How do I get my songs in ITunes to stop skipping when crossfading?

I like my music at parties to crossfade in and out and keep the mood going. Unfortunately on both my Gateway Desktop and Toshiba Laptop the beginning of the next song always skips terribly for a bout 2-3 seconds. What do I need to do to fix this problem? It's driving me nuts!!!

- iTunes purchases by:
iTunes Store: Transferring purchases from your iOS device or iPod to a computer
- For other music you need a third-party like one of those discussed.
Copy music

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