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12 a.m.: Before going to sleep, BF and I begin casually discussing men we know of who wear bras under their clothes. 9:15 p.m.: After some cursory making out, we are having rollicking, hard-driving vanilla sex. 9:05 p.m.: I accept the Quickie Challenge. I actually did not even know it was an option - our sex life has become increasingly baroque over the course of our relationship, but we have never yet had a sexual encounter that clocked in at under 45 minutes. 9 p.m.: My boyfriend suggests a quickie, which we have never done before. 8:15 p.m.: As we cook dinner together, I get slightly depressed at the thought of being 28 and already sacrificing sex for sleep. Our typical sexual routine (mutual oral sex and rim jobs, dirty talk, and at least half an hour of actual fucking) takes a reserve of energy and enthusiasm, and right now, it seems like a mountain I cannot climb. I know part of - most of? - the reason we got together tonight was to fuck, but I question my ability to perform. 9 p.m.: Back in our clothes and freshly fucked, we bust out some sorbet and settle in for an evening of cuddling and Hulu.ĭAY TWO 8 p.m.: BF comes over after work, and I am exhausted. The whole time, we talk about what a naughty, dirty girl he is. 8:30 p.m.: We have sex first with me on my back, then with me on top. 8:20 p.m.: He says, “I’m a bad girl with a big dick.” In return, I give him a blow job. I put a layer of pink lipstick on his mouth, and then have him kiss me all over my body. 8:15 p.m.: I give BF a shiny pink bra to wear and squeeze his chest through it. He’s never worn this pair before, and I like the way his dick sticks out of them. Within the past few months, I have come to love the sight of my man in panties. 8 p.m.: The panties discussion turns into fooling around while he wears some frilly pink lace panties.

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It gave me a break from trying to be the perfect, sexually desirable heterosexual female (a pursuit which had previously consumed my entire sex life) and a free pass to enjoy myself in brand-new ways.

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When he put on panties, it felt like it gave me license to be bossy, ask for the things I wanted, role-play out all sorts of dominant fantasies I never even knew I had. But very quickly, I found that I actually liked it. The first few times he dressed up for sex, I was mostly just being supportive and found it a little silly. The shock that we both had anticipated over BF’s revelation never materialized I told him I loved him, and we could try whatever he needed to try. But very soon after embarking on my relationship with BF eight months ago, I realized I’d found a guy who was definitely the former and very likely the latter. The idea of a partner that I could spend the rest of my life committed to seemed even more absurd. And I definitely never imagined being with a guy who got off on cross-dressing - it seemed totally absurd.

I’ve always been a little bit slutty, but kinky stuff just never seemed to do much for me before I met BF. 7:35 p.m.: BF tells me, “I want you to look like a woman and me to look like a little girl.” It makes me want to jump him.ħ:45 p.m.: We can’t stop poring through the catalogue and start getting a little handsy with each other. What begins as a discussion about what sexy panties I should get turns into a discussion of which sexy panties my BF should get, which turns into a discussion of what sexy panties we should get together.

This week, the Female Editor Teaching Her Cross-Dressing Boyfriend a Lesson: 28, female, Greenpoint, editor, in a relationship, straight.ĭAY ONE 7:30 p.m.: A Victoria’s Secret catalogue arrives in the mail today. Once a week, Daily Intel takes a peek behind doors left slightly ajar.