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Thursday, April 3, 2014

SL Letter of the Day: Resources and Support?

Posted by on Thu, Apr 3, 2014 at 2:28 PM

Hi Dan! I'm a 30-something bi woman who recently started seeing a straight guy who likes to wear women's clothes. He's never been open about this with a partner before and while I've been GGG and kink-positive for my whole adulthood, I don't have experience with this particular kink and I want to make him feel as supported (and hot) as possible when he's finally ready to roll it out. I'd love to do find some kink-positive resources but somewhat predictably, Google searches for "cross-dressing boyfriend" turn up a whole lot of OH MY GOD MY BOYFRIEND WEARS PANTIES, IS HE GAY???

What recommendations do you have? Thank you! And thank you for basically being the reason he had the courage to talk to me about this. It's going to be HOT AS HELL.

That's My Girl

My response after the jump....


The best possible resource for a straight guy who likes to wear women's clothes? A girlfriend who thinks the idea is HOT AS HELL. And your boyfriend already has that.

Your desire to show your support by digging up "resources" for your boyfriend is admirable, TMG. But it's just a kink—and a thoroughly harmless, completely run-of-the-mill kink at that. Your boyfriend doesn't have cancer, he didn't lose a parent, he's not addicted to crack. Does he really need a support group? Again: your boyfriend has a harmless kink with an extremely low barrier to entry and, unlike some harder-core kinks (mummification for instance), his kink requires no specialized skill set and presents no risk of bodily harm (unless you regard "ballsack falling out of panties" as "bodily harm"). Pushing resources at him—or encouraging him to attend a support group—may wind up making him feel unsupported, TMG, as he could feel pathologized and/or judged. And you don't want that, right?

So here's my recommendation: Roll his kink the fuck out already! Take him shopping. Buy him some panties and bras and skirts and heels and whatever else turns him on. Ask him to dress up for you—and then fuck the shit out of him.

Okay, okay: here's one resource for you and your boyfriend. Enjoy!


Comments (17) RSS

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Eva Hopkins 1
Maybe she was hoping for exactly the one resource you provided, Dan - some shopping help. :) I know finding shoes in men's sizes can also be hard. I've never had to buy lacy unmentionables for a fellow before. That site home page.. *fans self*

What a fun, friendly letter. She sounds like she can't wait to rip his stockings off.

Posted by Eva Hopkins on April 3, 2014 at 2:39 PM · Report this
rinohog 2
And start a blog so the next person who searches that will get have a good resource to share.
Posted by rinohog on April 3, 2014 at 2:51 PM · Report this
I learned about "dancers' belts" at comic con last weekend -- they're worn to keep the male genitalia in place and reduce panty lines under tight fitting clothing. Lot of cosplay guys apparently wear them (who knew?). Sounds like a useful for cross dressing guys. Panty lines are a bitch.
Posted by wxPDX on April 3, 2014 at 4:41 PM · Report this
agreed--shoes are the hardest part of it. plenty of large sized women's clothing around, cause...plenty of large ladies. but gaining weight doesn't make your feet much bigger--maybe 1 size, no more.
Posted by ellarosa on April 3, 2014 at 5:09 PM · Report this
Good for her and score for this guy in finding a fun ggg girlfriend! Panties really highlight a hard-on, enjoy!
Posted by jujubee80 on April 3, 2014 at 5:18 PM · Report this
kitschnsync 6
wxPDX @3, I've never cosplayed, so I'm not sure if "dancer's belt" is a unique garment or what... But I have taken ballet, and dance belts are worn by male dancers to keep their junk up front (and therefore out of the way for dancing). As a side effect, they make one's package present proudly.

So for crossdressing guys who are trying to minimize their package, it would have the opposite effect. Cosplayers wearing skintight outfits probably like them because it makes their junk look like Baryshnikov's.
Posted by kitschnsync on April 3, 2014 at 6:48 PM · Report this
Several years ago the BF and I did a stint of panties and heels play. The hottest part was the hard dick sticking out of a pair of very tiny and lacy panties. Ooof.
Posted by Tor on April 3, 2014 at 7:05 PM · Report this
Hi Dan et al - I'm the OP and I didn't mean resources for HIM, I meant resources for ME. Ideas! Blogs! Good erotica! Sorry, I guess I should been more specific. :)
Posted by crumbling.walls on April 3, 2014 at 10:23 PM · Report this
@8: As a guy who likes to wear girly clothes, what I can tell you is that a lot of crossdressers are turned on by gender play in general. Beyond just the clothing, a lot of us tend to find the mental image of ourselves as females very sexy. You'll want to talk to him about this, of course, but he'd probably be interested in things like pegging and other role-reversal type play.

You could also ask questions over at
(I actually posted a link to this page there, earlier.)

Good luck, you sound awesome, and he's very lucky to have you!
Posted by Zeusifer on April 3, 2014 at 11:01 PM · Report this
Along with what #9 says, also keep in mind that a lot of the sexual thrill of cross-dressing is in the process of dressing itself, not just what comes afterwards. Do it slowly.
Posted by Dr. Gnu on April 4, 2014 at 5:01 AM · Report this
AFinch 11
@8 you sound like an awesome GF.
Posted by AFinch on April 4, 2014 at 5:59 AM · Report this
bookmarking that link for later reference. My relatively vanilla spouse would likely not indulge me, but I'm OK with fantasy!
Posted by ariane on April 4, 2014 at 6:03 AM · Report this
Glad OP chimed in-- I was reading Dan's response going, "Umm... I think you misunderstood the question... and now you're being a little judgey... this is awkward"
Posted by chotis on April 4, 2014 at 7:57 AM · Report this
Fistique 14
I found the book The Lazy Crossdresser (if it's still in print/available) to have a lot of good general rules for femming up on the cheap.
Posted by Fistique on April 4, 2014 at 11:30 AM · Report this
Corylea 15
I used to have a cross-dressing boyfriend. This guy was definitely not trying to pass for female, since he had a full, bushy beard and male pattern baldness (which I thought made it all the hotter when he wore women's clothes, since he was so clearly NOT a woman, which made it all the more transgressive.)

One day when it was his birthday, I'd put up balloons as part of his birthday celebration. As a joke, I blew up two and stuffed them down the front of his shirt. Well. He loved them. No, he LOVED them. He wore them for the rest of the day and seemed quite regretful when taking them off that night.

So a little gender play beyond just clothing might not be amiss. ;-)
Posted by Corylea on April 4, 2014 at 1:00 PM · Report this
@8,13 Yeah, I read it the way the letter-writer intended. It seemed very similar to the supportive partner who wrote in with a foot-fetishist partner asking for advice about how to incorporate that, simply because the LW hadn't done it before and wanted ideas and info. Tons of people read tips about sex, not because they think they need a support group, but just because it's good to learn what sorts of things people tend to like to have more ideas to try. I'm glad the LW clarified. You seem like a good partner, LW.
Posted by uncreative on April 4, 2014 at 4:06 PM · Report this
I have ordered from, the site used as the "resource." They make really cute stuff, and it fits very well, it allows room and fits men, while remaining very feminine. Their shipping and customer service is great too. I highly recommend ordering through them. They actually make items for men, instead of just selling women's items as a lot of places do.
Posted by Paulinator85 on April 21, 2014 at 12:08 PM · Report this

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