Relationship advice needed!

I found out my boyfriend was messaging sexual jokes to his friends that are girls. I also found the he was emailing local singles. I asked him to stop doing both after we really fought about it. He said he would. I checked his laptop the other night and found that he did both very recently. We are high school sweethearts and have been together for 5 years. I do have a history with insecurity and in the past have really made things difficult. We were finally at a good point until I randomly checked his laptop a few weeks ago and found that stuff that he's been doing for at least 4 months. How should handle this?

Breezy, if you have problems with insecurity, then this guy is definitely not the guy to be with. If you don't have trust in your relationship of 5 years, then your partnership has no foundation to build on. Regardless of your insecurity, your BF needs to respect you and if he did, he wouldn't even think about emailing local singles. You would be his total focus. He is contributing to your insecurity whether intentionally or not... but after 5 years, you pair should have a good idea about each others likes and dislikes. You, on the other hand, basically need someone in your life who accepts you totally for who you are for you to develop trust to eventually get over your self confessed insecurity. You're stuck between a rock and a hard place here and if your BF can't/won't contribute to a 'comfort' environment then you need to seriously think about moving on.