I've never really been able to approach girls/women, despite my fascination with them. To me, girls and (young) women are just the most beautiful creatures to walk the Earth. I guess I've always loved how long hair looks on females, but also their eyes, faces, bodies, all different in so many ways from men, just prettier. I am astounded by the way that a different hairstyle or outfit can make them look so different that at first glance you would think they were someone else. The ugly girl in movies is a cliché, but it has some truth in real life. Some girls can go from average to hot just by doing something with their hair, change their clothes and maybe put on some make-up. So to say I am fascinated by women may be an understatement. I wouldn't go so far as to say I am obsessed, but, well, umm. Jealous? Yes, I think most definitely. On the other hand, I am quite happy to physically be a male. I think. I was pretty sure of that until not too long ago, but I may have to explore that question a bit further, if just to confirm my viewpoint hasn't changed.
At one time in high school, the mother of a friend of mine suggested going to the airport and bidding on an auction for unclaimed lost luggage. I was immediately taken with the idea, as that would potentially allow me to get my hands on some actual items of women's clothing. Just so I could touch and play with them, not to wear them myself. At the time, I think I would have considered that notion ridiculous, as it would have looked silly on me. Unfortunately, we never went through with that plan, it just never came up again. I guess I was too afraid of getting back on the subject and having to explain why I was interested.
After that first experience crossdressing as a child, which I guess was mostly forgotten, I again dressed up as a woman about 10 years later. It was meant as a joke. Some friends floated the idea of me dressing like a women for a party and I said yes. I am not even really sure why. Maybe I really thought it was funny, maybe I thought it would be an opportunity to experience something new. But I think one thing that made me go through with it was being able to get access to women's clothing, especially a bra. For me a bra is the most feminine article of clothing and probably the most exciting thing in the world. Not counting women, as they are not objects, but people. So with the assistance of a female friend who supplied me with everything and helped me dress, I went through with it, looked completely unconvincing, but that was kind of the point, it was a joke after all. It was not even that unpleasant an experience, the most unpleasant thing was some boys having the nerve to actually grab my fake boobs. My friends were with me and kept close to me, but they never needed to come to my aid, so I didn't really feel that uncomfortable, despite the fact that I looked just silly. I think I still have the bra somewhere. In any case, it was quite an experience, to feel what it was like to dress up as and be a girl at least up to a point, up to and including unwanted groping. Which, by the way, is bad, but my boobs were plastic and I didn't feel anything. Even so, I was still offended, so I can only imagine..
When I went to college, I once visited a house where a couple girls lived and while going to another room I had to pass a clothing rack filled with lingerie, at least a few bras. I remember thinking how badly I just wanted to be able to just stop and look at them, never mind touch them. Since I was staying in a mixed dorm, at some point an opportunity presented itself. Some girls were, well, careless with their laundry and didn't pick it up for long periods of time. At one point, a whole stack of women's clothes was just dumped on a table in the common room, as someone had wanted to use the laundry machine and had just taken theirs out. Even then they didn't collect it. It stayed there for a while and one item was a beautiful blue pair of panties. Since no one seemed to be paying that heap any attention, after a day or two, in the middle of the night, I snuck out of my room while hopefully everyone was sleeping and I took it. I kind of wish I still had it, it was just that nice and belonged to a girl I found kinda attractive to boot. I took another few items at various points, never got caught although some people might have suspected me. If they did, they never said anything to me. With those ill-gotten items I crossdressed by myself for the first time, on my own initiative. Sometime later, I started ordering stuff online and at some point, the thought occurred to me to just buy some lingerie, just to look at and touch and things like that. Unfortunately, all that resulted in was some really crappy, cheap looking items, which didn't even really feel soft or anything. Moreover, what I really wanted was not the kind of 'sexy' lingerie that no woman in their right mind would wear, but really the ordinary, everyday stuff. Lingerie that actual women would wear, that I would see, just barely, underneath the clothes of women I would see every day in lectures, in shops, walking by on the streets.
After leaving the dorm and moving into a place of my own, I still only had a few items of women's clothing. Some of the stuff I had thrown away as it just was no good and I never really did much with it. I sometimes wore it, but never for long, just when I wanted to feel what it was like while playing with myself. A few years ago however, I got into an experimental phase and was trying out various things. I won't go into details, as I believe that is not allowed, but let's just say that at some point I started ordering various toys and other items online. Once I had access to two sites where you could also buy women's clothing, things escalated. Almost instantly and on a massive scale. It all started just with some sets of lingerie. But within a few months I had started buying other items of clothing, like skirts and dresses. Even a wig, which was so disappointing as it itched like crazy and the synthetic hair felt very synthetic indeed, that I hardly ever wore it and have since thrown it away. The clothes are another matter however. While at first I mostly wore them just when enjoying myself, I am now wearing them more and more. I guess I kind of got addicted to buying women's clothes, because just about every few months of so I have been buying more and more stuff. When there is a sale you can bet I will take hours to scour every part of the women's department for things I might like. Quite often I can't wait for certain items to be on sale and just buy them full price. If I see something that I really must have, I order it immediately unless I really don't have the money. I pick up the packages at a store a town over or have them delivered to my door and stay in to make sure they are not delivered to my neighbours. I really don't want anyone to know about this. I don't get many visitors, which is fortunate, because my collection is starting to be pretty hard to hide. If I had people come over right now, I would be in big trouble. I have many times more women's clothes than I have men's. In shoes and boots alone I have eight pairs. Men's shoes? One pair. Bras? Enough to fill three boxes. Dresses, skirts and tops? Enough that I recently had to buy more clothes hangers. Again. Today I finally made the effort to properly hang up as many items as possible. I ended up running out of clothes hangers. Whoops. I really don't know how I could hide all this stuff and I am starting to think I don't want to. I certainly don't want to just stuff it all in a few boxes and risk damaging things, or throw it all out and for all that money to be wasted. I can't even remember the last time I bought men's clothes. When I am dressed as a man I never really care about how I look. When I dress like a woman, I want even my underwear to match.
On my days off, I often wake up, dressed only in women's panties, although occasionally I wear a bra for the whole night, put on a house coat, run to the kitchen, get something to drink I can take into my bedroom and dress up immediately afterwards, carefully picking out my outfit. Then I go do whatever I feel like, dressed as a woman. Play a game, read, watch a movie, whatever. I only change clothes to run into the kitchen to make lunch, as my neighbours could see me if I am in the kitchen, then dress up again when I return to my room. Or I just pick some pants which, from a distance, can't be distinguished from men's pants, so I won't have to change everything just to pop into the kitchen. When I get home, I often can't wait to change clothes, especially when I have new stuff I haven't worn yet or not that often. I keep finding new favourites, new combinations. I recently bought and tried on pantyhose for the first time, which I had deemed impractical before. I was sold immediately and whenever I don't wear long pants, I now wear hose. Part of me hates it that I have to change clothes every time I leave my room, because people are stupid and judgemental and my neighbours might find out and make fun of me. I would much rather just keep wearing women's clothes, even if just because I am lazy. This is in part compensated by the fact that I get to pick out another outfit afterwards.
It just feels different being dressed like a woman. The clothes are more comfortable, softer. Why aren't men's clothes anything like this? Women's clothes are also designed to enhance and reveal the shape of a woman and it is very exciting and satisfying to wear them. The fake breasts I made for myself just from some fabric and parts of two bras make me feel some pressure on my chest as if there are really boobs there, they even bounce a little when I jump up or walk a bit faster. With the right bra I can almost fool myself. I love how women's pants and tight skirts hug my thighs and sizeable round backside. For a guy, I have a pretty nice, round backside, if I say so myself. That part of me really does look a bit like a woman.
Recently I've also started buying other items. I already have so many clothes, but I still want more, I keep seeing stuff that is just so nice. Now I'm expanding into accessories. Belts, items like hair clips, red lipstick and I am starting to look into jewellery. I hate anything that pierces the skin, but I actually went into a jewellery store and looked at some necklaces. I am trying to decide if I want to let my hair grow long. I am also trying to decide if I will finally cave and shave my legs and maybe my chest hair, but I don't want anything to be too obvious.
I think I need to decide if I want to keep doing this and double down on it, or stop wasting a huge amount of money on something that is still very much taboo and might come between me and a future partner, or something in between. I need to figure out what this really means to me and how I want to deal with it. Could I even give it up if I wanted to?
I really liked what Alex (similarity in name is a total coincidence) said here.
I think, if anything, crossdressing is a way for me to express how much I really like women in all their beauty.It was not a sexual thing for me until I reached puberty. Testosterone makes this into a sexual fetish. However, I believe that those who believe cross-dressing just sexual fetish, have missed the mark. Its more than that. I believe it was hardwired in my brain through synaptogenesis and neural pruning. Now these neural connections create an involuntary response to cross-dressing where our brain interprets cross-dressing as contact with a female and releases a host of neurotransmitters. Dopamine, serotonin and oxytocin are response for the sensations of gratification, well-being, pleasure, and social bonding.
Maybe it even means I am acting as my own girlfriend in the absence of a real one.
Anyone still reading this?
Goodness me, I'll stop now, thank you for your patience. I really think that is pretty much all of it. Oh rly? Yah, rly.
TLDR: the first time I crossdressed I was seven, it was a game, but I'd almost forgotten about it and am not sure it was that significant. I started crossdressing as a fetish a few years ago, liked it a lot, have started collecting enough women's clothes to open my own store and now I don't really know what it means to me, but I probably couldn't stop even if I tried. Also, I write a lot and am weird even putting my crossdressing aside, but a good weird. I think. Also, hi?