Should I be concerned that my boyfriend wants me to show more of myself?

We have a great, loving relationship going, and he's very affectionate and attentive to me. He is also very proud of me, and would like for me to notch up the level of iness in my dressing. Specifically, he would like for me to go bra-less under my t-shirt or dress, or wear a top that leaves little to the imagination. I'm not comfortable with this, both from the stares that I draw and not understanding his motivation. As a matter of fact, I felt embarred when I did to some degree, like I'm really transgressing! Would you help me in understanding what does he want from my doing so? Is this simply a way that he has of liberating me from certain Tennessee inhibitions?