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Free Crossdressing porn pictures 10 25 50 100 150 results per page   Search in this niche: Filter by: Any size Small Medium Large Huge Anytime Today This week This month  Gallery Name   Images   Quality   Added    I am sissy cum slut ;)    5   2017-08-14  I love to be a stupid cumslut for men! Please comment ;) sissybimbobarb <71 fans>   found on the web 7    40   2017-08-14  maiddonna <3,854 fans>   08-14-2017     44   2017-08-14  maiddonna <3,854 fans>   Sexy CD / TV Legs Chastity    21   2017-08-13  Me in hot lingerie and leggins in chastity fatidoas90 <866 fans>   Pissing like a girl in chastity    3   2017-08-13  Pissing like a girl with my little sissy clit in chastity cage fatidoas90 <866 fans>   CDs 51 (out&about)    39   2017-08-13  l_glinski <1,518 fans>   Hard At Work 08: Original Toons by Greggan    24   2017-08-13  More of our magnificent Mansluts earning their keep at Prettybirds Ladies Only Nightclub and Whorehouse. And introducing new boys Ashley and The Boss' own son, Kendra. greggan <1,797 fans>   Hubby Humil Therapy 11    16   2017-08-13  Pathetic prematurely ejaculating husbands submit to the most degrading and humiliating therapy to 'solve' their problem! Boldpuppetmast <4,579 fans>   Hubby Humil 13    16   2017-08-13  Hot housewives humiliate their sexually inadequate husbands, teasing and controlling them, making them do all sorts of degrading things Boldpuppetmast <4,579 fans>   08-13-2017     28   2017-08-13  maiddonna <3,854 fans>   Feminization Captioned: DressupTeas: Vol.01    24   2017-08-13  thanks to all original creators Alertme1159 <6,261 fans>   Sweet TV's 69    89   2017-08-13  Kristin_crossd <3,972 fans>   Tiffany Devonshire (Amateur Tgirl)    54   2017-08-13  aliciat <10,405 fans>   Felicia Cordalis 1 (Amateur Tgirl)    132   2017-08-13  aliciat <10,405 fans>   Marina Lin 1 (Amateur Tgirl)    115   2017-08-13  aliciat <10,405 fans>   Jodie XFemme 1 (Amateur Tgirl)    121   2017-08-13  aliciat <10,405 fans>   Aline Travestie (289)     20   2017-08-13  Aline travestie en lingerie aline_trav <1,461 fans>   Stuff    4   2017-08-13  Hot Booty in leggings SlutNicoleAnal <17 fans>   SISSY DESIRES 263    48   2017-08-13  lauritacd_tv <4,810 fans>   Humiliated Sissy Fags 19.    20   2017-08-12  Sissy Slut San <5,131 fans>   Snow White Sucks Cock    10   2017-08-12  On the site where I found these the model was identified as Lucy Robbins. archistyr <7,246 fans>   Terri, Mature TV Loves BBC    20   2017-08-12  archistyr <7,246 fans>   Crossdressers, TG's and boys    21   2017-08-12  Bobbel82 <440 fans>   Russian Fag-Lady Valery spreads legs for fuck-buddies    67   2017-08-12  valfir22 <3,941 fans>   08-12-2017     48   2017-08-12  maiddonna <3,854 fans>   Lovely Mature T Girls I Like    72   2017-08-12  archistyr <7,246 fans>   Hot TVs & CDs Out and About in Public    58   2017-08-12  archistyr <7,246 fans>   小さいチンポ08    16   2017-08-12  30ml <218 fans>   小さいチンポ07    17   2017-08-12  30ml <218 fans>   SISSY DESIRES 262    48   2017-08-12  lauritacd_tv <4,810 fans>   LaceyLovesCD Black Flower Print Satin Thong    56   2017-08-12  Satin thong from Goodwill. LaceylovesCD <4,041 fans>   LaceyLovesCD Angelas Bikini    88   2017-08-12  One of my daughters friend moved in for a short time due to family issues.SO,I decided to play in her sexy bikini.I also have pictures of me wearing her satin panties which I will post soon. LaceylovesCD <4,041 fans>   LaceyLovesCD Do Me In Denim Part 2    41   2017-08-12  LaceylovesCD <4,041 fans>   LaceyLovesCD Do Me In Denim Part 1    12   2017-08-12  LaceylovesCD <4,041 fans>   Chiffon party dress (part 1)    29   2017-08-11  Here I am in a summery chiffon party dress. I particularly liked the way the fabric drapes around my cock. Made me feel so good I had to play with it for a while. But what I really want to do in this dress is to piss in it and on it, so stay tuned... EdieCD <1,619 fans>   Dawn 2 (Fat Amateur Tgirl)    86   2017-08-11  aliciat <10,405 fans>   Ashley Maybee 2 (Amateur Tgirl)    104   2017-08-11  aliciat <10,405 fans>   Hanna Griffiths 3 (Amateur Tgirl)    125   2017-08-11  aliciat <10,405 fans>   Crossdressers wearing heavy makeup 138    100   2017-08-11  aliciat <10,405 fans>   08-11-2017     30   2017-08-11  maiddonna <3,854 fans>   Feminization Transformation Captions 15    24   2017-08-11  Captions involving feminization and transformation, either by chemical, hypnosis or magic. girlyapril <763 fans>   transvestite on transvestite 97    73   2017-08-10  Kristin_crossd <3,972 fans>   me and real people 08    28   2017-08-10  i need your comment. please. wlodja <366 fans>   Sweet TV's 68    82   2017-08-10  Kristin_crossd <3,972 fans>   Me 2017 (2)    27   2017-08-10  SluttyDirtyPig <146 fans>   Having a Girly Moment LOL    57   2017-08-10  grafter69 <7,899 fans>   My Pretty Pantied Piss    25   2017-08-10  taste my nectar.... rock345 <2,594 fans>   08-10-2017     35   2017-08-10  maiddonna <3,854 fans>   CDS anal SHEMALE ETORTIC GALLERY    1   2017-08-10  CDS COLLECTION cdmina33 <418 fans>   Asian Shemale Ladyboy Newhalf Makina Hoshinome    33   2017-08-10  Cute Japanese Trans Shemale Makina posing, fucked, and sucking cock. chapchapchap <231 fans>   Shy sissy with ponytail    2   2017-08-10  southsidetrixi <47 fans>   Satin Panty Encouragement 176    20   2017-08-10  Captions of girls encouraging you to wear satin panties, slips, pantyhose and party dresses. s1var7 <1,296 fans>   Tifany sissy 2017 bra and panty shots    16   2017-08-10  Tifanysissy <684 fans>   Asian Newhalf Shemale Tranny Miu Sakuragi    17   2017-08-10  Sexy Japanese trans newhalf Miu Sakuragi chapchapchap <231 fans>   Hot Little Submissive Trap ( anyone know her name?)    4   2017-08-09  pancho012 <240 fans>   32yo MILF - I'm sucking hubby's cock deep    6   2017-08-09  He's lately wearing womens panties nearly everyday. I still have to get used to that, but to be honest it somehow turns me on to see him in nice sheer underwear. PAWG_Milf <9,272 fans>   CDs 50 (50 maids)    50   2017-08-09  l_glinski <1,518 fans>   Satana Kennedy 1 (Amateur Tgirl)    108   2017-08-09  aliciat <10,405 fans>   Kelly Catherine Tyler 1 (Amateur Tgirl)    160   2017-08-09  aliciat <10,405 fans>   Johanna Joya 1 (Amateur Tgirl)    125   2017-08-09  aliciat <10,405 fans>   Summer dressing    7   2017-08-09  krissynyc <961 fans>   08-09-2017     30   2017-08-09  maiddonna <3,854 fans>   Sissy slut    7   2017-08-09  sissysubinka <102 fans>   Jamie in and out of her pink dress    36   2017-08-09  Jamie loves her pink dress, but can't wait to get out of it1 JamieJames <1,787 fans>   Jamie's latest load of panties    100   2017-08-09  Jamie's newest set of panties, all sorts! Thongs, Grannies, and all sorts n between. Some sexy, some less so. Some lacy, others plainer. JamieJames <1,787 fans>   Trannies Sissies & Bi Bios     40   2017-08-09  underherboots <4,046 fans>   take me as your bride    5   2017-08-09  adrian1990 <201 fans>   High Heels And Lace    14   2017-08-09  Destiny_cd <1,781 fans>   Private parts    4   2017-08-08  Batalbat <79 fans>   Pretty gurls that make my 'juices' flow    24   2017-08-08  ivorg <2,104 fans>   Secretary in Charge 01    16   2017-08-08  Sexy secretaries dominate and abuse their pathetically horny wimpy bosses Boldpuppetmast <4,579 fans>   Sissy Faggot Valery expose for Mistress_JEZZ    12   2017-08-08  valfir22 <3,941 fans>   08-08-2017     33   2017-08-08  maiddonna <3,854 fans>   Hottest Tranny in Webcam    2   2017-08-08  tscam4free69 <191 fans>   Satin Panty Encouragement 175    20   2017-08-08  Captions of girls encouraging you to wear satin panties, slips, pantyhose and party dresses. s1var7 <1,296 fans>   Panties and my Sissypussy Aug.7th,2017    19   2017-08-07  dallastx52m <8,914 fans>   Be a Sissy - GIFS 5    6   2017-08-07  Poule <1,202 fans>   Aline Travestie (288)    20   2017-08-07  Aline travestie en lingerie aline_trav <1,461 fans>   Samantha Fevrier 2 (Amateur Tgirl)    137   2017-08-07  aliciat <10,405 fans>   Emilie La Nuit 3 (Amateur Tgirl)    87   2017-08-07  aliciat <10,405 fans>   Sissy Crossdressing Captions 39    32   2017-08-07  aliciat <10,405 fans>   my face for fakes, tributes and humiliation    13   2017-08-07  wlodja <366 fans>   Gothic gurl    42   2017-08-07  Free for fakes and tributes. wlodja <366 fans>   Tracey Receives the Slipper from Miss    8   2017-08-07  Tracey goes Over the Knee for a long overdue Slippering from Miss TraceyCD1963 <1,466 fans>   Random for fakes    55   2017-08-07  Fake request. Please comment. ) wlodja <366 fans>   08-07-2017     33   2017-08-07  maiddonna <3,854 fans>   August upload    15   2017-08-07  scarlettslutbo <4,474 fans>   me in white panties    31   2017-08-07  macybottoms <7 fans>   Marietta Part 2    13   2017-08-07  Petite histoire de prise en main conjugale. female-suprema <682 fans>   Marietta Part 1    17   2017-08-07  Petite histoire de prise en main conjugale. female-suprema <682 fans>   A few more :) - SissysarahHH    11   2017-08-07  SissySarahHH <1,264 fans>   小さいチンポ06    16   2017-08-07  30ml <218 fans>   小さいチンポ05    20   2017-08-07  30ml <218 fans>   DRESSED FOR THE OCCASION    50   2017-08-06  One of my favorite fantasies is dressing and providing pleasure for a man or group of men. Kneeling and sucking cock as others watch, submitting anally bareback of course or being spit roasted taking cock ass to mouth. allmyfantasies <693 fans>   Shemales,Tgirls,Cd's    33   2017-08-06  Roses cuck <6,306 fans>   Shemales,Tgirls,Cd's    158   2017-08-06  Roses cuck <6,306 fans>   Wet Swimsuit LOL    27   2017-08-06  grafter69 <7,899 fans>   08-06-2017    47   2017-08-06  maiddonna <3,854 fans>   The Feminization of Misty    8   2017-08-06  TOSissySlutLil <120 fans>   Contos T 0 - 11    538   2017-08-06  Eros83 <372 fans>   Feminization Transformation Captions 14    24   2017-08-05  Captions involving feminization and transformation, either by chemical, hypnosis or magic. girlyapril <763 fans>   小さいチンポ04    23   2017-08-05  30ml <218 fans>   Mya St Clair 1 (Amateur Tgirl)    68   2017-08-05  aliciat <10,405 fans>   Tammy Gal (Amateur Tgirl)    121   2017-08-05  aliciat <10,405 fans>   Miisu Miisulainen 1 (Amateur Tgirl)    82   2017-08-05  aliciat <10,405 fans>   Kerry May 1 (Amateur Tgirl)    133   2017-08-05  aliciat <10,405 fans>   Lick my Mushroom Head    55   2017-08-05  grafter69 <7,899 fans>   Pretty Sissy Hanna 2    24   2017-08-05  Hanna is such a sweet, submissive, obedient, lovely sissy girl! She stole my heart but alas, we live oceans apart so she can only be alive in my dreams... DaddyMaster <87 fans>   Pantyhose    21   2017-08-05  Closet--CDgurl <1,407 fans>   Sissy Wet Dreams VII Ch. 14    20   2017-08-05  Wonderful, sissy stories, fantasies and captions!!  lilsissyhanna <1,669 fans>   Sissy Misc. (13)    24   2017-08-05  Cowboymeisje <368 fans>   08-05-2017     48   2017-08-05  maiddonna <3,854 fans>   Weenies in bikinis    20   2017-08-05  Sweetie gurls with adorable clitties and pussycunnies inside their bikinis. cherrylipsbaby <12,053 fans>   Chastity GIFs     12   2017-08-05  underherboots <4,046 fans>   a black garter and sheer bikinis    12   2017-08-05  nylon and metallic stockings were also used in the work awickedweaseli <2,080 fans>   My Blue Pantied Cock And Ass    10   2017-08-05  enjoy my flowers rock345 <2,594 fans>   RP    3   2017-08-05  kathicd <512 fans>   LaceyLovesCD Made In America 2016    123   2017-08-05  LaceylovesCD <4,041 fans>   Here2cum Black Stockings Crotchless Panties ( Please Comment And    20   2017-08-05  Here2cum Various Poses For Tributes And Degrading Comments Here2cum <779 fans>   Crossdress-persian-sissyboy-    142   2017-08-05  Solmazzanposh <312 fans>   Transvestite Denise    8   2017-08-04  TRANSVESTITE TRANSEXUAL TGIRL TRAP CROSSDRESSER CROSSDRESSING SISSY Speedwell <541 fans>   Transvestite Louise    36   2017-08-04  TRANSVESTITE TRANSEXUAL TGIRL TRAP CROSSDRESSER CROSSDRESSING SISSY Speedwell <541 fans>   Transvestite Jenny 2    62   2017-08-04  TRANSVESTITE TRANSEXUAL TGIRL TRAP CROSSDRESSER CROSSDRESSING SISSY Speedwell <541 fans>   Transvestite Jenny 1    80   2017-08-04  TRANSVESTITE TRANSEXUAL TGIRL TRAP CROSSDRESSER CROSSDRESSING Speedwell <541 fans>   Pantys my wife.    6   2017-08-04  calipsa <1,344 fans>   08-04-2017    32   2017-08-04  maiddonna <3,854 fans>   Hairless with corset chasity urethral anal lock    22   2017-08-04  willie_ <602 fans>   Schoolgirl pantyhose 22    7   2017-08-04  Private schoolgirl in sheer black pantyhose XXX KatrinaFayre76 <737 fans>   sexy    8   2017-08-04  sexy sissy showing off cute ass sexysissyp <0 fans>   man suck TS 68    24   2017-08-03  thomicard <2,677 fans>   TS fuck man 24    24   2017-08-03  thomicard <2,677 fans>   Ilse`s July Pics    64   2017-08-03  Hi friends here are this bunch of pictures I`ve made in July, Hope you like them!! Your Ilse. Hola amigos estas fotitos hice en Julio, Bueno, hice varias mas, ya veran Ojala les gusten Kisses Besos Ilsecross <1,271 fans>   Sarah Jackson 2 (Amateur Tgirl)    93   2017-08-03  aliciat <10,405 fans>   Cindy Hants 2 (Amateur Tgirl)    134   2017-08-03  aliciat <10,405 fans>   Men helping crossdressers to dress 27    53   2017-08-03  aliciat <10,405 fans>   Crossdressers wearing heavy makeup 137    102   2017-08-03  aliciat <10,405 fans>   Crossdressers 43    39   2017-08-03  submissivemale <2,860 fans>   Had a spare hour to kill LOL    47   2017-08-03  grafter69 <7,899 fans>   08-03-2017    33   2017-08-03  maiddonna <3,854 fans>   Sissy Rhiannon Random Pics    11   2017-08-03  rtest07 <2,248 fans>   Chastity     11   2017-08-03  Itsjustme6969 <110 fans>   小さいチンポ03    29   2017-08-02  30ml <218 fans>   小さいチンポ02    18   2017-08-02  30ml <218 fans>   小さいチンポ01    10   2017-08-02  30ml <218 fans>   Sissy me    4   2017-08-02  Sissiphus <67 fans>   Sissy me    3   2017-08-02  Sissiphus <67 fans>   Expose Roy Bourne    4   2017-08-02  JenniferAnn2 <39 fans>   Please out Roy Bourne - spread pics    3   2017-08-02  JenniferAnn2 <39 fans>   BBW Sissy Diane - August 2017 Pics    21   2017-08-02  DianeL <3,232 fans>   BBW Sissy Diane - August 2017 Smoking pics    17   2017-08-02  DianeL <3,232 fans> :: prev :: | 1 | ... | 535 | 536 | 537 | 538 | 539 | 540 | 541 | 542 | 543 | 544 | :: next ::