Hi Lovey, and welcome to the boards!
1. In general, you don’t have to enjoy vaginal entry yourself to be able to please your partner if your partner enjoys it. If you want to learn how to do it in a way your girlfriend enjoys, the best way to learn is to ask them what kind of touches they like, and let them know they can give you direction and feedback while you’re doing it. But, if you want to explore vaginal entry more, some ways to make it more enjoyable include starting slowly with one finger, using plenty of lube, and making sure you’re relaxed and aroused first. How does that sound to you?
2. You know, it’s not entirely accurate that orgasms are supposed to be super mindblowing each time, but I know that’s certainly how it can be portrayed. But, orgasms can actually feel a few different ways! To quote this wonderful article we have by our founder Heather,
Sexual Response & Orgasm: A User’s Guide,
It’s really tough to describe what an orgasm feels like. Not only does it differ from person to person, one person can experience any number of different sorts of orgasms that vary with every sexual experience, from day to day. Orgasm can feel like a tickle or a hiccup, but can also feel like a very heavy head rush or wave of dizziness through the whole body. Joani Blank once described it in a sex book for kids as feeling similar to when you really, really have to pee and then finally urinating. Overall, having an orgasm is a bit like being a balloon: your body fills up with pressure, then releases that pressure when it gets to its fullest point, much like a balloon does when it pops.
Does hearing that and reading that article give some clarity on what you’ve been feeling?