Did a lot of fumbling around trying to figure out the best angle to insert it. I was wearing a condom, but maybe need not have, because the first couple of times I didn't come at all. Coming while jerking off and coming inside with or without a condom are totally different and so I wasn't sure if I had or not. About the third time we did it. We were going and I realized that I was finally about to come and you can really tell.
Edit: her and i were friends at the time, tried dating which didnt work out. We went back to friends with benifits and remain so to this day.
Edit 2: feelings are a real thing at least in my experience. I am pretty sure i love her. I know i have felt like she has been more than an FWB for quite a while. The idea of getting her pregnant and her being the mother of my child is a total turn on. I don't know of friends who want babies together.
FYI, you can still get someone pregnant even if you don't cum. Pre-cum often contains a small amount of semen and that can definitely be enough to do the job. Not to mention the fact that STIs are a potential concern.
I wouldn't be having sex without a condom unless one or both of you has some other form of prevention, and you've both been tested since the last time you had unprotected sex, or relatively recently.
You don't want to fuck around when it comes to potentially having a kid you're not ready for, or getting an STI.