Cross-dressing With Sis

I’m 20 years old and I have been cross-dressing since for the last seven years. I secretly wear my older sister and mother’s clothes and innerwear. Last year I came out to my sister about my cross-dressing and she was very accepting about it. I want her to dress me up and have fun with it, like we used to do when we were very young. How do I go about that? The very thought of being dressed and made up by a female excites me too much. I’m 100% straight though.
–Anticipating Cross-dresser

Um, I fail to see how being straight affects this conversation, but thanks for informing me. In any case, it’s really great that your sister is so cool with you being a cross-dresser. Bravo. However, I wouldn’t recommend that you ask her to dress you up. Why? Because dressing in women’s clothing is a sexual act for cross-dressers, and it’s not a good idea to involve your siblings (or any relatives) in your sexual life. As you yourself pointed out, the very thought of a woman dressing you up in her clothes is sexually exciting for you. You might as well ask her to jerk you off. Why would your sister want to be involved in helping you get turned on? It shouldn’t be a problem to ask her if you can borrow her clothes and makeup, but don’t ask her to help you dressed on top of that. I see only disaster ahead.

Oh, and be sure to return her clothes and makeup to her in the same condition she gave them. Nothing sucks more lending someone a cute top and getting it back with makeup stains all over it.

Bringing Drag Into The Bedroom

I am a middle-aged man and I have a serious problem. I like to shave and wax myself, wear false breasts, ladies’ inner wear, saris, and makeup before having sex with my wife. I like to play the female role in bed. I want my wife to dress up as a man and make love to me. In short, I want to be the “wife”, while my actual wife becomes the “husband”. I only want this maybe 20 percent of the time we enjoy sex. For the remaining 80 percent, I am fully happy as the husband. I do not want a permanent reversal of roles. I am not a transsexual. I just want more “masala” in our sex life. I am quite happy as a man, a husband, a father and as a successful person in my career. How can I make my wife understand and cooperate?
–Looking For Some Spice

Um, you tell her. Just talking to your partner about your sexual desires is really not so hard. The challenge is doing it in a way that is respectful of the other person’s boundaries. So my advice is this: sit her down in a calm, private, non-sexual setting and tell her what’s on your mind. Tell her everything you just told me: that this isn’t something you want all the time, that you’re very happy in your marriage, and that your need to explore the boundaries of gender performance does not mean that you are gay or transgender. She may be horrified or she may be delighted. It’s more likely that her response will fall somewhere in the middle of the spectrum, but either way try to keep things calm. If she agrees to go with this then you have to assure her that you want to start slow and then stay true to your word–start slow. Don’t go right into full-on drag. Start out with some role-playing first—a few encounters where you act like a “woman” and she acts like a “man”. You are, of course, dealing in stereotypes about how men and women are supposed to behave and feel during sex, but those stereotypes are powerful and there can be a very real erotic charge to transgressing them.

Anyway, start off with some role-playing, and then you can work your way up to having sex in drag. And also, don’t look at this as trying to make your wife “cooperate” with you. For you to successfully incorporate this fetish into your sex life, you both need to be willing and happy participants. This means that you need to place as much emphasis on making the fantasy pleasurable for her as on making it pleasurable for yourself. Ask her what she needs to make this fantasy a happy thing for her and how frequently she feels comfortable participating in it. In the best case scenario you’ll both be thrilled with this new aspect of your sexual relationship and it will enable you to bring a more nuanced and mutually fulfilling attitude to your more vanilla sexual escapades. Even if this isn’t the fetish that rocks her world, if you’re kind and considerate about putting it on the table she will hopefully at least be neutral about participating in the whole thing. And don’t forget to ask her about her unspoken fantasies are and how you can bring them into your sex life! Remember, sharing is caring.