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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    Crossdress Gallery 63    14   2025-07-01  Short_Confiden <291 fans>   You take my coat and this is what I'm wearing underneath     8   2025-07-01  adma8890 <119 fans>   Censored Trans Captions for Betas Vol. 2    7   2025-07-01  People asked for more so here they are! Lol DM me for any requests cocklover1989 <689 fans>   Sissy Cuckolds 42    317   2025-07-01  Pathetic feminized sissy cuckolds under the heel of their cuckoldress wives and other significant women in their lives and they have to serve them all and the real men their wives date and fuck! nothing is ever easy for the sissy cuckold it has to... sissycarla49 <2,390 fans>   Betasafe Censored Pornstars 13    100   2025-06-30  Censored pornstars for betasafe sissy bois. Jerk off to feet, high heels and bbc, loser. Simp to pixels of women and transsexuals that real men get to look at all the time. wesmantooth <782 fans>   Femdom Feminization Captions 7 (Chastity, Pegging, Petplay)    10   2025-06-30  cha0self <363 fans>   Sissy shyboi77 first time exposed    4   2025-06-30  I hope you like it shyboi77 <12 fans>   Dominant Women Humiliating Beta Bitch Bois - sissy captions    24   2025-06-30  I love the idea of a strong woman taking control over my life, forcing me to undergo HRT, wear the tiniest cock cage and the sluttiest clothes imaginable, then making me show off my hormone puffed titties to people who once respected me! - If... Candy_Runt <4,619 fans>   Silly Sissy Captions    9   2025-06-30  Looking stupid is one of the sexiest things for a sissy. Rile-Rile <85 fans>   My AI BBC Sissy Fantasy    195   2025-06-30  sissy confirmation nikkibritney <930 fans>   Bondage gifs of me    8   2025-06-30  Currently in a consensual blackmail arrangement with SweetChloe, who made me perform on cam in bondage and has now ordered me to post these gifs from the session Gazbo999 <183 fans>   Sissified and Feminized Cuckold Captions    24   2025-06-30  Sissy spouses and beta boyfriends are bested by belligerent bulls and forced to feminize by the wicked women in their lives. Their cringing cuckold condition isn't even their greatest shame as many meek males become tormented trannies, cucked... ViennaSheraton <1,368 fans>   Animated Sissy GIF Captions 21 (Sissy Rescue)    9   2025-06-29  All across the country, tireless volunteers are working day and night to rescue and re-home our vulnerable sissy and femboy population. These are just a few of the thousands of Facebook posts seeking placement for these special little angels.... shysteffie <333 fans>   Caption this dumb sissy baby!    6   2025-06-29  All captions welcome! Either leave a comment on a pic or message me the link to your caption! Littleuce <57 fans>   Advanced Cuck Ideas    24   2025-06-29  Hope you like these too coldsoup <356 fans>   French skinny sissy slut Taniass    30   2025-06-29  procurves <3 fans>   Pink lingerie tail and ears     11   2025-06-29  Serendipityxx <1,308 fans>   My Wife Turned Me Into A Sissy BBC Slut    30   2025-06-29  WhiteShuggah <85 fans>   Black pvc lingerie     34   2025-06-29  Serendipityxx <1,308 fans>   Aline Travestie (799)     20   2025-06-29  Aline travestie en lingerie et en cage aline_trav <1,458 fans>   Posing in my Prissy Sissy Princess French Maid Dress    25   2025-06-29  Posing in my pretty Prissy Sissy Princess French Maid Dress Maid_Teri <702 fans>   My grindr album:) DeeDee My new name.    27   2025-06-29  Cmos141 <303 fans>   Femdom Captions 72    4   2025-06-28  clthong2 <555 fans>   cindy_cross39 Favourites 1    14   2025-06-28  In no particular order - some of my favourite outfits of Cindy. leatherboi <154 fans>   Christine the AI fetish transvestite sex slave 5    24   2025-06-28  The continuing adventures of Christine and her boyfriend Garrett MoZoCo <37 fans>   Inside my head on June 28th    112   2025-06-28  What I’m thinking about today, lots of gay fantasies Myown <904 fans>   FionaRabbit Ruby Pearl    17   2025-06-28  Photoshop edits gallery for FionaRabbit using the Ruby Pearl action. CascadingSilen <1,234 fans>   Advanced Cuck Ideas    24   2025-06-28  Hope you like these too coldsoup <356 fans>   Sena Sissy Maid    6   2025-06-28  Pics of feminized Sena as a Sissy Maid. Caption and repost are welcome senna106288 <45 fans>   Blonde Sissy    276   2025-06-28  Snuskis80 <144 fans>   lolatoys sexy crossdresser LOVE en rose et noir    13   2025-06-28  lolatoys sexy crossdresser LOVE en rose et noir - ?? Et oui j'ai coupé mes cheveux pour cet été ???? je reviens avec une petite série de photo ???? ???????? ?????? bisouX ???? lolatoys <677 fans>   Sissy Julie Allison Lingerie: Black Teddy    22   2025-06-28  Sissy Julie Allison Lingerie: Black Lace and Sheer Teddy JulieAllison <607 fans>   Camo Pants    155   2025-06-28  Snuskis80 <144 fans>   Cuckold captions    31   2025-06-28  For the cuckold T_Dodo <1,505 fans>   Diaper Captions 172    8   2025-06-28  clthong2 <555 fans>   Silly Sissy In Panties And Diapers    34   2025-06-28  Embarrassing photos for a silly sissy. Rile-Rile <85 fans>   Sara Dream Sissy 14    5   2025-06-27  Gifs of me SaraDream <246 fans>   Sissy caption    1   2025-06-27  Caption of me made by me sissy_roberta <95 fans>   sissy    5   2025-06-27  slut sissy Theoporos <38 fans>   Sissy Captions 81    16   2025-06-27  Alyssa38b <1,909 fans>   Guilty of Being a Wimp so Sentenced to Sissy Sexual Servitude    24   2025-06-27  ENJOY FORCED FEMINIZATION AND SISSY HUMILIATION THEMES? - - Then check out my full-length stories at www.lulu.com/spotlight/candy_runt Candy_Runt <4,619 fans>   Gallery_201_My_hairy_cock_and_body_4    2   2025-06-27  Pictures of me, please comment freefriki <339 fans>   Gallery_200_My_sissy_gay_butt_3    2   2025-06-27  Pictures of me, please comment freefriki <339 fans>   My stroke buddy 2    9   2025-06-27  Annalena20 <124 fans>   Cock Only Fag Whore    10   2025-06-27  beta sissy fag radmilasissy chastity pussyfree radmilasissy <1,641 fans>   Inside my head. More and more thoughts    84   2025-06-26  I love big men, small cocks, black cocks, drinking cum, being forced to suck cock, drinking spunk, dressing like a sissy and being a gay fuck Myown <904 fans>   Seren new caps 340    12   2025-06-26  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 <1,235 fans>   SISSY GIF'S CAPTIONS-88    16   2025-06-26  kparc1212 <4,777 fans>   500th gallery special: How I was feminized     28   2025-06-26  Just over three years later, and we've reached 500 galleries! Wow! As usual, I'm publishing the corresponding special. This time, I'm recounting my feminization process (or how I'd like it to be, which is the same in this virtual universe). Toward the... sissystraight6 <2,550 fans>   A day in the life of a Sissy Whore (4)    28   2025-06-26  Hi friends! It's been a while since we last talked! Over a year, if I'm not mistaken. I'm still a prostitute, but I've left the streets and the car behind. Now I see clients at my home. But while I wait, I'm always excited just by the anticipation of... sissystraight6 <2,550 fans>   My Feminist Boss 19    24   2025-06-26  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 <2,907 fans>   just me and my absolute dumptruck x    1   2025-06-25  Just signed up because there's so few places that do like legit amateurs changing erotic pics with eachother. I'm yet another sissy (omggg like the handle so funny). I guess now she/her after 2 years hrt but like, I hate nothing more than the trans... yetanothersiss <46 fans>   Advanced Cuck Ideas    24   2025-06-25  Hope you Like coldsoup <356 fans>   Femdom Feminization Captions 6 (Chastity, Petplay, Pegging)    10   2025-06-25  cha0self <363 fans>   Andrea, tranny gurl outed for men and sissies    11   2025-06-25  Andrea's feminized dream greatlegs <1,025 fans>   Ex girlfriend caption 2    1   2025-06-25  She broke up with me probably with a real man now and not with a cock sucking sissy Faggot like me sissy_roberta <95 fans>   Panty Captions 52    10   2025-06-25  clthong2 <555 fans>   Cuckold Life Twenty One    24   2025-06-24  Cuckold family life jillian_silver <314 fans>   Sissy Captions - Encouragements 5    53   2025-06-24  Sissy Captions Sissy_Scarlett <1,438 fans>   CFNM Femdom Sissy Strapon    92   2025-06-24  Femdom sissy strapon pegging, CBT, spitroast, cock milking images. Mike32174 <538 fans>   Captions-Interracial Sissy GIF's - 16    16   2025-06-24  kparc1212 <4,777 fans>   Shemales and Fuckdolls AI    21   2025-06-24  These prissy fuckdolls know their place, as dolled up cock toys and breeding sluts for powerful shemales. spj2000 <412 fans>   Hentai Otokonoko no Dokidoki Campus Life. Artist: PenDD    33   2025-06-24  Just look at this little horny slut. I bet you want to be like her. I want! anonymous_vulg <383 fans>   Transvestite Academy 2. Artist: Butter Bunny    12   2025-06-24  anonymous_vulg <383 fans>   Transvestite Academy. Artist: Butter Bunny    12   2025-06-24  anonymous_vulg <383 fans>   Surprisingly body swap. Artist: Butter Bunny    12   2025-06-24  anonymous_vulg <383 fans>   Crossdressing Police Station. Artist: Butter Bunny    12   2025-06-24  anonymous_vulg <383 fans>   Become a Business Girl    12   2025-06-24  anonymous_vulg <383 fans>   Gallery_My_hairy_cock_and_foreskin_2    2   2025-06-24  Pictures of me, please comment freefriki <339 fans>   ItsNikkiNicole 2    28   2025-06-24  UK crossdresser / glam drag Goddess Nikki Nicole. One of the all time greats. Biggest hair, best outfits, makeup perfection. Find her socials everywhere @itsnikkinicole kinkchic91 <1,960 fans>   ItsNikkiNicole 1    43   2025-06-24  UK crossdresser / glam drag Goddess Nikki Nicole. One of the all time greats. Biggest hair, best outfits, makeup perfection. Find her socials everywhere @itsnikkinicole kinkchic91 <1,960 fans>   Aline Travestie (798)    20   2025-06-24  Aline travestie en lingerie aline_trav <1,458 fans>   RL Leopard    5   2025-06-24  raelynn98 <264 fans>   Sissy Maid Rehabilitation AI Images - Rehab Facilities    72   2025-06-24  AI generated images and captions inspired by FEMINYZE-CAPTIONS' better captions, about a fantasy dystopia where sissy maids are being taught and brainwashed at rehab facilities. ViennaSheraton <1,368 fans>   Femdom Feminization Captions 5 (Chastity, Petplay, Pegging)    10   2025-06-23  Femdom Feminization captions with no maledom. cha0self <363 fans>   Sissies in Bondage 14    20   2025-06-23  KarinaClarkeTV <832 fans>   Sissy Dezi exposed thick white slut    31   2025-06-23  Kik pinksissyeve or snap dezi_sissyreid Dezi_sissyreid <141 fans>   SISSY GIF'S CAPTIONS-87    16   2025-06-23  kparc1212 <4,777 fans>   Femdom Feminization Captions 4 (Chastity, Petplay, Pegging)    10   2025-06-23  Forced feminization captions, no maledom. cha0self <363 fans>   Red Suspender Tights, PVC Gloves     11   2025-06-23  Latex Hooded Nylon and PVC Crossdresser Cruising in the Woods TaraLovesCock <133 fans>   Pet play    18   2025-06-23  Probably one of my dirtiest sissy slave fantasies nylon cock <1,497 fans>   Gallery_199_My_sissy_gay_butt_2    2   2025-06-23  Pictures of me, please comment freefriki <339 fans>   Sissy Slut Sarah Simone ~ Exposed Forever Online    5   2025-06-23  THE INTERNET ~ Once you post it, it is on there forever. And you have no clue where it may end up. GoodGirlBambi <613 fans>   Diaper Captions 171    8   2025-06-23  clthong2 <555 fans>   The French Maid 90    37   2025-06-23  Posing in my pretty Sissy Maid dress Maid_Teri <702 fans>   RL No Panties    4   2025-06-23  raelynn98 <264 fans>   Redhead Sissy Kristina Ryder    13   2025-06-23  Sissy Kristina Ryder showing off SissyKristina <647 fans>   The pussy got drunk on milk and now she's acting all slutty    16   2025-06-22  Betalincel <111 fans>   Betasafe Censored Pornstars 12    100   2025-06-22  Censored pornstars for betasafe sissy bois. Jerk off to feet, high heels and bbc, loser. Simp to pixels of women and transsexuals that real men get to look at all the time. wesmantooth <782 fans>   BBC sissy oiled and ready for anal.     54   2025-06-22  Leave a mean comment! 🙂‍↔️😉 Sissysexdolslu <76 fans>   HOT GIF 1126    13   2025-06-22  samir50 <1,855 fans>   Online self torture    15   2025-06-22  Online self torture slavetvmaso <606 fans>   Cuckolding Gets Serious 9    22   2025-06-22  ohchristwhat <1,682 fans>   A very busy day...    28   2025-06-22  My Mistress Sophia trains me to be the best cum-loving whore I can be. But achieving this requires effort and dedication on my part. Perhaps if I satisfactorily fulfill my duty, she'll decide to give me my coveted tits... Here's an example of one of my... sissystraight6 <2,550 fans>   GOON 2    16   2025-06-22  Lucydd <878 fans>   Sissygasm in red harness and black cage    21   2025-06-22  ballaincage <851 fans>   Slutty josiedee     10   2025-06-22  Josiedee slutty pics Josiedee <242 fans>   GOON 1    17   2025-06-22  Lucydd <878 fans>   GOON 1.5 upload problem    13   2025-06-22  Lucydd <878 fans>   Sissy caption gallery (let me know how you like to be used)    23   2025-06-22  Let me know how much of a sissy you are and how you serve alpha cock Lucydd <878 fans>   Send Me anything     4   2025-06-22  DM me all your fucked up shit chaingang11 <493 fans>   CFNM Sissy Femdom Strapon    98   2025-06-22  Femdom sissy strapon pegging, CBT, spitroast, cock milking images. Mike32174 <538 fans>   Big fat ass oiled up and ready for anal. Oiled white sissy looki    48   2025-06-22  Sissysexdolslu <76 fans>   Pink Pill Captions    20   2025-06-21  Zedrick <788 fans>   Doggystyle - Pics 14    30   2025-06-21  Submissive position for these sexy shemales, and they love it......................................To the best of my ability, no images violate the forbidden list. If this gallery or an image disappears it's because it was removed due to an unforeseen... hleio <1,875 fans>   Sissy Julie Allison Costume: Sailor Girl    29   2025-06-21  Sissy Julie Allison Costume: Sailor Girl JulieAllison <607 fans>   Black Net Dress    298   2025-06-21  Snuskis80 <144 fans>   Mommy and my Bully 3    15   2025-06-21  ohchristwhat <1,682 fans>   Mommy and my Bully 2    13   2025-06-21  ohchristwhat <1,682 fans>   Sissies in Bondage GIFs 4    15   2025-06-21  KarinaClarkeTV <832 fans>   More pictures I like     42   2025-06-21  sissymaster202 <814 fans>   some gifs of me     9   2025-06-21  geosmit <196 fans>   Lady Michelle - the many faces of     47   2025-06-21  Lady Michelle is here for you. She wants you to fake her - She wants you to tribute her - She wants your cum all over her face! Please give her what she wants and needs if you had the chance what would you want to do to her, Comments always welcome! EmkayH <1,802 fans>   Master's Sissy Faggot Wife     1   2025-06-21  Finally prepared to accept my role as a trained, obedient, feminized sissy faggot wife to a Master tamis_demise <136 fans>   German Sissy Jacqueline Pussy Mix No. 2    114   2025-06-21  My asspussy for you, who would fuck me? German Tranny <4,392 fans>   Machine-fucked Sissy    10   2025-06-21  A silly sissy gets buttfucked by machine. Rile-Rile <85 fans>   Wearing One Piece Bathing Suit    13   2025-06-21  Girl bathing suits are made for cute femboys and can fit a small cute penis easily. chanhaven56 <67 fans>   Sissy gallery (seeing if this is a dead site)    11   2025-06-20  Lucydd <878 fans>   German Sissy Swimsuit Collection    30   2025-06-20  Alice8989 <115 fans>   Red Lingerie    145   2025-06-20  Snuskis80 <144 fans>   BE THE GIRL 3: CHOICE GAME FOR WOMEN or MEN WHO WANT TO BE    24   2025-06-20  hotnhard_29 <7,121 fans>   Sissy Captions 63    40   2025-06-20  Sissy Captions Sissy_Scarlett <1,438 fans>   STROKERS CHOICE GAME 378: YOU DECIDE WHO YOU FUCK AND HOW    100   2025-06-20  hotnhard_29 <7,121 fans>   Femdom Feminization Captions 3 (Chastity, Petplay, Pegging)    10   2025-06-20  No maledom cha0self <363 fans>   Sissy Schoolgirl BJ Tease    10   2025-06-20  Redheaded sissy school girl teases you and shows while practicing her cock sucking SissyKristina <647 fans>   Me - Putito con uniforme de cole 2    15   2025-06-20  BonaMari <76 fans>   MLG / Sissy captions 85 - Adult Baby Cucks X    30   2025-06-20  The ABC caps are usually the first batch to reach the arbitrary 30 cap limit I set myself. Can't imagine why they're so easy to write... Orokana_Shojo <1,073 fans>   MLG / Sissy captions 83 - Sissy Femdom POV    30   2025-06-20  I split these out from gallery 82 when I realized there was this whole sub-category of POV caps happening directly addressing the viewer. Orokana_Shojo <1,073 fans>   MLG / Sissy captions 82 - Sissy Cuck Femdom XI    30   2025-06-20  This is about a four month backlog of stuff. Enjoy! Orokana_Shojo <1,073 fans>   Verified Sissy Rae Lynn    8   2025-06-20  Had a little fun while taking my verification photo raelynn98 <264 fans>   Captions Sissy, Cuckold, Ballbusting, Domination 62    26   2025-06-20  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, like fix a typo. I hope you enjoy them; they are in this file it is because I did! redbird2991 <1,659 fans>   Green And Black    133   2025-06-20  Snuskis80 <144 fans>   Gallery_198_My_sissy_style_pink_shorts_jeeerk_and_cooock_10    4   2025-06-20  Pictures of me, please comment freefriki <339 fans>   Sissy Faggot Tami Practicing for COCK    4   2025-06-20  I'd like to think that sissy faggot tami is a natural, but she is out of practice and needs Master to train her properly. tamis_demise <136 fans>   Pink Pill Sissies     16   2025-06-19  Zedrick <788 fans>   Sissy Tartan Slut    166   2025-06-19  Snuskis80 <144 fans>   GoonerAudioLabs June 2025 Gooner/Sissy/Cuckold Captions    27   2025-06-19  Join the Patreon for access to exclusive gooning audio files!n GoonerAudioLab <633 fans>   Sissy Shona Kitty Cat    9   2025-06-19  I'm a sissy cat ShonaMeowCD <466 fans>   Gallery_My_hairy_cock_and_foreskin    2   2025-06-19  Pictures of me, please comment freefriki <339 fans>   Sissy maid 2    8   2025-06-19  Sissy maid to be humiliated elusivekitten8 <68 fans>   German Sissy Jacqueline Pussy Mix No. 1    102   2025-06-19  My asspussy for you, who would fuck me? German Tranny <4,392 fans>   Gallery_197_My_sissy_style_pink_shorts_9    2   2025-06-19  Pictures of me, please comment freefriki <339 fans>   Aline Travestie (797)    20   2025-06-19  Aline travestie en lingerie et en cage aline_trav <1,458 fans>   RL In Skirt 2    29   2025-06-18  raelynn98 <264 fans>   Me Cindy Cross crossdressing in silver snake print legging    5   2025-06-18  Me Cindy Cross crossdressing in a silver snake print legging and very high heel strap sandals. cindy_cross39 <1,668 fans> :: prev :: | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | :: next ::