New Tranny Videos Tagged with sissy chastity

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Sissy femboy in chastity taking big dildos in her ass and trying and sissygasm 19:06
Sissy femboy in chastity taking big dildos in her ass and trying and sissygasm
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Mike Ass Fucks Sissy Charlotte While She is Locked in EStim Chastity Cage 16:07
Mike Ass Fucks Sissy Charlotte While She is Locked in EStim Chastity Cage
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Sissy gets anal machine fucked by mistress!!! 15:21
Sissy gets anal machine fucked by mistress!!!
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Sissy Maid Chained to Bed in Chastity, Gagged and Leather Bondage Mitts Handcuffed on 34:41
Sissy Maid Chained to Bed in Chastity, Gagged and Leather Bondage Mitts Handcuffed on
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"I've Learned To Enjoy Not Cumming" Sissy Femboy Chastity & Self Foot Worship + CBT Tranny Ball Slap 9:32
"I've Learned To Enjoy Not Cumming" Sissy Femboy Chastity & Self Foot Wors...
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Sissy Mara Jade's Entire Chastity Sissygasm Compilation! 10:08
Sissy Mara Jade's Entire Chastity Sissygasm Compilation!
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SisK CD in purple EP1 A tiny purple cock cage wearing 11:10
SisK CD in purple EP1 A tiny purple cock cage wearing
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Crossdresser in chastity and his daily dildo challenge 8:42
Crossdresser in chastity and his daily dildo challenge
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Sissy Maid Self Bondage in Spiked Chastity Cage 20:08
Sissy Maid Self Bondage in Spiked Chastity Cage
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Sissy fucked with some monster dildos 42:25
Sissy fucked with some monster dildos
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Daddy Unlocks Sissy Femboy Chrissy's Clitty & Sucks It 12:03
Daddy Unlocks Sissy Femboy Chrissy's Clitty & Sucks It
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Sissy Nun Astrid Apathy Sissygasm in Chastity 11:06
Sissy Nun Astrid Apathy Sissygasm in Chastity
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sissy dildo training 8:11
sissy dildo training
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Sissy training: slut in chastity having fun on huge anal toys, multiple sissygasms 29:58
Sissy training: slut in chastity having fun on huge anal toys, multiple sissygasms
6.7K
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Anal sex with sissymaid Kitsy in chastity and bunny ears 8:10
Anal sex with sissymaid Kitsy in chastity and bunny ears
4.0K
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Armbinder tied to Chastity Cage Sissy Maid Self Bondage 47:08
Armbinder tied to Chastity Cage Sissy Maid Self Bondage
2.0K
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Astrid Apathy Night Time Public Display in Chastity 23:12
Astrid Apathy Night Time Public Display in Chastity
2.0K
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SisK dressing up pink satin nightgown 13:00
SisK dressing up pink satin nightgown
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daddy made me a new milking toy on my chastity 1:54
daddy made me a new milking toy on my chastity
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SisK release her penis from chastity device and play with her horny penis after her ass being plugged. 10:38
SisK release her penis from chastity device and play with her horny penis after he...
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Sissy Maid Cuffed Spread Eagle in Steel Chastity Belt and Huge Dildo 20:12
Sissy Maid Cuffed Spread Eagle in Steel Chastity Belt and Huge Dildo
1.6K
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SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage 8:17
SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage
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Sissy Francesca anal play in chastity 14:26
Sissy Francesca anal play in chastity
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This Is How You Train Your Sissy Pussy (Riding Compilation) 11:34
This Is How You Train Your Sissy Pussy (Riding Compilation)
3.3K
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Sissy Hope Compilation 4 42:50
Sissy Hope Compilation 4
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COSPLAY CHASTITY CAGE WALKING BY SISSYKAT 2:43
COSPLAY CHASTITY CAGE WALKING BY SISSYKAT
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Sissy Maid Ballet Boot Training 18:22
Sissy Maid Ballet Boot Training
2.0K
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Caged Sissy with a Bullwhip Lick and Swallow Her Cum from the Hand 3:37
Caged Sissy with a Bullwhip Lick and Swallow Her Cum from the Hand
2.3K
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Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage! 8:49
Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage!
1.9K
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Cute Sissy Puts in Some Some Serious Deep Throat Training 7:23
Cute Sissy Puts in Some Some Serious Deep Throat Training
4.8K
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Theresa Cums riding her favourite vibrating big black dildo 46:45
Theresa Cums riding her favourite vibrating big black dildo
2.3K
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Sissy Hope, the little naughty slut snapchat humiliation sex chat compilation 19:49
Sissy Hope, the little naughty slut snapchat humiliation sex chat compilation
2.1K
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Sissy crossdresser femboy ruins her own orgasm with hardcore ballbusting 9:03
Sissy crossdresser femboy ruins her own orgasm with hardcore ballbusting
2.7K
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Squeezing a penis into a micro cage 11:40
Squeezing a penis into a micro cage
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Angora Sissy Chastity Cum 8:27
Angora Sissy Chastity Cum
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Sissy in a cow's suit rides a dildo, squirts and cums hands free | Video by LevkoNoya 6:27
Sissy in a cow's suit rides a dildo, squirts and cums hands free | Video by LevkoNoya
3.8K
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BDSM mistress plays with her sissy girl 11:37
BDSM mistress plays with her sissy girl
1.6K
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Sissy in chastity playing with fuck machine 7:16
Sissy in chastity playing with fuck machine
3.6K
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Sissy slut Hope woke up horny, and this is what happened, Good Morning Master 38:36
Sissy slut Hope woke up horny, and this is what happened, Good Morning Master
2.1K
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Alpha male fucking sissy bareback, cums inside and she starts masturbating like a girl in chastity 14:40
Alpha male fucking sissy bareback, cums inside and she starts masturbating like a ...
2.3K
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Sissy chastity (part 1) 9:28
Sissy chastity (part 1)
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Sissy Maids Suspension Self Bondage 9:58
Sissy Maids Suspension Self Bondage
1.2K
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Sissy Hope, the little naughty slut snapchat humiliation sex chat compiltaion 19:49
Sissy Hope, the little naughty slut snapchat humiliation sex chat compiltaion
1.8K
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SissyBoy - I Don't Need a Pussy to CUM ( SissyBoy life ) 2:40
SissyBoy - I Don't Need a Pussy to CUM ( SissyBoy life )
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Sissy Hope pink cosplay exposing her hole and playing with vibrator horny, slut and humiliated 15:14
Sissy Hope pink cosplay exposing her hole and playing with vibrator horny, slut an...
1.6K
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Sissy cums in cage to being degraded as Mistresss trash recycling pig angel Scarlett black 11:56
Sissy cums in cage to being degraded as Mistresss trash recycling pig angel Scarle...
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Spiked Chastity Cage Self Bondage 26:49
Spiked Chastity Cage Self Bondage
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Trans Buttslut just cann't stop destroing her asshole with Huge Black Dildos cause it feels too good 10:10
Trans Buttslut just cann't stop destroing her asshole with Huge Black Dildos cause...
875
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Icy Hot Wooden Pony Self Bondage Torture 17:40
Icy Hot Wooden Pony Self Bondage Torture
1.4K
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Dildo ride in chastity sissygasm 10:44
Dildo ride in chastity sissygasm
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Chastity sissy cums handsfree from huge buttplug 11:02
Chastity sissy cums handsfree from huge buttplug
1.3K
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Sissy Maddy out in the wild playing with her ass while having her clitty locked 8:57
Sissy Maddy out in the wild playing with her ass while having her clitty locked
2.2K
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Prized Breeding Sissy Cows First Day On The Farm 8:47
Prized Breeding Sissy Cows First Day On The Farm
1.3K
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Sissy Maid Icy Hot Wooden Pony Punishment 2 23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
1.4K
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Straight Jacket Bondage - Sissy Maid 8:54
Straight Jacket Bondage - Sissy Maid
1.2K
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Cock riding sissy compilation 3:59
Cock riding sissy compilation
32
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Sissy twink rubs its locked little dicklet on cam and cums 8:49
Sissy twink rubs its locked little dicklet on cam and cums
1.6K
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Sissy Maids Self Bondage Fiddle and Ballet Boots 30:13
Sissy Maids Self Bondage Fiddle and Ballet Boots
1.6K
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Sissy Home Video presentation: The little naughty slut owned by internet 12:29
Sissy Home Video presentation: The little naughty slut owned by internet
4.5K
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Sissy Maid - Pain & Pleasure Bondage 14:56
Sissy Maid - Pain & Pleasure Bondage
1.2K
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Locked Sissy Maid Cleans Window 2:13
Locked Sissy Maid Cleans Window
144
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Sissy Hope anal fuck session with fuckmachine and lush 27:02
Sissy Hope anal fuck session with fuckmachine and lush
2.4K
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Caged sissy asspussy training warm up 8:19
Caged sissy asspussy training warm up
1.2K
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Sissy Hope Playing with her naughty hole. 15:44
Sissy Hope Playing with her naughty hole.
812
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Machine pumping in chastity cage 8:08
Machine pumping in chastity cage
760
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Sissy's Beautiful Ass Fucked Hard ! 1:08
Sissy's Beautiful Ass Fucked Hard !
476
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SisK CD in purple EP2 dressing up sexy silky panties. 11:25
SisK CD in purple EP2 dressing up sexy silky panties.
999
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Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded 19:27
Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded
1.1K
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Astrid Apathy puts on Erotic Show in Thigh High Socks and Chastity 24:45
Astrid Apathy puts on Erotic Show in Thigh High Socks and Chastity
992
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Sissy Slut Bess repeatedly interrupted trying to cum in her car 9:30
Sissy Slut Bess repeatedly interrupted trying to cum in her car
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Dawn Rides Black Destroyer in Flat Plate Chastity 8:49
Dawn Rides Black Destroyer in Flat Plate Chastity
778
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Sissy Luxiana in chastity cage and fake penis 25:04
Sissy Luxiana in chastity cage and fake penis
901
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White Dirty Sissy Slut Fuck by Huge BBC Dildo penetrated while Locked in Chastity 4:11
White Dirty Sissy Slut Fuck by Huge BBC Dildo penetrated while Locked in Chastity
519
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Caged Ass Training Sissy Bimbo Brandynette Lovense Hush 45mm Anal Plug 19:05
Caged Ass Training Sissy Bimbo Brandynette Lovense Hush 45mm Anal Plug
1.7K
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Sissy latexdoll pissing and anal training 24:18
Sissy latexdoll pissing and anal training
1.4K
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Pale little crossdresser rubs her clit in chastity and cums 8:32
Pale little crossdresser rubs her clit in chastity and cums
1.3K
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Sissy stretching her ass for you with eye contact 11:54
Sissy stretching her ass for you with eye contact
751
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Sissy chastity training with big black dildo 9:18
Sissy chastity training with big black dildo
1.7K
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Sissy in red nightie copulates her butt whilst locked in chastity 41:04
Sissy in red nightie copulates her butt whilst locked in chastity
590
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Sabrina Skye anal bouncing compilation. She fills her hole while locked up in chastity. 4:08
Sabrina Skye anal bouncing compilation. She fills her hole while locked up in chas...
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Slut Playing In Chastity And Exposing Her Hard Clit Afterwards 8:03
Slut Playing In Chastity And Exposing Her Hard Clit Afterwards
576
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Negative Chastity cum with vibrator 2:12
Negative Chastity cum with vibrator
159
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Trans girl in chastity rides dildo ft. AnimaLauren 22:36
Trans girl in chastity rides dildo ft. AnimaLauren
1.7K
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Lots of cum, throat, dildo and fucking. This got it all. Best of 22 23:26
Lots of cum, throat, dildo and fucking. This got it all. Best of 22
642
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Anal pumping with XXL Dildos 31:22
Anal pumping with XXL Dildos
480
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Redhead shemale Huge cum in chastity 2:15
Redhead shemale Huge cum in chastity
541
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Sissy Pony Bride rides her dildo stand 8:47
Sissy Pony Bride rides her dildo stand
412
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Sissys Balls Busted By BBC 0:58
Sissys Balls Busted By BBC
211
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chubby chastity slut gets to vibe 2:05
chubby chastity slut gets to vibe
908
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SissyBoy - Multiple Cumshots Riding Big Dildo 4:05
SissyBoy - Multiple Cumshots Riding Big Dildo
1.5K
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CD Sissy Fem Milf Mila Ferrari Solo Play 2:18
CD Sissy Fem Milf Mila Ferrari Solo Play
1.3K
100%
rubbing lotion on chastity cage and groin and skin. turn me on baby sissy talking about transition 13:58
rubbing lotion on chastity cage and groin and skin. turn me on baby sissy talking ...
1.5K
100%
Sissy Hope vs Big Plug, the desperate and nasty urge to expand her boipussi until sissigasm. 24:55
Sissy Hope vs Big Plug, the desperate and nasty urge to expand her boipussi until ...
1.5K
100%
Dog leash & chastity 14:34
Dog leash & chastity
964
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Femboy leaves the chastity cage to wank her clitoris and make herself cum 14:44
Femboy leaves the chastity cage to wank her clitoris and make herself cum
663
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Sissy Sophie Banging Her Marital-Device Like a Bitch (Compilation) 10:50
Sissy Sophie Banging Her Marital-Device Like a Bitch (Compilation)
783
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Masturbating like a real Sissy gurl 6:42
Masturbating like a real Sissy gurl
233
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Alexa fucking ass-pussy with large Beowulf in chastity & corset 7:05
Alexa fucking ass-pussy with large Beowulf in chastity & corset
279
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Holy: Uncaging Teasing Cumzies with Your Secret Sissy Holy 8:51
Holy: Uncaging Teasing Cumzies with Your Secret Sissy Holy
490
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Sissy fucks Dildo in chastity 13:22
Sissy fucks Dildo in chastity
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Sissy hope riding dildo very horny until cum 23:23
Sissy hope riding dildo very horny until cum
1.0K
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Pegging him till he cums 16:50
Pegging him till he cums
766
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Chatty Crossdresser chats another time... and tries recent plug 2023-02-26 part 1 1:03:39
Chatty Crossdresser chats another time... and tries recent plug 2023-02-26 part 1
671
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Ilandis in a chastity thong and nylons has enjoyment with his butthole, copulates himself with an artificial dick 9:22
Ilandis in a chastity thong and nylons has enjoyment with his butthole, copulates ...
844
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Sissy Hope masturbing her stretched and naked hole with delicious dildo, drilling harder and deeper until get wet 14:46
Sissy Hope masturbing her stretched and naked hole with delicious dildo, drilling ...
1.1K
100%
Skitty in Pump it Up 11:24
Skitty in Pump it Up
450
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Sissy Maid Self Bondage with Huge Dildo in Bed 11:08
Sissy Maid Self Bondage with Huge Dildo in Bed
1.4K
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Closed girl made a golden fountain and filled a tube with cum 10:55
Closed girl made a golden fountain and filled a tube with cum
791
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Chloe in Red Lingerie attempting to sissygasm 29:36
Chloe in Red Lingerie attempting to sissygasm
689
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Sissy dude smashed by fuckmachine 18:53
Sissy dude smashed by fuckmachine
292
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Riding my large STUD-HORSE wearing my hot high heels 14:04
Riding my large STUD-HORSE wearing my hot high heels
808
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JuliaSissy Drilled and cum eating 10:34
JuliaSissy Drilled and cum eating
578
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Erika Oak Cums In Chastity From Her Vibrator 8:14
Erika Oak Cums In Chastity From Her Vibrator
1.5K
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Self Bondage Armbinder Hogtie in PVC Catsuit and Lycra Bodysuit with Chastity Belt and Dildo Locked in Place 19:08
Self Bondage Armbinder Hogtie in PVC Catsuit and Lycra Bodysuit with Chastity Belt...
1.7K
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Sissy Plays with Toys with Training Video 4:28
Sissy Plays with Toys with Training Video
1.0K
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Sissy Maids Predicament Bondage Fun, Drink to Escape. 9:24
Sissy Maids Predicament Bondage Fun, Drink to Escape.
1.4K
100%
femboi sloppy and hard anal ride with dildo 4k 60fps 8:20
femboi sloppy and hard anal ride with dildo 4k 60fps
863
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Skitty&M&L in Our first fun Together 21:22
Skitty&M&L in Our first fun Together
590
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Skitty in Anal Plug progression Stretching 24:37
Skitty in Anal Plug progression Stretching
594
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SissyGurlChloe Showing off and using her buttplug collection 21:34
SissyGurlChloe Showing off and using her buttplug collection
445
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