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Dressing Up

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Sometimes I pretend I'm a girl....

I Feel Like a Girl, Part 1
Feeling Like a Girl, Part 2

 

This Halloween reminded me of the Halloween that I dressed as a girl. I loved it. I felt soft and comfortable. I'd worn other costumes other years--ghosts, hobos, baseball players--but this year I asked to be a girl. It didn't phase Mom. My mother made the costume especially for me, with as much love and care as she made a special baseball suit, and a jet pilot's uniform, and several cowboy outfits. And I didn't turn into a transvestite or even a cross dresser(well, maybe a little, as you'll see).
I think I wanted to dress as a girl because girls are really cool. They're pretty, and nice and soft and kind and gentle. Boys are kind of gross and ugly. I like guys, but sometimes I don't much want to be like them.
When I first wrote 'Feeling Like a Girl', I didn't remember one thing that I do now--I actually got a pre-pubescent sexual charge dressing as a girl and now I remember having an erection under my skirt. Later, when I learned to masturbate, I'd remember how I felt under that Halloween costume.
I still like to change my style a little, not for show, but according to how I feel. I have some clothes that could just as easily be worn by a girl--jeans, tee's, certain fine sweaters and shirts, and so it's my choice how I feel in them.
I had a just out of college who was a kind of macho guy, and when I was with him, I always felt kind of like I was his girlfriend or something. It's just the way that you had to feel around him, unless you were really macho yourself. I used to resist that, but then, I just gave up and said, ok, I'll be a girl with him. Of course, I never told him, and he probably didn't notice, but when we'd get together, I'd wear a special shirt or something, and I'd pretend inside like I was a girl, or that we were not two guys hanging out, but were on a date.
I liked being his 'girl'--secretly--nobody would ever be able to notice. And, on some occasions, when I got home I had some pretty hot girl fantasies while I masturbated, and even imagined sex with my friend. And we got along great.
I'd had a brief fling wearing sexy women's underthings once, and got my thrills for a couple of weeks, and then returned to 'normal.' But not quite normal. I kept a couple of bras (sexy and sport), and sometimes wore them in private at night to get in the mood for very soft and feminine masturbation. So one day I thought, 'Hmmm, what would it be like to be out with him wearing a bra (that he never saw)' and so I did it. It was my own secret, it was so much fun, and I felt very attractive, and that night when I masturbated, I imagined him biting my nipples and hurting and being rough with me.
Going to a show, or shopping, or to a party, I'll slip on a bra--sometimes not even wear it going out, but just slip it on for a while before I go out, enough to get in the mood. I got this crazy idea to get some pads and fill out the bra until you could see something under my sweater if you were really looking; and I went out in public like that, by myself. I'd get that warm feeling between my legs...and a third bulge would appear.
Sometimes, after a night out, I imagine doing a slow strip tease as I undress, and then spread out on the bed and rub between my legs and pinch my tits and, it feels wonderful, but I usually then have fantasies of my girlfriends and imagine my cock in a nice warm pussy.
I'm a vice president of a construction company now, and I have different costumes. I have my construction outfit, Levis and jackets, and I can be very manly. I have my softball outfit and I have my cool designer clothes, too, for meetings with clients, and what nobody knows but me is that sometimes under those clothes is a soft and gentle guy/girl. The head of our company is a lot like my friend-macho, a man's man. We make a good team.
A week ago, we went to a conference. On a whim, I packed a sport bra, which I wore under my sweater to a banquet. I had a great time. I schmoozed a new client (a woman) who admitted she didn't like my boss, but felt really good with me (wonder why!); and later in the conference I scored the with a rep. lady from one of our suppliers, who liked me because I wasn't so 'macho' as all the others. My boss had a boring time...(too bad!).

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