Did the second time you had anal sex hurt more than the first?

heirtothewind

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The first time I let a guy fuck me, I was too naive and stupid to realize it would hurt. Consequently, I was relaxed enough that he could push it in without much pain. It started to hurt, and hurt bad, only after he began hard and deep thrusting. But thereafter I was always clenched tight whenever I felt a cockhead against my butthole, thus causing me excruciating, searing pain upon penetration every time. And still, I always found the fear of pain to be enticing and erotic to fantasize about getting fucked even when I am getting a blowjob or fucking a tight ass.

Would like to hear from guys who have a similar experience with anal sex.