sex diaries

The Female Editor Teaching Her Cross-Dressing Boyfriend a Lesson

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Female Editor Teaching Her Cross-Dressing Boyfriend a Lesson: 28, female, Greenpoint, editor, in a relationship, straight.

7:30 p.m.: A Victoria’s Secret catalogue arrives in the mail today. 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.
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.

7:45 p.m.: We can’t stop poring through the catalogue and start getting a little handsy with each other. I’ve always been a little bit slutty, but kinky stuff just never seemed to do much for me before I met BF. And I definitely never imagined being with a guy who got off on cross-dressing — it seemed totally absurd. The idea of a partner that I could spend the rest of my life committed to seemed even more absurd. 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 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. The first few times he dressed up for sex, I was mostly just being supportive and found it a little silly. But very quickly, I found that I actually liked it. 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. 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.
8 p.m.: The panties discussion turns into fooling around while he wears some frilly pink lace panties. Within the past few months, I have come to love the sight of my man in panties. He’s never worn this pair before, and I like the way his dick sticks out of them.
8:15 p.m.: I give BF a shiny pink bra to wear and squeeze his chest through it. I put a layer of pink lipstick on his mouth, and then have him kiss me all over my body. I spank him over my lap, slowly.
8:20 p.m.: He says, “I’m a bad girl with a big dick.” In return, I give him a blow job.
8:30 p.m.: We have sex first with me on my back, then with me on top. The whole time, we talk about what a naughty, dirty girl he is.
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.

8 p.m.: BF comes over after work, and I am exhausted. I know part of — most of? — the reason we got together tonight was to fuck, but I question my ability to perform. 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.
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.
9 p.m.: My boyfriend suggests a quickie, which we have never done before. 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.
9:05 p.m.: I accept the Quickie Challenge.
9:15 p.m.: After some cursory making out, we are having rollicking, hard-driving vanilla sex. I don’t come and don’t mind it.
12 a.m.: Before going to sleep, BF and I begin casually discussing men we know of who wear bras under their clothes. I can’t imagine telling my friends about our sex life — not because I’m embarrassed, but because I used to be such a sexual oversharer, and not talking about us feels like a nod of respect to the seriousness of our relationship.
12:15 a.m.: We conclude that he probably doesn’t want to get caught with an underwire popping through his shirt at the conservative company where he works.
12:20 a.m.: We fall asleep spooning.

3 a.m.: I have a nightmare where all of my ex-boyfriends run a record store together, and I wander in off the street by accident. They are all there, standing around in the back. One draws a connect-the-dots image of himself ejaculating a bunch of balloons and tries to hand it to me. I refuse it, then wake up, trying, and failing, to make any sense of it.
2 p.m.: I promise to call BF and then forget to call BF; he is already in a bad mood from work and this leads to our first honest-to-God actual fight. We fight over the phone, as I walk back to my job from lunch, and I burst into tears in the lobby of my office.
3 p.m.: I close my office door and try to cool down. I met BF over a year ago, at a friend’s D.J. night; he was in hookup mode and I was in I-just-got-dumped-don’t-touch-me-I-want-to-die mode, so we didn’t connect. We did, however, become friends. Soon enough, I was ready to be touched again; I set my sights on him, and it’s been happy trails ever since. We’ve never had a real, angry fight like this.
3:20 p.m.: I think about my boyfriend from college, and how horrified I was when he asked me for a rim job. I think that I wouldn’t be up for exploring kinks with a man I loved less than BF — having him close makes everything feel safe, like I can take any risk I want and I can’t fall. Ugh, do I sound like a romance novel written for awkward teenage virgins or what? Barfsville. And yet, it feels very true.
4 p.m.: I freak out about the fight for the rest of the day and can’t get anything done.
8 p.m.: We get on the phone and furiously make up, deciding that the whole fight was a misunderstanding. It often feels like BF and I spend every waking second together, but he does have his own apartment — a total bachelor crash pad in Astoria — and he is there tonight.
8:30 p.m.: After we get off the phone, we send each other goofy text messages to wash away the taste of the fight.
11 p.m.: Too emotionally exhausted to masturbate, I just fall asleep.

8 p.m.: BF comes over after work. We’d been planning on going to a restaurant we like across the neighborhood, but end up crapping out because of the cold and just order in some Chinese food instead and watch a movie.
11 p.m.: While looking at Facebook together, we catch a glimpse of his ex, and I start giving him a hand job while I taunt him about being a dirty slut for having fucked her. Though we’re monogamous, others make imaginary guest appearances in our bed quite often — friends of mine, my ex-boyfriends, his ex-girlfriends. Sometimes we have fantasy threesomes; other times, we just describe particularly hot sex that we had with other people.
11:15 p.m.: He jerks himself off as I kiss him. My panties have a tear in them, and BF requests that I wear them to sleep so that he can rip them off me when we have sex first thing in the morning.

11 a.m.: We wake up, and very soon BF is going down on me.
11:15 a.m.: I go down on him, while he jerks me off almost to the point of orgasm and then stops (at my request).
11:25 a.m.: We spend a few minutes trying to cram his very big dick into my very average-size vagina, and then we have slow, intense sex with me on the bottom until I have an agonizingly drawn-out orgasm.
11:40 a.m.: I pause, post-orgasm, recover, and then try again on top. As promised, he tears at my red lace panties. Afterward, we contemplate saving them as a memento, but end up chucking them.
6 p.m.: BF’s parents are in town. They take us to a fancy dinner and a performance of Wicked. While I answer their innocuous questions about my career, I try very hard not to think of the sex we had in his childhood bedroom when we visited over Christmas, where I pretended to be his high-school English teacher.

10 a.m.: BF leaves after a night of naked snuggling, so that I have some time to edit. I am supposed to make progress on some work projects today, but somehow, between laundry and other totally mundane things, the day slips away from me.
7:30 p.m.: BF comes over and we make out. I put a pair of purple cotton panties on him and some black thigh-high stockings. We are both crazy for black thigh-high stockings and the way they feel on bare skin. I love looking at BF in lingerie for some high-minded reasons — because it shows how vulnerable he is willing to get with me, how close we are, and how much he trusts me. But really, I think I like it most for the same reason people like lingerie on women: I like the feeling of satin and silk and nylon under my fingertips, and I like the visual reminder that I am about to get laid.
7:35 p.m.: We commence in the 69 position.
7:45 p.m.: We have sex that moves through an array of further positions as steadily as a yoga class, dirty-talking about what a nasty girl he is the whole time.

5 p.m.: I leave from work the first second I’m able to and still feel like a totally drained, brain-dead zombie-lady. It’s freezing outside, there is a crazy guy stalking back and forth in front of my office building yelling, and some dude on the subway is passed out and drooling onto a magazine picture of Justin Bieber. I heart New York?
7:30 p.m.: BF comes over and we make an enormous meal. I didn’t think I had the energy to have sex tonight to begin with, but this truly seals the deal (for both of us, I hope — I hate turning down sex, it makes me feel like such a loser).
10:30 p.m.: Nope — BF is still up for it. I want to, but I feel like I am literally about to pass out. BF tells me he is tired, too.
10:35 p.m.: BF jerks off in bed, next to me. At first, I plan to just watch, but I start getting into it, rubbing his face and chest, talking dirty. I get very turned on watching this in general, and think of asking to join in, but when he finishes, I feel relieved — I really did not have it in me (pun intended).
11 p.m.: We both get under the covers, exhausted, but then can’t stop talking and joking and goofing off with each other. We come up with a lot of joke band names.
12:30 a.m.: We finally turn off the light, and BF spoons me.

Totals: one hand job performed; one hand job received; three acts of oral sex performed; two acts of oral sex received; four acts of intercourse (two of which involved a man wearing panties, one of which involved a woman wearing panties).

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The Female Editor Teaching Her Cross-Dressing Boyfriend a Lesson