>>408As
>>351 said, you need to give it some time, test the waters before jumping in. You mentioned in your first post that she's got image issues - give her some nice, honest compliments: tell her she looks good in that shirt, her hair looks good etc., that should be a nice way to build up her self image and give her some very subtle hints that you think she is attractive.
I don't know how you normally interact with her, but asking her how her day's been, and just sitting down and talking to her, seeing a film together will help you get closer - be sure to listen, ask follow-up questions aka be honest, interest & natural with her.
If you're not already, maybe her doing more things around the house.
Take care of yourself - maybe working out, dressing smartly, using some subtle cologne - maybe use some pheromones?
http://www.androticsdirect.com/home.phpJust don't rush it - don't try and do everything at once. Keep it consistent and keep it up. You might be able to judge your chances by how she responds to this.
If you feel that she responds positively to this, you could try a risqué approach: snatch some of her panties (preferably used ones) and leave them in your room for her to find them. That should give her a very strong indicator that you fancy her. If you think it'll work, you can blow your load in the panties before leaving them in your room. Don't leave them out in the open, but don't hide them either - you do want her to find them. You could try a variant and cum in her panties and leave them in the hamper once you're done - she should notice when she gets them washed.