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Viewing gallery Nittany's Crossdressing Extravaganza
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A gallery byNittany Discord with 6183 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.

12518738
Size: 3511x1977 | Tagged: safe, artist:badumsquish, derpibooru exclusive, star tracker, earth pony, pony, g4, alternate hair color, alternate hairstyle, blush sticker, blushing, checkered floor, clothes, cosplay, costume, crossdressing, crossover, crossplay, freckles, hat, jester, jester hat, jester outfit, looking at you, male, pomni, shoes, show accurate, sitting, solo, stallion, starcrossed, the amazing digital circus, this will end in insanity, thousand yard stare, wide eyes
781164
Size: 3976x3476 | Tagged: safe, artist:rrd-artist, oc, oc only, oc:midnight lancer, pegasus, pony, 2023, blushing, cathedral, clothes, crossdressing, cute, dress, embarrassed, high res, jewelry, looking at you, male, nervous, regalia, scenery, scenery porn, signature, solo, stallion
19220
Size: 3264x2040 | Tagged: safe, artist:peternators, oc, oc only, oc:heroic armour, pony, unicorn, blushing, clothes, colt, crossdressing, dress, floppy ears, foal, high res, male, mary janes, monochrome, shoes, sketch, socks, thigh highs, traditional art
11201
Size: 2000x2000 | Tagged: suggestive, artist:endelthepegasus, oc, oc:endel frostlion, anthro, plantigrade anthro, clothes, crotch bulge, femboy, fishnet stockings, floppy ears, high res, looking at you, male, one eye closed, open mouth, outfit, piercing, simple background, sketch, solo, solo male, stockings, thigh highs, wings
58790
Size: 890x890 | Tagged: safe, alternate version, artist:erieillustrates, discord, fluttershy, draconequus, pegasus, pony, g4, action lines, anime, clothes, cosplay, costume, couple, crossdressing, crossplay, crown, eyes closed, faint, female, flower, glasses, horns, jewelry, male, mare, open mouth, otakushy, regalia, revolutionary girl utena, rose, ship:discoshy, shipping, spread wings, straight, tail, wings
19250
Size: 4000x5000 | Tagged: safe, artist:dashingjack, oc, oc:brainstorm, oc:wintergreen, earth pony, pony, bipedal, blushing, body control, clothes, crossdressing, dancing, leotard, magic, magic aura, male, showgirl, stallion
33562
Size: 1415x1726 | Tagged: suggestive, artist:sexygoatgod, oc, oc only, earth pony, anthro, clothes, commission, crossdressing, femboy, feminization, finished commission, forced feminization, goth, male, simple background, socks, striped socks, transparent background
18250
Size: 4000x4661 | Tagged: safe, artist:creedyboy124, oc, oc only, oc:shane park, pegasus, pony, g4, blushing, clothes, crossdressing, dress, embarrassed, male, simple background, solo, stallion, transparent background
771122
Size: 1526x1211 | Tagged: safe, artist:arllistar, oc, oc only, oc:bytewave, oc:caramel sweet, pegasus, pony, unicorn, bed, bedroom, blurry background, blushing, clothes, collar, commission, crossdressing, garters, gay, hoodie, horn, leash, maid, male, pegasus oc, raised hoof, sitting, socks, stockings, striped socks, thigh highs, unicorn oc, unshorn fetlocks, ych result
751052
Size: 1526x1211 | Tagged: safe, artist:arllistar, oc, oc only, oc:bytewave, oc:caramel sweet, pegasus, pony, unicorn, bed, bedroom, blurry background, blushing, clothes, collar, commission, crossdressing, garters, gay, hoodie, horn, leash, maid, male, pegasus oc, raised hoof, sitting, socks, stockings, thigh highs, unicorn oc, unshorn fetlocks, ych result
1101492
Size: 973x1200 | Tagged: suggestive, artist:lunarlacepony, oc, oc:blake, griffon, anthro, black panties, clothes, crossdressing, femboy, griffon oc, high heels, maid, maid headdress, male, shoes, skirt, solo, upskirt
34540
Size: 2331x2142 | Tagged: safe, artist:arwencuack, oc, oc:arwencuack, oc:nekonin, alicorn, pegasus, sylveon, vulpix, anthro, ><, arm hooves, clothes, crossdressing, crying, evil, evil laugh, eyes closed, female, femboy, food, high res, laughing, maid, male, pokémon, sandwich, simple background, sketch, transparent background
64890
Size: 1856x2986 | Tagged: safe, artist:valcanicwitch, oc, oc only, oc:nekonin, alicorn, anthro, :d, breasts, busty boy, clothes, crossdressing, dress, femboy, futuristic, garter belt, high heels, intersex, male, open mouth, open smile, shoes, simple background, smiling, sneakers, solo, stockings, thigh highs, trap, white background, wide hips
12114
Size: 3200x5000 | Tagged: safe, artist:nine the divine, oc, oc only, oc:nine the divine, anthro, clothes, crossdressing, school uniform, simple background, solo, transparent background
1431816
Size: 2000x2465 | Tagged: safe, artist:sirzi, smolder, spike, oc, dragon, pony, g4, blushing, casual nudity, clothes, clothes swap, commission, crossdressing, dragoness, embarrassed, female, folded wings, high res, looking at you, looking down, looking sideways, loose fitting clothes, male, male swimwear challenge, nudity, ocean, one-piece swimsuit, partially submerged, surfing, surprised, swimming trunks, swimsuit, swimsuit swap, tight clothing, water, wave, we don't normally wear clothes, winged spike, wings, wipeout
57786
Size: 2181x2180 | Tagged: safe, artist:liaaqila, oc, oc only, oc:bsod, oc:cold front, oc:disty, equestria girls, g4, bow, clothes, commission, crossdressing, dress, dressing, equestria girls-ified, evening dress, femboy, high heels, high res, makeover, male, shoes, smiling, traditional art
1281761
Size: 4200x2585 | Tagged: suggestive, artist:taleriko, oc, oc:shadow, unicorn, anthro, clothes, crossdressing, eyeshadow, femboy, garter belt, garter straps, goth, makeup, male, platform boots, skirt, solo, stockings, thigh highs, zettai ryouiki
Showing results 106 - 120 of 4022 total