Training Videos (52,902)

GLORY HOLE WHORE 2 *HD 1080*

73% HD 0:35 / 12:45

GLORY HOLE WHORE 2 *HD 1080*

Clips4sale 2 years ago

PERMANENT FEMINIZATION - Femdom Goddess Worship Castration Penectomy Dirty Talk by Miss Faith Rae with Submissive Encouragement and Surgical Talk - MKV

PERMANENT FEMINIZATION - Femdom Goddess Worship Castration Penectomy Dirty Talk by Miss Faith Rae with Submissive Encouragement and Surgical Talk - MKV

Clips4sale 3 weeks ago

Red Corselette Bathroom Fun (4k)

4K 0:30 / 14:52

Red Corselette Bathroom Fun (4k)

Clips4sale 2 weeks ago

A Bound Prostate Milking for the Sissy Slave

58% 0:20 / 17:51

A Bound Prostate Milking for the Sissy Slave

Clips4sale 1 year ago

Horny Striptease Harley

Horny Striptease Harley

Flirt4Free 6 months ago

Pretty In Pink (720p)

74% HD 0:30 / 7:43

Pretty In Pink (720p)

Clips4sale 3 months ago

Pissy Sissy

HD 0:25 / 18:02

Clips4sale 3 weeks ago

Panty Hose Sissy Training

60% 4K 0:30 / 12:14

Panty Hose Sissy Training

Clips4sale 2 months ago

small dick humiliation

65% 4K 0:28 / 12:37

small dick humiliation

Clips4sale 4 years ago

ALPHA ADARA *HD 720*

59% HD 0:30 / 14:16

ALPHA ADARA *HD 720*

Clips4sale 1 year ago

Futa's Cock Sucker

Futa's Cock Sucker

Clips4sale 1 month ago

Real Femdom Milking; FLR Ruined Orgasm Handjob cumshot BBW MiLF Domme with Feminized Submissive POV featuring OctoGoddess and quiver real BDSM couple wmv Version

62% 0:14 / 14:18

Real Femdom Milking; FLR Ruined Orgasm Handjob cumshot BBW MiLF Domme with Feminized Submissive POV featuring OctoGoddess and quiver real BDSM couple wmv Version

Clips4sale 1 year ago

SHEMALES MADE YOU IMPOTENT FOR PUSSY

HD 0:23 / 14:01

SHEMALES MADE YOU IMPOTENT FOR PUSSY

Clips4sale 3 days ago

4K - PHANTOM CUM BURST of Wasteland Girl (Special Editing Video)

64% 4K 0:08 / 38:20

4K - PHANTOM CUM BURST of Wasteland Girl (Special Editing Video)

Clips4sale 1 year ago

Butt Drops On Sissy - Dakota Charms HDMP4

63% HD 0:15 / 3:30

Butt Drops On Sissy - Dakota Charms HDMP4

Clips4sale 3 years ago

Liam Jacobson Private Show

52% HD 2:00 / 4:59

Liam Jacobson Private Show

Flirt4Free 4 years ago

Sissy Anal Needs

67% HD 0:39 / 11:39

Sissy Anal Needs

FapHouse 7 months ago

Exquisite submissive draped in a sleek leopard-print catsuit, finished with glossy designer boots, the best of Deepthroat rimming

60% HD 0:21 / 10:10

Exquisite submissive draped in a sleek leopard-print catsuit, finished with glossy designer boots, the best of Deepthroat rimming

Clips4sale 4 months ago

Your Body Is My Toy: BDSM Bondage Blowjob Cumshot w Fisting

57% 4K 0:28 / 32:29

Your Body Is My Toy: BDSM Bondage Blowjob Cumshot w Fisting

Clips4sale 2 months ago

LATEX CLAD DOMINA AVA SAVAGE GAPES HER TRANS SLUT

52% 0:11 / 7:15

LATEX CLAD DOMINA AVA SAVAGE GAPES HER TRANS SLUT

Clips4sale 1 year ago

BLUE MONDAY: THE VOLUNTARY – PART 2: THE MULTIGAG

61% 0:12 / 14:04

BLUE MONDAY: THE VOLUNTARY – PART 2: THE MULTIGAG

Clips4sale 10 months ago

WEAR THIS FOR ME SISSY

56% 0:21 / 8:42

WEAR THIS FOR ME SISSY

Clips4sale 1 year ago

Giving up All Resistance

58% 0:39 / 24:56

Giving up All Resistance

FapHouse 2 months ago

Fat Ass CD Sissy blows and gets fucked by a Monster BBC Fiona Fortune

54% 0:30 / 16:43

Fat Ass CD Sissy blows and gets fucked by a Monster BBC Fiona Fortune

Clips4sale 4 months ago

Faggot Instinct Awakening | MahoganyQen

66% 0:23 / 10:25

Faggot Instinct Awakening | MahoganyQen

Clips4sale 2 years ago

Feminized Sissy Gets STRAPPED

Feminized Sissy Gets STRAPPED

Clips4sale 1 year ago

Private Sex-tape

72% HD 0:39 / 11:41

Private Sex-tape

FapHouse 1 year ago

Hard anal destruction and deepthroat training for stupid maso sexslave

Premium HD 26:51

Hard anal destruction and deepthroat training for stupid maso sexslave

xnxxGold 5 months ago

P3 SLOW MOTION LIVING DOLL FUCKING NON STOP IN PVC LATEX RESTRAINED

64% HD 0:20 / 10:25

P3 SLOW MOTION LIVING DOLL FUCKING NON STOP IN PVC LATEX RESTRAINED

Clips4sale 1 year ago

You are a Prisoner to your Sissy Porn

HD 0:29 / 11:43

You are a Prisoner to your Sissy Porn

Clips4sale 2 months ago

P4 HALLOWEEN BLACK AND ORANGE CATSUIT TWINK LATEX FEMMEBOI TEASING KISSING DEEPTHROAT TAKING CONDOM OFF SHEMALE

HD 0:20 / 10:12

P4 HALLOWEEN BLACK AND ORANGE CATSUIT TWINK LATEX FEMMEBOI TEASING KISSING DEEPTHROAT TAKING CONDOM OFF SHEMALE

Clips4sale 10 months ago

Cute Dance with Naughty Girl

Cute Dance with Naughty Girl

Flirt4Free 6 months ago

Pink Stockings Bimbo Sissy Training

Premium HD 10:00

Pink Stockings Bimbo Sissy Training

XVideosRed 1 year ago

I Beg You, Massage My Tits with Oil

I Beg You, Massage My Tits with Oil

Flirt4Free 7 months ago

Sophia Loreen Private Show

59% 4K 2:00 / 8:41

Sophia Loreen Private Show

Flirt4Free 3 months ago

No More Masculinity

55% 0:18 / 11:11

No More Masculinity

Clips4sale 11 months ago

4K - Girl Cock Yoga Pose 2

63% 4K 0:21 / 26:16

4K - Girl Cock Yoga Pose 2

Clips4sale 1 year ago

BEST LITTLE DUNGEON IN SOUTH FLORIDA *HD 1080*

HD 0:33 / 32:36

BEST LITTLE DUNGEON IN SOUTH FLORIDA *HD 1080*

Clips4sale 1 year ago

Hana Rouse Private Show

70% HD 2:00 / 4:23

Hana Rouse Private Show

Flirt4Free 1 year ago

Luke Hardy & Cristian Ford Private Show

54% HD 2:00 / 18:14

Luke Hardy & Cristian Ford Private Show

Flirt4Free 10 months ago

sexy oiled big dick tgirl cums from bad dragon tentacle anal

64% 4K 0:15 / 8:45

sexy oiled big dick tgirl cums from bad dragon tentacle anal

Clips4sale 3 months ago

Anna Finally Succeeds in Deep Throating After Intense Training

61% HD 0:39 / 1:01:07

Anna Finally Succeeds in Deep Throating After Intense Training

FapHouse 3 months ago

caged sissy whore fucked senseless by BBC sex machine cums

63% 0:21 / 14:27

caged sissy whore fucked senseless by BBC sex machine cums

Clips4sale 10 months ago

Bought & Broken In (1080 HD)

68% 4K 0:53 / 20:39

Bought & Broken In (1080 HD)

Clips4sale 3 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Cock And Cum Slut For Mel Fire (MP4)

Cock And Cum Slut For Mel Fire (MP4)

Clips4sale 1 month ago

Introduction to Crossdressing

60% 0:20 / 13:00

Introduction to Crossdressing

Clips4sale 2 years ago

Remote Controlled Sissy Dolls (MP4)

63% 0:13 / 24:45

Remote Controlled Sissy Dolls (MP4)

Clips4sale 2 years ago

Sissy Spitroasted and filled with cum by BBC & Muscle Mommy

65% 0:34 / 24:39

Sissy Spitroasted and filled with cum by BBC & Muscle Mommy

Clips4sale 5 months ago

Mtof Femboy to Bimbo Transformation and Training to Be Bimbo Cumslut

57% HD 0:39 / 7:00

Mtof Femboy to Bimbo Transformation and Training to Be Bimbo Cumslut

FapHouse 8 months ago

MILF1852 - Hardcore FemDom: Billionaire to Bitch

HD 0:30 / 43:38

MILF1852 - Hardcore FemDom: Billionaire to Bitch

Clips4sale 11 months ago

RUBBERSLUT HIGH HEELS TRAINING FULL SESSION- Hard Bondage & Humiliation for my LatexToy 1080p

4K 0:48 / 31:39

RUBBERSLUT HIGH HEELS TRAINING FULL SESSION- Hard Bondage & Humiliation for my LatexToy 1080p

Clips4sale 6 days ago

8K UNMASKED - KPop Femboy Cum Swallowing Session

64% 4K 0:24 / 37:10

8K UNMASKED - KPop Femboy Cum Swallowing Session

Clips4sale 1 month ago

Sissy Stretching for Stuffing in Pantyhose

58% 0:30 / 14:10

Sissy Stretching for Stuffing in Pantyhose

Clips4sale 3 years ago

Totally Emasculated

4K 0:26 / 14:04

Totally Emasculated

Clips4sale 1 month ago

STROKE FAGGOT

46% 4K 0:25 / 12:07

Clips4sale 2 years ago

Destroyed Entertainment

62% HD 0:15 / 8:10

Destroyed Entertainment

Clips4sale 1 year ago

transforming you into a bimbo sissy slut

51% 0:11 / 20:09

transforming you into a bimbo sissy slut

Clips4sale 3 years ago

Femboy Craves CBT Punishment

70% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 3 years ago

Nylon Sissy Slave - Candle Boxxx HDMP4

43% 0:14 / 13:03

Nylon Sissy Slave - Candle Boxxx HDMP4

Clips4sale 1 year ago

SISSY DOLLY TORMENT

57% 4K 0:30 / 7:24

SISSY DOLLY TORMENT

Clips4sale 11 months ago

Muscular Sasha with Huge Cock! Muscle and Futa Fetish

52% 0:57 / 10:04

Muscular Sasha with Huge Cock! Muscle and Futa Fetish

Clips4sale 2 years ago

Live in sissy bedtime - Teased and caged

Live in sissy bedtime - Teased and caged

Clips4sale 1 year ago

Sissy Oral Fun Pt1

64% HD 0:27 / 10:09

Sissy Oral Fun Pt1

Clips4sale 11 months ago

PetGirl Helps Initiate Scared Newbie

47% HD 0:10 / 12:29

PetGirl Helps Initiate Scared Newbie

Clips4sale 2 years ago

The Sissy slut getting fisted and double too - Part 1

The Sissy slut getting fisted and double too - Part 1

Clips4sale 1 year ago

Fuck My Giantess Cock!

63% HD 0:56 / 16:03

Fuck My Giantess Cock!

Clips4sale 1 year ago

Female Masked Sissy Doll Makeup Routine and Sexy Chat

61% 4K 0:28 / 21:41

Female Masked Sissy Doll Makeup Routine and Sexy Chat

Clips4sale 1 year ago

Goth Club Wannabe Used by T-Girl Gang: Strap-on Bi Training Fantasy [CUSTOM] featuring Serena Lust

HD 0:58 / 23:24

Goth Club Wannabe Used by T-Girl Gang: Strap-on Bi Training Fantasy [CUSTOM] featuring Serena Lust

Clips4sale 3 weeks ago

Dressing Like A Girl - Candle Boxxx

46% 0:15 / 22:26

Dressing Like A Girl - Candle Boxxx

C4S 2 years ago

Orianna Dunn Private Show

50% HD 2:00 / 6:57

Orianna Dunn Private Show

Flirt4Free 1 year ago

Sissification School 2

Sissification School 2

Clips4sale 1 year ago

Sissy Body Switch

50% 0:26 / 14:54

Sissy Body Switch

Clips4sale 2 years ago

Ryan Markins & Rowan Markins Private Show

47% HD 2:00 / 4:22

Ryan Markins & Rowan Markins Private Show

Flirt4Free 2 years ago

PANTYHOSE BONDAGE & FOOTJOB WITH PAULA

61% 0:17 / 19:24

PANTYHOSE BONDAGE & FOOTJOB WITH PAULA

Clips4sale 1 month ago

WICKED RECOURSE *HD 1080*

68% HD 0:36 / 14:07

WICKED RECOURSE *HD 1080*

Clips4sale 1 year ago

Sissy Roommate Girly JOI

42% 0:14 / 10:33

Sissy Roommate Girly JOI

Clips4sale 11 months ago

Sissy whore training - Encouraged Bi and CEI

63% 0:30 / 11:32

Sissy whore training - Encouraged Bi and CEI

Clips4sale 9 months ago

ADVANCED CROSSDRESSING BETA - Crossdressing Training [Crossdresser] [Crossdress] [Transgender] [How To Crossdress] [Female Clothes] [Dressing Up] [Femme] [Fem Woman]

46% 0:30 / 44:24

ADVANCED CROSSDRESSING BETA - Crossdressing Training [Crossdresser] [Crossdress] [Transgender] [How To Crossdress] [Female Clothes] [Dressing Up] [Femme] [Fem Woman]

C4S 11 months ago

Femdom Pool Party Fuck Fest - Mistress Kendra, Mistress Susi, Ts Slayer, pegging, orgy, ts girls

63% HD 0:51 / 26:15

Femdom Pool Party Fuck Fest - Mistress Kendra, Mistress Susi, Ts Slayer, pegging, orgy, ts girls

Clips4sale 2 years ago

Futanari is much much better - ASMR, ANIME, AUDIO, LOOP, JOI

59% 0:16 / 10:28

Futanari is much much better - ASMR, ANIME, AUDIO, LOOP, JOI

Clips4sale 1 year ago

fuck face no mercy

67% HD 2:00 / 19:52

fuck face no mercy

Flirt4Free 1 year ago

Her Prisoner Part 24 - Sissy Training VII

64% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 1 year ago

AMATEUR RIMMING DEEPTHROAT LEATHER TOP SUBMISSIVE DATING WITH CUMSHOT CIM P2

59% 4K 0:21 / 10:20

AMATEUR RIMMING DEEPTHROAT LEATHER TOP SUBMISSIVE DATING WITH CUMSHOT CIM P2

Clips4sale 2 years ago

Sophia Loreen Party on May 8, 2024

45% HD 2:00 / 52:00

Sophia Loreen Party on May 8, 2024

Flirt4Free 1 year ago

Meiko crossdresses you to be her new girlfriend_

Meiko crossdresses you to be her new girlfriend_

Clips4sale 2 years ago

Ava Venom Double FemDom Spit Roasted to Cumshot

53% 0:30 / 23:55

Ava Venom Double FemDom Spit Roasted to Cumshot

C4S 5 months ago

Sissification of Rosie - Pt1

63% HD 0:53 / 13:38

Sissification of Rosie - Pt1

Clips4sale 1 year ago

SISSYMAID DRESSUP TRANSFORMATION - Sissymaid Command Mesmerize [Sissy] [Sissy Training] [Sissymaids] [Maids] [French Maid] [Sissymaid Dress] [Outfits] [Sissy Outfits] [Dressing Up] [Sissified] [Sissymaid Transformation] New

58% 0:30 / 25:05

SISSYMAID DRESSUP TRANSFORMATION - Sissymaid Command Mesmerize [Sissy] [Sissy Training] [Sissymaids] [Maids] [French Maid] [Sissymaid Dress] [Outfits] [Sissy Outfits] [Dressing Up] [Sissified] [Sissymaid Transformation] New

C4S 11 months ago

TOO MUCH TS TEMPTATION PT 1 *HD 1080*

43% HD 0:11 / 11:44

TOO MUCH TS TEMPTATION PT 1 *HD 1080*

Clips4sale 1 year ago

A Sissy for the Cheer Team

65% HD 0:29 / 11:00

A Sissy for the Cheer Team

Clips4sale 4 months ago

Sissy Maids Cant Be Lazy

56% 0:39 / 29:53

Sissy Maids Cant Be Lazy

FapHouse 2 months ago

Cycling in over 30 degrees! Tranny girl rubs her asshole on the bike!

71% HD 0:25 / 10:26

Cycling in over 30 degrees! Tranny girl rubs her asshole on the bike!

Clips4sale 11 months ago

Bimbo FuckDoll Pegged

49% 0:25 / 11:04

Bimbo FuckDoll Pegged

Clips4sale 9 months ago

(523) Sissygasm: Crossdresser with Anal Plug and Wand Vibrator - Zoulette (1080p, MP4)

57% HD 0:20 / 11:09

(523) Sissygasm: Crossdresser with Anal Plug and Wand Vibrator - Zoulette (1080p, MP4)

Clips4sale 7 months ago

Sissy Wife Eats Her Cum Out Of Her Panties - Clara Dee JOI

64% 0:27 / 14:34

Sissy Wife Eats Her Cum Out Of Her Panties - Clara Dee JOI

Clips4sale 2 years ago

Trans Mistress Plans Your Sissy Gangbang

66% 0:30 / 10:44

Trans Mistress Plans Your Sissy Gangbang

Clips4sale 3 months ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined by Intruder

58% HD 0:10 / 31:04

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined by Intruder

LoyalFans 1 week ago

Blonde Trans Bimbo TS Natasha Magenta Blowjob and Facial

57% HD 0:27 / 9:25

Blonde Trans Bimbo TS Natasha Magenta Blowjob and Facial

Clips4sale 1 year ago

Fucking Cock Pump

HD 2:00 / 43:01

Fucking Cock Pump

Flirt4Free 3 years ago

Big Fat Dick

63% 0:11 / 19:10

Clips4sale 2 years ago

feminization - post surgery virginity taking

54% HD 0:11 / 5:55

feminization - post surgery virginity taking

Clips4sale 2 years ago

Sissy Slut Test *wmv*

61% 0:20 / 9:39

Sissy Slut Test *wmv*

Clips4sale 2 months ago

Ass To Mouth Sissy Training (MP4)

Ass To Mouth Sissy Training (MP4)

Clips4sale 1 year ago

Accomplishments in your Mistress's name [1080p, mp4]

68% HD 0:14 / 10:03

Accomplishments in your Mistress's name [1080p, mp4]

Clips4sale 2 years ago

Chastity & Anal Training My Collared Slave Girl - Bondage, Denial & Strict Control! with River Enza - 4K MP4

4K 0:28 / 16:02

Chastity & Anal Training My Collared Slave Girl - Bondage, Denial & Strict Control! with River Enza - 4K MP4

Clips4sale 1 month ago

brace face trans teen sucks cock and deep throat while caged

65% 0:15 / 12:54

brace face trans teen sucks cock and deep throat while caged

Clips4sale 7 months ago

THAI SLAVE LADYBOY ANAL CASTING

THAI SLAVE LADYBOY ANAL CASTING

C4S 8 months ago

Be My Sissy Slave

65% HD 0:23 / 11:27

Be My Sissy Slave

Clips4sale 2 years ago

POV: Sissy Bussy Training mp4

57% 0:08 / 7:21

POV: Sissy Bussy Training mp4

Clips4sale 2 months ago

Captured feminized latexed & enslaved

40% HD 0:30 / 8:57

Captured feminized latexed & enslaved

Clips4sale 9 months ago

ADMIT YOUR TRANS-GRESSIONS

46% 4K 0:21 / 6:29

ADMIT YOUR TRANS-GRESSIONS

Clips4sale 9 months ago

Chastity & Anal Training My Collared Slave Girl - Bondage, Denial & Strict Control! with River Enza - 720p MP4

4K 0:28 / 16:02

Chastity & Anal Training My Collared Slave Girl - Bondage, Denial & Strict Control! with River Enza - 720p MP4

Clips4sale 1 month ago

High Heels Love Tongue Worship (1080p)

56% HD 0:30 / 7:06

High Heels Love Tongue Worship (1080p)

Clips4sale 4 months ago

Sissy for Whitney_wmv__

47% 0:23 / 8:23

Sissy for Whitney_wmv__

Clips4sale 10 months ago

Sissy Faggot's Weekend 1080p mp4

43% HD 0:30 / 7:29

Sissy Faggot's Weekend 1080p mp4

Clips4sale 1 year ago

My Collared and Kept Pet - 1080p

HD 0:17 / 12:19

My Collared and Kept Pet - 1080p

Clips4sale 2 years ago

Amazing bimbo Barbie on ass cumshoted

Premium HD 33:00

Amazing bimbo Barbie on ass cumshoted

Clips4sale 1 year ago

Leather spitting smoking sissification POV_wmv_

57% 0:21 / 11:19

Leather spitting smoking sissification POV_wmv_

Clips4sale 2 years ago

SUBMISSIVE LADYBOY ANAL CASTING & SLAVE TRAINING

69% HD 0:48 / 30:36

SUBMISSIVE LADYBOY ANAL CASTING & SLAVE TRAINING

Clips4sale 3 months ago

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