Session so Hot - Sissy Trainning

Sissyfication Session so Hot - Sissy Trainning

FapHouse 1 week ago

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

GayCK 4 years ago

Corporate Training - CG Shemale Hentai Animation

Corporate Training - CG Shemale Hentai Animation

FreePorn8 2 years ago

Get Fit with Kira Liv

Get Fit with Kira Liv

Some.Porn 1 year ago

Sexy Femboy Takes Anal Training Serious with Self Screw Anal Creampie???????????? ~KyleFilmStar

Sexy Femboy Takes Anal Training Serious with Self Screw Anal Creampie???????????? ~KyleFilmStar

ShemaleSin 2 years ago

Anal Training on BBC

Anal Training on BBC

XHamster 1 week ago

caged sissy rides BBC in pink heels squirts cum out of cage

52% 0:12 / 11:12

caged sissy rides BBC in pink heels squirts cum out of cage

Clips4sale 1 year ago

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119,857 results found

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