1) If I stuck by him in jail--why wouldn't I stick by him now?
Well, because he is a liar, a cheat, an addict, you don't believe him (which is entirely reasonable), he wanted you to smuggle stuff into jail, thereby putting you at risk.
He cheated on me. Twice I know about. Once he told me--the day before he broke up with me. Slept with a girl that was supplying him money and drugs. He said he felt obligated. Whatever that means. (Side note: two others he lived with were using. Heroin mostly. IV.)
If you have not been tested for STDs you need to and you need to cut all ties with this guy! Please before something worse happens than getting your feelings hurt.
During the years I was 16-20 I was in love with, and dating, and came within 6 weeks of marrying an addict. He used anything he could get his hands on- heroin, pills, alcohol, pot, whatever. I never used any drugs at all. I thought love would conquer all. It didn't. He hit me a couple of times, stole from me and my friends, drove drunk with me in the car, almost choked me. "He was stoned, he was high, he doesn't even remember" - that's what I told myself for staying with him through this sh*t.
He sobered up now and then but always went back to drinking and drugging. He went through a rehab successfully, was straight for 9 months and we planned a wedding - until he started drinking again. Then I FINALLY said goodbye. Gave back the ring, uninvited the guests, returned my dress. It was the best thing I ever did. Oh and he was my first lover, btw.
Dump this guy. He's not your best friend. Find someone who deserves you and treats you well. You'll thank your lucky stars you got away.