Showing Gallery - Derpibooru

Rainbow Rocks 10th Anniversary - Let's celebrate the 10th anniversary of Rainbow Rocks with an art event! Here

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: 4608x4154 | Tagged: safe, artist:damlanil, oc, oc:chloe adore, oc:ferb fletcher, pegasus, pony, unicorn, bdsm, bodysuit, boots, bound wings, clothes, collar, commission, costume, disembodied head, disguise, dominant, dressing, duo, eyeshadow, female, gloves, high heel boots, high heels, horn, latex, latex boots, latex gloves, latex socks, latex suit, leotard, lipstick, makeup, male, mare, mask, masking, ponysuit, raised hoof, rubber, rubber suit, shiny, shoes, show accurate, simple background, skintight clothes, socks, stallion, suit, transparent background, vector, wings

Size: 3000x3200 | Tagged: safe, artist:k0potb, oc, oc only, earth pony, pony, collar, commission, crossdressing, femboy, high res, male, solo

Size: 2560x2476 | Tagged: safe, alternate character, alternate version, artist:arwencuack, oc, oc only, oc:bizarre song, pegasus, anthro, commission, crossdressing, female, heart, heart eyes, high res, solo, wingding eyes, ych result, zoom layer

Size: 1094x1210 | Tagged: safe, artist:pony quarantine, oc, oc only, oc:anon stallion, oc:jargon scott, earth pony, human, pony, bridal carry, cap, carrying, clothes, crossdressing, dress, female, floppy ears, glasses, grayscale, hat, human female, maid, male, monochrome, pen drawing, rule 63, smiling, stallion, traditional art, trucker hat

Size: 4000x4000 | Tagged: safe, artist:spiroudada, oc, oc:dolly hooves, pony, unicorn, bow, clothes, cold, cute, dress, ice, night, scratches, shoes, solo, winter

Size: 2000x2000 | Tagged: safe, artist:jubyskylines, oc, oc only, oc:juby skylines, pegasus, pony, blushing, clothes, crossdressing, ear fluff, embarrassed, high res, lidded eyes, limited palette, looking at you, looking back, looking back at you, maid, male, pegasus oc, simple background, sitting, solo, stallion, white background, wings

Size: 1298x1112 | Tagged: safe, artist:paperbagpony, oc, oc only, oc:stardust(cosmiceclipse), bat pony, bat pony oc, bow, clothes, crossdressing, dress, eyeshadow, femboy, hair bow, makeup, male, solo, stallion

Size: 1280x681 | Tagged: suggestive, artist:koportable, soarin', pegasus, pony, g4, bench, blushing, clothes, clothing theft, cloud, comic strip, crossdressing, dialogue, female, floating heart, flying, glide, heart, heart eyes, holding, implied spitfire, lipstick, lockers, male, male to female, mare, moaning, name tag, one eye closed, open mouth, rule 63, sequence, sitting, solo, solo female, solo male, speech bubble, spread wings, stallion, tight clothing, transformation, transgender, transgender transformation, uniform, wingding eyes, wings, wonderbolts uniform, wrong cutie mark

Size: 2048x1318 | Tagged: safe, artist:beherelongtime, stronghoof hoofstrong (tfh), velvet (tfh), vetr (tfh), deer, reindeer, winter sprite, them's fightin' herds, clothes, community related, maid, maid stronghoof

Size: 2048x1318 | Tagged: safe, artist:beherelongtime, stronghoof hoofstrong (tfh), velvet (tfh), deer, reindeer, them's fightin' herds, clothes, community related, maid, maid stronghoof, male, text

Size: 2046x3162 | Tagged: suggestive, artist:lightisanasshole, hitch trailblazer, earth pony, pony, semi-anthro, g5, arm hooves, bedroom eyes, blushing, bowtie, bunny ears, bunny suit, clothes, crossdressing, crotch bulge, cuffs (clothes), green mane, high res, looking at you, male, playboy bunny, solo, solo male, thick, traditional art, watercolor painting

Size: 1016x719 | Tagged: suggestive, artist:excelso36, oc, oc:azure/sapphire, oc:heroic armour, oc:train track, human, equestria girls, g4, barefoot, clothes, crossdressing, dresser, equestria girls-ified, feet, femboy, makeup, male, male feet, nightgown, sissy, sissyfication, trap, underwear, wig

Size: 2953x1618 | Tagged: safe, artist:sadistjolt, angel bunny, discord, fluttershy, draconequus, pegasus, pony, g4, angel bunny is not amused, bucket, carrot, cheek kiss, cleaning, clothes, cute, demanding, female, food, fork, heart, hungry, kissing, knife, knitting, list, maid, maidcord, male, mop, ponytail, ship:discoshy, shipping, singing, sitting, straight, thought bubble, unamused

Size: 1600x1600 | Tagged: safe, artist:kathepart, big macintosh, earth pony, pony, g4, bloomers, clothes, crossdressing, dress, hoof shoes, lipstick, male, orchard blossom, simple background, solo, stallion, standing, transparent background

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

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

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