How to transfer photos from a external hard drive to put them on my ipod?

Hello everyone, I wonder if I could get someone to help me with this, I am using a window 8 or ten and I am on match and the apple music and now you know the cloud that you have five free to get you going, non I am on the 50 gb and will take begger if I need too, now my question is this, I have about 3 to four hundred photo and with the help of a friend I did give it a name, now, I would like to sik it to my ipod touch or ipad so that all those pictures get on the cloud, everything from the hard drive is now in one cloud or another, can someone help me with instruction or article to sink pictures, I have never done this before. those pictures were taken by a camera not a apple divise, can I still do it?I have a lot of pictures about family and I sure would like to as much possible not loosing them.
thank you in advance