Crossword puzzles, word games, daily affirmations, photocopies of pictures since he can only have six actual photos, mandalas to color, because he has colored pencils, bookmarks I made with quotes that help him or cheer him up, postcards with places we've been and places we want to go, current events I print out, especially science & space discoveries, lyrics to songs we listened to, poems, and letters every day. One thing we do is write each other questions. I ask him to share his best childhood Christmas memories, when he learned to ride a bike, his favorite books as a kid, his pets...tons of questions about his life, his dreams, where he wants to travel, oh, and sometimes I send him erotic stories about us (blush) and wedding & honeymoon ideas.
I'm lucky because we're both writers, so letters and stories and all these things come naturally to both of us. We have learned so much about each other, it amazes me.
Have fun and open your heart. :)

I send my guy letters but I am now considering to send him things that he can color with the colored pencils that he can get. I want to start sending him post cards of places I want us to go. I'll likely send erotic ideas// lol.. We do learn so much about each other through letters.. I want to explore everything about each other.. I want to be married to this man one day.. thanks for sharing!

Hmmm i think the longst ive done was 37 pages over 4 days all hand writien. We talk about everything and i do mean everything :) i send him cards, photos, books, magazines, socks, jocks, and ive even sent tops that he need in the last place he was at!
We are both writiers so its kinda easy for us oh and we have been writing for over 3 years now its the cheaps and easy way for us to keep in contact.

I am on the same page as @ angeladam. I send as much and as many differerent things as I can. I visit often, but anything that I can do to pass the time, I do. I love sending things he can color or use his brain to pass the time. I send lyrics of songs we would listen to on road trips and romantic dates. I also too, write about our wedding and honeymoon that will happen when he gets out. I think that most of what i do revolves around the future that we have so much hope for. I send pictures of me that are of everyday things, some sexier then others, but more of places that i go, and our pets, and friends that we share, and family that he misses dearly. I read a lot of daily meditations, and i love sending those. He has said that they have helped get him through many tough days.
Keeping it fun and frequent has been very helpful.
And ideas though would be helpful. The longest letter ive written was about 8 pages er so. Some times i run out of things to say. lol

I am on the same page as @ angeladam. I send as much and as many differerent things as I can. I visit often, but anything that I can do to pass the time, I do. I love sending things he can color or use his brain to pass the time. I send lyrics of songs we would listen to on road trips and romantic dates. I also too, write about our wedding and honeymoon that will happen when he gets out. I think that most of what i do revolves around the future that we have so much hope for. I send pictures of me that are of everyday things, some sexier then others, but more of places that i go, and our pets, and friends that we share, and family that he misses dearly. I read a lot of daily meditations, and i love sending those. He has said that they have helped get him through many tough days.
Keeping it fun and frequent has been very helpful.
And ideas though would be helpful. The longest letter ive written was about 8 pages er so. Some times i run out of things to say. lol

the longest letter I've written was like 9 pages but we talk so much so I don't write as much.. I've sent him pictures of me and some of pictures are something you would find in maxim magazine of me . I do those maybe every 3 or 6 months and i send him books sometimes but they are only allow so many pictures so try not send too many to my hubby even letters he only allowed like 20 letters which he sent a lot of them back to me due to the policy which i threw them out. so keep that in mind if you send him to much they might make him throw them out at least where my guy is

I'm Pretty new at all this myself but I try to write him almost everyday. If I'm not writing a letter I send him a card with a few uplifting words, just to let him know I'm thinking about him. I send pictures and yatzee score cards lol. My longest letter has only been 4 pages but I know that he is loving the letters and i'm not afraid to over load him anymore. He loves the letters and I love getting his :)

Longest letter for one day was 4 pages long. I sent my letters every other day, so I send more than one days letter at a time. I send him sermon notes, devotions and cards.
Periodically I order him a book, he's only allowed so many, but he shares books with other inmates. I order used books on Amazon, so I get good deals on them, and concider it as a contribution to the inmates.

I have sent an 11 page letter and that was front and back. We also both send a list of songs we like a lot. I send a sexy/x-rated letter that I make up on hoochymail.com he loves that too or sometimes I will just have a letter that I'm saying all these sexual things. Also do a "photo shoot". This is a new thing for me. So far so good. It's driving him wild. I've done hand prints with our son. Printed his horoscopes crosswords and a few other fun things. Good luck! I'm sure whatever you do he will love and appreciate that! :-)