Derpibooru
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Viewing gallery Sissy
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A gallery byTomboom with 86 images, last updated
Size: 620x509 | Tagged: explicit, artist:denton, pony, balls, clothes, crossdressing, dildo, dock, femboy, fleshlight, frog (hoof), lace, male, nudity, panties, penetrable sex toy, penis, sex toy, sissy, sissyfication, solo, solo male, underhoof, underwear
1341753
Size: 992x1346 | Tagged: suggestive, artist:sip, oc, oc only, oc:arcshine, pony, blushing, bow, butt, clothes, crossdressing, crotch bulge, dialogue, dock, dress, implied twilight sparkle, looking back, maid, maid headdress, male, offscreen character, open mouth, panties, plot, skirt, socks, solo, solo male, speech bubble, stallion, striped socks, tail, underwear, upskirt
10414310
Size: 878x984 | Tagged: suggestive, artist:kill joy, oc, oc only, pegasus, pony, abdl, blushing, clothes, collar, crossdressing, diaper, diaper fetish, fetish, gambling, glasses, non-baby in diaper, offscreen character, onesie, pet tag, poofy diaper, sissy, socks, solo, striped socks, tutu
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