I haven't had many partners, I'm 20M and she's 23F, we are super into each other and dating for 3 months, but have seen each other 2 times (for 2 days each), and one thing I noticed is that we are so awkward making penetration work, its making me anxious.
Our first time, we could only start actual sex after 5 straight minutes with me inside her staying still, because she is super tight and needs to get dilated (this is after blowjobs, tons of flirtations and foreplay), and on my pov, this is extremely hard because I start getting anxious this won't work, I'm slightly out of shape + average-small dick and this just makes me think its also my fault, and it also snowballs into me getting kind of a half erection which ABSOLUTELY doesn't work with her being SUPER-Tight (have never seen anything close to this).
So we have been texting for months now about doing all crazy stuff, outdoor sex, crazy acts, and all that, but like, every time we actually try, we are in it for 30 minutes TRYING TO make penetration work!!! In like 15 tries I only got an actual good penetration 2 times. The others I'm only half-hard and also my dick keeps slipping out of her (which also destroys me a bit when it happens)
We are both understanding to each other and laugh it off, but I'm worried we are not physically compatible atleast not at the moment? (With her being super tight and me being on the smaller side with not the strongest erections)
We are not really lacking in foreplay/desire either, its just the awkward penetration, and she REALLY likes good penetration.