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How is sex for you? How is your sensation? Another idea that just popped up: what if you initiate sex, with him jerking himself off first and then proceed with sleeping together? Would that help maybe?
You can always go through your university counseling that they offer for free if you don’t feel comfortable telling your dad.
My husband slapped me hard and then grabbed my jaw back towards his face to kiss me very hard and messy. I like it rough and he’s a really gentle guy so it’s been a challenge getting him to a place where he feels comfortable doing this. It was really hot and I’ve been playing it back in my head the last few weeks
It definitely shouldn’t hurt so much that you are not able to put your whole finger in. Vaginismus sounds like probable issue. Find a better specialist and good luck!