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Sissy Training - Videos - Most Viewed This Month, Page 3

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Lana Reign - Bisexual Toy Training
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Lana Reign - Bisexual Toy Training

  • 9:22
  • 11 months
  • 398 views
Embermae - Sissy Says Yes to Big Black Cocks, Sissy Training, Sissification, BBC, POV, POV Blowjob, ManyVids
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Embermae - Sissy Says Yes to Big Black Cocks, Sissy Training, Sissification, BBC, POV, POV Blowjob, ManyVids

  • 10:30
  • 1 year
  • 347 views
MissWhitneyMorgan - Vicky Vixxx Sissifies Jordan Pt1, Sissification, Sissy Training, Beta, Cross-dressing, Humiliation, ManyVids
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MissWhitneyMorgan - Vicky Vixxx Sissifies Jordan Pt1, Sissification, Sissy Training, Beta, Cross-dressing, Humiliation, ManyVids

  • 9:29
  • 1 year
  • 189 views
Beatrixlove - Train To Dress For A Man, Sissy Training, Cross-dressing, Sissy Sluts, Transformation Fantasies, Sissification, ManyVids
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Beatrixlove - Train To Dress For A Man, Sissy Training, Cross-dressing, Sissy Sluts, Transformation Fantasies, Sissification, ManyVids

  • 5:49
  • 1 year
  • 292 views
SinnSage - Panty Bitch Brian - Sinn Sage, Female Domination, Humiliation, Prison Bitch, Sissy Sluts, Sissy Training, ManyVids
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SinnSage - Panty Bitch Brian - Sinn Sage, Female Domination, Humiliation, Prison Bitch, Sissy Sluts, Sissy Training, ManyVids

  • 10:05
  • 1 year
  • 219 views
Lucy Skye - Anal Training Manual For Fags, Anal, Imposed Bi, Gay Humiliation, Femdom, Sissy Training, ManyVids
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Lucy Skye - Anal Training Manual For Fags, Anal, Imposed Bi, Gay Humiliation, Femdom, Sissy Training, ManyVids

  • 9:31
  • 1 year
  • 277 views
Lucy Skye - Michael Terry Exposed AGAIN, Blackmail Fantasy, Make me Bi, Sissification, Sissy Sluts, Sissy Training, ManyVids
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Lucy Skye - Michael Terry Exposed AGAIN, Blackmail Fantasy, Make me Bi, Sissification, Sissy Sluts, Sissy Training, ManyVids

  • 4:09
  • 1 year
  • 200 views
MavenMay - Mistress Maven Sissy Task 2, Femdom, Sissification, Sissy Sluts, Sissy Training, Brat Girls, ManyVids
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MavenMay - Mistress Maven Sissy Task 2, Femdom, Sissification, Sissy Sluts, Sissy Training, Brat Girls, ManyVids

  • 6:39
  • 1 year
  • 305 views
MavenMay - Mistress Maven Sissy Task 4, Sissy Sluts, Sissification, Sissy Training, Brat Girls, Femdom, ManyVids
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MavenMay - Mistress Maven Sissy Task 4, Sissy Sluts, Sissification, Sissy Training, Brat Girls, Femdom, ManyVids

  • 8:16
  • 1 year
  • 491 views
MsBiancaBaker - Helping My Boy, Sissy Training, Taboo, Sissy Sluts, Mommy Roleplay, Men Following Orders, ManyVids
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MsBiancaBaker - Helping My Boy, Sissy Training, Taboo, Sissy Sluts, Mommy Roleplay, Men Following Orders, ManyVids

  • 10:18
  • 1 year
  • 318 views
BuddahsPlayground - A Girl Like Me, Make me Bi, Sissy Sluts, Sissy Training, Gay Humiliation, JOI, ManyVids
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BuddahsPlayground - A Girl Like Me, Make me Bi, Sissy Sluts, Sissy Training, Gay Humiliation, JOI, ManyVids

  • 13:38
  • 1 year
  • 332 views
BuddahsPlayground - Proper Sissy Protocol, Sissy Training, Sissy Sluts, Make me Bi, Mental Domination, Femdom POV, ManyVids
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BuddahsPlayground - Proper Sissy Protocol, Sissy Training, Sissy Sluts, Make me Bi, Mental Domination, Femdom POV, ManyVids

  • 16:01
  • 1 year
  • 301 views
BuddahsPlayground - SwishSwish A Sissy Assignment, Sissification, Sissy Training, Sissy Sluts, Submissive Task, Gender Transformation, ManyVids
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BuddahsPlayground - SwishSwish A Sissy Assignment, Sissification, Sissy Training, Sissy Sluts, Submissive Task, Gender Transformation, ManyVids

  • 21:39
  • 1 year
  • 209 views
Danielle Maye XXX - Gay Gangbang At The Gym, Bisexual, Humiliation, Sissy Training, Role Play, Gangbangs, ManyVids
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Danielle Maye XXX - Gay Gangbang At The Gym, Bisexual, Humiliation, Sissy Training, Role Play, Gangbangs, ManyVids

  • 7:16
  • 1 year
  • 343 views
Danielle Maye XXX - Keith CEI, CEI, Cum Eating Instruction, Femdom, Imposed Bi, Sissy Training, ManyVids
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Danielle Maye XXX - Keith CEI, CEI, Cum Eating Instruction, Femdom, Imposed Bi, Sissy Training, ManyVids

  • 6:01
  • 1 year
  • 401 views
Danielle Maye XXX - Sissy Boy 3 Way, Sissy Sluts, Sissy Training, Cum Swallowers, Bisexual, Humiliation, ManyVids
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Danielle Maye XXX - Sissy Boy 3 Way, Sissy Sluts, Sissy Training, Cum Swallowers, Bisexual, Humiliation, ManyVids

  • 11:07
  • 1 year
  • 453 views
Danielle Maye XXX - Sissys First Fuck, Sissy Sluts, Sissy Training, Humiliation, Bisexual, Domination, ManyVids
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Danielle Maye XXX - Sissys First Fuck, Sissy Sluts, Sissy Training, Humiliation, Bisexual, Domination, ManyVids

  • 6:30
  • 1 year
  • 311 views
Danielle Maye XXX - Sissy Training Pt 2, Sissification, Sissy Sluts, Sissy Training, Humiliation, Domination, ManyVids
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Danielle Maye XXX - Sissy Training Pt 2, Sissification, Sissy Sluts, Sissy Training, Humiliation, Domination, ManyVids

  • 8:38
  • 1 year
  • 308 views
Danielle Maye XXX - Sissy Selfies, Sissy Training, Slut Training, Lace/Lingerie, ManyVids
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Danielle Maye XXX - Sissy Selfies, Sissy Training, Slut Training, Lace/Lingerie, ManyVids

  • 7:21
  • 1 year
  • 292 views
Danielle Maye XXX - Sissy Training Pt 3, Sissification, Sissy Sluts, Sissy Training, Domination, Humiliation, ManyVids
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Danielle Maye XXX - Sissy Training Pt 3, Sissification, Sissy Sluts, Sissy Training, Domination, Humiliation, ManyVids

  • 7:46
  • 1 year
  • 310 views
ItalianLace - Hot Chick With a Dick
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ItalianLace - Hot Chick With a Dick

  • 7:02
  • 11 months
  • 194 views
MissWhitneyMorgan - Vicky Vixxx Sissifies Jordan Tyler Pt2, Sissification, Sissy Sluts, Sissy Training, Femdom, Strap-On, ManyVids
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MissWhitneyMorgan - Vicky Vixxx Sissifies Jordan Tyler Pt2, Sissification, Sissy Sluts, Sissy Training, Femdom, Strap-On, ManyVids

  • 9:26
  • 1 year
  • 289 views
Lucy Skye - Panty-Wearing, Cock-Sucking Sissy, Panty Fetish, Sissy Sluts, Sissy Training, Femdom, Make me Bi, SFW, ManyVids
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Lucy Skye - Panty-Wearing, Cock-Sucking Sissy, Panty Fetish, Sissy Sluts, Sissy Training, Femdom, Make me Bi, SFW, ManyVids

  • 8:07
  • 1 year
  • 340 views
MsBiancaBaker - Making You A Pretty Sissy, Sissy Training, Sissy Sluts, Men Following Orders, Imposed Crossdressing, Sensual Domination, ManyVids
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MsBiancaBaker - Making You A Pretty Sissy, Sissy Training, Sissy Sluts, Men Following Orders, Imposed Crossdressing, Sensual Domination, ManyVids

  • 5:27
  • 1 year
  • 196 views
BuddahsPlayground - 2021 SIT Program Official Assignment #1, Sissy Training, Feminization, Gender Transformation, Imposed Crossdressing, Assignments, ManyVids
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BuddahsPlayground - 2021 SIT Program Official Assignment #1, Sissy Training, Feminization, Gender Transformation, Imposed Crossdressing, Assignments, ManyVids

  • 18:00
  • 1 year
  • 165 views
BuddahsPlayground - Do You Dare, Blackmail Fantasy, Assignments, Sissy Training, Sissy Sluts, Submissive Sluts, ManyVids
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BuddahsPlayground - Do You Dare, Blackmail Fantasy, Assignments, Sissy Training, Sissy Sluts, Submissive Sluts, ManyVids

  • 17:05
  • 1 year
  • 126 views
BuddahsPlayground - Drive Through and Name Reveal, Feminization, Sissy Training, Sissy Sluts, Assignments, Homoerotic, ManyVids
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BuddahsPlayground - Drive Through and Name Reveal, Feminization, Sissy Training, Sissy Sluts, Assignments, Homoerotic, ManyVids

  • 14:57
  • 1 year
  • 121 views
BuddahsPlayground - Sissy Blackmail, Blackmail Fantasy, Sissy Training, Imposed Crossdressing, Feminization, Submissive Task, ManyVids
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BuddahsPlayground - Sissy Blackmail, Blackmail Fantasy, Sissy Training, Imposed Crossdressing, Feminization, Submissive Task, ManyVids

  • 16:14
  • 1 year
  • 154 views
Danielle Maye XXX - Bimbo Sissy Wank, Sissy Sluts, Sissy Training, Ass Shaking, Ass Worship, Big Butts, ManyVids
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Danielle Maye XXX - Bimbo Sissy Wank, Sissy Sluts, Sissy Training, Ass Shaking, Ass Worship, Big Butts, ManyVids

  • 5:21
  • 1 year
  • 366 views
Danielle Maye XXX - Big Fucking Gay Custom, Sissy Sluts, Sissy Training, Big Toys, Humiliation, Domination, ManyVids
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Danielle Maye XXX - Big Fucking Gay Custom, Sissy Sluts, Sissy Training, Big Toys, Humiliation, Domination, ManyVids

  • 10:29
  • 1 year
  • 359 views
Danielle Maye XXX - Gay Boy, Goddess Worship, Humiliation, Domination, Sissy Training, Anal Masturbation, ManyVids
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Danielle Maye XXX - Gay Boy, Goddess Worship, Humiliation, Domination, Sissy Training, Anal Masturbation, ManyVids

  • 7:32
  • 1 year
  • 699 views
Danielle Maye XXX - Open Your Mind, Mesmerize, Mind Fuck, Bisexual, Sissy Training, ManyVids
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Danielle Maye XXX - Open Your Mind, Mesmerize, Mind Fuck, Bisexual, Sissy Training, ManyVids

  • 6:49
  • 1 year
  • 171 views
Danielle Maye XXX - Rent Boy, Sissy Training, Masturbation Instruction, Sissy Sluts, Dildos, Jerk Off Instruction, ManyVids
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Danielle Maye XXX - Rent Boy, Sissy Training, Masturbation Instruction, Sissy Sluts, Dildos, Jerk Off Instruction, ManyVids

  • 5:14
  • 1 year
  • 230 views
Danielle Maye XXX - Sissy Cum Slut, Sissy Sluts, Sissy Training, Dildo Sucking, Bisexual, Domination, ManyVids
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Danielle Maye XXX - Sissy Cum Slut, Sissy Sluts, Sissy Training, Dildo Sucking, Bisexual, Domination, ManyVids

  • 8:18
  • 1 year
  • 378 views
Danielle Maye XXX - This is part 2 of - The Fate of Jamie, Domination, Femdom, Humiliation, Goddess Worship, Sissy Training, ManyVids
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Danielle Maye XXX - This is part 2 of - The Fate of Jamie, Domination, Femdom, Humiliation, Goddess Worship, Sissy Training, ManyVids

  • 10:40
  • 1 year
  • 334 views
ItalianLace - Milk a Load Out of My Big Dick Sissy
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ItalianLace - Milk a Load Out of My Big Dick Sissy

  • 10:35
  • 11 months
  • 224 views
Embermae - BANANA VALENTINE, Sissy Training, Humiliation Task, POV Blowjob, Femdom POV, Mask Fetish, ManyVids
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Embermae - BANANA VALENTINE, Sissy Training, Humiliation Task, POV Blowjob, Femdom POV, Mask Fetish, ManyVids

  • 5:33
  • 1 year
  • 109 views
MissWhitneyMorgan - Miss Whitney Morgan Sissifies Step-Dad, Sissification, Sissy Training, Taboo, Femdom POV, Blackmail Fantasy, SFW, ManyVids
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MissWhitneyMorgan - Miss Whitney Morgan Sissifies Step-Dad, Sissification, Sissy Training, Taboo, Femdom POV, Blackmail Fantasy, SFW, ManyVids

  • 11:23
  • 1 year
  • 330 views
MissWhitneyMorgan - Olivia and Whitney Give You The Best Gift, Feminization, Sissification, Sissy Sluts, Sissy Training, Femdom POV, SFW, ManyVids
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MissWhitneyMorgan - Olivia and Whitney Give You The Best Gift, Feminization, Sissification, Sissy Sluts, Sissy Training, Femdom POV, SFW, ManyVids

  • 10:33
  • 1 year
  • 299 views
LIshalynn01 - cock ratein vidn what a sissy clit dick, Sissy Training, SPH, Teaser, ManyVids
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LIshalynn01 - cock ratein vidn what a sissy clit dick, Sissy Training, SPH, Teaser, ManyVids

  • 9:15
  • 1 year
  • 100 views
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