A gallery byNittany Discord with 6165 images, last updated
Size: 650x600 | Tagged: safe, artist:alittleofsomething, edit, editor:watermelon changeling, oc, oc only, oc:cold front, pegasus, pony, bipedal, bow, clothes, crossdressing, derp, dress, exploitable meme, i didn't listen, image macro, lineless, maid, meme, open mouth, simple background, smiling, solo, spread wings, that stallion sure does love dresses
Warning: Some images NSFW

My favorite crossdressing images. 4000+ and counting.

Size: 6000x4500 | Tagged: safe, artist:disty dusk, sky stinger, pegasus, pony, g4, top bolt, absurd resolution, clothes, coronation dress, crossdressing, crown, dress, heart eyes, horseshoes, jewelry, looking at you, male, princess, princess of flying, regalia, smiling, solo, spread wings, stallion, wingding eyes, wings
Size: 4000x3000 | Tagged: safe, artist:cheezedoodle96, big macintosh, cheerilee, earth pony, pony, g4, .svg available, alternate hairstyle, book, bucktooth, clothes, costume, crossdressing, dress, ear piercing, earring, fake teeth, farmer, female, glasses, halloween, hat, jewelry, male, mare, mole, necklace, nightmare night, nightmare night costume, overalls, piercing, redneck, role reversal, scrunchy face, ship:cheerimac, shipping, shirt, simple background, stallion, straight, straw hat, suspenders, svg, teacher, transparent background, vector
Size: 2160x648 | Tagged: safe, artist:meemie7, oc, oc:dr. wolf, oc:goldenfox, oc:keyframe, oc:lady wolf, oc:manga kamen, oc:mimikage, oc:mrs. wolf, oc:sapphire heart song, oc:toonkriticy2k, beauty and the beast, behaving like a cat, bronalysis, brony analyst, clothes, costume, crossdressing, crossover, disney, goldenkey, hissing, kamenheart, nightmare night, nightmare night costume, non-pony oc, red and black oc, the hunchback of notre dame, the little mermaid, wreck-it ralph
Size: 5000x5000 | Tagged: safe, artist:zbowpone, soarin', pegasus, pony, g4, absurd resolution, blushing, clothes, crossdressing, cute, dress, fishnets, frown, girly, looking down, maid, male, old cutie mark, sad, simple background, soarinbetes, solo, stockings, transparent background, vector
Size: 539x553 | Tagged: safe, artist:inlucidreverie, rarity, oc, oc:anon, human, pony, g4, clothes, crossdressing, drawthread, dress, dressup, female, forced makeover, levitation, lolita fashion, looking at each other, looking down, looking up, magic, mare, monochrome, simple background, smiling, telekinesis, white background
Size: 592x561 | Tagged: safe, artist:hetdegon, oc, oc only, oc:mitchy, alicorn, pony, crossdressing, graph paper, male, monochrome, sketch, solo, traditional art
Size: 1322x1600 | Tagged: suggestive, artist:snapplebapps, oc, oc only, oc:snapple, clothes, crossdressing, eyeshadow, hoof polish, lying down, makeup, on back, pillow, relaxing, solo, underhoof, underwear, watermark
Size: 1473x1445 | Tagged: safe, artist:vesperce, oc, oc only, oc:glamataz, unicorn, anthro, unguligrade anthro, cape, clothes, crossdressing, cutie mark, evening gloves, fantasy class, fingerless elbow gloves, fingerless gloves, gloves, leggings, leotard, solo, sorcerer, sparkles, traditional art
Size: 162x186 | Tagged: safe, oc, oc only, oc:short fuse, pony, pony town, animated, crossdressing, femboy, gif, male
Size: 2000x2000 | Tagged: safe, artist:ralek, oc, oc only, oc:ralek, oc:sapphire sights, black widow, griffon, pegasus, pony, spider, arm band, clothes, collar, costume, crossdressing, decoration, dress, gauges, glitter, gun, halloween, high res, joule, lineart, monochrome, offscreen character, piercing, pumpkin bucket, rifle, scared, sequins, sketch, skirt, talking, text, toy gun, tree, trick or treat, tutu, weapon
Size: 1200x1600 | Tagged: safe, artist:causticeichor, oc, oc only, zebra, clothes, crossdressing, duster, looking at you, maid, solo
Size: 554x720 | Tagged: safe, artist:phucknuckl, big macintosh, anthro, g4, crossdressing, male, rocky horror picture show, solo, tattoo
Size: 640x850 | Tagged: safe, artist:kryptchild, snails, g4, clothes, crossdressing, dress, glitter shell, male, solo
Size: 1280x1129 | Tagged: dead source, suggestive, artist:kryptchild, snails, equestria girls, g4, armpits, belly button, cheerleader, clothes, crossdressing, dress, glitter shell, male, male nipples, nipples, one-piece swimsuit, panties, pom pom, shoes, skirt, solo, swimsuit, trap, underwear
Size: 468x900 | Tagged: safe, artist:rayodragon, snails, unicorn, semi-anthro, g4, alternate hairstyle, chinese, clothes, colt, crossdressing, dress, eyeliner, foal, glitter shell, hair bun, makeup, male, solo, trap