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Images tagged crossdressing

Size: 514x700 | Tagged: artist:mewball, clothes, crossdressing, male, oc, oc:candy prancer, safe, school uniform, solo, trap
Size: 2008x3912 | Tagged: alternate version, artist:paskanaakka, blushing, claws, clothes, crossdressing, derpibooru exclusive, dragon, evening gloves, gloves, lingerie, long gloves, male, older, older spike, simple background, solo, solo male, spike, stockings, suggestive, thigh highs, transparent background, winged spike
Size: 10807x8125 | Tagged: artist:digimonlover101, crossdressing, equestria girls, femboy, feminization, makeover, male, oc, oc:azure/sapphire, oc:gareth, safe
Size: 960x1280 | Tagged: anime, anthro, artist:dashingjack, bowtie, chef's hat, clothes, crossdressing, femboy, hat, magical girl outfit, male, mittens, oc, oc:northern haste, rat, safe, socks, unguligrade anthro, wig
Size: 1280x1280 | Tagged: anthro, artist:kryptchild, bow, choker, clothes, crossdressing, cute, dress, glitter shell, happy, male, mary janes, safe, simple background, snails, solo, stockings, thigh highs, transparent background, unicorn
Size: 11000x6000 | Tagged: artist:evilfrenzy, cookie, crossdressing, cute, derpy hooves, filly scouts, food, oc, oc:liatris blossomheart, oc:petticoat, oc:precious kitten, safe
Size: 3753x2482 | Tagged: 1000 hours in ms paint, abby's flying fairy school, crossdressing, crossover, fairy, flutterlori loud, fluttershy, gonnigan, gonnileni loud, leni loud's outfit, lori loud's outfit, pegasus, ponies wearing clothing, pony, safe
Size: 2531x1774 | Tagged: artist:nstone53, bisexual pride flag, crossdressing, equestria girls, femboy, genderfluid pride flag, high heels, kissing, lipstick, makeup, male, oc, oc:azure/sapphire, oc:cold front, oc:disty, pansexual pride flag, petticoat, pride month, safe, shoes, swing dress, transgender pride flag
Size: 1768x1691 | Tagged: artist:superdavid2011, clothes, crossdressing, maid, male, oc, oc:cold front, pegasus, pony, safe, solo, stallion, traditional art
Size: 1000x1200 | Tagged: artist:sixes&sevens, clothes, crossdressing, dress, ear piercing, earring, freckles, glitter shell, hoof polish, jewelry, piercing, pony, safe, simple background, snails, tongue out, transparent background, unicorn
Size: 1600x1600 | Tagged: anthro, artist:vinned, bag, briefcase, clothes, crossdressing, oc, oc:lucky, pleated skirt, safe, schoolgirl, school uniform, short shirt, skirt, socks, thigh highs, thighs, zettai ryouiki
Size: 400x652 | Tagged: 2b, anthro, artist:midday sun, boots, clothes, cosplay, costume, crossdressing, crossplay, crotch bulge, dress, dress lift, earth pony, knee-high boots, male, nier: automata, oc, oc:midday sun, panties, panty shot, shoes, skirt, skirt lift, stallion, stockings, suggestive, thigh highs, underwear, upskirt, white underwear
Size: 1000x608 | Tagged: 1000 hours in ms paint, abstract background, afro, anthro, best friends, clothes, clown hair, clown nose, clown pony, crossdressing, crossover, dress, earth pony, five nights at freddy's, fox, foxy, foxy vera, gloves, pony, ponytail, princess crown, princess dress, princess foxy vera lola, prototype lola loud's outfit, safe, sash, sonicified, sonic the hedgehog (series), spa pony, text, vera, vera the clown pony, waving
Showing images 1 - 15 of 3491 total