My new boy, simple twist, volunteered to dress up as a school girl for a Halloween party this weekend and then to let me share his report with you. I'm very proud of him as this was his first time going out in public dressed!
I'm hoping his report will inspire more of you to take a step outside your normal comfort zone and use the rare opportunity that Halloween gives you to dress as your fantasy - whether it be as a girl, a puppy, a baby - whatever your heart desires. Send your reports to me at: ForMistressMagick *at* yahoo *dot* com, and maybe I'll include them in my blog.
*
Mistress Magick,
I decided to dress as a girl for my Halloween party earlier in October, shortly after You had told me that You often make it your Halloween assignment for your boys to dress as their fantasies. You hadn't specifically told me to do it, but I knew it was something You'd like so I decided to do it on my own.
[Good boy! I like a boy who thinks ahead about ways that he might please me. ~ M]
I decided to go as a school girl and started looking online to piece together a costume. I soon found a pink, short plaid skirt, a white blouse, white tights, black high-heeled Mary Janes, and a blonde pigtail wig.
I was afraid of going too far with the costume, as people would begin to wonder how much of this was something I wanted to do even if it wasn't Halloween. I decided the tights and heels would make me look very feminine, but it would be offset by my beard and the campy ridiculousness of the wig.
The big night came, and You were generous enough to arrange your schedule so that I could get dressed for the party on cam for You. I felt very vulnerable dressing for You. My sissy fantasies are the ones I have the hardest time coming to terms with, but it also made me feel very submissive to You when I was on cam dressed like a girl.
I could tell that there was going to be quite a contrast between my lower half and my upper half. From the waist down I looked very feminine, with my legs encased in white tights and given a nice feminine form with the high heels. Above the waist I had a beard and a flat chest, but if I looked any more feminine, I don't think I would have been able to get up the nerve to go out in public.
After checking me out full over, You finally sent me on my way to the party. The first thing I realized that I had underestimated was driving in heels. It was a bit awkward at first, but I got the hang of it within a few blocks. When I arrived at the party, I took a deep breath and walked up to the house. Before I could talk myself out of it, I opened the door and walked in to see all my friends. The initial shock was priceless - no one saw my costume coming! People were even more shocked when they realized that I wasn't only wearing a skirt and tights, but heels as well. Another friend of mine was also dressed as a girl, but he wasn't nearly as feminine as I was. While he was simply a guy wearing a girl's Halloween costume, at least from the waist down I was dressed like a sissy - in a short pink skirt, white tights and shiny black high heel Mary Janes.
Everyone got a kick out of the costume though, and soon I was able to relax, have a drink, and start having fun.
There was one woman at the party who was younger than most of the people there, and she seemed very much pushed out of her comfort zone with me dressed as I was. She couldn't stop staring at me, and whenever she walked by she'd say she couldn't get over how much I looked like a girl. I assume she meant my legs.
One of the girls looked at my shoes and told me that in an hour I'd have regretted wearing them. She wasn't kidding either. After a while my feet began to hurt, but I did my best to keep the heels on for as long as I could. But after being in them for almost 3 hours, I had to make a change. For the last hour that I stayed at the party, I was in my sneakers instead of my heels.
I got home around 1:30am, and decided to stay in my costume and put my heels back on as I relaxed. I ended up laying in bed still wearing everything, and fell asleep that way. It wasn't until I woke up in the early morning that I finally took the shoes and rest of my costume off and got into bed proper.
Going out like this definitely pushed me well out of my comfort zone, but it was thrilling at the same time, and felt good to put myself on the line like that for Your pleasure. I'm glad I was able to make You proud. I joked to a friend the next day that I'd have to keep the shoes handy, and next year I could "go as a French Maid or something". Who knows, maybe that'll happen.
*
So noted! ;-)
Mistress Magick,
I decided to dress as a girl for my Halloween party earlier in October, shortly after You had told me that You often make it your Halloween assignment for your boys to dress as their fantasies. You hadn't specifically told me to do it, but I knew it was something You'd like so I decided to do it on my own.
[Good boy! I like a boy who thinks ahead about ways that he might please me. ~ M]
I decided to go as a school girl and started looking online to piece together a costume. I soon found a pink, short plaid skirt, a white blouse, white tights, black high-heeled Mary Janes, and a blonde pigtail wig.
I was afraid of going too far with the costume, as people would begin to wonder how much of this was something I wanted to do even if it wasn't Halloween. I decided the tights and heels would make me look very feminine, but it would be offset by my beard and the campy ridiculousness of the wig.
The big night came, and You were generous enough to arrange your schedule so that I could get dressed for the party on cam for You. I felt very vulnerable dressing for You. My sissy fantasies are the ones I have the hardest time coming to terms with, but it also made me feel very submissive to You when I was on cam dressed like a girl.
I could tell that there was going to be quite a contrast between my lower half and my upper half. From the waist down I looked very feminine, with my legs encased in white tights and given a nice feminine form with the high heels. Above the waist I had a beard and a flat chest, but if I looked any more feminine, I don't think I would have been able to get up the nerve to go out in public.
After checking me out full over, You finally sent me on my way to the party. The first thing I realized that I had underestimated was driving in heels. It was a bit awkward at first, but I got the hang of it within a few blocks. When I arrived at the party, I took a deep breath and walked up to the house. Before I could talk myself out of it, I opened the door and walked in to see all my friends. The initial shock was priceless - no one saw my costume coming! People were even more shocked when they realized that I wasn't only wearing a skirt and tights, but heels as well. Another friend of mine was also dressed as a girl, but he wasn't nearly as feminine as I was. While he was simply a guy wearing a girl's Halloween costume, at least from the waist down I was dressed like a sissy - in a short pink skirt, white tights and shiny black high heel Mary Janes.
Everyone got a kick out of the costume though, and soon I was able to relax, have a drink, and start having fun.
There was one woman at the party who was younger than most of the people there, and she seemed very much pushed out of her comfort zone with me dressed as I was. She couldn't stop staring at me, and whenever she walked by she'd say she couldn't get over how much I looked like a girl. I assume she meant my legs.
One of the girls looked at my shoes and told me that in an hour I'd have regretted wearing them. She wasn't kidding either. After a while my feet began to hurt, but I did my best to keep the heels on for as long as I could. But after being in them for almost 3 hours, I had to make a change. For the last hour that I stayed at the party, I was in my sneakers instead of my heels.
I got home around 1:30am, and decided to stay in my costume and put my heels back on as I relaxed. I ended up laying in bed still wearing everything, and fell asleep that way. It wasn't until I woke up in the early morning that I finally took the shoes and rest of my costume off and got into bed proper.
Going out like this definitely pushed me well out of my comfort zone, but it was thrilling at the same time, and felt good to put myself on the line like that for Your pleasure. I'm glad I was able to make You proud. I joked to a friend the next day that I'd have to keep the shoes handy, and next year I could "go as a French Maid or something". Who knows, maybe that'll happen.
*
So noted! ;-)
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