I'm sorry you're dealing with this, and that you feel so badly about it.
A new infection can be somewhat unpredictable, but I also wonder if you have a secondary infection. You don't mention your sex, so some of this may not apply to you, but secondary infections can be things like yeast, bacterial vaginosis, a fungal infection, another STD, etc.
1. Can I have an outbreak on both sides?
Yes, though it's more common to get them on one side. Herpes infects nerve groups, and genital herpes infects the sacral ganglia. This means that you can get outbreaks anywhere that boxer shorts cover.
2. Can I get one outbreak right after another? Or is it something else?
Yes, and yes. When I first got herpes, I got back to back outbreaks for 9 months. It was as miserable as it sounds, and I was taking valtrex, which was seemingly doing nothing. Finally, after the urging of a friend, I went to the doctor and found out I had bacterial vaginosis. Once I got that taken care of, my herpes settled down. It's really common to get a secondary infection when you are newly infected with herpes.
3. If I have outbreaks like this, does it mean I will have often outbreaks?
Maybe, or not. (I know that's a sucky answer.) It's hard to say what is going to happen without knowing if you have a secondary infection. A new infection can be fairly unpredictable, and then calm down, but you may be have a secondary infection.
4. Is there something i can do to make the outbreaks go away faster?
Are you on antivirals, like Valtrex, acyclovir or famvir? Taking these at the first sign of an outbreak can make them go away faster, and once you learn your prodrome (your warning sign that an outbreak is coming - this can be anything from tingling in a certain spot, pain in your thighs, etc - it's unique to you), you can take it then and perhaps prevent the outbreak.
You might also want to try them suppressively as your body calms down. This means taking them daily.
I'm very sorry to hear that this has hurt your sexual confidence and that you may not have sex again. Please reconsider that.
Ghsv1 rarely sheds (about 3-5% of days per year), and rarely transmits to anyone else. If your partner already has hsv1, you can't give it to them, as they can't get something they already have. (They'll have antibodies that prevent them from being reinfected.) About half the population has hsv1. Please don't write off what can be a beautiful part of your life. Gazillions of people have herpes, and have "normal" sex lives - or normal for them, because normal is relative - and have healthy relationships, get married, have kids, have awesome sex, etc.
So too long, don't read - you could have a secondary infection, so see your doctor. You can have an awesome life with herpes. I've had hsv2 for 15+ years, and it's really just a small blip now. So, so many other things have impacted my life way more than herpes ever has.