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Viewing gallery Nittany's Crossdressing Extravaganza
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A gallery byNittany Discord with 6175 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.

54781
Size: 1221x1772 | Tagged: safe, artist:ladysdino, princess celestia, oc, oc:dreamy daze, alicorn, pegasus, anthro, plantigrade anthro, g4, bowser, cake, cakelestia, canon x oc, chase, clothes, costume, crossdressing, crossover, crossplay, dreamlestia, female, food, male, princess peach, shipping, straight, super mario bros.
61912
Size: 5600x10165 | Tagged: source needed, safe, artist:almond evergrow, artist:suchalmy, oc, oc:stryker, pegasus, anthro, absurd resolution, arm behind head, clothes, crossdressing, femboy, leg warmers, looking at you, male, skirt, solo
10170
Size: 184x228 | Tagged: safe, oc, oc only, oc:sugarcube, pony, sheep, pony town, animated, crossdressing, femboy, gif, horns, male, pixel art, simple background, solo, transparent background, trotting
1041481
Size: 3400x5100 | Tagged: source needed, suggestive, artist:kloudmutt, oc, oc only, oc:sweetie swirl, bat pony, anthro, bat pony oc, blue blush, blushing, clothes, crossdressing, dress, ear fluff, femboy, gloves, hair over one eye, high heels, jessica rabbit dress, long gloves, looking at you, male, multicolored hair, open-back dress, red dress, shoes, side slit, simple background, sitting, solo, solo male, strapless dress, table, thighs, thunder thighs, total sideslit, trap, wide hips
23350
Size: 873x1199 | Tagged: safe, artist:lightningbolt, derpibooru exclusive, pegasus, pony, g4, .svg available, alex gaskarth, all time low, belt, buckle, chains, cheek fluff, choker, clothes, crossdressing, dyed mane, dyed tail, ear fluff, ear piercing, earring, fishnet stockings, hair over one eye, heels on a horse, high heels, hoof fluff, jewelry, leg band, lidded eyes, male, mary janes, midriff, necklace, piercing, ponified, raised hoof, shirt, shoes, short shirt, show accurate, simple background, skirt, smiling, solo, spread wings, stallion, standing, svg, tail, tail feathers, tattoo, transparent background, vector, wing fluff, wings
15190
Size: 1061x1500 | Tagged: suggestive, artist:bucked, oc, oc:alex carter, oc:crashing thunder, anthro, clothes, crossdressing, cute, dancing, femboy, gay, male, military, panties, romance, romantic, royal guard, strings, underwear
18234
Size: 873x1199 | Tagged: safe, artist:lightningbolt, derpibooru exclusive, pegasus, pony, g4, .svg available, alex gaskarth, all time low, belt, buckle, chains, cheek fluff, choker, clothes, crossdressing, dyed mane, dyed tail, ear fluff, ear piercing, earring, eyeliner, eyeshadow, fishnet stockings, hair over one eye, high heels, hoof fluff, hoof polish, jewelry, leg band, lidded eyes, lipstick, makeup, male, mascara, midriff, necklace, piercing, ponified, raised hoof, shirt, shoes, short shirt, show accurate, simple background, skirt, smiling, solo, spread wings, stallion, standing, svg, tail, tail feathers, tattoo, transparent background, vector, wing fluff, wings
69903
Size: 2904x4000 | Tagged: safe, artist:tatemil, oc, oc:felixe sky, anthro, clothes, crossdressing, dress, femboy, high heels, horns, maid, male, shoes, socks, solo, thigh highs
50824
Size: 2047x1575 | Tagged: safe, artist:liaaqila, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, equestria girls, g4, bow, clothes, crossdressing, dress, evening gloves, femboy, floral head wreath, flower, flower girl, flower girl dress, gloves, long gloves, male, poofy shoulders, princess daisy, princess peach, princess rosalina, rosalina, simple background, super mario bros., traditional art, transgender, trio, white background
15261
Size: 1560x2321 | Tagged: safe, artist:tikibat, oc, oc:file folder, pegasus, pony, clothes, crossdressing, fishnet stockings, glasses, high heels, male, shoes, simple background, solo, stallion, transparent background
681228
Size: 632x719 | Tagged: safe, anonymous artist, artist:pastthesouthpole, night light, twilight sparkle, pony, unicorn, g4, /mlp/ tf2 general, angry, book, calendar, crossdressing, cyrillic, heavy weapons guy, reading, russian, team fortress 2, translated in the comments
446513
Size: 3130x2141 | Tagged: safe, artist:ghostpikachu, oc, oc only, oc:autumn rosewood, oc:dreaming star, bat pony, bat pony unicorn, hybrid, pegasus, pony, unicorn, base used, bat pony oc, bipedal, blushing, clothes, crossdressing, cute, dress, eyelashes, fake eyelashes, fangs, femboy, feminine stallion, girly, happy, high res, horn, indoors, looking at you, makeup, male, ocbetes, pegasus oc, red eyes, ribbon, skirt, socks, stallion, striped socks, unicorn oc, wings
1051540
Size: 2000x3000 | Tagged: source needed, safe, artist:artaraxia, oc, oc only, oc:sweetie swirl, bat pony, anthro, chest fluff, clothes, dress, ear piercing, eyelashes, femboy, gloves, hair over one eye, high heels, high res, jessica rabbit dress, lipstick, long gloves, makeup, male, multicolored hair, open-back dress, piercing, red dress, shoes, side slit, simple background, solo, strapless dress, thighs, thunder thighs, total sideslit, wide hips
761143
Size: 2421x1641 | Tagged: suggestive, artist:bobthedalek, oc, oc only, oc:mixed melody, oc:octavia's father, oc:octavia's mother, oc:ostinato melody, earth pony, pony, cleaning, clothes, crossdressing, duster, ladder, maid, vase
1842734
Size: 1200x1200 | Tagged: safe, artist:cold-blooded-twilight, spike, dragon, g4, chinese dress, clothes, crossdressing, dress, fangs, fire, happy new year 2024, magic, raised leg, wide hips, year of the dragon
29433
Size: 1800x2400 | Tagged: safe, artist:sixes&sevens, thunderlane, pegasus, anthro, g4, clothes, crossdressing, dress, evening gloves, eyeshadow, gloves, jewelry, long gloves, looking at you, makeup, male, necklace, smiling, stallion
45756
Size: 2042x2043 | Tagged: safe, artist:liaaqila, derpibooru exclusive, oc, oc only, oc:mysti inferno, oc:precious gemstones, human, equestria girls, g4, blue hair, clothes, crossdressing, dress, femboy, high heels, high res, makeup, male, mirror, red hair, shoes, simple background, table, traditional art, vanity, white background
Showing results 46 - 60 of 4017 total