Q I have been wearing bras and panties with stockings for so long now, it's become a part of me. I was wondering if you have heard of this before. —Sent From Samsung Mobile
A 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 chances 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 another point on the gender spectrum. 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 assume "dude."
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.
Q I'm a (mostly) straight male and I've been dating the same woman for more than a year. It's easily the best relationship I've been in. We get along great and rarely fight, and the sex has been great. But there were a few incidents recently when in the heat of the moment she asked me to tell her what I wanted to do and I froze. I didn't know what she expected me to say or do. These incidents ended in an argument. She views this as a sign that I'm not attracted to her or I don't have a strong libido. Both are untrue. I don't have strong preferences about sexual activities. If there is something specific she wants, all she needs to do is ask. But when she asks me to take control in the bedroom or to describe my fantasies to her, I either stare blankly at her or choose something at random, achingly unsure of whether or not I made the right choice. This has always been the way my brain works. When I masturbate, I just think about having sex, not about anything specific. If you could give me some ideas for how I can make myself less boring in the sack, I would love to hear it. — Mister Milquetoast Missionary
A You know that thing you sometimes do when your girlfriend asks in the heat of the moment what you wanna 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, ie, you can be a bit aggressive. If her signal is physical or non-verbal, 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.
Q I'm a mid-40s gay man in a LTR with a man I love very much. The problem is that, due to ongoing GI problems, I'm unable to bottom. At heart, I'm a total bottom, and the handful of times when I've been physically capable of bottoming (before my illness became so severe), I've loved it way more than any other sexual act. My husband is 50/50 versatile, and we have an open relationship, so he gets what he wants from me and from others. But sometimes it's frustrating for me to see him bottoming for another guy when I'm unable to. When a hot guy wants to fuck me, I have to decline every time. I just tell our fuck buds that I'm a total top, because it makes things easier. I'm glad that my husband is having great sex, but my health problems leave me sexually unfulfilled. I'm receiving treatment, but I'm still not ever "clean" enough to bottom confidently. —Sadly Unfilled Bottom
A Two practical tips: first, female condoms. I realize you're a dude, but they're a terrific option for buttfuckees worried about cleanliness. 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 partner will never know.
Second option: frottage. 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. You're not being penetrated, but your taint, the outside of your hole and your sack are all getting stimulated.