tiffanywin
10-23-2007, 09:11 PM
I’m dying to share this! I am having the best Halloween week ever!
Every year someone at my office throws a Halloween party, so I always have a chance to dress up. And every year I wait as long as possible to pick a costume, hoping that at the last minute, if I appear to be stuck without a costume, one of my female friends will offer to let me wear some of her clothes as a “back-up” costume. So far this tactic has only worked once, about six years ago, and I chickened out and rented a traditional male costume the day of the party.
Finally this year, one of my friends seriously offered to let me wear her nurse’s outfit and went so far as to suggest pantyhose and shoes. I feigned disinterest, but kept the conversation going long enough to work up to the point that I “agreed” to dress as a woman. Here’s where the fun begins.
I have a female friend that I don’t see very often, but with whom I correspond via IM and email fairly regularly. She’s married, but we’ve known each other for years and are good friends. Of course, she has no idea that I’m a crossdresser.
This past weekend I started talking to her about women’s clothes (without telling her about my Halloween plans). I slowly worked up, hint by hint, to telling her that I was actually wearing a skirt and a blouse at that moment. This led to a long conversation during which she thought I was “coming out” to her as a crossdresser. After a while, I played it off as a joke and “revealed” that it was just a Halloween costume. But this was a fantastic dry run for telling someone about my dressing. When we used to live near each other, and we saw each other often, I considered coming out to her many times, but I never got up the nerve. It turns out that I was probably right to keep quiet though, because even though she’s a liberal, open-minded woman, she seemed pretty floored for the few minutes that she actually believed I was a crossdresser, and pretty relieved that it was “just” for Halloween. That having been said, she was very excited about the idea.
So that was one good thing.
The second thing is that now that the prospect of me dressing up in women’s clothes this coming weekend is on the table, we’ve been talking for the last three days all about clothes. I can’t tell you how amazing it is to discuss stuff like this openly for the first time. Today we spent a half hour talking about pantyhose, and the thought that I was talking to a woman who not only knew that I was going to wear them, but was encouraging me and helping me to do it, was almost indescribable. Later this week I’m going to buy shoes, and she wants to know every detail of my shopping trip: what I try on, what the sales person says and what I end up buying. I can’t wait.
Plus, if that wasn’t enough, one of my female friends that I do live near, a co-worker who will also be at the party, has agreed to help me pick out clothes and shoes. So I’ve got a woman to shop for women’s clothes with me and another woman who wants to talk to me about them. I feel like I died and went to crossdresser heaven. Why didn’t I think of doing this before?
I don’t want to push my luck, but I’m toying with the idea of dropping a few hints over the next few days to my out-of-town friend that I’m really starting to like the feel of pantyhose (acting sheepish and embarrassed about it, of course). I wonder what she’ll do if I try to convince her that I’m considering the idea of continuing to wear them even after Halloween is over.
Every year someone at my office throws a Halloween party, so I always have a chance to dress up. And every year I wait as long as possible to pick a costume, hoping that at the last minute, if I appear to be stuck without a costume, one of my female friends will offer to let me wear some of her clothes as a “back-up” costume. So far this tactic has only worked once, about six years ago, and I chickened out and rented a traditional male costume the day of the party.
Finally this year, one of my friends seriously offered to let me wear her nurse’s outfit and went so far as to suggest pantyhose and shoes. I feigned disinterest, but kept the conversation going long enough to work up to the point that I “agreed” to dress as a woman. Here’s where the fun begins.
I have a female friend that I don’t see very often, but with whom I correspond via IM and email fairly regularly. She’s married, but we’ve known each other for years and are good friends. Of course, she has no idea that I’m a crossdresser.
This past weekend I started talking to her about women’s clothes (without telling her about my Halloween plans). I slowly worked up, hint by hint, to telling her that I was actually wearing a skirt and a blouse at that moment. This led to a long conversation during which she thought I was “coming out” to her as a crossdresser. After a while, I played it off as a joke and “revealed” that it was just a Halloween costume. But this was a fantastic dry run for telling someone about my dressing. When we used to live near each other, and we saw each other often, I considered coming out to her many times, but I never got up the nerve. It turns out that I was probably right to keep quiet though, because even though she’s a liberal, open-minded woman, she seemed pretty floored for the few minutes that she actually believed I was a crossdresser, and pretty relieved that it was “just” for Halloween. That having been said, she was very excited about the idea.
So that was one good thing.
The second thing is that now that the prospect of me dressing up in women’s clothes this coming weekend is on the table, we’ve been talking for the last three days all about clothes. I can’t tell you how amazing it is to discuss stuff like this openly for the first time. Today we spent a half hour talking about pantyhose, and the thought that I was talking to a woman who not only knew that I was going to wear them, but was encouraging me and helping me to do it, was almost indescribable. Later this week I’m going to buy shoes, and she wants to know every detail of my shopping trip: what I try on, what the sales person says and what I end up buying. I can’t wait.
Plus, if that wasn’t enough, one of my female friends that I do live near, a co-worker who will also be at the party, has agreed to help me pick out clothes and shoes. So I’ve got a woman to shop for women’s clothes with me and another woman who wants to talk to me about them. I feel like I died and went to crossdresser heaven. Why didn’t I think of doing this before?
I don’t want to push my luck, but I’m toying with the idea of dropping a few hints over the next few days to my out-of-town friend that I’m really starting to like the feel of pantyhose (acting sheepish and embarrassed about it, of course). I wonder what she’ll do if I try to convince her that I’m considering the idea of continuing to wear them even after Halloween is over.