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Doesn't sound like a big problem to me, I mean I'm not a guy so I wouldn't know for sure, but it doesn't seem that bad. If you do think that you not cumming enough durring masterbation is a big issue for yourself personally, then go to the doctor and get checked out.
As for you and your girlfriends' issue, it's all okay...yes, try lubricant to lesson the friction, or the pressure you both feel durring your sexual moments. Your penis not fitting can be due to her being a virgin(but i wouldn't know for sure), or her being just to tight, which is normal.
Don't stress, do what you think is right for yourself, be safe and have FUN!
goodluck & godbless<3
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