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Crossdresser Fashions
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Crossdresser Fashions
Cross dressing is more than a guilty pleasure for a few homosexual men; it’s a form of emotional and psychological relief, a lot of fun and a great community, and a huge turn on! If you’re interested in crossdresser fashions and you’re thinking of giving it a go but don’t know where to start, I’ll give you a quick introduction into what to try first. Crossdresser fashions aren’t just buying a wig, a mini skirt and some high heels. Looking and appearing like a woman is hard and takes time and practice and most importantly attention to detail. If you’re worried about being discreet, don’t fret about that either, there are more online stores than you think (most of which send their items in unmarked packages) and a huge gay and straight crossdresser fashions community online.
First Timers

The most important thing is to always start small. No man is going to put on a little black dress and automatically blend into a crowd of women – it’s just not that easy. Start with something you feel very comfortable with when you’re just starting out or you think you might be interested in crossdresser fashions. As I mentioned before, my boyfriend was the one who got me started on all this because he was already interested in it, and he made sure to take small steps with me. Instead of presenting me with a dress and some stockings, Harry came to find me at my desk at work and pushed a pair of women’s panties across the desk towards me.
After a second, he grinned and told me that if I changed into them in the men’s toilets, he’d give me a reward at the end of the day for wearing them for the rest of the afternoon. I’ve always been a bit of a pushover, and I’ll do most things for Harry if he asks nicely enough, so I went and changed and that was my first step towards the world of crossdresser fashions. If your first time goes well, and without any embarrassing discoveries, you’ll feel more comfortable about trying again later. I barely got any work done that afternoon because I was so turned on that I had to either go and jerk off in the toilets or be unable to concentrate, but I realized that Harry had unearthed a kink that I didn’t know that I had. It felt really arousing to be wearing women’s underwear in front of people in the office that I knew and worked with every day, and even better every time Harry found an excuse to walk by my desk and looked me up and down.
Crossdresser fashions might appeal to you for different reasons, but take whichever item of clothing you think will feel sexiest to wear and try it out. Subtle items of crossdresser fashions clothing are best because you can experience the feeling of wearing them in public without worrying anyone will notice and you might feel stupid. Now, it’s pretty likely that you’ve already tried this and want to go a step further, so I’ll tell you a bit more about crossdresser fashions.
Crossdresser Fashions For The Fun Of It
There are plenty of guys who want to cross dress because they like the clothes and the feel of wearing them. There’s no need to have people confusing you with your sister just because you like to throw on a skirt every now and then, it can just be a bit of fun! If you’re more into the thrilling, sexy side of it than passing for an actual woman, there are lots of crossdresser fashions for you. In my experience, most gay clubs welcome any guy in crossdresser fashions, even if you haven’t taken the time to shave your legs or paint your toenails for the full effect.
I’ve never been into a normal club or bar dressed as a women unless I thought that I looked very convincing, because I don’t know what their reaction would be if they knew that I was a man. Be careful and sensible about where you choose to go and make sure that you’re not alone and that the people in there won’t have a problem with your outfit.
Looking And Acting Like A Woman
If you want people to look at you and assume you’re really a woman, you have to choose clothes from crossdresser fashions that hide the parts of you that are obviously masculine. I’m pretty lucky because I have a slender figure, but all guys have wider shoulders, thinner hips and shorter legs than women. You can’t change this, but by wearing crossdresser fashions that don’t draw attention to these parts of you, it’s easier to at least make them less obvious. Here are things that you can hide:
• Upper arms: Guys usually have much broader biceps than girls, and if you start out wearing something the covers them, you might look the part a bit more

• Knees: Another thing that aren’t quite as dainty as a woman’s and can easily be covered up with a skirt.
The first time I went out dressed as a woman, I ended up wearing stuff that covered as much as me as possible. OK, I didn’t look very sexy, but it worked and that made all the difference. This leads me on to the number one mistake that men make when they’re wearing crossdresser fashion: They dress up like a whore.
Alright, I’ll admit that a lot of women when they go out at night are wearing skirts that are so high you can see their ovaries when they bend over, and you can’t look around a restaurant without seeing at least one woman in a tiny LBD. But all the same, this isn’t how women dress all the time. Never start wearing crossdresser fashions by wearing the tiniest, sexiest outfit you can find because it will be obvious that you’re a guy in a dress. If you want to have a bit of fun, then wear whatever you want! But to pass for a real woman, your crossdresser fashions should be a bit more subtle. On the plus side, something more flattering and restrained might cover a few of your more masculine bits too.
For Harry’s last birthday, I took him to a restaurant dressed up as a woman. I was wearing a light blue summer dress that finished below my knees and covered my shoulders, and panties that made sure everything down there wasn’t making a visible bulge. Obviously Harry loved it, but more importantly I got a few appreciative looks from other guys when we walked into the restaurant. Crossdresser fashions are tricky unless you’ve got the right sort of frame, but I’d always advise someone who was interested in cross dressing to try on a range of outfits and see which suit them best.
Finishing Touches of Crossdresser Fashions
This might seem obvious, but the little touches are the ones that make the difference when it comes to crossdresser fashions. I can only tell you what works for me, but I’d say I’m a pretty successful crossdresser.
1. Behavior
Men and women just don’t have the same body language – they have different postures, different gestures and different sitting positions. When I’m dressed as a woman for Harry (even when we’re alone), I change my body language completely. I look up at him instead of lifting my head to meet his eyes and I stand up straight instead of slouching like guys do normally. Crossdresser fashions and being a woman means that you have to think about all your body language habits. You can’t sit down with your legs wide open, and you have to be more aware of the space around you. Take a look at a straight couple together and you’ll see the difference in body language. The woman usually has much more graceful gestures – it’s a bit like comparing a cat and a dog.
2. Shaving
Maybe you don’t want to take this step because the boys at work might notice if you’ve shaved your legs. All the same, I always feel much sexier if I’ve got hardly any hair on my body. Everything’s smooth and bare, and it makes me feel more feminine. After I first wore women’s underwear, my next crossdresser fashions step was to shave my legs and my pubic area. I did it for myself more than I did for my boyfriend, and it felt amazing. Some guys feel like it emasculates them a little to have all their body hair shaved off, and that’s the turn on for me. At the very least – it makes your dick look much bigger!

3. Make-up
Make-up’s always kind of hard to get right, but my advice would be that you can never wear too much mascara. It’s only with eye-shadow and lipstick that guys get too carried away, but that might be the look that you’re going for. If you’ve got a feminine face anyway, just take a look through a women’s magazine and find a picture of someone you think you look a bit like and copy their makeup. Otherwise, try asking a professional to have a go at it. Obviously you’re not going to be able to afford to use them every day you want to go out wearing crossdresser fashions, but they can give you some tips and tell you what suits you and what they used.
Men’s Lingerie and Crossdresser Fashions
There are plenty of people who want to stay discreet about their fetish for crossdresser fashions, and just stick to lingerie. There’s nothing wrong with sticking to lingerie made strictly for women, but if you’re going through an ex or current girlfriends lingerie (or even your sisters, who am I to judge?) you’re eventually going to get bored of it or run out. To avoid walking round women’s lingerie stores, I’d recommend buying it online. The only problem with that is that the sizes are going to be all wrong, and things like corsets won’t fit because they’re designed with a woman’s body in mind.
If you want something that’s still feminine but guaranteed to fit, try searching for men’s lingerie and crossdresser fashions lingerie online. My favorite piece of lingerie is a lacy pair of panties that are delicate and pink enough to be a girls, but have a hole at the front for my erection to poke out through and a ribbon to tie around it. I bought them from a men’s crossdresser fashions site so that they fit perfectly but still look feminine. Corsets bought from men’s lingerie sites make an exception for a guys broad shoulders and wider rib cage, and some don’t have the hourglass bulge at the front where a woman’s breasts would be.
Obviously all sizes will be for men, and because the site owners understand that it might be your first time delving into crossdresser fashions, they make it as simple as possible, usually giving chest, hips and waist in inches and giving advice on whether to estimate smaller or larger for which items. Corsets for example are usually bought with a chest measurement that’s a couple of inches smaller than you would normally buy because it’s supposed to be so tight.
Crossdresser Fashions In Men’s Swimwear
This is a particular favorite area of crossdresser fashions for me, because Harry’s house has a pool and a backyard so I can wear anything without worrying what the neighbors are going to think. I’ve got to admit, I’ve never worn crossdresser fashions swimwear out on public beaches because I’m a bit too shy to. Actually, more importantly I haven’t because the idea of people watching me in a woman’s bikini would make me too hard for people not to notice!
I buy most of my crossdresser fashions swimwear from Koala Swim, which is a US run erotic swimwear site that has some of the most unique and daring designs I’ve ever seen. Koala Swim have a ‘Pussy Boy’ swim suit, so called because it has a sort of flat cup to put over your dick and balls. You can tighten the side straps as much as you like, and it flattens your package so that there’s no bulge there and it looks almost as if you’re a woman because it’s so flat. Apparently the Pussy Boy style of crossdresser fashions sells to gay and straight guys, and personally I find that wearing it really makes me feel like a woman. There’s an alternative in a flesh colored fabric called the Sexy Bitch which I prefer the general shape of, and the fact that from a distance it could almost look like I’m a girl, with the way that it hides my cock.
Another great idea is the Mangina Bikini, which sounds odd, but is actually an ingenious example of crossdresser fashions. Instead of squashing everything flat, it has two separate pouches that are perfect for putting your cock and balls into so that it looks like lips of a pussy. The designer said that he had women commenting that it looked exactly like when a girl gets camel toe, and I can see why with the intimate design. I haven’t actually tried this one yet, but it’s on my list!
Essentially, if you think that you might be into crossdresser fashions, trying on some of this beach wear might be a good idea, even if you just wear it for you and keep it on under your clothes. The ‘Sweet Spot’ bikini finds a way of flattening everything so that you look and feel as close to being a woman as you can without actually having surgery. It’s a great way to ‘get the feel’ of being a woman without going too far or revealing a side of you that you might like to keep private to the rest of the world.
The Motivation for Cross Dressing
I happen to be gay, but I find it really irritating when people assume that men who are into crossdresser fashions are automatically homosexual. I have a male friend who’s happily married and likes to occasionally dress up in women’s clothing – he’s actually very convincing! But he only goes to gay clubs because he’s concerned about the response he might get if he wore crossdresser fashions in a straight bar. He certainly wouldn’t ever tell any of his friends about it, and even though his wife is happy with it and occasionally likes to come out with him when he’s dressed up, she doesn’t tell any of her friends either.
It seems really unfair that while women are allowed to wear all types of men’s clothes and they’re not always accused of being lesbians, that men aren’t allowed to try on women’s clothes without immediately being labeled with a sexual preference. People get involved with crossdresser fashions for lots of different reasons.
Personally, I like it mainly because it’s a sexual fetish I share with my boyfriend, and I usually only do it for his or my own benefit. It’s fun and exciting to have other men looking at me, jealous of my boyfriend because they think that I’m a girl. I also like the way that when I’m wearing crossdresser fashions and I feel like a woman, I find it much easier to be submissive and to let Harry be dominant over me. It turns me on to feel emasculated and to give control to him – recently I’ve started wearing some of the chastity devices that Koala Swim also make and giving the key to him. That way it feels like the old days, when a woman couldn’t get any sexual relief without her husband’s say so.
However, there are plenty of men who just want to get in touch with their feminine side, and to behave in a way that they can’t otherwise and crossdresser fashions are the easiest way for them to do that. Men feel like they have to act a certain way when they’re in their own clothes and cross dressing can be a relief for them. My straight friend told me that he first became interested in crossdresser fashions because he was jealous of the range of clothes that women get to choose from – he was fed up just choosing a shirt and pants when women had so many variations. He started out by buying clothes for his wife, almost as if he was dressing her up like a doll because he couldn’t wear them himself, and eventually he started buying things that he could fit into and trying them on himself.
He found that the draw about crossdresser fashions was that for a while he could be graceful and care about his image, and he liked to be able to wear the beautiful dresses that were formerly only available to his wife. Unlike a lot of men who wear crossdresser fashions, he doesn’t go any further than wearing the clothes – he doesn’t shave his legs for example, or wear women’s clothing when he goes to work. Apparently when he wears women’s clothes around his house, he just feels happier and more at peace, and he allows himself to be more sensitive and more graceful.
Many men find that they need crossdresser fashions to relax and take a little of the pressure from their shoulders, and to get in touch with their more feminine side. Others, like me, like crossdresser fashions to have a little fun and because they have a fetish for it. Some guys wear women’s clothes because they enjoy the huge cross dresser scene in gay clubs and they like to make a statement about themselves and their sexual preferences. And finally, some men like the feeling of appearing like a real woman in everyday life, and do everything they can – even eventually cosmetic surgery – to appear like a woman.
Crossdresser fashions can mean different things to different men. It’s a freeing experience to slip into women’s clothing every now and then though, so I urge you to give it a try!