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      MLG / Sissy captions 65 - Public Exposure Sissy II  
     30 
    High Definition
     2023-08-15 
    Free porn pics of MLG / Sissy captions 65 - Public Exposure Sissy II 1 of  picsFree porn pics of MLG / Sissy captions 65 - Public Exposure Sissy II 2 of  pics
    Double-sized gallery! With this gallery I pass 1,000 uploaded caps to IF, although I couldn't tell you which one is number 1,000 because they aren't written in the order they're uploaded. Some are a tiny touch cursed, but you'll know them when you read...
    Orokana_Shojo
    Orokana_Shojo's profile
    <838 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
    <2,012 fans>
      Interview with a Dominatrix  
     24 
    High Quality
     2023-08-12 
    Free porn pics of  Interview with a Dominatrix 1 of  picsFree porn pics of  Interview with a Dominatrix 2 of  picsFree porn pics of  Interview with a Dominatrix 3 of  picsFree porn pics of  Interview with a Dominatrix 4 of  pics
    Sometimes journalists call me to coordinate an interview. This time a very newbie called me. I realized right away that he didn't know who I was or what exactly my job was about. He thought I was some kind of porn actress... The situation amused me so...
    sissystraight6
    sissystraight691982's profile
    <2,012 fans>
      The Swap Clinic - 23  
     28 
    High Definition
     2023-08-09 
    Free porn pics of The Swap Clinic - 23 1 of  picsFree porn pics of The Swap Clinic - 23 2 of  picsFree porn pics of The Swap Clinic - 23 3 of  picsFree porn pics of The Swap Clinic - 23 4 of  pics
    Scientific advances now allow for the swapping of minds and body parts between two people. Swap Clinics have popped up all around the globe offering this service, for a fee, to the general public. Some swap for money - permanently offering their youth,...
    rickbennett
    rickbennett's profile
    <1,556 fans>
      MLG / Sissy captions 64 - Petplay   
     15 
    High Definition
     2023-08-07 
    Free porn pics of MLG / Sissy captions 64 - Petplay  1 of  picsFree porn pics of MLG / Sissy captions 64 - Petplay  2 of  picsFree porn pics of MLG / Sissy captions 64 - Petplay  3 of  picsFree porn pics of MLG / Sissy captions 64 - Petplay  4 of  pics
    Turns out I had a bunch of petplay adjacent images just waiting for someone to make a request. Hopefully there's something for everyone beyond puppies and kitties. Cap 13 is supercursed and I'm scared about where it came from. Cap 15 is a mild...
    Orokana_Shojo
    Orokana_Shojo's profile
    <838 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
    <2,012 fans>
      MLG / Sissy captions 63 - Sissy Femboi Sluts V  
     15 
    High Definition
     2023-08-07 
    Free porn pics of  MLG / Sissy captions 63 - Sissy Femboi Sluts V 1 of  picsFree porn pics of  MLG / Sissy captions 63 - Sissy Femboi Sluts V 2 of  picsFree porn pics of  MLG / Sissy captions 63 - Sissy Femboi Sluts V 3 of  picsFree porn pics of  MLG / Sissy captions 63 - Sissy Femboi Sluts V 4 of  pics
    The other half of the backlog. That's it, I'm empty now, so if you were ever going to make a request for some caps or a gallery theme, now's the time to do it. Caps 13 and 14 are cursed relative to the rest and Cap 15 confessional was one thing, then I...
    Orokana_Shojo
    Orokana_Shojo's profile
    <838 fans>
      MLG / Sissy captions 62 - Adult Baby Cucks VI   
     15 
    High Definition
     2023-08-07 
    Free porn pics of  MLG / Sissy captions 62 - Adult Baby Cucks VI  1 of  picsFree porn pics of  MLG / Sissy captions 62 - Adult Baby Cucks VI  2 of  picsFree porn pics of  MLG / Sissy captions 62 - Adult Baby Cucks VI  3 of  picsFree porn pics of  MLG / Sissy captions 62 - Adult Baby Cucks VI  4 of  pics
    Finally the backlog is cleared, and somehow this gallery ended up being almost entirely pink. Weird. I wasn't wearing pink while writing them at any point, it just worked out that way. Cap 13 is slightly cursed, cap 15 is a short confessional to round...
    Orokana_Shojo
    Orokana_Shojo's profile
    <838 fans>
      reblog - swimsuit peg.   
     4 
    Low Quality
     2023-08-07 
    Free porn pics of reblog - swimsuit peg.  1 of  picsFree porn pics of reblog - swimsuit peg.  2 of  picsFree porn pics of reblog - swimsuit peg.  3 of  picsFree porn pics of reblog - swimsuit peg.  4 of  pics
    lifeguardsissy
    lifeguardsissy's profile
    <349 fans>
      MLG / Sissy captions 60 - Stupid Sissy Sluts VII  
     15 
    High Definition
     2023-07-29 
    Free porn pics of MLG / Sissy captions 60 - Stupid Sissy Sluts VII 1 of  picsFree porn pics of MLG / Sissy captions 60 - Stupid Sissy Sluts VII 2 of  picsFree porn pics of MLG / Sissy captions 60 - Stupid Sissy Sluts VII 3 of  picsFree porn pics of MLG / Sissy captions 60 - Stupid Sissy Sluts VII 4 of  pics
    Miss me?
    Orokana_Shojo
    Orokana_Shojo's profile
    <838 fans>
      Bikini Beach - You've Just Won a Free Trip!  
     16 
    High Definition
     2023-07-26 
    Free porn pics of Bikini Beach - You've Just Won a Free Trip! 1 of  picsFree porn pics of Bikini Beach - You've Just Won a Free Trip! 2 of  picsFree porn pics of Bikini Beach - You've Just Won a Free Trip! 3 of  picsFree porn pics of Bikini Beach - You've Just Won a Free Trip! 4 of  pics
    Bikini Beach is an island resort that uses Swap Clinic technology to randomly switch visitors into different bodies for a vacation away, even from themselves. body swap, body shift, transform, transformation, mind swap, mind shift, male to female, mtf,...
    rickbennett
    rickbennett's profile
    <1,556 fans>
      Sissy and Feminization Captions 29: Feminized by Family 5  
     20 
    Medium Quality
     2023-07-25 
    Free porn pics of Sissy and Feminization Captions 29: Feminized by Family 5 1 of  picsFree porn pics of Sissy and Feminization Captions 29: Feminized by Family 5 2 of  pics
    Sissy beta bois get feminized by their male step family members. There ain't no turning back the clock once you're forced to wear a frock!
    ViennaSheraton
    ViennaSheraton's profile
    <1,058 fans>
      The Great Shift Experiences - 14  
     34 
    High Definition
     2023-07-25 
    Free porn pics of The Great Shift Experiences - 14 1 of  picsFree porn pics of The Great Shift Experiences - 14 2 of  picsFree porn pics of The Great Shift Experiences - 14 3 of  picsFree porn pics of The Great Shift Experiences - 14 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
    <1,556 fans>
      Gabice in Wonderland  
     24 
    High Quality
     2023-07-23 
    Free porn pics of Gabice in Wonderland 1 of  picsFree porn pics of Gabice in Wonderland 2 of  pics
    Gabrielle followed the rabbit through its hole...and nothing was ever the same. I would like to do the same... will I ever have the courage to do it? (you can see the original pictures in aliciat's gallery"Alice in Sissy Wonderland 1", in...
    sissystraight6
    sissystraight691982's profile
    <2,012 fans>
      Mrs. Crenshaw trains a laundry sissy  
     1 
    High Quality
     2023-07-13 
    Free porn pics of Mrs. Crenshaw trains a laundry sissy 1 of  pics
    Mrs Crenshaw uses sissification to make her laundry boy more compliant. Credit to the brilliant fetish artist Hopkings, picture 281, for inspiring this caption.
    Aikira
    Aikira's profile
    <1,072 fans>
      Magic Transformation - Fun For You  
     11 
    High Definition
     2023-07-10 
    Free porn pics of Magic Transformation - Fun For You 1 of  picsFree porn pics of Magic Transformation - Fun For You 2 of  picsFree porn pics of Magic Transformation - Fun For You 3 of  picsFree porn pics of Magic Transformation - Fun For You 4 of  pics
    Magical transformation story where a cross-dressing guy gets punished by his witchy girlfriend...with a twist! bra, witch, magic, girlfriend, roommate, magic, transformation, curse, coworkers, shower, pee, pov, downblouse, cleavage, skirt, nylons,...
    rickbennett
    rickbennett's profile
    <1,556 fans>
      Other Gender Transformations - 12  
     21 
    High Definition
     2023-07-10 
    Free porn pics of Other Gender Transformations - 12 1 of  picsFree porn pics of Other Gender Transformations - 12 2 of  picsFree porn pics of Other Gender Transformations - 12 3 of  picsFree porn pics of Other Gender Transformations - 12 4 of  pics
    Various gender transformation captions which don't fit into my other categories. Includes: male to female, body swap, sex change, mtf, teen, selfie, bound, asian, chinese, japanese, body hopper, head swap, bra, panties, nylons, high heels, witch, milf,...
    rickbennett
    rickbennett's profile
    <1,556 fans>
      Captions: Sissy, Cuckold, Ballbusting, Domination2  
     108 
    High Definition
     2023-07-08 
    Free porn pics of Captions: Sissy, Cuckold, Ballbusting, Domination2 1 of  picsFree porn pics of Captions: Sissy, Cuckold, Ballbusting, Domination2 2 of  picsFree porn pics of Captions: Sissy, Cuckold, Ballbusting, Domination2 3 of  picsFree porn pics of Captions: Sissy, Cuckold, Ballbusting, Domination2 4 of  pics
    Some of these I made, some of them I got from you guys, some of them I saw on-line and wanted to change something. I hope you enjoy them, they are in this file it is because I did!
    redbird2991
    redbird2991's profile
    <1,272 fans>
      Sissy Captions 3  
     57 
    Medium Quality
     2023-07-07 
    Free porn pics of Sissy Captions 3 1 of  picsFree porn pics of Sissy Captions 3 2 of  picsFree porn pics of Sissy Captions 3 3 of  picsFree porn pics of Sissy Captions 3 4 of  pics
    Sissy captions
    Sissy_Scarlett
    Sissy_Scarlett's profile
    <435 fans>
      Good Gurls Rehab - 12  
     23 
    High Definition
     2023-07-07 
    Free porn pics of Good Gurls Rehab - 12 1 of  picsFree porn pics of Good Gurls Rehab - 12 2 of  picsFree porn pics of Good Gurls Rehab - 12 3 of  picsFree porn pics of Good Gurls Rehab - 12 4 of  pics
    Good Gurls Rehab - Using Swap Clinic technology, GG Rehab swaps troubled, disruptive boys into productive young women. Some are taken to the clinic by their parents. Others are forced to attend after getting in trouble with the law. A few even...
    rickbennett
    rickbennett's profile
    <1,556 fans>
      Sissy and Feminization Captions 27: Feminized by Family 4   
     20 
    High Quality
     2023-07-05 
    Free porn pics of  Sissy and Feminization Captions 27: Feminized by Family 4  1 of  picsFree porn pics of  Sissy and Feminization Captions 27: Feminized by Family 4  2 of  pics
    Beta bois are forcibly feminized into submissive sissies by sinister stepsisters, and demoted to docile darling daughters by sadistic stepmothers and merciless moms.
    ViennaSheraton
    ViennaSheraton's profile
    <1,058 fans>
      Miss Stacey  
     24 
    High Definition
     2023-06-26 
    Free porn pics of Miss Stacey 1 of  picsFree porn pics of Miss Stacey 2 of  pics
    I have known Miss Stacey for over 15 years. Saying "I have known Miss Stacey" is actually a mistake: I keep discovering her every day. How to describe her? She is beautiful, intelligent, sexy, strong, loyal and protective. She is the one who discovered...
    sissystraight6
    sissystraight691982's profile
    <2,012 fans>
      Sissy and Feminization Captions 26: June Brides Special  
     12 
    Medium Quality
     2023-06-25 
    Free porn pics of Sissy and Feminization Captions 26: June Brides Special 1 of  picsFree porn pics of Sissy and Feminization Captions 26: June Brides Special 2 of  pics
    Beta bois become beautiful blushing brides when times are tough or there's changing tides.
    ViennaSheraton
    ViennaSheraton's profile
    <1,058 fans>
      Sissy and Feminization Captions 25: Feminized by Family 3  
     20 
    Medium Quality
     2023-06-18 
    Free porn pics of Sissy and Feminization Captions 25: Feminized by Family 3 1 of  picsFree porn pics of Sissy and Feminization Captions 25: Feminized by Family 3 2 of  pics
    Father's Day Special. Dads and stepdads sissify sons into cock-craving cuties. A few captions are reposted from older galleries.
    ViennaSheraton
    ViennaSheraton's profile
    <1,058 fans>
      I need somebody tonight... (2)  
     24 
    High Definition
     2023-06-16 
    Free porn pics of I need somebody tonight... (2) 1 of  picsFree porn pics of I need somebody tonight... (2) 2 of  picsFree porn pics of I need somebody tonight... (2) 3 of  picsFree porn pics of I need somebody tonight... (2) 4 of  pics
    I feel alone again, would someone like to come and comfort me?
    sissystraight6
    sissystraight691982's profile
    <2,012 fans>


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