Philomena open beta / breaking API changes New software powering Derpibooru. Read more
The 2020 Community Collab has begun! Join in for round four of our massive group collaboration image! Click here for more information.

Images tagged crossdressing

Size: 3120x3400 | Tagged: arabic, artist:goldenfoxda, belly dancer, belly dancer outfit, bra, bra on pony, clothes, crossdressing, ear piercing, earring, eyeshadow, flats, harem, harem outfit, harem pants, jewelry, makeup, male, necklace, oc, oc:goldenfox, piercing, pony, ponytail, saddle arabia, shackles, shoes, slippers, solo, solo male, stallion, suggestive, underwear, veil, vest
Size: 750x750 | Tagged: artist:lumineko, bed, clothes, colt, crossdressing, cuddling, laying on bed, laying on top of someone, male, oc, oc:heroic armour, pegasus, pony, rumble, safe, shoes, skirt, smiling, snuggling, socks, sweater, unicorn
Size: 4400x3440 | Tagged: artist:goldenfoxda, belly dancer, bra, bra on pony, clothes, crossdressing, flats, harem, harem outfit, headdress, male, oc, oc:goldenfox, panties, pillow, pony, slippers, stallion, suggestive, underwear, veil, vest
Size: 1233x1667 | Tagged: anthro, anthro oc, artist:blackblood-queen, body scars, clothes, crossdressing, digital art, femboy, male, oc, oc:daniel dasher, safe, scar, scaring, solo, stallion, unguligrade anthro, unisex, unisex clothes
Size: 631x654 | Tagged: 4chan, alternate version, artist:anonymous, clothes, colored, crossdressing, drawthread, dress, erection, i have the weirdest boner, implied erection, male, meme, /mlp/, oc, oc:anon, pegasus, penis, ponified, ponified meme, pony, skirt boner, solo, suggestive
Size: 2903x1574 | Tagged: alicorn, apple bloom, applejack, clothes, cosplay, costume, cozy glow, crossdressing, dab, derpy hooves, discord, dj pon-3, draconequus, dress, eris, fluttershy, gala dress, grogar, halloween, holiday, jack-o-lantern, joke, leaves, maid, nurse, octavia melody, picnic blanket, pinkie pie, police, pond, pony, pony town, princess cadance, princess celestia, princess luna, pumpkin, queen chrysalis, rainbow dash, rarity, rule 63, safe, sapling, scootaloo, shining armor, sign, spectre, starlight glimmer, statue, sunset shimmer, sweetie belle, tree, tree stump, trixie, twilight sparkle, twilight sparkle (alicorn), vinyl scratch, xibalba
Size: 1600x1700 | Tagged: antlers, artist:dragonfrootii, clothes, collar, costume, crossdressing, femboy, male, oc, oc:kistile glow, pegasus, reindeer antlers, safe, skeleton costume, skirt, socks, solo
Size: 3024x4032 | Tagged: clothes, crossdressing, human, irl, irl human, panties, photo, pinkie pie, pink underwear, plushie, socks, suggestive, underwear
Size: 3100x10200 | Tagged: advice, alternate hairstyle, artist:kryptchild, ask glitter shell, bap, blushing, bracelet, clipboard, clothes, comic, comic:when aero met glitter, crossdressing, cute, dress, excited, frown, glitter shell, glowing horn, heart, high res, hooves on cheeks, horn, hug, jewelry, levitation, magic, pony, rarity, safe, sigh, snails, speech bubble, telekinesis, unicorn
Size: 1668x2005 | Tagged: arch, artist:lightningbolt, bags under eyes, blushing, bone, book, bowtie, bring me the horizon, brothers, clothes, colored blushing, colored pupils, colored sclera, crossdressing, derpibooru exclusive, diamond, dream sequence, dress, earth pony, fangs, floppy ears, flower, flying, gay, glasgow smile, hedge, holding hooves, hoof hold, hoof on hip, incest, lace, lidded eyes, long sleeves, looking down, male, marriage, oliver sykes, outdoors, pegasus, pierce the veil, ponified, pony, ponytail, raised hoof, safe, shipping, shirt, shocked, siblings, stallion, standing, story included, suit, surprised, svg, .svg available, tattoo, tom sykes, undead, undershirt, vector, vic fuentes, wedding, wedding arch, wedding dress, zombie, zombie pony
Size: 1280x2897 | Tagged: angry, anthro, antlers, argument, artist:whisperfoot, belly fluff, blushing, cheerleader, cheerleader outfit, chest fluff, clothes, comic, crossdressing, deer, deerified, dialogue, ear fluff, feather, french kiss, gay, gritted teeth, kissing, male, midriff, mlem, oc, oc only, oc:weldbead, patreon, patreon reward, pegasus, pleated skirt, pointing, pointing at self, self ponidox, short tail, shoulder fluff, silly, simple background, skirt, socks, sports bra, squint, striped socks, suggestive, thigh highs, thigh high socks, tongue out, tongue tied, unguligrade anthro, wat, watermark, yelling
Size: 1400x1800 | Tagged: anime, artist:twilite-sparkleplz, bow, broom, clothes, commission, cosplay, costume, crossdressing, equestria girls, femboy, flash sentry, glitter shell, hair bow, halloween, holiday, jack-o-lantern, kiki's delivery service, male, oc, oc:felicity sentry, pumpkin, purse, safe, snails, witch
Showing images 1 - 15 of 3777 total

Search