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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 Maid Karina is ready to please even the dirtiest needs     21   2024-10-19  More of Karina on her imagefap profile: kahrinah Sissylover1981 <1,416 fans>   A glimpse of stocking    54   2024-10-19  SissnSissynStockingsnChastitynCross dressn Mistressandsis <1,388 fans>   German sissy slave looking for Owner    8   2024-10-19  27 years old sissy slave from Germany is currently unowned but craves to serve a strict and serious Master longterm.nI need a mean Master who likes to have complete control over his slaves. Very interested in CNC, blackmail and forced feminization so... SissyChrissyNB <153 fans>   sissy in public toiet    6   2024-10-19  nacktsklave <2,225 fans>   Sissy Cumslut Captions 16    50   2024-10-19  Bloodrise69 <4,738 fans>   Sissy Cumslut Captions 15    50   2024-10-19  Bloodrise69 <4,738 fans>   Sissy Cumslut Captions 14    50   2024-10-19  Bloodrise69 <4,738 fans>   Sissy Captions My Pics    29   2024-10-19  sissycaptions nshemalentsncrossdressing Bifems <924 fans>   sissy Gigi posing sexy    20   2024-10-19  sissygigiolidi <182 fans>   My Sissy Captions 17 (Halloween)    15   2024-10-19  cdnicole <1,530 fans>   Sissy Bitch posing 2    15   2024-10-18  sandracduk <683 fans>   Dirty Old Perverts Humiliate and Wreck beta sissy bois 13    24   2024-10-18  How had you let yourself fall into the evil clutches of old Uncle Pervy?! Somehow, he’d “persuaded” you to dress up in his wife’s old clothes, then suck his smelly old cock, but now… Now he’s preparing to make me... Candy_Runt <4,599 fans>   Forcibly Feminized and Fucked - Sissy Humiliation Captions 116    24   2024-10-18  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 are available, exclusively, from the Lulu.com online... Candy_Runt <4,599 fans>   Good sissy&rsquo;s do as they are told    26   2024-10-18  Missbianca <176 fans>   The Sissy Catalog 17    21   2024-10-18  aliciat <10,343 fans>   Sissy captions gifs that speak to me 68 - more pink pills    20   2024-10-18  Slinky_Gurl <2,797 fans>   ABDL SISSY FAGGOT BABYGIRL NURSERY    12   2024-10-18  ABDLSISSYBABYG <74 fans>   Cuck Captions 294    50   2024-10-18  It's very difficult trying to pretend to your other half that you're satisfied with your sex life, when really you want to be a dirty slut and fuck any guy you can get your hands on! I know he knows this deep down, but for his own pride he tells... Exquisitepassi <1,385 fans>   Sissy Sasha - Pantyhose    2   2024-10-18  Sasha from Uk. 22y. My size clitty: hard is 5 inch, soft 3 inch 111a111c <41 fans>   Sissy Test    19   2024-10-18  jeansissy <38 fans>   Fatty in pantyhose     3   2024-10-18  I'm a fat pantyhose wearing sissy who deserves to be humiliated and exposed. Fatsissy36 <3 fans>   Sissy me     11   2024-10-18  Jennifersissy1 <23 fans>   Sissy Cumslut Captions 13    50   2024-10-17  Bloodrise69 <4,738 fans>   dildos,plugs, and sissy outfits    35   2024-10-17  katieabsissy <193 fans>   Pretty celebrities humiliate me for being a virgin sick loser    5   2024-10-17  pathetic, a loser, desperate, sick, perverted, a sissy , a faggot, a high heel licking toilet boy, a dress and skirt wearing faggot...everything i am emmawatsonssla <2,360 fans>   Mistress Sissy Caption 18    45   2024-10-17  Mistress Sissy Caption Sissy_Scarlett <1,428 fans>   ABDL SISSY FAGGOT BABYGIRL    10   2024-10-17  ABDLSISSYBABYG <74 fans>   Big Assed Sissy Claudia Blonde can not stay away from Exposure    11   2024-10-17  Sissylover1981 <1,416 fans>   BBC SISSYGASM    1   2024-10-17  Girlyliza <220 fans>   Sissy Cumslut Captions 12    50   2024-10-17  Bloodrise69 <4,738 fans>   Sissy Nikki Pinky 013    10   2024-10-17  SissyNikkiPink <135 fans>   Sissy Cumslut Captions 11    50   2024-10-17  Bloodrise69 <4,738 fans>   100% MtF Post-Op Transwoman - Emma    44   2024-10-17  Gallery of Emma, a post-op male-to-female (mtf) transwoman. Has had SRS (vaginoplasty). Tranny, Trannies, Shemale, Sex Change, Sissy, Transgender, Transsexual rickbennett <1,948 fans>   Sissy Pantyhose Caption 9    45   2024-10-17  Sissy Pantyhose Caption Sissy_Scarlett <1,428 fans>   100% MtF Post-Op Transwoman - Lilly    39   2024-10-17  Gallery of Lilly, a post-op male-to-female (mtf) transwoman. Has had SRS (vaginoplasty). Tranny, Trannies, Shemale, Sex Change, Sissy, Transgender, Transsexual rickbennett <1,948 fans>   Sissy slut locked up with panties     14   2024-10-17  Missbianca <176 fans>   Best of Sissy Feminization Captions 61-70    50   2024-10-17  Bloodrise69 <4,738 fans>   Sissy candyfloss    8   2024-10-17  Daddyddk <1 fans>   ABDL SISSY FAGGOT BABYGIRL NURSERY    9   2024-10-16  ABDLSISSYBABYG <74 fans>   ABDL SISSY FAGGOT BABYGIRL    5   2024-10-16  ABDLSISSYBABYG <74 fans>   Toons (Sissy Suburbia)    11   2024-10-16  CDCuck <1,803 fans>   Pink Sissy Cum Slut    32   2024-10-16  SissyDee65 <622 fans>   Gilfys Muschi    2   2024-10-16  Ich darf bekannt machen: das ist GILFYs-Muschi. Fleischig, haarig, von ihrem Sissy-Wallach zu Hause sträflich vernachlässigt. Und hungrig, sehr sogar! Scheint immer mehr Gefallen an der härteren Gangart zu finden. Bootssteg <225 fans>   french sissy slut @Chloe_the_whore    10   2024-10-16  Gooner44french <37 fans>   Sissy Dreams and Fantasies 21    47   2024-10-16  Picture collection of visual representations of my sissy dreams and fantasies. Some sissy captions. sissy_ashleigh <278 fans>   Sissy Dreams and Fantasies 20    50   2024-10-16  Picture collection of visual representations of my sissy dreams and fantasies. Some sissy captions. sissy_ashleigh <278 fans>   DEI ACADEMY PT 2    30   2024-10-16  DIVERSITY-Focus On ALL Those Better Than Yourself In Your Very Purpose Of Being.EQUALITY - Superiors Deserve Your Devotion, Service and Appreciation Equally INCLUSION - You're A Sissy A CUM Slut, As Such It Is Your DUTY To Provide Relief Of Sexual... NaughtyNikki99 <662 fans>   Oct Sissy GURLS PT 3    70   2024-10-16  NaughtyNikki99 <662 fans>   My sissy pics    13   2024-10-16  Lulitacross <441 fans>   Sissy Andrew Brown in Blue Bodysuit and Heels    28   2024-10-16  I'm not sure yet if I'm in love with square toe heels, but hey, any heels are better than no heels. And I do love the body suit. Hope you enjoy an.d feel free to share/repost txpeter422 <617 fans>   Sissy captions gifs that speak to me 67    20   2024-10-15  Slinky_Gurl <2,797 fans>   hanna uk sissy captions     12   2024-10-15  sissy from uk for humiliation hannah_sissy73 <354 fans>   Deutsche Captions von wertlose Sissy Hure / German Captions 3    23   2024-10-15  maryneuman <910 fans>   Sissy Baby Gurl Oct 24    30   2024-10-15  SissyDee65 <622 fans>   Cuckold Sissy Captions 7    42   2024-10-15  Cuckold Sissy Captions Sissy_Scarlett <1,428 fans>   Candi_Kneels Original Sissy Cuckold Crossdresser Caps 31    33   2024-10-15  Candy_Kneels <928 fans>   Feminization of me    57   2024-10-15  Feminization,fag,Faggot,piercing,chastity,hypno,hypnotube,trav,sissy,sissy faggot lecheur53 <395 fans>   Sissy Feminization Captions 70    50   2024-10-15  Bloodrise69 <4,738 fans>   Sissy Captions 64    16   2024-10-15  Alyssa38b <1,909 fans>   Black Cocks Creating White Sissy Bitches    8   2024-10-15  Not my regular style but I felt like a change. Feel free to rate the pictures and add comments jonblacker <5,961 fans>   Sissy Sub Cait-Marie 1 (Tgirl/CD)    159   2024-10-15  aliciat <10,343 fans>   Sissy talkies    387   2024-10-15  / sissy captions SissyKat <40 fans>   Sissy Feminization Captions 69    50   2024-10-15  Bloodrise69 <4,738 fans>   Sissy Woods     30   2024-10-15  Cum play with me rock345 <2,586 fans>   Sissy Bitch    5   2024-10-15  Sissyprick85 <153 fans>   GILFy    11   2024-10-14  GILFy lady. She is, believe it or not 64yo. Sie wurde mir von ihrem Sissy-Ehemann, der nicht mehr ficken mag/kann über eine Online-Plattform angetragen. Die Fotos entstanden an unserem Kennenlernabend nach einem wunderbaren Abendessen. Ich habe sie... Bootssteg <225 fans>   Exposed n.336 Sissy Linda TeaSe    42   2024-10-14  ExposingAcadem <1,169 fans>   Sissy Humiliated - A Story with Pictures    29   2024-10-14  NOTE: There are three panels that I did not publish with this post (later part of story) as it could be offensive to some (mild scat). If you would like to see the missing pics, write to me at beenwantingtwo@gmail.com beenwantingtwo <288 fans>   New Sissy Maid Outfit    8   2024-10-14  missjaime <1,279 fans>   Sissy Short Series 061    16   2024-10-14  InsertHere99 <2,472 fans>   Pantyhose SIssy Bottom - sorrycantdothat on X    966   2024-10-14  seamlesshosebo <49 fans>   Sissy Feminization Captions 68    50   2024-10-14  Bloodrise69 <4,738 fans>   Sissy Slut Izzy - posing for BBC     19   2024-10-14  Isabelle_Dix <873 fans>   Captions tiny sph sissy 8    48   2024-10-14  I love showing my tiny clitty, exposing other little worms and making collages and captions. You can use my pictures of my useless tiny for your future files. Your comments are always welcome stantonz <4,955 fans>   Sissy Izzy - tiny dicklette in red    23   2024-10-14  Isabelle_Dix <873 fans>   Sissy Slut For Black BBC Daddies    4   2024-10-14  Kimnylons <1,114 fans>   34 Sissy    95   2024-10-14  Opentabooguy2 <1,156 fans>   Lily Collins sissy captions    12   2024-10-14  pp983 <1,191 fans>   Pantyhose Women with Jobs dealing with a sissy    24   2024-10-13  Women wearing pantyhose dealing with a sissy or sissies at work or after work. SissyPHTights <672 fans>   Pantyhose and Sissy Things Random Captions    24   2024-10-13  Not all of these are 100 percent original as a few of them were captions that I saw and felt the need to add something too. Special thanks to the original caption creators and of course the artists who created the artwork I captioned or added to. SissyPHTights <672 fans>   J.Ward, married sissy exposed    12   2024-10-13  xeu2024 <98 fans>   Pantyhose Asylum 5 Resthaven 2 Now Open    24   2024-10-13  The promised addition to the pantyhose asylum series. Resthaven 2 the pantyhose and straitjacket asylum for women, girls, and sissy gurls. SissyPHTights <672 fans>   Pantyhose Sissy Captions featuring me    12   2024-10-13  Some pantyhose sissy captions about me using pics of me. Not a full album by my usual standards. Guess I need to take more pictures of myself. Please comment if you see something you really like! SissyPHTights <672 fans>   Blanket Loving Sissy Gurl    5   2024-10-13  I hope you enjoy my silly, pervy pics. Feel free to make ANY kind of comments you want on my pics, complimentary or outright insulting! NICE or FILTHY comments are always welCUM. Degrade and/or humiliate me in ANY way you want. I'm nothing but a... Barbara_Blanke <3 fans>   Sissy Dannii knee high socks Oct 24    14   2024-10-13  OrLLin89 <635 fans>   Betasafe Censored Pornstars 5    100   2024-10-13  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 <777 fans>   Sissy Gurls -Exposed Edition- (Fake Magazine Covers, Captions)    44   2024-10-13  Sissylover1981 <1,416 fans>   sissy in adult cinema    28   2024-10-13  nacktsklave <2,225 fans>   Sissy AI heaven    200   2024-10-13  Misssissyconge <790 fans>   More Sissy Maids    20   2024-10-13  Slinky_Gurl <2,797 fans>   Sissy captions that speak to me 69 - comic 2    20   2024-10-13  Slinky_Gurl <2,797 fans>   Sissy Gay Ass    32   2024-10-13  Fuck my Pussy Deep rock345 <2,586 fans>   Does my sissy ass look cute in green?    6   2024-10-13  RosieTay <99 fans>   Sissy Feet and Pretty Toes 37    913   2024-10-13  ClosetGurlyBoy <2,016 fans>   Posing in Panties Sissy Trap CD/TV 1    10   2024-10-13  Pval23 <343 fans>   Pink Dress Sissy    4   2024-10-13  RosieTay <99 fans>   Oh Tu Regardes ma culotte petit pervers    14   2024-10-13  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 <3,548 fans>   vidcapts of My Sissy bruised cunt needs some vitamins part2    21   2024-10-13  Juste some screen captures of my 2 vids -My Sissy bruised cunt needs some vitamins part1 and part2- for tease swollen_man_cu <516 fans>   Sissy in panties    5   2024-10-12  ninacrossdress <891 fans>   sissy slut    3   2024-10-12  fetishcdsut <170 fans>   Crossdresser and Sissy Pegging GIFs    15   2024-10-12  KarinaClarkeTV <821 fans>   Sissy Captions 32    44   2024-10-12  Sissy Captions Sissy_Scarlett <1,428 fans>   Mistress Sissy Caption 17    44   2024-10-12  Mistress Sissy Caption Sissy_Scarlett <1,428 fans>   Sissy Triggers - Pink Pink Pink Pink    22   2024-10-12  twosissiesinwo <339 fans>   Mature sissy tease    21   2024-10-12  katorio0417 <839 fans>   TG/Sissy Captions #4    6   2024-10-12  Check out more on my profile :) Lexi221 <145 fans>   Sissy captions gifs that speak to me 66    20   2024-10-12  Slinky_Gurl <2,797 fans>   Captions Sissy, Cuckold, Ballbusting, Domination 48    23   2024-10-12  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 <1,653 fans>   Oct Sissy GURLS Pt 2    50   2024-10-12  NaughtyNikki99 <662 fans>   SISSY CAPTIONS 111: THE EXCHANGE PROGRAM    10   2024-10-12  this week's set is one i've been cooking up for a loooooong time, so i'm super excited to share it with you all~!! i-it's something of a sordid mashup of allll my fave kinks... packaged into a sexy lil narrative about two senior students on a high... FEMINYZE-CAPTI <5,070 fans>   Sissy Julie Allison Costume: Cheerleader 2    37   2024-10-12  Sissy Julie Allison Costume: Cheerleader JulieAllison <605 fans>   Crossdresser Captions Thirty Two    40   2024-10-12  Tell me how you'd use my soft little sissy body. ;) filthyp <926 fans>   fake sissy d    119   2024-10-12  ikubatt <782 fans>   Sissy ass in pink thong bikini    6   2024-10-12  male4footjob <37 fans>   Sissy Feminization Captions 67    50   2024-10-12  Bloodrise69 <4,738 fans>   Pink Sissy    17   2024-10-12  GirlyGirlAmi <512 fans>   Lovely Sissy Cleo    121   2024-10-12  rubberboy-nl <1,470 fans>   Sara Dream Sissy 3    12   2024-10-12  SaraDream <238 fans>   Sissy, Cockold Captions and stuff    50   2024-10-11  maxfellas <476 fans>   CD/TV Sissy Trap Amateur     35   2024-10-11  Pval23 <343 fans>   Sissy GIF Captions    23   2024-10-11  First time creating captions and GIFs, so a lot of room for improvement, but here they are! Let me know if you like them ;) sirky <3,350 fans>   my favorite sissy toon pics    44   2024-10-11  katieabsissy <193 fans>   A Pervert Out and About    30   2024-10-11  I was extremely horny, so I took my sissy show on the road. I started at Kohls, who unknowingly let me expose myself in my onesie and diaper. From there, it was the park, which I had all to myself, and took in the fresh air on my naked lewd body.... beenwantingtwo <288 fans>   Lingerie sissy     44   2024-10-11  jasmyna <424 fans>   She Made Her Boyfriend her beta Bitch - FemDom Captions 8    24   2024-10-11  Forced feminization captions reflecting my love of sissy humiliation at the hands of powerful and dominant women, themes that are given center stage in my SEVEN beta bitch domination e-books, available exclusively from the online publisher... Candy_Runt <4,599 fans>   Sissy Fashion    50   2024-10-11  Futa-pervo <709 fans>   Smelly Old Men Wreck beta Bois - Old Pervert Captions 7    25   2024-10-11  Grandpappy promised he wouldn’t tell anyone about how he made me dress up like a little girl and suck his… For more perverted fun like this check out my sissy humiliation e-books at www.lulu.com/spotlight/candy_runt Candy_Runt <4,599 fans>   Sissy/ Cd Features    27   2024-10-11  Girlyliza <220 fans>   Sissy_Feminisation    7   2024-10-11  justchastitybl <47 fans>   Sissy Feminization Captions 66    50   2024-10-11  Bloodrise69 <4,738 fans>   Sissy Sasha - Stripes    4   2024-10-11  Sasha from Uk. 22y. My size clitty: hard is 5 inch, soft 3 inch 111a111c <41 fans>   Captions Vol 2.40 (Sissy, Cuckold, femdom, Bisexual)     16   2024-10-11  Drew73 <3,206 fans>   Edmonton sissy cum slut     8   2024-10-11  Edmonsub <69 fans>   Why this sissy worships Shemales #3    73   2024-10-10  c3poslave <1,024 fans>   Sissy Nikki Pinky 012    13   2024-10-10  SissyNikkiPink <135 fans>   Sissy Captions 31    43   2024-10-10  Sissy Captions Sissy_Scarlett <1,428 fans>   Sissy Babecock Captions 2    5   2024-10-10  Socalsissyboi <281 fans>   Sissy Feminization Captions 65    50   2024-10-10  Bloodrise69 <4,738 fans>   Beta Bitches Buggered by Black Alphas - Interracial Captions 25    24   2024-10-10  Forced feminization captions reflecting my love of sissy humiliation at the hands of powerful black men, dominant women or creepy old perverts. All of which are given center stage in my SEVEN beta bitch domination e-books, available exclusively from... Candy_Runt <4,599 fans>   Forcibly Feminized Sissy Humiliation Captions 115    24   2024-10-10  Three new stories involving a submissive, though straight, white guy who lets others bully or blackmail him onto serving as their sissy sex slave, leading to all manner of deeply depraved and humiliating escapades! You can find them, alongside my other... Candy_Runt <4,599 fans>   Sissy Feminization Captions 64    50   2024-10-10  Bloodrise69 <4,738 fans>   UK sissy Arrabella    6   2024-10-10  Peter Jones from Chorley Lanashire BadLex55 <452 fans>   small cock sissy showing off in animal print    36   2024-10-10  Download, save and repost to further this sissy's exposure! SissyGurlColle <1,537 fans>   Sissy Feminization Captions 63    50   2024-10-10  Bloodrise69 <4,738 fans>   Sissy 27    17   2024-10-10  Poor boys caged, bound, feminized, deflowered viktrig <469 fans>   Sissy Captions #2 - Stay Limp For Pussy     22   2024-10-10  cultofnicole <58 fans>   my true sissy nature #2    139   2024-10-10  c3poslave <1,024 fans>   Why this sissy worships Shemales #2    90   2024-10-10  c3poslave <1,024 fans> :: prev :: | 1 | ... | 41 | 42 | 43 | 44 | 45 | 46 | 47 | 48 | 49 | 50 | :: next ::