Penile Insertion Hurts for Some Reason?

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I decided to use my dildo again for the first time in years last night. This dildo has some weird ribs on it, it’s not shaped like a regular penis. And once again it hurt? I have avoided using this one for years because it hurts. But I don’t think it’s supposed to hurt. This time I used a condom on it and I always use lube. And this time I warmed up with my vibrator before using it and while using it and insertion still hurt. And I noticed that when I had sex with a man for the first time this year it hurt too. I don’t know what I’m doing wrong. Why is it hurting? I thought maybe the sex with the guy hurt because he did no foreplay. But I’m wondering if I just can’t take it? It just wasn’t pleasureable at all to have that dildo inside me. I mean mildly, but for the most part, not at all. I have another dildo but that is a dilating dildo and it isn’t shaped like a penis at all and it’s much skinnier and smaller/thinner than the other dildo I have. That one has given me some orgasms before but I don’t always cum from it. It’s about 5.5” long I believe. But whenever I think about sex, I like the idea of someone penetrating me. So I don’t know if I just can’t handle dick or I am doing something wrong. Please help.

PS., if it helps to know, I might have endometriosis.

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