What's your biggest sexual regret?

Maybe I'll delete this later, haven't quite decided yet.

First and foremost I've been very lucky. I got around in college and had my fair share of stupid unprotected sex. Somehow I made it out clean and without children. Phew!

Fast forward a few days as I move out of my college town and leave a girl behind who somehow fell madly in love with my stupid ass. I end up in an open relationship in a big city quite far away with a good but demanding job. Fast forward again to NYE and I'm having a drunken and stupid night with my coworkers and I meet a girl. Some champagne and mackin later we end up back at my place to play hide the schnitzel. But of course I have a bit of whiskey dick with barrier protection on so I have the best idea.

Next morning I wake up and roll over with a sigh of relief, the beer gods were gentle with me. We pack up and go to have brunch with one of my coworkers (who was having a VERY rough morning). All is fine and good and I pack mystery girl in a cab and send her on her way.

Now, it's worth taking a pause to talk about love interest back home. At the end of my slutty days in school this girl and I both found ourselves in love. However, I had a job offer I was loathe to pass up for something untested so we agreed to wait for each other but to be open. We stayed in touch by Skype all the time and she was coming to visit me soon. (Also important)

January 3rd rolls around and I notice something isn't right. I've got some swelling on my frankfurter that hadn't been there before. Two days and a ton of research later: Herpes. Of course my first thought is that I got it from a stupid one night stand, I was furious with myself. I approached my local long time partner to fill her in and she went to get tested as well. We both came back positive. We were dumbfounded, despite our constant testing and use of condoms we'd both gotten tagged. In a guilty way I was sort of relieved that I'd gotten it the "responsible way" as if there is a responsible way to get herpes.

Now, finally, to my regret. The woman I love and I will never really be able to have unprotected sex again. Through my own selfish pursuit I've endangered her and potentially any children we would have as well. While I understand there's little I can do about it and she has been very supportive (despite my panic as the clock ticked down to her visit) I still feel she deserves better.

It could have been a lot worse at the end of the day I'm just trying to stay positive.

/r/AskReddit Thread