I often talk in innuendo. I get it, i'm immature, which is why I haven't had any success with this gaming stuff yet. Chicks are like, "gosh, you're so dirty" or it fails like a lead balloon. Either way, it doesn't work and I seem like a sleazy guy, but I can't help it. (like Michael Scott from the Office. Yeah, a bad role model, but I love it. My favourite is the 'that's what she said'. Some days I can go almost entirely saying it.)

Is there any good time, or reason, to be doing this, or should I just be conscious of and not do this? It does sometimes get a laugh. is it a bit too risky, or is it a good way of testing the seual waters? Or, do I come across as immature? Some chick said after I dropped one, "you so need to get laid". But not in a good way, in a disapproving way.

Wait for the moment, drop the bomb. If that's what she said jokes are what you do, then enjoy... just don't overuse it. Honestly I wouldn't stick with it; just take some time to think up more clever or subtle innuendo.

Hell, "Can I come inside?" after ringing a girl's doorbell can count as innuendo if you do it right. A lot of people use and advise a good sexual frame, just find the line between sexual and seedy. Keep at it

Now I am a firm believer in using sexual innuendo's but there is right way and a wrong way to do them.

Personally, I use them a lot when first interacting with a girls, but I make it more humorous and it sets me as a very sexual/funny person. The key is to not apologize for it. If she makes a comment about it being gross or something, you have to be unreactive, say "get over it" or something to that affect. Girls are looking for congruency between what you are saying and how you are acting. If congruence is not there it will give you lower value and you will just sound creepy and gross.