Training Videos - Trans (88,181)

Sissy Maid Training With Zara Durose Stage 1 (MP4)

Sissy Maid Training With Zara Durose Stage 1 (MP4)

Clips4sale 4 months ago

Chiara & Chloe Private Show

Chiara & Chloe Private Show

Flirt4Free 1 year ago

Hot Blonde Siswet Anal Training

Hot Blonde Siswet Anal Training

Tranny.one 2 years ago

The Sissy Hospital wmv

57% HD 0:29 / 8:18

The Sissy Hospital wmv

Clips4sale 1 year ago

Making a Maid

HD 0:17 / 25:16

Clips4sale 3 years ago

Femboy Craves CBT Punishment

73% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 4 years ago

Crossdressing Slave Orally and Anally Submitted - Full Version

HD 0:30 / 21:33

Crossdressing Slave Orally and Anally Submitted - Full Version

Clips4sale 1 year ago

TRANSSEXUAL W I L L O W - Sissygasm and BNWO Teaching PMV

TRANSSEXUAL W I L L O W - Sissygasm and BNWO Teaching PMV

TrannyGem 4 months ago

Diaper Prisoner Orientation for Step-Daddy

55% 0:27 / 22:36

Diaper Prisoner Orientation for Step-Daddy

Clips4sale 7 months ago

Sissified Male Suffering and Strung Up - Part 1

Sissified Male Suffering and Strung Up - Part 1

Clips4sale 1 year ago

Crossdresser Christmas Role Have Fun

Crossdresser Christmas Role Have Fun

TrannyGem 2 years ago

Hot sissy lola doll en latex noir et cheveux bleu enfourche un gros god en se touchant qualité HD

Hot sissy lola doll en latex noir et cheveux bleu enfourche un gros god en se touchant qualité HD

ShemaleSin 3 months ago

Let Me Convince You To Crossdress | Trance Loop

40% 0:30 / 7:50

Let Me Convince You To Crossdress | Trance Loop

Clips4sale 1 year ago

8K UNMASKED - Naked Girl x Cock Slapping x Cum 3 times x Cum Eating

64% 4K 0:30 / 23:09

8K UNMASKED - Naked Girl x Cock Slapping x Cum 3 times x Cum Eating

Clips4sale 1 year ago

Sissy Kara Rides Her Faux sausage For Her Hotwife

Sissy Kara Rides Her Faux sausage For Her Hotwife

Transvids.tv 1 year ago

Feminization Mantras: Sissy Mesmerize

53% 0:30 / 8:19

Feminization Mantras: Sissy Mesmerize

Clips4sale 11 months ago

Teacher Reina's Alphabet Lesson of Sexual Terms

Teacher Reina's Alphabet Lesson of Sexual Terms

xHamster 3 months ago

How to Sissy Self Feminized

How to Sissy Self Feminized

FapHouse 2 years ago

Sissygasm Precum CEI Sissy Slut Task 2 Feminization Sissification Training Blonde Femdom Mistress Emily Marilyn Encouraged Fem

59% HD 0:18 / 13:34

Sissygasm Precum CEI Sissy Slut Task 2 Feminization Sissification Training Blonde Femdom Mistress Emily Marilyn Encouraged Fem

Clips4sale 5 months ago

YOUR PATHETIC COCK SHRINKS INTO GRANNY PANTIES - CLP

57% 0:30 / 19:23

YOUR PATHETIC COCK SHRINKS INTO GRANNY PANTIES - CLP

Clips4sale 4 months ago

Sissy Compilation Chastity Forever

Sissy Compilation Chastity Forever

XVideos 4 months ago

CUM DIET

46% 0:11 / 10:13

Clips4sale 3 years ago

Part 1/4 Chastity Release After a Month: Humiliating Penetration and Degradation

47% HD 1:01 / 6:03

Part 1/4 Chastity Release After a Month: Humiliating Penetration and Degradation

FapHouse 1 year ago

FUTA ELLIE'S NEW FUCK TOY 4K - ELLIE IDOL

4K 0:26 / 21:38

FUTA ELLIE'S NEW FUCK TOY 4K - ELLIE IDOL

Clips4sale 8 months ago

Blondie TRANSSEXUAL barebacks marine

Blondie TRANSSEXUAL barebacks marine

TrannyGem 3 years ago

Sissy Charlotte deepthroat training on Mikes huge cock

Sissy Charlotte deepthroat training on Mikes huge cock

XVideos 5 months ago

New Girl in the Sissy Harem

51% HD 0:30 / 11:24

New Girl in the Sissy Harem

Clips4sale 6 months ago

Natalia Coxx in Natalia Coxx - IKillItTs

Natalia Coxx in Natalia Coxx - IKillItTs

AbTranny 9 years ago

Sasha Earth sissy whore have sex with toy

Sasha Earth sissy whore have sex with toy

XVideos 3 years ago

Sissies Belong In Chastity (HD MP4)

53% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 2 years ago

Sissy is made to serve cock

55% HD 0:30 / 10:43

Sissy is made to serve cock

Clips4sale 1 year ago

Scarlette Ray Private Show

HD 2:00 / 17:44

Scarlette Ray Private Show

Flirt4Free 2 years ago

New sissy interview Part 6 Food squelch

New sissy interview Part 6 Food squelch

Clips4sale 3 years ago

Luna Camx Private Show

HD 2:00 / 13:40

Luna Camx Private Show

Flirt4Free 3 years ago

Ekaterina Jazmine Private Show

Ekaterina Jazmine Private Show

Flirt4Free 2 months ago

Bound Stuffed and Milked - Kendra + Goddess Tangent

55% HD 0:11 / 19:01

Bound Stuffed and Milked - Kendra + Goddess Tangent

Clips4sale 4 years ago

Khalifa Gold & Lissa Hamilton Private Show

61% HD 2:00 / 5:15

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 7 months ago

Desire Sweet Private Show

63% HD 2:00 / 6:53

Desire Sweet Private Show

Flirt4Free 4 months ago

Feminizer 1 mov

50% 0:06 / 2:03

Feminizer 1 mov

Clips4sale 2 years ago

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

Training my LATEX SISSY bitch PROSTATE with my NURSE GLOVES

YouPorn Unknown

Bella Brookz Private Show

56% HD 2:00 / 26:43

Bella Brookz Private Show

Flirt4Free 2 years ago

Ronda & Joyce Private Show

Ronda & Joyce Private Show

Flirt4Free 1 year ago

Katalina Rosee Private Show

4K 2:00 / 21:38

Katalina Rosee Private Show

Flirt4Free 7 months ago

Your Girlfriend Found a BIGGER Cock - Sissy, SPH, Cucking, Futa, Bully

64% 4K 0:30 / 18:59

Your Girlfriend Found a BIGGER Cock - Sissy, SPH, Cucking, Futa, Bully

Clips4sale 1 year ago

chubby femboy fucked by a black dildo

chubby femboy fucked by a black dildo

xHamster 2 years ago

Khalifa Gold & Lissa Hamilton Private Show

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 5 months ago

A caning from Lady Krampus

A caning from Lady Krampus

Clips4sale 3 years ago

Micky Mackenzie Private Show

Micky Mackenzie Private Show

Flirt4Free 11 years ago

YOU ARE MY COCK SLUT! YOU WILL TAKE MY COCK! 15 minute AUDIO ONLY

60% HD 0:30 / 15:00

YOU ARE MY COCK SLUT! YOU WILL TAKE MY COCK! 15 minute AUDIO ONLY

Clips4sale 5 months ago

SISSY'S FIRST HIGH HEELS

SISSY'S FIRST HIGH HEELS

Clips4sale 1 year ago

Make your Appointment, Sissy

Make your Appointment, Sissy

Clips4sale 9 months ago

Inked Up H-Town Vato & Homeboy Idolize Sissy CD

Inked Up H-Town Vato & Homeboy Idolize Sissy CD

TrannyGem 4 months ago

My husbands kinky secret- 1080p

4K 0:30 / 12:52

My husbands kinky secret- 1080p

Clips4sale 1 year ago

You want to be made over? Lola Minaj Trans Gender transformation panties femdom sissy training

You want to be made over? Lola Minaj Trans Gender transformation panties femdom sissy training

Clips4sale 3 years ago

Trans Dicksucking Coach Trains You For the Blowjob Olympics

Trans Dicksucking Coach Trains You For the Blowjob Olympics

”Big round ass beauty gets a sexy sweaty workout session with a nice dick”

”Big round ass beauty gets a sexy sweaty workout session with a nice dick”

ThePornstar 9 months ago

SnowBunny Dildo Assfucking Practice

SnowBunny Dildo Assfucking Practice

Clips4sale 1 year ago

Crossdresser piss everwhere compilation

Crossdresser piss everwhere compilation

XVideos 1 year ago

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

StarWank 1 year ago

Khalifa Gold & Lissa Hamilton Private Show

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 4 months ago

P1 FARTING AIR ENEMA FETISHTRANSEXUAL by PROFESSIONAL RUGBY PLAYER

4K 0:21 / 10:28

P1 FARTING AIR ENEMA FETISHTRANSEXUAL by PROFESSIONAL RUGBY PLAYER

Clips4sale 2 years ago

Jamer & Owen & Hercules Private Show

Jamer & Owen & Hercules Private Show

Flirt4Free 3 years 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

CUM EATING CHALLENGE, CEI - Stepmom Helps You eat Cum Comfortably like A Pro, ABDL Mind Fuck

CUM EATING CHALLENGE, CEI - Stepmom Helps You eat Cum Comfortably like A Pro, ABDL Mind Fuck

Clips4sale 1 year ago

Trans Cutie Rika Fox Coarse Interracial POV

Trans Cutie Rika Fox Coarse Interracial POV

ShemaleSin 1 year ago

Katty Anderson Private Show

HD 2:00 / 11:38

Katty Anderson Private Show

Flirt4Free 4 months ago

Becoming A Sissy (JOI) w/ Raven Gray

Becoming A Sissy (JOI) w/ Raven Gray

Fapcat 3 years ago

training complete

training complete

XVideos 9 years ago

P3 FRENCH MAID IN HER FIRST DAY WORKING DEEPTHROAT HER MISTRESS BIG COCK AT THE DANGEON

HD 0:21 / 10:06

P3 FRENCH MAID IN HER FIRST DAY WORKING DEEPTHROAT HER MISTRESS BIG COCK AT THE DANGEON

Clips4sale 11 months ago

ADVANCED SISSY TRAINING BETA Volume 1 - Sissy Programming Mind Fuck, Sissification Training

ADVANCED SISSY TRAINING BETA Volume 1 - Sissy Programming Mind Fuck, Sissification Training

Clips4sale 1 year ago

Sissy Spitroast with Strap-On and Girldick

62% HD 0:30 / 15:02

Sissy Spitroast with Strap-On and Girldick

Clips4sale 4 years ago

Feelipe & Adara Private Show

58% HD 2:00 / 27:56

Feelipe & Adara Private Show

Flirt4Free 7 months ago

An amateur man&#039;s maid plays naughty with her buttocks [Personal shooting]

An amateur man&#039;s maid plays naughty with her buttocks [Personal shooting]

xHamster 1 year ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 1 year ago

Femdom Belt On Bangs Sissy Crossdresser With Climax Denial And Humiliation

Femdom Belt On Bangs Sissy Crossdresser With Climax Denial And Humiliation

BigTitsLust 4 years ago

CROSSDRESSER SUBMISSA DA BUNDA GRANDE HUMILHADA AOS PES DO MESTRE QUE A PUNE COM SOCOS

Premium HD 12:36

CROSSDRESSER SUBMISSA DA BUNDA GRANDE HUMILHADA AOS PES DO MESTRE QUE A PUNE COM SOCOS

Sheer 11 months ago

Prissy Sissy Maid Training Stage 3 (MP4)

56% 0:11 / 8:36

Prissy Sissy Maid Training Stage 3 (MP4)

Clips4sale 1 year ago

sissypov - linda moon her sissy dreams have come true

sissypov - linda moon her sissy dreams have come true

TransDoe 2 years ago

Futanari Pegging BJ Food Humiliation HD

55% HD 0:20 / 18:34

Futanari Pegging BJ Food Humiliation HD

Clips4sale 3 years ago

Bisexual Instructions 1 720p

Bisexual Instructions 1 720p

Clips4sale 2 months ago

Deep Insertion Destruction – Jasmine_Dlight & Peggy DeVille with XXL Toys, Gaping & Flying Dildo Finish

Deep Insertion Destruction – Jasmine_Dlight & Peggy DeVille with XXL Toys, Gaping & Flying Dildo Finish

Clips4sale 8 months ago

Khalifa Gold & Lissa Hamilton Private Show

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 5 months ago

Sissy daily anal training

Sissy daily anal training

XVideos 6 months ago

Tranny Cock Surprise (MP4)

68% HD 0:28 / 15:38

Tranny Cock Surprise (MP4)

Clips4sale 4 years ago

FULL MOVIE BNWO Bundle Compilation

67% 4K 0:27 / 1:00:48

FULL MOVIE BNWO Bundle Compilation

Clips4sale 1 year ago

DommeMommy B helps your through your Sissy Girl Transformation

DommeMommy B helps your through your Sissy Girl Transformation

Clips4sale 1 year ago

Stupid Whore Drinks Glass of Piss 1

Stupid Whore Drinks Glass of Piss 1

XVideos 1 year ago

Sissy Slut Fucked And Drained Stage 1 (WMV)

Sissy Slut Fucked And Drained Stage 1 (WMV)

Clips4sale 3 months ago

Kinky Kitchen Feminization

Kinky Kitchen Feminization

Clips4sale 6 months ago

Fill your Holes with Estrogen Cream

55% HD 0:19 / 7:01

Fill your Holes with Estrogen Cream

Clips4sale 8 months ago

Sissy training trance PMV

Sissy training trance PMV

XVideos 7 years ago

Beth Kinky - Sexy got domina trains her shemale horseman pt1 HD

Beth Kinky - Sexy got domina trains her shemale horseman pt1 HD

XVideos 5 years ago

Step-Mommy's Panty Boy - Bella Trixxx's Encouraged Crossdressing for Sissies AUDIO ONLY

Step-Mommy's Panty Boy - Bella Trixxx's Encouraged Crossdressing for Sissies AUDIO ONLY

Clips4sale 11 months ago

Blowjob and Cumkiss for Sissy Husband after 1 week of Chastity

65% 0:30 / 11:48

Blowjob and Cumkiss for Sissy Husband after 1 week of Chastity

Clips4sale 2 years ago

Raspberry Anal Training With Dildo After Huge Cumshot

Raspberry Anal Training With Dildo After Huge Cumshot

VivaTube 2 months ago

Alpha Male Femboy Sissy [M4M Audio Story]

Alpha Male Femboy Sissy [M4M Audio Story]

XVideos 1 year ago

Amber Burnt Private Show

Amber Burnt Private Show

Flirt4Free 2 years ago

Be my Girly Diaper Girl POV Full Movie

HD 0:30 / 1:04:39

Be my Girly Diaper Girl POV Full Movie

Clips4sale 2 years ago

Retribution Part 9

65% HD 0:31 / 14:29

Retribution Part 9

Clips4sale 1 year ago

Femboi Kara On A Pegging Rendezvous

Femboi Kara On A Pegging Rendezvous

TransTube.tv 1 year ago

Your Angel Cynthia Anal Training And Throat Fucking

Your Angel Cynthia Anal Training And Throat Fucking

ProPorn 2 years ago

Katalina Rosee Private Show

Katalina Rosee Private Show

Flirt4Free 8 months ago

Smallest castrated limp dick shemale compilation

Smallest castrated limp dick shemale compilation

XVideos 1 year ago

Powerful moment from "Mistress gonna transform you in a sissy fucktoy and make your ass sore (FEMINIZATION ROLEPLAY - AI"

Powerful moment from "Mistress gonna transform you in a sissy fucktoy and make your ass sore (FEMINIZATION ROLEPLAY - AI"

xHamster 11 months ago

Sophia Loreen Party on May 14, 2025 - Part 2

4K 2:00 / 39:50

Sophia Loreen Party on May 14, 2025 - Part 2

Flirt4Free 10 months ago

Misty's Blowbang Party

Misty's Blowbang Party

APClips 2 months ago

Cumdump Being Prepared for a Serious Facefuck by Smoking CD

56% HD 0:30 / 17:18

Cumdump Being Prepared for a Serious Facefuck by Smoking CD

Clips4sale 7 months ago

Transexual sintiendo orgasmo ass-fuck por primera vez

Transexual sintiendo orgasmo ass-fuck por primera vez

TrannyGem 1 year ago

Never A Real Girl Sissy - You'll always be a lesser copy of a woman - Sissy Training and Humiliation with Femdom Mistress Mystique - MP4

Never A Real Girl Sissy - You'll always be a lesser copy of a woman - Sissy Training and Humiliation with Femdom Mistress Mystique - MP4

Clips4sale 1 year ago

Brazilian sissy penetrates her muff rock hard with fake penis part two

Brazilian sissy penetrates her muff rock hard with fake penis part two

TrannyGem 2 years ago

Sissy Reprogrammed

Sissy Reprogrammed

Clips4sale 4 years ago

Dominant Woman, Chastity Cage, Beach and Sun

Dominant Woman, Chastity Cage, Beach and Sun

xHamster 9 months ago

NO MERCY DEEPTHROAT POV SHEMALE FETISHTRANSEXUAL HARDCORE ON SUB SLAVE COCKSUCKER

NO MERCY DEEPTHROAT POV SHEMALE FETISHTRANSEXUAL HARDCORE ON SUB SLAVE COCKSUCKER

Clips4sale 3 years ago

Quickly Face Fucked by Driver Passing by in My City Needed Hot Mouth Before Driving to Slovenia

Quickly Face Fucked by Driver Passing by in My City Needed Hot Mouth Before Driving to Slovenia

xHamster 1 year ago

Cheongsam transvestite treadmill training

Cheongsam transvestite treadmill training

Clips4sale 6 months ago

FISTING ANAL EM PUBLICO

FISTING ANAL EM PUBLICO

XVideos 6 months ago

Str8 Trainer

69% 0:29 / 22:54

Clips4sale 3 months ago

Lisa and Charlotte swallow double ended dildo together and meet in the middle

Lisa and Charlotte swallow double ended dildo together and meet in the middle

xHamster 3 years ago

Pussless-2024-supercut

Pussless-2024-supercut

XVideos 11 months ago

Wire on Sissy penetrating

Wire on Sissy penetrating

TransTube.tv 1 year ago

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