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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    LAST REPOST: PE Bitch-Boy Fashions 2     75   2018-06-02  Final installment of my reposted galleries. This is the second fashion issue (I'm not sure #1 will be reposted) Encounter <797 fans>   First PE Bitch-Boy fashion issue (sissy, XD)    43   2018-09-09  The original lingerie catalog from Prurient Interest. The small size is because these were envisioned as an insert into a larger magazine. Encounter <797 fans>   Sissy adventures... red wig    1   2015-06-20  Siss fun Porntroll <3,664 fans>   Sissy Lovin'    39   2015-02-08  youngndtf <70 fans>   Happy Domm and Fem slut.    10   2013-07-04  wishslut <493 fans>   queen of spades    82   2011-11-30  interracial sissy reddevil19599 <579 fans>   Valery First BBS Fucking at Hotel Ukraine    1   2012-01-06  art-edited RusSketcher at my request valfir22 <3,621 fans>   Queen of spades toons    20   2013-06-22  reddevil19599 <579 fans>   White Bois and Black Men    9   2022-01-18  KaseyTheBoiToy <1,527 fans>   Prurient Interest Ad-book 2014 (sissy sex)    51   2018-06-01  Prurient Encounter's book of sissy motivational adverts Encounter <797 fans>   Classic Prurient Interest fun (sissy, IR)    51   2020-04-04  Something from like seven years ago, they're sort of captions. Really more inspirations and motivations for sissies to get dressed up and get nasty out there. If you see something you like, let me know dahling! Encounter <797 fans>   REPOST: PE Issue #5 (sissy, gloryhole, IR)    51   2021-03-28  Reposted from back in the day: PE #5 in its entirety. A gloryhole heroine followed by a late-night striptease Encounter <797 fans>   REPOST: PE issue #4 (sissy, stocking, IR)    51   2021-03-11  Here is a repost of the fourth PE full issue "Afternoon Exuberance," a story of sweet luv that nevertheless ends in a DAP lol Encounter <797 fans>   Black Rule over Sissy Whitebois    532   2012-03-27  Black Rule over white sissy whitebois alphamalesm <1,407 fans>   Repost: Prurient Encounter Issue #2 (sissy, IR, GB)    39   2021-02-26  Encounter <797 fans>   REPOST: Prurient Encounter issue #3 (sissy, IR, fuck fun)    43   2021-03-04  Here's issue #3 from the old Prurient Encounter series, featuring two sexy stories Encounter <797 fans>   Prurient Encounter Sissy Motivations    19   2018-09-21  Latest special issue from Prurient Interest, interrupted by data probs, so I'm just posting what's finished of it. Possibly you've seen them with different filenames. These are the final versions Encounter <797 fans>   Toon Sissies Love Big Black Cock!    190   2023-10-20  sissyhoon <1,832 fans>   REPOST: PE 14A Season D (sissy, IR, fun)    96   2021-03-08  Here's the 4th season from Prurient Interest's "14-Inch Adventures" Encounter <797 fans>   REPOST: PE 14-Inch Adventures Season G (sissy, IR)    93   2021-04-11  More reposts from the heyday of "Prurient Encounter": here is Season G (stories 37–42), containing all manner of hot slut-bois Encounter <797 fans>   REPOST: PE 14-Inch Adventures Season F (sissy, IR)    91   2021-04-06  Wanted to share more seasons of the Prurient Encounter 14-Inch Adventures series. So here's another! May your stockings be the only straight part on you, dahlings! Encounter <797 fans>   REPOST: PE 14-Inch Adventures Season E (sissy, IR)    91   2021-03-18  Season E of Prurient Encounter's 14-Inch Adventures series, featuring sultry slut-bois in stockings, getting fucked every which way, Encounter <797 fans>   REPOST: Prurient Encounter 14-Inch Adventures Season B (sissy)    97   2021-02-27  Another PE repost, Season B of "14-Inch Adventures" -- feat. all the slut-boi sexytimes you love. This season has three of my BEST stories ever! Encounter <797 fans>   Classic Prurient Encounter 14" Adventures Season A (complete)    95   2021-02-21  Back in the old days, there was Prurient Encounter: slut-boi porn comics. Here's the first "season" complete w/ extra pages. Sissy, IR, DAP, stockings, some pee play. A barrel of laughs Encounter <797 fans>   REPOST: Prurient Encounter 14-Inch Adventures Season C (sissy)    98   2021-03-01  Third season of 14A -- hope you luv! Encounter <797 fans> 1 | 2 | 3 | 4 | 5 | :: next ::