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      Madame Miriam's sissification academy part 2 - comic art  
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     2026-10-17 
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    A few more reworks of old comic art into new backgrounds and stories - moms/aunts/teachers sissifying sons. Comments welcomed please!
    ComicDT
    ComicDT's profile
    <3,557 fans>
      CarolineMessyTV exposer captions  
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     2026-10-07 
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    carolinemessyt
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      Captions - forced to be a sissy slut by mother/aunt  
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     2024-08-10 
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    Poor guys transformed into filthy sluts by their own family members
    ComicDT
    ComicDT's profile
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      Forced feminisation sissy cartoon, reworked as mom-son theme  
     17 
    High Definition
     2024-02-21 
    Free porn pics of Forced feminisation sissy cartoon, reworked as mom-son theme 1 of  picsFree porn pics of Forced feminisation sissy cartoon, reworked as mom-son theme 2 of  pics
    A classic sissification comic story, tweaked to make it more mother son themed
    ComicDT
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      Sissy school fantasy captions  
     31 
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     2021-06-25 
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    Mature women send their boys to learn how to be slutty sissies for their pleasure.
    ComicDT
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      Captions - a new smorgasbord of MILFs, sissies, aunts and moms  
     25 
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     2021-06-16 
    Free porn pics of Captions - a new smorgasbord of MILFs, sissies, aunts and moms 1 of  picsFree porn pics of Captions - a new smorgasbord of MILFs, sissies, aunts and moms 2 of  picsFree porn pics of Captions - a new smorgasbord of MILFs, sissies, aunts and moms 3 of  picsFree porn pics of Captions - a new smorgasbord of MILFs, sissies, aunts and moms 4 of  pics
    A long overdue variety pack of captions starring slutty matures and their young relatives and neighbours - comments welcomed!
    ComicDT
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      Forced feminisation/sissification by mothers/aunts - captions  
     13 
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     2020-08-17 
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    Only a truly kinky mother would force her own teenage son to cross-dress and act like a filthy cum-slut. Or an aunt, or a neighbour, maybe :)
    ComicDT
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      Crossdressers and the women who want them  
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     2020-03-04 
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    Captain-Captio
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      Minx Sissy Caption Gifs  
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     2019-12-12 
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    SissyMinxReturn's profile
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      Crossdresser gets hand job  
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     2015-11-16 
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    A few pictures of me getting wanked by my sexy mistress
    Pantiespainter
    Pantiespainter's profile
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      Latina Princess Owns, Humiliates And Cuckolds You [Daughterdom]  
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     2015-06-18 
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    Your sweet, Latina stepdaughter is so pretty and tiny and looks as if butter wouldn't melt in her mouth. But she still reduces you to her cross-dressing, cock-sucking and cuckolded Bitch in record time!...
    FantasyCaption
    FantasyCaptions1978's profile
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      Danielle gets feminized  
     39 
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     2015-01-20 
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    a_dresserch
    a_dresserch's profile
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      Sissy Gif Caps 3  
     8 
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     2013-07-22 
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    Helenssissy
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      Cute TVs  
     6 
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     2013-07-01 
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    Random internet discoveries that keep disappearing.
    Tammy_T
    Tammy_T's profile
    <85 fans>
      Girls dressing guys as girls  
     12 
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     2013-07-01 
    Free porn pics of Girls dressing guys as girls 1 of  picsFree porn pics of Girls dressing guys as girls 2 of  picsFree porn pics of Girls dressing guys as girls 3 of  picsFree porn pics of Girls dressing guys as girls 4 of  pics
    Real girls with the guys that they've just dressed up. Random online discoveries that keep disappearing.
    Tammy_T
    Tammy_T's profile
    <85 fans>
      Captioned tranny toons and art  
     58 
    High Quality
     2013-03-23 
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    Original captions on some well known sissy toons and art. All of the pictures were taken from publicly accessible collections and not lifted from the original websites.
    Captain-Captio
    Captain-Caption's profile
    <2,784 fans>
      Other people's humiliated sissy husbands  
     113 
    High Quality
     2013-01-31 
    Free porn pics of Other people's humiliated sissy husbands 1 of  picsFree porn pics of Other people's humiliated sissy husbands 2 of  picsFree porn pics of Other people's humiliated sissy husbands 3 of  picsFree porn pics of Other people's humiliated sissy husbands 4 of  pics
    Here are some photos from Imagefap and tumblr that either remind me of things I've done, or that give me ideas for things to do. Men forced to crossdress, humiliated in public, straponed or toyed...
    EvaFox
    EvaFox's profile
    <735 fans>
      Sissy captions 291-195  
     5 
    High Quality
     2012-04-14 
    Free porn pics of Sissy captions 291-195 1 of  picsFree porn pics of Sissy captions 291-195 2 of  picsFree porn pics of Sissy captions 291-195 3 of  picsFree porn pics of Sissy captions 291-195 4 of  pics
    More daydreams from an unowned sissy ... I hope you like them ... if you do like them let m know by commenting or emailing!
    obedientsissyb
    obedientsissybimbo's profile
    <1,357 fans>
      Sissy captions 286-290  
     5 
    High Quality
     2012-04-07 
    Free porn pics of Sissy captions 286-290 1 of  picsFree porn pics of Sissy captions 286-290 2 of  picsFree porn pics of Sissy captions 286-290 3 of  picsFree porn pics of Sissy captions 286-290 4 of  pics
    More daydreams from an unowned sissy - if you like them, please email or comment!
    obedientsissyb
    obedientsissybimbo's profile
    <1,357 fans>
      Sissy captions 281-285  
     5 
    High Quality
     2012-04-03 
    Free porn pics of Sissy captions 281-285 1 of  picsFree porn pics of Sissy captions 281-285 2 of  picsFree porn pics of Sissy captions 281-285 3 of  picsFree porn pics of Sissy captions 281-285 4 of  pics
    More daydreams from a sissy in need of an owner - if you like them, please comment or email! I love to hear from you!
    obedientsissyb
    obedientsissybimbo's profile
    <1,357 fans>
      Forced feminisation/Hypnosis  
     6 
    High Quality
     2011-10-25 
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    More sissy and forced feminisation captions, plus a hypnosis gif to try
    txd101
    txd101's profile
    <1,357 fans>







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