Training Videos - Trans (88,019)

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 1 week ago

Brie Lovely Trains to Be a Slut

HD 0:39 / 31:25

Brie Lovely Trains to Be a Slut

FapHouse 2 months ago

Sissy in pants trains her booty for BBC

Sissy in pants trains her booty for BBC

ShemaleSin 1 year ago

Luke Hardy & Cristian Ford Private Show

HD 2:00 / 16:28

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Master & Ithan & Aleex Private Show

57% HD 2:00 / 4:59

Master & Ithan & Aleex Private Show

Flirt4Free 7 months ago

Sissy Maid Strokefest - With Effects

60% HD 0:10 / 14:23

Sissy Maid Strokefest - With Effects

LoyalFans 1 year ago

Cutie-pie Florence Loves Humiliation

Cutie-pie Florence Loves Humiliation

FapHouse 1 year ago

Juanita Swan Private Show

Juanita Swan Private Show

Flirt4Free 2 years ago

Master Collins Private Show

HD 2:00 / 15:37

Master Collins Private Show

Flirt4Free 1 month ago

Using your hole while you call me Mommy and ask for more like a Good Boy!

Using your hole while you call me Mommy and ask for more like a Good Boy!

xHamster 4 months ago

Leather Crossdresser Sissy trains his hole to the max

Leather Crossdresser Sissy trains his hole to the max

xHamster 8 months ago

Valery Brett Private Show

HD 2:00 / 11:06

Valery Brett Private Show

Flirt4Free 1 year ago

Sissy Cumslut Training

Sissy Cumslut Training

xHamster 1 year ago

Sucking My ass Juice Off My Finger & Squirting In Your Face

Sucking My ass Juice Off My Finger & Squirting In Your Face

xHamster 4 years ago

SexyGirlStephanieJames - Training to stretch my anus

SexyGirlStephanieJames - Training to stretch my anus

aShemaleTube 1 month ago

Luccas & Jhordy Private Show

Luccas & Jhordy Private Show

Flirt4Free 2 months ago

Self-training No. 37: Daily Morning Exposure Walk in Stockings Only

HD 0:39 / 24:26

Self-training No. 37: Daily Morning Exposure Walk in Stockings Only

FapHouse 2 months ago

Elias & Elix Private Show

62% HD 2:00 / 3:59

Elias & Elix Private Show

Flirt4Free 4 months ago

DOMME WIFE TURNS YOU INTO A LIVE IN SISSYMAID MIND FUCK - Sissy Slut Training

DOMME WIFE TURNS YOU INTO A LIVE IN SISSYMAID MIND FUCK - Sissy Slut Training

Clips4sale 5 months ago

Valery Brett Private Show

Valery Brett Private Show

Flirt4Free 1 year ago

Valery Brett Private Show

HD 2:00 / 10:44

Valery Brett Private Show

Flirt4Free 1 year ago

Valery Brett Private Show

Valery Brett Private Show

Flirt4Free 1 year ago

Daisy Dane Private Show

Daisy Dane Private Show

Flirt4Free 2 years ago

Dick Drone Reborn: Total Identity Wipe

Dick Drone Reborn: Total Identity Wipe

Clips4sale 2 months ago

Jef Evans Private Show

Jef Evans Private Show

Flirt4Free 1 year ago

Unexperienced Sissy breezy fellate that big black cock and got butt total rock hard poked

Unexperienced Sissy breezy fellate that big black cock and got butt total rock hard poked

Gayhub 9 months ago

Alice Kizar Private Show

4K 2:00 / 12:13

Alice Kizar Private Show

Flirt4Free 6 days ago

Rough prostate massage with hottest cumshot for twink femboy

Rough prostate massage with hottest cumshot for twink femboy

xHamster 1 year ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 4 months ago

Sandy-Haired Sissy Fellates Fake Penis and Self-Facial Cumshot on Web Cam

Sandy-Haired Sissy Fellates Fake Penis and Self-Facial Cumshot on Web Cam

TrannyGem 5 months ago

Drei spezielle Dates!

53% HD 0:10 / 18:49

Drei spezielle Dates!

LoyalFans 1 year ago

Bastian Maalouf Private Show

Bastian Maalouf Private Show

Flirt4Free 3 years ago

Serving Mistress

Serving Mistress

xHamster 3 weeks ago

Dreamscape Sissy training

Dreamscape Sissy training

Sheshaft 3 years ago

My husband ejaculates in his chastity cage

My husband ejaculates in his chastity cage

xHamster 4 months ago

Hanna Ven Private Show

HD 2:00 / 11:03

Hanna Ven Private Show

Flirt4Free 1 year ago

Sissy Heels ASMR - Dominant Makes U Walk SISSY TRAINING ASMR JOI

Sissy Heels ASMR - Dominant Makes U Walk SISSY TRAINING ASMR JOI

ShemaleSin 1 day ago

Caged - Pantied - Plugged

HD 0:15 / 11:59

Caged - Pantied - Plugged

Clips4sale 2 years ago

Crhistian & Dereckk & Friends Private Show - Part 2

Crhistian & Dereckk & Friends Private Show - Part 2

Flirt4Free 7 years ago

Blowjob on the Patio

HD 0:28 / 12:38

Blowjob on the Patio

Clips4sale 4 years ago

Juanita Swan Private Show

Juanita Swan Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Aug 2, 2025 - Part 2

HD 2:00 / 23:17

Sophia Loreen Party on Aug 2, 2025 - Part 2

Flirt4Free 7 months ago

Vibrator Ruining in Nylon Catsuit

68% HD 0:10 / 14:52

Vibrator Ruining in Nylon Catsuit

Clips4sale 4 years ago

Lukas Jonsss Private Show

55% 4K 2:00 / 8:53

Lukas Jonsss Private Show

Flirt4Free 5 months ago

Mrs Nara Sissification Training - Complete: A one-way trip from Boy to Slut (720 EN-sub)

66% HD 0:47 / 50:04

Mrs Nara Sissification Training - Complete: A one-way trip from Boy to Slut (720 EN-sub)

Clips4sale 2 years ago

Sissy Humiliation Cum Countdown with TS Ria Bentley

66% 4K 0:26 / 8:47

Sissy Humiliation Cum Countdown with TS Ria Bentley

Clips4sale 2 years ago

William Raven Private Show

HD 2:00 / 10:29

William Raven Private Show

Flirt4Free 4 years ago

Sissy Dream 2

xHamster 2 years ago

Adhara Lovex & Maikol Hernandez Private Show

Adhara Lovex & Maikol Hernandez Private Show

Flirt4Free 1 year ago

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Proper Way

Premium HD 48:47

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Proper Way

Sheer 1 year ago

sissy molly deepthroat training

sissy molly deepthroat training

XXXShemalePorn 9 years 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

Vladasexytrans leaks from anal

Vladasexytrans leaks from anal

xHamster 1 year ago

Using Your Ass Like a Pussy

Premium 57% 20:19

Using Your Ass Like a Pussy

APClips 1 year ago

Sissy Slut Training 4

Sissy Slut Training 4

xHamster 4 months ago

Valery & Felipe Private Show

Valery & Felipe Private Show

Flirt4Free 1 year ago

4K - Lusty Shower Vol 18 {TEARING FEST}

4K 0:12 / 31:01

4K - Lusty Shower Vol 18 {TEARING FEST}

Clips4sale 11 months ago

Ts Isabella Coupe Anal Delights P3

Ts Isabella Coupe Anal Delights P3

xHamster 3 years ago

SISSY gurlfriend PEES her pants and pleases me until I CUM

SISSY gurlfriend PEES her pants and pleases me until I CUM

xHamster 10 months ago

Ebony nurse Kira Noir banged by femboy Jean Hollywood

Ebony nurse Kira Noir banged by femboy Jean Hollywood

Yeswegays 2 years ago

Viky & Emma Private Show

Viky & Emma Private Show

Flirt4Free 1 month ago

Sloppy Daily Anal Training

Sloppy Daily Anal Training

FapHouse 11 months ago

Sissy Task for Sissies

Sissy Task for Sissies

LoyalFans 1 year ago

Diaper Sissy Dare Games

HD 0:45 / 16:41

Diaper Sissy Dare Games

Clips4sale 4 months ago

Ashley V swallows huge dildo up her ass and rubs her tiny caged clitAshley V se traga un enorme consolador

Ashley V swallows huge dildo up her ass and rubs her tiny caged clitAshley V se traga un enorme consolador

xHamster 2 years ago

TRANSSEXUAL Willow Hammerz - BIG BLACK COCK / BNWO / SISSY PMV

TRANSSEXUAL Willow Hammerz - BIG BLACK COCK / BNWO / SISSY PMV

TrannyGem 3 years ago

SISSY ROLEMODEL

SISSY ROLEMODEL

aShemaleTube 8 years ago

TS Yasmin Lee as Cleopatra: TsSeduction Special Feature

TS Yasmin Lee as Cleopatra: TsSeduction Special Feature

C4S 2 years ago

Sissy's Night In - Chastity And Cumshots

Sissy's Night In - Chastity And Cumshots

ShemaleSin 2 years ago

FemDom POV: MISTRESSE Arya Grander Shows her SEX DOLL whilst u JERK OFF

FemDom POV: MISTRESSE Arya Grander Shows her SEX DOLL whilst u JERK OFF

ShemaleSin 4 years ago

A Very Sexy Model and Sexy Video

A Very Sexy Model and Sexy Video

Flirt4Free 7 years ago

Sissy Drilled to Anal Climax HANDSFREE CLIMAX

Sissy Drilled to Anal Climax HANDSFREE CLIMAX

ShemaleSin 2 years ago

Asian Twink Army Anal Training

Asian Twink Army Anal Training

xHamster 1 year ago

Sissy Slut Adventures Volume 2 - Jessica Dynamic

55% HD 0:29 / 14:52

Sissy Slut Adventures Volume 2 - Jessica Dynamic

Clips4sale 1 year ago

”Nathalie Mars and Ella Nova tested their new anal toys”

”Nathalie Mars and Ella Nova tested their new anal toys”

TransHero 4 years ago

Bad Girl Punished 3 mp4

Bad Girl Punished 3 mp4

Clips4sale 2 years ago

Domina spreads sissy bootie with immense schlong part-two

Domina spreads sissy bootie with immense schlong part-two

TrannyGem 1 year ago

FTM Femboy Twunk Opens Up Boypussy With trio Gigantic Fake Penises

FTM Femboy Twunk Opens Up Boypussy With trio Gigantic Fake Penises

TrannyGem 1 year ago

Roulette Sissy dare task - Poking sex-toy in naked outdoors to post online

Roulette Sissy dare task - Poking sex-toy in naked outdoors to post online

ShemaleSin 4 years ago

Valery Brett Private Show

Valery Brett Private Show

Flirt4Free 9 months ago

How Sissy Bitches Cum

HD 1:01 / 18:58

How Sissy Bitches Cum

FapHouse 2 years ago

Hanna Ven Private Show

HD 2:00 / 10:13

Hanna Ven Private Show

Flirt4Free 1 year ago

Sissy Feminization (mp4)

Sissy Feminization (mp4)

Clips4sale 7 months ago

Liam Jacobson Private Show

61% HD 2:00 / 10:02

Liam Jacobson Private Show

Flirt4Free 1 year ago

Femboy thighjobs go ULTRA-KINKY

Femboy thighjobs go ULTRA-KINKY

Gayhub 10 months 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

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 3 years ago

Bound Sissy Enjoys Her Cum

69% HD 0:14 / 15:12

Bound Sissy Enjoys Her Cum

Clips4sale 4 years 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

Sissy Dani Hard Assfuck Training PT 2 (Humid Audio) (HD)

Sissy Dani Hard Assfuck Training PT 2 (Humid Audio) (HD)

TransTube.tv 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

Ekaterina Jazmine Private Show

Ekaterina Jazmine Private Show

Flirt4Free 2 years ago

Alice Kittenn Private Show

HD 2:00 / 14:34

Alice Kittenn Private Show

Flirt4Free 1 year ago

Bnwo - Your Whiteboy Future

Bnwo - Your Whiteboy Future

Clips4sale 9 months 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

Hanna Ven Private Show

Hanna Ven Private Show

Flirt4Free 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

Anal Update two: Princess Edition!

Anal Update two: Princess Edition!

ShemaleSin 1 year ago

Sissy leaves chastity key on a public footpath

Sissy leaves chastity key on a public footpath

ShemaleSin 1 year ago

Aliyah Millers Private Show

Aliyah Millers Private Show

Flirt4Free 1 month 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

Gagged Sissy Loves Drooling

70% HD 0:10 / 13:16

Gagged Sissy Loves Drooling

Clips4sale 4 years ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 1 week ago

Gay porn addiction programming mov

63% 0:11 / 6:07

Gay porn addiction programming mov

Clips4sale 2 years 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

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

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

Ekaterina Jazmine Private Show

66% 4K 2:00 / 4:44

Ekaterina Jazmine Private Show

Flirt4Free 7 months ago

Will Sin Strips and Plays with Herself

Will Sin Strips and Plays with Herself

aShemaleTube 3 months ago

Sissy screwing

ShemaleSin 1 month 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

Submissive Tgirl Suffers Mindfuck Electric Shock Timer Game

Premium HD 24:56

Submissive Tgirl Suffers Mindfuck Electric Shock Timer Game

xnxxGold 11 months ago

Sissy in flat chastity cage HD

Sissy in flat chastity cage HD

ShemaleSin 4 years 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

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

Thrilling moment from "Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical"

Thrilling moment from "Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical"

xHamster 5 months ago

Patric & Oliver Private Show

63% HD 2:00 / 14:54

Patric & Oliver Private Show

Flirt4Free 3 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

Chastity fox ninja cosplay and biggest anal sex-toy destruction

Chastity fox ninja cosplay and biggest anal sex-toy destruction

ShemaleSin 3 months ago

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