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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    femdom sissy chastity vol 149    50   2024-03-03  kmar2 <288 fans>   femdom sissy chastity vol 148    50   2024-03-03  kmar2 <288 fans>   Sissysafe/Censored-porn by melasissy    36   2024-03-02  Please dirty coments! melasissy <1,609 fans>   Sissy Thoughts     24   2024-03-02  Jarritos <10,469 fans>   It's SISSY time (2024)    12   2024-03-02  Melanie Bee <1,102 fans>   Captions: Sissy, Cuckold, Ballbusting, Domination 21    52   2024-03-02  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 <1,654 fans>   The Sissy Sluts of xxxposed.fun (Exposure Agreements)    15   2024-03-02  Sissylover1981 <1,420 fans>   Sissy's dream point of view 008    98   2024-03-02  hawk83 <3,063 fans>   Sissy Story daughters boyfriend #3    8   2024-03-02  Realmandingo94 <508 fans>   SISSY CAPTIONS 94: ASIANS IN DENIAL    11   2024-03-02  hmph!! n-not eVERy asian boi wh-who's had the misfortune o-of encountering alpha cock h-has become a shameless, willing sissy for it!! s-some asianbois have the power to resist alphas, you know!! a-and some of these very super masculine, i-independent,... FEMINYZE-CAPTI <5,071 fans>   Sissy Bitch Kendall    6   2024-03-02  Download my pics: files.fm/u/7k567kv6sj Kendall_Mckenn <1,039 fans>   My sissy confession 018    100   2024-03-02  hawk83 <3,063 fans>   fakesissy: a flower in the desert    20   2024-03-02  azu-virtualCD <84 fans>   Sissy captions about me    64   2024-03-02  natalia_marie <2,375 fans>   Deuil de Lopette 3    24   2024-03-02  deuil enterement mourning veuve widow ceremonie lopette fiotte lose gif caption french pathetic femdom humiliated sissy slave domina cuckold domina cfnm cuckold mature gifs lopette mistress fiotte slave boy gifs fiotte gif gifs crossdress06 laure... crossdress06 <3,554 fans>   Random sissy captions i created high 2    12   2024-03-02  Slutbanger00 <1,110 fans>   Edit84 - FORCED INTO SISSY RELATIONSHIP    17   2024-03-01  asjdhnasuidash <724 fans>   Edit83 - SISSY BLOWJOBS    23   2024-03-01  asjdhnasuidash <724 fans>   Yummy Bras 27    50   2024-03-01  Yummy bra images, with gentle sissy-cuck messaging. Nothing persuades a submissive guy to embrace femininity and chastity like an alpha female wearing a beautiful bra. Aikira <1,695 fans>   Most recent sissy pics    10   2024-03-01  poser1970 <332 fans>   Sissy Life - Part 3 "Dominated" - Please add your comments.    24   2024-03-01  The GF I had in my early sissy years loved seeing me fucked and loved to fuck and fist me. She could be kind or brutal I never knew which one. At the time I didn't appreciate all the wild experiences we had together but im glad we had them. Please... MeetMarilyn <3,403 fans>   Sissy whore Valery is a good meaty fuckdoll     11   2024-03-01  Bomber23 <1,416 fans>   Sissy whores are good meaty fuckdolls    29   2024-03-01  Bomber23 <1,416 fans>   Bulgarian crossdresser beauty Aleks Aleks    44   2024-03-01  bulgarian crossdresser transvestite tgirl sissy transgender shemale travesti transvestit transgenero tvsabinna <1,787 fans>   Bulgarian crossdresser beauty Beby Bali Roman    12   2024-03-01  bulgarian crossdresser transvestite tgirl sissy transgender shemale travesti transvestit transgenero tvsabinna <1,787 fans>   SISSY - GIF'S CAPTIONS - 51    16   2024-03-01  kparc1212 <4,772 fans>   Pretty Sissy Girl - 1    14   2024-03-01  Dressed like a pretty girl in 2014. SPD5708 <991 fans>   Caged sissy slut exhibition at the hotel window    9   2024-03-01  Some exhibitionism for the neighbours PhattieCakes <352 fans>   SiSSY CD SAMANTHA 26th PHOTO SET: 3-Dildo Stair Climb Workout    53   2024-03-01  Ufff...SO much stuffing of my hungry sissy fuckhole on this day! I was drenched in sweat and my boipussy was an absolute mess after this shoot. As always, please leave dirty comments and enjoy! SexySissySlutS <765 fans>   Sissy Isabel    2   2024-03-01  Mrs_Isabel <488 fans>   Rus sissy faggot 18    46   2024-03-01  Gimnast <1,545 fans>   Sissy story Daughters Boyfriend #2    2   2024-03-01  Realmandingo94 <508 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics818.1    200   2024-03-01  395royc <5,634 fans>   EMBARAZO SISSY    12   2024-03-01  ¿Eres un sissy y sueñas con quedarte embarazado? este es tu comic. davidasissy <668 fans>   Cruel Best Practices 15    26   2024-03-01  femdom, dominatrix, humiliation, slavery, beta, male sub, sissy, caged, chastity Womanservant <926 fans>   fakesissy: my friend violet and me    26   2024-03-01  azu-virtualCD <84 fans>   SANA CROSSY IN SISSY DRESS SOLO    19   2024-03-01  sana_crossy <47 fans>   SISSY SLUT IN SEXY DRESS FOR COCKS    26   2024-03-01  sana_crossy <47 fans>   Sissy captions 08    15   2024-03-01  Captions about being a complete slut and surrender to real alpha man and his juicy big cock. I'm not the autor of any of these captionsnn xxmarabuntaxx <527 fans>   Sissy Brother Sissy Son AI Captions 3    20   2024-03-01  Florazul <912 fans>   SIssy caption gifs - I am not gay am I? 3    23   2024-03-01  Slinky_Gurl <2,800 fans>   Sissy Battle #44 and #45: Claudia vs. Misha, Missy vs. Natalia    2   2024-02-29  These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   Feb Sissy GURLS Pt 4    42   2024-02-29  NaughtyNikki99 <662 fans>   Sissy Lena Lovegood is always in the mood for cock    65   2024-02-29  Lena has an own profile on imagefap too: LenaLovegood Sissylover1981 <1,420 fans>   Black Diaper and matching Bra    23   2024-02-29  Just a sissy faggot having some fun. Anyone want to spank my ass or tug on my balls while you fuck my pussy raw? Feel free to reuse, repurpose and/or repost. sparks46q <2,247 fans>   Captions sissy cuckold in french    22   2024-02-29  dasson2 <540 fans>   captions sissy cuckold with stepdaughter or niece in french    16   2024-02-29  dasson2 <540 fans>   Lana added to sissy templates    8   2024-02-29  Lananew <1,622 fans>   The Reality of being a Sissy: Clean up duties    69   2024-02-29  Theres always piss and cum to clean up, whether from a real man's cock or a real woman's pussy. You may have assholes to clean too. And of course you may be required to clean out your wife;s or mistress's pussy once she's been fucked by her... davinaglasgowt <2,353 fans>   Sissy Toy Mrs. Isabel    1   2024-02-29  Barbie's mother is a very special woman. By now, this toy has been sold more than 150000 times! KylieM <1,624 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics818    24   2024-02-29  395royc <5,634 fans>   Sissy story Daughters boyfriend #1    9   2024-02-29  Realmandingo94 <508 fans>   Sissy Madison’s Thonged Ass    18   2024-02-29  littlebitqueer <422 fans>   Sissy Auction Night    10   2024-02-29  Get your own sissy for the night! Our fucktoys will never say No! KylieM <1,624 fans>   Captions Vol 2.31 (Sissy, Cuckold, femdom, Bisexual)     16   2024-02-29  Drew73 <3,207 fans>   Slut sissy 2024-02-29    5   2024-02-29  secre123 <598 fans>   Sissy Jessiesuxxx lives up to her name (Jessie)    43   2024-02-28  Jessie is a depraved slut who knows no shame Sissylover1981 <1,420 fans>   Sissy Caged and Smooth    14   2024-02-28  Using my clitty cage, shaved myself clean and smooth and had some fun! Just wish someone was with me to play with! SissySSBBWLove <1,737 fans>   stairway spreads - showing my small sissy clit    24   2024-02-28  SissyGurlColle <1,539 fans>   Sissy Life - Part 2 "The Girlfriend" - Please add your comments.    24   2024-02-28  Welcome back ladies. Please take a moment to enjoy and comment on these captions. They are a lot of the experiences I think most of us had who shared our feminine side with a girlfriend. My old GF eventually made me do some outrageous things but the... MeetMarilyn <3,403 fans>   SISSY - GIF'S CAPTIONS - 50    2   2024-02-28  kparc1212 <4,772 fans>   Mature sissy/cd posing,    58   2024-02-28  sissygiina <151 fans>   Sissy slut exposed!    3   2024-02-28  Me just wanting to be exposed, I love the thought of my pics being uploaded all over the place. To see them and to think that they might have given just a little pleasure and caused cum to shoot really excites me, love, Lana. Lananew <1,622 fans>   faceswap- good sissy    20   2024-02-28  NuriaBunny <429 fans>   sissy slavery art 14    108   2024-02-28  submasosissy64 <1,111 fans>   Faggot Raivo Raudsepp    19   2024-02-28  Bottom slut from Estonia. Sissy fag who loves cocksucking and cum swallowing, deep assfucking and gangbangs, public sex, fucktoys and crossdressing. I like to be humiliated!!!….dressed in girly sexy things and always having something big in my... cduli <5,501 fans>   Me when Sissying, Crossdressing 03    22   2024-02-28  Photo of my real face when edited using generative AI, the face still looks original, just big tits and big breasts masniaraslann <92 fans>   Frenulum Piercing     3   2024-02-28  Got myself a frenum piercing a while ago. Was hot, but wouldn’t heal because I couldn’t keep my fingers off my cock. Got it removed again, but the story is not over… I’ll try again. Cock Schwanz Faggot Sissy Slut Cum Bottom... Frog44 <307 fans>   Sissy Gif/ Non-Gif Caps 11    31   2024-02-28  Sorry if some of the gifs look weird. I guess they uploaded oddly? Also, if it says there's only 31 images, it's wrong. The normal 40 are there. emirose2722 <907 fans>   Penis fun    20   2024-02-28  Cock Penis Schwanz Outdoor Bisexual Faggot Sissy Cuckold Slut Gay Frog44 <307 fans>   Sissy GIF Captions 3    66   2024-02-28  I_Heart_Pantie <489 fans>   Sissy Captions 13    89   2024-02-28  I_Heart_Pantie <489 fans>   DrHedon's Sissy Captions    23   2024-02-28  jadenuja <11 fans>   fakesissy    88   2024-02-28  azu-virtualCD <84 fans>   thermal bath changing area sissy in white    19   2024-02-28  nacktsklave <2,225 fans>   sissy in cruising forest    25   2024-02-28  nacktsklave <2,225 fans>   sissy in red    22   2024-02-28  nacktsklave <2,225 fans>   Crazy sissy    7   2024-02-28  Realmandingo94 <508 fans>   Candi_Kneels Original Sissy Cuckold Crossdresser Caps 22    31   2024-02-28  Candy_Kneels <929 fans>   CandyChatel01 loves sissy exposure!    15   2024-02-28  CandyChatel01 <1,144 fans>   Hannah the uk sissy 2    28   2024-02-28  sissy from uk that craves humiliations and being owned, used and abused x hannah_sissy73 <355 fans>   Captions: Sissy, Cuckold, Ballbusting, Domination 20    29   2024-02-27  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 <1,654 fans>   The Sissy Sluts of Sissy.Fun (Exposure Agreements, N. Sadistic)    94   2024-02-27  Sissylover1981 <1,420 fans>   Sissy Lingerie AI Captions 3    20   2024-02-27  Florazul <912 fans>   Sissy Focus - Naughty Puppy captions    19   2024-02-27  All pics are of the very inspiring PuppygirlX3 which I found in aliciat's galleries here on Imagefap (imagefap.com/profile/aliciat), though according to aliciat the original source was Reddit. InsertHere99 <2,474 fans>   Female politicians in charge    24   2024-02-27  Women are continuing to take over positions of power and authority. As female politicians are becoming the majority, they are taking the opportunity to institute laws and punishments against beta, sissy men. The need to relegate these weak men to a... krista024 <2,901 fans>   Sissy kik antoniego    5   2024-02-27  poids <368 fans>   Sissy friend #saving a bro    22   2024-02-27  Realmandingo94 <508 fans>   I'm a sissy slut...love make you hard    5   2024-02-27  Horny-maid <25 fans>   me the sissy    13   2024-02-27  katiefem <172 fans>   2024    223   2024-02-27  My sissy selfies for 2024 fetishforstyle <228 fans>   Sissy Asian Captions ~🎔LeanneLust🎔~ 9    9   2024-02-27  hey everyone!!!🎔 sorry for the hiatus~ had to do alot of chink holidays, and that means more money, more love and of course meeting more daddies 🎔 still on the search for a nice daddy to do the things i've been dreaming for in 2024, but... leannelustof <482 fans>   Feb Sissy Gurls PT 3    25   2024-02-27  NaughtyNikki99 <662 fans>   From SissyWorld on Telegram    12   2024-02-27  murrayjames <395 fans>   It's Just Sissy Work ---- Fake Magazine Covers 3    10   2024-02-27  SluttyZoe70 <285 fans>   Sissy caption gifs that speak to me 18    20   2024-02-27  Slinky_Gurl <2,800 fans>   CD-Sissy maids 2    100   2024-02-27  Sissy Maids, useful sometimes, used sometimes, always of service to visitors of the House tgurlbinder <1,023 fans>   Sissy Battle #42 and #43: Cindy vs. Maddy, Ileana vs. Luisa    2   2024-02-26  These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   Sissy Cocksucker Battle #3 & #4: Kaitlyn vs. Lena , Valery vs. K    2   2024-02-26  ... Valery vs. Kayla. // These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   sissy nylon tart    30   2024-02-26  emilyukcd22 <564 fans>   Sis-Life 18    64   2024-02-26  Sis-Life is no picnic. A sissy’s path contains difficulty and disgrace. But for each drop of confusion and shame, sissy will reap delicious spurts of ecstasy. Aikira <1,695 fans>   Yummy Bras 26    50   2024-02-26  Yummy bra images, with gentle sissy-cuck messaging. Nothing persuades a submissive guy to embrace femininity and chastity like an alpha female wearing a beautiful bra. Aikira <1,695 fans>   Sissy    52   2024-02-26  Checkov <22 fans>   Sissy Captions 49    16   2024-02-26  Alyssa38b <1,909 fans>   punished and humiliated sissy slaves 30    129   2024-02-26  submasosissy64 <1,111 fans>   Crossdressers in Sissy Bow Blouses 004    40   2024-02-26  Florsoie <307 fans>   Mature sissy cougar    36   2024-02-26  sissygiina <151 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics817.1    200   2024-02-26  395royc <5,634 fans>   Beta boyz, Shemale toyz BBC and Sissy caps and pics817    24   2024-02-26  395royc <5,634 fans>   Sissy Slut Sophie Softcock    9   2024-02-26  Sophie_Softcoc <5 fans>   Sissy Teen Femboy 3    62   2024-02-26  Starcowboy <2,142 fans>   Sissy Teen Femboy 2    62   2024-02-26  Starcowboy <2,142 fans>   Sissy Teen Femboy 4    48   2024-02-26  Starcowboy <2,142 fans>   Sissy Teen Femboy 1    57   2024-02-26  Starcowboy <2,142 fans>   A Grindr Encounter     19   2024-02-26  Haven't been making/posting much on here for a while now. Finally bit the bullet and sucked a real big dick and now i crave the real thing more than reading about it. Thought I'd take influence from my first few Grindr encounters and make something for... mesmomite <746 fans>   Sissy Battle #40 and #41: Carly vs. Samy, Jade vs. Veronica Vega    2   2024-02-26  These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   Pussify Your Anal Pussycunt Sissy!    39   2024-02-25  cherrylipsbaby <12,009 fans>   Pussify Your Frontcunt Sissy!    58   2024-02-25  cherrylipsbaby <12,009 fans>   Sissy Cocksucker Battle #1 & #2: Anisha vs. Dee, Ilona v. Jessie    2   2024-02-25  These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   Sissy Battle #38 and #39: Gina vs. Becca, Amber vs. Emily King    2   2024-02-25  These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   Sissy and Shemale Caps 17    23   2024-02-25  crossdressers, trans Grisgris <4,812 fans>   hot girls enjoy Sissy cam     6   2024-02-25  hot girls enjoy Sissy cam megaslutboy <104 fans>   Sissy Malila failed as a boy, but she makes a great Fucktoy     54   2024-02-25  Check out Malila´s erome gallery too. Link to it is in the comments of the first picture of this gallery. Sissylover1981 <1,420 fans>   Me when Sissying, Crossdressing 02    8   2024-02-25  I'm trying to become a hijab crossdresser. This photo is me personally, but in some parts I use AI to modify my face (with the aim of covering my identity), and just enlarge my breasts (I often fantasize like that). nnIn Indonesian culture, the type of... masniaraslann <92 fans>   Me when Sissying, Crossdressing 01    8   2024-02-25  I'm trying to become a hijab crossdresser. This photo is me personally, but in some parts I use AI to modify my face (with the aim of covering my identity), and just enlarge my breasts (I often fantasize like that) masniaraslann <92 fans>   Sissy whore Sarah     12   2024-02-25  Sissy-whore-st <2 fans>   Chantellesissy - fuck and use me hard - Thursday - Quest 29/2/24    5   2024-02-25  Who wants to tie me up, abuse me and fuck me subsissyfaggot <1,346 fans>   SISSY - GIF'S CAPTIONS - 49    16   2024-02-25  kparc1212 <4,772 fans>   Sissy slut kik xoxococo18    28   2024-02-25  poids <368 fans>   Sissy Battle #36 and #37: Anna vs. Charmaine, Bobbie vs. Monica    2   2024-02-25  These are Reposts from exposedpassion, i´m not the creator. For Deletions comment or contact me please. Sissylover1981 <1,420 fans>   Crossdressers in Sissy Clothes 009    40   2024-02-25  Florsoie <307 fans>   012 All our Fetishes Pissing    43   2024-02-25  Wir stellen in den nächsten Tagen ein paar neue Galerien hier ein um mal wieder etwas Schwung in die Sache zu bringen. Wir freuen uns auf viele geile Kommentare. Und natürlich darauf das die Bilder euch schön geil machen. Ich denke wer uns... Abenteuerland <865 fans>   Sissy Faye Toy    7   2024-02-25  manu_1970 <579 fans>   What sissymaster2022 likes mega gallery     400   2024-02-25  sissymaster202 <815 fans>   Diana tiny sissy clit    42   2024-02-25  SissyDiana65 <498 fans>   Mistress Sissy Caption 7    40   2024-02-24  Mistress Sissy Captions Sissy_Scarlett <1,430 fans>   LaceyLovesCD I feel more SISSY    144   2024-02-24  I love wearing sexy lingerie.I feel more sissy when I do. LaceylovesCD <4,030 fans>   Sissy Gurls in Red    14   2024-02-24  cherrylipsbaby <12,009 fans>   Sissy pussy for fucking    23   2024-02-24  claireglades <180 fans>   Sissy caption gifs that speak to me 17    20   2024-02-24  Slinky_Gurl <2,800 fans>   Wish i was the gurl sissy bully caption gifs 2    20   2024-02-24  Slinky_Gurl <2,800 fans>   Sissy Captions 20    50   2024-02-24  Sissy Captions Sissy_Scarlett <1,430 fans>   Sissies Together/Sissy Lesbians 5    991   2024-02-24  ClosetGurlyBoy <2,019 fans>   Cd Sissy cock suckers    18   2024-02-24  GirlyJamie <1,079 fans>   Horny sissy faggots craving exposure     6   2024-02-24  These sissies need your help. Please download and repost the pictures. KylieM <1,624 fans>   The Sissy Catalog 14    21   2024-02-24  aliciat <10,346 fans>   My sissygasm Vol. 1    2   2024-02-24  Amarahot <85 fans>   sissyslave    15   2024-02-24  nacktsklave <2,225 fans>   Sissy snow white     97   2024-02-24  Luvtwocum1 <1,500 fans>   Sissy Lydia Gomez has a face to cum on - kik: lydia_gomez1092 -    9   2024-02-24  Sissylover1981 <1,420 fans> :: prev :: | 1 | ... | 69 | 70 | 71 | 72 | 73 | 74 | 75 | 76 | 77 | 78 | :: next ::