Search results - Sissy Training

Total found: 393 videos (page 3)

Tough scout training is a part of the bear's foreplay9:59
6 months ago AnyGay

Tough scout training is a part of the bear's foreplay

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Daddy Loves His Little Fag - Slave Training3:05
2 years ago xHamster

Daddy Loves His Little Fag - Slave Training

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Anal training with large dildo5:48
2 years ago xHamster

Anal training with large dildo

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Jessie Colter fulfills his anal needs during sparing training4:05
6 months ago AnyGay

Jessie Colter fulfills his anal needs during sparing training

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Muscular mature fighters skip their training for a little ass fuck3:59
7 months ago AnyGay

Muscular mature fighters skip their training for a little ass fuck

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Hairbrush self spanking in micro chastity cage training PART 15:30
2 years ago xHamster

Hairbrush self spanking in micro chastity cage training PART 1

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Self spanking in micro chastity cage training Part 22:28
2 years ago xHamster

Self spanking in micro chastity cage training Part 2

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Anal Depth Training with Slinks12:20
2 years ago xHamster

Anal Depth Training with Slinks

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Hardcore Slave Training JOI - Extreme Humiliation and Dirty Talk3:19
2 years ago xHamster

Hardcore Slave Training JOI - Extreme Humiliation and Dirty Talk

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Dominant Hunk Verbal Humiliation after GYM - Slave Training3:02
2 years ago xHamster

Dominant Hunk Verbal Humiliation after GYM - Slave Training

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Alpha Hunk Spits and Pisses on your face - Slave Training2:34
2 years ago xHamster

Alpha Hunk Spits and Pisses on your face - Slave Training

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GIFT FOR A FAGGOT SLAVE - Hardcore Obedience Training3:43
2 years ago xHamster

GIFT FOR A FAGGOT SLAVE - Hardcore Obedience Training

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Anal Training with Large Dildo1:34
2 years ago xHamster

Anal Training with Large Dildo

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Leona sissy maid deepthroat training and vibrator cum5:38
2 years ago xHamster

Leona sissy maid deepthroat training and vibrator cum

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Sucking Daddy's Cum out of HIS UNDERWEAR - Obedience Training3:29
2 years ago xHamster

Sucking Daddy's Cum out of HIS UNDERWEAR - Obedience Training

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Pps Training with Dominant Daddy - Rimming and Muscle Worship3:03
2 years ago xHamster

Pps Training with Dominant Daddy - Rimming and Muscle Worship

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Dominant Hunk Loves Ruining his BETA slave - Obedience Training2:43
2 years ago xHamster

Dominant Hunk Loves Ruining his BETA slave - Obedience Training

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Yaboy8989 sissy anal training3:25
2 years ago xHamster

Yaboy8989 sissy anal training

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Weekly anal stretching training so that the anal pussy stays nice and wide10:29
2 years ago xHamster

Weekly anal stretching training so that the anal pussy stays nice and wide

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Anal training in negative ball chastity to shaking orgasm9:25
2 years ago xHamster

Anal training in negative ball chastity to shaking orgasm

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White Femboy Gape Training - Sissy jaime isabella1:32
1 year ago xHamster

White Femboy Gape Training - Sissy jaime isabella

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Sissy Training 2 - Fuck Me Deep with a Monster Cock0:43
1 year ago xHamster

Sissy Training 2 - Fuck Me Deep with a Monster Cock

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Sissy Training 3 - Taking a Huge Cock and Massive Anal Beads1:08
1 year ago xHamster

Sissy Training 3 - Taking a Huge Cock and Massive Anal Beads

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Crossdresser Weekly anal stretch training with huge buttplugs9:33
1 year ago xHamster

Crossdresser Weekly anal stretch training with huge buttplugs

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Straight scandinavian boy moans from anal training + first bbc dildo8:54
1 year ago xHamster

Straight scandinavian boy moans from anal training + first bbc dildo

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YOUNG SISSY PUSSY TRAINING1:58
1 year ago xHamster

YOUNG SISSY PUSSY TRAINING

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My Sissy Cunt Training0:30
1 year ago xHamster

My Sissy Cunt Training

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Anal training and cum eating in micro chastity cage with penis plug29:26
1 year ago xHamster

Anal training and cum eating in micro chastity cage with penis plug

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Training To Take BBC5:15
1 year ago xHamster

Training To Take BBC

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Crossdresser with big fake breasts anal training6:47
1 year ago xHamster

Crossdresser with big fake breasts anal training

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Training My Pussy2:24
1 year ago xHamster

Training My Pussy

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Petite submissive sissy bbc training6:57
1 year ago xHamster

Petite submissive sissy bbc training

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Petite submissive sissy bbc training (2)5:24
1 year ago xHamster

Petite submissive sissy bbc training (2)

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Anal training and stretching1:11
1 year ago xHamster

Anal training and stretching

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Huge Anal Plug Training - Stretching My Hole & Pumping My Cock Foxhole0035:12
1 year ago xHamster

Huge Anal Plug Training - Stretching My Hole & Pumping My Cock Foxhole003

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TRAINING DILDO IN LINGERIE13:03
1 year ago xHamster

TRAINING DILDO IN LINGERIE

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Sissy Training - Dildo Fuck!1:16
1 year ago xHamster

Sissy Training - Dildo Fuck!

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Sissy Training - Dildo fuck part 2!1:56
1 year ago xHamster

Sissy Training - Dildo fuck part 2!

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Sexmachine Anal Training bi Slut Crossdresser12:42
1 year ago xHamster

Sexmachine Anal Training bi Slut Crossdresser

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Weekly anal stretch training part 19:16
1 year ago xHamster

Weekly anal stretch training part 1

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Weekly anal stretch training part 2 with nipple scene at the end11:45
1 year ago xHamster

Weekly anal stretch training part 2 with nipple scene at the end

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Requested sloppy throat training session9:45
1 year ago xHamster

Requested sloppy throat training session

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Sissy ass training day0:38
1 year ago xHamster

Sissy ass training day

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Spun Sissy Diligently Training With Using Sex Machine (11-25 pt 5)8:31
1 year ago xHamster

Spun Sissy Diligently Training With Using Sex Machine (11-25 pt 5)

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Dress up Anal Training Part18:12
1 year ago xHamster

Dress up Anal Training Part1

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Doggy style sissy training in a red dress and white pumps6:41
1 year ago xHamster

Doggy style sissy training in a red dress and white pumps

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Sissy Anal Training11:10
1 year ago xHamster

Sissy Anal Training

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Fat sissy in training!4:22
1 year ago xHamster

Fat sissy in training!

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Jinx Deepthroat and Double Penetration Training8:12
1 year ago xHamster

Jinx Deepthroat and Double Penetration Training

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Sky doing anal training stretching and depth12:12
1 year ago xHamster

Sky doing anal training stretching and depth

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Sissy CD Chub Anal Training with Big BBC Dildo1:05
1 year ago xHamster

Sissy CD Chub Anal Training with Big BBC Dildo

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Young bitch training deeptroath first time2:43
1 year ago xHamster

Young bitch training deeptroath first time

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Ass Play Training My Ass1:08
1 year ago xHamster

Ass Play Training My Ass

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Smooth young chastity sub hole training (Topped Toys Mordax 75)2:15
1 year ago xHamster

Smooth young chastity sub hole training (Topped Toys Mordax 75)

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Heavy rubber latex: Sissy in training swallows 4 loads of cum.6:21
1 year ago xHamster

Heavy rubber latex: Sissy in training swallows 4 loads of cum.

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Sissy Doggy Training5:04
1 year ago xHamster

Sissy Doggy Training

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Sissy Doggy Training 25:17
1 year ago xHamster

Sissy Doggy Training 2

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To prepare myself for fisting for the first time I break my ass with two bottles of two different sizes. Ass stretching training5:34
1 year ago xHamster

To prepare myself for fisting for the first time I break my ass with two bottles of two different sizes. Ass stretching training

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Extreme deepthroat training with fucking machine - part 1 of 27:45
1 year ago xHamster

Extreme deepthroat training with fucking machine - part 1 of 2

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Sissy Chayenne Dildo Training6:07
1 year ago xHamster

Sissy Chayenne Dildo Training

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20 years old teenie asshole and fist training for clarabitch5:28
1 year ago xHamster

20 years old teenie asshole and fist training for clarabitch

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SISSY ANAL TRAINING PART 113:01
1 year ago xHamster

SISSY ANAL TRAINING PART 1

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Big floppy Dildo Anal Training8:30
1 year ago xHamster

Big floppy Dildo Anal Training

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Madison's anal training2:25
1 year ago xHamster

Madison's anal training

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Training is work and fun to do.1:32
1 year ago xHamster

Training is work and fun to do.

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Training is so good.1:23
1 year ago xHamster

Training is so good.

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SISSY ANAL TRAINING PART 212:20
1 year ago xHamster

SISSY ANAL TRAINING PART 2

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SISSY ANAL TRAINING PART 213:57
1 year ago xHamster

SISSY ANAL TRAINING PART 2

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TRAINING ASS WITH MY FAVORITE DILDO23:56
1 year ago xHamster

TRAINING ASS WITH MY FAVORITE DILDO

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Sex Machine Sissy Training5:06
1 year ago xHamster

Sex Machine Sissy Training

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training time1:53
1 year ago xHamster

Training time

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Caged Slave Goes From Large Plug To Anal Training5:19
1 year ago xHamster

Caged Slave Goes From Large Plug To Anal Training

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Anal training and gaping0:34
1 year ago xHamster

Anal training and gaping

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asshole training,watch me insert 10 balls anal toy in my virgin ass16:25
1 year ago xHamster

Asshole training,watch me insert 10 balls anal toy in my virgin ass

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Hard When I have 25 years old I training my teenie ass with very huge dildo (Clarabitch)21:43
1 year ago xHamster

Hard When I have 25 years old I training my teenie ass with very huge dildo (Clarabitch)

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Training my little ass for a huge BBC cock14:38
1 year ago xHamster

Training my little ass for a huge BBC cock

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African Sissy Dick Training Part 22:00
1 year ago xHamster

African Sissy Dick Training Part 2

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1 year ago xHamster

African Sissy Dick Training Part 1

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1 year ago xHamster

African Sissy Dick Training Part 4

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Fellatio training1:58
1 year ago xHamster

Fellatio training

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Sloppy Sissy Spit Fetish Face Fuck Deepthroat Training Pt 2 Get ready - this slut tied their hair back and is about to suck you dry!0:45
1 year ago xHamster

Sloppy Sissy Spit Fetish Face Fuck Deepthroat Training Pt 2 Get ready - this slut tied their hair back and is about to suck you dry!

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TRAINING ASS WITH BLACK DILDO11:36
1 year ago xHamster

TRAINING ASS WITH BLACK DILDO

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1 year ago xHamster

HARCORE JOI UNCUT COCK Deepthroat Slave Training

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Handsfree training with my plug per Goddess' request!0:18
1 year ago xHamster

Handsfree training with my plug per Goddess' request!

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Anal training and stretching in flat negative ball chastity7:21
1 year ago xHamster

Anal training and stretching in flat negative ball chastity

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1 year ago xHamster

Ebony sissy dick training

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SLAVE TATTOO - Permanent Transformation - Obedience training3:08
1 year ago xHamster

SLAVE TATTOO - Permanent Transformation - Obedience training

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Chastity Training - Hardcore Humiliation SPH4:21
1 year ago xHamster

Chastity Training - Hardcore Humiliation SPH

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Satar Majhabi Mumin Cum Burqa Talim. Hijab Burka Muslim Training Full Video6:29
1 year ago xHamster

Satar Majhabi Mumin Cum Burqa Talim. Hijab Burka Muslim Training Full Video

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Training My SIssy's Hole3:07
1 year ago xHamster

Training My SIssy's Hole

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1 year ago xHamster

Sissy maid high heel training

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1 year ago xHamster

SometimesNiki sissy maid oral training

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1 year ago xHamster

SometimesNiki sissy maid anal training

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1 year ago xHamster

Weekly dildo and butt plug training for slutty crossdresser

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Chastity Sissy Anal Training6:58
1 year ago xHamster

Chastity Sissy Anal Training

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Plug Training7:37
1 year ago xHamster

Plug Training

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Sissy crossdresser anal training PART 19:51
1 year ago xHamster

Sissy crossdresser anal training PART 1

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1 year ago xHamster

Smooth Femboy Raine Training with Xl Dildo

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Permanent Chastity Humiliation - Obedience Training3:26
1 year ago xHamster

Permanent Chastity Humiliation - Obedience Training

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sissy dildo training for Blowjob5:21
1 year ago xHamster

Sissy dildo training for Blowjob

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Alpha & Beta Cum load Comparison - Fag Challenge - Slave Training3:26
1 year ago xHamster

Alpha & Beta Cum load Comparison - Fag Challenge - Slave Training

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Tasty Meal - Puppy Training3:26
1 year ago xHamster

Tasty Meal - Puppy Training

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Training a Man on a Deep Throat Simulator4:55
1 year ago xHamster

Training a Man on a Deep Throat Simulator

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1 year ago xHamster

Bondage training sissy slut whore

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1 year ago xHamster

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Training my throat to take your big juicy dick14:07
1 year ago xHamster

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Sissy Slut Training8:51
1 year ago xHamster

Sissy Slut Training

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Sissy Training Her Holes6:16
1 year ago xHamster

Sissy Training Her Holes

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1 year ago xHamster

Training my ass for the BNWO

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1 year ago xHamster

Sissy Fuckhole Training

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Sissygasm Training8:48
1 year ago xHamster

Sissygasm Training

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1 year ago xHamster

Sissy blowjob training

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African Sissy Dick Training Part 17:29
1 year ago xHamster

African Sissy Dick Training Part 1

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1 year ago xHamster

Sissy anal training and tight hole gaping so hoooot

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Sklavenboy Training1:21
1 year ago xHamster

Sklavenboy Training

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Sissy Femboy Training His Boyhole with a Big Dildo4:19
11 months ago xHamster

Sissy Femboy Training His Boyhole with a Big Dildo

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Workout Humiliation JOI - Obedience Training2:04
11 months ago xHamster

Workout Humiliation JOI - Obedience Training

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Anal training with 9in part 12:46
11 months ago xHamster

Anal training with 9in part 1

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Ruining your HOLE with PPs JOI - Obedience Training2:04
11 months ago xHamster

Ruining your HOLE with PPs JOI - Obedience Training

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Training with 9in dildo part 24:05
11 months ago xHamster

Training with 9in dildo part 2

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