Buying Lingerie. A sissy man's guide.

I may look fabulous, but
I feel sweaty and uncomfortable.

I don't know if you've ever bought lingerie or other items of women clothing with the intention of wearing it. I have. Lots of it. And here's some of my experiences and thoughts about it.

Buy with your touch, not your eyes.

What on earth possessed me?

Oh boy, did I learn this the hard way. See Ancilla Antila above?. Doesn't she look fabulous.?Wouldn't you like to wear her super-fetish outfit?

STOP! Put down that mouse! Click no further! It won't fit you. No matter what shape you are. It barely fits her and she has the body of a  Disney Porn Princess  Plus, it will feel horrible on your skin.  Poor Ancilla is probably putting a brave face on it for the photo shoot. She's preternaturally curvy and slim and it's probably still cutting of her circulation.

See this black strappy outfit ? I own that. What was I thinking? For a start, even though it does fit - just. It feels horrible. The stitching digs in, it doesn't really stretch, and the straps are very uncomfortable. I think I wore it once and gave up. Plus it's not that shiny, it was probably buffed up once the model put it on, and perhaps a bit of photoshop too.

Just in case it's not obvious, buying this outfit is not going to make you look like this woman. Well, duh. But it won't even make you feel like this woman either. You'll feel like someone who wasted $32 on something they'll never wear. 

Now, don't give up just yet. I'm not here to tell you to give up on your desire for sexy women's clothes. No no no. As if! But I do want to save you some dollars and some disappointment, even heartbreak.

See this dress. Bought from Amazon $45. It looks so pretty and on this model, looks lovely, but the fabric is unpleasant. It's neither sexily shiny or cotton comfortable, but feels itchy and heavy while looking like something your Grandmother would wear. I put it on. Once. Now it's in the never-wear section. I think that this is another case of the photoshop effect. I was so disappointing in this fabric. It's much more matte in real life than it looks in the photo. And, it just doesn't hang like that. Is she maybe wearing some kind of petticoat below? It's not just her hips making it flare out like that. In reality, it hangs limply.

As any woman will tell you, it is hard to buy clothes online. As a feminine-clothing obsessed sissy man, your problems are magnified. It won't feel like it looks, and even if you get your 'size' that's no guarantee it will fit. You don't have hips or boobs. It will hang loosely or else constrict painfully in all the wrong places.

If I move even an inch, this will
roll down to my waist.

Now, see this below. I have no recollection what made me buy this, but it's my favorite piece ever. The material feels sexy, clingy, soft but firm, and so very sexy. I now own six of these. But wait. Yes, that's the dress I bought first, but and yes, it was a revelation. But it had a major problem. Without a bust, it just won't stay up. The barest movement and it's rolling down your chest. Give it ten minutes and you're wearing a waistband. Nightmare. So, for my next purchase I bought the exact same dress, but with straps. Lovely thin spaghetti straps in the same material.  That's it below in the pink. Oh, how I wish I had bought six of them then, because shortly afterwards, these were discontinued. Now, I can't even find a picture of the strappy version in black to show you. The material is soft. It wears out. The one I have with straps still feels great but it has holes along the seams and this makes me feel a bit cheap when I'm putting it on. It spoils the experience. How I wish I had more of them.

So this advice may be pointless. You can't tell what it's going to feel like by looking online. You really can't tell if it's going to fit. Short answer, be cautious. If it looks fetishy and cheap, avoid. If the fabric looks less than perfect, then check what the hell it's made from and see if it matches other things you know you like. You want things that are stretchy and as simply made as possible.

I'm clever, because I have straps.

Now, an aside, and maybe I should have started with this. What the hell are you buying this for? I'm aware that not all motivations are the same. On one end of the scale are full-on crossdressers who go out in public. Good luck. I admire your bravery. That's not me. I'm never going to ever, ever let anyone see me dressed. Nope. I don't even look at myself in the mirror when I do. I know I'll look silly, but even if I didn't, that's not the point. It's the feeling that matters.The feeling of pulling the clothes on. The feel of them. The tug of the straps. The sensation of the soft fabric. The clingy firmness of lycra, comforting and holding. It's as specific and as personal as anything can be. I love to be dressed when I'm writing. Sometimes I just want to sit and feel the clothes. If possible, I move about, do housework, ordinary things. Just to feel how it feels. That's probably not you. Maybe you do it for the look, for wearing to work. For going for a drive. Who knows. Your mileage may not just vary but but be utterly different. This is me.

Are you going to be able to put it on?

See this? Oh god, how I agonised over this. It was so expensive and so lovely. I wanted it. So bad. I wondered if it would fit? How it would feel? Would I be able to breathe? 

These problems paled though, when I found I couldn't even put it on. Not that it didn't fit, but doing up those laces? You need someone else to do that. Yes, you can manage on your own, given an hour to spare, a pair of full-length mirrors, and a lot of patience. A great deal of patience. And then it still isn't right. And you can't sit down. Looks lovely though.

A team of five maids worked overtime
to strap me up. It was easy!

Stockings and their garters. 

I've written elsewhere about Pantyhose, and more on them later, but  yes, I do own some stockings. If you're going to buy corsets or the I-don't-know-what-to-call-it vinyl basque thing above then you need stockings to wear with them. I own some opaque pink stockings and a pair of vinyl-covered black stockings. But oh Sweet Fairy Godmother of all that's Sweet and Pretty, attaching the damn garters is a nightmare. You know the kind of thing, a little metal loop over a nub of rubberized metal? 

Try it out. Pops on and off. Easy. Lovely. Put some fabric - even gossamer thin nylon - between them, and it turns into a Chinese puzzle. Now, do it behind your back, over your upper thigh where you can't see and can barely reach?  How about a 60 denier stocking top? How about some faux-vinyl shiny black fabric over a nylon backing?  Aaaaagh! Hours I've spent wriggling and turning and cursing trying to get them attached on. They feel like they've gripped and then it just pops off, like they're laughing at you. Or worse, you get it attached on but you realise it's way off the position on the stocking top so the whole thing is twisted around. Ruing the effect. Remember what I said about why I'm doing this? For the luxurious, feminine feel of putting it on. You can see how it's hard to keep that in mind while you twist around painfully, cursing the damn things to hell.

So, forget that. Don't put the garter on. Put the stockings  and garter together first and then step into it. Yes, it's tricky. Yes you may need to do this from a sitting position or else you'll trip, bang your head then have to explain what you were doing to the paramedics, but at least it's possible. Now, never undo them again. Perhaps sew them together. That's it.

Yes it fits, yes I can get it on. But now what?

Pretty, perfect, and leaves no room
for an unsightlym uncomfortable bulge.

Another aside. I'm not going out or wandering around town in these clothes. This is strictly for alone-time, no chance of being disturbed time. What do I do when I have it on? Well, you can probably guess, but apart from that, writing. So, I'm sitting at a desk, typing. I want to feel feminine. I want to feel comfortable. I want to feel like I look pretty, and as long as I don't actually look, the fantasy works. But look at this thing - the pretty pink body. O own this exact one. Lord, it's gorgeous. The material is soft and silky. Mmmm. And yes, it fits too, just about. It's snug. And after a couple of minutes, that's a problem. It's so snug, so tight, so that what was a pleasant embrace is now getting distinctly uncomfortable. Yes, you can undo the poppers, but where's the point in that? Now, revived of all tension it just hangs there, feeling wrong, you might as well have got a pink vest.

No room for junk.

How about this one? Oh man, does it feel good, walking around or under a nice slim-fitting dress. Sit down though, get a little more, well, turgid, and suddenly you can barely breathe. Suffering succotash, it's as hard ot get off as it was to get on. Whew. 

So, you need to consider, what you're going to be doing in your lovely lingerie too. Are you likely to be, well, excited? In that case, perhaps consider something a little looser in the groin area,  or at least do yourself a favor and get something that can expand.

Dresses.

Flirt, fabulous and unavailable.

I've never bought a skirt. Only dresses. Skirts, well, they're just half as pretty as a dress, right? Here's one of my favorites. I actually have this in white, but it's this exact one. The skirt is so short! The nylon panel is so yummy! The waist is so high! Mmm Mmm. This is one of maybe half a dozen dresses I've bought over the years and this one is the only one that gets regular wear. I wish I had the black. I wish it was just a teeny weeny bit larger, but it's prefect and I love it. If only Yandy still sold it.

It's very, very hard to say why I like some dresses and not others. I love the feel of them. The weight hanging off your shoulders and hips. The swish of the hem, the folds of the fabric. But some I've bought, while they tick all those boxes just don't do it for me. Some combination of fabric, style and fit works and everything else feels wrong or at best, so-so. You  may have to kiss a lot of frogs to find your princess, but it's nothing to the number of dresses you need to try on before you find the  dress. 

Bodycon and shaper wear.

Like two mixing bowls
strapped to your chest.

Here be dragons - and fairies. If you think this article is just saying that buying women's clothes online is a hit-and-miss crap-shoot, then this isn't going to change that theme. I've bought lots of shaper wear too and I've been both delighted and disappointed, and not in equal measure. Shaper-wear sizes are almost meaningless. You want something snug, but you end up with constricting. You want something firm but it feels like pulling on an old jumper. You wanted shape, you end up losing all feeling in your legs. 

My best item in this area is the slip to the right. It feels wonderful, just the right balance of firmness and give in a fabric that feels gentle and soft. The main downside is that there's a very stiff pair of bra cups built in. You can just about see them in the picture. In real life they're big stiff cups, like strapping a couple of mixing bowls to your chest. When I wear it, I have to stuff the cups. If that's your thing, great, if not, well, keep looking and paying because this stuff isn't cheap.

Pantyhose.

Pantyhose is the the best item you can buy, in my opinion. You pull them on and feel feminine and comforted straight away. There isn't a huge problem with fitting and they're easy to purchase.

Fabric and quality is the key factor here. If they're cheap they won't be good. You want a good, well-known brand. Find a style you like and stick to it. Personal preference dictates all here. For me, black is the only colour. High denier opaques are the only style and the only way to be sure of size is to buy the whole range all and find which fits by trying them on. I have supposedly small pairs which are bigger than other XL sizes. I have ones where the leg has maybe an extra eight inches to spare but the waistband feels like a nylon vice and others where the legs are so short the gusset hangs down between your thighs while the panty flaps around loosely. 

That's okay if they're eight dollars in a three-pack, not so great if they're $46 Woolfords. But it's worth it for the feeling of wearing a perfect pair. And if you find a pair you like - buy three more now. They will go out of production as soon as you decide they're you're favorites.

Crotchless?

Or rather, ones like these where it's like suspenders-built-in. Hmm. So, I only branched out and bought a pair of these this year, and yeah, these are slightly delicious. This particular pair could do with more lycra - they're losing their shape a little and they're getting that 'bally' effect, so I wish there were higher quality ones available. They certainly solve the not-enough room problem and they feel good, not as good as a proper reinforced-panty pair but still, surprisingly good. Further research required.

In all, I think I'm happy with and continue to wear about one fifth of everything I've ever bought. I love buying it. Choosing and shortlisting and waiting for it to arrive is a large part of the fun and excitement. I've bought from figleaves, amazon a couple of specialist hosiery online shops, and of course, Yandy.com. I've even bought a couple of items in person a long time ago when I was braver. I wrote that experience up as an article a few years ago. I might see if I can find it. 

Please comment if you found this article in any way interesting, or even if you didn't. Your comments are what keep me coming back to this keyboard.