Prior to getting married there is no dam way I would risk going bare.
That was me 100% when I was younger. I was deathly afraid of getting g a girl knocked up. I had too many friends that ended up in that situation.
I think I was 22 when I finally fucked and unloaded into a woman. She was older and happily married, I was her side peice. She guaranteed me she wouldn't get pregnant, she was 41 and on the pill for years. She'd visit almost every Thursday after work, we'd fuck 3 times then she'd go home and have sex with hubby. No rubbers ever.
Different gal, happily married and pregnant by her hubby. She was HORNY, stopped by my place at least 3 times a week. No rubbers.
Different girl, I was 23 she was almost 20. Engaged, from a good wholesome, well respected church family. She was on the pill so she could have sex with her fiancee, her parents didn't know. Her fiancee was 26. I fucked her many many times, she was very attractive, classy and absolutely loved sex. Didn't use condoms with her. She got me into going down on her after we'd have set. She'd cum HARD then wanted more sex.
Other than those girls I used a rubber every time.