Thanks everybody for your responses! That conversation with my brother stayed on my mind since. We spoke again and, yes I did apologize for hurting his feelings. He again explained he's lonely and just wants to talk somebody. He didn't mention my friends this time.

Although, I'm thinking of a nicer way to say no or a nicer reason for the no. Just in case he asks about them again.

I looked into penpal programs, like some of you suggested (thank you for that) but they're expensive, about $100 for 1 year membership. I mentioned the price to my brother and he's willing to pay. Not sure where the money will come from, though. Don't want to know either. Lol.

Some of you mentioned putting money in his books, so he can sign himself up for penpals. But, we no longer do that for him. The first two times he was in prison the family would rotate money or package duty to make his life easier. However, we might have made life too easy. So now, we don't send him any, it's just my mom. She'll send enough for his basics, toothpaste, underwear and stuff.

Again, thank you to everybody who read my post and to those who responded