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: 620x808 | Tagged: suggestive, artist:tair, prince blueblood, snails, anthro, plantigrade anthro, g4, barefoot, clothes, comic, crossdressing, dress, duo, duo male, feet, foalcon, foot fetish, foot worship, gala, gay, licking foot, male, trap, tuxedo

Size: 2421x3188 | Tagged: suggestive, artist:bronybutt, oc, oc only, oc:sweet cheeks, pony, unicorn, both cutie marks, clothes, crossdressing, crotch bulge, horn, lingerie, male, male oc, mooseknuckle, panties, pony oc, presenting, socks, solo, solo male, stallion oc, stockings, taint, thigh highs, trap, underwear, unicorn oc

Size: 800x1020 | Tagged: safe, artist:klondike, spike, g4, crossdressing, grayscale, monochrome, simple background, solo, white background

Size: 900x695 | Tagged: safe, artist:fen-fen, crossdressing, drag queen, makeup, male, ponified, ru paul, rupony, trap, vulgar

Size: 1000x1000 | Tagged: dead source, safe, artist:kryptchild, doctor whooves, time turner, g4, clothes, crossdressing, dress, earring, eyeshadow, hourglass, makeup, male, shoes, tardis, trap

Size: 853x1280 | Tagged: safe, artist:artagonist, big macintosh, earth pony, pony, g4, clothes, crossdressing, maid, maid big macintosh, male, solo, stallion

Size: 792x612 | Tagged: safe, artist:scribble, discord, g4, 30 minute art challenge, bunny suit, clothes, crossdressing, femboy discord, fishnet stockings, leotard

Size: 600x1000 | Tagged: safe, artist:ask-the-flightless-hunter, discord, g4, 30 minute art challenge, clothes, crossdressing, dress, femboy discord

Size: 1280x800 | Tagged: safe, artist:thunderthief, discord, g4, 30 minute art challenge, crossdressing

Size: 829x900 | Tagged: suggestive, artist:tt-n, discord, g4, 30 minute art challenge, cigarette, cigarette holder, clothes, crossdressing, femboy discord, fishnet stockings, implied prostitution, lineart, panties, purse, smoking, underwear

Size: 1280x1737 | Tagged: safe, artist:glasmond, discord, pinkie pie, ask human pinkie pie, g4, bowtie, crossdressing, femboy discord, flapper, garçonne, high heels, humanized, skinny, thin

Size: 1280x1079 | Tagged: safe, artist:miss-zi-zi, spike, dragon, g4, blushing, clothes, crossdressing, duster, lusty baby dragon maid, maid, male, solo, traditional art

Size: 1280x1656 | Tagged: suggestive, artist:hasana-chan, braeburn, earth pony, semi-anthro, g4, bedroom eyes, burlesque, clothes, corset, crossdressing, dress, evening gloves, feather, floppy ears, garter, gloves, jewelry, male, necklace, smiling, solo, solo male, stockings

Size: 843x947 | Tagged: safe, discord, g4, clothes, crossdressing, dress, femboy discord, hat, umbrella

Size: 550x668 | Tagged: safe, artist:mr-tiaa, oc, oc only, oc:banana scent, oc:jingle blue, banana, chubby, clothes, crossdressing, fat, maid, tumblr

Size: 708x714 | Tagged: safe, artist:kiana, oc, oc only, human, pony, unicorn, blushing, clothes, crossdressing, eared humanization, horn, horned humanization, humanized, maid, male, mary janes, solo

Size: 563x735 | Tagged: safe, artist:kilo, king sombra, g4, crossdressing, drag, sketch