Programming notes

I have been wearing bras and panties with stockings for so long now, it’s become a part of me, and I was wondering if you have heard of this before.
Sent From Samsung Mobile

People wearing bras and panties and stockings—that is something I’ve heard of before.

A quick programming note: Some weeks, half the questions I get are longer than the column itself. I can jam 1,250 words into this space, provided I avoid using longer words when shorter ones are available—e.g., “gay” has one syllable, “homosexual” has five; “asshole” has two syllables, “former Arkansas governor Mike Huckabee” has 12. Suffice it to say, very long letters rarely make it in. So while I usually appreciate letter writers who get to the point—the more succinct the question, the better the chance it will make it into the column—it’s possible to be too brief.

Such is the case with your letter, SFSM, which is reproduced here in its entirety. I know what kind of phone you have, but it would be more helpful to know if you are male or female or SOPATGS.* I’m guessing you’re a dude, otherwise you probably wouldn’t feel conflicted about wearing bras, panties, and stockings. So despite what I’ve learned lurking on Tumblr—never make assumptions about other people’s gender identities, we are never going to run out of porn—I’m going to run with the “dude” assumption.

Anyway, SFSM, men who wear bras, panties, and stockings—I have heard of that before, yes. Bras, panties, and stockings are things that some men enjoy. But I once got pulled aside at a party by a butch dyke who confided in me that she likes to wear lacy/girly bras and panties under her Carhartt pants and flannel shirts. She too wanted to know if I had ever heard of someone like her before—a woman who essentially cross-dressed by wearing women’s underwear—and I had to tell her that I hadn’t. But that butch dyke enjoys wearing bras, panties, and stockings for the exact same reason you and many other straight guys do: the frisson of transgression, the thrill of having a sexy secret, the reveal to a new partner. She didn’t seem particularly conflicted about her non-butch-dyke-normative tastes—heck, she seemed rather pleased with herself. You should consider her a role model, SFSM, and follow her example.

* Some other point along the gender spectrum.

You know that thing you sometimes do when your girlfriend asks in the heat of the moment what you want to do? I don’t mean stare at her blankly—that’s the wrong thing to do—I mean choosing something at random. Do that thing every time. Randomly pick something from your established repertoire and tell her you wanna do that thing right now. Then do it, MMM, provided she indicates that she wants to do it too. If she indicates her desire to do it verbally, then you can get right down to it, i.e., you can be a bit aggressive. If her signal is physical or nonverbal, then you should ease into that random selection much more gradually, so she can redirect and/or ask you to choose again if that particular random selection doesn’t work for her.

Two practical tips: first, female condoms. I realize you’re a dude, and I realize that female condoms are more expensive than male condoms, but they’re a terrific option for buttfuckees worried about cleanliness. For readers who may be unfamiliar with female condoms: They’re a bit larger than regular condoms and they get tucked inside the orifice that’s about to be fucked—vagina or butt—and remain in place during sex. A bare dick goes into a female condom clean and comes out “clean.” (Technically, that bare dick comes out covered in lube and semen—but that’s the mess people are after, not the mess people worry about. For added safety, the top can wear a male condom.**) The female condom is removed after sex, SUB, which you can do alone in the bathroom—that way, if there is a mess, your loving partner/special guest star will never know.

Second option: frottage. It’s not bottoming—no penetration—but it’s a worthy and pleasurable substitute. Your loving partner/special guest star puts his lubed-up dick between your thighs, right at the top, you close your legs, and he plows away. If you’re on your stomach or doing it doggy style, SUB, you can put your lubed-up hands between your legs and cup your partner’s cock while he thrusts back and forth. You’re not being penetrated, but your taint, the outside of your hole, and your sack are all getting stimulated. Frottage is also a good first step for people who want to experiment with anal play but aren’t ready for penetration.

** As several people have mentioned in comments, and as many of you have emailed me to let me know, using a male condom and a female condom together doesn’t make things safer—it makes things riskier. As one reader put it: “Great response to your letter writer with the GI problems this week, but you suggested that male and female condoms can be combined. This actually increases the risk of a breakage, so please tell your readers not to combine condoms!” I tossed that into the column quickly, as an aside, and I clearly should’ve double checked. My apologies. More—and better—info about the correct use of female condoms can be found here, here, here, and here.