Losing a bet, but in a good way

[seattleshoes]

I've been wearing heels in the privacy of my own home for a couple of years. Every so often I would venture out while walking the dog, or on the occaisional trip to the grocery store. I've kept this part of me hidden, even as my collection of shoes has grown.

I am, and always have been, a fan of the Pittsburgh Steelers. I don't live in Pittsburgh anymore, but I've carried the black and gold on my shoulders - it is rare that I am not wearing something with the team colors on it.

So it turns out that the Steelers and Broncos were playing 4 weeks ago. I'm lucky enough to have a friend to whom I can tell just about anything, and she is a Broncos fan. About halfway through the 4th quarter, it was clear that the Steelers would most likely lose the game, so I asked for a little favor. It helped that I had a couple of drinks in me:

"Look, I know this is more than a little weird, but I like to wear women's shoes, and this is an ideal opportunity for me. Will you back me up if I say we had a bet that would require me to wear women's shoes for a month if the Steelers lose?" It has come out within my group that I have unconventional tastes, but I'd never addressed it directly before with her.

Like I said, I am fortunate to know someone like this. She said yes immediately, adding that she was happy to see someone let their freak flag fly.

I have lots of shoes in my collection, but only a couple of pairs that I would feel comfortable wearing outside. In this case, I've got a pair of Donald Pliner 3-1/2" wedge heel boots that are unobtrusive enough on first look, yet on a second inspection are clearly not men's shoes. They aren't especially elegant, but I'm not an elegant type of guy, and they do the job very nicely.

Basically, I had three groups of people that I needed to convince that this bet was real - 1) people at work, 2) the group I hang out at with at the local watering hole, and 3) a small group of close friends, who I talk to regularly but see only once every two weeks or so.

I needed to prep the work people first of all. As it turns out, I had the following Monday off, but I was emailing my business partner and let him know I had lost a Steelers-related bet, that I didn't want to talk about it, but that it was long-term and wouldn't be good. For the first couple of days I heard a lot of "these boots are made for walking", but since then it has settled down and no mention has been made.

The group at the local watering hole was helped a little bit by fate - I ran into the owner's wife while getting coffee on the Monday after the bet was made. She immediately noticed the extra height, and after a lot of pressing, I "broke down" and told her that I had lost a bet, then showed her the shoes. Her immediate reaction was laughter, but in a good way - she was clearly enjoying the fact that I was not a happy camper. After that, the rest of the group was easy, especially because she spent the rest of the day spreading the word. As with work, I had several days of good-natured taunts, but since then there's been very little conversation, especially when I wore gigantic platforms, a blond wig, and fake boobs to Halloween, all in the name of "owning it"

Finally, the small group of friends, which was pretty easy as well. I hadn't said anything to them for the first week, but the friend that helped me arrange this and another friend were out drinking and I started to tell the story of the bet, acting indignant the whole time. I didn't have to do any work from then on - he bought the story then passed it around via e-mail. When I saw the larger group the following week, all I had to do was say "shut up Stu" a lot in order to sell the idea that I wasn't enjoying things.

Now, I don't like being dishonest with people, and I won't attempt to justify my actions, but things have worked out pretty well. The keys for me were the fact that a) I have a near-perfect reputation for honesty and integrity within the circles I travel in (yes, I understand the irony here), everyone knows that I follow the terms of a bet to the letter, win or lose, c) I'm second-in-command at my office (a small dotcom), and there aren't a whole lot of people to tell me know, and d) I'm known as someone who is completely sports-obsessed.

So, for basically a month, I've had a great run, to the point where I'm working on how to make things permanent in the minds of people I interact with. We added a week because I had two meetings that it really wouldn't have been appropriate to wear the boots, but that week ends on November 25

My co-conspirator and I came up with an alternate plan to extend things - we floated a story amongst the three groups that said she had caught me ducking into the local coffee shop wearing gym shoes, in clear violation of the bet, and that she wanted to extend the term another month because of the cheating. I got some pushback from the local bar denizens, so we came up with an alternate plan that should keep things going for a while - we're submitting the question of the extension to my small group of close friends at Thanksgiving, and we'll agree to do whatever they decide. Due to a little preparatory work that I've done, plus some residual resentment about how the Steelers beat the Seahawks in the Super Bowl a couple of years ago (all of this takes place in Seattle), I'm pretty sure that an extra month will be the minimum.

As I've noted, I don't like lying to people, and I'm sure that it will eventually come out, but I've rationalized it by slowly bringing trustworthy people on board to the truth, and they've been mostly supportive. As time has gone by, it really has become less and less of an issue. If things go as I hope, I will be able to graduate to the pair I really want to wear in public, which I bought at Nordstrom's several weeks ago:

http://shop.nordstrom.com/S/2940330?tuid=000006cb-006f-0861-6c61-726765727669&id=7599465&largeImg=0&tname=product

I'll keep you all updated both on the near and long term parts of this experiment.

[Shoeiee]

Hello Seattleshoes!! That's awesome!!! What a great way to get the people used to seeing you in heels! I don't particularly care for the cover up but a bet's a bet, right?? And I don't think there's one guy who wears heels that's been 100% honest about them since day one... Hopefully this will open all kinds of doors for your heeling in the future. I certainly would love to hear more about your adventures, especially as you can't keep 'losing bets' with the same 'punishment' forever...One day, if you're going to keep wearing heels regularly, you'll have to own up to this but if gives time for a smoother transition IMHO. What would probably work best when that time comes is just simply saying "You know, these aren't all that bad after all and I've decided to just keep on wearing them. They're only shoes for Pete's sake!!" And then you've entire collection (well, minus the really fetishy stuff most likely) would be available for your regular enjoyment Wish you the best with all of this!!

[Dr. Shoe]

What I would do is to start "enjoying" it and say things like "I'm starting to like this," or "I think I might wear heels permanently from now on..." just to see what sort of response you get.

[Thighboots2]

Shooie & Dr shoe have hit the nail on the head, just mention how much more comfortable you find the footwear, etc, etc. We all like how much lighter the shoes are compared to the heavyweight, and chunky stuff we are served up with mornally. Why have mens shoes got to be so utilitarian? TB2

[seattleshoes]

Already there. When the time ends, whenever that is, I hope to have accomplished 3 goals: 1) People are used to seeing me at 6'2" rather than 5'11". I can always say "Hey, I decided I liked being that much taller" 2) Get over the hump on wedge vs. click-y heels. Right now, I am unobtrusive, but clicking is a different thing entirely. One thing I didn't add is that my co-conspirator and I have adopted a "if you're cheating, you're clicking" clause to the bet, at least for Thanksgiving Day. We'll see how that goes - once I get over the mental stumbling block of the clicking, a lot of things open up, and the small group is a good place to test things out, as well as manipulate a "mandated" click-y heels experience when I see them. 3) Adopt an attitude of "once you get past the difference between traditionally male vs. traditionally female shoes, and you've proven you can take the occaisional barbed comment, what does it matter to you what I'm wearing on my feet? " I've basically decided that the stock answer I will give when asked "hey, didn't that bet end several months ago?" will be "yes it did, but spending that much time in women's shoes, I realized that I like being taller, I like the increased variety, and if people have an issue with what I'm wearing, I really don't care. I've known you for [insert some time period here] years. Do you really think this lessens my porn/sports/porn addiction, which we can talk about for years on end?"

[c_heels]

Wow, great idea with the bet! Must be nice to have a friend that you can confide in and do something like that. Also, love the boots you posted! Worn them out yet?

[Pumps]

Excellent story, Seattleshoes A great way to wear heels "legitimately" and frankly I don't see how this is lying. You made a bet, right ? So what if it was a bet you wanted to loose ? I'd do the same thing if a got the chance. I'd give my right arm to have a female friend who was cool about my heeling. That would be so cool.

[loswabs]

How about saying you had a few ladies say they thought you looked really hot in your heels and why didn't you wear them all the time? Or maybe moving on one step from that, say one or two ladies saw you without your heels and thought you looked much better / sexier with them on?

[dressboots]

So, has anyone asked what your friend would have had to do if you won the bet? Go out with you while you are wearing womens heels? I certainly would have wanted to know that of anyone I knew who lost a bet with the result you cooked up. Sounds like a great idea and have had fun reading the thread.

[seattleshoes]

Her side of the bet was that she'd have to wear Steelers gear for a week. This was fairly reasonable given how much the Steelers were favored over the Broncos. On top of that, neither of us subscribe to Sports Bigamy - the thought of wearing another team's jersey makes us a little crazy. The effect of all of this has been interesting. On one level, it has been freeing to just wear what I want. On another, it has been a little bit desensitizing in that I was pulling on heels every day for a month, and a little bit of the thrill has been taken away. All in all, I'm still happier that I did it. I've learned which of my friends are OK with this part of me, and I've learned which friends would rather not think about it. As much as we all feel we should be free to do what we want, the rest of the world is not so enlightened, and there is no reason to poke them with a stick when I can carve out areas where I can feel completely comfortable. And one more side effect - the number of women in my group of friends who have pointed out that they think I look better at my new height, and that my butt looks "hot" now. Once they got past the whole "heels are for girls" thing, they actually appreciate the overall look, especially because I'm not going out of my way to emphasize the heels, but rather attempting to integrate them into the entire outfit.

[dressboots]

So have you been able to transition heel wearing into part of your regular look? If so, were there any bumps? Some might be pretty much of the attitude that they concluded that about you as you adhered to the rules of the bet so religiously. Others might draw negative conclusions. Losing a bet and doing it involuntarily is one thing but doing it by choice might another. Just curious.

[Dr. Shoe]

The effect of all of this has been interesting. On one level, it has been freeing to just wear what I want. On another, it has been a little bit desensitizing in that I was pulling on heels every day for a month, and a little bit of the thrill has been taken away.

This is what happens...

[jmc]

This is what happens...

. . . and this is probably the root cause behind the "waning desire" phenomenon that so many of us have discussed in other threads. Some of us even go so far as to purge our collection of heels when the thrill fades. . .

. . . but it always comes back.