I once won a competition for dressing as a woman! Seriously.....
By James72
@James72 (26790)
Australia
September 18, 2008 7:48am CST
When I was in High School back in the 1980's there was a school event one evening and some bright spark in the faculty decided that it would be a fun idea to have the girls dress as boys and vice versa. So, much to the obvious delight of my Father, my Mother wnet all out and dressed me completely as a woman with the shoes, hair, make-up stockings, fake breasts and everything!
There were probably around 400 or so other students at this event all dressed as the opposite gender and when it came to judging time, I won the orize as the most convincing male to female transformation! God help me. Do you think I ever lived THIS down? 
To be honest I wasn't overly embrassed at all and found the whole thing very amusing! But those that know me and hear this story never believe me for one minute! Thank goodness my own Mother can back it up!
Can anyone top this achievement in terms of quirky and bizarre events in their life?
To be honest I wasn't overly embrassed at all and found the whole thing very amusing! But those that know me and hear this story never believe me for one minute! Thank goodness my own Mother can back it up!
Can anyone top this achievement in terms of quirky and bizarre events in their life?3 people like this
8 responses
@alokn99 (5717)
• India
18 Sep 08
I can't top it James but i can try and equal it. I went through the same expereince in a group event sort of like a fun workshop in my highschool. It was amusing but equally embarrasing because it was not my mother but a bunch of the other girls in the group. It was 10 guys selected to be dressed up in this way. Am i glad that this was one event i did not win. And you why i did not win? My manly whiskers had started to become quite evident and visible then.
2 people like this
@James72 (26790)
• Australia
18 Sep 08
Ha ha! Well I hadn't even started shaving yet back then and was only around 13 or 14 or so..... Yes it IS a mixture of embarassment and amusement and at least you too had 9 other guys alongside you so the teasing is kept at a minimum! If this opportunity ever comes up again make sure you shave next time. A win is a win right? Thanks for sharing your story and giving me some support on this one with a similar experience! lol.
Thanks for sharing your story and giving me some support on this one with a similar experience! lol.1 person likes this
@zhaosonghan (1039)
• China
18 Sep 08
It must be funny.I can not imagine the situation of that time,you must have a good time.I remember that i have ever dress a skirt at my time of kid,and i have danced,haha,it's very impressive.If when i trun back school and there is a event in my school and i must join,i don't miss this funny party
2 people like this
@SViswan (12051)
• India
18 Sep 08
lol..it must have been funny. It's easier for a girl to dress as a boy but not easy for a boy to dress as a girl. Your mother must have really put in some effort for it!
I once dressed up as the Principal of our school (who was bald and had a pot belly) for a play once. I studied in that school for just 1.5 years and everyone still remembers me as the girl who was 'Mr.P.V.Chacko'. Even teachers who didn't teach me know me (almost 20 years later)!
1 person likes this
@SViswan (12051)
• India
18 Sep 08
Oh, he did have a good sense of humour and I'm sure he remembers me too!
I'm like your mother and would go all out for my son if I had to. The older one loves to dress up and waits for Krishna Jayanthi every year to dress up as Krishna. I prepare for it atleast a week earlier so that he has everything ready on Krishna Jayanthi.
1 person likes this
@James72 (26790)
• Australia
18 Sep 08
lol. My Mother DID put in a lot of effort and you can imagine now horrified my Father was about the whole episode! It was one of those things that we didn't discuss in public! Fame is welcome wherever we can find it! At least you will exist in the minds of many for a long time to come. Thanks for responding and I hope your Principal had a sense of humour when you did this!
Fame is welcome wherever we can find it! At least you will exist in the minds of many for a long time to come. Thanks for responding and I hope your Principal had a sense of humour when you did this!@James72 (26790)
• Australia
18 Sep 08
The colours, costumes and displays etc made for all the different festivals in India will be something I will never forget. And isn't your son just as lucky as I am to have a Mother that will go all out to turn him into a woman if the need ever arises! lol. Blessed are the few!
@mimpi1911 (25464)
• India
19 Sep 08
lol...
that's funny, I wish I could see you holding the prize in the same outfit! Yo must be a kid then and that had made things easier. I remember playing a crying kid boy in a typical rustic shorts and shirt (no slipper for me) whose only acting power is exhibited through the way he cried all through the scene. His mother, played by a little older gal, was unbelievably calm and without that. But trust me, I was so engrossed into fake crying that I missed the time I was supposed to leave the stage and even after the curtain was down I was crying there!
But James, i dint get any prize for that and neither did I felt embarrassed. It was an all girls' school. lol...
1 person likes this
@mimpi1911 (25464)
• India
19 Sep 08
yes boys task gets tougher for I feel it easier for a girl to dress up convincingly as a boy while its really tough the other way round. Boys have to go through some real anatomical changes that they find hard to accept in the first place. So, in that regard you had done an amazing job, I am sure.
1 person likes this
@mimpi1911 (25464)
• India
19 Sep 08
Teasing bit is fun James but I am glad that it dint turn out to be a hollow victory after all!
1 person likes this
@James72 (26790)
• Australia
19 Sep 08
I am trying to remember who has the photo? For sure my Mother will have it somewhere but let's hope it stays in storage for now! It sounds like you certainly gave the crying boy part everything you had! lol. Girls dressing as boys comes with far fewer consequences believe me! I am just thankful there were several hundred other guys dressed up also otherwise I would have NEVER lived it down.....
@thebohemianheart (8827)
• United States
18 Sep 08
Nope, can't top it, nor can I come up with something equally funny. But, this made me smile. It reminded me of the picture my mother has of my youngest brother, also a James, wearing a bride's maid's hat and holding the bouquet. I think I remember one of him wearing a dress for a school function as well. It always makes me smile and giggle a little when I see it.
1 person likes this
@James72 (26790)
• Australia
18 Sep 08
Is there something about "James's" and women's clothing??? Is this a conspiracy against all males with this name? I am happy that I at least managed to bring back some fond memories for ya! lol. Thanks for responding and I hope your youngest brother made it through the trauma OK!
I am happy that I at least managed to bring back some fond memories for ya! lol. Thanks for responding and I hope your youngest brother made it through the trauma OK!1 person likes this
@thebohemianheart (8827)
• United States
18 Sep 08
Trauma!? I think he enjoyed it!
1 person likes this
@SaintAnne (5453)
• United States
21 Sep 08
In high school, I once came in second in an animal obstacle course. I had to run a half kilometer to get to a goat from which I had to fill a bowl with its milk. Then another half kilometer to get to a muddy enclosure to catch a piglet. Then another half kilometer to get to a cat, put a leash on it and lead it for another half kilometer to the finish line.
Okay, I'm sorry. I made that all up. I couldn't think of any quirky or bizarre events in my life but I just had to top your achievement. Plus, I'm bored tonight with most of the other discussions.
@James72 (26790)
• Australia
21 Sep 08
Ha ha. I was starting to wonder who the poor bugger was that had to set up all these animals at half kilometre intervals! It could have been worse..... You could have said that you had to dress up AS an animal and run through an obstacle course! lol. Thanks for responding SaintAnne and I hoped you relieved your boredome even if only for a few minutes! Secondly, I think you need to get out there and do something quirky or bizarre to add to your life's CV! 
It could have been worse..... You could have said that you had to dress up AS an animal and run through an obstacle course! lol. Thanks for responding SaintAnne and I hoped you relieved your boredome even if only for a few minutes! Secondly, I think you need to get out there and do something quirky or bizarre to add to your life's CV! @SaintAnne (5453)
• United States
21 Sep 08
Ha ha! I got you, you poor little bugger. I am sure there have been some quirky/bizarre events in my life but I just can't remember them now. Maybe it's because I don't think they're quirky/bizarre enough. But you are quite right, I need to go out there. Just give me some time. Who knows, I may take a loooOOooong hiatus from myLotting while I take on the real world out there.
1 person likes this
@nengs10 (3180)
• Philippines
19 Sep 08
That's funny. Actually, that kind of competition is famous in our country during festivals and certain events. Real men dress like women. And not just that, they were all very sophisticated and on the go for the said challenge. Congratulations to you.
1 person likes this
@AndrewFreyne (6281)
• United Kingdom
21 Sep 08
Hi James, that's very interesting! Can I ask you a question? You don't still practice this fine art do you? How did you find the high heels? It just goes to show how much of a boring life I've had, I've not had any experiences to match that one! In order to have won this competition you must really have looked gorgeous! Anyway, I guess it's a good thing to do things out of the ordinary from time to time. Andrew
How did you find the high heels? It just goes to show how much of a boring life I've had, I've not had any experiences to match that one! In order to have won this competition you must really have looked gorgeous! Anyway, I guess it's a good thing to do things out of the ordinary from time to time. Andrew1 person likes this
@James72 (26790)
• Australia
21 Sep 08
Still practice? Only on the weekends Andrew..... Only on the weekends! And the high heels I wore were a pair I had been saving for just an occasion as this actually. And for the record I was BEYOND gorgeous mate; I think that stunning would be a more adequate description! lol. I think it is of benefit for all of us to get out of our comfort zones once in a while and if we can also laugh at ourselves no matter what then this is even better! Thanks for responding to the discussion.
And for the record I was BEYOND gorgeous mate; I think that stunning would be a more adequate description! lol. I think it is of benefit for all of us to get out of our comfort zones once in a while and if we can also laugh at ourselves no matter what then this is even better! Thanks for responding to the discussion.