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Can you pop your cherry and have it not bleed?

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I had sex about 2 times with my boyfriend and before that, he use to finger me with like 1-3 fingers. I thought he popped my cherry and im pretty sure he did cause having sex doesn't hurt and him fingering me doesnt. Buut he isnt that large.. and if I didnt pop my cherry why doesnt it hurt? and why havnt I bled? im 14... adviiccce?