Search results - Sissy Training

Total found: 393 videos (page 2)

Stepdad makes him work for it and train too7:49
9 months ago AnyGay

Stepdad makes him work for it and train too

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Timmy boy in chastity takes rough anal training xxx7:24
3 years ago xHamster

Timmy boy in chastity takes rough anal training xxx

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Sissy asspussy training with fucking machine6:56
3 years ago xHamster

Sissy asspussy training with fucking machine

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Cameron Neuton sucking and fucking Tony Genius after training7:49
10 months ago AnyGay

Cameron Neuton sucking and fucking Tony Genius after training

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Gay dudes share the gym for something else than training7:56
10 months ago AnyGay

Gay dudes share the gym for something else than training

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TRAINING ASS WITH FUCK MACHINE1:53
3 years ago xHamster

TRAINING ASS WITH FUCK MACHINE

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Sissy Training Showing in Thong and Seamless Pantyhose2:30
3 years ago xHamster

Sissy Training Showing in Thong and Seamless Pantyhose

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Sissy Training Thong Bulge with Pantyhose and Nylon Feet2:58
3 years ago xHamster

Sissy Training Thong Bulge with Pantyhose and Nylon Feet

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TRAINING ASS WITH BIG DILDO2:02
3 years ago xHamster

TRAINING ASS WITH BIG DILDO

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REAL SISSY TRAINING BY A REAL BBC MASTER1:13
3 years ago xHamster

REAL SISSY TRAINING BY A REAL BBC MASTER

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SISSY TRAINING - Slut riding Dildo - Cumming and Moaning4:00
3 years ago xHamster

SISSY TRAINING - Slut riding Dildo - Cumming and Moaning

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Sissy Training Verbal For UNCUT LOVER4:13
3 years ago xHamster

Sissy Training Verbal For UNCUT LOVER

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Pantyhose and Blue Heels Sissy Training with little Dick out2:03
3 years ago xHamster

Pantyhose and Blue Heels Sissy Training with little Dick out

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Training my sissy fuck ass1:39
3 years ago xHamster

Training my sissy fuck ass

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Sissy anal training with new dildo2:25
3 years ago xHamster

Sissy anal training with new dildo

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Pushing POOLBALL in with HUGE DILDO VIBRATOR and Dildo DP nipple clamps and Baseball Training18:11
3 years ago xHamster

Pushing POOLBALL in with HUGE DILDO VIBRATOR and Dildo DP nipple clamps and Baseball Training

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Beginner sissy anal training, trying to reach sissygasm5:16
3 years ago xHamster

Beginner sissy anal training, trying to reach sissygasm

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Latex slut Anal Training 1003202229:44
3 years ago xHamster

Latex slut Anal Training 10032022

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Fucking my Base Ball and a Coke can with Nipple Clamps and Deep Throating CUM SHOT Anal SLUT training33:07
3 years ago xHamster

Fucking my Base Ball and a Coke can with Nipple Clamps and Deep Throating CUM SHOT Anal SLUT training

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TRAINING ASS WITH GIANT DILDO5:36
3 years ago xHamster

TRAINING ASS WITH GIANT DILDO

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anal training practice for daddy1:12
3 years ago xHamster

Anal training practice for daddy

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Anal training with dildo1:48
3 years ago xHamster

Anal training with dildo

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Caged Anal Training Horny Dumb Sissy Slut1:28
3 years ago xHamster

Caged Anal Training Horny Dumb Sissy Slut

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Alxtoyboys dayli asshole training for bigger toys11:33
3 years ago xHamster

Alxtoyboys dayli asshole training for bigger toys

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Cheekyrider crossdresser sissy in pink skirt stockings training with 13 inch monster black dildo fucked my ass hard POV6:29
3 years ago xHamster

Cheekyrider crossdresser sissy in pink skirt stockings training with 13 inch monster black dildo fucked my ass hard POV

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Sissy Anal Training with 3 stage Plug1:15
3 years ago xHamster

Sissy Anal Training with 3 stage Plug

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Sissy training butt plug insert1:47
3 years ago xHamster

Sissy training butt plug insert

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TRAINING ASS WITH DOUBLE DILDO2:20
3 years ago xHamster

TRAINING ASS WITH DOUBLE DILDO

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Tied Sissy Ass training with big dildo fuck machine0:13
3 years ago xHamster

Tied Sissy Ass training with big dildo fuck machine

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Sissy Ass Training Routine0:38
3 years ago xHamster

Sissy Ass Training Routine

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Sissy Throat training2:48
3 years ago xHamster

Sissy Throat training

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TODAY IS DILDO FIST TRAINING2:36
3 years ago xHamster

TODAY IS DILDO FIST TRAINING

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hardcore chastity cage sounding anal gape training18:43
3 years ago xHamster

Hardcore chastity cage sounding anal gape training

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Sissy Denver in chastity, training her butt pussy5:42
3 years ago xHamster

Sissy Denver in chastity, training her butt pussy

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Ass Training2:29
3 years ago xHamster

Ass Training

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Sluty Courtney BBC Deep Throat Training3:07
3 years ago xHamster

Sluty Courtney BBC Deep Throat Training

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AMATEUR BISEXUAL, GAPING TRAINING VIBRATORS, XL DILDOS PLUGS (FULL VIDEO) ROSEBUD, POUNDING15:20
3 years ago xHamster

AMATEUR BISEXUAL, GAPING TRAINING VIBRATORS, XL DILDOS PLUGS (FULL VIDEO) ROSEBUD, POUNDING

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extreme deep anal fuck machine sissy training sub slut in cute corset and dress rides hard and deep, looses dildo inside14:17
3 years ago xHamster

Extreme deep anal fuck machine sissy training sub slut in cute corset and dress rides hard and deep, looses dildo inside

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100 pumps a new record for the long inflatable the sissy anal training is paying off5:20
3 years ago xHamster

100 pumps a new record for the long inflatable the sissy anal training is paying off

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Pole riding and extreme giant anal depth training dildo, practicing for whole arm fisting monster toy14:04
3 years ago xHamster

Pole riding and extreme giant anal depth training dildo, practicing for whole arm fisting monster toy

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Half hour chilling on the sex machine, daily anal fuck and depth training smoking lounging33:11
3 years ago xHamster

Half hour chilling on the sex machine, daily anal fuck and depth training smoking lounging

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My anal training in the morning was really horny its not the last video4:05
3 years ago xHamster

My anal training in the morning was really horny its not the last video

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anal training sissy - DP double ender and a dildo on a pole riding anal insertion self fist CD6:56
2 years ago xHamster

Anal training sissy - DP double ender and a dildo on a pole riding anal insertion self fist CD

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TRAINING DOUBLE DILDO FOR KITTY7:25
2 years ago xHamster

TRAINING DOUBLE DILDO FOR KITTY

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A lonely sunday night for a horny PhiliciaBtm. Best time for a sissyfication training (part.1)1:51
2 years ago xHamster

A lonely sunday night for a horny PhiliciaBtm. Best time for a sissyfication training (part.1)

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Crossdresser Anal Training 130820229:12
2 years ago xHamster

Crossdresser Anal Training 13082022

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Crossdresser Anal Training 190920229:38
2 years ago xHamster

Crossdresser Anal Training 19092022

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Crossdresser Bi Slut Anal training with 2 Tunnel Plugs an dildo fuck trought11:01
2 years ago xHamster

Crossdresser Bi Slut Anal training with 2 Tunnel Plugs an dildo fuck trought

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Wearing leggings at the gym, training my butt on thong and sportsbra2:53
2 years ago xHamster

Wearing leggings at the gym, training my butt on thong and sportsbra

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Crossdresser Machine Fuck Training Anal Orgasm8:01
2 years ago xHamster

Crossdresser Machine Fuck Training Anal Orgasm

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Crossdresser Slut Anal Training huge Dildos gaped hole8:27
2 years ago xHamster

Crossdresser Slut Anal Training huge Dildos gaped hole

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Sissy Twink CD Anal Dildo Training13:25
2 years ago xHamster

Sissy Twink CD Anal Dildo Training

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Crossdresser Anal Training Gaping Small cumshot Stockings Skirt anal Orgasm9:37
2 years ago xHamster

Crossdresser Anal Training Gaping Small cumshot Stockings Skirt anal Orgasm

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Deepthroat dildo sissy training with Kybellablue rayne5:44
2 years ago xHamster

Deepthroat dildo sissy training with Kybellablue rayne

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Sissy Panty Boy Masturbating repeating Sissy Panty Training Mantras2:08
2 years ago xHamster

Sissy Panty Boy Masturbating repeating Sissy Panty Training Mantras

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Sissy training turning him into a cock loving slut7:15
2 years ago xHamster

Sissy training turning him into a cock loving slut

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A young gay is training for the first sex with a trans, wants to put it in doggy style and start with the ass1:13
2 years ago xHamster

A young gay is training for the first sex with a trans, wants to put it in doggy style and start with the ass

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BHDL - N.V.A. BREATHTUB 2 - LATEX GASMASK TRAINING WITH PLASTIKBAG AND CUMMING6:55
2 years ago xHamster

BHDL - N.V.A. BREATHTUB 2 - LATEX GASMASK TRAINING WITH PLASTIKBAG AND CUMMING

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Training my tight sissy pussy8:04
2 years ago xHamster

Training my tight sissy pussy

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Sissy training asspussy slowly on machine in chastity5:39
2 years ago xHamster

Sissy training asspussy slowly on machine in chastity

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Little warm up training for my pighole2:49
2 years ago xHamster

Little warm up training for my pighole

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Sissy training asspussy with fuck machine for rough breeding, while her sissy clit is caged tight.10:01
2 years ago xHamster

Sissy training asspussy with fuck machine for rough breeding, while her sissy clit is caged tight.

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Depth training4:05
2 years ago xHamster

Depth training

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Sissy Training1:17
2 years ago xHamster

Sissy Training

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Sitting all the way on dildos - deep anal training4:09
2 years ago xHamster

Sitting all the way on dildos - deep anal training

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Rubber gimp anal training2:47
2 years ago xHamster

Rubber gimp anal training

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Hardcoreanalboy Daily Anal Training With Buttplug And Huge 12' inches Dildo6:58
2 years ago xHamster

Hardcoreanalboy Daily Anal Training With Buttplug And Huge 12' inches Dildo

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Ass training with extreme dildos20:54
2 years ago xHamster

Ass training with extreme dildos

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CD large anal training on a fuck Machine1:08
2 years ago xHamster

CD large anal training on a fuck Machine

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BHDL - SLUTTY SINKHOLE TRAINING - DOUBLE DILDO ASSFUCK WITH 5X25 CM AND 5,5X50 CM TOY -17:56
2 years ago xHamster

BHDL - SLUTTY SINKHOLE TRAINING - DOUBLE DILDO ASSFUCK WITH 5X25 CM AND 5,5X50 CM TOY -

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My girlfriend doesn't know I'm a secret BBC slut in training. Watch me satisfy my deepest desire of big black cock3:52
2 years ago xHamster

My girlfriend doesn't know I'm a secret BBC slut in training. Watch me satisfy my deepest desire of big black cock

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sexy slim messy crossdresser large BJ training well caged2:09
2 years ago xHamster

Sexy slim messy crossdresser large BJ training well caged

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A little bit of anal training some depth play and inflation ready for the big toys later27:17
2 years ago xHamster

A little bit of anal training some depth play and inflation ready for the big toys later

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Acrobatic Etude of Sissy Slut during Self Training and Outcome of This23:32
2 years ago xHamster

Acrobatic Etude of Sissy Slut during Self Training and Outcome of This

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Weekley Anal Stretching Training Crossdresser Slut 230220235:44
2 years ago xHamster

Weekley Anal Stretching Training Crossdresser Slut 23022023

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Weekley Sex Machine Piss Orgasm Anal Stretching Training Crossdresser Slut 2302202321:32
2 years ago xHamster

Weekley Sex Machine Piss Orgasm Anal Stretching Training Crossdresser Slut 23022023

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Chastity cage after a week of sissy training, dreaming of a daddy's cock2:20
2 years ago xHamster

Chastity cage after a week of sissy training, dreaming of a daddy's cock

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Sissy Training Asspussy's Depth With Large Dildo PT16:21
2 years ago xHamster

Sissy Training Asspussy's Depth With Large Dildo PT1

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Sissy Training Asspussy's Depth With Large Dildo PT27:24
2 years ago xHamster

Sissy Training Asspussy's Depth With Large Dildo PT2

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Anal dildo training1:46
2 years ago xHamster

Anal dildo training

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2 years ago xHamster

Sissy boy anal training in lingerie

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2 years ago xHamster

Sissy training asspussy with realistic black cock dildo using machine PT1

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BHDL - LATEXGLOVE BREATHPLAY - THROAT TRAINING WITH HAND AND DILDOSUCKING -3:11
2 years ago xHamster

BHDL - LATEXGLOVE BREATHPLAY - THROAT TRAINING WITH HAND AND DILDOSUCKING -

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SISSY TRAINING6:27
2 years ago xHamster

SISSY TRAINING

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2 years ago xHamster

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chubby sissy anal training2:24
2 years ago xHamster

Chubby sissy anal training

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2 years ago xHamster

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Ass to mouth training for sissy while she waits for daddy10:49
2 years ago xHamster

Ass to mouth training for sissy while she waits for daddy

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Doggy training and humiliation for slut and daddy master18:13
3 years ago FapHouse

Doggy training and humiliation for slut and daddy master

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Cheap Slut Part 2 – Sex Slave Training11:21
5 years ago FapHouse

Cheap Slut Part 2 – Sex Slave Training

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ANAL GAPE TRAINING AND FOOD PLAY WHILE WEARING CHASTITY CAGE16:10
2 years ago xHamster

ANAL GAPE TRAINING AND FOOD PLAY WHILE WEARING CHASTITY CAGE

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Bimbo Bambi BBC sissy training6:11
2 years ago xHamster

Bimbo Bambi BBC sissy training

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2 years ago xHamster

Bimbo sissy day training for BBC

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2 years ago xHamster

Sissy Whore Drool Fest, Dildo blowjob training.

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Loser cbt Training 20:47
2 years ago xHamster

Loser cbt Training 2

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2 years ago xHamster

Crossdresser Anal Deep Training with Organotoys Saber L

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2 years ago xHamster

Sissy Ivy outdoor anal training

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A goodnight for Sissy training8:35
2 years ago xHamster

A goodnight for Sissy training

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Training My Pussy to take Big Cock6:02
2 years ago xHamster

Training My Pussy to take Big Cock

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2 years ago xHamster

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2 years ago xHamster

Sissy anal training

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Alpha Disciplines His Bitch with HARDCORE Face Fuck - Obedience Training3:07
2 years ago xHamster

Alpha Disciplines His Bitch with HARDCORE Face Fuck - Obedience Training

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Alpha Feet That Make you SUBMIT - Obedience Training2:16
2 years ago xHamster

Alpha Feet That Make you SUBMIT - Obedience Training

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2 years ago xHamster

Anal training gaps

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Obedience Training - Worship Alpha 's ARMPITS - Lick them Clean2:41
2 years ago xHamster

Obedience Training - Worship Alpha 's ARMPITS - Lick them Clean

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Daddy Gives you PPS Sniffing Instructions JOI for gooner bator - Obedience Training3:47
2 years ago xHamster

Daddy Gives you PPS Sniffing Instructions JOI for gooner bator - Obedience Training

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2 years ago xHamster

Obedience Training - Piss Covered COCK CLEANING Deepthroat

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2 years ago xHamster

Sissy training

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2 years ago xHamster

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2 years ago xHamster

Blowjobs training & orgasm

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2 years ago xHamster

Obedience Training - Verbal Alpha Hunk Degrading Dirty Talk

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Daddy Teaches You LIFE with Huge Load of Cum - Obedience Training3:57
2 years ago xHamster

Daddy Teaches You LIFE with Huge Load of Cum - Obedience Training

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FAGS ARE MEANT to SERVE ALPHAS - Obedience Training3:17
2 years ago xHamster

FAGS ARE MEANT to SERVE ALPHAS - Obedience Training

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2 years ago xHamster

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2 years ago xHamster

Sissygasm for training slut

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2 years ago xHamster

Mind Breaking PPS Training JOI - Obey Commands, Slave

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PP's Slave Training - SUBMIT. GOON. REPEAT3:09
2 years ago xHamster

PP's Slave Training - SUBMIT. GOON. REPEAT

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Plug Play - Training My Slut Hole0:42
2 years ago xHamster

Plug Play - Training My Slut Hole

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Worship Daddy's Feet - Obedience Training3:35
2 years ago xHamster

Worship Daddy's Feet - Obedience Training

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Gagging on Daddy's Cock while He is Smoking - Slave Training3:20
2 years ago xHamster

Gagging on Daddy's Cock while He is Smoking - Slave Training

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