Well, here goes...
I guess it all started back in the start of high school. I was just beginning to hit that golden point, the start of puberty. We were planning on moving across the town that I live in and so I began school at the new high school instead of the old one that my friends were all going to. New kids, new fears, and did I mention I'm a huge introvert irl?
Well, my parents (mother and step-father, parents both divorced and remarried) always worked until 5-6ish and my brother ended school later than me, so I had the house to myself a lot. It was then that I obtained the urge to try on my mother's panty hose. It was just lying on the floor in her room, the door was open, so I figured, "why not?" And so I did it, not realizing that this way my first step into a much larger world.
I began wearing hoisery under my pants after school this way for a little while. By this time we had moved to the new house and I had even more free time, since we were now fairly close to my high school, and I didn't need to take a 40min ride home every day. This went on until one day something very strange happened: I ejaculated for the first time, and I didn't stimulate it with anything other than the hose. I didn't know what was going on as I had never had the sex talk, plus the internet was quite new and so I really had no experience in the matter. It turns out I had a clothes fetish of some kind, as I escalated from hose to other garments.
Now I never spoke of this to anyone, and nobody ever discovered what I was doing. By the time I graduated high school, I was playing with bras, underwear, half-slips and a little makeup. I wasn't really certain what I was doing, only that it was gratifying.
In university, I met a girl that was in her last year of highschool up the street from my school. She and I began dating, and it was her that brought up the idea of me venturing outside in a kilt. Now, I had never really worn anything substantial before, being mostly lengerie (sp?) and other undergarments. I hadn't told her about my sexual stimuli, and so I 'grudgingly' agreed to do it to make her smile. I got a few looks but it was in good fun so people shrugged it off as kids goofing around. Thing was, this escalated me another step. I was now interested in the rest of the wardrobe.
From this point on I was now actively searching for ways to get in drag. My mother's clothes were too big, which is why I never managed to do anything like that earlier, so I left it to my girlfriend to find ways of 'coercing' me into situations. And it worked! I eventually came clean with her, but unfortunately this actually caused her to lose interest in the idea, claiming it wasn't as 'fun' for her. We eventually broke up over other issues, although I still keep in touch with her. Still, there were some moments. One such moment was my first Anime North.
Now, for those that don't know, Anime North is a fan-run convention held in Toronto every May 2-4 for anime and gaming fans to come together and discuss, purchase, and otherwise indulge in these hobbies. I had never been to one before, and so it was an interesting first experience. The reason being? Cosplay. Cosplay is the dressing up as a character from your favourite show, game, movie, what have you. Sly creature that I am, I managed to plant the seed in my friends to convince me to cosplay in a girl's school uniform (there's a lot of highschool-based animes). And I did! I guess you could technically call this my first outing although since this was a private convention, I wouldn't really count it. There were other people in much more outlandish clothing than I, although I was rather popular with some of the fangirls
still, this was a monumentous achievement for me. I had dressed for an entire evening as a girl, in front of a whole ton of strangers. I felt exhilarated. I was liberated! I had to do it again next year, but I'll get to that.Moving along, come to the start of my 2nd year of uni, where I began dating another girl. I had known her for 3 years we were best friends, and I was a friend of the family (and still am). Now dating her had been a bit of a dream for me since I first met her, although I hid my true feelings for lack of ruining a good friendship and possibly the friendship of her two brothers. Indeed, the youngest one (5yrs younger) thought I had betrayed his trust by dating his sister, although he eventually came around. We're still best friends, despite the age gap. When I was with her, the urges to dress receded somewhat, although I still had my moments. Remember, most of my CDing was done in relation to sexual gratification at the time, so a sex life pulled me away from needing that gratification. However, we lived in different cities at this point due to school and did not see each other often. Eventually we broke up, but remained to this day very close friends.
Now, this girl was the one who ultimately helped me get my first Anime North costume together (my first gf helped with the costume, but did not go to the convention). Both girls also helped me with the new one, which utilized my first gf's prom dress. Behold, Anime North 2007! By this point a few of my friends were beginning to wonder about me, but the dress was actually pretty anime-looking in appearance (it was purchased at pacific mall, an asian mall), consisting of a corset top and frilly, poofy thick dress bottom. My second gf did my makeup and nails, and off I went!
Now I know I kind of skipped a whole year there, so I'll come back to that now. I was slowly trying to move up the chain in clothing, but as my sources were limited, I was held back from continuing. I was still too nervous to even think about shopping for stuff, so things were on a standstill. Still, I managed to obtain a pair of jeans from my first gf by the time Anime North 2007 hit, and shortly after I gathered up the courage to buy a second pair. My second ex accompanied me with this, as I had talked with her about my issues with the 'gender barrier'. I passed it off as more of an "I don't care what people thinks, I'll do what I want" idea, but I think she got the message clearer than I thought at the time.
I began wearing these jeans around for a bit, seeing how people would react to it. I began painting my nails black too, and this warranted a little more attention. However, people saw it more as an 'emo' like phase than anything else, so I wound up dropping the experiment, as it were.
So having failed my mini-outing, I receded back into the closet, closing my doors once more and pretending I was 'normal'. Unfortunately, things aren't so easy. By this point I had begun to fantasize about different things when I...you know. It became less of the traditional 'picture a girl' scenario (I don't watch/read porn) to "whatever works". This started becoming hazy, and led to me questioning certain aspects of my sexuality. I began to wonder if this was straight behaviour, and if not then what was I? I was, and am, interested in women, but when in drag, I sometimes fantasized about what sex would be like as a woman! Before long, I began bottling these tendencies back up for fear it might cause me harm, and all was well again.
But this is not the end of the story. Recently (like, at the time I first posted on this site), I began to get those feelings of stifling again, and so I brought it up with my second ex. I outed myself, and she found Wildside's site online and showed it to me. I read the site through, and we decided to plan a visit (23rd of May, which we will be going.) I became exhilarated, even if we only wind up looking around, it's still a movement in a new direction. I then began looking up other sites, visited forums, and began outing myself to a few other friends. There are now 5 people that know what I do, although one of them is my first ex, and she only knows what I initially told her, not about the escalation since then. So technically it's 4. My second ex, a close friend and his girlfriend, and another friend. They have all been very supportive so far and each of them has offered to help me in whatever way they can, being shopping, trying on clothes for them, talking about it, or even going out in drag with them. It's still early for me since exams are soon coming, so I haven't been able to act yet, but it is only a matter of time now before things become much more public.
As you can tell, by this point I was lessening up on the gratification and became more interested in the actual feminization process. I began to look for ways to pass, and wonder about why it is important. I began fantasizing about being a woman, and what it would be like. The sexual fantasies have begun again, and I'm unsure at to what they portend.
For the record, I am your pretty average gamer/anime nerd. I'm still attracted to women and not men, and I act like a male, but as you can see it's a very confusing process. I'm not really certain what to make of it, but ideas as to what's going on is always welcome.
I guess that's as far as my story has taken me so far, if I have left anything important out or muddled the organization so that things seem confusing, let me know so I can straighten things out.
Thanks for reading.
Although you wouldn't know it from meeting me in person!
Maybe the outward appearance changing might shift my personality a bit though, give me more self-confidence, so who knows.