I just got out of a 1 year relationship and I was using condoms the whole time. The sex was good but nowhere near as good as prior relationships (without condoms). I have to problems with condoms. 1. They make my dick softer if I don't put it on and immediately enter a girl. 2. They dry up the girl big time. When I have sex without a condom girls have no issue getting and staying wet. When I wear a condom, it feels like it's drying my dick out and definitely drying the girl out. This leads to uncomfortable at best and painful at worst sex.

Went out this Saturday and met up with a female friend who I barely know but am friendly with. We were both pretty drunk made out and went back to my place. Got naked on my bed, and even though she was on her period I was determined to fuck her. I put a condom on and entered her and she immediately stopped me because it was giving her pain. Frustrated, I took it off and didn't know what to do. I asked her if she wanted to do anal, but she claimed she never did it before. After 15 seconds of convincing, she agreed (bullshit it was her first time). I put some lube on my dick and entered her butt, but that was painful for her too.

My horniness got the best of me and she said I can fuck her without a condom because she's on birth control. I entered her vagina and the sex was amazing and she was wet. I pulled out and came on her back, but she asked me why I did that and said I could have came in her vagina because she was on the pill (red flags I know).

Now I'm paranoid I have an STD because this girl seemed like a big slut.

Any condom tips? My dick is 6" length and on the girthier side. Should I put some lube inside the condom and then rub some on the outside once it's on? I usually need to put a condom on quickly and enter immediately to stay hard. I'm using durex ultra thin condoms, as they were better than some of the other ones that I tried. Any tips for me?

TL;DR I had unprotected sex because I am not having a good experience with condoms. Need advice on proper size and use.