Well, my two Halloween experiences were actually pretty different.Originally Posted by Abbey11
The first time was when I was a 19 year-old freshman at a huge state school. I was at my most masculine at this point in my life, deliberately making an effort to drink as much alcohol as possible, fit in with frat boys, and objectify women as much as I could. Halloween came around and of course there were parties to go to, and one of my male friends (one of the frat boys) suggested that I go "as a sl*t." So I borrowed the msot mismatched, skin revealing combination of clothes I could get from various girls on my dormitory floor, bought the gaudiest, cheapest makeup from Walgreens, and a cheap blonde wog from a Halloween story. Me and the guys did out best to figure out what to do with this makeup and of course the results were terrible. I looked nothing like a GG, but that wasn't the point. I don't remember liking the experience in any genuine way (liking how the clothes fit, wearing makeup, etc), though I did kind of like feeling the night air on my exposed (unshaven) legs.
My second Halloween was much more toned down. It was two years ago and I went dressed as Tina Belcher, a character from an animated TV show called "Bob's Burgers." There was no alterior "hidden" motive in wanting to dress as a female character. I'm a huge fan of the show and thought it would be a pretty easy costume to pull off. For those who aren't familiar with the show, Tina is a tween aged, awkward girl with a very flat, monotone voice; in fact, she is voiced by a male voice actor who doesn't really try to sound like a girl. Anyway, she wears a pretty basic outfit consisting of Chuck Taylor Hightops, tube socks, a knee-length blue skirt, a plain blue t-shirt, and a yellow barrette. Her hair already looks like mine and wears thick, black framed glasses just like mine and she doesn't wear makeup, so I didn't need to worry about that. It looked great, though just before we left for the party we were going to, I said to my girlfriend, "Hey...could I borrow one of your bras and stuff it?" she just stared at me for a few seconds and then stammered out "I...I guess so?" She reluctantly help me put on one on and stuff it, and while I didn't expect it to, when I saw myself in the mirror wearing a skirt and having breasts, my heart stopped for a minute as I took in how I looked. Even though I wad supposed to be this awkward tween girl, I thought I looked kind of pretty. Or at least I felt a little pretty.
That experience, jokey though it may be, was the first time that I considered the difference between feeling pretty as a woman than feeling handsome as a man. To your first question, Abbey, that's how I feel when dressed and what I like about it: feeling pretty.
When it comes to dressing in drab (which I do for work and whenever I'm with my girlfriend, family, and friends), I don't really care much about how I look. Of course I have good hygiene and I don't go to work in sweatpants and a ragged t-shirt, but I don't put any extra effort into looking handsome. I don't hate wearing men's clothes, but I don't find anything interesting about them. Men's clothes are purely functional objects to me. I'm just that typical guy who gets up 15 minutes before having to leave for work, brushes his teeth, puts on deodorant, grabs whatever button-up shirt is on top of my dresser drawer, does the same with pants and heads out.
Now when it comes to getting dressed as Christina...that's a whole other story. I don't mind taking a hour to get my makeup juuuust right. In fact, I love it! And the clothing options, my God! I could wear tight jeans that show off my slim legs with a sheer, v-neck t-shirt that shows juuuuust a bit of cleavage. Or I could wear a floral romper with vibrant red tights and black flats. Ooo, or I could wear beige jeggings with a polka-dot top blouse and low heels. And then there's the eyeshadow options, lipstick colors...so many ways to be pretty!!!
So yeah, that's what I get out of crossdressing; I love and care more about feeling pretty than feeling handsome.
