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Viewing gallery Nittany's Crossdressing Extravaganza
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A gallery byNittany Discord with 6207 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.

20203
Size: 750x1126 | Tagged: suggestive, twilight sparkle, human, equestria girls, g4, crossdressing, irl, irl human, photo
597511
Size: 469x670 | Tagged: safe, artist:kreeeeeez, spike, g4, blushing, clothes, crossdressing, doodle, dress, laughing, lolita fashion, simple background, solo, white background
40570
Size: 1761x2093 | Tagged: safe, artist:naivintage, oc, oc only, oc:spearmint, earth pony, pony, blushing, boots, breeching, butt, clothes, cosplay, costume, crossdressing, dc comics, earth pony oc, harness, looking back, male, plot, shoes, simple background, solo, stallion, superhero, tack, white background, wonder woman
13176
Size: 1280x768 | Tagged: suggestive, artist:taboopony, edit, oc, oc:leostar, earth pony, blushing, butt, clothes, crossdressing, earth pony oc, face down ass up, muscles, panties, plot, underwear, zebra hybrid
324311
Size: 433x676 | Tagged: safe, artist:howie, oc, oc:revol sparks, earth pony, human, anthro, adult blank flank, ass, blank flank, brown eyes, brown fur, brown mane, brown tail, butt, clothes, crossdressing, femboy, glasses, humanized, implied tail hole, male, ocean, one-piece swimsuit, solo, stallion, swimsuit, tail, water
40611
Size: 2048x2048 | Tagged: safe, artist:shallowwin, oc, oc:benjamin terrance tover, earth pony, anthro, ace attorney, clothes, cosplay, costume, courtroom, crossdressing, franziska von karma, glasses, phoenix wright, whip
59884
Size: 1304x1976 | Tagged: suggestive, artist:moonatik, oc, oc only, oc:baron, oc:moonatik, pegasus, unicorn, anthro, anthro oc, bondage, bound legs, bound wings, bowtie, bridal carry, butt, carrying, clothes, crossdressing, cuffs, emanata, face mask, female, femboy, femdom, glasses, gloves, hand, handcuffed, horn, maid, male, malesub, mare, mask, necktie, panties, pegasus oc, police officer, ponytail, shoes, size difference, stallion, straight, submissive, suspenders, underwear, unicorn oc, wings
1091457
Size: 3239x4132 | Tagged: suggestive, artist:daisy_marshmallow, comet (g5), violet frost, auroricorn, anthro, unguligrade anthro, g5, bbw, blushing, breasts, bunny suit, chubby, clothes, crossdressing, duo, duo male and female, fat, female, femboy, fishnet stockings, glasses, heart hands, looking at you, male, shy
28400
Size: 2048x2048 | Tagged: safe, artist:regularcitrus, pegasus, pony, unicorn, mlp x jojo, alternate name, alternate universe, anime, battle tendency, caesar zeppeli, crossdressing, crossover, jojo's bizarre adventure, joseph joestar, long description, ponified, simple background, tequila joseph, white background, wing hands, wings
46620
Size: 1009x1692 | Tagged: safe, artist:askadospike, spike, dragon, g4, belt, champagne glass, clothes, crossdressing, cute, dress, evening gloves, eyes closed, femboy spike, gloves, long gloves, male, monochrome, older, older spike, purple background, simple background, smiling, solo, spikabetes, stockings, stupid sexy spike, teenage spike, teenaged dragon, teenager, thigh highs, tray
14161
Size: 2036x1551 | Tagged: suggestive, artist:midday sun, octavia melody, rarity, human, g4, bowtie, bra, clothes, corset, elusive, evening gloves, femboy, garter belt, garters, gloves, humanized, leotard, lingerie, long gloves, makeup, male, octavius, panties, rule 63, stockings, sultry pose, thigh highs, traditional art, underwear
284510
Size: 2500x2500 | Tagged: safe, artist:fuzzystarart, oc, oc:shadow twinkle, bat pony, bow, clothes, commission, crossdressing, cute, dislikes, femboy, floating heart, glasses, hair bow, heart, heterochromia, likes, male, reference sheet, skirt, small stallion, socks, stallion, sweater, thigh highs
49671
Size: 1000x1415 | Tagged: suggestive, artist:hiddendesire, oc, oc only, oc:ryo(j), unicorn, anthro, unguligrade anthro, blushing, bunny ears, bunny suit, clothes, crossdressing, crotch bulge, gloves, horn, horn ring, latex, latex suit, leotard, magic suppression, male, pantyhose, ring, solo, solo male
27520
Size: 3840x2160 | Tagged: safe, alternate character, alternate version, artist:shadowuwu, oc, oc only, oc:flame quill, oc:sound shock, alien, alien pony, pegasus, anthro, g4, 3d, 4k, afternoon, anthro oc, arm behind back, black sclera, branches, button-up shirt, clothes, cloud, crossdressing, dress, dress shirt, duo, femboy, flower, flower in hair, gay, hand on cheek, high res, horn, leaves, looking at each other, looking at someone, male, married couple, nail polish, oc x oc, rose, shipping, shirt, smiling, smiling at each other, source filmmaker, spread wings, sun, swing, swing set, tree, unicorn horn, vest, wedding dress, wings
55801
Size: 1221x1772 | Tagged: safe, artist:ladysdino, princess celestia, oc, oc:dreamy daze, alicorn, pegasus, anthro, plantigrade anthro, g4, bowser, cake, cakelestia, canon x oc, chase, clothes, costume, crossdressing, crossover, crossplay, dreamlestia, female, food, male, princess peach, shipping, straight, super mario bros.
63942
Size: 5600x10165 | Tagged: source needed, safe, artist:suchalmy, oc, oc:stryker, pegasus, anthro, absurd resolution, arm behind head, clothes, crossdressing, femboy, leg warmers, looking at you, male, skirt, solo
10170
Size: 184x228 | Tagged: safe, oc, oc only, oc:sugarcube, pony, sheep, pony town, animated, crossdressing, femboy, gif, horns, male, pixel art, simple background, solo, transparent background, trotting
Showing results 61 - 75 of 4043 total