Cross Dressing: Men Who Wear Female Underwear

You have a fuck buddy. You can drop in to see him with little or no notice and the sex is always fun and uninhibited. He is enjoyable company, doesn’t make any demands on you and you think you know him fairly well.

Then one day he asks about how you would feel if he wore female underwear and stockings during a future sex meeting. You keep looking at him, take a deep breath or two and stammer out the words about having no problems with that.

On the way home you’re saying to yourself that you thought you knew your buddy but perhaps not. You remind yourself that really you are still straight and that a woman’s body and her underwear still excites you. The fact that it’s now worn by a man shouldn’t make it any different, should it?

It’s a new image that you now can’t get out of your head. In fact it gives you a hard-on just thinking about it. You imagine the texture of the satin and lace panties, seeing the black stockings on his legs all the way to the groin, and then there is his beautiful arse just waiting to be filled by your pulsing erection. There’s a fusion of masculine and feminine, of straight and gay, of lust like you haven’t felt for a long time - and a sexual moment you’ve not encountered before. 

There’s no mention of other aspects of femininity like lipstick or powder so he’s not trying to be anything other than a man with a couple of pieces of feminine apparel on him. Except for the brief clothing he’s still the macho guy you like to fuck.

But there’s that odd feeling that something is not right. The scene is no longer black and white, well defined, man-to-man, totally masculine. There’s something else in the way. Could that be your own perception of what you define as ‘proper’ man-to-man sex? 

Cross dressing to some degree is widespread across many cultures. What is not so well accepted is the number of straight/bi men who like to wear female underwear. You only have to look on the dating sites to see photos of men – mostly very masculine men – who happily show a profile photo of themselves in silky female underwear. It’s not uncommon for wives, especially mature age ones, to know of the situation and to purchase the underwear for their husbands.

What is generally not acceptable is to see such men getting changed in public change-rooms or indeed, at the local gay sauna/bathhouse. Tolerance by the majority of men is still low towards such behaviour. Somehow it’s an affront to their masculinity to see another man not totally in the accepted image of masculinity.

Is it seen as an obtrusive reminder from the straight world about you having crossed the line into male/male sex?  Is it something you’d like to do yourself but accepting your feminine side is too difficult to bring in to reality?  Is it the guilt of touching the alluring satin feel of the underwear that says this should really be my wife, and not some man dressed up in female panties?

If you can accept his wearing of female underwear then chances are you’ll have really hot sex as your head will combine the best of both male and female erotic excitement. If you can’t accept the feminine intrusion into your male love-making chances are your cock will wilt and you’ll quickly move on to finding another man, quite possibly far more masculine than you have had to date.

Albeit you’ll be a wiser man about your own sexuality and what constitutes the best sexual partner for you. Perhaps you’ll also be more deeply appreciative and tolerant of the diversity that exists in human sexuality.

Disclaimer: All advice and information given here on this blog is general in nature and non-specific to any individual, couple or group. You are encouraged to seek your own independent professional medical, psychological and counselling advice. 

For more details about other man-to-man sex issues read

THE VERSATILE HUSBAND by Peter Benn

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"A straightforward, practical guide for men in heterosexual relationships who'd like to explore sex with other men.  Frank, honest and understanding."

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CRUISE EXCURSIONS: 25 of the Best European Cruise Ship and Baltic Cruise Ship Shore Trips by Peter Benn      e-book or paperback

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Straight Acting – A Jekyll And Hyde Approach To Man Sex

I read the guy’s profile on the hook-up site and it says “straight acting”.

My immediate natural reaction is that he is conservative in attitude, sexually closeted, married, only available during the day, doesn’t want to be seen by society as a deviant or different in any way – but in spite of this it has been my fortunate experience that probably he is also rampant in bed and whilst even a little bit horny, is totally insatiable. He either enjoys the full-on let-me-give-it-to-you-now alpha male approach or alternatively becomes the complete legs-wide-apart-fuck-me-deep-and-hard slut.

It’s as if he has to make this “I’m straight” statement to the world so that he can hide his real sexuality behind it.

Is it a way of reassuring himself that by acting ‘normally’ as a full-blooded heterosexual man he can slip through the socially acceptable net and sexually play with men without anyone noticing?

Or is it a reaction to the stereotypical gay man image that has unfortunately been portrayed for too many years by the mass media – that is, a limp-wristed, hand flapping, flamboyant, attention seeking, cross-dressing man?   Wrong that those images are, it’s an image he can’t – and doesn’t want to - relate to.

Is it about protecting himself by deluding himself?  Irrespective of what he does sexually he still sees himself as a heterosexual married husband and family man. By shielding himself with a self-image of respectability he can ignore his man-to-man sexual side as nothing more than a hobby, a fun game to indulge in whenever the time is right.

I suggest that it can also be a statement letting others know that he is not comfortable with the tag of gay or bisexual. It’s not in his head that their perceived lifestyle is what he is all about. Sure, he knows and enjoys sucking cock, taking it up the backside, shaving his balls and kissing anonymous men, but there is a resistance to accepting that what he does with his cock equates to anything other than a bit of fun on the side to his every day married life.

In his eyes straight equates to acceptable society expectations. If a man feels the need to identify with that so be it. For gay men looking for an exciting hook-up don’t underestimate the guy who identifies as ‘straight’ – more likely than not it’s a Jekyll and Hyde scenario. Irrespective of that defining statement in his profile he’ll take full advantage of his man-to-man sex time by making it the best and most enthusiastic couple of hours of his week. I love such a man in my bed!