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    Displaying results for 'pick*' - View all videos for 'pick*'
     Gallery Name 
     Images 
     Quality   Added 
      Sissy Gif/ Non-Gif Caps 12  
     42 
    High Quality
     2024-04-20 
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    Help Me Please? Is a pseudo CYOA type thing. Maybe not so much a CYOA as a YSOCWTSWY (Your Significant Other Chooses Whether to Stay With You),nbut you can pick the path you like the most... Or not and read them all. It's your life...
    emirose2722
    emirose2722's profile
    <809 fans>
      Picky a Chicky  
     9 
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     2024-04-08 
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    SailorsCharm
    SailorsCharm's profile
    <496 fans>
      Pandora Sissy Pick One  
     8 
    High Definition
     2023-10-07 
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    CatrinaBethXO
    CatrinaBethXO's profile
    <328 fans>
      Sissy situations - pick your choices!  
     46 
    High Quality
     2023-09-13 
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    Assign letters to numbers - each situation to a scenario. Choose your sissy destiny in these captioned pic compilations!
    Scolioz
    Scolioz's profile
    <26 fans>
      HENTAI CAPTIONS: BULLYING PROBLEM  
     8 
    High Quality
     2023-05-28 
    Free porn pics of HENTAI CAPTIONS: BULLYING PROBLEM 1 of  picsFree porn pics of HENTAI CAPTIONS: BULLYING PROBLEM 2 of  pics
    b-being a si--i-i mean, um, a-a slightly less strong alpha male...--can be tough sometimes!! p-people just love picking on us... c-calling us sissies... f-forcing us to have sex w-with all their big, meeeeeaty, alpha cocks... hngghhh...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,317 fans>
      fantasy world: women has big cocks-- you pick  
     19 
    High Quality
     2022-12-22 
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    El-E
    El-E's profile
    <439 fans>
      MLG / Sissy captions 20 - Shemale Femdom  
     15 
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     2022-08-15 
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    If I'm being honest, I'm not sure these are my best work - I picked a theme and tried to stick to it but a few could have probably done with a bit more time in the oven. I wore nothing except PVC fetish platform heels and my pink chastity cage. Excited...
    Orokana_Shojo
    Orokana_Shojo's profile
    <840 fans>
      SISSY CAPTIONS 50: SWORDS AND SORCERY (HENTAI) II  
     14 
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     2021-12-04 
    Free porn pics of SISSY CAPTIONS 50: SWORDS AND SORCERY (HENTAI) II 1 of  picsFree porn pics of SISSY CAPTIONS 50: SWORDS AND SORCERY (HENTAI) II 2 of  picsFree porn pics of SISSY CAPTIONS 50: SWORDS AND SORCERY (HENTAI) II 3 of  picsFree porn pics of SISSY CAPTIONS 50: SWORDS AND SORCERY (HENTAI) II 4 of  pics
    We're heading back into the fantasy world for this set of captions! Between mind-altering magic, powerful transformation spells, and just good old-fashioned alpha dickings, there's no shortage of ways to end up a brainless sissy cumslut in high-magic...
    FEMINYZE-CAPTI
    FEMINYZE-CAPTIONS's profile
    <4,317 fans>
      My Ex Wife 3  
     12 
    High Definition
     2021-10-17 
    Free porn pics of My Ex Wife 3 1 of  picsFree porn pics of My Ex Wife 3 2 of  picsFree porn pics of My Ex Wife 3 3 of  picsFree porn pics of My Ex Wife 3 4 of  pics
    I was useless as a Man for my ex wife, and my limp little penis has still not been inside a woman's cunt. Luckily she met many Men during our marriage, and they gave her the sex she wanted. My ex wife loved to party and pick up men, while I was alone...
    CaptionedSissy
    CaptionedSissy's profile
    <1,590 fans>
      I Love Hot Sissy CD TV - Captions - All Comments welcome   
     16 
    High Quality
     2021-03-02 
    Free porn pics of I Love Hot Sissy CD TV - Captions - All Comments welcome  1 of  picsFree porn pics of I Love Hot Sissy CD TV - Captions - All Comments welcome  2 of  picsFree porn pics of I Love Hot Sissy CD TV - Captions - All Comments welcome  3 of  picsFree porn pics of I Love Hot Sissy CD TV - Captions - All Comments welcome  4 of  pics
    More of what I like best, hot picks of Sissy Crossdressers that remind me of me. Comments welcome - cum one cum all
    MeetMarilyn
    MeetMarilyn's profile
    <3,133 fans>
      The Magic Bra Game  
     10 
    High Quality
     2020-04-20 
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    Let's be honest, you've always wanted to be a woman. Now, you have the chance. You follow a witch to be the back of her magic shop where she opens a drawer and offers you the choice of nine different colors of bra. Your choice will dictate the type of...
    rickbennett
    rickbennett's profile
    <1,562 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
    <1,562 fans>
      Shave Time For You !  
     1 
    Medium Quality
     2019-03-04 
    Free porn pics of Shave Time For You ! 1 of  pics
    Pick a number from your brain !
      HOUSE-HUSBANDS 2  
     26 
    High Quality
     2018-07-28 
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    YOU MAY BE LOOKING AFTER THE BABY, BETWEEN JOBS, DOING THE HOUSEWORK, VISITING THE SUPERMARKETS (PRIME PICK-UP LOCATIONS) OR EVEN (LOL) "WORKING FROM HOME"! RELAX AND ENJOY THE CHANCES TO WIDEN YOUR SEXUAL HORIZONS (AND HAVE YOUR "PUSSY" WIDENED FOR...
    michelle6969
    michelle6969's profile
    <1,730 fans>
      The Great Shift - Choose Your Shift 01  
     11 
    High Definition
     2017-03-08 
    Free porn pics of The Great Shift - Choose Your Shift 01 1 of  picsFree porn pics of The Great Shift - Choose Your Shift 01 2 of  picsFree porn pics of The Great Shift - Choose Your Shift 01 3 of  picsFree porn pics of The Great Shift - Choose Your Shift 01 4 of  pics
    Pick a number and see what body you end up with after the Great Shift. Be sure to leave a comment on the body your receive, along with your thoughts of it and the first thing that you would in it. ---- The Great Shift - On a typical day like any...
    rickbennett
    rickbennett's profile
    <1,562 fans>
      Perfect Reasons to Pick a Sissy Over a Woman  
     29 
    High Quality
     2016-09-25 
    Free porn pics of Perfect Reasons to Pick a Sissy Over a Woman 1 of  picsFree porn pics of Perfect Reasons to Pick a Sissy Over a Woman 2 of  picsFree porn pics of Perfect Reasons to Pick a Sissy Over a Woman 3 of  picsFree porn pics of Perfect Reasons to Pick a Sissy Over a Woman 4 of  pics
    Don't make the same mistake many men do, consider adopting a sissy before it's too late. Read the captions and you'll agree.
    Darcycon
    Darcycon's profile
    <73 fans>
      Feminization: Sissys World: Waiting to be picked up: Vol. 01  
     24 
    High Quality
     2016-07-05 
    Free porn pics of Feminization: Sissys World: Waiting to be picked up: Vol. 01 1 of  picsFree porn pics of Feminization: Sissys World: Waiting to be picked up: Vol. 01 2 of  picsFree porn pics of Feminization: Sissys World: Waiting to be picked up: Vol. 01 3 of  picsFree porn pics of Feminization: Sissys World: Waiting to be picked up: Vol. 01 4 of  pics
    Alertme1159
    Alertme1159's profile
    <5,835 fans>
      Reblog ideas for you  
     21 
    High Quality
     2015-01-10 
    Free porn pics of Reblog ideas for you 1 of  picsFree porn pics of Reblog ideas for you 2 of  picsFree porn pics of Reblog ideas for you 3 of  picsFree porn pics of Reblog ideas for you 4 of  pics
    Here are some ideas for you to add to your site. I have been seeing a few more of these reblogs and they are fascinating. Thought I would try a few. Let me know if you like them. Send me your pick and I will REBLOG it.
    patches451
    patches451's profile
    <2,165 fans>
      Prom Date Dilemma - Cumtraptions Nasty Shemale Sissy Captions  
     1 
    High Quality
     2014-10-09 
    Free porn pics of Prom Date Dilemma - Cumtraptions Nasty Shemale Sissy Captions 1 of  pics
    Prom Date Dilemma Ever since I can remember Tommy has been my best friend. I mean sure he is a couple years older than me and kind of a bad boy, but he has always been so sweet and kind. When Cindy said she wouldn’t go to his senior prom with him I...
    cumtraptions
    cumtraptions's profile
    <654 fans>
      Make a pick: him or her 1  
     12 
    High Quality
     2012-07-19 
    Free porn pics of Make a pick: him or her 1 1 of  picsFree porn pics of Make a pick: him or her 1 2 of  picsFree porn pics of Make a pick: him or her 1 3 of  picsFree porn pics of Make a pick: him or her 1 4 of  pics
    Make your pick between him and her
    markusfrot
    markusfrot's profile
    <2,904 fans>
      Archive Sissy Captions  
     66 
    Medium Quality
     2012-06-09 
    Free porn pics of Archive Sissy Captions 1 of  picsFree porn pics of Archive Sissy Captions 2 of  picsFree porn pics of Archive Sissy Captions 3 of  picsFree porn pics of Archive Sissy Captions 4 of  pics
    Found a LOT of older archived captioned and non-captioned shemale futa-fakes that I had done and forgotten about - thought I might upload them here. Some of the quality and workmanship leaves a little to be desired as I was just starting out with...
    SheerMistress
    SheerMistress's profile
    <1,176 fans>
      Shemale Captions #2: The Nightclub Pickup  
     18 
    Medium Quality
     2010-04-04 
    Free porn pics of Shemale Captions #2: The Nightclub Pickup 1 of  picsFree porn pics of Shemale Captions #2: The Nightclub Pickup 2 of  picsFree porn pics of Shemale Captions #2: The Nightclub Pickup 3 of  picsFree porn pics of Shemale Captions #2: The Nightclub Pickup 4 of  pics
    thegooddoctor
    thegooddoctor's profile
    <27 fans>







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