Hey there, you sound like me - only I'm a girl.
I am just finishing out my first year at a community college, which is great for me because it costs less.
I'm EXTREMELY shy, although no one would know. Going into the first day of school I said to myself "It's time to make some changes and get out of this shell!" So that's what I did. I smiled at people and they came to start conversations with me. I sat in different areas of the class each time to meet new people. It worked out well and I forgot about how shy I was. I know this sounds weird but wear something your first day that you feel represents you - and that makes YOU feel good.
I wore a skirt my first day to show off my tattoo, which was a great conversation starter with both men and women. Try approaching just men to say hi, if it'll make you more comfortable.