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Free porn pictures 10 25 50 100 150 results per page   Search for: Filter by: Any size Small Medium Large Huge Anytime Today This week This month  Gallery Name   Images   Quality   Added    Randomness2    14   2025-04-05  subbiesissy <106 fans>   Sissy In Her Black Lingerie    209   2025-04-05  Sissy in her black lingerie Snuskis80 <164 fans>   SISSY GIF'S CAPTIONS-76 Young/Older Edition.    15   2025-04-05  kparc1212 <4,870 fans>   Sissy Julie Allison Swimwear: Nude Slingshot Bikini    27   2025-04-05  Sissy Julie Allison Swimwear: Nude Slingshot Bikini JulieAllison <646 fans>   vicky vicks random images updated    23   2025-04-05  first time posting, please be kind or naughty. this gallery will just be random pics i will add to from time to time vicky_vicks <476 fans>   Gallery_166_my_naked_body_cock_butt_2    8   2025-04-05  Pictures of me, please comment freefriki <375 fans>   Aline Travestie (782)    20   2025-04-05  Aline travestie en lingerie aline_trav <1,474 fans>   Expose faggot Roberta     1   2025-04-05  Expose the sissy faggot for the slut she is . sissy_roberta <108 fans>   Twisted Sissy Caps - 1    14   2025-04-05  Littleuce <59 fans>   Guys Mix 72    272   2025-04-04  cute1foryou <2,052 fans>   Help me choose which looks best. I can't decide.    12   2025-04-04  New Booty shorts for the upcoming spring season to wear around the town and house. What colour do you think is best between the red, blue, and green. StupidJOSSissy <216 fans>   Implied Sissy Captions    36   2025-04-04  Sissy captions where the graphic isn't evident that a sissy is participating, but the implication along with the text still makes it sexy as hell! Lyonrun <659 fans>   SiSSY CD SAMANTHA ReUP Gallery 4    53   2025-04-04  Last of the ReUP galleries. This was fun! Hope you enjoy. I'll post new material as soon as life stops being so busy. SexySissySlutS <794 fans>   My Feminist Boss 18    24   2025-04-04  I've had a few alpha female bosses in my career, beginning with my first job. In every case, the woman, no matter how qualified, found it necessary to prove themselves, sometimes at my expense. I can put up an act about being alpha, but after a while,... krista024 <3,018 fans>   Taking stock and trying on my first outfit    4   2025-04-04  Being a closeted crossdresser the day you have the free time to try on an outfit and put out all your toys is a day that makes you leak with anticipation. So much so that I only had a few hours today to get my toys and outfits out of storage. However I... Caged_Gab <764 fans>   Extreme Captions     167   2025-04-04  WARNING very offensive pavlovsdog666 <758 fans>   SISSY - GIF'S CAPTIONS - 75    16   2025-04-03  kparc1212 <4,870 fans>   Sissies in Bondage 12    20   2025-04-03  KarinaClarkeTV <986 fans>   Beta    3   2025-04-03  loser Betalincel <184 fans>   Ex girlfriend caption     1   2025-04-03  She broke up with me a long time ago and probably has a real man as her boyfriend now and not a cock sucking sissy faggot like me . sissy_roberta <108 fans>   Sissy Chastity Maintenance/Dress up time    7   2025-04-03  Sissyytboi <351 fans>   Show off     5   2025-04-03  sissyjustinaxx <2,372 fans>   Babysitters and Cuckoldsitters in Control 23    24   2025-04-03  nBabysitter; 1. A person engaged to care for one or more children in the temporary absence of parents or guardians. 2. A person who cares for or watches over someone or something that needs attention or guidance. You won't be getting guidance here; you... krista024 <3,018 fans>   Camera Fun 23 Join me if you like    37   2025-04-03  A mix of older and brand new pictures JanH <1,070 fans>   Sissy Captions - Encouragements 4    45   2025-04-03  Sissy Captions Sissy_Scarlett <1,591 fans>   Gallery_165_my_naked_body_cock_butt_1    8   2025-04-03  Pictures of me, please comment freefriki <375 fans>   Castration for Roberta captions     2   2025-04-03  sissy_roberta <108 fans>   Uk Sissy cuck (kik ckslve)    13   2025-04-02  Sissy cuckold dressed up in his girlfriends lingerie. He is a webslut who has to eat his own cum for anyone who contacts on kik Sissycuckslave <3 fans>   Some favourites 2    78   2025-04-02  sissisubboy <1,379 fans>   SISSY TOONS - CAPTIONS - 7    16   2025-04-02  kparc1212 <4,870 fans>   Clothes I'd like to wear and girls I'd like to look like 29    48   2025-04-02  When I first started making galleries I never thought I would find so many clothes I'd like to wear, yet here it is gallery 29. This is a view of the type of clothes that I'd love to try on and wear. My tastes change from time to time, and this is just... krista024 <3,018 fans>   Crossdressing - sissy - Pretty dress and locked up    6   2025-04-02  Dressed up in cute black dress and stockings, safely locked in chastity this time. sissy chastity chastity cage pink clitty crossdressing dressupskirtpanties flashing lylyoko <203 fans>   Roberta is encouraged to give blowjob     1   2025-04-02  sissy_roberta <108 fans>   Sissy Gif/ Non-Gif Caps 19    40   2025-04-02  emirose2722 <930 fans>   Sissy Captions 46    40   2025-04-01  Sissy Captions Sissy_Scarlett <1,591 fans>   Gallery_164_my_cock_foreskin_and_cockhead    6   2025-04-01  Pictures of me, please comment freefriki <375 fans>   Sissy White Boy    12   2025-04-01  Sissy pictures of myself that are free to be reposted or captioned how ever you like! 🥰 Sissyytboi <351 fans>   Daughters and Mothers In Control 50    24   2025-04-01  All pictures are intended to comply with Image Fap rules and regulations. All images are believed to be of legal age participants. All images used were gathered from other existing Image Fap galleries. These are the empowered women we know, Mothers who... krista024 <3,018 fans>   Orlandoed 001 - 024    24   2025-04-01  Re-Uploads from the Orlandoed Gallery. Men wake up having undergone the transformation of Orlando. The eponymous character from the novel by Virginia Woolf Obsidian95 <867 fans>   Crossdressing - sissy - cumming handsfree in fishnet bodysuit    7   2025-04-01  Dressed up in sexy lingerie having a little fun and ending up cumming handsfree. Don't hesitate to comment. sissy slut lingerie fishnet ass crossdressing cumming cum handsfree amateur orgasm bussy femboy panties lylyoko <203 fans>   Delightfully drawn sissy&rsquo;s and bimbos    100   2025-04-01  essceelle <1,013 fans>   Femdom Foot Captions 20    9   2025-04-01  clthong2 <600 fans>   Bred Gurls    23   2025-04-01  Sissy boipussies dripping with cum Lyonrun <659 fans>   Diaper Captions 159    9   2025-03-31  clthong2 <600 fans>   Advanced Cuck Ideas    24   2025-03-31  Hope you like these too coldsoup <479 fans>   GoonerAudioLabs April 2025 Gooner/Sissy/Cuckold Captions    28   2025-03-31  Join the Patreon for access to exclusive gooning audio files! GoonerAudioLab <686 fans>   Sissy and Crossdress Bride    12   2025-03-31  Caption_Maker <974 fans>   Jana-Slave german Caps    6   2025-03-31  Caption_Maker <974 fans>   crossdressing - sissy - plugged in stockings    6   2025-03-31  Sissy dressed up all cute with sexy stockings while flashing a little under my skirt. sissy crossdressing crossdresser panties plug stockings upskirt ass cock sph upskirt legs feet lylyoko <203 fans>   Sissy faggot Roberta's id cards     2   2025-03-31  sissy_roberta <108 fans>   Aline Travestie (781)    20   2025-03-31  Aline travestie en lingerie et en cage aline_trav <1,474 fans>   Anja blank ass and hold-up nylons    30   2025-03-30  Me Gallone in Hotel room Anja_69 <344 fans>   sissy fag captions    3   2025-03-30  cfagboy <1,751 fans>   Topless Sissy Micki    17   2025-03-30  Topless little sissy Micki drops her panties and is eager to service some cocks! Micknude <248 fans>   Announcement     4   2025-03-30  nOn 27.3.2025 my wife and I finally confirmed and stamped our sissy cuckold - hotwife relationship. Thanks to my colleague who jumped to my rescue and showed her what fucking is. The confirmation followed a few hours after he spread her horny pussy. I... deadollyslo <625 fans>   Best Friend to Femboy    8   2025-03-30  You’ve been best friends since the 4th grade but now you are older he wants to evolve your friendship but still be your closest friend jonblacker <6,228 fans>   St Jezebel's school for Gurls - Training    10   2025-03-30  Sometimes a family, usually the father, realise their son is born to be a sissy. St Jezebel’s boarding school exists to turn sons into effeminate sissy sluts. Training is essential for sissy boys to understand their place in the world. jonblacker <6,228 fans>   Andrea a slut since youth    10   2025-03-30  I wear lingerie every day, love to tease men, hard cock and make them fuck me and cum in my face.. AndreaMoreau <35 fans>   myself - sissy - crossdressing, my butt and cock    7   2025-03-30  some pics of me, dressing up... in panties... and of my cock. sissy femboy crossdressing crossdresser panties ass pantyboy lingerie skirt pink sph ass yoga stockings lylyoko <203 fans>   Sissy Captions 45    40   2025-03-29  Sissy Captions Sissy_Scarlett <1,591 fans>   Sissy Captions for Me    8   2025-03-29  micd90 <137 fans>   Andrea    28   2025-03-29  Andrea dressed up as a street slut, this is how I usually meet with men. AndreaMoreau <35 fans>   sissy goals and inspirations 10    17   2025-03-29  A collection of bodies and people I am jealous of and want to be, and situations and fantasies I'd love to experience one day. bbwsissyboi <114 fans>   sissy goals and inspirations 9    22   2025-03-29  A collection of bodies and people I am jealous of and want to be, and situations and fantasies I'd love to experience one day. bbwsissyboi <114 fans>   Sissy Julie Allison Outfit: Plaid Skirt and Lingerie    24   2025-03-29  Sissy Julie Allison Outfit: Plaid Skirt and Lingerie JulieAllison <646 fans>   sissy training     11   2025-03-29  LaraLocke <3,327 fans>   Gallery_163_my_tight_butt_hoLLLe_and_cock_balls    6   2025-03-29  Pictures of me, please comment freefriki <375 fans>   Anderson Camargo Garcia Sissy Exposed     21   2025-03-29  I'm Daisy but my real name is Anderson Camargo Garcia from Colombia, I like risky exposure. This gallery contains my photos and my sissy ID with all my info, with the objective that you download my photos and publish me everywhere (free use photos).... DaisySophie <281 fans>   SiSSY CD SAMANTHA ReUP Gallery 3    58   2025-03-29  These were alot of fun to go through and edit. Hope you enjoy! SexySissySlutS <794 fans>   Caged Girl exposed    8   2025-03-29  Me SissyGurlnbecomes more and more my life dsiss87 <1,932 fans>   Your sissy faggot reaction/mostly BBC x Sissy    16   2025-03-28  Captions of your sissy reaction when big meaty delicious cocks appear and mostly black ones, enjoy and jerk off or finger yourself hard. Sssy_Maker <1,322 fans>   Sissy Captions - Bimbo 5    45   2025-03-28  Sissy Captions Sissy_Scarlett <1,591 fans>   Shuggah Becums Golden Hoe #3    31   2025-03-28  WhiteShuggah <95 fans>   Sissy Captions 70    16   2025-03-28  Alyssa38b <1,917 fans>   Transformed from Happy Man to Baby Sissy Sex Slave Captions    24   2025-03-28  Forcibly feminized and made to live as a baby girl, complete with diapers, pacifier and an evil concoction in his bottle! Read my full length forced feminization and sissy humiliation e-books, exclusively from the online publisher, at... Candy_Runt <4,842 fans>   Shuggah Becums Golden Hoe #2    30   2025-03-28  WhiteShuggah <95 fans>   Shuggah Becums Golden Hoe    30   2025-03-28  WhiteShuggah <95 fans>   Seren new caps 332    12   2025-03-28  APRIL 2023. I have started to post a new set of captions, created almost entirely on smartphone, using face, photography and text apps. All the 'base' pics are from legal sites/sources (18 plus). The face swaps are either celebs/pornstars from readily... SerenPidyn <1,254 fans>   My Shoe Collection (2025)    47   2025-03-28  After my last 'purge' a couple of years ago, Shanine was calling again so it was time to rebuild my wardrobe. I hope you like xx ShanineM <208 fans>   Fun pics    6   2025-03-27  Some new pics I had fun taking :) Storm_visual <431 fans>   SISSY - GIF'S CAPTIONS - 74    16   2025-03-27  kparc1212 <4,870 fans>   Advanced Cuck Ideas    24   2025-03-27  Thanks as always for the interest and support coldsoup <479 fans>   Sissy Tanja    5   2025-03-27  KylieM <1,649 fans>   sissymaid march 2025    11   2025-03-27  Myself dressed up as a sissymaid ready to wank myself off knifty764 <659 fans>   Gallery_14_me_crossdressing_sexy_red_panties_and_skirt    7   2025-03-27  Pictures of me, please comment freefriki <375 fans>   GAY SISSY BABECOCK SMOKING CAPTIONS    8   2025-03-27  She knows. ghipstervisual <778 fans>   Femdom Captions 63    7   2025-03-26  clthong2 <600 fans>   Sissy Faggot Sucking    49   2025-03-26  Another cock hungry slut who is happiest with a mouth full. gus_lorenz <7,398 fans>   Tif's. Fanny    8   2025-03-26  TifFannySs <25 fans>   Advanced Cuck Ideas    24   2025-03-26  Thanks flor all your support and interest coldsoup <479 fans>   Swapped at Birth - 01    19   2025-03-26  Swapped at Birth - transform, body swap, sex change, body switch, mind swap, male to female, mtf, sissy, bra, blowjob, oral, date, cleavage, doctor, regret, panties, lingerie, boob job, surgery, implants, collar, skirt, office, coworker, roommate,... rickbennett <2,029 fans>   Unrelenting Cruelty to Sissies 10    10   2025-03-26  femdom, dominatrix, mistress, sissy, shemale, tranny, feminization, humiliation, maid Womanservant <973 fans>   SISSY - GIF'S CAPTIONS - 73    16   2025-03-26  kparc1212 <4,870 fans>   Valkyrie of Lust 55 (me, Femboy)    38   2025-03-26  ValkyrieOfLust <472 fans>   More Sissy and Sluts favourites     42   2025-03-26  sissymaster202 <872 fans>   Gallery_162_me_with_open_legs    3   2025-03-26  Pictures of me, please comment freefriki <375 fans>   Gallery_13_me_crossdressing_sexy_blue_panties_and_shorts_B    5   2025-03-26  Pictures of me, please comment freefriki <375 fans>   Aline Travestie (780)    20   2025-03-26  Aline travestie en lingerie aline_trav <1,474 fans>   Censored big tittied goth girls for betas Vol 1    12   2025-03-26  I know you betas leak for goth Mommies 😈😘 Please share and caption! Let me know if you have a request! ❤️ cocklover1989 <762 fans>   Diaper Captions 158    7   2025-03-25  clthong2 <600 fans>   Brainwashing Myself - Living the Dream    44   2025-03-25  The gurl on the first picture is totally a vibe... all dolled up, just about cummed on and swallowed some and bursting out of happiness, showing the world how proud she is to be a Sissy slut. I want this! wurster <2,519 fans>   Bikini Femboy    1   2025-03-25  chanhaven56 <69 fans>   She Forced Him to Dress and Act Like a Whore - Captions    24   2025-03-25  Candy_Runt <4,842 fans>   Me    3   2025-03-25  SisstasticUk <28 fans>   Advanced Cuck Ideas    24   2025-03-25  Hope you like theses too coldsoup <479 fans>   Women take control 10: It all makes sense    25   2025-03-25  If you are a sissy, a cuckold, a beta-boi and you love being dominated, controlled and told what to do and when to do it by a gorgeous woman, then this gallery is for you LongstockingsM <932 fans>   Young sissy bitch for old perverts    8   2025-03-25  Mrsmanmrs <953 fans>   Sissy - Crossdressing Captions    16   2025-03-25  kparc1212 <4,870 fans>   Gallery_161_my_balls_and_cock    5   2025-03-25  Pictures of me, please comment freefriki <375 fans>   You're Nothing But a Loser 127    24   2025-03-25  This gallery is intended to tap into the insecurities that a loser has, especially those involving his abilities when it comes to women. The reason you're here is because you're nothing but a loser. krista024 <3,018 fans>   Gallery_63_my_butt_and_co ck_crossdressing_PART_2    6   2025-03-25  Pictures of me, please comment freefriki <375 fans>   Sissy Whore 11    45   2025-03-24  Sissy Whore Sissy_Scarlett <1,591 fans>   Sissification temptation    11   2025-03-24  SisstasticUk <28 fans>   Seren new caps 331    12   2025-03-24  APRIL 2023. I have started to post a new set of captions, created almost entirely on smartphone, using face, photography and text apps. All the 'base' pics are from legal sites/sources (18 plus). The face swaps are either celebs/pornstars from readily... SerenPidyn <1,254 fans>   A Collection of Sissies and Crossdressers #03    7   2025-03-24  Wim_bull <109 fans>   I bet my ass is nicer than your wife/GF. COMMENT AND TRIBUTE PLZ    35   2025-03-24  Ass, peach, phat ass, white boi, sissy, jos, trash, cum bucket, hoe, slave, BBC, Arab, for older, for obese, pegging, fuck me, sexy ass, Short shorts, master wanted, buy or rent, stupid, slut, feminization, booty, tribute, cunt me, bug chaser, poz me. StupidJOSSissy <216 fans>   Femdom Sissy Strapon 3D and AI images    56   2025-03-24  Femdom sissy strapon pegging, CBT, spitroast, cock milking images. Mike32174 <586 fans>   Cocks and Cum for Everyone!    23   2025-03-23  Big cock shemales and may. Gorge yourself on cum! Guzzler35 <262 fans>   MLG / Sissy captions 81 - AI Futa Mistress    40   2025-03-23  Maybe this will be the gallery to get me over 1,000 fans, who knows. I tried to select photo-realistic images, but we're talking about futas here, they're fantasy creatures, so if gorgeous women with horse cocks aren't your thing maybe skip this one.... Orokana_Shojo <1,101 fans>   James's Secret (Pokemon)    35   2025-03-23  If youre a fan of pokemon then you know James and how his sexuality is questionable, Ive searched high and low to find what we're all probably thinking and here it is in styles of the artists who made them and all the same idea. HarleyRaven <300 fans>   SISSY - GIF'S CAPTIONS - 72 - Cuckold Husband Edition    16   2025-03-23  kparc1212 <4,870 fans>   Rachel and Marty Get Blacked    6   2025-03-23  SissySlutMarty <524 fans>   Sissy Captions - BBC 6    45   2025-03-22  Sissy Captions Sissy_Scarlett <1,591 fans>   Sissy Desiree - The joy of dressing    43   2025-03-22  Sissy Desirée preparing for daddy and playing around while waiting.. Feel free to use these pics for exposure and captions! KylieM <1,649 fans>   Captions - Interracial Sissy GIF's - 14    16   2025-03-22  kparc1212 <4,870 fans>   Spending a Cloudy Day    6   2025-03-22  Just me and daddy lounging on our bed spending a cloudy day fondling myself ;) Ashleygurrl <204 fans>   ABDL TRANS CAPTIONS    9   2025-03-22  ABDL trans captions I made. Sissy_Finn <145 fans>   Sissy Julie Allison Lingerie: Purple Teddy    20   2025-03-22  Sissy Julie Allison Lingerie: Purple Teddy JulieAllison <646 fans>   Tumblr rescues    3   2025-03-22  Rocketboost <18 fans>   Censored latex strapon Mommies for betas    14   2025-03-22  Mommy is about to top you beta! Please share and caption ❤️😘 Also let me know if you have a request! 🫰🏼 cocklover1989 <762 fans>   Censored Sph for betas Vol. 2    12   2025-03-22  Please caption and share!!! ❤️😘 Also let me know if you have a request! 🫰🏼 cocklover1989 <762 fans>   fifi    17   2025-03-21  Scat play and Sissi look Realdk <8 fans>   Sph censored strapon Mommies Vol. 1    18   2025-03-21  Combined two of my favorite things! Sph and Strapon Doms! 🥰 Please share and caption! 😘 Also let me know if you have a request! 🫰🏼 cocklover1989 <762 fans>   diaper sissy    9   2025-03-21  me ind diaper hansen23 <153 fans>   diaper dildo sissy    13   2025-03-21  me my diaper playing whint dildos hansen23 <153 fans>   Global sissy Inspiration 110    30   2025-03-21  FrenchSissySam <2,944 fans>   Global sissy Inspiration 109    32   2025-03-21  FrenchSissySam <2,944 fans>   Hotwives and Cuckolds 30    31   2025-03-21  _kink4all_ <414 fans>   Hotwives and Cuckolds 29    24   2025-03-21  _kink4all_ <414 fans>   Show me how much you need my cock, boi    13   2025-03-21  Falling further and further under the spell of my cock mtcpl4sex <2,437 fans>   Hotwives and Cuckolds 28    24   2025-03-21  _kink4all_ <414 fans>   St Jezebel's school for Gurls - Conversion Therapy (Toon)    8   2025-03-21  Sometimes a family, usually the father, realise their son is born to be a sissy. St Jezebel’s boarding school exists to turn sons into effeminate sissy sluts. Being turned into sissy fucktoys sometimes requires harsh conversion therapy.... jonblacker <6,228 fans>   The Swap Clinic - 28    24   2025-03-21  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 <2,029 fans>   Gallery_160_my_cock_foreskin_and_cockhead    5   2025-03-21  Pictures of me, please comment freefriki <375 fans>   collection of sissy, femboys, trans. Part 27    12   2025-03-21  CiGn <335 fans>   Gallery_62_my_butt_and_co ck_crossdressing_PART_1    6   2025-03-21  Pictures of me, please comment freefriki <375 fans>   Aline Travestie (779)    20   2025-03-21  Aline travestie en lingerie et en cage aline_trav <1,474 fans>   Diaper Captions 157    9   2025-03-21  clthong2 <600 fans>   Censored SPH for betas Vol. 1    10   2025-03-21  Censored just for your little Prejacs out there 😘 Please share and caption!! ❤️ Also let me know if you have a request! 🫰🏼 cocklover1989 <762 fans>   Censored clothed strapon Mommies Vol. 1    15   2025-03-21  I’m having so much fun making these censored images! 🥰 If anyone has requests let me know and please share and caption! ❤️ cocklover1989 <762 fans> :: prev :: | 1 | ... | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | :: next ::