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     Gallery Name 
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     Quality   Added 
      Brainwashing Myself - Sissy Lifestyle Appreciation  
     60 
    High Quality
     2023-12-06 
    Free porn pics of Brainwashing Myself - Sissy Lifestyle Appreciation 1 of  picsFree porn pics of Brainwashing Myself - Sissy Lifestyle Appreciation 2 of  picsFree porn pics of Brainwashing Myself - Sissy Lifestyle Appreciation 3 of  picsFree porn pics of Brainwashing Myself - Sissy Lifestyle Appreciation 4 of  pics
    I embrace, glorify and appreciate the Sissy Lifestyle! My Life Aim is pictured in the first of all this wonderful images: on all fours, barely clothed cleaning for my Daddy while being always ready for him to drain his balls or bladder just to make him...
    wurster
    wurster's profile
    <1,576 fans>
      Don't Piss A Brother Off Sissy - Interracial Sissy Captions  
     24 
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     2023-11-06 
    Free porn pics of Don't Piss A Brother Off Sissy - Interracial Sissy Captions 1 of  picsFree porn pics of Don't Piss A Brother Off Sissy - Interracial Sissy Captions 2 of  pics
    Please help support my captions creating by checking out my full length forced feminization and interracial sissy humiliation e-books. They take the whole themes WAY further than a single picture could ever hope to. They’re available exclusively from...
    Candy_Runt
    Candy_Runt's profile
    <3,665 fans>
      Sissy story: A visit from a friend  
     16 
    Low Quality
     2023-08-19 
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    Minding your own business at home, wearing comfortable and sexy clothes when all of a sudden someone knocks on the door, and you open it to see an old friend... Who knows what he'll do to you
    AvaButtlover
    AvaButtlover's profile
    <130 fans>
      Trans/Sissy Brothers 'n Sisters Captions #3  
     26 
    High Quality
     2023-07-26 
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    nSîblinglove is one of the hottest things, right? And it gets turned up to 11 when there are sissies and feminization involved. Taboo and fun! Leave many yummy comments and let me know if I should do more!
    Elliie
    Elliie's profile
    <626 fans>
      Sissy Bitches Get Bulled and Blacked - Humiliation Captions  
     24 
    High Quality
     2023-07-25 
    Free porn pics of Sissy Bitches Get Bulled and Blacked - Humiliation Captions 1 of  picsFree porn pics of Sissy Bitches Get Bulled and Blacked - Humiliation Captions 2 of  pics
    Please help support my captions creating by checking out my full length forced feminization and sissy humiliation e-books. They take the whole themes WAY further than a single picture could ever hope to. They’re available exclusively from the...
    Candy_Runt
    Candy_Runt's profile
    <3,665 fans>
      Trans/Sissy Brothers 'n Sisters Captions #2  
     19 
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     2023-07-19 
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    Sîblinglove is one of the hottest things, right? And it gets turned up to 11 when there are sissies and feminization involved. Taboo and fun! Leave many yummy comments and let me know if I should do more!
    Elliie
    Elliie's profile
    <626 fans>
      Tabby Myers  
     36 
    High Quality
     2023-06-07 
    Free porn pics of Tabby Myers 1 of  picsFree porn pics of Tabby Myers 2 of  picsFree porn pics of Tabby Myers 3 of  picsFree porn pics of Tabby Myers 4 of  pics
    This little sissy homo loves big black cock...LOL!...I'll bet her slut mommy would be so proud of her right now!!
    MrMan_JM
    MrMan_JM's profile
    <382 fans>
      Cyberpunk Sissy  
     10 
    High Definition
     2023-05-04 
    Free porn pics of Cyberpunk Sissy 1 of  picsFree porn pics of Cyberpunk Sissy 2 of  pics
    A Sissy has to be careful in Night City, she never knows when one wrong step might lead to her becoming a permanent cyber-slut! Generated with Stable Diffusion, primarily the PFG model and a custom chastity cage lora.
    SashaSoreCapti
    SashaSoreCaptions's profile
    <2,371 fans>
      Enslaved on Sissy Island  
     15 
    High Definition
     2023-03-12 
    Free porn pics of Enslaved on Sissy Island 1 of  picsFree porn pics of Enslaved on Sissy Island 2 of  picsFree porn pics of Enslaved on Sissy Island 3 of  picsFree porn pics of Enslaved on Sissy Island 4 of  pics
    A short story about being tricked into Sissy Slavery on a tropical island by the devious SHA. Images generated from Stable Diff using PFG model and various lora embeddings
    SashaSoreCapti
    SashaSoreCaptions's profile
    <2,371 fans>
      MLG / Sissy captions 49 - Interracial Sissy Whores  
     15 
    High Definition
     2023-02-24 
    Free porn pics of  MLG / Sissy captions 49 - Interracial Sissy Whores 1 of  picsFree porn pics of  MLG / Sissy captions 49 - Interracial Sissy Whores 2 of  pics
    This was requested via an anonymous email so I thought I'd give it a go. It's kinda timid compared to the voluntary disposal clinic stuff I see elsewhere on IF. If that's what you're looking for then this ain't it. Attire while writing these was femboi...
    Orokana_Shojo
    Orokana_Shojo's profile
    <845 fans>
      MLG / Sissy captions 42 - The AI-led Sissy Future  
     15 
    High Definition
     2023-02-06 
    Free porn pics of MLG / Sissy captions 42 - The AI-led Sissy Future 1 of  picsFree porn pics of MLG / Sissy captions 42 - The AI-led Sissy Future 2 of  picsFree porn pics of MLG / Sissy captions 42 - The AI-led Sissy Future 3 of  picsFree porn pics of MLG / Sissy captions 42 - The AI-led Sissy Future 4 of  pics
    As I guessed in the header for gallery 40 - I spent all of January in a mini-cage. And in the last week I've been able to consistently cum hands-free on cam for my Mistress. Both a blessing and a curse really. She was the one to suggest I look only at...
    Orokana_Shojo
    Orokana_Shojo's profile
    <845 fans>
      Family taboo.   
     31 
    Medium Quality
     2022-03-19 
    Free porn pics of Family taboo.  1 of  picsFree porn pics of Family taboo.  2 of  picsFree porn pics of Family taboo.  3 of  picsFree porn pics of Family taboo.  4 of  pics
    Some family related captions i have been making in my free time, might add more if get in the mood to create more. :)
    Natasha_sissyQ
    Natasha_sissyQueen's profile
    <98 fans>
      El-E's Inimitable Transformation Gallery  
     37 
    Low Quality
     2021-11-22 
    Free porn pics of El-E's Inimitable Transformation Gallery 1 of  picsFree porn pics of El-E's Inimitable Transformation Gallery 2 of  picsFree porn pics of El-E's Inimitable Transformation Gallery 3 of  picsFree porn pics of El-E's Inimitable Transformation Gallery 4 of  pics
    El-E
    El-E's profile
    <440 fans>
      Pimped Sissy Whore  
     2 
    High Quality
     2021-09-28 
    Free porn pics of Pimped Sissy Whore 1 of  picsFree porn pics of Pimped Sissy Whore 2 of  pics
    Her ruin was now complete. It started as just a bit of fun, some dress ups and occasional chat with some strangers online. But her fun had now turned into a nightmare after putting her trust in the wrong person. Tyrone, a black dominant she met online...
    under_thumbed
    under_thumbed's profile
    <13 fans>
      A Deal with the Devils: A Sissy Venice Story  
     5 
    High Definition
     2021-08-03 
    Free porn pics of A Deal with the Devils: A Sissy Venice Story 1 of  picsFree porn pics of A Deal with the Devils: A Sissy Venice Story 2 of  picsFree porn pics of A Deal with the Devils: A Sissy Venice Story 3 of  picsFree porn pics of A Deal with the Devils: A Sissy Venice Story 4 of  pics
    TRIGGER WARNING: Captivity, Rape, Death. This exists solely as a work of fantasy. Any actual violation of consent in real life is detestable. ///////// Supervisor's Note: What a pity. Investigator 57C would have relished the opportunity to have broken...
    masterroboto
    masterroboto's profile
    <226 fans>
      Sissy, Femdom, Chastity, Betaboy Captionmix  
     38 
    High Quality
     2021-06-28 
    Free porn pics of Sissy, Femdom, Chastity, Betaboy Captionmix 1 of  picsFree porn pics of Sissy, Femdom, Chastity, Betaboy Captionmix 2 of  picsFree porn pics of Sissy, Femdom, Chastity, Betaboy Captionmix 3 of  picsFree porn pics of Sissy, Femdom, Chastity, Betaboy Captionmix 4 of  pics
    geiler Mix von allem was dabei! gerne eure geilen Kommentare!!
    19Happyboy80
    19Happyboy80's profile
    <1,001 fans>
      Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 2  
     166 
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     2021-06-15 
    Free porn pics of  Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 2 1 of  picsFree porn pics of  Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 2 2 of  picsFree porn pics of  Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 2 3 of  picsFree porn pics of  Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 2 4 of  pics
    geiler Mix von allem was dabei! gerne eure geilen Kommentare!!
    19Happyboy80
    19Happyboy80's profile
    <1,001 fans>
      Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix  
     162 
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     2021-06-04 
    Free porn pics of Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 1 of  picsFree porn pics of Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 2 of  picsFree porn pics of Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 3 of  picsFree porn pics of Sissy, Cuckold, Femdom, Chastity, Betaboy Caption Mix 4 of  pics
    geiler Mix von allem was dabei! gerne eure geilen Kommentare!!
    19Happyboy80
    19Happyboy80's profile
    <1,001 fans>
      Stop Ejac 40  
     47 
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     2021-03-14 
    Free porn pics of Stop Ejac 40 1 of  picsFree porn pics of Stop Ejac 40 2 of  picsFree porn pics of Stop Ejac 40 3 of  picsFree porn pics of Stop Ejac 40 4 of  pics
    caption french frustration chaste chasteté branleur jus soumis allumeuse petit culotte pantie mouille teen mature humiliation cfnm rules interdit ejaculation caption french frustration chaste chastity juice submitted handjob tease little wet panties...
    crossdress06
    crossdress06's profile
    <3,334 fans>
      10 Stages Of A Sissy  
     10 
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     2020-06-17 
    Free porn pics of 10 Stages Of A Sissy 1 of  picsFree porn pics of 10 Stages Of A Sissy 2 of  picsFree porn pics of 10 Stages Of A Sissy 3 of  picsFree porn pics of 10 Stages Of A Sissy 4 of  pics
    pretty sissy, if she was a friend of mine I would try exploring with her if she let me. The storyline is hot. ________________________I REALLY WANT TO MEET PRETTY GIRLS AN SEXY LADIES WHO ARE ACTUALLY INTO THE LIFESTYLE OF SISSIFYING AN FEMINIZING GUYS...
    ShyLonelyVirgi
    ShyLonelyVirgin's profile
    <930 fans>
      SISSY CAPTIONS 22: PROSTITUTION  
     20 
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     2020-05-28 
    Free porn pics of SISSY CAPTIONS 22: PROSTITUTION 1 of  picsFree porn pics of SISSY CAPTIONS 22: PROSTITUTION 2 of  picsFree porn pics of SISSY CAPTIONS 22: PROSTITUTION 3 of  picsFree porn pics of SISSY CAPTIONS 22: PROSTITUTION 4 of  pics
    Feminizing a sissy cuckold properly is a very expensive process, and most alphas are rightly quite unwilling to spend their own hard-earned cash on it. Luckily, even though sissies lack any marketable skills or desirable qualities outside of being...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,333 fans>
      ASIAN REHABILITATION: ASIAN JOB PROSPECTS  
     24 
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     2020-05-07 
    Free porn pics of ASIAN REHABILITATION: ASIAN JOB PROSPECTS 1 of  picsFree porn pics of ASIAN REHABILITATION: ASIAN JOB PROSPECTS 2 of  picsFree porn pics of ASIAN REHABILITATION: ASIAN JOB PROSPECTS 3 of  picsFree porn pics of ASIAN REHABILITATION: ASIAN JOB PROSPECTS 4 of  pics
    In this installment of the Asian Rehabilitation series, we get to see how the Asian race is forced to earn enough money to survive in a post-ICAR world. These bimboified sluts and feminized sissies exist solely to please the superior whites, blacks and...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,333 fans>
      Sissy Camp Bro to Hoe  
     7 
    High Quality
     2020-04-09 
    Free porn pics of Sissy Camp Bro to Hoe 1 of  picsFree porn pics of Sissy Camp Bro to Hoe 2 of  picsFree porn pics of Sissy Camp Bro to Hoe 3 of  picsFree porn pics of Sissy Camp Bro to Hoe 4 of  pics
    Sissy camp lets guests abuse the staff, but turns the tables turning guests into submissive sissies.
    PowerExchangeS
    PowerExchangeSlut's profile
    <524 fans>
      Underground Swap Clinic - Choose Your New Life, At Your Own Risk  
     16 
    High Quality
     2019-09-19 
    Free porn pics of Underground Swap Clinic - Choose Your New Life, At Your Own Risk 1 of  picsFree porn pics of Underground Swap Clinic - Choose Your New Life, At Your Own Risk 2 of  picsFree porn pics of Underground Swap Clinic - Choose Your New Life, At Your Own Risk 3 of  picsFree porn pics of Underground Swap Clinic - Choose Your New Life, At Your Own Risk 4 of  pics
    After much consideration, you've decided that you simply cannot continue your life as-is. You want to body swap with a pretty woman. However, the prices at the Swap Clinic are simply beyond your budget. You've heard rumors, though, of an "Underground...
    rickbennett
    rickbennett's profile
    <1,567 fans>
      Sissy story - Caught by my Dad's friend +taboo+fake shemale pics  
     19 
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     2019-06-21 
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    This is a long one, but I got really horny writing it. Comment with parts you like.
    mgojbcherry
    mgojbcherry's profile
    <1,249 fans>


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