Can't cum inside of something, it hurts

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25M here. When I was young (about 16) I've had foreskin surgery for my phimosis (not to be confused with circumcision). After that I was able to pull my foreskin back and forth. For years my glans was so sensitive that it could not even be touched because that pain was unbearable.

It's only since a few years that I'm actually able to touch my glans and penetrate women or sex toys. Thrusting does not hurt, but for some reason cumming hurts A LOT. Whenever the orgasm starts and I start to tighten my "cum muscles", rubbing the glans becomes painful and all I can do is stop moving and let it out (which is also painful).

Cumming on its own is not painful but for reason cumming inside of something, while the glans is squeezed by something is painful and impossible.

What could this be and what can I do? I'm missing out on the best part of sex...

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