So I was browsing on my NSFW Reddit account and there was a response to a dark fantasy question post that kinda piqued my interest. It basically was like "I want my wife to dress me convincingly as a woman and have a nice dinner and then do sexy stuff".

And it got me thinking: like I'm a very straight male. No questions about my sexuality whatsoever. But it would also be super interesting to see what I would look like as a woman. Like make me look as convincing as possible and then go out and see if I get any attention. Or maybe just see if a sundress on a hot summer day is as comfortable as it looks. On the other hand, I couldn't look in the mirror after my girlfriend curled my eyelashes, and I have a severe aversion to seeing myself in a lowcut top. So not 100% sure.

Advice? Also any questions welcome to help me get more clarity on this.

I cross dress for events (the goth community really doesn't give a damn) so have done it a few times. From a photo men have been convinced I am a woman, much to the amusement of their friends.

Dresses are very comfortable but takes a few goes as you will; feel very self-conscious. Best advice is to start with kilts, as I now have many as it gets addictive, but in hot summers they are fantastic.
Also, nothing stops a drunk guy's ideas of violence than a bouncer in a kilt. Confuses the heck out of them, then they realise how much shit I have to go through.

Remember you are safe at home so can do anything. If there is something specific you don't like then you don't have to do it. I don't like foundation as I touch my face too much.

TBH the whole idea of clothing being gendered is silly, and skirts and dresses can be entirely practical things to wear just as trousers and overalls are.

Traditionally Scottish highlanders wore a short leather dress under a kilt made of several yards of tartan woollen cloth, resulting in an outfit which was both warm, practical for sword fighting, and non-restrictive for farm working. The modern dress kilts you see in highland dress shops, and the utility kilts popular on the alternative scene, are in fact both variations on knee length skirts, rather than real traditional highland dress. But for some reason people who won't bat an eyelid at a man in a kilt will entirely freak out if the same man wears a dress. Which is bonkers, really.

I have several modern kilts and they are an absolute blessing at hot summer music festivals, way more practical than trousers in the baking heat of August on the North German plain. Way more men should wear skirts, even just very plain ones, in hot weather. Ventilation is bliss!

As to cross-dressing for WAM, personally I'd recommend it, especially when still young and slim. 30 years ago I used to have uniform skirts to wear in the bath. While it's now much easier to buy or commission scenes of women dressed in your own fantasy, there's still something nice about doing it for real, and finding out how it actually feels to get messy in the same kind of clothes you like to see women get messy in.

I shall weigh into this if you all don't mind. Since we are all being open and honest, I can comfortably say that I am the same: very straight male.. no questions at all...

HOWEVER.... I have a weakness for leather (pants, skirts and dresses) and satin (blouses, skirts, pants, dresses, gowns, etc).... and since, in my life, my mind is a VERY active place, I can say that the BEST way to combine my love of WAM and clothing I like, I is to partake in actually wearing the outfits myself.

Now... I have also been lucky enough to have found a few willing and able partners along the way who have been more than okay with this. They will wear the outfits too... but also, have invited me to wear their clothes and underwear.

Maybe it's just me... but for me, personally speaking, it's a whole other level. I have only done the wig and makeup when it's been Halloween or something... but I have done the full dress or jeans and blouse and underwear, etc.... and clothing has been TRASHED.

It boils down to what was also said on this forum... if you like it and enjoy it and it adds to the moment, go for it.

More details upon request

If you are comfortable in your body and your wife is cool with things, I say give it a go. Best way to find out is in the comfort of your own surroundings with a trusted partner. Who knows, she might like it as well. You never know until you try and life is far too short to sit around and wonder about it or have regrets for not trying it. Do anything once within reason. Know your limits and have fun!

While it is difficult to gather hard data on such things, from the information that has been acquired it has been found that most cross dressers are heterosexual. At least that is what I remember reading in the book "Perv" by Jesse Bering. And don't let the title throw you, that book was actually published by Scientific American and the author is a clinical psychologist. Great read if you are into such things

I am also a straight male but when it comes to wam I've been known to wear pantyhoes mostly for the feeling and because it keeps the mess nice and close to me. My wife doesn't mind. As for full drag it's not something I've wondered about however being a humiliation fan I would consider being dressed and messed.

I agree with Dungeon Master about the needless rigid norms around skirts / dresses etc. and what I consider a sort of thoughtless gender apartheid in the general culture.

I find wearing dresses very comfortable - it's usually the first thing I do after work to wind down when I get home. If you fancy trying it out, definitely do it to answer that question. I might be gay, but it's not at all a gay vs. straight thing. It runs across the spectrum. If you try it out and find it right, watch out: half my wardrobe is dresses now!

I have got away with wearing a sarong in social situations from time to time. I don't have a desire to present as female (e.g. no interest in makeup, wigs etc.) but I do like to challenge the boundaries, such as wearing female-cut jeans, t-shirts or cami-tops with male jackets or coats when out and about to see if anyone notices.

I also like to buy my dresses 'in person' - there are certain shops where I'm perfectly comfortable browsing and even talking to the assistants about the merits of a choice or other.

As for the messing - it certainly is glorious in skirts, dresses, stretch camis etc.

I actually saw a dude in a kilt and some sort of lace shirt at Busch Gardens (theme park) a couple months ago. Dude was a total badass and asked if he could buy me a drink.

It's funny you mention getting messy in the same clothes you like to see get messy because I've actually taken a shower in a maxi dress before and I think that's probably in the top 5 for the longest I've ever stayed hard.

I'm super camera shy but if I ever do what I've been toying around with doing, I would 100% end it with a fully clothed shower and depending how that goes I may take a gender into doing it again and posting a video or some pictures on here.

I did the kilt thing myself (many, many times)... but in all fairness it was an authentic schoolgirl kilt from a private school that my friend gave me. Gotta say.... pretty damn arousing. My friend got a kick out of it (she's very open minded) and then added to the moment by teasing "now... just think of the sexy black underwear I used to wear under that when I wore it..." (suddenly the thought of high school seniors either 18 or 19 years old, all wearing sexy black underwear under their kilts, sprung to mind)

I also tried the satin dresses (God bless Amazon) in the shower and baths, as well as leather pants, leather skirt, metallic jeans, satin pants - some collected from friends, others purchased - and I can co-sign on the notion that those times make the Top 10 List for longest time remaining aroused.

I'd agree with this, experiment and see what works for you - like WetNikki I've got an assortment of dresses (and a whole selection of other female clothing) in my wardrobe for whenever I feel like wearing something different, indeed I've been in a loose fitting ankle length dress ever since I got back from the shops this morning.

I also buy in person so I can get a feel for how it looks and the feel of the garment, but I realise that a lot of people aren't comfortable with this. Although my experience is that most shop staff really don't care what you're buying - I took advantage of the sales this morning to pick up a velvet midi dress and a pair of velvet trousers and the only question was "do you want the hangers"

Dressing up in women's clothing is fun. I've done it a few times and enjoyed it. Just go with your gut and see where it takes you.

Doesn't appeal to me at all I'm afraid. If I did it I would look like either Cissy or Ada (Les Dawson and Roy Barraclough) or Norman Evans

Google them if you don't know what I'm on about....

Being a crossdresser myself and going out as one I can say that the first steps are difficult. Getting friends to help you out is a great way. Female friends I have found in my own journey tend to be more open than men.

I agree with DungeonMasterOne. Gendered clothing in this day and age is silly. I mean leggings, high heels and skirts were all worn by men before women did.

Now some of the lovely people on here gave me advice that I took to heart and has made thing easier. Make up is what I struggle with as I often stim a lot, touching my face, scratching my head. Make up and wigs don't agree with me.

It's all about your personal choice when it comes to clothing. I like my high heels and leggings. You might skirts or dresses. Going out to fetish or Goth/Alternative events are a great place to experiment as, well again in my experience everyone is so overt that you are covert.

Okay unless you dress up in a dominatrix outfit and your 6 inch heels elevate your 183cm height to where you tower over everybody like a rubbery AT-ST with a flogger and rabbit ears. Again personal XP and very specfic.

However start nice and slow. If you want to share pictures for advice than UMD is one of the places to do it.

Sexuality wise I to am I straighter than arrow man who only likes females and is attracted to them. No, wait is that the same thing? No matter. Some will ask the big question if you plan on transitioning, it comes with the territory, again in my personal XP. NOthing beats that feeling though when you do see yourself fully transformed. It's almost like a brand new you, or a different version of you.

Slapping on a pair of heels and rubber leggings will give me confidence but seeing ones self fully decked out is special. For me it feels like wearing a suit of armour. Kind of uncomfortable (Pleaser heels can do that) but feeling protected.

Anyway that's enough from me. Good luck