Training Videos - Trans (88,713)

Sissy Strap-on Fucked by Asian Mistress Dominafire

Sissy Strap-on Fucked by Asian Mistress Dominafire

xHamster 3 weeks ago

Little slut bottom getting trained to take girl dick. Part: 2

Little slut bottom getting trained to take girl dick. Part: 2

xHamster 1 month ago

Sissy In Diaper Punished With Strict Pegging

Sissy In Diaper Punished With Strict Pegging

BallsAndBoobs 6 months ago

Crossdressing Sissy Husband gets pegged & humiliated

Crossdressing Sissy Husband gets pegged & humiliated

xHamster 1 year ago

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

69% HD 1:01 / 10:12

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

FapHouse 1 year ago

Nurse domina fire inserts huge toy in patients ass

65% HD 1:01 / 20:12

Nurse domina fire inserts huge toy in patients ass

FapHouse 3 years ago

Blonde Bimbo Gets Deep Anal Training from Tall Redhead Futanari in Standing Fuck Lift

Blonde Bimbo Gets Deep Anal Training from Tall Redhead Futanari in Standing Fuck Lift

AnimeHentaiXHub 5 months ago

Huge anal masturbator sissygasm

Huge anal masturbator sissygasm

xHamster 1 year ago

3D Femboy trained by futanari big dick

3D Femboy trained by futanari big dick

aShemaleTube 1 year ago

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

TrannyGem 4 years ago

Sex-er-cise

xHamster 11 months ago

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

xHamster 1 year ago

Mistress Teases Cross-dressing Masochist with Cane and Hot Wax and Uses Nipple Clips to Enlarge and Train His Nipples

60% HD 0:39 / 26:04

Mistress Teases Cross-dressing Masochist with Cane and Hot Wax and Uses Nipple Clips to Enlarge and Train His Nipples

FapHouse 3 weeks ago

SMOOTH LITTLE SISSY

61% HD 0:10 / 11:46

SMOOTH LITTLE SISSY

LoyalFans 3 years ago

Sissy Training by Queen Daralis Part 2

65% HD 0:39 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse 1 month ago

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

xHamster 5 months ago

Pack you up with my love, my little juice puff cake

Pack you up with my love, my little juice puff cake

WebcamBros 1 month ago

Swallow My Cum

xHamster 5 months ago

Chastity Sissy Maid Service Training With Ria Bentley

Chastity Sissy Maid Service Training With Ria Bentley

Amateur8 4 months ago

GIRL COCK RUINED YOU

48% HD 0:10 / 15:39

GIRL COCK RUINED YOU

LoyalFans 1 month ago

FetishEmmanuella video 12 - Vinyl Thigh High Boots -part 2

FetishEmmanuella video 12 - Vinyl Thigh High Boots -part 2

xHamster 2 months ago

Chubby Maram Play with Her Dildo so Hot Sexy Trans

Chubby Maram Play with Her Dildo so Hot Sexy Trans

FapHouse 6 months ago

New Girl in the Sissy Harem

New Girl in the Sissy Harem

xHamster 5 months ago

becomingfemme - clarice darling showing off her progression

becomingfemme - clarice darling showing off her progression

TransDoe 2 years ago

Luke Hardy & Cristian Ford Party on Jan 13, 2026 - Part 3

62% HD 2:00 / 3:14:28

Luke Hardy & Cristian Ford Party on Jan 13, 2026 - Part 3

Flirt4Free 2 months ago

Kendall Rousee Private Show

63% 4K 2:00 / 10:14

Kendall Rousee Private Show

Flirt4Free 1 week ago

Turned Into a Good Pet

Turned Into a Good Pet

FapHouse 8 months ago

Christian & Nicco & Elvis Private Show

47% HD 2:00 / 5:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Sissy Maid Ballet Boot Training

Sissy Maid Ballet Boot Training

xHamster 3 years ago

Jessica's Anal Training Series Episode 2

Jessica's Anal Training Series Episode 2

xHamster 5 days ago

Anal Training #11

HD 1:01 / 19:35

Anal Training #11

FapHouse 1 year ago

Nicco & Michael & Santiago Private Show

57% HD 2:00 / 6:03

Nicco & Michael & Santiago Private Show

Flirt4Free 2 years ago

Slut Training Maxine X Double Stuffed in All Holes

HD 1:01 / 48:11

Slut Training Maxine X Double Stuffed in All Holes

FapHouse 1 month ago

Dominas Dirty Demands SISSY TRAINING ASMR JOI

Dominas Dirty Demands SISSY TRAINING ASMR JOI

xHamster 1 week ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Flirt4Free 2 days ago

Whorish Femboy Maid in Innocence Takes Harsh Assfucking Teaching ~oscar20xxx~

Whorish Femboy Maid in Innocence Takes Harsh Assfucking Teaching ~oscar20xxx~

GayCK 6 years ago

Gym Tips for Sluts Feminization Motivation

64% HD 1:01 / 11:57

Gym Tips for Sluts Feminization Motivation

FapHouse 5 months ago

Petra the hardcore anal slut (incl dap tap fist en huge dildo)

Petra the hardcore anal slut (incl dap tap fist en huge dildo)

xHamster 1 month ago

Liam Jacobson Private Show

Liam Jacobson Private Show

Flirt4Free 4 months ago

Milf Breeder - part 3 - Gloryhole With A Massive Dick by Foxie2K

Milf Breeder - part 3 - Gloryhole With A Massive Dick by Foxie2K

xHamster 6 months ago

FUTA LOVES YOU HARDER: Strap-on POV | MahoganyQen

59% HD 0:10 / 7:28

FUTA LOVES YOU HARDER: Strap-on POV | MahoganyQen

LoyalFans 4 months ago

Messy Sissy Puppy Training Fuck Machine Deepthroat, Spit Drinking & Solo Anal

Messy Sissy Puppy Training Fuck Machine Deepthroat, Spit Drinking & Solo Anal

xHamster 3 weeks ago

Tease You with My New Louboutins

62% 4K 2:00 / 2:50

Tease You with My New Louboutins

Flirt4Free 10 months ago

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

Slender Trans Autumn Rain Warms Up Her Ass With Bareback

xHamster 2 years ago

Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!

Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!

xHamster 1 year ago

@VonMadeHaNut “ Sissy White Construction Worker ”

@VonMadeHaNut “ Sissy White Construction Worker ”

2BGay 2 years 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 1 month ago

I ravaged the trans girl protection-free-for-all and hoisted her off the ground with my forearm inwards her backside - Christmas Exclusive

I ravaged the trans girl protection-free-for-all and hoisted her off the ground with my forearm inwards her backside - Christmas Exclusive

Tranny.one 1 month ago

Kitty training her ass

Kitty training her ass

Tranny.one 11 months ago

Relent to Your Trans Mistress

Relent to Your Trans Mistress

xHamster 2 weeks ago

Heather: Femme Tour

Heather: Femme Tour

4Gay 1 year ago

HOT Orgasms and CumShots Compilation

HOT Orgasms and CumShots Compilation

Pornzona 3 days ago

The Fresh Cutie - Natile Mars Ella Hollywood Sissy Disciplined by Mz Berlin and Lexi Sindel

The Fresh Cutie - Natile Mars Ella Hollywood Sissy Disciplined by Mz Berlin and Lexi Sindel

SortPorn 3 years ago

Sissy Feminization

Sissy Feminization

xHamster 2 years ago

DRINK 22 CUMSHOTS - Gay BDSM Slave Training

DRINK 22 CUMSHOTS - Gay BDSM Slave Training

xHamster 1 year ago

Sissy bitch gets pegged and their tiny pathetic pushed inside of her

Sissy bitch gets pegged and their tiny pathetic pushed inside of her

xHamster 9 months ago

Lost Another Cuck Bet

58% HD 0:10 / 9:15

Lost Another Cuck Bet

LoyalFans 4 months ago

Blindfolded sissy slut training

Blindfolded sissy slut training

xHamster 1 year ago

mistress mercer and raven pantyhose chastity sissy gets pegged

mistress mercer and raven pantyhose chastity sissy gets pegged

TransDoe 2 years ago

Jhordy & Maxx Private Show

61% HD 2:00 / 24:38

Jhordy & Maxx Private Show

Flirt4Free 7 months ago

YOU’RE NOT GAY - YOU JUST LOVE DICK

YOU’RE NOT GAY - YOU JUST LOVE DICK

LoyalFans 3 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 years ago

Trying New Fist Dildo and Get Fucked and Fisted

62% HD 0:39 / 38:48

Trying New Fist Dildo and Get Fucked and Fisted

FapHouse 1 year ago

Feelipe & Adara Private Show

53% HD 2:00 / 8:50

Feelipe & Adara Private Show

Flirt4Free 6 months ago

Big ass Trans Girl in Halloween Cosplay Fucked by Big Dildos and Gets a Creampie

Big ass Trans Girl in Halloween Cosplay Fucked by Big Dildos and Gets a Creampie

xHamster 5 months ago

Doe Cosplay | Masturbation Without Panties

Doe Cosplay | Masturbation Without Panties

Flirt4Free 3 months ago

Sissy Stacy Lady in Red Part 1

59% 1:01 / 18:19

Sissy Stacy Lady in Red Part 1

FapHouse 5 months ago

New Big Fake Tits for Slutty Crossdresser

58% HD 1:01 / 5:11

New Big Fake Tits for Slutty Crossdresser

FapHouse 2 years ago

Sissy Anal Training by Latex Dommes

66% 0:39 / 10:39

Sissy Anal Training by Latex Dommes

FapHouse 9 months ago

Pt3: Beautiful Classy Tgirl Trains Her Hole

Pt3: Beautiful Classy Tgirl Trains Her Hole

ShemaleSex 2 months ago

Chastity fag slave humiliation pet play bondage

Chastity fag slave humiliation pet play bondage

xHamster 2 months ago

Sophia Loreen Private Show

HD 2:00 / 29:16

Sophia Loreen Private Show

Flirt4Free 3 years ago

Sissy training for your feminization

49% HD 1:01 / 7:27

Sissy training for your feminization

FapHouse 2 years ago

November 2025 Video Trailers - Katy Churchill farting, pissing, balloons, simp, smoking, facesitting

November 2025 Video Trailers - Katy Churchill farting, pissing, balloons, simp, smoking, facesitting

xHamster 4 months ago

Sissy Hard-On Breezy in Innocence Pummels Self Before Jizm Shot

Sissy Hard-On Breezy in Innocence Pummels Self Before Jizm Shot

TrannyGem 10 months ago

Jamer & Owen & Hercules Private Show

48% HD 2:00 / 10:23

Jamer & Owen & Hercules Private Show

Flirt4Free 3 years ago

Lyndon F Private Show

Lyndon F Private Show

Flirt4Free 3 weeks ago

if you caught me like this in the guest room

if you caught me like this in the guest room

TransTube.tv 1 year ago

this babemale Ariel trains guy Mmm

this babemale Ariel trains guy Mmm

TrannyGem 6 years ago

Gurl Sissy Blowjob and Anal Training

Gurl Sissy Blowjob and Anal Training

AbTranny 6 years ago

Sissy ass fucking smash in the bathtub

Sissy ass fucking smash in the bathtub

TrannyGem 1 day ago

full ritual POV mistress peg her sub unlock edge slap and relock again denying his release.

full ritual POV mistress peg her sub unlock edge slap and relock again denying his release.

xHamster 3 weeks ago

Kendall Penny Gives Throat Training

Kendall Penny Gives Throat Training

Nuvid 1 month ago

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

57% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

LoyalFans 4 months ago

Getting close to Node on Monstrous Bad Dragon Rex

Getting close to Node on Monstrous Bad Dragon Rex

4Gay 4 months ago

Boxing Trainer Gets Trained by Janny

53% HD 0:39 / 29:45

Boxing Trainer Gets Trained by Janny

FapHouse 6 months ago

Glamgurlxoxo: Sissy CD gives Wet BJ and Swallow Hot Cum Load from Young Guy

Glamgurlxoxo: Sissy CD gives Wet BJ and Swallow Hot Cum Load from Young Guy

TrannyGem 5 years ago

Hana Rouse Private Show

44% 4K 2:00 / 24:45

Hana Rouse Private Show

Flirt4Free 4 months ago

college-aged lad attempt his assfucking to sqiurt and shrieking for the first-ever time

college-aged lad attempt his assfucking to sqiurt and shrieking for the first-ever time

2BGay 7 months ago

Trans on a Fuckmachine for Her Neighbor

Trans on a Fuckmachine for Her Neighbor

xHamster 6 months ago

Tiny Dick Sissy Femboy Piss in Condom Drink It Masturbate and Cum Like a Little Slut

HD 0:39 / 25:36

Tiny Dick Sissy Femboy Piss in Condom Drink It Masturbate and Cum Like a Little Slut

FapHouse 1 month ago

Viky & Master Private Show

55% HD 2:00 / 9:05

Viky & Master Private Show

Flirt4Free 3 months ago

2 Mates Plumbed Me So Rock-hard Intensively Today. I Sensed Enjoy with Them & Their Spunk Explosions

2 Mates Plumbed Me So Rock-hard Intensively Today. I Sensed Enjoy with Them & Their Spunk Explosions

Gayhub 5 months ago

The Ultimate Chastity Cage Review and Guide Video

The Ultimate Chastity Cage Review and Guide Video

xHamster 2 weeks ago

Sissy caged fucking her ass with BBC

Sissy caged fucking her ass with BBC

xHamster 1 year ago

女装OLアナル調教(1/4)

女装OLアナル調教(1/4)

GayCK 3 years ago

Atakan Ali Private Show

67% HD 2:00 / 6:07

Atakan Ali Private Show

Flirt4Free 1 year ago

A Slut in a Grove (june 29, 2025) Looking for Sperm. French Transvestite Exhibition Vanessabitchx

A Slut in a Grove (june 29, 2025) Looking for Sperm. French Transvestite Exhibition Vanessabitchx

xHamster 8 months ago

milf trans submissa apanhando nas bolas e bebendo mijo

56% 4:00 / 8:41

milf trans submissa apanhando nas bolas e bebendo mijo

PissVids 1 year ago

Satin Fetish: Hot Masturbation Game, Cum on My Skirt, Lady Victoria Valente

63% HD 0:39 / 16:06

Satin Fetish: Hot Masturbation Game, Cum on My Skirt, Lady Victoria Valente

FapHouse 2 months ago

Sissy training oral-job with a Realdick toy

Sissy training oral-job with a Realdick toy

ShemaleSin 11 months ago

How to Become a Good Girl Sucking Lesson Jobs Interview

66% HD 1:01 / 7:41

How to Become a Good Girl Sucking Lesson Jobs Interview

FapHouse 3 weeks ago

Lyndon F Private Show

HD 2:00 / 24:42

Lyndon F Private Show

Flirt4Free 3 days ago

AB112 Maid human fucktoy training - squirting,cumshot (Chinese and English subtitles)

AB112 Maid human fucktoy training - squirting,cumshot (Chinese and English subtitles)

xHamster 1 year ago

Spectacular moment from "Crossdresser Rough anal fuck with rock hard red monster dildo"

Spectacular moment from "Crossdresser Rough anal fuck with rock hard red monster dildo"

xHamster 7 months ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 1

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 1

xHamster 1 month ago

Threesome Caged Sucker Gets His Ass Destroyed and Swallows My Cum

Threesome Caged Sucker Gets His Ass Destroyed and Swallows My Cum

xHamster 9 months ago

Lola Crystals (TrulyByL) gets BIG BLACK COCK special from Ali Da Reaper on Dark-hued Friday

Lola Crystals (TrulyByL) gets BIG BLACK COCK special from Ali Da Reaper on Dark-hued Friday

TransTube.tv 1 year ago

Sissy instructing: how to spunk in innocence? Rail ever thicker faux-cocks to sissygasm

Sissy instructing: how to spunk in innocence? Rail ever thicker faux-cocks to sissygasm

TrannyGem 4 years ago

Sasha De Sade Sissy Factory Tranny Slave Trained To Be A Sissy Whore

Sasha De Sade Sissy Factory Tranny Slave Trained To Be A Sissy Whore

Pornzona 2 days ago

Twinkerbell Pegging the Lost Femboi in Chastity

Twinkerbell Pegging the Lost Femboi in Chastity

xHamster 1 year ago

cherry and i dominate our disobedient puppies nyxi and livi

48% HD 0:30 / 33:02

cherry and i dominate our disobedient puppies nyxi and livi

PornBox 1 year ago

Sissy gasm time

Sissy gasm time

xHamster 1 month ago

Amannda Skye Party on Feb 13, 2026

63% 4K 2:00 / 4:00:00+

Amannda Skye Party on Feb 13, 2026

Flirt4Free 1 month ago

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

62% HD 1:01 / 11:01

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

FapHouse 1 year ago

Oliver Whitee Party on Mar 20, 2026

Oliver Whitee Party on Mar 20, 2026

Flirt4Free 3 days ago

Two Shemale And One Girl Wrestling Training Turns In To Anal Sex Creampie Threesome Fun

Two Shemale And One Girl Wrestling Training Turns In To Anal Sex Creampie Threesome Fun

xHamster 1 week ago

Take this fuckin' test and witness if you're a sissy (FEMINIZATION ROLEPLAY - AI GENERATED)

Take this fuckin' test and witness if you're a sissy (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 9 months ago

How's the Cumshot From Your Angle Zack?

45% HD 0:39 / 6:30

How's the Cumshot From Your Angle Zack?

FapHouse 6 months ago

Mistress Plays with Her Futanari Dolls

55% 0:39 / 41:16

Mistress Plays with Her Futanari Dolls

FapHouse 9 months ago

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