Flaccid Penis

Ok so I know that this is strange and personal but I honestly don't know what else to do.

Me and my boyfriend were messing around and we were gonna have sex. Well he put a condom on and everything and I climbed on top and as soon as he was inside me his penis went soft.

So we continued with foreplay and tried again. The same thing happened.

After trying a total of 6 times and wasting so many condoms we decided to stop because we were both frustrated and tired.

I asked if it was because of me. I'm really tight and it's honestly painful but he said it didn't feel any different then a firm grip.

As we lay there discussing the matter he began to cry. He hasn't had the best health record. He used to drink and smoke and he currently dips.

But nothing stood out as to why he couldn't keep is penis hard.

We are both puzzeled about this issue and are slightly concerned that there might be a medical condition.

Does anyone have any ideas about what might be going on?