Derpibooru
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Viewing gallery Nittany's Crossdressing Extravaganza
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A gallery byNittany Discord with 6204 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.

861172
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
1011516
Size: 2276x1514 | Tagged: suggestive, 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
721110
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
729726
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
61949
Size: 2415x2000 | Tagged: suggestive, 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
45640
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
30480
Size: 1920x2400 | Tagged: source needed, safe, artist:mayerrr mayerrr, oc, oc only, bat pony, bat pony oc, blue blush, blushing, clothes, crossdressing, duster, ear fluff, femboy, floating heart, heart, maid, male, multicolored hair, solo, sparkles, text
31403
Size: 1558x2780 | Tagged: safe, artist:hayley566, oc, oc only, oc:azure/sapphire, equestria girls, g4, clothes, crossdressing, femboy, genderfluid pride flag, headband, high heels, male, pansexual pride flag, pride, pride dress, pride flag, pride month, shoes, simple background, solo, stockings, thigh highs, transparent background, wig
46754
Size: 1280x960 | Tagged: safe, oc, oc only, oc:prince whateverer, pegasus, pony, galacon, clothes, crossdressing, duster, galacon 2024, irl, maid, male, photo, plushie, stallion
17220
Size: 1280x1196 | Tagged: safe, artist:asklevee, oc, oc only, oc:levee, earth pony, pony, clothes, concave belly, crossdressing, fake wings, gradient background, lanky, long legs, male, see-through, skinny, skirt, solo, stallion, sternocleidomastoid, tall, thin
791042
Size: 3500x4000 | Tagged: safe, alternate version, artist:spoopygander, oc, oc only, oc:geoplix, draconequus, semi-anthro, chest fluff, clothes, collar, countershading, crossdressing, dress, ear piercing, piercing, signature, socks, solo, stockings, thigh highs, wing piercing, wings
18260
Size: 1872x1692 | Tagged: suggestive, artist:sutibaruart, oc, oc only, oc:basil, oc:monique, anthro, breasts, clothes, crossdressing, crotch bulge, dancing, dress, duo, female, furry, furry oc, high heels, male, shoes, simple background, unexpected, white background
9111
Size: 3242x4624 | Tagged: safe, artist:acid flask, oc, oc only, oc:film wheel, pegasus, anthro, 2d, bisexual, clothes, crossdressing, dress, embarrassed, gown, long hair, long tail, looking at you, male, pegasus oc, tail, talking, text, traditional art
42600
Size: 2944x4384 | Tagged: safe, artist:askhypnoswirl, oc, oc only, oc:guard cobalt flash, bat pony, bat pony oc, clothes, club, femboy, latex, latex socks, male, midriff, phone, reading, sitting, socks, solo, stallion
42633
Size: 598x1000 | Tagged: safe, artist:skylarpalette, oc, oc only, oc:blitz streak, hippogriff, pony, adorable face, blushing, bow, cheek fluff, clothes, crossdressing, crossed legs, cute, ear blush, ear fluff, fluffy, frills, hair bow, looking back, maid, male, png, shoes, shy, simple background, skirt, socks, solo, stallion, stockings, talking, talons, thigh highs, transparent background, wings
27484
Size: 1624x1260 | Tagged: safe, artist:paperbagpony, oc, oc:stardust(cosmiceclipse), bat pony, pony, bow, clothes, crossdressing, dress, ear piercing, earring, eyeshadow, femboy, gala dress, girly, grin, hair bow, hoof shoes, jewelry, makeup, male, piercing, raised hoof, smiling, stallion
Showing results 1 - 15 of 4040 total