Training Videos - Trans (117,416)

BUBBLZexe dominates with his big cock & gives a steamy solo session

BUBBLZexe dominates with his big cock & gives a steamy solo session

GayVD 1 month 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

Sissy Whore Training 2

Sissy Whore Training 2

xHamster 1 year ago

Pumping Crimson Good-Sized Long Dragon Snake Faux-Cock Deep in my Demolished Booty

Pumping Crimson Good-Sized Long Dragon Snake Faux-Cock Deep in my Demolished Booty

GayCK 4 years ago

Dildo anal invasion

Dildo anal invasion

xHamster 3 years ago

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

xHamster 1 year ago

POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock

POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock

xHamster 10 months ago

Advanced Anal Stretching with Jasmine-Dlight: Part 4 - Miss Hannah Blake Joins The Training

Advanced Anal Stretching with Jasmine-Dlight: Part 4 - Miss Hannah Blake Joins The Training

XVideos 7 months ago

Trans Angel Ella Nova and Tgirl Natalie Mars get into a steamy reverse

Trans Angel Ella Nova and Tgirl Natalie Mars get into a steamy reverse

W1mp 1 week ago

Tranny moaning and edging herself while riding a BBC I am going to fucking Cum

Tranny moaning and edging herself while riding a BBC I am going to fucking Cum

xHamster 2 years ago

Sinn Sage Ariel Demure In Training (1080)

Sinn Sage Ariel Demure In Training (1080)

XVideos 2 months ago

Brides Hands-free BBC Cumshots

Brides Hands-free BBC Cumshots

xHamster 1 month ago

Dominatrix Nika tied up Sissy Blaire_18 with ropes and plays with his nipples. Gag and scratching

Dominatrix Nika tied up Sissy Blaire_18 with ropes and plays with his nipples. Gag and scratching

xHamster 1 year ago

Sophia Loreen Party on Jun 23, 2026 - Part 4

HD 2:00 / 35:23

Sophia Loreen Party on Jun 23, 2026 - Part 4

Camster 1 day ago

Lizzy Woo's Ass Wrecked First-time Strap-on Pegging by Your Cruel Stepmommy Domme Watch Her Beg for More

Lizzy Woo's Ass Wrecked First-time Strap-on Pegging by Your Cruel Stepmommy Domme Watch Her Beg for More

xHamster 1 month ago

Ftm Soldier Receives Humiliating Pussy Discipline Training

Ftm Soldier Receives Humiliating Pussy Discipline Training

xHamster 1 month ago

Fat Ass Outdoor Sissy Slut, Volleyball Shorts

Fat Ass Outdoor Sissy Slut, Volleyball Shorts

xHamster 1 month ago

3D Futa Porn: Sexy Buxom Shemale Mistress Dominates Her Pet-boys And Her Maid

3D Futa Porn: Sexy Buxom Shemale Mistress Dominates Her Pet-boys And Her Maid

XGroovy 2 years ago

Bella Joie Takes Control: Throat Training & Ass Wrecking till she cums

Bella Joie Takes Control: Throat Training & Ass Wrecking till she cums

Clips4sale 9 months ago

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV

xHamster 2 months ago

Sissycdmish - Double Stuffed Butt Slut

Sissycdmish - Double Stuffed Butt Slut

xHamster 3 months ago

Sissy Bitches m&uuml_ssen blasen &ndash_ Sissification mit der Lady der Feminisierung

Sissy Bitches m&uuml_ssen blasen &ndash_ Sissification mit der Lady der Feminisierung

XVideos 3 years ago

4K - What's under my trench coat EP 1 - Fishnet Lingerie

63% 4K 0:22 / 30:01

4K - What's under my trench coat EP 1 - Fishnet Lingerie

Clips4sale 1 month ago

Chief (ASMR) gets angry and trains you how to immense jizm!

Chief (ASMR) gets angry and trains you how to immense jizm!

TrannyGem 1 year ago

Husbands ass gets stretched by wife's cock

Husbands ass gets stretched by wife's cock

xHamster 1 year ago

Master & Christian Mckenzie & Christian Rey Private Show

HD 2:00 / 28:09

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Sissyfication Feminization Hotwife Sissy instructing Lesson one - When your wifey is with her paramour

Sissyfication Feminization Hotwife Sissy instructing Lesson one - When your wifey is with her paramour

TrannyGem 9 months ago

Transformed husband into a slut and four more cocks and two dominatrixes

Transformed husband into a slut and four more cocks and two dominatrixes

xHamster 2 years ago

Corporate Training - Futanari Animation

Corporate Training - Futanari Animation

Some.Porn 2 years ago

Long dildo masturbation at the entrance of the apartment

Long dildo masturbation at the entrance of the apartment

TrannyGem 3 years ago

Big Compilation Of Anal Orgasms And Solo Cumshots Collection sissygasm ( trap milking )

Big Compilation Of Anal Orgasms And Solo Cumshots Collection sissygasm ( trap milking )

Pornzona 3 months ago

Having a Hard Time - Shemale Jane Dreams of Fucking Larissa in Front of Noah & Farah

HD 0:39 / 10:32

Having a Hard Time - Shemale Jane Dreams of Fucking Larissa in Front of Noah & Farah

FapHouse 1 week ago

Turned Out Sissy Interactive Toy Experience

Turned Out Sissy Interactive Toy Experience

xHamster 1 year ago

put two mitts in the booty of her sissy fuckslut. handballing

put two mitts in the booty of her sissy fuckslut. handballing

TrannyGem 3 years ago

PMV Compilation - Finest From MusicMonk five

PMV Compilation - Finest From MusicMonk five

TrannyGem 4 years ago

Taniaxtorres Doing Sissytherapy

Taniaxtorres Doing Sissytherapy

xHamster 4 weeks ago

Crossdressing Sissy Humiliation with Katie Katt - MP4 (HD 1080p)

58% HD 0:23 / 6:04

Crossdressing Sissy Humiliation with Katie Katt - MP4 (HD 1080p)

Clips4sale 1 year ago

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

59% HD 0:39 / 8:39

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

FapHouse 4 months ago

Gwen Rides and Cums

Gwen Rides and Cums

xHamster 10 months ago

Training Nympho Hot Ts Stepsister Not To Dress Like Slut And To Take Big Cock

Training Nympho Hot Ts Stepsister Not To Dress Like Slut And To Take Big Cock

AbTranny 1 day ago

Bound Nuru massage leads to creampie

Bound Nuru massage leads to creampie

xHamster 1 year ago

Evil Stepmom Teaching Her Submissive Stepson How To Suck Cock

Evil Stepmom Teaching Her Submissive Stepson How To Suck Cock

xHamster 1 year ago

Mistress Lady Renee - Used condoms for sissy to clean - wmv

Mistress Lady Renee - Used condoms for sissy to clean - wmv

Clips4sale 1 year ago

Ripped Nerdy Guy Loves to Chat

Ripped Nerdy Guy Loves to Chat

Flirt4Free 8 years ago

Christian & Nicco & Elvis Private Show

63% HD 2:00 / 4:40

Christian & Nicco & Elvis Private Show

Flirt4Free 2 years ago

Rubber Foot Gimp ft TS Slayer

HD 0:28 / 14:42

Rubber Foot Gimp ft TS Slayer

IWantClips 1 week ago

Trans Gwen Tennyson Receives Gape Anal Sex and the Biggest Creampie of Her Life

Trans Gwen Tennyson Receives Gape Anal Sex and the Biggest Creampie of Her Life

xHamster 2 months ago

MAMMAS BOI IN PVC BLACK HEELS THIGH HIGH BOOTS LEATHER TOP FISHNETS SISSY STOCKINGS AND MISTRESS IN FULL OVC CATSUIT BLOWJOB P1

65% 0:21 / 10:19

MAMMAS BOI IN PVC BLACK HEELS THIGH HIGH BOOTS LEATHER TOP FISHNETS SISSY STOCKINGS AND MISTRESS IN FULL OVC CATSUIT BLOWJOB P1

Clips4sale 2 years ago

Play Ass Holes

63% HD 2:00 / 15:28

Flirt4Free 1 year ago

Humiliating Date Story by a Pathetic Piggy

59% HD 1:01 / 14:11

Humiliating Date Story by a Pathetic Piggy

FapHouse 8 months ago

Watch this amateur teen sissy CD give a sloppy BJ and swallow a hot cum load

Watch this amateur teen sissy CD give a sloppy BJ and swallow a hot cum load

TrannyMovs 6 months ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 1 week ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

HD 2:00 / 13:35

Sophia Loreen Private Show

Flirt4Free 2 months 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

Horny 1

xHamster 1 month ago

Sissy sucking tutor

Sissy sucking tutor

ShemaleSin 4 years ago

GETTING RID OF MY SEX TOY

GETTING RID OF MY SEX TOY

aShemaleTube 2 months ago

Daimond Cooper Private Show

Daimond Cooper Private Show

Flirt4Free 3 weeks ago

Ali Da Reaper plowing the tear up outta me wIth his meaty black beefstick

Ali Da Reaper plowing the tear up outta me wIth his meaty black beefstick

TrannyGem 3 years ago

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

xHamster 3 years ago

Yei Vela Private Show

Yei Vela Private Show

Flirt4Free 2 years ago

Kristy Butty Private Show

4K 2:00 / 10:07

Kristy Butty Private Show

Camster 9 months ago

Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.

Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.

xHamster 8 months ago

This Guy Made It Rain a Lot of Cum on My White Boy Face

This Guy Made It Rain a Lot of Cum on My White Boy Face

xHamster 1 year ago

Modernwhiteboi Jes BBC Dildo, Ass to Mouth

Modernwhiteboi Jes BBC Dildo, Ass to Mouth

xHamster 2 weeks ago

Tiny Trans Kawaii Fiona Bangs a Yielding Trans Puppy-Beauty

Tiny Trans Kawaii Fiona Bangs a Yielding Trans Puppy-Beauty

Amateur8 1 year ago

FUCKED WITH MY HIGH HEEL

FUCKED WITH MY HIGH HEEL

xHamster 2 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 day ago

Sissy Anal Slut PMV 2017

Sissy Anal Slut PMV 2017

Eporner 7 years ago

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

xHamster 8 months ago

Teaser: Cloudy Sunday

Teaser: Cloudy Sunday

Gayhub 1 week ago

Cumslut Training Session two

Cumslut Training Session two

Amateur8 4 years ago

Charlie Cano Private Show

61% HD 2:00 / 5:11

Charlie Cano Private Show

Flirt4Free 3 years ago

Shemale Brandy Loves Anal with Jason Follow Along with Us

Shemale Brandy Loves Anal with Jason Follow Along with Us

xHamster 2 years ago

Make Me Bi For The Cuckold Cunt (Quicktime)

Make Me Bi For The Cuckold Cunt (Quicktime)

Clips4sale 3 years ago

Sissy Candy on Her Inflatable Chair in Self Bondage with Her Fucking Machine

Sissy Candy on Her Inflatable Chair in Self Bondage with Her Fucking Machine

xHamster 1 month ago

YOU ARE THE PERFECT MAID FOR MY PARTY!

4K 0:25 / 10:23

YOU ARE THE PERFECT MAID FOR MY PARTY!

Clips4sale 3 years ago

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

xHamster 2 years ago

Hard Sissy Training Use and Cum

Hard Sissy Training Use and Cum

xHamster 8 months ago

Sissy Training Day 1: First Task for Mistress

Sissy Training Day 1: First Task for Mistress

xHamster 2 weeks 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

Sissy Training with Mistress

Sissy Training with Mistress

TrannyGem 7 years ago

Brides Hands-free BBC Cumshots

66% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 1 month ago

CALAVERRECTION: I’m Hard. He’s Hard. You’re Just Begging.

CALAVERRECTION: I’m Hard. He’s Hard. You’re Just Begging.

Clips4sale 6 months ago

Sophia Loreen Demonstrates Amazing Flexibility

Sophia Loreen Demonstrates Amazing Flexibility

Flirt4Free 4 years ago

Stepmom to Stepdaughter's BF I Think I Can Help You With That Problem You've Been Having

Stepmom to Stepdaughter's BF I Think I Can Help You With That Problem You've Been Having

Tranny.one 2 years ago

Chastity cage holds femboy's wildest release

Chastity cage holds femboy's wildest release

ShemaleSin 1 day ago

Part 1: sissy sleepover and encouraged bi cock sucking humiliation for sissy bitch with Mistress L Hush

46% 0:11 / 10:38

Part 1: sissy sleepover and encouraged bi cock sucking humiliation for sissy bitch with Mistress L Hush

Clips4sale 3 years ago

Claire Tenebrarum & Natalie Mars take turns training each other with toys

Claire Tenebrarum & Natalie Mars take turns training each other with toys

TrannyMovs 6 months ago

Livejasmin Session with Mistress Audrey - Anal JOI and CUM - 9 Inch Dildo

Livejasmin Session with Mistress Audrey - Anal JOI and CUM - 9 Inch Dildo

TrannyGem 7 years ago

sissy fist training

sissy fist training

xHamster 4 years 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

Carmen Melatonin learns how to handle two BBCs like a pro, with a hot bisexual twist

Carmen Melatonin learns how to handle two BBCs like a pro, with a hot bisexual twist

TrannyMovs 1 month ago

Finally all in with 15 inch King Cock dildo

Finally all in with 15 inch King Cock dildo

xHamster 7 months ago

Lady in Red

Clips4sale 1 year ago

Sophia Loreen Party on Jun 4, 2026 - Part 3

66% HD 2:00 / 1:00:20

Sophia Loreen Party on Jun 4, 2026 - Part 3

Flirt4Free 2 weeks ago

Protection Sissy

Protection Sissy

TrannyGem 4 years ago

Whore Sonechka25 groans loudly and ends with cum spray from anal masturbation. Russian voiceover. Sissy training (two)

Whore Sonechka25 groans loudly and ends with cum spray from anal masturbation. Russian voiceover. Sissy training (two)

ShemaleSin 3 years ago

Mistress sissifies her bitch boi and pounds his boi pussy

Mistress sissifies her bitch boi and pounds his boi pussy

xHamster 2 years ago

Cute Naked Sissy Dildo Fuck and Dirty Talk

65% HD 0:39 / 26:55

Cute Naked Sissy Dildo Fuck and Dirty Talk

FapHouse 1 year ago

Elias & Elix Private Show

70% HD 2:00 / 14:12

Elias & Elix Private Show

Flirt4Free 9 months ago

Femboy anal collection 2025 destroyed by giant dicks

Femboy anal collection 2025 destroyed by giant dicks

JuicyTrans 2 weeks 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 weeks ago

Wild Sabrina Members-Only Show

HD 2:00 / 22:50

Wild Sabrina Members-Only Show

Flirt4Free 5 years ago

Amateur gay webcam anal gape close-up

Amateur gay webcam anal gape close-up

xHamster 4 months ago

Crossdressed Sissy Dressed In Satan Costume For Halloween Energetically Rails 8 inch Fuck Stick

Crossdressed Sissy Dressed In Satan Costume For Halloween Energetically Rails 8 inch Fuck Stick

TrannyGem 2 years ago

LEZ BE BAD - Femdom MILF Elise Graves Trains Victoria Voxxx To DOMINATE Yhivi With BDSM Bondage

LEZ BE BAD - Femdom MILF Elise Graves Trains Victoria Voxxx To DOMINATE Yhivi With BDSM Bondage

Some.Porn 5 months ago

Sexy Grup Show

Flirt4Free 2 years ago

The intern is trained in the office

The intern is trained in the office

xHamster 1 month ago

A Femboy Story, Blast From the Past Video: Old Camshow Comp Where I Discover Bigger and Bigger Toys

A Femboy Story, Blast From the Past Video: Old Camshow Comp Where I Discover Bigger and Bigger Toys

xHamster 2 weeks ago

Messy Lipstick Tgirl Lesbian Facefucking

Messy Lipstick Tgirl Lesbian Facefucking

xHamster 1 month ago

Sissy teasing in shiny leggings and new inverted chastity

Sissy teasing in shiny leggings and new inverted chastity

xHamster 9 months ago

Cute Shemale Armpits Hairy Masturbation and Titjob to Dildo

Cute Shemale Armpits Hairy Masturbation and Titjob to Dildo

xHamster 4 months ago

Perseo & Dafne Private Show

Perseo & Dafne Private Show

Flirt4Free 1 year ago

Anal Alien Eggs Insemination Femdom

Anal Alien Eggs Insemination Femdom

xHamster 1 month ago

TRANS CUTIES - Glamorous Ella Nova And Tranny Natalie Mars End Yoga Class In Hawt Anal Training Session

TRANS CUTIES - Glamorous Ella Nova And Tranny Natalie Mars End Yoga Class In Hawt Anal Training Session

ShemaleSin 1 week ago

Transgirl Flex Her Big Balls

71% 1:01 / 11:20

Transgirl Flex Her Big Balls

FapHouse 4 months ago

Mikes Hanon Private Show

Mikes Hanon Private Show

Flirt4Free 4 years ago

Bonny Shiine Private Show

61% HD 2:00 / 16:56

Bonny Shiine Private Show

Flirt4Free 2 years ago

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117,416 results found

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