In Which Carnita Writes a Letter to Dan Savage

I wrote this letter to my hero today. We'll see if he answers!

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Dear Dan,

I'm a polyamorous heteroflexible woman in my mid-twenties, and I've been with one particular male partner for a few months. The sex is AMAZING, and trust and vulnerability come easy between us. Nothing is off limits, and every sort of sexual adventure that might strike our fancy seems possible. However, neither of us is very experienced with some of the kink that we're interested in exploring together, so we're on a steep learning curve. 

There's one thing in particular that I want your advice about. My honey has been feeling a strong desire for some gender play lately (and he works for himself, so he can pursue this desire to his heart's content). Not only does he want to transition into a more feminine role--dressing in women's clothes, adopting more feminine mannerisms, etc.--but we also want to figure out ways to incorporate his new gender expression into our sex life. I am so excited that he wants to explore this new avenue with me, and I am enthusiastic about doing whatever I can to make his fantasies come true. I want to treat him like a lady! He has mentioned being taken out on the town in drag and playing with clothes and cosmetics together, all of which sounds like lots of fun, but how about the more erotic side of things? I don't even know where to start! I've always been pretty sexually submissive and feminine, I'm petite and delicate while he is tall and muscular, and I have never even thought about how I could play up my masculine side in a sexual dynamic. But if I had a way to conceptualize my approach, I know I could immerse myself in the experience and have a great time with it. The tips I've read on a few BDSM info sites seem a little corny and don't exactly fit my sense of aesthetics. So, do you have any tips or tricks to offer about how I can masculinize myself in erotic situations and/or make him feel more feminine? Can you recommend some good resources for queer-positive erotic lit that could feed my imagination? 

Thanks Dan! I read your column religiously, and I have been saving my first letter to you for something that felt really important and interesting. I hope you have time to respond. Feel free to edit/condense.

His Gender Liberation Playmate