This looks like a job for the forum's resident womanizing jerk! But since he's not here, I'll step in.
All kidding aside, I've had a wide variety of girls nervous about getting naked around me. Rape victims, child molestation victims, overweight girls...you name it. Except anorexics. Fuck, get that shit away from me. Those chicks look like Feral Ghouls.
Anyway, here's SimuLord's Foolproof Guaranteed To Work[footnote]Not guaranteed to work. If I were that good I'd be too busy getting laid to post here.[/footnote] Guide to Female Body Image Improvement For Make Benefit Glorious Nation of Kazakhstan:
1) I have found in my travels that most girls with body issues don't have body issues. What they've got is trust issues. It's not that they're necessarily disgusted with their naked form
per se, it's that they're scared to death that you'll scream (to quote one of my ex-girlfriends) "Away, vile creature!" The first step is to make them feel secure. Unless you have a body like a Jersey Shore cast member, chances are good you have an imperfection of your own---cracking a light joke at your own expense will give her the sense that you're as nervous about her opinion as she is of yours. When the tide is turned and she's reassuring you that she finds you attractive? That's when you pull out the "see, that's how I feel when I look at you."[footnote]And for gods' sake, mean it. I want to cut the balls off any guy who's been insincere with his girl because I have to clean up that mess when she gets to me.[/footnote]
2) If you think you can get away with it, make a "house rule" that "sorry, you want to sleep in this bed, the clothes are coming off." Note: This is a serious test of her trust. Not only is she probably afraid of what's going to happen (unless she's got a monumental sex drive), you're going to have to resist your own carnal urges---at least at first---to convince her that she can be naked around you without the whole thing being instantly oversexualized. Pull this off and she'll trust you on far more than an aesthetic level. And that means more naked cuddling. And sex, when you hit that point. So much easier to keep a sex life alive when you don't have to pry the flannel PJs off her.
3) Affection, affection, affection. While it would be horribly sexist of me to suggest that women are like dogs, I call 'em like I see 'em and training a woman has a very Cesar Millan-like quality to it. (unless she's a domme, in which case you'll probably just fight to the death. But I'm assuming no fetishes here. And I prefer submissive girls myself.) Consider the most recent episode of Extra Credits. Y'know, the one about "operant conditioning"? Y'know how Daniel Floyd points out "it works on humans"? I believe you can do the math. Teach her to associate getting naked around you with heightened sense of emotional fulfillment and intimacy. She'll not want to put her clothes back on. (and I am
sorry if this came out sexist speaking from ample experience[footnote]I just calls 'em like I sees 'em.[/footnote].)
Do this and you'll be doin' it like they do on the Discovery Channel before you know it.