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     Gallery Name 
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      Sissy and Feminization Captions 34: Feminized by Family 8   
     20 
    High Quality
     2024-03-11 
    Free porn pics of  Sissy and Feminization Captions 34: Feminized by Family 8  1 of  picsFree porn pics of  Sissy and Feminization Captions 34: Feminized by Family 8  2 of  picsFree porn pics of  Sissy and Feminization Captions 34: Feminized by Family 8  3 of  picsFree porn pics of  Sissy and Feminization Captions 34: Feminized by Family 8  4 of  pics
    Meek males turn tranny after their family's fierce females forcibly feminize them into submissive shemales.
    ViennaSheraton
    ViennaSheraton's profile
    <1,078 fans>
      The Great Shift Experiences - 15  
     26 
    High Quality
     2023-11-06 
    Free porn pics of The Great Shift Experiences - 15 1 of  picsFree porn pics of The Great Shift Experiences - 15 2 of  picsFree porn pics of The Great Shift Experiences - 15 3 of  picsFree porn pics of The Great Shift Experiences - 15 4 of  pics
    The Great Shift - On a typical day like any other, 95% of the world's population suddenly found themselves shifted into the bodies of others. Men who became women seemed to have it particularly rough...long hair, bras, panties, periods, pregnancy...all...
    rickbennett
    rickbennett's profile
    <1,581 fans>
      Magic Transformation - Costume Party  
     8 
    High Definition
     2023-10-30 
    Free porn pics of Magic Transformation - Costume Party 1 of  picsFree porn pics of Magic Transformation - Costume Party 2 of  picsFree porn pics of Magic Transformation - Costume Party 3 of  picsFree porn pics of Magic Transformation - Costume Party 4 of  pics
    Magical transformation story where a group of friends at a Halloween party is cursed by a witch and needs to...get creative in order to switch back! Halloween, costume, harley quinn, joker, cleavage, khal drogo, daenarys, poison ivy, thor, loki, gay,...
    rickbennett
    rickbennett's profile
    <1,581 fans>
      Bad Bully Captions 4 - Sissified by Bully  
     18 
    High Quality
     2023-10-28 
    Free porn pics of Bad Bully Captions 4 - Sissified by Bully 1 of  picsFree porn pics of Bad Bully Captions 4 - Sissified by Bully 2 of  picsFree porn pics of Bad Bully Captions 4 - Sissified by Bully 3 of  picsFree porn pics of Bad Bully Captions 4 - Sissified by Bully 4 of  pics
    Even more mean-spirited bully captions, beta boys bested by bullies, their sexuality subverted to sissy status as the weakling wimps are forcibly feminized into tormented trannies.
    ViennaSheraton
    ViennaSheraton's profile
    <1,078 fans>
      My Mistress, my Pimp  
     24 
    High Quality
     2023-10-06 
    Free porn pics of My Mistress, my Pimp 1 of  picsFree porn pics of My Mistress, my Pimp 2 of  pics
    Miss Stacey trained me a lot. I thought it was for her own pleasure but it seems she was planning something else... (you can see the original pictures in JoeBacon's gallery "Young Pretty Horny Trannies_Gurls's_Sissies_Traps")
    sissystraight6
    sissystraight691982's profile
    <2,037 fans>
      SISSY CAPTIONS 84: HELPLESS SISSY PETS  
     8 
    High Quality
     2023-09-23 
    Free porn pics of SISSY CAPTIONS 84: HELPLESS SISSY PETS 1 of  picsFree porn pics of SISSY CAPTIONS 84: HELPLESS SISSY PETS 2 of  pics
    o-okay, so, yes, a helpless little fucktoy for real men IS th-the, aheh, gold standard for sissies... but these little pets are EXTRA helpless n pathetic n slutty, because they really just can't help themselves!! whether it's hypnosis, o-or a chastity...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,358 fans>
      (Attention scat) Devote Sissys lieben M�nnerschokolade / Submiss  
     17 
    High Definition
     2023-09-15 
    Free porn pics of (Attention scat) Devote Sissys lieben M�nnerschokolade / Submiss 1 of  picsFree porn pics of (Attention scat) Devote Sissys lieben M�nnerschokolade / Submiss 2 of  picsFree porn pics of (Attention scat) Devote Sissys lieben M�nnerschokolade / Submiss 3 of  picsFree porn pics of (Attention scat) Devote Sissys lieben M�nnerschokolade / Submiss 4 of  pics
    Kleineboystute
    Kleineboystute's profile
    <590 fans>
      Don't fuck the Maid! (2)  
     24 
    High Quality
     2023-08-16 
    Free porn pics of Don't fuck the Maid! (2) 1 of  picsFree porn pics of Don't fuck the Maid! (2) 2 of  picsFree porn pics of Don't fuck the Maid! (2) 3 of  picsFree porn pics of Don't fuck the Maid! (2) 4 of  pics
    Now Miss Stacey tell us how was the beginning of this story... and how it continues. (thanks Miss Stacey for your ideas!) (you can see the original pictures in several galleries such us ViennaSheraton's "Sissy Maid and Feminization Captions",...
    sissystraight6
    sissystraight691982's profile
    <2,037 fans>
      Don't fuck the Maid!  
     24 
    High Quality
     2023-08-14 
    Free porn pics of Don't fuck the Maid! 1 of  picsFree porn pics of Don't fuck the Maid! 2 of  picsFree porn pics of Don't fuck the Maid! 3 of  picsFree porn pics of Don't fuck the Maid! 4 of  pics
    I always love adrenaline so one day when my wife Stacey was still at work, i arrived early and fucked the maid... well, this gallery is about what happened after Stacey found out what I did... (you can see the original pictures in lot of galleries, for...
    sissystraight6
    sissystraight691982's profile
    <2,037 fans>
      How my Mistress "Maid" me...  
     24 
    High Quality
     2023-08-07 
    Free porn pics of How my Mistress "Maid" me... 1 of  picsFree porn pics of How my Mistress "Maid" me... 2 of  pics
    My wife decided that I should be her maid. I clearly objected but in the end she got her way... these are my days as a servant.(you can see the original pictures in Custombike76's gallery "hazel tucker" and in ViennaSheraton's "Sissy Maid and...
    sissystraight6
    sissystraight691982's profile
    <2,037 fans>
      Sissy and Feminization Captions 24: Feminized by Family 2  
     20 
    Medium Quality
     2023-05-29 
    Free porn pics of Sissy and Feminization Captions 24: Feminized by Family 2 1 of  picsFree porn pics of Sissy and Feminization Captions 24: Feminized by Family 2 2 of  picsFree porn pics of Sissy and Feminization Captions 24: Feminized by Family 2 3 of  picsFree porn pics of Sissy and Feminization Captions 24: Feminized by Family 2 4 of  pics
    Sissy whitebois get feminized by their black step family members. There ain't no turning back the clock once tranny whitebois taste black cock!
    ViennaSheraton
    ViennaSheraton's profile
    <1,078 fans>
      How to train your Sissy Slave  
     24 
    High Quality
     2023-05-24 
    Free porn pics of How to train your Sissy Slave 1 of  picsFree porn pics of How to train your Sissy Slave 2 of  picsFree porn pics of How to train your Sissy Slave 3 of  picsFree porn pics of How to train your Sissy Slave 4 of  pics
    This is Rhiannon, my new acquisition. She needs to be trained, so I think I'll share my experience with you to do a public service: Some people don't know how to train a sissy slave, so I hope you can use this gallery as a tutorial. (you can see the...
    sissystraight6
    sissystraight691982's profile
    <2,037 fans>
      MLG / Sissy captions 45 - Adult Baby Cucks III   
     15 
    High Definition
     2023-02-10 
    Free porn pics of  MLG / Sissy captions 45 - Adult Baby Cucks III  1 of  picsFree porn pics of  MLG / Sissy captions 45 - Adult Baby Cucks III  2 of  picsFree porn pics of  MLG / Sissy captions 45 - Adult Baby Cucks III  3 of  picsFree porn pics of  MLG / Sissy captions 45 - Adult Baby Cucks III  4 of  pics
    A debt of gratitude to user JennyMaid who uploaded a bevy of galleries yesterday and saved me the legwork of finding images. While writing these I wore a diaper, padded plastic cover and fuschia sissy-frilled shorties and top set that probably came...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      MLG / Sissy captions 43 - Stupid Sissy Sluts IV  
     15 
    High Definition
     2023-02-09 
    Free porn pics of  MLG / Sissy captions 43 - Stupid Sissy Sluts IV 1 of  picsFree porn pics of  MLG / Sissy captions 43 - Stupid Sissy Sluts IV 2 of  picsFree porn pics of  MLG / Sissy captions 43 - Stupid Sissy Sluts IV 3 of  picsFree porn pics of  MLG / Sissy captions 43 - Stupid Sissy Sluts IV 4 of  pics
    Those stupid sissy sluts, they just don't learn. They deserve everything cumming their way. No gimmicks this time, just back to the bread and butter you expect from me. For these I was wearing a body lingerie harness under skinny femme jeans and a...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      MLG / Sissy captions 37 - Sissy Femboi Sluts II  
     15 
    High Definition
     2022-10-30 
    Free porn pics of MLG / Sissy captions 37 - Sissy Femboi Sluts II 1 of  picsFree porn pics of MLG / Sissy captions 37 - Sissy Femboi Sluts II 2 of  picsFree porn pics of MLG / Sissy captions 37 - Sissy Femboi Sluts II 3 of  picsFree porn pics of MLG / Sissy captions 37 - Sissy Femboi Sluts II 4 of  pics
    A Sunday gallery, and probably tamer than my average output. I dunno, maybe I'm still a little blissed from my weekend activities. Oh, and I'm free of chastity now and for the forseeable - I guess I failed Locktober. Oh well. Outfit for writing these...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      SISSY CAPTIONS 60: TALK OF THE TOWN III  
     9 
    High Definition
     2022-09-17 
    Free porn pics of SISSY CAPTIONS 60: TALK OF THE TOWN III 1 of  picsFree porn pics of SISSY CAPTIONS 60: TALK OF THE TOWN III 2 of  picsFree porn pics of SISSY CAPTIONS 60: TALK OF THE TOWN III 3 of  picsFree porn pics of SISSY CAPTIONS 60: TALK OF THE TOWN III 4 of  pics
    it's been a while since i-i did one of these! these lil sissies haven't just been feminized... th-their transformation's progressed to the point that it's impossible to hide, and the people around them are very much discussing it!! hnnng, h-how...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,358 fans>
      MLG / Sissy captions 32 - Adult Baby Cucks II  
     15 
    High Definition
     2022-09-07 
    Free porn pics of MLG / Sissy captions 32 - Adult Baby Cucks II 1 of  picsFree porn pics of MLG / Sissy captions 32 - Adult Baby Cucks II 2 of  picsFree porn pics of MLG / Sissy captions 32 - Adult Baby Cucks II 3 of  picsFree porn pics of MLG / Sissy captions 32 - Adult Baby Cucks II 4 of  pics
    A lot of fond memories of past experiences mixed with fantasies and where the images led me went into these, and if it hadn't been for a random search for "goth abdl" I wouldn't have discovered lilsuccubunnie for which I thank the universe. Caption 13...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      Sissy Maid and Feminization Captions: Introducing RE-MAID  
     32 
    Medium Quality
     2022-09-07 
    Free porn pics of Sissy Maid and Feminization Captions: Introducing RE-MAID 1 of  picsFree porn pics of Sissy Maid and Feminization Captions: Introducing RE-MAID 2 of  picsFree porn pics of Sissy Maid and Feminization Captions: Introducing RE-MAID 3 of  picsFree porn pics of Sissy Maid and Feminization Captions: Introducing RE-MAID 4 of  pics
    RE-MAID, the latest innovation to fix conflicting generations. Turn older pissy men into young sissy maids!
    ViennaSheraton
    ViennaSheraton's profile
    <1,078 fans>
      MLG / Sissy captions 30 - Bimbo Whores  
     15 
    High Definition
     2022-09-02 
    Free porn pics of  MLG / Sissy captions 30 - Bimbo Whores 1 of  picsFree porn pics of  MLG / Sissy captions 30 - Bimbo Whores 2 of  picsFree porn pics of  MLG / Sissy captions 30 - Bimbo Whores 3 of  picsFree porn pics of  MLG / Sissy captions 30 - Bimbo Whores 4 of  pics
    Bimbos, Sissy Whores and Adult Babies, oh my. A lot of heavy coercion in these, and I speak from personal experience when I say guys really talk down to you when you're an obvious bleached blonde - it can be very frustrating. Apologies for using the...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      MLG / Sissy captions 24 - Soft Power  
     15 
    High Definition
     2022-08-18 
    Free porn pics of MLG / Sissy captions 24 - Soft Power 1 of  picsFree porn pics of MLG / Sissy captions 24 - Soft Power 2 of  picsFree porn pics of MLG / Sissy captions 24 - Soft Power 3 of  picsFree porn pics of MLG / Sissy captions 24 - Soft Power 4 of  pics
    A lighter set of caps this time, more around persuasion and predicament than previous galleries. For my confessional cap at the end I seem to have gotten deep, so if you've had your daily dose of shower thoughts already feel free to skip it. For this...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      MLG / Sissy captions 19 - Adult Baby Cucks  
     15 
    High Definition
     2022-08-15 
    Free porn pics of MLG / Sissy captions 19 - Adult Baby Cucks 1 of  picsFree porn pics of MLG / Sissy captions 19 - Adult Baby Cucks 2 of  picsFree porn pics of MLG / Sissy captions 19 - Adult Baby Cucks 3 of  picsFree porn pics of MLG / Sissy captions 19 - Adult Baby Cucks 4 of  pics
    Nothing but pink baby cuck caps, so to hew close to the theme I wore an outfit from Leanne's Pretty Dresses whilst writing them. That final caption feels like my most humiliating confession so far.
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      MLG / Sissy captions 10 - Stupid Sissy Slut  
     15 
    High Definition
     2022-07-28 
    Free porn pics of  MLG / Sissy captions 10 - Stupid Sissy Slut 1 of  picsFree porn pics of  MLG / Sissy captions 10 - Stupid Sissy Slut 2 of  picsFree porn pics of  MLG / Sissy captions 10 - Stupid Sissy Slut 3 of  picsFree porn pics of  MLG / Sissy captions 10 - Stupid Sissy Slut 4 of  pics
    Been a while but the skills are hopefully still there. Higher rez than previous efforts and if anyone leaves a comment requesting it I can uprez the older galleries. As is tradition I tried to set the right mood by wearing something appropriate to the...
    Orokana_Shojo
    Orokana_Shojo's profile
    <848 fans>
      SISSY CAPTIONS 55: IN THE OFFICE   
     10 
    Medium Quality
     2022-07-10 
    Free porn pics of SISSY CAPTIONS 55: IN THE OFFICE  1 of  picsFree porn pics of SISSY CAPTIONS 55: IN THE OFFICE  2 of  picsFree porn pics of SISSY CAPTIONS 55: IN THE OFFICE  3 of  picsFree porn pics of SISSY CAPTIONS 55: IN THE OFFICE  4 of  pics
    l-life in the workplace c-can be HARD f-for a weak-willed, e-easily feminized c-closeted sissy slut!! c-constantly having to dodge big, b-burly alphas... g-getting forced to u-undergo humiliating s-surgeries a-and s-sissifying treatments by a-a SUPER...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,358 fans>
      Jeannas Transformation Adventures 09  
     85 
    High Quality
     2022-04-25 
    Free porn pics of Jeannas Transformation Adventures 09 1 of  picsFree porn pics of Jeannas Transformation Adventures 09 2 of  picsFree porn pics of Jeannas Transformation Adventures 09 3 of  picsFree porn pics of Jeannas Transformation Adventures 09 4 of  pics
    Hapless males who find themselves forcibly transformed into the feminine life by family, friends, or perhaps just by random chance by means of threat, hypnosis, or circumstance. What would you do if you found yourself in their high heels?
    jeannaz
    jeannaz's profile
    <463 fans>
      Jeannas transformation Adventures 07  
     398 
    Medium Quality
     2022-02-20 
    Free porn pics of Jeannas transformation Adventures 07 1 of  picsFree porn pics of Jeannas transformation Adventures 07 2 of  picsFree porn pics of Jeannas transformation Adventures 07 3 of  picsFree porn pics of Jeannas transformation Adventures 07 4 of  pics
    Hapless males who find themselves forcibly transformed into the feminine life by family, friends, or perhaps just by random chance by means of threat, hypnosis, or circumstance. What would you do if you found yourself in their high heels?
    jeannaz
    jeannaz's profile
    <463 fans>


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