My first blowjob, suggested by my girlfriend without me asking (I was 17, lacking all experience, and convinced if I waited long enough, someone would offer me sex... and then it happened, so... that's pretty weird; she was 15, basically asexual but neither of us knew that term back then). But she would only do it with a flavored condom. The flavor wore off after a few minutes, so she stopped and said she'd finish me with a handjob. She got me close, freaked out about touching a penis, and I had my first ruined orgasm.

My second blowjob was my second long-term girlfriend. We had been making out a lot, and doing lots of hand stuff, so I asked her for a blowjob. She hesitated, then went to town. I finished, she swallowed, I go to kiss her and do some cuddling and she starts crying and says, "I didn't want to do that." I asked for the blowjob, so that makes me responsible, but what I didn't know was that her previous relationship was abusive, so she would do things like that to avoid setting him off. She knew I wasn't like that, but still went right into "freeze" mode when I asked her, and her "freeze" mode was enthusiastic compliance. I'm still not a big fan of blowjobs to this day.