Derpibooru
Filters (Default) SettingsRegisterLogin
Viewing gallery Nittany's Crossdressing Extravaganza
Random Image Report Subscribe
A gallery byNittany Discord with 6213 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.

24351
Size: 2362x3544 | Tagged: suggestive, artist:xcinnamon-twistx, oc, oc only, oc:drivel, dracony, dragon, hybrid, apron, ballgag, bdsm, blushing, body pillow, bondage, clothes, commission, crossdressing, gag, leash, lip bite, looking at you, maid, male, one eye closed, rope, socks, solo, solo male, tied up, tongue out, wink, ych result
20250
Size: 1886x807 | Tagged: safe, alternate version, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, oc:train track, human, equestria girls, g4, cancan dancer, clothes, crossdressing, dancing, dress, femboy, high heels, looking at you, makeup, male, shoes, smiling, smiling at you, stockings, store, thigh highs, trio, wig
17190
Size: 1886x807 | Tagged: safe, alternate version, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, human, equestria girls, g4, cancan dancer, clothes, crossdressing, dancing, dress, femboy, high heels, looking at you, makeup, male, shoes, smiling, smiling at you, stockings, store, thigh highs, trio, wig
21260
Size: 1493x1056 | Tagged: safe, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, human, equestria girls, g4, clothes, crossdressing, dancing, dress, femboy, looking at you, makeup, male, smiling, smiling at you, store, trio, wig
26282
Size: 661x935 | Tagged: safe, alternate version, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:petticoat, oc:zaria deibele, equestria girls, g4, bisexual pride flag, bow, clothes, crossdressing, demigirl pride flag, dress, equestria girls-ified, femboy, gay pride, gay pride flag, genderfluid pride flag, high heels, male, pansexual pride flag, park, pride, pride dress, pride flag, shoes, traditional art
1111568
Size: 2376x1665 | Tagged: suggestive, artist:bobthedalek, apple bloom, big macintosh, sugar belle, earth pony, pony, unicorn, g4, :o, apple bloom's bow, atg 2024, bow, bucket, caught, clothes, crossdressing, dress, female, filly, foal, hair bow, horn, lipstick, male, mop, newbie artist training grounds, open mouth, orchard blossom, screaming, ship:sugarmac, shipping, simple background, straight, traumatized, trio, volumetric mouth, white background, wig
47720
Size: 1837x1036 | Tagged: safe, artist:ywra_a, part of a set, pharynx, starlight glimmer, sunburst, thorax, twilight sparkle, alicorn, changedling, changeling, pony, unicorn, g4, blaze (coat marking), changeling x pony, cloak, clothes, coat markings, crossdressing, crown, dress, facial markings, female, flower, folded wings, gay, glasses, holding hooves, horn, jewelry, king thorax, male, mare, marriage, open mouth, prince pharynx, raised hoof, regalia, ribbon, ring, scarf, shipping, socks (coat markings), spread wings, stallion, suit, sunburst's cloak, thoraxburst, twilight sparkle (alicorn), waving, wedding, wedding dress, wedding ring, wings
47710
Size: 1837x1036 | Tagged: safe, artist:ywra_a, part of a set, pharynx, starlight glimmer, sunburst, thorax, twilight sparkle, alicorn, changedling, changeling, pony, unicorn, g4, blaze (coat marking), changeling x pony, cloak, clothes, coat markings, crossdressing, crown, dress, eyes closed, facial markings, female, flower, folded wings, gay, glasses, holding hooves, horn, interspecies, jewelry, king thorax, male, mare, marriage, prince pharynx, raised hoof, regalia, ribbon, ring, scarf, shipping, smiling, socks (coat markings), spread wings, stallion, suit, sunburst's cloak, thoraxburst, twilight sparkle (alicorn), waving, wedding, wedding dress, wedding ring, wings
29443
Size: 2250x1406 | Tagged: safe, artist:paperbagpony, oc, oc only, oc:heroic armour, pony, unicorn, blushing, bow, clothes, crossdressing, dress, gala dress, hair bow, horn, solo, unicorn oc
77986
Size: 1744x3000 | Tagged: safe, artist:jedayskayvoker, king sombra, oc, oc:benjamin terrance tover, earth pony, pony, unicorn, anthro, g4, beautiful, blushing, canon x oc, choker, clothes, crossdressing, date, earth pony oc, elegant, evening dress, fangs, femboy, glasses, gold, horn, long mane, long mane male, looking at each other, looking at someone, looking back, male, sandals, side slit, smiling, thick eyebrows, total sideslit, wholesome
1051432
Size: 1978x2662 | Tagged: suggestive, artist:haokan, oc, oc only, oc:nekonin, alicorn, anthro, unguligrade anthro, adorasexy, alicorn oc, big breasts, blushing, bow, breasts, busty boy, cleavage, clothes, commission, cute, eyebrows, eyebrows visible through hair, femboy, gun, helldivers 2, high res, high-cut clothing, hoodie, horn, intersex, leotard, looking at you, male, mecha, pinup, sexy, simple background, smiling, solo, solo male, weapon, wide hips, wings
1141657
Size: 2276x1514 | Tagged: safe, artist:bobthedalek, starlight glimmer, sunburst, pony, unicorn, g4, atg 2024, bipedal, bunny suit, clipboard, covering, crossdressing, curtains, duo, duo female, eyes on the prize, female, horn, implied trixie, inconvenient trixie, lip bite, magic, magic show, male, male focus, mare, newbie artist training grounds, offscreen character, panicking, playboy bunny, simple background, solo focus, stallion, sweat, sweatdrop, telekinesis, white background
761190
Size: 3800x4500 | Tagged: safe, artist:shadowreindeer, fleur-de-lis, oc, oc:ephraim, deer, pony, unicorn, g4, ;p, blush lines, blushing, bunny suit, clothes, commission, crossdressing, duo, eye clipping through hair, eyebrows, eyebrows visible through hair, female, heart, horn, looking at someone, looking away, male, one eye closed, tongue out, ych result
7810726
Size: 2003x2003 | Tagged: safe, artist:badumsquish, derpibooru exclusive, star tracker, earth pony, pony, skunk, g4, abstract background, alternate hairstyle, antagonist, bandolier, clothes, colored sclera, costume, crossdressing, crossplay, eyelashes, eyeshadow, freckles, frown, gradient background, hoof hold, indigo park (video game), looking back, makeup, male, pants, pose, potion, raised tail, red eyes, ripped pants, salem the skunk, shirt, show accurate, skunk stripe, smiling, smirk, socks, solo, stallion, starcrossed, tail, torn clothes, video game reference, yellow sclera
671009
Size: 2415x2000 | Tagged: safe, artist:bobthedalek, oc, oc only, oc:mixed melody, oc:octavia's father, oc:octavia's mother, oc:ostinato melody, earth pony, pony, apron, atg 2024, bonnet, clothes, crossdressing, dress, duo, newbie artist training grounds, sewing, sewing needle, simple background, stool, sweat, sweatdrops, white background
47660
Size: 2000x2683 | Tagged: source needed, safe, artist:affti, oc, oc only, oc:sweetie swirl, bat pony, anthro, alley, bat pony oc, clothes, crossdressing, detailed background, femboy, fog, gloves, grass, male, school uniform, shoes, skirt, socks, solo, tall
Showing results 1 - 15 of 4049 total