Training Videos - Trans (88,046)

Liam Jacobson Private Show

61% HD 2:00 / 10:02

Liam Jacobson Private Show

Flirt4Free 1 year ago

trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity

trans sissy slut with blue hair going crazy with big dildos - MercurySissy aka Mercury Montana riding and training in chastity

xHamster 1 year ago

Sexy Trans Cutie Fucked in Every Room of the House by TS Honey - Sexy Trans Lesbian Sex

Sexy Trans Cutie Fucked in Every Room of the House by TS Honey - Sexy Trans Lesbian Sex

PornFreeNow 4 months ago

Aliyah Millers Private Show

Aliyah Millers Private Show

Flirt4Free 1 month ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 4 years ago

Being a DIK Part 2 Gameplay by LoveSkySan69

Being a DIK Part 2 Gameplay by LoveSkySan69

xHamster 1 year ago

tiny little dick tranny fucking her ass with a fuck machine - sisssy trainning

Premium HD 8:54

tiny little dick tranny fucking her ass with a fuck machine - sisssy trainning

Sheer 1 year ago

Big Booty Femboy Cock Lover Desperately Anal Fucking Herself

Big Booty Femboy Cock Lover Desperately Anal Fucking Herself

xHamster 1 month ago

Bound Sissy Enjoys Her Cum

69% HD 0:14 / 15:12

Bound Sissy Enjoys Her Cum

Clips4sale 4 years ago

Anal Update two: Princess Edition!

Anal Update two: Princess Edition!

ShemaleSin 1 year ago

Sissy takes its cage distant during riding a massive 16 vibrator and shags the nut beyond concerning its tiny clit.

Sissy takes its cage distant during riding a massive 16 vibrator and shags the nut beyond concerning its tiny clit.

WebcamBros 1 year ago

Gagged Sissy Loves Drooling

70% HD 0:10 / 13:16

Gagged Sissy Loves Drooling

Clips4sale 4 years ago

Sissy leaves chastity key on a public footpath

Sissy leaves chastity key on a public footpath

ShemaleSin 1 year ago

Hanna Ven Private Show

Hanna Ven Private Show

Flirt4Free 1 year ago

Pathetic sissy boi gets bent over the car and pegged in his tight little ass

Pathetic sissy boi gets bent over the car and pegged in his tight little ass

xHamster 11 months ago

Gay Task for Sissy Goon – Bisexual Encouragement by Goddess Nikki Kit

62% HD 0:25 / 8:27

Gay Task for Sissy Goon – Bisexual Encouragement by Goddess Nikki Kit

Clips4sale 1 year ago

Whispering Anal Training and Public Play - Your Ultimate ASMR Dream

Whispering Anal Training and Public Play - Your Ultimate ASMR Dream

ShemaleSin 9 months ago

Brutus K Private Show

HD 2:00 / 11:40

Brutus K Private Show

Flirt4Free 6 years ago

Gay porn addiction programming mov

63% 0:11 / 6:07

Gay porn addiction programming mov

Clips4sale 2 years ago

Dancing and Teasing in a Tight Business Shirt

HD 2:00 / 48:00

Dancing and Teasing in a Tight Business Shirt

Flirt4Free 1 year ago

Bnwo - Your Whiteboy Future

Bnwo - Your Whiteboy Future

Clips4sale 9 months ago

Anouk - Sissy Instructing in Harsh Condom-Free Assfuck and Rock Hard Gargle and Facefuck - Total Flick

Anouk - Sissy Instructing in Harsh Condom-Free Assfuck and Rock Hard Gargle and Facefuck - Total Flick

TrannyGem 3 years ago

Sissy screwing

ShemaleSin 1 month ago

Will Sin Strips and Plays with Herself

Will Sin Strips and Plays with Herself

aShemaleTube 3 months ago

Wife Sissifies You - Sissy Training with Rebelle Hart

50% 0:25 / 16:59

Wife Sissifies You - Sissy Training with Rebelle Hart

Clips4sale 1 year ago

Cum and do a Jerk Off and Room Tour With Me!

Cum and do a Jerk Off and Room Tour With Me!

Clips4sale 2 years ago

Ekaterina Jazmine Private Show

66% 4K 2:00 / 4:44

Ekaterina Jazmine Private Show

Flirt4Free 7 months ago

Submissive Tgirl Suffers Mindfuck Electric Shock Timer Game

Premium HD 24:56

Submissive Tgirl Suffers Mindfuck Electric Shock Timer Game

xnxxGold 11 months ago

Sophia Loreen Party on Jan 31, 2026 - Part 2

4K 2:00 / 31:36

Sophia Loreen Party on Jan 31, 2026 - Part 2

Flirt4Free 1 month ago

女主训练她的变装奴隶 Femdom Slave Training - Chinese Femdom

女主训练她的变装奴隶 Femdom Slave Training - Chinese Femdom

AbTranny 5 years ago

Sissy in flat chastity cage HD

Sissy in flat chastity cage HD

ShemaleSin 4 years ago

Roughly spanked and screwed cd hubby on a thrashing bench during the time that in slavery

Roughly spanked and screwed cd hubby on a thrashing bench during the time that in slavery

ShemaleSin 3 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 4 months ago

Patric & Oliver Private Show

63% HD 2:00 / 14:54

Patric & Oliver Private Show

Flirt4Free 3 years ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

Guy Feminized into Goth Girl Gets Fucked by Dominatrix

Guy Feminized into Goth Girl Gets Fucked by Dominatrix

xHamster 2 years ago

Luciana Sainz Private Show

4K 2:00 / 13:22

Luciana Sainz Private Show

Flirt4Free 1 day ago

Tiffanny Lombardi Private Show

66% HD 2:00 / 4:26

Tiffanny Lombardi Private Show

Flirt4Free 2 years ago

Mexican Sissy Crossdresser Deep throats Uncut Trinidadian Wood

Mexican Sissy Crossdresser Deep throats Uncut Trinidadian Wood

TransTube.tv 1 year ago

Dick Drone Reborn: Total Identity Wipe

Dick Drone Reborn: Total Identity Wipe

Clips4sale 2 months ago

Roxy Park Private Show

Roxy Park Private Show

Flirt4Free 5 years ago

Pegged in Pink - Sissy Pegging POV

Pegged in Pink - Sissy Pegging POV

xHamster 2 years ago

Little Pony Sissy Wore Suit of Leopard and Dancing Showing Her Sexy Body

Little Pony Sissy Wore Suit of Leopard and Dancing Showing Her Sexy Body

FapHouse 2 years ago

Indian Gay Crossdresser Bottom Pressing and Playing with Her Big Boobs in Red Gown Real Homemade Sex

Indian Gay Crossdresser Bottom Pressing and Playing with Her Big Boobs in Red Gown Real Homemade Sex

xHamster 3 weeks ago

Rectal Instructing Sadee Man meat-squashing Chocolate-colored-eye Outside Putting 8 inches Up Her Rump For 1st Time

Rectal Instructing Sadee Man meat-squashing Chocolate-colored-eye Outside Putting 8 inches Up Her Rump For 1st Time

TransTube.tv 1 year ago

Ass Stretching Until Is Breaks!

Ass Stretching Until Is Breaks!

xHamster 11 months ago

Sissy Kanisa Crossdresser Maid Service Part 2 Dress up

Sissy Kanisa Crossdresser Maid Service Part 2 Dress up

xHamster 1 year ago

PANTYHOSE WEARING SISSY SLUT TRANCE

63% 4K 0:25 / 20:47

PANTYHOSE WEARING SISSY SLUT TRANCE

Clips4sale 3 years ago

My New Maid

Clips4sale 3 years ago

PUSHING 25 CM INTO A HUNK VAGINA

PUSHING 25 CM INTO A HUNK VAGINA

ShemaleSin 5 months ago

Alice Kittenn Private Show

Alice Kittenn Private Show

Flirt4Free 1 year ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 year ago

Prostate Play Squirting & Creaming

Prostate Play Squirting & Creaming

ShemaleSin 1 year ago

my throat gets stuck and my eyes roll and you unload your milk.. #AHEGAO/BLOWJOB/CUMMING TOY#

53% HD 2:00 / 4:51

my throat gets stuck and my eyes roll and you unload your milk.. #AHEGAO/BLOWJOB/CUMMING TOY#

Flirt4Free 2 years ago

Dressing Sissies For Real Men To Mock (HD MP4)

66% 4K 0:31 / 15:17

Dressing Sissies For Real Men To Mock (HD MP4)

Clips4sale 5 months ago

Rebeccah Gibson Private Show

HD 2:00 / 24:18

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

Luisa Martinez Private Show

HD 2:00 / 16:16

Luisa Martinez Private Show

Flirt4Free 2 years ago

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

xHamster 8 months ago

Felipe Guzman Private Show

HD 2:00 / 18:57

Felipe Guzman Private Show

Flirt4Free 1 year ago

Estrogen Encouragement

Estrogen Encouragement

Clips4sale 11 months ago

Mateo Campbell Private Show

HD 2:00 / 35:04

Mateo Campbell Private Show

Flirt4Free 2 years ago

”Coach Jeremiah Jones trains Zacc Andrews how to endure anal”

”Coach Jeremiah Jones trains Zacc Andrews how to endure anal”

TransHero 3 months ago

Gay For Ass Worship

Gay For Ass Worship

Clips4sale 3 years ago

S3 EP1 HOPELESS STRAIGHT MARRIED MAN EATING SHEMALE ASSPUSSY ON SLING

HD 0:20 / 10:09

S3 EP1 HOPELESS STRAIGHT MARRIED MAN EATING SHEMALE ASSPUSSY ON SLING

Clips4sale 2 years ago

Princesses Ysphere 2 - Magical Hentai Girls Trained To Be Sex Slaves With Rough Sex

Princesses Ysphere 2 - Magical Hentai Girls Trained To Be Sex Slaves With Rough Sex

11Hentai 2 months ago

Sissy training: how to cum in chastity? Ride ever larger dildos to sissygasm

Sissy training: how to cum in chastity? Ride ever larger dildos to sissygasm

ShemaleSin 4 years ago

Wannabe Famous Sissy Faggot in pink!

Wannabe Famous Sissy Faggot in pink!

xHamster 11 months ago

sissy chick trainer rail it professional for papi

sissy chick trainer rail it professional for papi

TrannyGem 3 years ago

Mistress Seven's Dirty Little Whore (MP4)

Mistress Seven's Dirty Little Whore (MP4)

Clips4sale 7 months ago

Big Cock in Sweet Pussy

53% 4K 2:00 / 13:17

Big Cock in Sweet Pussy

Flirt4Free 6 months ago

need masters and mistress

need masters and mistress

xHamster 2 months ago

Slutty Sissy Spitroast with Miss Lady Louisa

66% HD 1:01 / 20:22

Slutty Sissy Spitroast with Miss Lady Louisa

FapHouse 11 months ago

Watch mixyxxx get spitted by two massive dildos in her sexy lingerie and high heels

Watch mixyxxx get spitted by two massive dildos in her sexy lingerie and high heels

TrannyMovs 6 months ago

Alice Summertale Private Show

Alice Summertale Private Show

Flirt4Free 4 days ago

submissive skinny ladyboy anal casting & slave training - xdominant

57% HD 0:29 / 28:48

submissive skinny ladyboy anal casting & slave training - xdominant

AnalVids 1 year ago

Mistressxxx Is Here for You

59% HD 1:01 / 5:08

Mistressxxx Is Here for You

FapHouse 1 year ago

large collection of all femboy anal penetrations from 2025.

large collection of all femboy anal penetrations from 2025.

ShemaleSin 2 months ago

Sissy Husband Dressed in Pink, Pegged & Fed Him Own Cum!

74% HD 1:01 / 22:24

Sissy Husband Dressed in Pink, Pegged & Fed Him Own Cum!

FapHouse 6 months ago

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

FapHouse 1 year ago

Sissy Dress up humiliation part 1 - Everything pink, satin & frilly

Premium HD 16:25

Sissy Dress up humiliation part 1 - Everything pink, satin & frilly

Clips4sale 3 years ago

Ekaterina Jazmine Private Show

HD 2:00 / 10:20

Ekaterina Jazmine Private Show

Flirt4Free 2 years ago

Threesome Sissy Domination

Threesome Sissy Domination

xHamster 3 months ago

SKINNY SUBMISSIVE LADYBOY ANAL CASTING &amp_ SLAVE TRAINING

Premium HD 23:16

SKINNY SUBMISSIVE LADYBOY ANAL CASTING &amp_ SLAVE TRAINING

xnxxGold 6 months ago

Rubber doll deep throat training

Rubber doll deep throat training

XXXShemalePorn 9 years ago

Sissy Sph: Micropenis Fails Toilet Paper Roll Test

51% HD 0:39 / 5:14

Sissy Sph: Micropenis Fails Toilet Paper Roll Test

FapHouse 2 years ago

Weak for Tranny's Cock and Sperm

Premium HD 11:59

Weak for Tranny's Cock and Sperm

Clips4sale 4 years ago

”Diesel Ravaged Me!”

”Diesel Ravaged Me!”

TransHero 2 months ago

Fisting Between Friends 2: Trans Dominatrix Fists Trans submissive in Anal Gape

61% 0:28 / 16:49

Fisting Between Friends 2: Trans Dominatrix Fists Trans submissive in Anal Gape

Clips4sale 7 months ago

I Accidentally Turned Into a Trans Bimbo

66% 0:30 / 10:48

I Accidentally Turned Into a Trans Bimbo

Clips4sale 1 year ago

Isabella Pearson Private Show

Isabella Pearson Private Show

Flirt4Free 5 months ago

Sakura's Training (By Afrobull)

Sakura's Training (By Afrobull)

ShemaleSin 2 weeks ago

Ambar Collins Private Show

Ambar Collins Private Show

Flirt4Free 1 year ago

Nessa M Private Show

HD 2:00 / 16:38

Nessa M Private Show

Flirt4Free 6 years ago

German Teen tranny fucks her ass in dirndl with dildo

German Teen tranny fucks her ass in dirndl with dildo

xHamster 1 year ago

Tsunade Naruto Boruto Xtreme sex Anime Hentai Cartoon cum spooning creampie tits kunoichi trainer

Tsunade Naruto Boruto Xtreme sex Anime Hentai Cartoon cum spooning creampie tits kunoichi trainer

HentaiGem 1 year ago

Huge 9in Dildo Fucking Compilation Vol.5

Huge 9in Dildo Fucking Compilation Vol.5

aShemaleTube 7 months ago

Slave doll training for its Mistress

Slave doll training for its Mistress

xHamster 1 month ago

Sophia Loreen Pillow Cowgirl Ride

HD 2:00 / 11:08

Sophia Loreen Pillow Cowgirl Ride

Flirt4Free 2 years ago

Sissies are Made to be Servants

54% HD 0:30 / 11:06

Sissies are Made to be Servants

Clips4sale 9 months ago

Sissy Housemaid Application / Sissy Dienstmädchen Bewerbung bei Mistress Susi im Hause

62% HD 0:10 / 7:43

Sissy Housemaid Application / Sissy Dienstmädchen Bewerbung bei Mistress Susi im Hause

LoyalFans 3 years ago

FULL Sissy Mara Jade's Riding Compilation

FULL Sissy Mara Jade's Riding Compilation

ShemaleSin 3 years ago

4K - Lusty Shower Vol4

4K 0:19 / 18:29

4K - Lusty Shower Vol4

Clips4sale 3 years ago

Seduced By Silk - Star Nine Mobile

59% 0:17 / 13:40

Seduced By Silk - Star Nine Mobile

Clips4sale 2 years ago

BODY SWAP LATEX CATSUIT ORGASM

HD 0:39 / 13:19

BODY SWAP LATEX CATSUIT ORGASM

Clips4sale 7 months ago

Anal dressage d'un amateur crossdresser

Anal dressage d'un amateur crossdresser

Xfeed 1 year ago

Your Wife’s White Cunt Is Worthless Next to Black Dick

HD 0:30 / 35:00

Your Wife’s White Cunt Is Worthless Next to Black Dick

Clips4sale 1 month ago

Sexy Shamle Jessica Bloom&#039_s Sissy Slut Academy Introduction Interview (Full)

Premium HD 30:30

Sexy Shamle Jessica Bloom&#039_s Sissy Slut Academy Introduction Interview (Full)

XVideosRed 3 years ago

You Suck For Mistress Jasmin 4k

4K 0:30 / 10:00

You Suck For Mistress Jasmin 4k

Clips4sale 1 year ago

Prison or a Sissy Diaper Ballerina

52% 0:30 / 16:26

Prison or a Sissy Diaper Ballerina

Clips4sale 6 months ago

Golden-Haired T-hotty Trains Herr Booty on Her Screw Machione

Golden-Haired T-hotty Trains Herr Booty on Her Screw Machione

ShemaleSin 3 years ago

Mistress Femdom Handjob For Crossdresser Sissy

Mistress Femdom Handjob For Crossdresser Sissy

Eporner 6 years ago

The Sissy Toy of the Goddess

65% HD 1:01 / 14:37

The Sissy Toy of the Goddess

FapHouse 1 year ago

Nahuel Jonnes Feature Show

HD 2:00 / 52:50

Nahuel Jonnes Feature Show

Flirt4Free 5 years ago

FRENCH-AMERICAN BAREBACK ORGY: TRIPLE BLOWJOB, DEEP FISTING AND MESSY CUMSHOT IN DUNGEON

50% 0:30 / 49:55

FRENCH-AMERICAN BAREBACK ORGY: TRIPLE BLOWJOB, DEEP FISTING AND MESSY CUMSHOT IN DUNGEON

Clips4sale 8 months ago

MILF Mistress Fucks and Peggs Her Polish Sissy

HD 1:01 / 10:57

MILF Mistress Fucks and Peggs Her Polish Sissy

FapHouse 1 year ago

Slut Training Of Singapore Lily With Hard Anal

Slut Training Of Singapore Lily With Hard Anal

YepTube 1 month ago

Ebony tranny training her big black dick

Ebony tranny training her big black dick

Fapcat 3 years ago

Fingering booty whilst wanking in my chair

Fingering booty whilst wanking in my chair

ShemaleSin 1 month ago

COCK IN A FROCK 7

56% 4K 0:30 / 15:22

COCK IN A FROCK 7

Clips4sale 1 year ago

European Model, Brutus Plays with His Dick

HD 2:00 / 13:07

European Model, Brutus Plays with His Dick

Flirt4Free 9 years ago

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