I am 41 and I cheated on my wife two times. The first time, the girl got pregnant and I told my wife about it. The second time was 2009, but this time, I treated my wife badly. It only lasted for 5 months and I appologised to my wife. I realized that it is not worth it and I begged her for forgiveness.
What bothers me though is that during the same time in 2009, my wife hooked up with her high school boyfriend and something went down. She continues to call and text him and he continues to tell her how much he is still in love with her.
What should I do. I cry almost every day.

What do you expect, everything to go back to normal after two affairs, and one where you got a woman pregnant. I don't doubt she went off the deep end and decides if you can do, she can too, and I don't blame her, so deal with it. You started the whole horrible mess, so deal with it. You don't appear to be a very strong peson, so maybe you should just step up to the plate and get on with your life in a reasonable manner with your wife. Maybe the two of you can find happiness again being honest with each other.
Tick

You make it sound like telling her makes it OK.
You make it sound like apologizing makes it OK.
You make it sound like 'only' 5 months is 'only' a short time.
You make it sound like treating her badly is OK as long as you admit it.
Cry away. THINK about how much she cried, just like you are crying now.
Think about HER, not yourself.
Maybe after a while of seeing you cry as much as she did, she will be able to work out a future with you built on mutual respect for the first time.

What goes around comes around sorry

So perhaps she is having an affair now, how do you know what he texts ?

But you talk with her, and see if she wants to try and make your relationship work. To be honest I have no idea why she is still with you, and perhaps she is making plans on not being. You and her need to talk and perhaps get counseling if you want to try and make it work