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Boyfriends penis too big? Okay so I have a problem here. My boyfriend and I are ready to have sex, but his penis is way too big. He is literally inches long. I am afraid that if we end up having sex that it will hurt and that it will stretch me out. If we end up breaking up some day, no guy will be able to satisfy me. When I was in my early 20's I had a boyfriend who was too big, too long and too much girth. Lube was no help at all. He had to learn not to penetrate me fully - having my cervix banged on a regular basis was a huge turnoff as it can be very painful.