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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    Urinella Sissy Slut Bikini Posing    28   2025-04-13  The_Sissy_Hunt <1,496 fans>   Sissy captions that speak to me - 103 pills etc    20   2025-04-13  Slinky_Gurl <2,791 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics929    24   2025-04-13  395royc <5,623 fans>   Sissy Stuffing     3   2025-04-13  Fill my Pussy rock345 <2,585 fans>   sissy situations and outfits    359   2025-04-13  some cute outfits and some sissy sex dilligaf340 <1,630 fans>   Sissy Short Stories #2    7   2025-04-13  Realmandingo94 <506 fans>   VickD Caged Bisexual Sissy Faggot     6   2025-04-13  VickyD <8 fans>   Amazing UK Sissy Slut Aimee    68   2025-04-13  In her own words "Hiya I'm Aimee a 21 year old sissy from the united kingdom. I'm still in the closet but I love online attention and exposure." marvint1963 <3,779 fans>   sissy in chastity    16   2025-04-13  chasted1974 <4,096 fans>   Assorted Sluts 42    45   2025-04-13  Photo dump of assorted sluts. Tasty teens, big titty fuck meat, and limp clit sissy sluts. Rate and comment your favorites. TinyDickCreepe <481 fans>   Sissy Traps 1    43   2025-04-13  playtex99 <276 fans>   Sub Sissy Slut 03    9   2025-04-13  Wrecking my nipples and teasing my tiny clit. I love these panties with the cute heart rings. You can violate my body, but please don't rip them off. TinyDickCreepe <481 fans>   Etre une bonne sissy 79    24   2025-04-13  gif gifs caption sissi sissy mistress french sissy femdom cd ts travesti crossdress crossdressing mistress madame humiliated humiliation dressage training rules feminised feminized feminisation loser cuckold focus pathetic crossdress06 laure loser... crossdress06 <3,545 fans>   teen sissy femboy slut in latex outfit and collar and panties    12   2025-04-13  adatheslut <678 fans>   BBC Love White Sissies    1000   2025-04-12  in real world, all fantasy aside truth is everyone just wants to feel good, most people dunt wanna be hurt or forced to do anything cept in roleplay or those very xperienced. so please eberyone remember to be kind to each other an make love not actual... ShyLonelyVirgi <1,237 fans>   Sissy Drogen Bondage Fesselopfer zum dauerficken und knebeln. 2    829   2025-04-12  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 Cocksluts Captions -Template made by TanyaKane-    7   2025-04-12  Sissylover1981 <1,401 fans>   Sissy Magazine Covers -Template made by TanyaKane-     31   2025-04-12  Sissylover1981 <1,401 fans>   SISSY CAPS    24   2025-04-12  hotnhard_29 <7,090 fans>   STROKERS CHOICE 375: ALL FANTASY ANYTHING GOES STR8 BI SISSY    47   2025-04-12  hotnhard_29 <7,090 fans>   STROKERS CHOICE 374: BI SISSY BIG COCK FEMDOM CUCK    48   2025-04-12  hotnhard_29 <7,090 fans>   Sissy In Leggings    116   2025-04-12  Snuskis80 <135 fans>   Sissy Nerd Micki    12   2025-04-12  Nerdy little sissy Micki loves to pose and loves to suck dick! Micknude <206 fans>   Mistress Sissy Caption 24    47   2025-04-12  mistressnsubmissionnfeminizationncaptionsnsissynslutnblowjobnanalnoralngloryhole Sissy_Scarlett <1,411 fans>   Some sissy, cuckold, crossdresser, loser beta captions    6   2025-04-12  sissyerica <547 fans>   My sissy life 3    5   2025-04-12  ELSA53 <2,406 fans>   Hot, Sexy Sissy Kandi    13   2025-04-12  This sweet sissy slut is SO fucking hot . . . almost made me cum in my pants just looking at her. 💞 marvint1963 <3,779 fans>   Sissy 31    25   2025-04-12  Yet more sissies, willing or not viktrig <468 fans>   My limp sissy clit, only good for serving BBC.     17   2025-04-12  bbccumslut911 <58 fans>   Sissy Story Drunk Brother    7   2025-04-12  Realmandingo94 <506 fans>   Sissy Oath, &ldquo;Any Cock, Anywhere, Any Time!&rdquo;    40   2025-04-12  cherrylipsbaby <11,986 fans>   AI Sissy 7    41   2025-04-12  lilllkittytrap <2,753 fans>   Sissy in micro chastity     4   2025-04-12  sexilexi1995 <27 fans>   Sissy captions that speak to me - 102    20   2025-04-12  Slinky_Gurl <2,791 fans>   sissy "cattrixxx" on kik    14   2025-04-12  Niwur <8 fans>   Gay sissy    17   2025-04-12  Sissytinycucky <545 fans>   Sissy incest caption gifs 2    12   2025-04-12  Converted my last set of captions to gifs in a batch so the quality was shit but I had already deleted the original captioned vids before I posted and checked the finished gifs lmao. I got annoyed and made these as replacements Jrok1234a <45 fans>   Captions Sissy, Cuckold, Ballbusting, Domination 57    21   2025-04-12  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 Julie Allison Dress: Black Cutout    22   2025-04-12  Sissy Julie Allison Dress: Long Black Cutout Dress JulieAllison <602 fans>   Sissy Scarlett Angel Exposed     7   2025-04-12  SissyScarlettA <9 fans>   How Sissys should be used 2    24   2025-04-12  Swiss_Sissy <387 fans>   Sissy and Slut Pigs     57   2025-04-12  sissymaster202 <801 fans>   April Sissy Gurls Pt 2    60   2025-04-12  NaughtyNikki99 <659 fans>   Sissy Bitch Poses April 2025    52   2025-04-12  Sissy crossdresser poses sandracduk <683 fans>   vacuuming is sissy work    15   2025-04-12  nacktsklave <2,210 fans>   Sissy Siblings #2    6   2025-04-12  Realmandingo94 <506 fans>   Sissy me ?    9   2025-04-11  Edjaguar <297 fans>   Pink Panty Cum    12   2025-04-11  Last weekend I caught up with another sissy. We fucked for hours, so I have been too horny to lock myself up again. Just before I could say goodbye to my week without wearing a cage. I thought I'd have one last play, ended up cumming on the floor like... Caged_Gab <397 fans>   Daddy Dom for Sissy Caps    16   2025-04-11  patchthrow <243 fans>   Blackmailed - Feminized - Humiliated - Furcked! Sissy Captions    24   2025-04-11  Candy_Runt <4,571 fans>   Sissy Caro Meier    6   2025-04-11  Sissy Caro Meier feminized and humiliated by their ex-gf/mistress! MasterE7 <678 fans>   SissySlutMarty is Excited to See You     3   2025-04-11  SissySlutMarty <365 fans>   Sissy Chastity    22   2025-04-11  hansen23 <124 fans>   Sissy Chastity    22   2025-04-11  hansen23 <124 fans>   A Few Vintage Sissy Photos    10   2025-04-11  Grisgris <4,801 fans>   19 Wisconsin sissy    5   2025-04-11  poids <364 fans>   Psychologists who treat pathetic losers 24    24   2025-04-11  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>   Sissy caption gifs that speak to me 95    20   2025-04-11  Slinky_Gurl <2,791 fans>   Crossdressing sissy - losing my panties    6   2025-04-11  Dressed and ending up losing my panties on all fours. sissy panties skirt crossdressing ass femboy socks legs cock clit plug doggy butt crossdresser amateur slut pet lylyoko <171 fans>   Sissy VickyD    6   2025-04-11  VickyD <8 fans>   1 - Sissy Joyce    37   2025-04-11  lopettedu11 <83 fans>   I'm a sissy cat, Meow    10   2025-04-11  I'm a sluty catgirl ShonaMeowCD <464 fans>   Sissy Collection Cards    19   2025-04-11  My Collection of Sissy Cards. Feel free to message me if you want to be added and I'll judge whether your pics are good enough to be added. If you want it down, message me here and I'll handle it. nnBe sure to collect them all! JamesHereToday <112 fans>   Sissy Jacqueline comes home and get horny PART II    44   2025-04-11  German Tranny <4,367 fans>   Sissy Jacqueline comes home and get horny PART I    18   2025-04-11  German Tranny <4,367 fans>   Sissygasm Captions 39    50   2025-04-11  Bloodrise69 <4,720 fans>   HOW I WOULD LOVE TO BE TREATED AS A SISSY.     50   2025-04-11  Sissyformommya <827 fans>   Daddy cock BBC sissy love 8    48   2025-04-11  Sissy loves big cock, loves to feel Daddy's power. Become the sissy slut for Alpha and his friends. Your comments are welcome. stantonz <4,947 fans>   Asian Sissy - Caged, Plugged and Shaven for Daddie's Fat Cock    6   2025-04-11  Hi everyone! I would just like to post myself all smooth and hairless ready to get pounded by some fat dicks!!! Secretsissy696 <44 fans>   dogsissywhore    5   2025-04-11  dogsissywhore <0 fans>   Sissy Captions 48    50   2025-04-10  Sissy Captions Sissy_Scarlett <1,411 fans>   SissySlutMarty Needs Your Cum    3   2025-04-10  SissySlutMarty <365 fans>   Sissy Magazine Covers featuring Henrietta (made by Sissy Chloe)    5   2025-04-10  These Covers and Captions were made by Sissy Chloe. Link to Chloes profile: www.imagefap.com/profile/SweetChloe Sissylover1981 <1,401 fans>   My Certificate of sissification academy    1   2025-04-10  During my training as a sissy, I adopted the sissy name Maddy Limp. squirts <677 fans>   Sissy Role Models 70    38   2025-04-10  FrenchSissySam <2,849 fans>   Global sissy Inspiration 112    33   2025-04-10  FrenchSissySam <2,849 fans>   Global sissy Inspiration 111    33   2025-04-10  FrenchSissySam <2,849 fans>   Blackmailed into Serving as his Sissy Bitch - Captions    24   2025-04-10  Candy_Runt <4,571 fans>   Sissy Svenja Exposed 8 Captions made by Caption_Maker    3   2025-04-10  Sissy Svenja Captions made by Caption_Maker Exposing-Sissy <243 fans>   Sissy Svenja Exposed 7 Captions made by shooterbob    5   2025-04-10  Sissy Svenja Captions made by shooterbob Exposing-Sissy <243 fans>   divers sissy 3    324   2025-04-10  sissytoy-fr <418 fans>   divers sissy 2    136   2025-04-10  sissytoy-fr <418 fans>   Tenues pour sissy    55   2025-04-10  sissytoy-fr <418 fans>   sissy &amp; wife    64   2025-04-10  sissytoy-fr <418 fans>   Sissy big ass for black cock    5   2025-04-10  Big ass white for BBC Bitch119 <647 fans>   Sissy Short Stories #1    8   2025-04-10  Realmandingo94 <506 fans>   Alpha BBC VS Beta sissy    204   2025-04-10  sissytoy-fr <418 fans>   Salope sissy for blacks cocks    20   2025-04-10  Gros cul blanc pour les blacks bien montés Bitch119 <647 fans>   Sissy Jacqueline Outdoor Flash Pee Blowjob    26   2025-04-10  German Tranny <4,367 fans>   Hazel Tucker Dream Gurl Sissy    53   2025-04-10  I guess I feel compelled to make this gallery. Last night I had a dream about Hazel, she was my brand new gurlfriend. We were going to see a movie together, and she started asking me if I had ever gone to a movie before when I was really really horny,... cherrylipsbaby <11,986 fans>   chastity &amp; sissy cage    184   2025-04-10  sissytoy-fr <418 fans>   Sissy joyce    70   2025-04-09  sissytoy-fr <418 fans>   Exposing my sissy feet just for fun     4   2025-04-09  I really like that deep blue color troip <664 fans>   GoonerAudioLabs 2025 Q1 Gooner/Sissy/Cuckold Captions    7   2025-04-09  Join the Patreon for access to exclusive gooning audio files! GoonerAudioLab <629 fans>   Fishnet sissy piggy    8   2025-04-09  PalmMuted <65 fans>   Pink piggy sissy    7   2025-04-09  PalmMuted <65 fans>   AI Pink Sissy    8   2025-04-09  JoeDingDong <55 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics928    24   2025-04-09  395royc <5,623 fans>   Exposing-Sissy-Svenja a sissy whore    3   2025-04-09  Exposing-Sissy-Svenja a sissy slut to use spread around shooterbob <788 fans>   Sissy Robyn    12   2025-04-09  SweetChloe <30 fans>   Interracial Sissy Adventure    38   2025-04-09  You meet some black friends with a giant cock and they want to fuck you... davidasissy <662 fans>   Rus sissy faggot 45    51   2025-04-09  Gimnast <1,545 fans>   sissy Asiacream    31   2025-04-09  Asiacream2077 <8 fans>   Sissy Sandra    21   2025-04-09  manu_1970 <578 fans>   Swim Team Sissy Fag    16   2025-04-08  Final say on whether I can hang out at swimming training depends on the coach and after seeing my tiny caged cock she agrees to let me pay to do so WannaBFag <182 fans>   Sissy Vicky Vicks black mini white top    15   2025-04-08  vicky_vicks <329 fans>   Sissyslut Kayla    51   2025-04-08  sissytoy-fr <418 fans>   Sissyjenna27    28   2025-04-08  sissytoy-fr <418 fans>   SissyFrancis74    29   2025-04-08  sissytoy-fr <418 fans>   sissy bella 2    44   2025-04-08  sissytoy-fr <418 fans>   Sissy Captions 47    44   2025-04-08  Sissy Captions Sissy_Scarlett <1,411 fans>   Sissy Perry Pupo Subfagperry Exposed Faggot Old Pics    67   2025-04-08  spokanefagperr <131 fans>   Requests for JoannaB4    16   2025-04-08  Captions for JoannaB4 using their pics and suggestions. Expose the sissy some more, imagefap.com/profile/JoannaB4 InsertHere99 <2,460 fans>   Sissy Captions From Around the Internet for 04-08-2025    88   2025-04-08  nolabicd <830 fans>   SISSY GIF'S CAPTIONS-78 - Submission     16   2025-04-08  kparc1212 <4,761 fans>   Sissy Tara spent her day Hosting!    24   2025-04-08  Just spent an afternoon hosting in my hotel room and wanted to catch my afterglow from a very good session! SissySSBBWLove <1,730 fans>   Free Sissy original caption from Patreon 14    11   2025-04-08  LDB <382 fans>   Sissy Titty and Locked Clitty     4   2025-04-08  Cum Play with me rock345 <2,585 fans>   Sissy Rian Jordan exposing myself     13   2025-04-08  Roxmysox <43 fans>   Sissy Cuckolds 38    318   2025-04-08  Feminized sissy cuckolds under the control and dominance of the women in their lives Cruel nasty Cuckoldress wives and other significant females who show utterly no mercy to the pathetic little darlings sissycarla49 <2,386 fans>   Sissy-Gay-Bi captions that made me leak today    59   2025-04-08  CockRooster <148 fans>   Sissygasm Captions 38    50   2025-04-08  Bloodrise69 <4,720 fans>   Sissygasm Captions 37    50   2025-04-08  Bloodrise69 <4,720 fans>   Sissygasm Captions 36    50   2025-04-08  Bloodrise69 <4,720 fans>   sissy time i love dressing as a sissy 2025    73   2025-04-08  my sissy cock pussy for you dookieday <1,335 fans>   Sissy captions that speak to me - 101    20   2025-04-07  Slinky_Gurl <2,791 fans>   Sissy Femboys 2    66   2025-04-07  Starcowboy <2,126 fans>   Diapers Discipline for Sissy Boys 60 (Femdom, ABDL, Punishment)    13   2025-04-07  My latest book! (amazon.com/dp/B0DH2LGZ2P) || My site (akumi-alice.com) Akumi-Alice <3,290 fans>   Sissy Public Humiliation Captions [AI, Chastity, Exposure]    9   2025-04-07  SashaSoreCapti <2,834 fans>   Sissy Drogen Bondage Fesselopfer zum dauerficken und knebeln.    309   2025-04-07  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>   ABDL Sissy Play    92   2025-04-07  Misssissyconge <782 fans>   Sissy Jaymie craves to be a Sex Slave. Kik: SissyWhiteBoy94     19   2025-04-07  Sissylover1981 <1,401 fans>   SissySlutMarty is a Size Queen     1   2025-04-07  SissySlutMarty <365 fans>   SissyAriane Collection     36   2025-04-07  Sissyariane <311 fans>   Sissy asshole    11   2025-04-07  Swiss_Sissy <387 fans>   Sissy panties    11   2025-04-07  Swiss_Sissy <387 fans>   Sissy in lingerie    19   2025-04-07  Swiss_Sissy <387 fans>   Sissy toys    17   2025-04-07  Swiss_Sissy <387 fans>   Sissy gym pant    6   2025-04-07  Swiss_Sissy <387 fans>   Sissy skirt    4   2025-04-07  Swiss_Sissy <387 fans>   Sissy ass lingerie + Chastity    16   2025-04-07  Swiss_Sissy <387 fans>   Sissy ass    4   2025-04-07  Swiss_Sissy <387 fans>   SISSY GIF'S CAPTIONS-77 - Humiliation     16   2025-04-07  kparc1212 <4,761 fans>   Sissy beta for BBC    11   2025-04-07  Bitch119 <647 fans>   Crossdressing - sissy - maid to serve    14   2025-04-07  Having some fun dressed up and playing with my dildo. Sissy crossdressing crossdresser maid outfit chastity cage dildo anal masturbation cock ass pink sextoy amateur lylyoko <171 fans>   Delicious Sissy Content 004    53   2025-04-07  Nicolekittycat <358 fans>   Sissy Sub Stute und seine Dom Daddys     19   2025-04-07  Präsentiere mich in Action , nHier nur kurze Aufzeichnungen wo ich mich in ein geilen Rollenspiel in ein Strafstellung meinen Herrn Tabulos zur Verfügung stelle im Hotelzimmer . Transe4Herren <118 fans> :: prev :: | 1 | ... | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | :: next ::