Derpibooru
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Viewing gallery Transgenders & Tomboys in Dresses
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A gallery byPonyLife_20 with 47 images, last updated
Size: 3619x2318 | Tagged: safe, artist:liaaqila, oc, oc:azure/sapphire, equestria girls, g4, clothes, crossdressing, dress, equestria girls-ified, femboy, gown, high res, male, princess costume, traditional art

Boys and tomboy girls who enjoy being feminine and love to dress up in beautiful dresses

26331
Size: 1886x807 | Tagged: safe, alternate version, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, human, equestria girls, g4, cancan dancer, clothes, crossdressing, dancing, dress, femboy, high heels, looking at you, makeup, male, shoes, smiling, smiling at you, stockings, store, thigh highs, trio, wig
32402
Size: 1493x1056 | Tagged: safe, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, human, equestria girls, g4, clothes, crossdressing, dancing, dress, femboy, girly, girly girl, gown, looking at you, makeup, male, smiling, smiling at you, store, trio, wig
37413
Size: 661x935 | Tagged: safe, alternate version, artist:excelso36, oc, oc only, oc:azure/sapphire, oc:petticoat, oc:zaria deibele, equestria girls, g4, bisexual pride flag, bow, clothes, crossdressing, demigirl pride flag, dress, equestria girls-ified, femboy, gay pride, gay pride flag, genderfluid pride flag, high heels, male, pansexual pride flag, park, pride, pride dress, pride flag, shoes, traditional art
38463
Size: 1558x2780 | Tagged: safe, artist:hayley566, oc, oc only, oc:azure/sapphire, equestria girls, g4, clothes, crossdressing, femboy, genderfluid pride flag, headband, high heels, male, pansexual pride flag, pride, pride dress, pride flag, pride month, shoes, simple background, solo, stockings, thigh highs, transparent background, wig
37461
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, petticoat, poofy dress, princess costume, princess gown, solo, wig
47776
Size: 2042x2043 | Tagged: safe, artist:liaaqila, derpibooru exclusive, oc, oc only, oc:mysti inferno, oc:precious gemstones, human, equestria girls, g4, blue hair, clothes, crossdressing, dress, femboy, high heels, high res, makeup, male, mirror, red hair, shoes, simple background, table, traditional art, vanity, white background
11617710
Size: 2719x2866 | Tagged: safe, artist:dandy, oc, oc only, oc:cold front, pegasus, anthro, unguligrade anthro, blushing, bow, clothes, commission, crossdressing, dress, ear fluff, femboy, high res, lolita fashion, looking at you, male, pegasus oc, shoes, simple background, sitting, socks, solo, white background, wings
60826
Size: 2181x2180 | Tagged: safe, artist:liaaqila, oc, oc only, oc:bsod, oc:cold front, oc:disty, equestria girls, g4, bow, clothes, commission, crossdressing, dress, dressing, equestria girls-ified, evening dress, femboy, high heels, high res, makeover, male, shoes, smiling, traditional art
40460
Size: 2048x1152 | Tagged: safe, artist:lavender-doodles, oc, oc:azure/sapphire, human, equestria girls, g4, beauty and the beast, belle, clothes, costume, crossdressing, dress, fake breasts, femboy, gloves, gown, high heels, makeup, male, petticoat, princess costume, sexy belle, shoes, simple background, stockings, sultry pose, thigh highs, thigh socks, white background
63786
Size: 890x1125 | Tagged: safe, artist:riouku, oc, oc:azure/sapphire, human, equestria girls, g4, 50's fashion, crossdressing, femboy, genderfluid pride flag, high heels, lipstick, makeup, male, pansexual pride flag, pride, pride dress, pride flag, shoes
7610913
Size: 2640x2986 | Tagged: safe, artist:liaaqila, oc, oc only, oc:azure/sapphire, oc:cold front, oc:disty, human, equestria girls, g4, beauty and the beast, belle, cinderella, clothes, crossdressing, dress, eye clipping through hair, eyebrows, eyebrows visible through hair, eyes closed, femboy, feminization, gown, grin, high res, jewelry, makeover, male, mouth hold, petticoat, plushie, princess costume, ring, simple background, sleeping beauty, smiling, traditional art, white background
54637
Size: 1600x2525 | Tagged: safe, artist:nstone53, oc, oc:azure/sapphire, equestria girls, g4, 50's fashion, crossdressing, drag queen, femboy, genderfluid pride flag, high heels, male, pansexual pride flag, petticoat, pride, pride dress, pride month, shoes
59757
Size: 4000x3090 | Tagged: safe, artist:dieart77, oc, oc:azure/sapphire, equestria girls, g4, crossdressing, femboy, genderfluid pride flag, makeup, male, pansexual pride flag, pride, pride dress, pride flag, pride month
47717
Size: 2702x3601 | Tagged: safe, artist:liaaqila, oc, oc only, oc:azure/sapphire, oc:petticoat, oc:zaria deibele, equestria girls, g4, asexual pride flag, bisexual pride flag, crossdressing, demigirl pride flag, drag princess, female, femboy, genderfluid pride flag, high res, male, pansexual pride flag, pride, pride dress, pride flag, pride month, traditional art
13616843
Size: 4134x2718 | Tagged: safe, artist:art-2u, oc, oc:azure/sapphire, oc:cold front, oc:disty, human, equestria girls, g4, clothes, crossdressing, digimon, dress, evening gloves, femboy, feminization, gloves, gown, long gloves, makeover, male, mario bros., princess, princess costume, princess melody, princess mimi, princess peach, puffy sleeves, super mario, the little mermaid, the little mermaid 2: return to the sea
62715
Size: 2531x1774 | Tagged: safe, artist:nstone53, oc, oc:azure/sapphire, oc:cold front, oc:disty, equestria girls, g4, bisexual pride flag, crossdressing, femboy, genderfluid pride flag, high heels, kissing, lipstick, makeup, male, pansexual pride flag, petticoat, pride, pride dress, pride month, shoes, swing dress, transgender pride flag
Showing results 1 - 15 of 47 total