DRESSING UP FOR HALLOWEEN
by
Cory

Once, I worked in an office with several people. All of them happened to be women. It was the day before Halloween, and everyone in the office was talking about the costumes they were going to wear the next day. Before I left, one of my co-workers Lauren said "Come on Cory, dress up for once." You see, I was one of those people who had no interest in dressing up for Halloween. I had no problem with anyone else doing it, but it wasn't really my thing. I said "Sorry Lauren, it's not my thing." She jokingly said "You're no fun." I said "Yeah, I'll see you later Lauren." What neither Lauren, nor anyone else knew is that I had planned to dress up, but I wanted it to be a surprise.

The next morning, just before I left for work, I got out several items and put them on my bed. Like I said before, no one had any idea that I was dressing up, and they would be shocked to find out I was dressing up as a woman. That's right, I said a woman. I had always wanted to dress like a woman for one day, but I never had the courage to do it, until that day. The first thing I put on was a black curly haired wig. I noticed that the wig was more in the style of actress Lacey Chabert's hair. Next, I removed my shirt and taped these huge fake silicon breasts to my chest. It felt weird having them on, but it also felt good having breasts. After squeezing and playing with them for a bit, I put on a hot pink strapless 42DD bra.

The bra was SO comfy, and I really liked how I looked in it. I then put on a light hot pink sweatshirt with a heart on it, and in the heart it said "Cutie."After I removed my pants, I slipped on a pair of purple Hanes Her Way nylon panties. I had never worn nylon underwear before, and as soon as I put it on, I said out loud "Why is this the first time I'm wearing this?" I then slipped on a pair of women's pink sweatpants. I stood in front of the mirror and admired myself for several minutes. I then put my hands on my hips and said out loud "I'm so pretty," and I made several kissy faces at my mirror. After I picked up a black purse full of lipstick and makeup, I left the house to go to work.

My heart was pounding like crazy the whole drive there. When I got there, I got out of my car and I walked inside. The first person I saw was Lauren. I said "Hi Lauren." She looked at me, and she got this confused look on her face. Suddenly, her mouth dropped and she said "Cory, is that you?" I said "It is. By the way, for today, my name is Lisa." She said "Okay. Wow, you look great! I thought you weren't going to dress up for Halloween." I said "I had this planned for weeks. I didn't say anything, because I wanted it to be a surprise." She said "Well, it's a pleasant surprise. I notice your boobs are fairly big."

I said "Yes. I taped these to my chest." She asked "Are you wearing a bra?" I answered "Yes, I'm wearing a hot pink strapless 42DD bra." She asked "May I see it?" I said "Sure." So, I lifted up my shirt and showed Lauren my bra. She said "I have to say Cory you have a good taste in bras." I said "Thank you. This bra is so comfy!" I could tell by the look in Lauren's eyes she wanted to touch me, so I let her. She squeezed my breasts and she laughed and said "Wow, they're so squishy!" I laughed and said "I know. Did you know I'm also wearing panties?" She said "No way!" I said "Yeah, I'll show you." So I pulled my pants down a little and showed Lauren my panties. She gasped and said "Those are beautiful!" I said "Thank you. They're purple Hanes Her Way nylon panties." She said "What do you think of them?" I said "I love them. I loved them the second I put them on."

Lauren then said "I have to say I'm very impressed. It takes courage for a guy to dress like a woman. Not only that you're dressed in a sexy yet classy and elegant way." I said "Well thank you very much Lauren. I'm glad to hear that. I've wanted to dress like a woman for a while and I thought why not do it now? By the way, I have to say that you're dressed in a sexy yet classy and elegant way also."

She said "Thank you. I've always wanted to dress like a ballerina." I asked "Do you like it?" She answered "Yes, very much. I feel sexy and I feel like a woman wearing this." I said "Well you should feel sexy, because you sure look sexy in it." She blushed and said "Awww thank you." What Lauren didn't know was I had a huge crush on her, and what she also didn't know was that I'm a sucker for seeing a woman in a ballerina outfit, especially an all pink one like she had on.

Lauren and I talked for a while longer, and then we went to work. I received a lot of positive comments about my outfit. The best part was at the end of my shift, Lauren came up to me and gave me her number, and she told me that we should hang out sometime. To say I was excited was a big understatement.

I kept everything on the rest of the night. I even slept in the clothes! It was safe to say that this particular Halloween was the best Halloween of my life.

The end
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