I've been dating this guy for about 22 months now, but all of the accumulated issues are weighing on me now.
First off, after 13 months of when we first had sex, he told me about his first encounter of having oral sex with an ex-girlfriend. Something he indirectly led me to believe that was his first time as well when we did it together.
Secondly, as we were in a long distance relationship at the time of our senior proms, we believed neither would go if we couldn't go together. I did not go, but he ended up going, completely surprising and hurting me.
With just these two problems constantly eating at me I wonder if its time to look for someone new.

Neither of you were in any position to deny the other the chance to attend their senior prom.

Long distance relationships never work either... and besides, you really are NOT dating someone when it's a long distance relationship. You both physically have to be in the same place to date, Dating means going out... watching a movie, eating together, holding hands. None of which you can do online.

We were together in person for about 8 months.. we have 1 more month to go before we are together again..

Can't either of you find another unattached person near you to date?

No.. I'm still in love with him.. I've tried breaking up but he always ends up crying and begging me to come back..

Then I guess you deal with the issues and move forward since you love him and can't end it.

Actually regardless of all of that. If there are a lot of problems in a relationship... then its doomed and the smart thing is leave. Hate to say this but he sounds like a loser. And I'm saying this as a guy. That's a really lame passive -agressive behaviour he's pulling to control you.

As little as you've been together, one thing there shouldn't be is a lot of prolbems. And with the little times you've actually been together, you are still in lust, not love. Trust me.. this early in a relationship you REALLY haven't gotten to know each other yet... in person dating for about 3 years... you get to know the real person, before then you are on your best behaviour and not acting relaxed and yourselves, you are trying to be what you think you should be and what you think the other wants, not yourself. That never lasts and when it ends you see each other for who you each REALLY are. And thats about how long it takes real love to grow....lust happens right away and eventually dies down, it never lasts forever and usually dies off by the 2nd or third year. THey are hard to tell appart without a lot of relationships under your belt.

Well in all actuality everything you stated is something small to a giant. In a relationship it should consist of honesty, trust, and communication. If you feel like he's not showing you any of these three things then yes, it's time to think things over. I think if you address issues of lack of communication on his part in the beginning he'll know what & what not to do in the future. If in the future he continues to do this then I believe it's time to move on. A person will only do what you allow :)

As you get older, you will find and should never discuss past sexual partners, your next partner ( if you leave this one) may have had 5 or 6 past sexual partners. So if he had sex, or did not have sex, is not, and should not be an issue.

AS for as a the prom, what was promised, or was it assumed, if this is a long distance relationship, then going to the prom is a large issue, in life and you both should have went.

In the aspect of real issues, if this is it, then there is very little issues besides the ones you are making for yourself.

Love or not, when you have had enough of the one you are with, and cannot resolve whatever issues you have, then one or both will be sick and tired enough to end it.