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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    Christine the AI fetish transvestite sex slave 2    24   2025-05-06  The continuing adventures of Christine and her boyfriend Garrett MoZoCo <37 fans>   QoS Lifestyle    27   2025-05-06  sissyjustinaxx <2,281 fans>   Cuckold ceremony making it official 34    24   2025-05-06  A new tradition of officially marking your cuckolding. The day after your wedding about 60% of the guests come back together for your cuckolding ceremony. The ceremony is an official recognition of your being a cuckold and your wife and you submitting... krista024 <2,905 fans>   Gallery_183_my_hairy_cock_relax_to_hard_A    6   2025-05-06  Pictures of me, please comment freefriki <339 fans>   Sissy in lingerie    7   2025-05-06  elusivekitten8 <68 fans>   Sissy Dannii naked ass may 25    8   2025-05-06  Back showing off and spreading my ass for all you big dicked alpha man to fantasise about giving a hard fucking OrLLin89 <637 fans>   Christine the AI fetish transvestite sex slave    24   2025-05-06  The adventures of Christine and her boyfriend Garrett MoZoCo <37 fans>   Kelly UK CD T:kellythekink    14   2025-05-06  I am such a sissy slut. Please say hello on Telegram if you want to fuck me. Kellythekink <384 fans>   ichirouta kazemaru blacked    12   2025-05-06  sissyhoon <2,272 fans>   Gallery_182_my_naked_body_cock_butt_10    5   2025-05-06  Pictures of me, please comment freefriki <339 fans>   Diaper Captions 164    5   2025-05-06  clthong2 <555 fans>   sissy school girl stockings 2025    45   2025-05-06  new may 2025 sissy school girl stockings lingerie dookieday <1,340 fans>   Who Wants To See Some Pathetic Sissy Bitches Humiliated    24   2025-05-05  FORCED TO FAG SISSY HUMILIATION STORIES at www.lulu.com/spotlight/candy_runtn Candy_Runt <4,614 fans>   SISSY GIF'S CAPTIONS-83    16   2025-05-05  kparc1212 <4,773 fans>   spriing cleaning     7   2025-05-05  JNovak8771 <61 fans>   Free Sissy original caption from Patreon 15    11   2025-05-05  LDB <383 fans>   Aline Travestie (788)    20   2025-05-05  Aline travestie en lingerie aline_trav <1,458 fans>   The French Maid 89    71   2025-05-05  Posing in my pretty Sissy Maid dress Maid_Teri <702 fans>   Sissy Tartan Outfit    234   2025-05-04  Snuskis80 <144 fans>   Zoe Montague: Vol 2.    100   2025-05-04  mrssmith2022 <1,553 fans>   Fuckability Factor    24   2025-05-04  Although it was her pretty little dick that first caught my attention, the femboy's incredibly high Fuckability Factor made me obsess about breeding her repeatedly. yfnsp <3,492 fans>   Sissy james and his Aunty Sue (toon) - 2    8   2025-05-04  Young james was sent to live this is Aunty Sue who told him his was far to pretty to be a boy and made him dress as a girl. (continues from "Sissy james and his Aunty Sue - 1" jonblacker <5,974 fans>   Sissy james and his Aunty Sue (Toon) - 1    8   2025-05-04  Young james was sent to live this is Aunty Sue who told him his was far to pretty to be a boy and made him dress as a girl. jonblacker <5,974 fans>   Femboys and Twinks    50   2025-05-04  rubberlover85 <1,375 fans>   Sissy in black pissing    7   2025-05-04  lido_up_2 <143 fans>   sissy gurl    5   2025-05-04  mistybeech39 <397 fans>   Sissy Slut Chelsea Love-Starr 2    13   2025-05-04  Let’s make this sissy slut famous Xposer_69 <37 fans>   Trapped in My Own Caps 2 - Neighbors    24   2025-05-04  Always take the time to get to know your neighbors. Except that weirdo tranny who makes bad porn captions. Avoid them. ViennaSheraton <1,367 fans>   White Heels    138   2025-05-03  Snuskis80 <144 fans>   Wife material? #16    17   2025-05-03  LaraLocke <3,237 fans>   Skinny Humiliated Sissy Slut    7   2025-05-03  slutty_qoshoe <39 fans>   Chastity Captions 2    4   2025-05-03  Newer captions, I think I've improved. Let me know what you think. sissysabrinach <31 fans>   Sissy Julie Allison Swimwear: Red Thong Bikini    31   2025-05-03  Sissy Julie Allison Swimwear: Red Thong Bikini JulieAllison <607 fans>   Gallery_181_my_hairy_cock_black_and_white    4   2025-05-03  Pictures of me, please comment freefriki <339 fans>   Sissy 8    20   2025-05-03  KarinaClarkeTV <829 fans>   Bifems TS 3    10   2025-05-03  sissyncaptionsnshemalentsncrossdressingn Bifems <925 fans>   Gallery_180_my_naked_body_cock_butt_9    6   2025-05-03  Pictures of me, please comment freefriki <339 fans>   Lollipop Dicks 13    88   2025-05-03  Dicks I would suck like a lollipop. I enjoy masturbating over comments on the Dicks in my galleries so please leave some Iwantdick67 <1,361 fans>   2025may sissy having fun    14   2025-05-03  my sissy side loves having pictures of my cum covered bottom and flashing my small cock dookieday <1,340 fans>   Sissy sophie no more going back,    23   2025-05-02  Sophieprettypo <253 fans>   Panty Sniffing Pervert Forced to Wear Them to Work Captions    24   2025-05-02  I needed to cum so badly I readily agreed to do anything she asked. And this is how I ended up becoming Rafiq’s sissy bride and community fuck doll! - - - If you enjoy forced feminization, plus interracial and female domination themes,... Candy_Runt <4,614 fans>   Sissy Pantyhose Caption 13    39   2025-05-02  Sissy Pantyhose Captions Sissy_Scarlett <1,437 fans>   Femodom Sissy Strapon Pics and Gifs    139   2025-05-02  Femdom sissy strapon pegging, CBT, spitroast, cock milking images. Mike32174 <536 fans>   redhead shemale monica m nude    21   2025-05-02  Monica M <695 fans>   Advanced Cuck Ideas    24   2025-05-02  Thanks of your interest and support coldsoup <353 fans>   Babysitters and Cuckoldsitters in Control 24    24   2025-05-02  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 <2,905 fans>   Feminine Inspiration: Feminine moves 04 - GIFs    24   2025-05-02  If you truly want to feel feminine and look feminine then you must learn how to move in a feminine way. Look and learn from the experts; they are all gorgeous women. LongstockingsM <859 fans>   Cuckold caps #14: cuckolds loving cum &amp; creampied wives    8   2025-05-02  Another series of cuck captions - cuckolds serving hotwives, cleaning up oozing cum from their wive's fucked pussies. Submissive men who love to lick creampied pussy. Femdom / Alpha wives controlling their hubbies. nnWould love your comments! PMs and... LHB <458 fans>   Sub Sissy Slut 04    10   2025-05-02  Saw my order was delivered. Skipped out of work at lunch so i could try on my new panties and play with my new toy. got a few more things for saturday...gonna get wild. TinyDickCreepe <483 fans>   Gay Sissy Femboy Faggot DeviantSissy 2    10   2025-05-02  Having a little more fun showing off my silly little dickie and big hungry booty.. DeviantSissy <2,355 fans>   MySissyFavs    86   2025-05-02  A random collection of some of my favorite sissy images from around the net. (Please check back, I will be adding to this collection from time to time)nnI DO NOT OWN THE RIGHTS TO ANY OF THESE IMAGES! ALL PEOPLE IN THE IMAGES ARE 18 nnIf anyone wishes... S_Millie <110 fans>   Sissy Test - 3    9   2025-05-01  How are you progressing on your journey to becoming a supper sissy? Are you getting there or are you being a bad little sissy slut? We will find out in this scientific test! Cum_On_Ash <482 fans>   My Mommy is Brads Whore 20    16   2025-05-01  Inspired by "Brad the Bully Seduces my Mom". It is a story about a weak sissy and his slutty bimbo mom, Becky. They are both used and abused by Brad... Brad bullies sissy in school and turns Becky into his private whore... Sissy is a virgin, but he... CaptionedSissy <2,044 fans>   Blackmailed into Wearing Panties to Suck Another Mans Cock    24   2025-05-01  Finally! I have uploaded three spanking new stories involving a spineless straight guy who is unable to stop others from bullying him into serving as their sissy sex bitch! His inability to stand up to his bullies, leads to all manner of deeply... Candy_Runt <4,614 fans>   Advanced Cuck Ideas    24   2025-05-01  Hope you like coldsoup <353 fans>   Sissy sophie morning slut    23   2025-05-01  Sophieprettypo <253 fans>   Sissies in Bondage 13    20   2025-05-01  KarinaClarkeTV <829 fans>   Crossdresser and Sissy Pegging 7    20   2025-05-01  KarinaClarkeTV <829 fans>   Amateur sissy in new outfits    14   2025-05-01  I found a few new things I could wear even though I didn’t have a lot to make much of an outfit I think I did pretty welll and had some fun ;) Charmstheshell <246 fans>   Sissy faggot Roberta captions     2   2025-05-01  sissy_roberta <95 fans>   GoonerAudioLabs May 2025 Gooner/Sissy/Cuckold Captions    29   2025-05-01  Join the Patreon for access to exclusive gooning audio files! GoonerAudioLab <633 fans>   Femdom Captions 67    7   2025-05-01  clthong2 <555 fans>   total sissy     5   2025-05-01  Failed as a man, become a Sissy mistybeech39 <397 fans>   New Me (Sissy Story)    4   2025-04-30  It's finally time to turn your life around, no more being a sissy cumdump for massive cocks Voxelmage <306 fans>   Chloe moretz is a princess. We are pathetic losers    4   2025-04-30  Yes my princess, i can jerk off for hours to videos of you being interviewed emmawatsonssla <2,360 fans>   SISSY GIF'S CAPTIONS-82    16   2025-04-30  kparc1212 <4,773 fans>   Story of Dick Slave - Whiteboi Colonization    7   2025-04-30  The syllabus requires a thorough lesson on the effects of Black physiology on white males. Dick Slave generously welcomes Master Daimon and selects Casey Winterson to have the privilege of being the practical example. Things may seem rough and intense,... MarquisdeDom <148 fans>   Aline Travestie (787)    20   2025-04-30  Aline travestie en lingerie et en cage aline_trav <1,458 fans>   sissy used fucked in kitchen    22   2025-04-30  sissy with small cock after being fucked and cum on by 2 alpha men dookieday <1,340 fans>   sissy cum on small cock april 2025    26   2025-04-30  april 2025 used fucked cum on sissy tranny before after being fucked dookieday <1,340 fans>   sissy school girl april2025    42   2025-04-29  sissy school girl fucked cum on small cock stockings dookieday <1,340 fans>   Daughters and Mothers In Control 51    24   2025-04-29  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 <2,905 fans>   Sissy Niall Exposed     3   2025-04-29  Sissy Niall Exposed a new sissy i have found to use dansissies <93 fans>   Seren new caps 336    12   2025-04-29  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>   Downage (Sissy Story)    3   2025-04-29  Your internet went down while your roommate was in the middle of jerking off, now he needs help getting his nut out Voxelmage <306 fans>   Sissy Cuckolds 39.    320   2025-04-29  sissycarla49 <2,389 fans>   Femdom Captions 66    5   2025-04-29  clthong2 <555 fans>   Forcibly Feminized, Publicly Abused and Humiliated Sissy Caption    24   2025-04-28  If, like me, you’re fascinated by the themes of forced feminization and sissy humiliation, you could do a lot worse than check out my seven full-length stories on these very subjects! They cost the same as a fancy coffee and are available,... Candy_Runt <4,614 fans>   Sissy sophie no return    23   2025-04-28  Sissy sophie Sophieprettypo <253 fans>   Sissy2    21   2025-04-28  Betalincel <110 fans>   Feminine Inspiration: Feminine moves 03 - GIFS    24   2025-04-28  If you truly want to feel feminine and look feminine then you must learn how to move in a feminine way. Look and learn from the experts; they are all gorgeous women. LongstockingsM <859 fans>   SISSY GIF'S CAPTIONS-81    12   2025-04-28  kparc1212 <4,773 fans>   Diaper Captions 163    8   2025-04-28  clthong2 <555 fans>   Advanced Cuck Ideas    24   2025-04-27  Many thanks for all your support and interest coldsoup <353 fans>   paddlecakes 011 - plaid skirt sissy packed with Big Black Toy    22   2025-04-27  paddlecakes <1,815 fans>   I'm trying to seems more girly. Red and White stocking edition.    11   2025-04-27  I wish I were a girl with two holes. But I only have one and I abuse of it. swollen_man_cu <521 fans>   tail plug    7   2025-04-27  sweetbumhole <443 fans>   cute whore🖤    15   2025-04-27  sweetbumhole <443 fans>   Blue And White    128   2025-04-27  Snuskis80 <144 fans>   i could be an alfa man with this small cock???    79   2025-04-26  sissy chastity amateur trans vikini dildo sissygigiolidi <185 fans>   Babe-cock flash cards 22    50   2025-04-26  Giddy girls will shame you and reprogram you with big cocks. Ladies greedily sucking dicks will teach you to feel jealous for cock. Resistance is futile! Aikira <1,703 fans>   College Girlfriends [3D, sissification, uncensored]    153   2025-04-26  qnd84 <1,879 fans>   Sissy Captions 51    41   2025-04-26  Sissy Captions Sissy_Scarlett <1,437 fans>   Sissy sophie have a little accident     15   2025-04-26  Sissy sophie Sophieprettypo <253 fans>   Cages and Cock Rings    20   2025-04-26  I think I might have an addiction. I love wearing cages and Cock Rings, and I feel like I can never have enough. Wearing a small cage with a big plug (photos of that collection coming soon), feels so right it's scary. JudithCD <1,847 fans>   Sissy sophie favorite caption    12   2025-04-26  Sissy sophie webslut exposed Sophieprettypo <253 fans>   Sissy sophie webslut caption    32   2025-04-26  Sissy Sophie love to be exposed Sophieprettypo <253 fans>   Sissy Julie Allison Lingerie: Mint Teddy    29   2025-04-26  Sissy Julie Allison Lingerie: Mint Lace Teddy JulieAllison <607 fans>   Sissy Dezi exposed beta slut    13   2025-04-26  Dezi_sissyreid <141 fans>   Feminized Exposed in Pink Playtex Bra and Panties     1   2025-04-26  SissySonya <120 fans>   Prison Diary [3D, mtf/sissy, feminization, uncensored]    41   2025-04-26  qnd84 <1,879 fans>   AoA - Vile Villagers: Part 4 [Sissy, Captions, AI]     10   2025-04-25  Adventures of Alexa - Sissy Caption Stories. AI-Images by Lorena4u. AlexaRider2517 <191 fans>   BBC captions 4 - Hotel Adventures Two    11   2025-04-25  Your girl has been going out a lot more, and coming home smelling like the musk of other men. There's nothing you can do about it now...she's never going back to the way things were before she discovered dominant bulls who command her in the bedroom... bigburritoco <291 fans>   CD - Trans - Shemale - Mix - 8    30   2025-04-25  Mixed Gallery Jane-cd1968 <589 fans>   Advanced Cuck Ideas    24   2025-04-25  Many thanks for all who support and follow!! coldsoup <353 fans>   sissy abdl     48   2025-04-25  im sissy abdl lookin for a daddy sissygigiolidi <185 fans>   Sissy Captions - The Bully    35   2025-04-25  Sissy Captions - The Bully Sissy_Scarlett <1,437 fans>   AoA - Vile Villagers: Part 3 [Sissy, Captions, AI]    9   2025-04-25  Adventures of Alexa - Sissy Caption Stories. AI-Images by Lorena4u. AlexaRider2517 <191 fans>   Gallery_178_my_naked_body_cock_butt_8    5   2025-04-25  Pictures of me, please comment freefriki <339 fans>   TeasAndDenial Femdom Captions 58 (Sissy/Cuckold/Chastity)    12   2025-04-25  Another gallery of my original chastity captions x TeasAndDenial <4,082 fans>   AoA - Vile Villagers: Part 2 [Sissy, Captions, AI]     7   2025-04-25  Adventures of Alexa - Sissy Caption Stories. AI-Images by Lorena4u. AlexaRider2517 <191 fans>   Sissy Captions I Like VII    152   2025-04-25  desiyoung669 <238 fans>   Aline Travestie (786)    20   2025-04-25  Aline travestie en lingerie aline_trav <1,458 fans>   SEXY WHITE SISSY FOR BBC     24   2025-04-24  trapqueen69 <1,527 fans>   Have fun looking/comment    13   2025-04-24  delicious57 <138 fans>   i wish i was born a girl T_T    15   2025-04-24  geosmit <195 fans>   Fuck/cum my own ass    17   2025-04-24  I love to fuck my own ass and cumnTribute if u want Dotatul999 <148 fans>   Sissy after being used and facialized by real men    18   2025-04-24  Worthless sissy exposed after being used and destroyed by real men. Expose this stupid faggot gotya1011918 <13 fans>   Sissy exposed drinking 60 loads of cum    7   2025-04-24  Sissy faggot exposed drinking 60 loads of cum gokkun gotya1011918 <13 fans>   AoA - Vile Villagers: Part 1 [Sissy, Captions, AI]    8   2025-04-23  Adventures of Alexa - Sissy Caption Stories. AI-Images by Lorena4u. AlexaRider2517 <191 fans>   Catboy Sucking Dick    10   2025-04-23  CD femboy sucking cock and exposing my small cock that needs sucking. chanhaven56 <67 fans>   Sissy diary_4    100   2025-04-23  I've collected these images from various sources, including Imagefap. They illustrate my feelings towards femininity, and are also a source of inspiration for my queer transition as a nonbinary transfemme. Enjoy them! WreckedWhore <120 fans>   Advanced Cuck Ideas    24   2025-04-23  Hope you lall the pics people have offered coldsoup <353 fans>   Sissy caption: part V    24   2025-04-23  Gloriafrenchsi <809 fans>   Sissy 32    16   2025-04-23  Boys and young men turned into gorgeous women viktrig <472 fans>   Seren new caps 335    12   2025-04-23  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>   Me    4   2025-04-23  HornynTribute me if u like Dotatul999 <148 fans>   Sissy diary_3    100   2025-04-23  I've collected these images from various sources, including Imagefap. They illustrate my feelings towards femininity, and are also a source of inspiration for my queer transition as a nonbinary transfemme. Enjoy them! WreckedWhore <120 fans>   Sissy sophie want to be exposed    23   2025-04-22  Sissy exposed Sophieprettypo <253 fans>   Sissy Diaper Boy Humiliation     20   2025-04-22  Feel free to use this Humiliating pictures of me in any captions or reposts you want to create 🥰🫣 Sissyytboi <332 fans>   Ararity    76   2025-04-22  DErnest <716 fans>   Andrea, trans woman exposed    9   2025-04-22  She's walking with more of a wiggle greatlegs <1,025 fans>   Some favourites 3    73   2025-04-22  sissisubboy <1,344 fans>   Sissy Captions 50    45   2025-04-22  Sissy Captions Sissy_Scarlett <1,437 fans>   You're Nothing But a Loser 129    24   2025-04-22  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 <2,905 fans>   Other Gender Transformations - 17    23   2025-04-22  Various gender transformation captions which don't fit into my other categories. Includes: male to female, body swap, sex change, mtf, bra, sissy, body part swap, armor, medieval, animal, bride, cleavage, man boobs, christmas, wish, curse, dragon... rickbennett <1,954 fans>   Sissy and Feminization Captions 41: Pansies in Peril 6    20   2025-04-22  Even more trapped traps? Crossdressers in captivity? Tortured transvestites? Drag queens in dungeons? (Not much.) Bossed bound beta bois? Human-trafficked trannies? ViennaSheraton <1,367 fans>   My Fagina    18   2025-04-22  So happy I’ve made it to this stage in my training :) Thanks for inviting me into the fagina club! Kara_Anonon <172 fans>   Advanced Cuck Ideas    24   2025-04-21  Hope you like these coldsoup <353 fans>   SISSY GIF'S CAPTIONS-80 -Anal - Rough    16   2025-04-21  kparc1212 <4,773 fans>   Cuckold Life Fifteen    24   2025-04-21  Another life slice of family cuckolding jillian_silver <313 fans>   Feel cute ????     21   2025-04-21  Middle aged white guy with a small penis who like to show off and feel feminine in ladies lingerie. Sadbuttrue4_5 <32 fans>   BBC Captions 2    15   2025-04-20  Fresh original snowbunny/BBC content uploaded all the time - Check out my Patreon of wild exclusives related to your interracial fantasies. - n--patreon.com/BigBurritoCo- bigburritoco <291 fans>   Easter dress up!     16   2025-04-20  Just me and some sexy lingerie Charmstheshell <246 fans>   Sissy1    15   2025-04-20  Betalincel <110 fans>   Good Sissy Faggots 18    16   2025-04-20  CaptionedSissy <2,044 fans>   SISSY GIF'S CAPTIONS-79     16   2025-04-20  kparc1212 <4,773 fans>   Pantyhose Sissy Therapy Captions 2    24   2025-04-20  Not the Therapists. It takes a village SissyPHTights <674 fans>   Pantyhose Sissy Therapy Captions 1    24   2025-04-20  Meet the Therapists who treat Pantyhose Sissies SissyPHTights <674 fans>   Sissy captions from the web (4)    111   2025-04-20  Torridor <1,900 fans> :: prev :: | 1 | ... | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | :: next ::