For some more context, me (m20) and my girlfriend (f19) have been dating for around 9 months now, and I’m also her first ever boyfriend. So I was her first kiss and all of that. However, I’m not a virgin lol and I miss having sex quite frankly, so within this time I’ve been trying my best to run the bases with her and we have made a lot of progress.
Though, last weekend was without a doubt the closest we ever got. I’ll give a play by play explanation… we were in my basement on the couch and we started making out, then I started moving down lower and eating her out. After I was down there for sometime I came back up and made out with her a little more then asked if she wanted to have sex. She said yes, so I asked her to stroke it while I opened these condoms. So I let her stroke it for a lil because to be honest that shit felt amazing, but then when I was bricked up hard I put the condom on and got back on top of her. I stuck the tip in and very slightly and slowly thrusted, almost immediately after she puts her hand on her face and winces. So I asked if she was ok, to which she told me it hurted.
So obviously I got off her and stopped because I felt bad. And the next thing she said was “we’ll get there” so that was good I think.
I talked to some of my friends about the situation and the only advice I’ve acquired is that I need to finger her before hand to relax her and see if she’s ready for something to go in there. I’m also wondering if any positions are preferable for losing her virginity (we obviously was trying to do missionary). Anyway, please just let me know the best way I can go about having sex with her for her first time in a way that won’t be too painful for her, and preferably is amazing for both of us.