Training Videos - Trans (9,007)

Mistress Lady Renee - Prepping the whore for action - wmv

55% 0:16 / 11:33

Mistress Lady Renee - Prepping the whore for action - wmv

Clips4sale 1 year ago

8K - OCEX - Ancient Hermaphroditism Queen

4K 0:23 / 13:28

8K - OCEX - Ancient Hermaphroditism Queen

Clips4sale 1 year ago

Strap On Stories #8B: My Pegging Goddess Completes Her Sissy (Animated)

63% HD 0:25 / 16:18

Strap On Stories #8B: My Pegging Goddess Completes Her Sissy (Animated)

C4S 2 weeks ago

4K - Farthest Cumshot Ever!! ~Neon Girl Outfit~

60% 4K 0:11 / 39:30

4K - Farthest Cumshot Ever!! ~Neon Girl Outfit~

Clips4sale 2 years ago

DANCE IN YOUR PANTIES FOR ME SISSY

4K 0:29 / 13:05

DANCE IN YOUR PANTIES FOR ME SISSY

Clips4sale 1 year ago

Your New GAY Reality

37% 0:11 / 10:17

Your New GAY Reality

Clips4sale 3 years ago

Borgia's Sissy Tasks - Gender Bender Slut! (1080p)

Borgia's Sissy Tasks - Gender Bender Slut! (1080p)

Clips4sale 1 year ago

Rage vs Bea | 75kg vs 110kg |mp4|HD|

HD 0:55 / 17:48

Rage vs Bea | 75kg vs 110kg |mp4|HD|

Clips4sale 4 years ago

Giantess Sissy Anal Creampie

HD 0:25 / 10:54

Giantess Sissy Anal Creampie

Clips4sale 2 years ago

Sissy Dress Up Paige Steele Maleka

Sissy Dress Up Paige Steele Maleka

Clips4sale 2 years ago

In His Wicked Neighbor's Web Part 2

In His Wicked Neighbor's Web Part 2

Clips4sale 1 year ago

Submissive Training III

Submissive Training III

Clips4sale 1 year ago

Sissy Dress-Up Spitroast - Clara Dee POV Virtual Sex with Elle Eros

HD 0:28 / 13:34

Sissy Dress-Up Spitroast - Clara Dee POV Virtual Sex with Elle Eros

Clips4sale 1 year ago

Sissy Wife Panty Wearing CEI JOI

HD 0:10 / 14:35

Sissy Wife Panty Wearing CEI JOI

LoyalFans 3 months ago

FemDom Goddess with Strapon Encourages You to be Bisexual

FemDom Goddess with Strapon Encourages You to be Bisexual

Clips4sale 1 year ago

A Sissy Weekend Fantasy CUSTOM! Ft Miss Roper - 4K

4K 0:11 / 15:11

A Sissy Weekend Fantasy CUSTOM! Ft Miss Roper - 4K

Clips4sale 1 year ago

SISSY GETS DRESSED, PERMANENT CHASTITY, AND AN ANAL ORGASM 1080P - ELLIE IDOL

HD 0:29 / 12:22

SISSY GETS DRESSED, PERMANENT CHASTITY, AND AN ANAL ORGASM 1080P - ELLIE IDOL

Clips4sale 1 year ago

Sissy Trapped in my Basement

HD 0:30 / 11:29

Sissy Trapped in my Basement

Clips4sale 2 months ago

The Sissy's Great Challenge, dildo 8 Kilos, 30 Centimetres

HD 0:25 / 11:47

The Sissy's Great Challenge, dildo 8 Kilos, 30 Centimetres

Clips4sale 2 months ago

Inanna Justice Tests Gagged Sub as Human Chair and Leather Footstool - Trans Femme and Leather Part 7

Premium HD 11:58

Inanna Justice Tests Gagged Sub as Human Chair and Leather Footstool - Trans Femme and Leather Part 7

Clips4sale 4 months ago

Sissy Zone Cycle 3

63% 0:20 / 21:12

Sissy Zone Cycle 3

Clips4sale 1 year ago

Part 1: Caught Playing Dress-Up Sissy Tiffany's Vibrator Torment and Bondage

HD 0:25 / 11:55

Part 1: Caught Playing Dress-Up Sissy Tiffany's Vibrator Torment and Bondage

Clips4sale 3 weeks ago

Four Dommes Gangbang a Crossdresser and Newbie Slut (1080 EN-sub)

HD 0:52 / 21:01

Four Dommes Gangbang a Crossdresser and Newbie Slut (1080 EN-sub)

Clips4sale 2 years ago

Hard Spanking For Naughty TV Jessica (MP4)

65% 0:12 / 9:26

Hard Spanking For Naughty TV Jessica (MP4)

Clips4sale 1 year ago

You're My Sissy Wife Now - Clara Dee JOI

You're My Sissy Wife Now - Clara Dee JOI

Clips4sale 3 years ago

Naval Story 4 HD Special Offer

HD 0:11 / 21:49

Naval Story 4 HD Special Offer

Clips4sale 2 years ago

Drive-In Sissy Part 3 Written by Kylie Gable Narrated by Shayla Aspasia

HD 0:30 / 39:40

Drive-In Sissy Part 3 Written by Kylie Gable Narrated by Shayla Aspasia

Clips4sale 1 year ago

I milk my cute femboy while fingering his ass

Premium HD 12:03

I milk my cute femboy while fingering his ass

Clips4sale 2 weeks ago

BEST FRIENDS FOREVER

HD 0:15 / 15:51

BEST FRIENDS FOREVER

Clips4sale 4 years ago

All Dressed Up to Cum

All Dressed Up to Cum

Clips4sale 10 months ago

Work Fantasy

HD 0:26 / 18:01

Clips4sale 2 years ago

Intimate Anal with Sophie Ladder

63% HD 0:21 / 32:08

Intimate Anal with Sophie Ladder

Clips4sale 3 years ago

THE SISSY, THE BULL, THE LINGERIE, AND THE KEYHOLDER MESMERIZE - Sissy Chastity Training Mind Fuck

THE SISSY, THE BULL, THE LINGERIE, AND THE KEYHOLDER MESMERIZE - Sissy Chastity Training Mind Fuck

Clips4sale 1 year ago

Sissy Training Compilation

43% 0:20 / 25:12

Sissy Training Compilation

Clips4sale 4 years ago

Calisas Bondage Diaries: Do You Want This Job

66% 4K 0:22 / 18:03

Calisas Bondage Diaries: Do You Want This Job

Clips4sale 3 years ago

Sissy School Vlog Slumber Party

65% HD 0:30 / 10:38

Sissy School Vlog Slumber Party

Clips4sale 2 years ago

BOSSY DELILAH : TURNING THE TABLE ON HIM

65% HD 0:43 / 5:25

BOSSY DELILAH : TURNING THE TABLE ON HIM

Clips4sale 4 years ago

A THIEF'S PUNISHMENT

A THIEF'S PUNISHMENT

Clips4sale 5 months ago

Turn Yourself Into A Pretty Sissy - 854x480p mp4

Turn Yourself Into A Pretty Sissy - 854x480p mp4

Clips4sale 1 year ago

You Suck For Mistress Jasmin UHD

64% 4K 0:30 / 12:00

You Suck For Mistress Jasmin UHD

Clips4sale 1 year ago

I Want You In Lingerie

55% 4K 0:30 / 12:45

I Want You In Lingerie

Clips4sale 2 years ago

Making You My Sissy

Premium HD 11:34

Making You My Sissy

Clips4sale 2 years ago

completely submitted and feminized

completely submitted and feminized

Clips4sale 2 years ago

Sad Sissy Virgin Life

HD 0:10 / 10:18

Sad Sissy Virgin Life

LoyalFans 2 years ago

Lady Sara's Sissy Slut Training School: How to Please Men

66% HD 0:10 / 10:37

Lady Sara's Sissy Slut Training School: How to Please Men

LoyalFans 2 years ago

I love watching you Crossdress and then tying you up HD

65% HD 0:30 / 6:01

I love watching you Crossdress and then tying you up HD

Clips4sale 2 years ago

PISSING and DILDOING my SISSY lesbian girlfriend

PISSING and DILDOING my SISSY lesbian girlfriend

Clips4sale 2 years ago

Sissy For Alphas

60% HD 0:10 / 5:18

Sissy For Alphas

LoyalFans 2 years ago

Training before bigger toys

Training before bigger toys

Clips4sale 2 years ago

Stretching Steven’s Bussy

HD 0:24 / 14:15

Stretching Steven’s Bussy

Clips4sale 2 years ago

FEMINISING MY STRAIGHT BOYFRIEND RIMMING AND SUCKING FUCKING IN MAKEUP DRESSED UP P2

HD 0:20 / 10:04

FEMINISING MY STRAIGHT BOYFRIEND RIMMING AND SUCKING FUCKING IN MAKEUP DRESSED UP P2

Clips4sale 2 years ago

The Sissification of Brenda 5 Part Collection Written by Sissy Brenda Narrated by Shayla Aspasia

Premium HD 3:14:26

The Sissification of Brenda 5 Part Collection Written by Sissy Brenda Narrated by Shayla Aspasia

Clips4sale 2 years ago

SISSY MILKING

Clips4sale 1 year ago

tiny fly brain GOONER teardown

60% HD 0:26 / 12:03

tiny fly brain GOONER teardown

Clips4sale 1 year ago

Cock Probe 2

HD 0:10 / 10:03

LoyalFans 2 years ago

Her Prisoner Part 24 - Sissy Training VII

61% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 2 years ago

MERCILESS DEEPTHOAT NON STOP BLOWJOB DRESSING SERVICES SUB SISSY WHORE SLUT P2

62% HD 0:21 / 10:09

MERCILESS DEEPTHOAT NON STOP BLOWJOB DRESSING SERVICES SUB SISSY WHORE SLUT P2

Clips4sale 2 years ago

Mrs Nara Sissification Training - Chapter Two: Swallow like a Bitch (1080 EN-sub)

HD 0:30 / 15:33

Mrs Nara Sissification Training - Chapter Two: Swallow like a Bitch (1080 EN-sub)

Clips4sale 2 years ago

MK’s Sissy Training Academy for Sissy Rejects

HD 0:10 / 17:38

MK’s Sissy Training Academy for Sissy Rejects

LoyalFans 2 years ago

Convincing You To Become A Controlled Sissy-Girl (HD MP4)

62% 4K 0:31 / 14:50

Convincing You To Become A Controlled Sissy-Girl (HD MP4)

Clips4sale 2 years ago

GIMP TRAINING: Mitten Nipples with Kamma LaVey

GIMP TRAINING: Mitten Nipples with Kamma LaVey

Clips4sale 2 years ago

Giada da Vinci offers LunaFeetCute her only monthly chance to have an orgasm with chastity belt, crossdressing, cock tease, tease&denial, anal masturbation

HD 0:29 / 13:48

Giada da Vinci offers LunaFeetCute her only monthly chance to have an orgasm with chastity belt, crossdressing, cock tease, tease&denial, anal masturbation

Clips4sale 2 years ago

Making my Boyfriend a Sissy

HD 0:31 / 11:02

Making my Boyfriend a Sissy

Clips4sale 2 years ago

Bubble Butt Sissy Boy Loves to Fuck His Asshole on Cam Pt 2 HD

HD 0:31 / 10:02

Bubble Butt Sissy Boy Loves to Fuck His Asshole on Cam Pt 2 HD

Clips4sale 2 years ago

602 Swallow my Futa cock, be mouth fucked by a dominant Blonde Mistress in black shiny boots, a latex skirt, a leather top, wrist watch and 8 inches strap-on, cum countdown

HD 0:30 / 10:11

602 Swallow my Futa cock, be mouth fucked by a dominant Blonde Mistress in black shiny boots, a latex skirt, a leather top, wrist watch and 8 inches strap-on, cum countdown

Clips4sale 2 years ago

Hunted and Caged Part 10 - Prisoner to sissy Transformation 4 with Anna List

4K 0:47 / 10:18

Hunted and Caged Part 10 - Prisoner to sissy Transformation 4 with Anna List

Clips4sale 2 years ago

Sissy Feminization and Pegging POV Armpit Worship

Sissy Feminization and Pegging POV Armpit Worship

Clips4sale 2 years ago

Bitch For Futa BBC and Ass | MahoganQen

Premium HD 10:59

Bitch For Futa BBC and Ass | MahoganQen

Clips4sale 2 years ago

SISSY TRANSFORMATION

HD 0:10 / 10:04

SISSY TRANSFORMATION

LoyalFans 2 years ago

Aria & Jaymee - Cum for our Tbrats Soles

Aria & Jaymee - Cum for our Tbrats Soles

Clips4sale 2 years ago

OLIVE GREEN LATEX CATSUIT SHINE UP FULL BODY SPRAY MASSAGE ONLY

HD 0:22 / 10:28

OLIVE GREEN LATEX CATSUIT SHINE UP FULL BODY SPRAY MASSAGE ONLY

Clips4sale 2 years ago

Ryley Rails First Adult Video 2017

Ryley Rails First Adult Video 2017

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

WEDNESDAY MEETING BAREBACK CREAMPIE FOR THE FIRST TIME WITH CUMSHOT FETISHTRANSEXUAL

4K 0:21 / 10:36

WEDNESDAY MEETING BAREBACK CREAMPIE FOR THE FIRST TIME WITH CUMSHOT FETISHTRANSEXUAL

Clips4sale 2 years ago

Tranny Foot Slave And Milking Stage 3 (WMV)

Tranny Foot Slave And Milking Stage 3 (WMV)

Clips4sale 1 year ago

Blowjob Before to Get Fuked

65% 0:12 / 9:43

Blowjob Before to Get Fuked

Clips4sale 1 year ago

FEMDOM HOTWIFE TRANSFORMED YOU INTO A CUCKOLD SLAVE - Cuckold Slave Fantasy Training BETA Mesmerize

FEMDOM HOTWIFE TRANSFORMED YOU INTO A CUCKOLD SLAVE - Cuckold Slave Fantasy Training BETA Mesmerize

Clips4sale 1 year ago

Mistress DJ's Halloween Stories of Feminization and Domination

Mistress DJ's Halloween Stories of Feminization and Domination

Clips4sale 1 year ago

LIFESTYLE DOMME MADE YOU CROSSDRESS - Crossdressing Training Beta Mind Fuck

LIFESTYLE DOMME MADE YOU CROSSDRESS - Crossdressing Training Beta Mind Fuck

Clips4sale 1 year ago

SHE IS A BETTER FOOTSLAVE THAN HIM Part 1 & 2

63% 0:09 / 23:41

SHE IS A BETTER FOOTSLAVE THAN HIM Part 1 & 2

Clips4sale 1 year ago

Two doms encourage you to explore your bisexual side by sucking cock - Jaq Quicksilver and Sydney Screams - FtM Jaq and BBW Sydney coach you through your first blowjob while you jerk off - joi, bi, handjob, threesome, dirty talk - 720p mp4

65% HD 0:29 / 11:27

Two doms encourage you to explore your bisexual side by sucking cock - Jaq Quicksilver and Sydney Screams - FtM Jaq and BBW Sydney coach you through your first blowjob while you jerk off - joi, bi, handjob, threesome, dirty talk - 720p mp4

Clips4sale 1 year ago

KEEP YOUR SECRETS CLOSE & YOUR PANTIES CLOSER

KEEP YOUR SECRETS CLOSE & YOUR PANTIES CLOSER

LoyalFans 1 year ago

MISTRESS HOTWIFE TURNS YOU INTO A LIVE IN SISSYMAID MIND FUCK - The Happy Maid, Sissymaid Training

MISTRESS HOTWIFE TURNS YOU INTO A LIVE IN SISSYMAID MIND FUCK - The Happy Maid, Sissymaid Training

Clips4sale 1 year ago

Disciplining the Disobedient Sissy With Pegging - Mistress Julia

Disciplining the Disobedient Sissy With Pegging - Mistress Julia

Clips4sale 1 year ago

Beyond Male: The Ultimate Sissy Transformation by Mistress Julia

Beyond Male: The Ultimate Sissy Transformation by Mistress Julia

Clips4sale 1 year ago

Pegging KC with Red Toy

Pegging KC with Red Toy

Clips4sale 1 year ago

Being a Girl Is More Fun

65% 4K 0:17 / 10:29

Being a Girl Is More Fun

Clips4sale 1 year ago

Two Dommes And The Delivery Boy: Buy 2 clips, Get 1 clip for free!

Two Dommes And The Delivery Boy: Buy 2 clips, Get 1 clip for free!

Clips4sale 1 year ago

Slutty SISSY CLOWN Twin (mov)

Slutty SISSY CLOWN Twin (mov)

Clips4sale 4 years ago

TS Sissy Jenny follows the instructions of a video of her Master_Part_1

TS Sissy Jenny follows the instructions of a video of her Master_Part_1

Clips4sale 4 years ago

Pack For Your Pantyhose Trip (1080 HD)

Pack For Your Pantyhose Trip (1080 HD)

Clips4sale 3 years ago

Goddess Knows your Secrets (MOV)

Goddess Knows your Secrets (MOV)

Clips4sale 3 years ago

Training of the sissy bitch Emily by Mistress Antonella

Training of the sissy bitch Emily by Mistress Antonella

Clips4sale 3 years ago

Better As a Sissy (1080)

55% HD 0:18 / 8:48

Better As a Sissy (1080)

Clips4sale 3 years ago

Protect The Virgin Sissy Part 3 StrapOn Spitroast

Protect The Virgin Sissy Part 3 StrapOn Spitroast

Clips4sale 3 years ago

Sissy boy train your sloppy ass fisting

Sissy boy train your sloppy ass fisting

Clips4sale 3 years ago

STUCK IN THE RESTRAINT CHAIR

STUCK IN THE RESTRAINT CHAIR

Clips4sale 3 years ago

4K - Bunny Girl - Original Character

4K 0:18 / 15:30

4K - Bunny Girl - Original Character

Clips4sale 3 years ago

Neighborhood Sissy

Neighborhood Sissy

Clips4sale 3 years ago

Anastasia Rose Fondled, Spanked, Wedgied, Made To Orgasm (HD1080 WMV)

Anastasia Rose Fondled, Spanked, Wedgied, Made To Orgasm (HD1080 WMV)

Clips4sale 4 years ago

4K - Lusty Shower Vol4

4K 0:19 / 18:29

4K - Lusty Shower Vol4

Clips4sale 4 years ago

Sissyfied

Clips4sale 3 years ago

SISSYBB EXPOSED

SISSYBB EXPOSED

Clips4sale 3 years ago

Mean Girl Sissifies and Humiliates You Part 3

Mean Girl Sissifies and Humiliates You Part 3

Clips4sale 3 years ago

BAD SISSY BOY (wmv) PART 2

BAD SISSY BOY (wmv) PART 2

Clips4sale 3 years ago

Sissy Ashley A Chairtied and Trained in Her Pink Panties

Sissy Ashley A Chairtied and Trained in Her Pink Panties

Clips4sale 3 years ago

Slave To Futanari

HD 0:22 / 19:40

Slave To Futanari

Clips4sale 3 years ago

Fishnets for faggots

Fishnets for faggots

Clips4sale 3 years ago

A Sissy Spit Roast

66% HD 0:28 / 8:28

A Sissy Spit Roast

Clips4sale 3 years ago

Sissy Bimbofication

Sissy Bimbofication

Clips4sale 3 years ago

Pegging Your Ass like a Fleshlight - Gwen Adora BBW Femdom POV Strap On - hd mp4

HD 0:29 / 10:37

Pegging Your Ass like a Fleshlight - Gwen Adora BBW Femdom POV Strap On - hd mp4

Clips4sale 3 years ago

Birthday Bi Party - Part Five (Full Video) - HD

66% HD 0:19 / 9:02

Birthday Bi Party - Part Five (Full Video) - HD

Clips4sale 3 years ago

Big Cocked Tinder Date: Anal Fuck POV - Gwen Adora BBW Futanari Anal Training - sd mp4

HD 0:30 / 12:23

Big Cocked Tinder Date: Anal Fuck POV - Gwen Adora BBW Futanari Anal Training - sd mp4

Clips4sale 3 years ago

CUSTOM Pre-cum Sissy Slut Humiliation 2 (wmv)

CUSTOM Pre-cum Sissy Slut Humiliation 2 (wmv)

Clips4sale 3 years ago

Bar Bottom

Clips4sale 3 years ago

Caning training with Syren - Sadistic Lucy - MP4 SD

Caning training with Syren - Sadistic Lucy - MP4 SD

Clips4sale 3 years ago

Is This Sissy Sorry Extended Version Lola Minaj Trans Masturbation Dominatrix WMVSD Final

HD 0:52 / 18:31

Is This Sissy Sorry Extended Version Lola Minaj Trans Masturbation Dominatrix WMVSD Final

Clips4sale 3 years ago

Birthday Bi Party - Part Four - Full - WMV (HD)

65% HD 0:19 / 10:01

Birthday Bi Party - Part Four - Full - WMV (HD)

Clips4sale 3 years ago

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

65% HD 0:11 / 36:30

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

Clips4sale 4 years ago

Sissy craves cock

Sissy craves cock

Clips4sale 4 years ago

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9,007 results found

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