Leaving your comfort zone is the best way to take on board new experiences, especially in terms of social interaction.
You could try saying something really weird (but that you find hilarious) to someone who you don't know, for example, a woman in a shopping centre. Actively seek a negative reaction, so that when you get that it isn't a big deal. Just do it for your own amusement, and you will learn that how new people perceive you is no big deal.
As for protecting your image, just don't worry about your image. At the moment I have an image of you that is extremely defensive and unadventurous, purely because of how you regard yourself. Break down this barrier and your image could be whatever you like.
As an example of going out and learning not to give a shit about how people think of you, just go up to someone and say:
"This bloke came up to me, and he said 'you rotter'... I said 'you what?'"... much like in this video:
http://www.youtube.com/watch?v=jTifRi3qDkU
If you find it hilarious then you really won't care what they think of you, and that is the right vibe to give off.