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    • Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      18:39
      Spiked Chastity Cage Torment - Sissy Maids Self Bondage
      Derek6699
      102.2K views
    • Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
      17:38
      Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
      Derek6699
      74.9K views
    • Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post
      32:38
      Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post
      Derek6699
      66K views
    • Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged
      25:04
      Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged
      Derek6699
      24.4K views
    • Sissy Maids Spiked Chastity Cage Self Bondage Torment
      15:12
      Sissy Maids Spiked Chastity Cage Self Bondage Torment
      Derek6699
      13.6K views
    • Sissy Maid Self Bondage in Spiked Chastity Cage
      20:08
      Sissy Maid Self Bondage in Spiked Chastity Cage
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    • Sissy Maids Self Bondage Spiked Chastity Cage Torment for the Holidays
      10:07
      Sissy Maids Self Bondage Spiked Chastity Cage Torment for the Holidays
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      4.1K views
    • Sissy Maids Spiked Chastity Cage Self Bondage in New Boots
      18:24
      Sissy Maids Spiked Chastity Cage Self Bondage in New Boots
      Derek6699
      4.7K views
    • Spiked Chastity Cage Self Bondage
      26:49
      Spiked Chastity Cage Self Bondage
      Derek6699
      12.5K views
    • Spiked Chastity Cage Self Bondage Sissy Maid
      17:59
      Spiked Chastity Cage Self Bondage Sissy Maid
      Derek6699
      9.5K views
    • sissy maid self bondage, spiked chastity cage
      08:03
      sissy maid self bondage, spiked chastity cage
      Derek6699
      8.4K views
    • Black blow up spiked butt plug for my S&M Daddies!
      08:37
      Black blow up spiked butt plug for my S&M Daddies!
      Victoria Lecherri
      44.1K views
    • Femmby painslut plays with spiked bracelet and ruins orgasm
      05:31
      Femmby painslut plays with spiked bracelet and ruins orgasm
      Onlyfans
      3.3K views
    • Pain and pleasure, chastity and lust, Part 2
      01:15:02
      Pain and pleasure, chastity and lust, Part 2
      343.3K views
    • Pain and pleasure, chastity and lust,  Part 1
      51:35
      Pain and pleasure, chastity and lust, Part 1
      127.2K views
    • Compilation with Weekly Episodes from the pain whore Alina
      02:05
      Compilation with Weekly Episodes from the pain whore Alina
      alinanightsky
      65.7K views
    • Sissy Maid Icy Hot Wooden Pony Punishment 2
      23:29
      Sissy Maid Icy Hot Wooden Pony Punishment 2
      Derek6699
      39.8K views
    • Sissy Maids Punishment
      07:53
      Sissy Maids Punishment
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      28.1K views
    • Sissy Nipple Cow Chastity Nipple Pump Electro Pain
      02:06
      Sissy Nipple Cow Chastity Nipple Pump Electro Pain
      Titten-Sau
      26.3K views
    • Icy Hot Wooden Pony Self Bondage Torture
      17:40
      Icy Hot Wooden Pony Self Bondage Torture
      Derek6699
      26.7K views
    • Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
      00:43
      Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
      Allmylinks
      43.6K views
    • Sissy Maid - Pain & Pleasure Bondage
      14:55
      Sissy Maid - Pain & Pleasure Bondage
      Derek6699
      17.5K views
    • Candle Wax & Chastity Go Together like PB & Jelly
      07:05
      Candle Wax & Chastity Go Together like PB & Jelly
      MJ
      7.7K views
    • Fat Sissy light ball torture and wax play in chastity
      03:02
      Fat Sissy light ball torture and wax play in chastity
      Chubby Sissy Dani
      5.4K views
    • Plugged sissy, nipple clamps, caged dick whips her ass and cock with nettles before making herself cum with the vibro
      06:08
      Plugged sissy, nipple clamps, caged dick whips her ass and cock with nettles before making herself cum with the vibro
      MyLolaTrav
      5.9K views
    • Sissy painful chastity cage cumshot with hair clip
      01:00
      Sissy painful chastity cage cumshot with hair clip
      Many Vids
      5.5K views
    • Sexy metal spiked heels
      01:59
      Sexy metal spiked heels
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    • SPIKE CLAMPS OFF AFTER 9 KILO tepelgewichtheffen
      01:16
      SPIKE CLAMPS OFF AFTER 9 KILO tepelgewichtheffen
      22.5K views
    • Carol C. Tranny Slutwhore in Steel Spike Stilettoes
      14:13
      Carol C. Tranny Slutwhore in Steel Spike Stilettoes
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    • Preview of Piggy Gets a Spiked Toilet Brush in the ass
      01:00
      Preview of Piggy Gets a Spiked Toilet Brush in the ass
      FapHouse
      43.6K views
    • Spike gets pegged by Lisa whilst sucking TGirl Aprils cock.
      04:47
      Spike gets pegged by Lisa whilst sucking TGirl Aprils cock.
      Spike Essex
      27.4K views
    • Kinky iris with new spike clamps, very painfull first time
      06:52
      Kinky iris with new spike clamps, very painfull first time
      9.5K views
    • Girl Fucks Sissy with Spiked Vibro Cock Outdoor
      01:09
      Girl Fucks Sissy with Spiked Vibro Cock Outdoor
      Many Vids
      3.9K views
    • Spiked dildo anal masturbation shemale
      03:09
      Spiked dildo anal masturbation shemale
      Lilith Na
      8.6K views
    • Rebecca spikes her balls and masturbates
      05:09
      Rebecca spikes her balls and masturbates
      Rebeccafuxx
      7.4K views
    • Sissy Bunny teases while stair walking in elegant spiked heels
      02:28
      Sissy Bunny teases while stair walking in elegant spiked heels
      Danicd94
      3.7K views
    • TS SPIKE
      02:15
      TS SPIKE
      15.6K views
    • Nice horny jerking off in spiked bra and red panties
      03:21
      Nice horny jerking off in spiked bra and red panties
      Mitchie
      691 views
    • Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll
      07:14
      Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll
      Jessica Bloom
      96.4K views
    • I fuck my roommate and fills my butthole full of cum while i'm in chastity
      05:45
      I fuck my roommate and fills my butthole full of cum while i'm in chastity
      missangell_
      688K views
    • TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
      09:05
      TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
      Adam Castle
      386.5K views
    • BBC Fucks a Slutty Crossdresser Without Limits
      32:44
      BBC Fucks a Slutty Crossdresser Without Limits
      FapHouse
      394.6K views
    • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      18:27
      Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      Vane03_siss
      231.7K views
    • Sissy Sex Slave
      07:00
      Sissy Sex Slave
      Kapri Sun
      60.1K views
    • 2032 - the Bwno Future
      15:06
      2032 - the Bwno Future
      ChristineWest120
      120.4K views
    • Bound sissy in chastity gets BBC
      07:46
      Bound sissy in chastity gets BBC
      953.1K views
    • Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
      05:27
      Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
      ActorFab
      242.5K views
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