Showing 80 of 758 results for "Training A Sissy".
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Search Results for “Training A Sissy”

Sissy training: Evil Woman dominates and humiliates Kiro Queen in a hardcore femdom session (Evil Woman, kiro queen) 11:59
Sissy training: Evil Woman dominates and humiliates Kiro Queen in a hardcore femdom session (Evil Woman, kiro queen)
Evil Woman kiro queen
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23
Ciren Verde dominates her husband with strapon and BBD while training him to be a sissy boy (Ciren Verde) 07:56
Ciren Verde dominates her husband with strapon and BBD while training him to be a sissy boy (Ciren Verde)
Ciren Verde
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Watch My Husband Be A Sissy And Begs For His Feet: Miss Raven Training Zero August 8, 2025 Onlyfans Video (miss raven) 12:55
Watch My Husband Be A Sissy And Begs For His Feet: Miss Raven Training Zero August 8, 2025 Onlyfans Video (miss raven)
miss raven
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Ciren Verde's husband interviews her as her sissy boyfriend, showing her who's boss and humiliating her in every way imaginable (Ciren Verde) 06:14
Ciren Verde's husband interviews her as her sissy boyfriend, showing her who's boss and humiliating her in every way imaginable (Ciren Verde)
Ciren Verde
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Ciren Verde's BTS Session with Sissy Boi: Dildosucking, Slutty Humiliation, and Sissy Training (Ciren Verde) 07:55
Ciren Verde's BTS Session with Sissy Boi: Dildosucking, Slutty Humiliation, and Sissy Training (Ciren Verde)
Ciren Verde
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Interracial sissytraining: Ciren Verde humiliates BBC while training her with manyvids (Ciren Verde) 13:27
Interracial sissytraining: Ciren Verde humiliates BBC while training her with manyvids (Ciren Verde)
Ciren Verde
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Ciren Verde humiliates her sissy hubby with a chastity device and a cockcage (Ciren Verde) 09:04
Ciren Verde humiliates her sissy hubby with a chastity device and a cockcage (Ciren Verde)
Ciren Verde
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148
Ciren Verde dominates as her husband trains her with his BBC (Ciren Verde) 11:38
Ciren Verde dominates as her husband trains her with his BBC (Ciren Verde)
Ciren Verde
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132
Chastity April Nicknamed Chastity April 02 is a Sissy Training Pro who loves to suck and dominate you (Chastity April) 08:30
Chastity April Nicknamed Chastity April 02 is a Sissy Training Pro who loves to suck and dominate you (Chastity April)
Chastity April
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113
Ciren Verde's strapon training for her ciren verde husband (Ciren Verde) 19:14
Ciren Verde's strapon training for her ciren verde husband (Ciren Verde)
Ciren Verde
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Watch Ciren Verde dominate and humiliate her sissy training partner with a strapon (Ciren Verde) 08:00
Watch Ciren Verde dominate and humiliate her sissy training partner with a strapon (Ciren Verde)
Ciren Verde
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Ciren Verde Sissy Training: Intense BBC Gangbang with Verbal Humiliation & BBC Slutishment (Ciren Verde) 07:48
Ciren Verde Sissy Training: Intense BBC Gangbang with Verbal Humiliation & BBC Slutishment (Ciren Verde)
Ciren Verde
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Ciren Verde's Ass Stretching Skills: Sissy Husband and Sissy Boy Ass Training with Anal Play (Ciren Verde) 02:19
Ciren Verde's Ass Stretching Skills: Sissy Husband and Sissy Boy Ass Training with Anal Play (Ciren Verde)
Ciren Verde
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Ciren Verde gets a training in maskfetish cosplay by her hubby's side (Ciren Verde) 03:47
Ciren Verde gets a training in maskfetish cosplay by her hubby's side (Ciren Verde)
Ciren Verde
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Ciren Verde worships your feet in this sissy training video with multiple chastity devices (Ciren Verde) 27:47
Ciren Verde worships your feet in this sissy training video with multiple chastity devices (Ciren Verde)
Ciren Verde
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Ciren Verde BTS Threesome Pegging & Straponfucking in Sissy Training (Ciren Verde) 20:41
Ciren Verde BTS Threesome Pegging & Straponfucking in Sissy Training (Ciren Verde)
Ciren Verde
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126
Watch Chastity April's 12-05 2025 Onlyfans Video Sissy Anal Training & Feet Fetish (Chastity April) 06:47
Watch Chastity April's 12-05 2025 Onlyfans Video Sissy Anal Training & Feet Fetish (Chastity April)
Chastity April
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109
Ciren Verde's BTS Black Cock Sissy Training: Interracial Bi-Curious BDSM Session with Ciren Verde (Ciren Verde) 12:04
Ciren Verde's BTS Black Cock Sissy Training: Interracial Bi-Curious BDSM Session with Ciren Verde (Ciren Verde)
Ciren Verde
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134
Ciren Verde and her husband have a wild anal threesome with some sissy training (Ciren Verde) 07:37
Ciren Verde and her husband have a wild anal threesome with some sissy training (Ciren Verde)
Ciren Verde
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105
Watch Ciren Verde's intense Anal Training with BBD Dildo & Strapon (Ciren Verde) 19:15
Watch Ciren Verde's intense Anal Training with BBD Dildo & Strapon (Ciren Verde)
Ciren Verde
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Sissy Boi Ciren Verde goes wild with strapon and pegging in hardcore anal training (Ciren Verde) 16:46
Sissy Boi Ciren Verde goes wild with strapon and pegging in hardcore anal training (Ciren Verde)
Ciren Verde
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Ciren Verde dominates her husband with a hot femdom dildo session (Ciren Verde) 08:53
Ciren Verde dominates her husband with a hot femdom dildo session (Ciren Verde)
Ciren Verde
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117
Goddess Vanessa dominates and trains you to be a sissy slave (Goddess Vanessa) 15:58
Goddess Vanessa dominates and trains you to be a sissy slave (Goddess Vanessa)
Goddess Vanessa
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240
"Goddess Vanessa" sissy sluts, sissy training, gay humiliation, gay jerk off instructions, gay masturbation instructions FAG WEEKLY 24 7 Manyvids (Goddess Vanessa) 08:37
"Goddess Vanessa" sissy sluts, sissy training, gay humiliation, gay jerk off instructions, gay masturbation instructions FAG WEEKLY 24 7 Manyvids (Goddess Vanessa)
Goddess Vanessa
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151
"Goddess Vanessa" femdom pov, sissy sluts, sissy training, sissification, make me bi Turned Bi Suck Officer s COCK Manyvids (Goddess Vanessa) 08:05
"Goddess Vanessa" femdom pov, sissy sluts, sissy training, sissification, make me bi Turned Bi Suck Officer s COCK Manyvids (Goddess Vanessa)
Goddess Vanessa
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162
Goddess Vanessa's Ass-to-Mouth FAG training will make you a better sissy (Goddess Vanessa) 11:39
Goddess Vanessa's Ass-to-Mouth FAG training will make you a better sissy (Goddess Vanessa)
Goddess Vanessa
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Goddess Vanessa dominates your life with JOI and Sissy Training (Goddess Vanessa) 08:47
Goddess Vanessa dominates your life with JOI and Sissy Training (Goddess Vanessa)
Goddess Vanessa
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Tara Tainton's intense Anal Training: A Sissy's Only Hope for Orgasm Control! (Tara Tainton) 22:43
Tara Tainton's intense Anal Training: A Sissy's Only Hope for Orgasm Control! (Tara Tainton)
Tara Tainton
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"Helenas Cock Quest" cross-dressing, pegging, sissy sluts, sissy training, strap-on I Train Sissy slut bitch boi Pt 2 of 2 Manyvids (Helenas Cock Quest) 18:25
"Helenas Cock Quest" cross-dressing, pegging, sissy sluts, sissy training, strap-on I Train Sissy slut bitch boi Pt 2 of 2 Manyvids (Helenas Cock Quest)
Helenas Cock Quest
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"Goddess Vanessa" feminization, jerk off instruction, sissy sluts, sissy training, sissification Turn YOU Into PINK BUTTERFLY JOI Manyvids (Goddess Vanessa) 09:19
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Goddess Vanessa
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"SavannahxSiren" redhead, sfw, sissification, sissy, sissysluts, sissytraining Transforming You Into My Sissy Kitty Manyvids (SavannahxSiren) 06:31
"SavannahxSiren" redhead, sfw, sissification, sissy, sissysluts, sissytraining Transforming You Into My Sissy Kitty Manyvids (SavannahxSiren)
SavannahxSiren
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"Freya Reign" femdom, feminization, gfe, pov, sfw, sissification Girls Night Feminization Manyvids (Freya Reign) 05:43
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Freya Reign
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Goddess Vanessa
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"Goddess Vanessa" embarrassed naked female, imposed crossdressing, humiliation, sissy training, sissification ENF To Crossdressing Humiliation Manyvids (Goddess Vanessa) 08:45
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Goddess Vanessa
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193
"jadelussuria" cock worship, double domination, gay humiliation, imposed bi, sissy training Admit It You Crave Cock Imposed Bi Manyvids (jadelussuria) 09:21
"jadelussuria" cock worship, double domination, gay humiliation, imposed bi, sissy training Admit It You Crave Cock Imposed Bi Manyvids (jadelussuria)
jadelussuria
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"jadelussuria" pov strapon, sissification, sissy sluts, sissy training, strap-on Cock Sucking Sissy Training Manyvids (jadelussuria)
jadelussuria
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229
"Iamyetti" femdom pov, gay humiliation, goddess worship, psychological domination, sfw, sissy training YOU ONLY WANT COCK Manyvids (Iamyetti) 03:04
"Iamyetti" femdom pov, gay humiliation, goddess worship, psychological domination, sfw, sissy training YOU ONLY WANT COCK Manyvids (Iamyetti)
Iamyetti
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"Goddess Vanessa" sissy training, slut training, gay, make me bi, gay masturbation instructions CUCUMBER SLUT FAG Manyvids (Goddess Vanessa) 07:46
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Goddess Vanessa
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"Tara Tainton" analmasturbation, analplay, dildofucking, masturbationinstruction, sfw, sissytraining Tara s Sissy Anal Training 4 Manyvids (Tara Tainton) 46:17
"Tara Tainton" analmasturbation, analplay, dildofucking, masturbationinstruction, sfw, sissytraining Tara s Sissy Anal Training 4 Manyvids (Tara Tainton)
Tara Tainton
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252
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Iamyetti
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"divinebabe" ass humiliation, femdom, humiliation, sissy sluts, sissy training Joi for your ass Manyvids (divinebabe) 09:01
"divinebabe" ass humiliation, femdom, humiliation, sissy sluts, sissy training Joi for your ass Manyvids (divinebabe)
divinebabe
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195
"Iamyetti" caught, humiliation, sissification, sissy sluts, sissy training BF CAUGHT WEARING PANTIES Manyvids (Iamyetti) 02:57
"Iamyetti" caught, humiliation, sissification, sissy sluts, sissy training BF CAUGHT WEARING PANTIES Manyvids (Iamyetti)
Iamyetti
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207
"LongHairLuna" bisexual, femdom, imposed bi, imposed fem, sissy sluts Encouraging My Sissy Cucks Imposed Bi BJ Manyvids (LongHairLuna) 03:48
"LongHairLuna" bisexual, femdom, imposed bi, imposed fem, sissy sluts Encouraging My Sissy Cucks Imposed Bi BJ Manyvids (LongHairLuna)
LongHairLuna
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186
"UnfriendlyBlckHottie" ebony female domination, gay, imposed bi, sissification, sissy training Pushed Into Faggotry Manyvids (UnfriendlyBlckHottie) 05:59
"UnfriendlyBlckHottie" ebony female domination, gay, imposed bi, sissification, sissy training Pushed Into Faggotry Manyvids (UnfriendlyBlckHottie)
UnfriendlyBlckHottie
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243
"Larah_Sky" femdom, feminization, sfw, sissification, sissy training Stupid Sissy Where are your panties manyvids (Larah_Sky) 04:00
"Larah_Sky" femdom, feminization, sfw, sissification, sissy training Stupid Sissy Where are your panties manyvids (Larah_Sky)
Larah_Sky
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Dressing Up My Princess MistressPetraHunter June 06, 2021 Manyvids (MistressPetraHunter) 15:36
Dressing Up My Princess MistressPetraHunter June 06, 2021 Manyvids (MistressPetraHunter)
MistressPetraHunter
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"Tara Tainton" crossdressing, femdompov, gendertransformation, sfw, sissification, sissytraining Transforming You into My Sweet Maid Manyvids (Tara Tainton) 22:21
"Tara Tainton" crossdressing, femdompov, gendertransformation, sfw, sissification, sissytraining Transforming You into My Sweet Maid Manyvids (Tara Tainton)
Tara Tainton
1
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Dance for Me Sissy MistressPetraHunter November 17, 2017 Manyvids (MistressPetraHunter) 08:04
Dance for Me Sissy MistressPetraHunter November 17, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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You ll Wear Panties Forever MistressPetraHunter January 03, 2018 Manyvids (MistressPetraHunter) 11:53
You ll Wear Panties Forever MistressPetraHunter January 03, 2018 Manyvids (MistressPetraHunter)
MistressPetraHunter
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"TheTabithaJane" strap-on, feminization, pov strapon, sissy sluts, sissy training, sfw Femme Sluts Take Strap Pounding manyvids (TheTabithaJane) 10:20
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TheTabithaJane
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356
One Week in Pink Panties MistressPetraHunter October 06, 2017 Manyvids (MistressPetraHunter) 11:23
One Week in Pink Panties MistressPetraHunter October 06, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Suck Cock for Me Cuck MistressPetraHunter May 31, 2021 Manyvids (MistressPetraHunter) 08:51
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MistressPetraHunter
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Pretty Sissy Makeover MistressPetraHunter September 21, 2019 Manyvids (MistressPetraHunter) 11:34
Pretty Sissy Makeover MistressPetraHunter September 21, 2019 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Cocksucking Lessons MistressPetraHunter December 29, 2017 Manyvids (MistressPetraHunter) 11:36
Cocksucking Lessons MistressPetraHunter December 29, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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MistressPetraHunter
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Ballerina Bitch MistressPetraHunter July 22, 2019 Manyvids (MistressPetraHunter) 09:14
Ballerina Bitch MistressPetraHunter July 22, 2019 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Sissies Only Wear Panties MistressPetraHunter December 07, 2017 Manyvids (MistressPetraHunter) 10:01
Sissies Only Wear Panties MistressPetraHunter December 07, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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"Goddess Vanessa" femdom pov, imposed bi, sissy sluts, sissy training, sissification Baguette p0p p3 rs bitch manyvids (Goddess Vanessa) 16:45
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Goddess Vanessa
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Pretty Little Bimbo MistressPetraHunter August 11, 2019 Manyvids (MistressPetraHunter) 07:48
Pretty Little Bimbo MistressPetraHunter August 11, 2019 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Cocksucking Sissy MistressPetraHunter January 16, 2018 Manyvids (MistressPetraHunter) 09:14
Cocksucking Sissy MistressPetraHunter January 16, 2018 Manyvids (MistressPetraHunter)
MistressPetraHunter
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You re a Sissy Now MistressPetraHunter May 03, 2019 Manyvids (MistressPetraHunter) 09:42
You re a Sissy Now MistressPetraHunter May 03, 2019 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Breakup Revenge MistressPetraHunter December 30, 2020 Manyvids (MistressPetraHunter) 09:32
Breakup Revenge MistressPetraHunter December 30, 2020 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Feminine Men Are Sexy MistressPetraHunter January 27, 2021 Manyvids (MistressPetraHunter) 08:29
Feminine Men Are Sexy MistressPetraHunter January 27, 2021 Manyvids (MistressPetraHunter)
MistressPetraHunter
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"claudiahon" brat girls, humiliation, humiliation task, sissy training, submissive task Humiliation task for sissy bitch Manyvids (claudiahon) 05:37
"claudiahon" brat girls, humiliation, humiliation task, sissy training, submissive task Humiliation task for sissy bitch Manyvids (claudiahon)
claudiahon
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248
"UnfriendlyBlckHottie" ebony female domination, financial domination, humiliation, interracial, sissy training Black Community white Whore manyvids (UnfriendlyBlckHottie) 05:58
"UnfriendlyBlckHottie" ebony female domination, financial domination, humiliation, interracial, sissy training Black Community white Whore manyvids (UnfriendlyBlckHottie)
UnfriendlyBlckHottie
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200
"GirlOnTop880" chastity, femdom, lace/lingerie, sissy sluts, sissy training A Sissy Slut Story 2 Cameron s Future Manyvids (GirlOnTop880) 09:43
"GirlOnTop880" chastity, femdom, lace/lingerie, sissy sluts, sissy training A Sissy Slut Story 2 Cameron s Future Manyvids (GirlOnTop880)
GirlOnTop880
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315
My Cuckold Boyfriend MistressPetraHunter July 02, 2021 Manyvids (MistressPetraHunter) 10:20
My Cuckold Boyfriend MistressPetraHunter July 02, 2021 Manyvids (MistressPetraHunter)
MistressPetraHunter
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247
"DarlingKiyomi" femdom, feminization, ruined orgasms, sissy sluts, sissy training Ruin It Sissy Slut manyvids (DarlingKiyomi) 14:23
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DarlingKiyomi
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Public Anal Play in Chastity MistressPetraHunter December 27, 2020 Manyvids (MistressPetraHunter) 09:49
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MistressPetraHunter
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Sissy Aftercare MistressPetraHunter September 11, 2020 Manyvids (MistressPetraHunter) 12:59
Sissy Aftercare MistressPetraHunter September 11, 2020 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Practice for the Real Thing MistressPetraHunter September 12, 2017 Manyvids (MistressPetraHunter) 09:43
Practice for the Real Thing MistressPetraHunter September 12, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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214
"Iamyetti" domestic discipline, french maid fetish, humiliation task, sissification, sissy training FIRST TIME SISSY DRESS UP Manyvids (Iamyetti) 21:58
"Iamyetti" domestic discipline, french maid fetish, humiliation task, sissification, sissy training FIRST TIME SISSY DRESS UP Manyvids (Iamyetti)
Iamyetti
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307
"Princess Lexi" goddess worship, pegging, sissy training, spanking, spitting Slave punishment Manyvids (Princess Lexi) 26:16
"Princess Lexi" goddess worship, pegging, sissy training, spanking, spitting Slave punishment Manyvids (Princess Lexi)
Princess Lexi
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233
My Little Cocksucker MistressPetraHunter November 08, 2017 Manyvids (MistressPetraHunter) 07:10
My Little Cocksucker MistressPetraHunter November 08, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Punished and Humiliated Sissy Slut MistressPetraHunter July 14, 2021 Manyvids (MistressPetraHunter) 08:16
Punished and Humiliated Sissy Slut MistressPetraHunter July 14, 2021 Manyvids (MistressPetraHunter)
MistressPetraHunter
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Cock Obsessed MistressPetraHunter December 14, 2017 Manyvids (MistressPetraHunter) 07:07
Cock Obsessed MistressPetraHunter December 14, 2017 Manyvids (MistressPetraHunter)
MistressPetraHunter
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220
"Goddess Vanessa" femdom, femdom pov, humiliation, sissy training, verbal humiliation Sissy training assignment 1 Manyvids (Goddess Vanessa) 05:43
"Goddess Vanessa" femdom, femdom pov, humiliation, sissy training, verbal humiliation Sissy training assignment 1 Manyvids (Goddess Vanessa)
Goddess Vanessa
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169
"evaray" femdom, female domination, sissy training, maid training, sissification Sissy Maid Trainning Manyvids (evaray) 03:29
"evaray" femdom, female domination, sissy training, maid training, sissification Sissy Maid Trainning Manyvids (evaray)
evaray
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247
They must suck each other s cocks Fetish Videos March 29, 2025 Manyvids (Fetish Videos) 12:42
They must suck each other s cocks Fetish Videos March 29, 2025 Manyvids (Fetish Videos)
Fetish Videos
1
327
"ashleyjaymes" cum countdown, cum eating instruction, pvc-vinyl, sissy sluts, slut training My Little Fuck Boy CEI JOI Cum Slut Manyvids (ashleyjaymes) 14:39
"ashleyjaymes" cum countdown, cum eating instruction, pvc-vinyl, sissy sluts, slut training My Little Fuck Boy CEI JOI Cum Slut Manyvids (ashleyjaymes)
ashleyjaymes
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