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    Displaying results for 'punishment' - View all videos for 'punishment'
     Gallery Name 
     Images 
     Quality   Added 
      The Sissy Pantyhose Punishment Manual.  
     24 
    High Definition
     2024-06-20 
    Free porn pics of The Sissy Pantyhose Punishment Manual. 1 of  picsFree porn pics of The Sissy Pantyhose Punishment Manual. 2 of  picsFree porn pics of The Sissy Pantyhose Punishment Manual. 3 of  picsFree porn pics of The Sissy Pantyhose Punishment Manual. 4 of  pics
    All sissies crave discipline exactly like this!
    SissyPHTights
    SissyPHTights's profile
    <465 fans>
      Chantellesissy - if you want to fuck me, message me. Im a slut  
     8 
    High Quality
     2024-06-02 
    Free porn pics of Chantellesissy - if you want to fuck me, message me. Im a slut 1 of  picsFree porn pics of Chantellesissy - if you want to fuck me, message me. Im a slut 2 of  picsFree porn pics of Chantellesissy - if you want to fuck me, message me. Im a slut 3 of  picsFree porn pics of Chantellesissy - if you want to fuck me, message me. Im a slut 4 of  pics
    Im a dirty submissive sissy faggot who wants abuse and degradation, humiliation and ridicule, hard cock, piss, bondage, punishment, and pervy treatment
    subsissyfaggot
    subsissyfaggot's profile
    <1,164 fans>
      Sissy Wears Flat Chastity Cage then Cums Everywhere  
     14 
    High Definition
     2024-04-22 
    Free porn pics of Sissy Wears Flat Chastity Cage then Cums Everywhere 1 of  picsFree porn pics of Sissy Wears Flat Chastity Cage then Cums Everywhere 2 of  picsFree porn pics of Sissy Wears Flat Chastity Cage then Cums Everywhere 3 of  picsFree porn pics of Sissy Wears Flat Chastity Cage then Cums Everywhere 4 of  pics
    Wore a flat microchastity cage for the first time. Felt so sexy that I had to take some pics in a skirt for you, then release my clitty and cum all over the floor! I couldn't control myself! (Of course I caged myself straight away afterwards and toyed...
    trtlknk
    trtlknk's profile
    <441 fans>
      A Maids Tryout Tribulations  
     20 
    High Definition
     2024-03-03 
    Free porn pics of A Maids Tryout Tribulations 1 of  picsFree porn pics of A Maids Tryout Tribulations 2 of  picsFree porn pics of A Maids Tryout Tribulations 3 of  picsFree porn pics of A Maids Tryout Tribulations 4 of  pics
    Miss Courtney is auditioning a hopeful sissy maid, who is desperate to join her household. She explains what she expects and introduces the cock zapper to reinforce her words. Mistress teaches her the basic slave positions, making sure to punish and...
    AmazingDominat
    AmazingDominatrix's profile
    <2,275 fans>
      Female politicians in charge  
     24 
    High Quality
     2024-02-27 
    Free porn pics of Female politicians in charge 1 of  picsFree porn pics of Female politicians in charge 2 of  pics
    Women are continuing to take over positions of power and authority. As female politicians are becoming the majority, they are taking the opportunity to institute laws and punishments against beta, sissy men. The need to relegate these weak men to a...
    krista024
    krista024's profile
    <2,400 fans>
      Diaper and Adult Baby Sissification Punishment  
     4 
    High Definition
     2023-08-23 
    Free porn pics of Diaper and Adult Baby Sissification Punishment 1 of  picsFree porn pics of Diaper and Adult Baby Sissification Punishment 2 of  picsFree porn pics of Diaper and Adult Baby Sissification Punishment 3 of  picsFree porn pics of Diaper and Adult Baby Sissification Punishment 4 of  pics
    sissymarky35
    sissymarky35's profile
    <963 fans>
      MY FIRST PROPER PUNISHMENT  
     17 
    High Definition
     2023-08-21 
    Free porn pics of MY  FIRST  PROPER  PUNISHMENT 1 of  picsFree porn pics of MY  FIRST  PROPER  PUNISHMENT 2 of  picsFree porn pics of MY  FIRST  PROPER  PUNISHMENT 3 of  picsFree porn pics of MY  FIRST  PROPER  PUNISHMENT 4 of  pics
    Viviannetv
    Viviannetv's profile
    <283 fans>
      5/10 - neko T, clean me  
     126 
    Low Quality
     2023-08-15 
    Free porn pics of 5/10 - neko T, clean me 1 of  picsFree porn pics of 5/10 - neko T, clean me 2 of  picsFree porn pics of 5/10 - neko T, clean me 3 of  picsFree porn pics of 5/10 - neko T, clean me 4 of  pics
    What she saw as a punishment was actually my blessing
    nekotaylor
    nekotaylor's profile
    <2,938 fans>
      Sissy Suburbia by Evthorn  
     70 
    High Definition
     2023-05-07 
    Free porn pics of Sissy Suburbia by Evthorn 1 of  picsFree porn pics of Sissy Suburbia by Evthorn 2 of  picsFree porn pics of Sissy Suburbia by Evthorn 3 of  picsFree porn pics of Sissy Suburbia by Evthorn 4 of  pics
    Wonderful drawings by Ev capturing all those moment sissies have been caught wearing their sister's panties, or in mummy's drawer. A bit of strap on punishment too. Try not to come too quickly
    Crow67
    Crow67's profile
    <548 fans>
      Queer gay sissy Sally toilet humiliation for Sir THEFORBIDDENMAN  
     17 
    Medium Quality
     2022-09-15 
    Free porn pics of Queer gay sissy Sally toilet humiliation for Sir THEFORBIDDENMAN 1 of  picsFree porn pics of Queer gay sissy Sally toilet humiliation for Sir THEFORBIDDENMAN 2 of  picsFree porn pics of Queer gay sissy Sally toilet humiliation for Sir THEFORBIDDENMAN 3 of  picsFree porn pics of Queer gay sissy Sally toilet humiliation for Sir THEFORBIDDENMAN 4 of  pics
    After splashing the Toilet while peeing even though she pees sitting down. Sissy sally is made to lick up the wee with her tongue by THEFORBIDDENMAN as punishment. Then she is forced to do crabmeat humiliation for Sir and be his sissy bath mat.
    sallypantyhose
    sallypantyhosecd's profile
    <1,409 fans>
      Sissy must leak on paper, not on floor  
     8 
    High Quality
     2022-06-26 
    Free porn pics of Sissy must leak on paper, not on floor 1 of  picsFree porn pics of Sissy must leak on paper, not on floor 2 of  picsFree porn pics of Sissy must leak on paper, not on floor 3 of  picsFree porn pics of Sissy must leak on paper, not on floor 4 of  pics
    Sir ordered Gabrielle not to be dirty pig and stop leaking on floor and do it on paper. In first pic Gabrielle shows her respect to Sir. In last one Gabrielle licks her own precum in punishment for not being able to stop the leakage.
    sissystraight6
    sissystraight691982's profile
    <2,039 fans>
      Submissive Sissy Faggot For Real Men  
     7 
    High Quality
     2022-04-02 
    Free porn pics of Submissive Sissy Faggot For Real Men 1 of  picsFree porn pics of Submissive Sissy Faggot For Real Men 2 of  picsFree porn pics of Submissive Sissy Faggot For Real Men 3 of  picsFree porn pics of Submissive Sissy Faggot For Real Men 4 of  pics
    I am a limp-wristed sissy bitch eager to serve real men. This sniveling, weak, submissive sissy is willing to serve any real man. Age, race and size not important. My name is Tom but I like to be called sissy Trish. I a 5'8 125 pounds, flat chested...
    Sissyfag10027
    Sissyfag10027's profile
    <178 fans>
      Sissy Femboys - Some Bound For Sex And Punishment  
     85 
    High Definition
     2021-12-28 
    Free porn pics of Sissy Femboys - Some Bound For Sex And Punishment 1 of  picsFree porn pics of Sissy Femboys - Some Bound For Sex And Punishment 2 of  picsFree porn pics of Sissy Femboys - Some Bound For Sex And Punishment 3 of  picsFree porn pics of Sissy Femboys - Some Bound For Sex And Punishment 4 of  pics
    tiedlegs
    tiedlegs's profile
    <3,827 fans>
      Curler Punishment  
     8 
    Medium Quality
     2021-10-22 
    Free porn pics of Curler Punishment 1 of  picsFree porn pics of Curler Punishment 2 of  picsFree porn pics of Curler Punishment 3 of  picsFree porn pics of Curler Punishment 4 of  pics
    SwitchGurl
    SwitchGurl's profile
    <1,719 fans>
      Sissy slave love expose to public waiting for punishment  
     6 
    High Quality
     2021-05-11 
    Free porn pics of Sissy slave love expose to public waiting for punishment 1 of  picsFree porn pics of Sissy slave love expose to public waiting for punishment 2 of  picsFree porn pics of Sissy slave love expose to public waiting for punishment 3 of  picsFree porn pics of Sissy slave love expose to public waiting for punishment 4 of  pics
    slavekar
    slavekar's profile
    <301 fans>
      sissy slut expose to public punishment  
     6 
    Low Quality
     2021-05-11 
    Free porn pics of sissy slut expose to public punishment 1 of  picsFree porn pics of sissy slut expose to public punishment 2 of  picsFree porn pics of sissy slut expose to public punishment 3 of  picsFree porn pics of sissy slut expose to public punishment 4 of  pics
    slavekar
    slavekar's profile
    <301 fans>
      sissy expose humiliation punishment videos  
     1 
    Low Quality
     2021-05-11 
    Free porn pics of sissy expose humiliation punishment videos 1 of  pics
    slavekar
    slavekar's profile
    <301 fans>
      crossdresser punishment 1  
     123 
    High Quality
     2021-01-12 
    Free porn pics of crossdresser punishment 1 1 of  picsFree porn pics of crossdresser punishment 1 2 of  picsFree porn pics of crossdresser punishment 1 3 of  picsFree porn pics of crossdresser punishment 1 4 of  pics
    crossdresser slave punishment
    gockel1
    gockel1's profile
    <458 fans>
      crossdresser punishment  
     535 
    High Quality
     2021-01-11 
    Free porn pics of crossdresser punishment 1 of  picsFree porn pics of crossdresser punishment 2 of  picsFree porn pics of crossdresser punishment 3 of  picsFree porn pics of crossdresser punishment 4 of  pics
    crossdresser punishment
    gockel1
    gockel1's profile
    <458 fans>
      Training Her Sissy  
     16 
    High Quality
     2020-11-18 
    Free porn pics of Training Her Sissy 1 of  picsFree porn pics of Training Her Sissy 2 of  picsFree porn pics of Training Her Sissy 3 of  picsFree porn pics of Training Her Sissy 4 of  pics
    Mistress Lorraine is keeping a sharp eye on her sissy in training, Sharon, watching her on the webcam as she is doing her chores, making sure she is doing as instructed. After berating her slowness, Mistress orders her over to the lounge for suitable...
    AmazingDominat
    AmazingDominatrix's profile
    <2,275 fans>
      Crossdresser punishment  
     98 
    High Quality
     2019-10-21 
    Free porn pics of Crossdresser punishment 1 of  picsFree porn pics of Crossdresser punishment 2 of  picsFree porn pics of Crossdresser punishment 3 of  picsFree porn pics of Crossdresser punishment 4 of  pics
    crossdresser slave bitch punished ass
    gockel1
    gockel1's profile
    <458 fans>
      Sissy wearing electo punishment chastity device  
     5 
    High Definition
     2018-09-23 
    Free porn pics of Sissy wearing electo punishment chastity device 1 of  picsFree porn pics of Sissy wearing electo punishment chastity device 2 of  picsFree porn pics of Sissy wearing electo punishment chastity device 3 of  picsFree porn pics of Sissy wearing electo punishment chastity device 4 of  pics
    Me wearing my sissy clothes for doing household chores. Im wearing an electro shock chastity cage to keep me motivated and humble. Write me if you would like to control the shock unit to punish or motivate me.
    scentofrubber
    scentofrubber's profile
    <1,108 fans>
      SissyKristina - Blonde Bimbo is back  
     15 
    High Definition
     2018-09-11 
    Free porn pics of SissyKristina - Blonde Bimbo is back 1 of  picsFree porn pics of SissyKristina - Blonde Bimbo is back 2 of  picsFree porn pics of SissyKristina - Blonde Bimbo is back 3 of  picsFree porn pics of SissyKristina - Blonde Bimbo is back 4 of  pics
    Dumb bitch is back from hiding after a few months. This stupid whore was ordered to make a new set as punishment so I will be posting that soon too! I want some tributes of this whores pics with her mouth open. Email them to me so I can post them and...
    MasterOfSissyB
    MasterOfSissyBitches's profile
    <952 fans>
      Sissy Devine Duvet Punishment  
     15 
    High Definition
     2018-01-27 
    Free porn pics of Sissy Devine Duvet Punishment 1 of  picsFree porn pics of Sissy Devine Duvet Punishment 2 of  picsFree porn pics of Sissy Devine Duvet Punishment 3 of  picsFree porn pics of Sissy Devine Duvet Punishment 4 of  pics
    My sissy MILF bimbo fuckdoll Devine made 1 small mistake but had to be punished. Worthless slut making those sissy ass cheeks glow nice and red.
    Dom4sissys
    Dom4sissys's profile
    <520 fans>
      Sissy Bondage  
     10 
    High Definition
     2017-04-24 
    Free porn pics of Sissy Bondage 1 of  picsFree porn pics of Sissy Bondage 2 of  picsFree porn pics of Sissy Bondage 3 of  picsFree porn pics of Sissy Bondage 4 of  pics
    Sissy has been Bound and gagged tightly as a punishment for poor behavior.
    Terrajune
    Terrajune's profile
    <42 fans>


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