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What was your first pegging experience like?

    pegging copypasta
    My boyfriend expressed an interest in wanting to be pegged. I was very supportive but also intimidated because I don't have a lot of experience with ass play on men. But I went ahead and bought a 15 inch strap-on. It felt really strange to wear the dildo, like, awkward with this purple appendage protruding from my pelvis, pointed at my boyfriend’s poised ass. Once the dildo was inside, I checked in with him to make sure I wasn't hurting him, and he replied, 'Are you in all the way?' After I began thrusting, he said, 'I don't think this is working, it's not big enough!'”