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Put On Your Red Wigs
Just got an advice request from a guy, and I'm in an airport hotel in Paris enroute to Mantua, Italy, and I'm not sure how much Internet access I'll have there. I had a few questions to ask him, which I e-mailed him, so I have yet to answer. But, hey, how about you have at it?

But first, do your homework. Read my column on crossdressing, Who Wears The Panties In The Family? Here's an excerpt from my answer:

There’s a U.S. senator who can’t speak publicly unless he’s wearing pantyhose. He was a patient of Dr. William Stayton, a psychologist and leading expert on cross-dressing. “Underneath his blue suit and tie he wore pantyhose and a bra and women’s underwear,” Stayton told me in a recent interview. “He was always worried somebody would lift his pant leg and see his pantyhose. But it was the only way he could calmly speak before the Senate.”

So, one man’s Prozac is another man’s pantyhose. So what? My boyfriend compared the senator’s cross-dressing to his own penchant for hats. “When I wear my Henschel High Roller I have a totally different outlook. You swagger a bit, you just know you’re cool. I take the hat off, and I’m just another guy.”

Here's the guy's question. (I'm especially interested in hearing how women would feel if they were in this woman's place):

I'm a middle-aged straight guy who has worn ladies, nylon panties for several years with the full knowledge and support of my late wife. We'd often buy matching pairs just for fun. Unfortunately, I lost her about 18 months ago and am just beginning to "date" again, though nothing serious and nothing intimate. However (the word which makes your career possible), a lady with whom I've been spending time seems to enjoy my company and I hers. While I'm a widower, she's divorced; we both have grown children and are in our 50's. My question is at what point do I reveal my prediliction for frilly underwear? I'm straight and, except for a minor dalliance fortified by alcohol and curiousity in college, have never been interested in, or engaged in, sex with a man. I don't dress in women's clothes, except for panties and an occasional matching camisole. I own no dresses, high heels, or bras. I just find your underpants more fun, comfortable, and interesting than whitey-tighteys, boxers, or men's briefs. A nice pastel bikini from Vanity Fair is just fine. I may be presumptious, but I sense our relationship is moving towards intimacy. Any suggestions on what she might find if we move to that level in our relationship? thanks for any help you might provide.

For panties big enough to hold a package, check out Here's one of the selections:


Posted by aalkon at September 6, 2007 1:44 PM


I am hypocritical on this one. I really liked how he wrote that he and his wife used to buy matching skivies and all. I think it is amazing, rare, and beautiful when two people can click so well. When I READ this letter, I think to myself, "if this woman really loves him, then she should accept blah, blah, blah." But, I am telling you, if some dude I liked brought this to me, I'd have the right poker (ha ha) face on; but, I would be out within a month...probably much less. But that's me. I like manly men. I like calloused hands and a little stubble. I go stark raving mad over deep voices and big muscles....and skills!!!! Anyway, if I were in his position, I would bring up a story about someone else in the same position and see how she responds. If she freaks out, he probably will find her less appealing anyway. For example, I love kids. I have a ton of my own and have just recently opened a teen center in my community. If I meet a dude and figure out he doesn't really like hanging out with kids much, then I am just not that interested in him anyway. People should choose right for themselves so that they can achieve the happiness they want.

Posted by: kg at September 6, 2007 6:51 AM

My deepest sympathies for your recent loss. It sounds like she was a very special woman. If you are ready to talk britches, let's talk.

To the extent that underwear choice has any bearing on how people relate to each other, it probably shouldn’t. Look at a group portrait of the supremely manly founding fathers of the United States, they were all wearing wigs, silk stockings and high heeled shoes. And if I was sitting around with the guys, watching the game and tossing back a few beers, I couldn’t work my underwear into the conversation without great and obvious effort.

But underwear does impact how people relate to each other. My kids get me a set of novelty boxers every year at Christmas and I always put them into circulation without a second thought. I had a doctor appointment a few weeks ago, in July, which I forgot about as I was dressing for the day. It came time for the old “turn your head and cough” or some such procedure and the Doc said something about reindeer and snowmen, oopsies. People notice things. They have expectations for how others will act and it makes them nervous when people stray too far from convention. When one gets into a situation where underwear choice becomes part of that equation, the stakes are higher. Now if I were an EMT, I am sure I would have seen it all by the second day and I would stop the bleeding and treat for shock just the same if my customer wore chain mail and a feather boa.

But here’s the deal: Physical intimacy should, in my little world, follow emotional intimacy. Getting naked for the first time is the wrong time to find out a major component of your special friend’s identity whether it be underwear choice, recurring medical condition or the fact that you are a fugitive from justice. This is the kind of thing a person either can deal with or they can’t. A good way to reveal something about yourself that another person might find shocking is to leave them an “out.” Let her process and digest the information without you hovering over her for a reaction. Don’t put her in the position where her ride home seems contingent on acceptance.

Your lady friend might be thrilled with this aspect of who you are and it might be something she can warm up to in time. And of course your underwear might be a deal breaker but so might your choice of investment fund or pizza topping. The principle doesn’t change; you have to be who you are. Good luck and remember to use the delicate cycle.

Posted by: martin at September 6, 2007 7:20 AM

The principle doesn’t change; you have to be who you are. Good luck and remember to use the delicate cycle.

martin, you are TOO funny! But what you said about being who you are is so true. And if I were in the position of this man's lady friend, I have absolutely NO idea how I'd react. I think maybe I'd be taken aback at first, and would need some time to think about it, but I'd have to take in all the other factors before I make a decision. In the end (pardon!) I like to think it wouldn't make a damn bit of difference, if everything else was right with the relationship.

Posted by: Flynne at September 6, 2007 7:58 AM

I know 3 women who have made comments indicating that that kind of thing would be a deal breaker. I haven't heard from any of my female friends that they wouldn't care, though the ones that don't care just may not have had reason for bringing it up.

Posted by: William at September 6, 2007 10:27 AM

I'd dump him.

Posted by: PurplePen at September 6, 2007 10:56 AM

I'm a female and I think it is kind of hot. I would have no problem if a guy I wsa dating told me he was a crossdresser.

Posted by: Elizabeth at September 6, 2007 10:56 AM

I think the husband and wife wearing matching underpants is the sweetest declaration of love and understanding I've read in a long time, Amy. It's way better than the sentiment (namely, avarice) behind those DeBeers' commercials cajoling men into blowing two paychecks on a diamond necklace.

As for me, I agree with Martin. I would want to know about this personal kink before it was time to get naked. Personally, I don't have a problem with a guy wanting or needing to wear ladies' underwear, but it's something I would like to be prepared for before the clothes came off.

Posted by: Rebecca at September 6, 2007 10:58 AM

If the guy was really good looking and had a nice body, AND had good taste in lingerie, it could be very hot. For me it would depend how heavily he was into it. I'd want him to be butch about 70 percent of the time and let me wear the lingerie. There are a lot of variables and if it was too much it might put me off.

Posted by: Chrissy at September 6, 2007 11:01 AM

I wouldn't find it to be an issue. I would tell the guy, however, that I reserve the right to critique (politely) his fashion sense as far as color, decorative flourishes, and the like.

Posted by: That Julia at September 6, 2007 11:02 AM

I'm not sure why it would be an issue but hey different people want different things. I had a friend who actually did this, and all was well. Then his mucho nasty girlfriend announced to the world. The results were not pretty, though he's still with her. I think the issue with men wearing panties are both a gender identity issue, and all of the stigma attached to it. Do all men who wear panties kill or are deviant? No. There are however multiple famous deviants (the former FBI director Hoover for example) who wore panties and thus a stigma is attached.

Martin is right he needs to let her know about it before they get naked. The first time getting intimate with someone for the first time (especially after a divorce) tends to be nerve racking all by itself. This kind of surprise would be really bad.

Posted by: anon at September 6, 2007 11:22 AM

:::earworm alert:::

"...girls will be boys and boys will be girls..."

Posted by: Flynne at September 6, 2007 11:29 AM

As much as I hate to admit it, my basic reaction was mild distaste. I don't find it at all appealing, probably because I, too, like my men fairly manly. When a man looks at me in my bra and panties, I want him to think, "God, she's hot", not, "Do those come in my size?" On the flip side, I find a great deal of other fetishes very appealing. Maybe this one's just not for me.

But, I agree with the others above. He should tell her before they are intimate. If it was something he'd like to do now and then but not neccessary to him, it could be brought up later. This sounds like it's an important part of his life/sexuality/expression, and not something negotiable, so it's got to be on the table before they progress into bed.

Posted by: Christina at September 6, 2007 12:20 PM

No wig required here. For me personally, this would probably be a deal breaker. Not that I think its wrong in any moralistic sense, I'm just attracted to more rugged men. Just as some men wouldn't be attracted to a woman who likes to wear boxer's or "granny panties".

That said, I'll try just about anything once, so perhaps if he was very masculine in every other way, I could get over it. And certainly if my guy wants to play dress up once in a while to add variety to our sex life, I'm all up to try whatever fantasy he has in mind!

But I'd definately recommend this conversation happen before they get naked.

Posted by: moreta at September 6, 2007 12:27 PM

Its a mixed up muddled up shook up world....except for LOLA. -- The Kinks

Posted by: moreta at September 6, 2007 12:31 PM

At first, this seemed like one of those gender asymmetrical situations. If a woman told me she had a surprise for me and then stepped into the room wearing old jeans, windbreaker and a ball cap, I'd say, “We' the garage?”

But then I think of Norah Vincent's "Self-Made Man." If I was dating a woman and she revealed to me that she sometimes liked to masquerade (convincingly) as a man, I would have some serious thinking to do. I would have to be quite secure in my hetero-masculinity to get past the fact that, at some level, I would be dating (and screwing) a man. Partly, it would trouble me to think that people who saw us together while she was in costume would think we were a gay couple. But mostly, it is the fact that gender is one of the foundational components of identity. I am the male and she is the female and any blurring of that line just sounds like a boxful of “issues” waiting to be unpacked in my bathroom and I ain’t havin’ it.

...not that there's anything wrong etc.

Posted by: martin at September 6, 2007 12:58 PM

I once grew friendly with a woman in a pleasant and gradual way. Some time after we had been getting “friendly” on a regular basis, she let me know she had a daughter. The circumstances under which she told me this made it pretty hard to express anything but enthusiastic acceptance lest I seem a cad. I grew genuinely fond of that little squirt and to this day I miss her more than her mother (who was probably more insecure than genuinely manipulative) It would have been nice to have known earlier in the game.

Posted by: martin at September 6, 2007 1:13 PM

> If I was dating a woman and she revealed to me that she sometimes liked to masquerade (convincingly) as a man, I would....

I would comfort myself with the thought that anal sex might well be on the menu at some point. As in the Gainsbourg/Birkin 60s movie Je t'aime... moi non plus, whose sole plot point was Birkin offering her utterly gorgeous ass to her bf. Clue: The role she played was a barmaid named Johnny.

Posted by: Stu "El Inglés" Harris at September 6, 2007 1:28 PM

Definitely something I would want to find out before I got naked with a guy. I might lift an eyebrow, but it wouldn't be a deal breaker. I would be a little weirded out if he liked to wear bras (double standard, slightly hypocritical I know) but I understand the underwear thing. I wouldn't want to wear tighty-whities either.

Honestly I've never thought guys in their underwear looked attractive, even underwear models look kind of . . . . . awkward.

Just my two cents.

Posted by: Elle at September 6, 2007 6:19 PM

Holy smokes, Amy! That's a fine looking pair of panties!

You women know just how to make men salivate, don't you!?

Yikes. It reminds me that I should maybe be a better man than I am, but I love what may be an inherent decadence to so clearly imagine (and even remember) how beautifully a beloved woman can wear them -- pink panties with the those frills are as sweet and peculiar as a dear woman's charms.

Posted by: curtis at September 6, 2007 9:39 PM

I know 3 women who have made comments indicating that that kind of thing would be a deal breaker.

Why, of course...farting through silk is a woman's prerogative!

Posted by: Doobie at September 6, 2007 10:29 PM

I would guess that most US senators would be unable to make a speech unless they were dressed in conventional clothing. How is that different from the one who must dress in unconventional clothing to speak? Is the important thing not the content of the speech, rather than what the speaker has to wear in order to feel confident to stand up in public?

Posted by: Norman at September 7, 2007 12:39 AM

Straight man checking in here (just to put things in context). I don't wear women's underwear. Women's underwear doesn't even do anything for me when women wear it. It's just a roadblock on the way to nekkidness for me.

That said, it doesn't seem like such a big deal to me, at least not in comparison to other kinks that this guy could have. Does he want to tie her up and whip her? No. Does he want to urinate on her? Not at all. If a minor reconfiguration of the cut of his underwear makes him happy, who cares?

As to when he should let his new love in on his little secret, I'm with Martin. He ought to clue her in before hitting the sack. Nobody likes surprises, at least that kind.

A while back, I met a woman, dated her for a while, slept with her. I was under the impression that she was divorced. I was under that impression because she led me to believe so. After we'd been seeing each other for a while, somehow I discovered that she was divorced, but it had happened a lot later than she led me to believe. Like six months after we got serious, and about two weeks before I found out. She was certainly separated from the guy, but they weren't divorced. I broke up with her the next day. Keeping information from people that necessary for them to make informed decisions in order to manipulate the outcome of the decision-making process is exactly the same as lying. Or pretty close, anyway.

Posted by: LMM at September 7, 2007 12:14 PM

LMM, deception, as you know, is one thing that doesn't make much good foundation for a new relationship when it's already established in the old, not that I know from your post she practised deception there & then.

Fine women are a treasure, bad ones aren't. Women can say the same things about men.

Posted by: Curtis at September 8, 2007 11:56 AM

::: Donning my curly red wig, breaking out into song ::: The sun'll come out...tomorrow...betcher bottom dollar that tomorrow...

Sorry, wrong wig.

::: Discarding curly red wig, then donning another :::

Sorry, still wrong wig.

::: Discarding second red wig, producing a third :::

Be sweet, don't gain 300 pounds, give blow jobs.

Got it!

I guess his only recourse is to spring this on her, and see how she responds. If she wants out, wish her well and move on. In the future, he might consider taking out a personal ad at eharmony or The forum lends itself to posting intimate details about a person without actually revealing your identity. For a fetishist, particularly his fetish, it's probably the best way.

How'd I do, Amy?

Posted by: Patrick at September 8, 2007 2:56 PM

E-harmony is homophobic! After recommending it just now, I went to look at it. It seems the only options they offer are for men seeking women or women seeking men. Hello? Not everyone's straight, you know! Seems to me that they're cutting out a sizable potential market.

Posted by: Patrick at September 8, 2007 3:01 PM

kg & Clarissa -

Callous hands; check, stubble; check, capable of building or fixing anything house related; check, capable of scooping up my pregnant partner when we want to get frisky - in spite of the fact that she now outweighs me; check. I don't know that I am a seething volcano of masculine prowess, but I am pretty manly. I am also perfectly comfortable wearing skirts and frilly blouses. I have had several partners who are jealous of me in a teddy, including the current one. I also came in second, three years in a row, on the Halloween cross-dressing contests, only because I refuse to shave, no matter what I am wearing.

I too had my experimental phase, found that men just don't do it for me. I am all about the feminine pertinent parts. I don't wear women's clothing all the time, or even that often. But there is nothing more comfortable than those light, floor length hippy skirts sans-underwear. And women's clothing is the epitome of great accessorizing. Ever since the first time, when I was basically homeless and a lesbian friend of mine put me in one of her skirts so she could wash my clothes, I have been hooked.

I'm not nearly a keen on the teddy's, but since discovering how much it turned on one of my partners, I thought, "what the hell." I have found that a lot of women really find it sexy and I'm pretty eager to please - small sacrifice really. And every so often, my partner likes to go to the lesbian bar, so I dress up sexy like and accompany her as the bearded lady with a rather pronounced adam's apple. It's really rather fun, as she likes to go kind of butch on those dates.

Fun fact for the day, though I can't find the reference online, most men who are into casual crossdressing (as apposed to those who do drag shows) are into women.

Posted by: DuWayne at September 9, 2007 2:08 PM

Patrick says:

E-harmony is homophobic! After recommending it just now, I went to look at it. It seems the only options they offer are for men seeking women or women seeking men. Hello? Not everyone's straight, you know! Seems to me that they're cutting out a sizable potential market.

I respond:

Eh, not really. I don't think that E-harmony having listings only for men seeking women or vice-versa adds up to them being homophobic. After all, there are plenty of specifically gay dating sites, along with those that cater to everyone, of every persuasion. And if it's OK to run a gay-specific dating site, it's just as OK to run a straight-specific site.

Posted by: LMM at September 10, 2007 7:46 AM

Curtis says:

LMM, deception, as you know, is one thing that doesn't make much good foundation for a new relationship when it's already established in the old, not that I know from your post she practised deception there & then.

I respond:

In her defense, I don't know (or have any reason to think) that she practised deception in her previous relationship. She was separated from the man before I met her. She just wasn't divorced, as she led me to believe, when she started seeing me. Some people have scruples about dating married people, no matter how troubled or terminal that marriage may be. They should be able to make an informed choice about whether or not to enter into such a relationship.

Posted by: LMM at September 10, 2007 7:50 AM

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