First time Out
My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing her panties to work, painted my toenails, and she even did my make up. We did break up, but I still kept in touch with her. I did tell her about my plans for Halloween and she was so excited. She wanted me to get all dolled up that nobody would recognize me. She even came up with a name for me: Aimee.
So, I went shopping with my friend for clothes for me to wear. I picked up a black mini skirt, heels, and a blond wig. I was really into this excursion. When I told Mel what I picked up, she helped me get some accessories at a costume store she worked at. I picked up some eyelashes, nails, and some tights. She wasn't going to come out for Halloween, but she wanted me to take some pictures.
On the day of Halloween, I got to my friends house where she applied my make up, and adjusted my wig, and made me look good. It was hard for me sitting there getting make up applied... I was very turned on. I put on my skirt, tights, and a little pink top, and my heels. I looked in the mirror, and damn I looked good. I hardly recognized myself. We went to house party, and it was very weird wearing heels, but I did manage. There was a bunch of people there and I was a little surprised how many people I knew, that didn't know who I was.
I was really getting into my girl motif and was kinda checking out some of the guys. I wasn't gay but just the way some of them was looking at me, was really turning me on. Nothing came out of the evening, but I went home thinking about some of the guys who were at this party.
When I went to see Mel the next day, she was all excited to hear about the party, and how my costume went. I told her it went well, and that hardly anyone recognized me. She was so happy, and I mentioned to her that it was too bad that she wasn't there to see me. I did casually say that if she wanted to see me as a girl, maybe we could go out for a drink. I could tell she was excited so we made plans for Friday night.
I didn't tell her that I was already practicing my make up and got a sexy long brown wig to wear that night. I got to her door, and she answered and by the way she looked at me, she didn't recognize me at all. I was thinking this is going to be good. I told her it was Aimee, in my best female voice, and she looked at me again, and smiled. I was wearing a short jean skirt, black tights, spiked heels, a turtle neck and a leather coat. I had light blue eyeliner on , black mascara, and a light foundation on my face. She invited me in, and we chatted for a while. I could tell that she was really taken aback on the way I looked.
I then told her that I wanted to go out and pick up a guy dressed as a girl. The expression on her face said it all. She was really into that idea. She then told me she always fantasized about me being with a guy when we were dating , sucking his cock, and getting fucked up the ass. I then told her that was my thought too. She then took my hand, and told me that's what the plan was tonight. I was going to find a guy, pick him up, and then give my first blow job.
To be continued....