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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    Traps, Sissies, Femboys, and Crossdressers 2    122   2023-08-26  ubernothingnes <297 fans>   Sissy 4    109   2023-08-26  masniaraslann <92 fans>   Growing cock in tiny green panties    5   2023-08-25  Showing my growing cock until full erection in a tiny pair of panties jozz_34 <448 fans>   Camila    257   2023-08-24  ubernothingnes <297 fans>   TRAP 10    5   2023-08-24  SWEETWIFEDOM <1,126 fans>   Tears of the Dick (Japanese)    15   2023-08-24  sissyhoon <2,280 fans>   Traps, Sissies, Femboys, and Crossdressers 1    83   2023-08-24  ubernothingnes <297 fans>   School started naughty Teacher     18   2023-08-23  Whore teachers first day at school some of the naughty boys will need extra credit after school PrissyGurl24 <867 fans>   String Show    17   2023-08-23  I love the feeling (and the look) of having a tampon in my ass, under my panties.nThere's something about it that makes me feel extra girly........ Never_Guess <142 fans>   sissycuckold 17    314   2023-08-22  The twisted life the feminized sissy cuckold leads under the heel of women! sissycarla49 <2,391 fans>   Shemale Monica M - some other mixed ones    14   2023-08-22  Monica M <699 fans>   SiSSY CD SAMANTHA 18th PHOTO SET: Caged Butt-Slut with Big Tits    44   2023-08-20  Bimbo titty upgrade! Caged and waiting for Daddy's big cock. SexySissySlutS <1,728 fans>   New pink skirt    8   2023-08-20  New Pink Skirt going to go trolling for tuckers along the highway PrissyGurl24 <867 fans>   Me in panties     54   2023-08-19  NBpantylover <112 fans>   Wigless Transvestite/Sissy Nick Carter to Expose    38   2023-08-19  A selection of photographs of me exposed without my wig. Download, save, expose me. I love to get dirty emails: nick_carter@mail.com tvinheaven <1,990 fans>   Mature Cds 10    25   2023-08-19  More gurly gurls showing their female side demonsaab <681 fans>   Mature Cds 9    25   2023-08-19  More gurly gurls showing their female side demonsaab <681 fans>   Playing in black     7   2023-08-18  Playing in black pvc Serendipityxx <1,312 fans>   Camera Fun 14    30   2023-08-17  Hi all. I hope you are still there after some summer rest. I present a new album that I hope will give you some kind of pleasure, and maybe some fine stroking sessions... JanH <1,052 fans>   sissy lingerie    32   2023-08-16  Sissy lingerie I want to wear - what would you do to me if I dressed like this? keifd <620 fans>   Link 1(Trap)    59   2023-08-16  coran25 <2,359 fans>   Faggot Roberta giving blowjob     1   2023-08-15  sissy_roberta <98 fans>   Dressing outdoors #1    19   2023-08-15  Dressing outdoors in public alas. I’ve waited a long time to find me a spot and get all girly. Hope you like this hike. Charmstheshell <252 fans>   Sissy Asian Captions ~🎔LeanneLust🎔~ 5    10   2023-08-15  spread the word girlies ;) doesn't matter whether you are taken or single, all asians have holes and they need to be filled by BIG WHITE COCK leannelustof <484 fans>   naughty bridesmaids    27   2023-08-11  keifd <620 fans>   Sissy Gif/ Non-Gif Caps 7    40   2023-08-11  emirose2722 <915 fans>   More Meat than You can Handle 001    181   2023-08-11  vinny1984 <110 fans>   Gladiator shoes    21   2023-08-10  daniellecz <2,022 fans>   Trying GF' black dress with heels    11   2023-08-10  So my gf decided to leave some clothes and i just tried this dress and it really did fit so sexy omg! It worked so well with my black wedge sandals i decided to take some photos, put some gender AI (just to not use lace and makeup) and share with u, as... winiwin <10 fans>   Feminine inspiration 38     144   2023-08-10  Lingerie nPanties nCrossdressing nFeminization n Serendipityxx <1,312 fans>   Sissy Dresses    8   2023-08-09  keifd <620 fans>   sissy panties    12   2023-08-09  keifd <620 fans>   Suson Fetish 22    235   2023-08-08  suson sissy nappy diaper abdl fetish pee plastic plasticpanty panty submissive ageplay regression pvc leather latex rubber piss adultbaby ab smooth slippery satin maid sissysuson <272 fans>   Christina Naye's Black Sexy Underwear    36   2023-08-06  This is my photoshoot #40. I'm both the model and photographer. Please feel free to comment, that makes me really excited. ChristinaNaye <863 fans>   The French Maid 81    14   2023-08-06  Posing in my yellow Satin Sissy Maid Dress trimmed in white lace and a matching satin apron trimmed in silver worn with a 100 ys of all white lycra and shimmering organza petticoat, matching hand-made leather Collar and Cuffs Set and white lace... Maid_Teri <702 fans>   Sissy    8   2023-08-04  SissyFagMirko <14 fans>   Me, slut sissy for exposure 2    5   2023-08-04  ManonSissy <240 fans>   Me Cindy Cross crossdressing working as a hotel maid    1   2023-08-04  Me Cindy Cross crossdressing working a hotel maid cindy_cross39 <1,669 fans>   Gurls Girls Gurls     111   2023-08-04  Serendipityxx <1,312 fans>   Klara    9   2023-08-02  blackromel80 <1,593 fans>   @Danielatravhot    6   2023-08-02  blackromel80 <1,593 fans>   Groom & Groom [crossdressing, gay, partly censored]    23   2023-08-02  qnd84 <1,882 fans>   Mature Cds 12    32   2023-08-01  Another collection of some of my favourite gurls demonsaab <681 fans>   Mature Cds 11    32   2023-08-01  Another collection of some of my favourite gurls demonsaab <681 fans>   Real Messages I've Gotten As a Hot Sissy On Grindr and Online#    16   2023-07-31  I collected some of the hottest messages I've received on Grindr and other places online. I hope you like them and get inspired to hop on and find a man that will do these things to you :). All of these messages are 100% real. Part 4 coming soon? ZL822 <681 fans>   SISSY CAPTIONS 79: MISCELLANEOUS HENTAI    16   2023-07-29  a-are you getting bred by your nasty bullies?? feminized and pimped out by horrible gangsters?? dressed up cutely and made to act like an idol for a whole soulless, sissy-exploiting corporation?? i-it's a terrible world out there for a poor, innocent,... FEMINYZE-CAPTI <5,096 fans>   Impromptu dress up     18   2023-07-28  Serendipityxx <1,312 fans>   Me in various underwear - kinkiest set, hardest cock    14   2023-07-28  Exposing myself in various types of underwear jozz_34 <448 fans>   Sissy slut tight ass jeans(please comment)    77   2023-07-28  Tight jeans ass toplover918 <20 fans>   Feminine inspiration 36    75   2023-07-27  A fine selection of beautiful ladies in lingerie who wouldn’t want be them love them and wear their beautiful clothes Serendipityxx <1,312 fans>   Sissy Asian Captions ~🎔LeanneLust🎔~ 4    9   2023-07-26  Its been a busy time for me, but i can never forget my roots. hope you guys like a mix of my old and new captions leannelustof <484 fans>   Trying my new heels :)    17   2023-07-22  bronto34us <705 fans>   More of Susan_cd2000 looking for comments.    3   2023-07-22  Susan_cd2000 want to see if men use her for their enjoyment. Leave comments about this sissy she wants to hear what you think. daddydave1 <1,468 fans>   Sissy Suburbia 19 bonus outfits    8   2023-07-21  New sissy art made by me. Evthorn. Please comment if you like the images. It's nice to get support ;) Thanks to everyone for the comments so far evthorn <603 fans>   Sissy Suburbia 18    4   2023-07-20  New sissy art made by me. Evthorn. Please comment if you like the images. It's nice to get support ;) Thanks to everyone for the comments so far evthorn <603 fans>   College Sissy 2    10   2023-07-19  Animated GIFs of Former Jocks, Studs and Pussy chasers turned into sissy cock craving whores. - fag, fags, gay, gays, Twink, twinks, faggot, faggots, sissy, sissys, sissies, girlie, girlie, boi, girly, boi, girly, boy, queer, queers, Shemale, Shemales,... AdamTX86 <2,303 fans>   Daughters & Mothers In Control 31    24   2023-07-18  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 <2,917 fans>   dressed to drill pt.: 7 time to drill!    100   2023-07-18  i guess it's about time to cut the chase and shove some cock or dildo into some allocated hole and drill until at least one person has an orgasm. detailed view is highly recommended because each pic is individually commented. Nylondoner <1,664 fans>   Wife's Black Lacey Tube Top Can Be Used Other Ways    12   2023-07-18  Wife's Lace Tube Top GGC123 <1,416 fans>   My Black Panties and Wife's Black Lace Cami    10   2023-07-18  In My wife's camisole and my Black Panties GGC123 <1,416 fans>   susan_cd2000captioned She needs a good fucking.    3   2023-07-17  susan_cd2000 always showing off her sissy ass and needs to be fucked. daddydave1 <1,468 fans>   CD vintage photoshoot    7   2023-07-17  Burlesque-style hotel photoshoot with a present for the photographer lottiefirth <304 fans>   SISSY CAPTIONS 78: ASIAN INDULGENCE    10   2023-07-15  s-some asian sissies are very very bad at hiding their "secret" d-desire for alpha cock... th-they might play it bratty, o-or reluctant, or just give up on hiding it entirely a-and practically beg you for your enormous superior cock... u-umm... wh-what... FEMINYZE-CAPTI <5,096 fans>   Permanent Rubber Doll    117   2023-07-15  os1408 <473 fans>   Hot Feminine Goals     41   2023-07-14  Serendipityxx <1,312 fans>   The story of my punishments    2   2023-07-14  Gallery contain pics of my punishments for failed tasks Dru93 <359 fans>   New Pvc waist trainer     8   2023-07-14  Serendipityxx <1,312 fans>   Early Sissy Me    14   2023-07-14  My first go at dressing like a sissy. Hadn’t considered my clitty and body needed a good shaving yet! Still finding more old pics to post up, so let me know if you would like to see more! SissySSBBWLove <1,751 fans>   Lost and found cotton thong    40   2023-07-14  I found this thick cotton thong in a supermarket carpark. There was a little leakage while I was having fun wearing it ;) Semimental_75 <1,494 fans>   Sissy Asian Captions ~🎔LeanneLust🎔~ 3    10   2023-07-12  Found some of my old captions, really glad to be able to share them again. Sissify all asians leannelustof <484 fans>   Suson Fetish 21    240   2023-07-11  suson sissy nappy diaper abdl fetish pee plastic plasticpanty panty submissive ageplay regression pvc leather latex rubber piss adultbaby ab smooth slippery satin maid sissysuson <272 fans>   Go get pinked out     38   2023-07-11  Because we all could use more pink lingerie and cute outfits..go pink today Serendipityxx <1,312 fans>   more of my ass    21   2023-07-11  colinori <110 fans>   Girly and sissy stuff I like    970   2023-07-11  SubNPassive1 <760 fans>   Time for a haircut    26   2023-07-10  Getting a bit fuzzy down there so time for a trim ;) Semimental_75 <1,494 fans>   Daddy, can you kiss me?    6   2023-07-08  Sayo0707 <83 fans>   Sexy Styles    13   2023-07-08  Several femboy pictures doing sexy things showing off my cute cock and squishy belly. chanhaven56 <67 fans>   Lingerie Poses    7   2023-07-08  Posing in lingerie. chanhaven56 <67 fans>   Wearing New Cute Panties    16   2023-07-08  Making Poses while wearing cute panties and a bra to cover my cute boy nipples. chanhaven56 <67 fans>   After party of sissy in chastity (sub517)    47   2023-07-07  Dru93 <359 fans>   Sissified     216   2023-07-07  some images of men being seduced into femininity - most frequently by women Grisgris <4,836 fans>   Hot captions and hot femmes     66   2023-07-07  Serendipityxx <1,312 fans>   The French Maid 80    30   2023-07-03  Posing in my B31 Satin Sissy Maid Dress which is adorned with Taffeta and trimmed in silver with a matching satin apron. Purchased form BBT Sissy Closet Maid_Teri <702 fans>   My first randomly SOUNDING feeling.    19   2023-07-03  While practicing with a transurethral catheter, I noticed that it made me fucking horny. I was very surprised, but I love that sounding feeling. CagedForFun <791 fans>   I wish I was her and this could happen to me 3    982   2023-07-03  SubNPassive1 <760 fans>   Happy Coerced Day    35   2023-07-02  Welcome to Coerced Day, where sissies experience their first taste of feminization, femdom, crossdressing, pegging and submission from their kinky mistress! purekinkiness <662 fans>   Sissy wearing tiny cage and pink high heels    14   2023-07-02  Sissy wearing a tiny chastity cage and pink high heels CagedForFun <791 fans>   Sissy wearing pink lingerie and very tiny chastity cage    13   2023-07-01  CagedForFun <791 fans>   (#3) gay/sissy mind-control captions    4   2023-07-01  I do not own any of the images. I do not condone violence, acts depicted are purely fantasy Amogus <122 fans>   FEMDOM CAPTIONS 15: ASIAN HUMILIATION    11   2023-07-01  despite what many o-of my other caption sets might have you thinking, n-not all asian girls are exclusively obsessed with superior bwc and bbc!! s-some are super dedicated to humiliating, emasculating, a-and feminizing their big-clitted sissy... FEMINYZE-CAPTI <5,096 fans>   Pink Organza Sissy Maid Dress    21   2023-06-30  Posing in G2409 Baby pink organza Sissy Dress/Adultbabydress with dainty Rose wrist cuffs and matching locking ankel cuffs, a matching pink organza petticoat, matching satin ruffle panties, pink Secrets in Lace 15 denier nylon European Heel Full... Maid_Teri <702 fans>   me 2    16   2023-06-30  sissysophiex <120 fans>   I wish I was her and this could happen to me 2    987   2023-06-30  SubNPassive1 <760 fans>   Sissy/trans Cosplay Captions #1    16   2023-06-30  Cosplay captions for sissies and trans! It's so fun and liberating using cosplay as one of the first sissy/trans outlets, isn't it?nPlease leave me some yummy comments to let me know if I should make a part 2~ Elliie <780 fans>   Sissy Captions Collection 7    20   2023-06-29  thisshouldnote <523 fans>   Sissy me with some reblogs     6   2023-06-28  first time showing my awful face lol NWSissy <189 fans>   Clothes I'd like to wear and girls I'd like to look like 18    48   2023-06-28  When I first started making galleries I never thought I would find so many clothes I'd like to wear, yet here it is gallery 18. This is a view of the type of clothes that I'd love to try on and wear. My tastes change from time to time, and this is... krista024 <2,917 fans>   Pathetic Little Sissy Cuckold Captions 1    9   2023-06-28  Cute little vulgar captions of and by moi. StungunLullaby <16 fans>   Sprinky Blue Masturbation    6   2023-06-28  A few GIFs of me masturbating on webcam from a few years back now. Comments are welcome as always. Sprinky1985 <3,639 fans>   Sissy Asian Captions ~🎔LeanneLust🎔~ 2    10   2023-06-28  No matter how busy or how much i want to tear myself away from being an asian sissy, it is hard to deny what i deep down. i hope to keep spreading the word and serve white men. leannelustof <484 fans>   I wish I was her and this could happen to me    981   2023-06-27  SubNPassive1 <760 fans>   Thank you Korol_litr for spilling your cum for me    3   2023-06-26  I'm always happy to make your cock cum hard FemboyJessi <1,182 fans>   Me Cindy Cross crossdressing in Nordic blue dance leotard    8   2023-06-25  Me Cindy Cross crossdressing in a Nordic blue dance leotard with matching light blue dance jacket cindy_cross39 <1,669 fans>   Me Cindy Cross crossdressing in purple minidress and silver boot    5   2023-06-23  Me Cindy Cross crossdressing in a sparkly purple mini dress and metallic silver boots. cindy_cross39 <1,669 fans>   Sissy Gif/ Non-Gif Caps 6    40   2023-06-23  emirose2722 <915 fans>   Things I bought online 2     16   2023-06-22  Let’s just say the delivery people have been busy lately Serendipityxx <1,312 fans>   Forced Sissy Husbands    7   2023-06-22  brianmasters67 <1,103 fans>   Camera Fun 13    30   2023-06-22  A new share of selfmade pics. Why is it so teasing to show of and why in women's underwear ?? JanH <1,052 fans>   Sissy playing with dildo’s and filters    27   2023-06-22  Trapaddict 69 <1,809 fans>   Wearing Sexy Bra and Panties     25   2023-06-21  Making cute femboy poses wearing well fitting lingerie. Nice having a D cup chest and a small bald penis being tucked in not showing a bulge leaving only a camel toe. chanhaven56 <67 fans>   New panties     6   2023-06-21  I ordered a bunch of new panties and pvc leggings these arrived yesterday and feel so good I’m going to add pictures wearing them and my other items as they arrive so stay tuned Serendipityxx <1,312 fans>   Feminine Inspiration 31     100   2023-06-21  Serendipityxx <1,312 fans>   Request - New Daddy (a sissy story) ~🎔LeanneLust🎔~     9   2023-06-20  @Belle12 requested some daddy-son captions. One of my fantasies has always been to be adopted, used, and feminized into a white single-daddy's family so i am owned and exclusive to him. this was real fun but it did take some time, hope i it fulfills my... leannelustof <484 fans>   Faggot Andrew Brown in Lingerie, Stockings and Heels    14   2023-06-19  I love getting home, taking off the boy cloths and putting on something sexy txpeter422 <619 fans>   (#2) gay/sissy mind-control captions     5   2023-06-18  I do not own any of the images. I do not condone violence, acts depicted are purely fantasy Amogus <122 fans>   Steffy - the Rubber Doll    116   2023-06-18  Rubber Doll Icon, Fetish Model, Miss Rubber World 2008 os1408 <473 fans>   ABDL femboy/sissy Vol I    11   2023-06-17  some pics of me! empressepicure <163 fans>   Exposed: Sissy Outdoors    10   2023-06-17  Fun in the sun. SCAT WARNING. I did not plan on this but there was some poo in my dirty, stinking butthole. Sorry daddy. I am Your dirty little buttslut. I hope You don't mind? Helen192 <1,166 fans>   Horny     10   2023-06-17  Playing jcjcjc504 <74 fans>   Fisnets and heels    26   2023-06-16  Korol_litr <1,037 fans>   those girls and swimsuits I got crush on it    13   2023-06-16  . lifeguardsissy <497 fans>   My Sexy Women's Underwear    7   2023-06-16  Some of my sexy ladies underwear I love to dress up into, and let everyone see it... BlaiseBalazs <195 fans>   Pink Teddy in the Woods    27   2023-06-15  cameragoods <8,432 fans>   Sissy Asian Captions ~🎔LeanneLust🎔~ 1     10   2023-06-15  Hi everyone! I'm back after trying to escape the reality of being an asian sissy made to serve my WHITE MASTERS. I want to keep spreading the word that all asians only exist to serve BIG. WHITE. COCK leannelustof <484 fans>   Femboy Hooters - Sims 4    20   2023-06-15  SwedishTgirl <212 fans>   sundress harriet sissy crossdressser knickers    6   2023-06-14  its summer...so time to crack out the sundresses :) Harriet93 <269 fans>   A Few Captions Unobscured by Orange Haze    24   2023-06-12  CaptionHook <1,989 fans>   SiSSY CD SAMANTHA 17th SET (PREVIEW GIF of UPCOMING GALLERY)    1   2023-06-11  A preview GIF of my next upcoming gallery. Just a little something to hold you over while waiting for the upload. This one will take a bit of time, but I feel the final set will be well worth it. I go absolutely nuts straddling my favorite dildo and... SexySissySlutS <1,728 fans>   Mature Cds 8    38   2023-06-11  All those lovely gurls demonsaab <681 fans>   Mature Cds 7    38   2023-06-11  Another collection of mature crossdressers demonsaab <681 fans>   Suson Fetish 19    245   2023-06-07  suson sissy nappy diaper abdl fetish pee plastic plasticpanty panty submissive ageplay regression pvc leather latex rubber piss adultbaby ab smooth slippery satin maid sissysuson <272 fans>   Sissy Bianca as bondage slave 3    11   2023-06-07  Fetish sissy loves bondage PVClvr <265 fans>   Mature Cds 5    25   2023-06-07  Gurls will be Gurls... demonsaab <681 fans>   gay/sissy mind control GIF captions    4   2023-06-05  disclaimer: this is purely fantasy, I do not condone violence or non-consensual acts of any kind..... here is a less common subgenre of hypno, where the degradation is mainly on the dom Amogus <122 fans>   Captions-06-05-2023 Unsure    125   2023-06-05  sadsam <4,051 fans>   Sissy Caption Story: Feminine Streamer    33   2023-06-05  thisshouldnote <523 fans>   SISSY CAPTIONS 75: ASIANBOI FASHION!    10   2023-06-05  asians a-are extremely manly c-creatures, b-but that manliness h-has to be worked for! l-luckily for all you asian bois o-out there, i happen to be an expert on outfits that will bring out your inner sissy--i mean SUPERCHAD!!--and scream to the world... FEMINYZE-CAPTI <5,096 fans>   Mature Cds 4    36   2023-06-05  Mpre mature gurls enjoying being gurls demonsaab <681 fans>   Mature Cds 3    36   2023-06-05  More amazing gurls demonsaab <681 fans>   SISSY - GIF'S CAPTIONS - 19    16   2023-06-05  kparc1212 <4,798 fans>   sexy    13   2023-06-04  andyb6 <490 fans>   Mature Cds2    29   2023-06-04  More of my favourite Mature Gurls having fun... demonsaab <681 fans>   Mature Cds    25   2023-06-04  Some of my favourite Mature Gurls looking Gurly demonsaab <681 fans>   Crossdresser in lingerie heels and a tiny cage. Clitty locked up    39   2023-06-04  eoinfromcork <26 fans>   BimboBBC 3(IR/Shemale)    54   2023-06-03  coran25 <2,359 fans>   upskirt surprise 3    21   2023-06-03  Some lovely gurls showing off their wonderful cocks demonsaab <681 fans>   Catboy    12   2023-06-02  Being a cute cat boy with a girl body. Needing tits to fill up my keyhole bra and a pussy for my panties. Also got a flat tummy and a butt. chanhaven56 <67 fans>   Sexy girly time     39   2023-06-02  A couple new outfits the bodysuits are a little small but feel good and hug my body Serendipityxx <1,312 fans>   Femboy    23   2023-06-02  4u gataslindas <2,105 fans>   Barry Bulger    5   2023-06-01  Peterloch <61 fans> :: prev :: | 1 | ... | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | :: next ::