 If you liked
Mahou Shoujo Elena
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 ...then you might like
Fate/kaleid liner Prisma☆Illya
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What if Illya was raped by tentacles? Both are semi-parody of magical girl anime, protagonist is forced to wear revealing clothes and go through embarrassment. Illya and Elena share the same flustered personality, and same kind of humor; Elena makes funny comments when she's raped instead of just saying "Oh! No! feels good!".