Halloween Skirt

by Michelle Fox

 

It was October 30 when I was on the phone talking to my friend Megan who I was going to spend Halloween with this year. She and I were just talking about where we were going to go tomorrow when suddenly she asked what I was going to be. I hadn't really thought about it that much until she sprung the question on me. I told her I didn't know. She said I should think of something soon seeing that Halloween was tomorrow. I told her that I had just decided to go as a girl. I was being sarcastic right then. She laughed and asked if she could do my hair and make-up. I said in a sarcastic voice. She told me I really should be a girl and I decided what the heck why not what could hurt. After we were done talking I had thought about what was going to happen. I then forgot about. Now for a little information about me. My name was Matt and I had always been fascinated with cross-dressing the fabric and feel of girls clothes just got me all excited but I was able to hide my desires perfectly. My parents are still together and I have a brother that is away at college and a sister that lives home and goes to college.

The next day I woke up and remembered what I was going to be doing that day. I did not if I was supposed to come dressed or if she and her friend Katie had picked something out. So I called but no one answered. So I decided that I would get some clothes put together just in case. So I pulled out my pair of girl pants that I had bought during the summer because I wanted a pair of really tight pants, but I shoved them away into the back of my closet because I had decided they were to girly. So I took the pants and placed them on my bed. I walked into the kitchen to find my sister getting ready to leave. It took me like 5 minutes to build up the courage to ask if I could borrow some clothes for tonight. She asked what I needed. I responded by saying a shirt and a bra. She looked surprised when I said bra. She told me to come up stairs with her and she would pick some things out. First she took me to her lingerie drawer and pulled out some bras. She pulled out a baby blue satin bra that clasped in the back and a red one that also clasped in the back. She then said the red one would be cuter but it would make look like a slut if it was seen under my shirt, but she also thought the blue one would be adorable. She told me to choose and I said it didn't matter to me. She then told me she would decide after she found a perfect shirt.

She started looking through shirts and asked what kind of shirt I wanted to wear. I told her I didn't care and that she should decide. She asked what I was wearing on my bottom. I told her my tight girl jeans and she said I should wear a tank top. She picked out three tank tops. One was a pink tank, another was an army tank, and the third was a black lacy floral tank that was laced on the bottom and a small lacy bow that hung lace from it. In my mind I screamed for the third one. She told me to run downstairs and put my jeans and be quick because she had to go soon. I walked down the stairs and into my room and put on the tight pants. I got an erection as soon as I put them on. I tucked my penis between my legs and walked back up stairs. When I got up there she told me to take off my shirt and she handed me the red bra. I took off my shirt and then said that I didn't know how to put on a bra. She said she would show me to my surprise it was not the way I expected.

She pulled off her shirt then unhooked her bra in sexy manor. I was getting aroused. But then I realized she was my sister and turned around. She asked why I turned around I wasn't going to learn that way. I turned back around and her giant boobs were just there out in the open she then said not be embarrassed since I was dressing up as a girl and would be more of her little sister than her little brother. So she then decided to tease me and said "go ahead grab them Michelle" and told me that she was going to call me that every time I did something girly or wore my girl jeans. I said fine it won't be happening often. So she then told me to feel her boobs just to see what they were like and that if I really liked the feel of them she would buy me a pair. I gave a sarcastic laugh as I brought my hand up to her boobs and gave them a little poke. She said "don't be a girl and grab them" as she laughed at her statement. So I did and I caressed them for like 5 minutes thinking to myself that I might take her up on that deal she had made. She made me stop when she noticed my erection protruding through my pants and then said I was getting a little happy. She told me she would let me have some more fun with her boobs another time. She then pulled her bra around her back and fastened the clasp on her boobs and then switched it around so her boobs fit in the cups of her bra. I then picked up the red bra and did the same. She said "Michelle you look adorable." I ignored her and put on the pink tank. She said that didn't match the pants. I put on the army one and she just said NO. Then I put on the black lacy one she loved it but told me to change bras because the red one didn't go well with it. So I took off the tank and took off the bra. I started to put on the blue one but I was taking my time trying to remember how to do it right. She grabbed the bra and told to put my arms out and she put it on for me because she was in a hurry. I put the tank back on and she said perfect. She ushered me out of her room with the clothes still on me and she said change down in your room. So I walked down the stairs hoping my dad and mom wouldn't see me. I had gotten lucky that time. I got to my room and as I was about to take off the bra my sister came into the room and said bye Michelle and then left. I finished taking off everything and placed it on my bed in preparation for tonight.

 

To be continued…

  

  

  

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