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Size: 4096x9096 | Tagged: suggestive, artist:naivintage, derpibooru import, oc, oc:smoker, oc:smokey, oc:spearmint, unofficial characters only, pony, comic:carousel idol, black underwear, blushing, bondage, butt, butt shake, carrying, cigar, cloth gag, clothes, comic, crossdressing, damsel in distress, dock, featureless crotch, fedora, fixed version, gag, gangster, gangsters, hat, kidnapped, lace underwear, lacy underwear, male, mistaken gender, muffled words, necktie, panties, panty shot, prehensile tail, rope, rope bondage, see-through, see-through panties, sissy, skirt, skirt lift, spanking, struggling, tail hold, trap, underwear, upskirt
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Size: 4096x9096 | Tagged: suggestive, alternate version, artist:naivintage, derpibooru import, oc, oc:smoker, oc:smokey, oc:spearmint, unofficial characters only, pony, absurd resolution, black underwear, blushing, bondage, butt, butt shake, carrying, cigar, cloth gag, clothes, comic, crossdressing, damsel in distress, dock, featureless crotch, fedora, gag, gangster, gangsters, hat, kidnapped, lace underwear, lacy underwear, male, mistaken gender, muffled words, necktie, panties, panty shot, prehensile tail, revision, rope, rope bondage, see-through, see-through panties, sissy, skirt, skirt lift, spanking, struggling, tail hold, trap, underwear, upskirt
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Size: 4096x9096 | Tagged: suggestive, artist:naivintage, derpibooru import, oc, oc:smoker, oc:smokey, oc:spearmint, pony, comic:carousel idol, angry horse noises, bondage, bound, bound and gagged, butt, cigar, cloth gag, clothes, comic, crossdressing, descriptive noise, fedora, gag, gangsters, hat, horse noises, kidnapped, lace, male, mistaken gender, monochrome, muffled words, panties, panty shot, redraw, sissy, sketch, skirt, spanking, struggling, torment, trap, underwear, upskirt, wip
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Size: 4096x9000 | Tagged: suggestive, artist:naivintage, derpibooru import, twilight sparkle, twilight sparkle (alicorn), oc, oc:spearmint, alicorn, earth pony, pegasus, pony, unicorn, comic:carousel idol, absurd resolution, background pony, black underwear, blushing, blushing profusely, butt, butt shake, clam, clam shell, clothes, comic, crossdressing, embarrassed, exhibitionism, female, image, lacy underwear, makeup, male, mare, offscreen character, panties, panty shot, png, see-through, see-through panties, singing, sissy, sitting, skirt, spotlight, stage, sweat, trap, trembling, underwear, upskirt
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Size: 1600x960 | Tagged: artist:naivintage, blushing, bondage, bound, bound and gagged, cigar, clothes, cloth gag, comic:carousel idol, crossdressing, derpibooru import, fedora, gag, gangsters, hat, hoof polish, kidnapped, lace, male, mascara, mistaken gender, oc, oc:spearmint, panties, panty shot, plot, questionable, rope, ropes, sissy, skirt, smoking, struggling, trap, underwear, unofficial characters only, upskirt
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Size: 895x1126 | Tagged: safe, artist:naivintage, derpibooru import, twilight sparkle, twilight sparkle (alicorn), oc, oc:spearmint, alicorn, pony, comic:carousel idol, bed, blushing, clam, covering, crossdressing, embarrassed, exclamation point, hoof polish, lipstick, male, mascara, monochrome, open mouth, sitting, surprised, tail hold, trap, wide eyes
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Size: 675x1125 | Tagged: artist:naivintage, blushing, clothes, comic:carousel idol, crossdressing, derpibooru import, embarrassed, humiliation, lingerie, male, oc, oc:spearmint, panties, sissy, solo, suggestive, trap, underwear, unofficial characters only
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Size: 675x1125 | Tagged: artist:naivintage, clothes, comic:carousel idol, crossdressing, derpibooru import, exclamation point, male, monochrome, oc, oc:spearmint, panties, rarity, safe, sissy, trap, underwear
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Size: 872x1125 | Tagged: safe, artist:naivintage, derpibooru import, twilight sparkle, oc, oc:spearmint, alicorn, earth pony, pony, comic:carousel idol, crossdressing, lipstick, male, mascara, monochrome, sissy, trap
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Size: 936x1125 | Tagged: suggestive, artist:naivintage, derpibooru import, twilight sparkle, twilight sparkle (alicorn), oc, oc:spearmint, alicorn, pony, comic:carousel idol, blushing, clothes, crossdressing, embarrassed, lipstick, male, mascara, monochrome, panties, panty shot, trap, underwear
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Filtered
Size: 643x477 | Tagged: artist:naivintage, blushing, clothes, comic:carousel idol, crossdressing, derpibooru import, dock, hoof polish, lipstick, male, mascara, monochrome, oc, oc:spearmint, panties, panty shot, plot, presenting, questionable, skirt, solo, solo male, teasing, the ass was fat, underwear, unofficial characters only, upskirt
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Size: 658x1125 | Tagged: safe, artist:naivintage, derpibooru import, rarity, twilight sparkle, twilight sparkle (alicorn), oc, oc:spearmint, alicorn, pony, unicorn, comic:carousel idol, blushing, male, mascara, monochrome, sissy, trap
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Size: 812x983 | Tagged: artist:naivintage, blushing, clothes, comic:carousel idol, crossdressing, derpibooru import, embarrassed, femdom, hoof polish, humiliation, lineart, lipstick, male, mascara, microphone, monochrome, oc, oc:spearmint, offscreen character, panties, panty shot, rarity, scared, sissy, skirt, stage, stuttering, suggestive, trap, underwear, upskirt
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Size: 1500x900 | Tagged: artist:naivintage, bondage, clothes, comic:carousel idol, crossdressing, derpibooru import, femdom, forced feminization, hoof polish, lingerie, makeover, male, oc, oc:spearmint, panties, panty shot, rarity, sissy, sissyfication, stool, suggestive, tickling, trap, underwear
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Size: 1100x1125 | Tagged: artist:naivintage, blushing, comic:carousel idol, crossdressing, derpibooru import, lipstick, male, mascara, oc, oc:spearmint, rarity, shivering, sissy, suggestive, trap, trembling
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