A gallery byNittany Discord with 6165 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.

Size: 1025x1191 | Tagged: artist needed, suggestive, snails, oc, oc:aero, human, g4, aeroshell, blushing, boop, canon x oc, clothes, condom, crossdressing, drool, gay, glitter shell, hug, humanized, kissing, male, noseboop, nudity, open mouth, panties, partial nudity, shipping, topless, underwear
Size: 1776x2859 | Tagged: safe, artist:peternators, oc, oc only, oc:heroic armour, pony, unicorn, boots, clothes, colt, crossdressing, crossplay, foal, horn, male, shoes, show accurate, simple background, skirt, smiling, sweater, teenager, the fairly oddparents, transparent background, trixie tang
Size: 2005x2505 | Tagged: safe, artist:peternators, oc, oc only, oc:heroic armour, pony, unicorn, bow, clothes, colt, crossdressing, crossplay, ear piercing, earring, foal, hair bow, horn, jewelry, male, piercing, shoes, show accurate, simple background, skirt, smiling, socks, sweater, the fairly oddparents, thigh highs, timmy turner, transparent background
Size: 1909x1567 | Tagged: safe, artist:prixy05, fluttershy, hitch trailblazer, earth pony, pegasus, pony, crystal ball (episode), g4, g5, my little pony: tell your tale, clothes swap, crossdressing, duo, duo male and female, female, g4 to g5, generation leap, hat, hitch and his 2nd heroine, male, mare, simple background, stallion, top hat, transparent background, vector
Size: 2048x1536 | Tagged: safe, artist:ry-bluepony1, oc, oc only, oc:train track, unicorn, clothes, crossdressing, dress, makeup, male, simple background, solo, transparent background
Size: 3080x1636 | Tagged: safe, artist:prixy05, fluttershy, hitch trailblazer, earth pony, pegasus, pony, g4, g5, my little pony: tell your tale, bowtie, clothes, clothes swap, crossdressing, dress, duo, duo male and female, female, g4 to g5, gala dress, generation leap, height difference, hitch and his 2nd heroine, hoof shoes, looking at someone, male, mare, open mouth, short, simple background, stallion, tall, teeth, transparent background, unshorn fetlocks, vector
Size: 6000x5000 | Tagged: safe, artist:dashingjack, oc, oc only, oc:wintergreen, earth pony, pony, blushing, clothes, crossdressing, dress, floating, garter belt, gold, panties, parachute dress, paraskirt, petticoats, solo, underwear, veil, wedding dress, wedding veil
Size: 1130x800 | Tagged: safe, artist:excelso36, oc, oc only, oc:azure/sapphire, human, equestria girls, g4, beauty and the beast, belle, blushing, clothes, crossdressing, dress, femboy, gown, gradient background, makeup, male, nervous, princess costume, princess gown, solo, wig
Size: 2200x1650 | Tagged: safe, artist:lesbottore, alicorn, earth pony, pony, 2024, alicornified, blush scribble, blushing, clothes, crossdressing, dress, duo, duo male, edgar valden, gay, gray background, grayscale, height difference, hoof shoes, horn, identity v, lidded eyes, luchino diruse, male, meme, messy mane, messy tail, monochrome, ponified, princess shoes, race swap, raised hoof, redraw, rule 85, shipping, simple background, size difference, smiling, spread wings, stallion, tail, the bride and the ugly ass groom, unshorn fetlocks, wedding dress, wedding veil, wings
Size: 3875x3175 | Tagged: safe, artist:badumsquish, derpibooru exclusive, queen chrysalis, star tracker, changeling, changeling queen, earth pony, pony, g4, against wall, alley, bipedal, bipedal leaning, blushing, brooch, clothes, cosplay, costume, crossdressing, crossplay, crown, dress, duo, eye contact, female, flirting, gloves, gown, heart, jewelry, kabedon, leaning, looking at each other, looking at someone, male, nervous, princess daisy, regalia, scared, ship:staralis, shipping, smiling, smirk, stallion, starcrossed, super mario bros., wig
Size: 1838x2060 | Tagged: source needed, useless source url, safe, alternate version, artist:kizun0shi, artist:kizunoshi, artist:osaru czan, oc, oc only, oc:sertpony, anthro, :p, bedroom eyes, belly button, blue coat, clothes, commission, crossdressing, femboy, feminine stallion, hands behind back, heart, kneeling, leaning back, male, midriff, orange mane, sfw edit, sfw version, shading, simple background, sitting, skirt, solo, stars, tongue out, white background, ych result
Size: 600x449 | Tagged: artist needed, source needed, safe, oc, oc:damiyan, pegasus, clothes, cyrillic, maid, photo, russian, text, translated in the comments, white fur
Size: 2000x3000 | Tagged: safe, artist:jedayskayvoker, oc, oc:kryostasis, changeling, anthro, bride, changeling oc, clothes, colored sketch, crossdressing, dress, fangs, femboy, flower, lipstick, looking at you, looking back, looking back at you, makeup, male, mirror, sketch, solo, veil, wedding dress
Size: 1000x1000 | Tagged: safe, artist:sotaiewe, pegasus, pony, 2023, arrow, bow, bow (weapon), clothes, crossdressing, dress, fake horn, kenny mccormick, looking at you, male, one eye closed, ponified, princess kenny, signature, simple background, solo, south park, south park: the stick of truth, wink
Size: 3840x2160 | Tagged: safe, artist:cushyhoof, oc, oc only, oc:mysti inferno, oc:precious gemstones, earth pony, pony, unicorn, ballerina, ballet slippers, ballroom, blue hair, blushing, bow, boyfriends, candle, candlelight, clothes, crossdressing, dancing, dress, femboy, gray coat, green eyes, heart, horn, male, night, orange hair, purple eyes, red hair, skirt, stallion, stars
Size: 750x1126 | Tagged: suggestive, twilight sparkle, human, equestria girls, g4, crossdressing, irl, irl human, photo