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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 Displaying results for 'sissy' - View all videos for 'sissy'  Gallery Name   Images   Quality   Added    SiSSY CD SAMANTHA ReUP Gallery 1    30   2025-03-07  After multiple fan requests, I've re-upped some pics from my 'classic' galleries. I'm currently working on new outfits and getting things together. Please enjoy! I also love comments and input! SexySissySlutS <760 fans>   March Sissy GURLS Pt 2    60   2025-03-07  NaughtyNikki99 <659 fans>   Candi_Kneels Original Sissy Cuckold Crossdresser Caps 41    65   2025-03-07  Candy_Kneels <928 fans>   Sissys on Black Cocks    8   2025-03-07  Black men have a natural gift for turning white bois into sissy sluts jonblacker <5,948 fans>   Sissy Captions From Around the Internet for 03-07-2025    107   2025-03-07  nolabicd <831 fans>   Good Gurls Rehab - 15    16   2025-03-07  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 <1,949 fans>   SISSY TOONS - CAPTIONS - 6    16   2025-03-07  kparc1212 <4,765 fans>   sissy gifs and pix    48   2025-03-07  lickher <1,198 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics920.1    48   2025-03-07  395royc <5,624 fans>   FEMDOM ET SISSY MIX     37   2025-03-07  FRlopesoumis9 <160 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics920    24   2025-03-07  395royc <5,624 fans>   The Sissy Life Final Valentines And Xmas Issues ---- Fake Magazi    8   2025-03-07  these are the final few covers that will probably finish up the Sissy Life cover series .. i may still do the very rare special edition such as the Election Special but if i do anymore they will be few and far betweennas it stands the series is 145... SluttyZoe70 <285 fans>   The Sissy Life Halloween Issues --- Fake Magazine    12   2025-03-07  SluttyZoe70 <285 fans>   The Sissy Life Easter Issues --- Fake Magazine    12   2025-03-07  SluttyZoe70 <285 fans>   Sissy goals and inspirations    14   2025-03-07  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 <111 fans>   Chantellesissy - I want cock inside my sissy faggot ass    13   2025-03-07  I want cock inside my sissy faggot ass. I love to spread my hole for real men who enjoy fucking sissy whores like me subsissyfaggot <1,344 fans>   Sissy Captions From Around the Internet for 03-06-2025    145   2025-03-07  nolabicd <831 fans>   Sissy Maid Rehabilitation AI Images - Indoctrination 2    48   2025-03-07  AI generated images inspired by FEMINYZE-CAPTIONS' better captions about a fantasy dystopia where sissy maids being taught and brainwashed. More garbled text. ViennaSheraton <1,358 fans>   Sissy Sex 36    722   2025-03-07  northcarolinac <663 fans>   Informative Sissy Captions    18   2025-03-07  CagedScott <92 fans>   Sissy captions that speak to me 98    20   2025-03-07  Slinky_Gurl <2,791 fans>   Sissy Feminization Captions 105    50   2025-03-07  Bloodrise69 <4,720 fans>   SISSY - GIF'S CAPTIONS - 72    16   2025-03-06  kparc1212 <4,765 fans>   Humiliation, Cuckold, and Sissy Captions    16   2025-03-06  Some blackmail, sissy exposure, cuckold, and humiliation captions. sissyerica <547 fans>   The Great Shift Experiences - 19    31   2025-03-06  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 <1,949 fans>   Sissy Life    1   2025-03-06  Nudahuda <1 fans>   Exposing SissyJacqui    19   2025-03-06  GODDEIV <13 fans>   Hot Sissy Fun    5   2025-03-06  Rhodean <310 fans>   Angelinas feuchte Sissy    152   2025-03-06  angelina1969 <177 fans>   Sissy and Sluts Hooded     60   2025-03-06  sissymaster202 <802 fans>   sissy clothes     12   2025-03-06  somethinglazyb <11 fans>   Naughty in nylon!    50   2025-03-06  Luckily my sissy husband likes tights as much as I do, which is why he buys me so many! One of these days I'm gonna have to get him to do a new photoshoot; I'd love a tights album featuring just me! Vicky xx Exquisitepassi <1,375 fans>   Sissy / TV / Shemale / CD / Trans GIF's    1000   2025-03-06  AGirlNamedAman <2,910 fans>   Sissy Peppo    2   2025-03-06  bigot44 <496 fans>   Sissy Captions From Around the Internet for 03-05-2025    87   2025-03-06  nolabicd <831 fans>   Sissy Slut Chelsea Love-Starr     49   2025-03-06  Turning this bimbo sissy into a fully exposed WEB SLUT. She keeps backing out from full exposure. Let’s make sure that can never happen again. Xposer_69 <37 fans>   Exposed Sissy Slut Desiree!    126   2025-03-06  EXPOSED SISSY is it really If I am just putting up selfies of myself. I just spent a few hundred on my very first breast plate with nice silicone boobs desiyoung669 <236 fans>   so you want to be a sissy    190   2025-03-05  dilligaf340 <1,630 fans>   Sissy essentials    43   2025-03-05  lila-sweet <137 fans>   Sissy time!    6   2025-03-05  sissygurl169 <549 fans>   femboy toy, twink, sissy    5   2025-03-05  pinktwink <28 fans>   femboy sissy cd teen feet crossdress    15   2025-03-05  pinktwink <28 fans>   femboy feet, twink, sissy    3   2025-03-05  pinktwink <28 fans>   Sissy Feminization Captions 104    50   2025-03-05  Bloodrise69 <4,720 fans>   Free Sissy original caption from Patreon 13    11   2025-03-05  LDB <382 fans>   Sissy sasha    52   2025-03-05  starrreev <1,060 fans>   Emo boys are natural Sissy Goths (toons)    7   2025-03-05  Peel back the cover on an Emo boy and you'll find a little goth sissy fuck toy waiting to be trained. jonblacker <5,948 fans>   femboy twink sissy bussy feet cd    4   2025-03-05  pinktwink <28 fans>   SissySlutMarty the Public Big Booty Bimbo    5   2025-03-05  SissySlutMarty <365 fans>   Sissy plug and caged     16   2025-03-05  Pute à BBC Bitch119 <647 fans>   Sissy Feminization Captions 103    50   2025-03-05  Bloodrise69 <4,720 fans>   Sissy Feminization Captions 102    50   2025-03-05  Bloodrise69 <4,720 fans>   Sissy femboy cock    7   2025-03-05  spoiler71 <727 fans>   Mistress Sissy Caption 23    44   2025-03-04  Sissy_Scarlett <1,413 fans>   Pretty Sissy non nude mostly    14   2025-03-04  Dressed up in sexy feminine outfits, mostly non nude Trannybabe <1,226 fans>   Sissy Jaymie Cummings can't stop showing her sexy body    19   2025-03-04  Jaymie´s Kik: SissyWhiteBoy94 Sissylover1981 <1,402 fans>   German Sissy Fucktoy Becky Rose is ready to play    48   2025-03-04  Sissylover1981 <1,402 fans>   My original sissy caption (Happy Mardi Gras)    25   2025-03-04  nolabicd <831 fans>   SISSY - GIF'S CAPTIONS - 71 - TranniesCrossdressers    16   2025-03-04  This was Uploaded by kparc1212 Silverhaired_O <3,508 fans>   Sissy Captions From Around the Internet for Fat Tuesday    118   2025-03-04  nolabicd <831 fans>   SissyLina EXPOSED     55   2025-03-04  SissyLinaExpos <1 fans>   Sissy Feminization Captions 101    50   2025-03-04  Bloodrise69 <4,720 fans>   Sissy (ish) Captions gifs 01    25   2025-03-04  ImpureBlue <137 fans>   Sissy Captions From Around the Internet for 03-03-2025    107   2025-03-04  nolabicd <831 fans>   Sissy Hentai/Cartoon Captions    5   2025-03-04  FemSuzuya <6 fans>   Sissy caption gifs that speak to me 89    20   2025-03-03  Slinky_Gurl <2,791 fans>   Sissy Slut Mario is on display    7   2025-03-03  SamiSSIpresi <70 fans>   Sissy_Alisa    3   2025-03-03  AlisaSissy05 <2 fans>   SISSY - GIF'S CAPTIONS - 71    16   2025-03-03  kparc1212 <4,765 fans>   Captions Sissy, Cuckold, Ballbusting, Domination 55    21   2025-03-03  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 <1,649 fans>   Sissy Love AI    20   2025-03-03  Short stories of Sissies in love AI Florazul <910 fans>   Sissy Captions    29   2025-03-03  Sissy Captions NicoleBitch <413 fans>   chastity sissy    6   2025-03-03  hansen23 <124 fans>   Sissy slaves 39    52   2025-03-03  subsissy58y <628 fans>   Sissy and Sluts Bondage     119   2025-03-03  sissymaster202 <802 fans>   Femboy, Trans, Sissy    70   2025-03-03  trans mattmiak <2,043 fans>   Captions - Interracial Sissy Toons - 2    15   2025-03-02  kparc1212 <4,765 fans>   Sissy Captions 42    50   2025-03-02  Sissy Captions Sissy_Scarlett <1,413 fans>   My Sissy Cock    100   2025-03-02  Tilly1 <149 fans>   Sissy Captions From Around the Internet for 03-02-2025    91   2025-03-02  nolabicd <831 fans>   Sissy Stuff 4    30   2025-03-02  jh1776 <2,304 fans>   Sissy Trine slutty in pink    14   2025-03-02  Pink bunny outfit for a pink sissy slut. As a sissy I am public property. Repost me anywhere you want. trisette1 <837 fans>   Captions - Interracial Sissy Toons - 1    17   2025-03-02  kparc1212 <4,765 fans>   Sissy Karen    26   2025-03-02  starrreev <1,060 fans>   Samantha Fesselopfer Sissy Crossdresser Bondage 3    904   2025-03-02  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <772 fans>   sissy maid    2   2025-03-02  lanacera <24 fans>   Samantha Fesselopfer Sissy Crossdresser Bondage 2    985   2025-03-02  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <772 fans>   Sissy slaves 38    53   2025-03-02  subsissy58y <628 fans>   Sissy fag sluts who come out to their best friends    8   2025-03-02  When you confess to your oldest childhood friend that you like to dressing girl clothes most take it well ...and then make you take it well. jonblacker <5,948 fans>   Samantha Fesselopfer Sissy Crossdresser Bondage 1    916   2025-03-02  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <772 fans>   BEAUTIFUL SISSY BOY    10   2025-03-02  PAULROBERT801 <184 fans>   Betasafe Censored Pornstars 7    100   2025-03-01  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 <774 fans>   Sissy    15   2025-03-01  SexyBabyGurl <0 fans>   Sissy Slave Seira    58   2025-03-01  Seira was born in Thailand from a very poor family. At 18, Seira was sold to a wealthy Japanese businessman for money to do housework. What seemed like a work opportunity at first, became something else. Seira was given more opportunities to make money... FeminizationCo <114 fans>   Reluctant Sissy Captions 3    4   2025-03-01  Captions of sissy boys being reluctantly humiliated, dressing in women's clothing, being put back in diapers, and being in romantic situations with other men. snowwight <1,956 fans>   Sissy In Black Lingerie    129   2025-03-01  Snuskis80 <135 fans>   Censored Beta Loser Sissy Safe 06 - Keyholder Feet    19   2025-03-01  Stare at the chastity key and do not look anywhere else. Her beauty is for alpha men and their arousal. You do not deserve it. Your arousal comes from her control over you. Your pleasure comes from her extending your time in chastity. virginchastity <463 fans>   Sissy Chrissy is on display    3   2025-03-01  SamiSSIpresi <70 fans>   Fetish sissy posing 2    10   2025-03-01  Latex, PVC, heels and cuffs - all of sissy Bianca's favorite things PVClvr <262 fans>   Sissy captions that speak to me 97    20   2025-03-01  Slinky_Gurl <2,791 fans>   Sissy caption gifs that speak to me 88    20   2025-03-01  Slinky_Gurl <2,791 fans>   sissy captions 8    5   2025-03-01  ELSA53 <2,407 fans>   Sissy Role Models 69    27   2025-03-01  FrenchSissySam <2,849 fans>   Sissy Role Models 68    27   2025-03-01  FrenchSissySam <2,849 fans>   Global sissy Inspiration 108    24   2025-03-01  FrenchSissySam <2,849 fans>   Global sissy Inspiration 107    22   2025-03-01  FrenchSissySam <2,849 fans>   Global sissy Inspiration 106    22   2025-03-01  FrenchSissySam <2,849 fans>   Sissy Gurl Collectors Cards / Trading Cards    69   2025-03-01  Sissylover1981 <1,402 fans>   Sissy Vanessa 2025    53   2025-03-01  SissyVanessaBo <56 fans>   Sissyboi Jonny 2025    105   2025-03-01  SissyVanessaBo <56 fans>   Sissy Julie Allison Outfit: Jean Shorts    31   2025-03-01  Sissy Julie Allison Outfit: Denim Shorts JulieAllison <602 fans>   SISSY CAPTIONS 121: WMAF'D BRATS    8   2025-03-01  caption time! this set is... about... wmaf... wh-which, um, i-if you're not familiar with that lil... acronym... j-just refers to... relations... between... a-a white Man... and... a-an asian... Female... only i-in this case... th-the "females" are all... FEMINYZE-CAPTI <5,063 fans>   Sissy Saturday     17   2025-03-01  Sun Fun rock345 <2,586 fans>   Mature sissy dildo slut    80   2025-03-01  sissygiina <150 fans>   sissy femboy bbc cockslut exposed leash and collar sucking dildo    7   2025-03-01  adatheslut <678 fans>   My New Sissy Adventure    10   2025-03-01  junkjukny <357 fans>   Sissy Weichei Fesselopfer Sklavin Fickpuppe Knebelopfer 5    801   2025-02-28  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <772 fans>   Sissy Weichei Fesselopfer Sklavin Fickpuppe Knebelopfer 4    802   2025-02-28  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <772 fans>   Sissy Weichei Fesselopfer Sklavin Fickpuppe Knebelopfer 3    954   2025-02-28  Ich mag es wenn ich überwältigt und dominiert werde, ich liebe es dabei in Badeanzügen und Leggings gefesselt zu werden.Ich lasse mich auch gerne mit reichlich Lotion einschmieren, und ich mache fast alles wenn ich hilflos gefesselt bin.Gerne... Samantha_Fesse <772 fans>   March Sissy Gurls Pt1    60   2025-02-28  NaughtyNikki99 <659 fans>   GoonerAudioLabs March 2025 Gooner/Sissy/Cuckold Captions    25   2025-02-28  Join the Patreon for access to exclusive gooning audio files! GoonerAudioLab <629 fans>   Sissy Captions From Around the Internet for 02-28-2025    193   2025-02-28  nolabicd <831 fans>   UK Sissy new pics     9   2025-02-28  NWSissy <184 fans>   Bubble Butt_Sissy Raider    5   2025-02-28  Mrs_Robinson <517 fans>   Sissy captions that speak to me 96    20   2025-02-28  Slinky_Gurl <2,791 fans>   Psychologists who treat pathetic losers 23    24   2025-02-28  They say admitting it is the first step to recovery, only there's no recovery for you. Dominant female psychologists don't suffer pathetic, sissy, bitches. Dominant psychologists prefer not to waste their valuable time on beta wimps like you. They are... krista024 <2,892 fans>   SissyButt3216 (Tgirl/CD)    131   2025-02-28  Found on reddit: sissybutt3216 aliciat <10,325 fans>   Best of BBC Sissy Captions 41-50    50   2025-02-28  Bloodrise69 <4,720 fans>   Fat sissy cleavage 1    2   2025-02-28  missykoks43 <224 fans>   Sissy captions that speak to me 95 - chastity    20   2025-02-27  Slinky_Gurl <2,791 fans>   Raven Cunningham tranny femboy CD slut    15   2025-02-27  stupid slut femboy raven cunningham!! ntelegram is sissy_raven0 whoreraven <19 fans>   SISSY TOONS - CAPTIONS - 5    15   2025-02-27  kparc1212 <4,765 fans>   Atomic Heart Futa/Sissy/Femdom/TGTF Captions    19   2025-02-27  Gallary contains Atomic Heart art of Guys getting fucked by robot futa's and getting turned into robotic sex bots. Questionair <417 fans>   Cumslut Sissy Caption 43    45   2025-02-27  Cum-slut Sissy Caption Sissy_Scarlett <1,413 fans>   leather sissy    10   2025-02-27  boundinrubber2 <213 fans>   Sissy slaves 37    70   2025-02-27  subsissy58y <628 fans>   sissy chastity    12   2025-02-27  me ind chastity trying to have som fun hansen23 <124 fans>   Beta sissy shame 2    10   2025-02-27  pghpw1 <34 fans>   BBC sissy    6   2025-02-27  sissyslutpucke <530 fans>   Sissy caption gifs that speak to me 87    20   2025-02-27  Slinky_Gurl <2,791 fans>   Sissy (ish) captions pictures 02    27   2025-02-27  ImpureBlue <137 fans>   sissy x change - kirito ~ lost GGO chronicles [Chapter 8]    41   2025-02-27  hihi everyoneee, its been a hot minute since i've uploaded anything, so i hope you enjoy this big chapter on Kirito's advancement into feminization leannelustof <481 fans>   Sissy and Sluts     54   2025-02-27  sissymaster202 <802 fans>   sissy life    403   2025-02-27  life as a sisssy dilligaf340 <1,630 fans>   Sweet Slut Sissy Bella    29   2025-02-27  My darling Bella is such a sexy little sissy slut . . . I want to lick/suck/nibble every delicious inch of her amazing body. 💞 marvint1963 <3,781 fans>   Sexy crossdressing sissy in jeans and high heels.????    22   2025-02-27  Pippa_Heels <121 fans>   Sexy sissy in wetlook leggings and heels.????    24   2025-02-27  Pippa_Heels <121 fans> :: prev :: | 1 | ... | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | :: next ::