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Dares, Bets, Dances, or Parties

16 Posts
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Posts: 5
Lady
Topic starter
(@saefire-reign)
Active Member     Michigan, United States of America
Joined: 6 years ago

A kid I used to be friends with who we'll call X needed a date to some lame winter dance his school was hosting (he and I went to different schools) this was maybe our third year in High School it's been so long though so my memory is a little fuzzy (we're both 21 now) anyway he jokingly stated that since I owed him money, I should pretend to be his date and then we'll be even. We both had a good laugh about it and went on our way but then a week later I was reminded that with the the way my funds were set up at that time, I wouldn’t of been able to pay him off properly (I had just recently funneled all of my money to get a very cheap car) Realizing I was a poor bastard and had asked for multiple extensions for the date that I owed him I called him up and asked about that whole date thing he told me he was only joking when he said that and that he didn't really want me to do that but I was able to convince him ( it was mostly me just telling him that we did not go to the same school and if I got a pretty convincing makeover nobody would even know I was a boy) he agreed to it.
I told my sister everything and she gave me an old dress she wore to one of her dances, and a wig one of her friends gave her. For makeup she called her friends and they came over to see what they could do and if they could fix me.
The day finally arrived, I lied to my parents and told them I was going to hang out with X tonight (well I was but not in the way they thought). When I got in his car I had to change. We finally arrived at his school around 8:41 p.m.
"Alright! You ready?" He said,
"One sec." I nervously replied back, he assured me that only he and I were the only ones that know I'm a guy, everybody else will think I'm a girl. Knowing I can't be having second thoughts now, especially all dolled up like I was in his car X went to open the door as I zipped myself up, grabbed my shoes, and with a deep breath, stepped out.
We walked through the hall and I noticed that with the heels I was only an inch or two shorter than him, I was also nervous that people would figure out it was me.I danced and actually had a great time. We took some photos and I ate some damn good cheesecake.
While I was at this dance with him I realized M was not some nerd he was also funny, and actually kind of cool.
At around 1:08 a.m. we decided it was time to leave I changed back into my regular clothes in the school bathroom and he drove me home.
So I'm curious, have any of you ever cross dressed and went to a prom,dance, or party? Was it intentional? If so, how did it feel? Did anyone know it was you? Did you have a date? Would you do it again? If you haven't would you ever want to?

Pics are on my profile

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15 Replies
Posts: 5
Lady
Topic starter
(@saefire-reign)
Active Member     Michigan, United States of America
Joined: 6 years ago

Pics

side by side images

my dress

 

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

I went out on Halloween one night, probably about 20 years, and 40 pounds ago. I was dressed all the way, from my blonde hair, to my 4" black peep toes. Not to brag, but I looked pretty good. I was sitting right across the table from my best friend. We were at a local bar. He was buying me drinks and, flirting with me most of the night. He had absolutely no idea that it was me, until I finally spoke. My voice is very recognizable. We still laugh about it to this day.

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Posts: 5
Lady
Topic starter
(@saefire-reign)
Active Member     Michigan, United States of America
Joined: 6 years ago

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Posts: 5
Lady
Topic starter
(@saefire-reign)
Active Member     Michigan, United States of America
Joined: 6 years ago

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

You look fabulous sweetie.

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Posts: 96
(@christiega)
Estimable Member     valdosta, Georgia, United States of America
Joined: 6 years ago

you look fabulous!

I would go to the dance with you

Hugs

Christie

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Posts: 875
(@ladymakenzie)
Noble Member     Brighton, Michigan, United States of America
Joined: 9 years ago

I'm in agreement. You are beautiful. On the other question, I have not, but I dream of enjoying such an evening with my wife at some time.

MacKenzie Alexandra

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Posts: 1781
Lady
(@ohlivialivin)
Noble Member     Norfolk, Ontario, Canada
Joined: 6 years ago

Hey Saefire. I've only been public a few times and even then it was without make-up or wig. But I'm a sucker for a dare, with some help on those items it could definately happen.

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Posts: 149
(@skyler1090)
Estimable Member     Chicago, Illinois, United States of America
Joined: 6 years ago

You looked beautiful! I was never dared or bet to go to a school dance as a girl. Secretly I always wanted to though. I was friends with a group of girls in high school and was accepted as just another girl. At dances though I was shy and went as a guy usually alone. When one of the girls dates would stand them up, I was usually the “gay/bi” best friend (I always presented as straight and have just come out as bi recently) to swing in to dance with them all night and still have a good time. This was all 10 years ago though. My how time flies

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Posts: 5
Lady
Topic starter
(@saefire-reign)
Active Member     Michigan, United States of America
Joined: 6 years ago

Thank you I felt fabulous

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Posts: 5134
Admin
(@cdheaven)
Illustrious Member
Joined: 9 years ago

You look beautiful and make great woman.

I like to dress as a woman anytime, bet or no bet.

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Posts: 1351
Ambassador
(@elbereth)
Noble Member     Northampton, Massachusetts, United States of America
Joined: 7 years ago

Hi Saefire, great story thank you for sharing it with us.  Also, great question.  This Halloween was my first time dressed and even though most everyone there saw it as me dressing as a character it had a much deeper meaning.  Could not stop smiling, though no one has commented to me since.  But to answer your question, I do look forward to the day of going out to a party dressed to the nines.

 

 

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Posts: 5134
Admin
(@cdheaven)
Illustrious Member
Joined: 9 years ago

I first started cross dressing after  a party I went to dressed as Charley's Aunt. I had on a beautiful very lacey , 116" hooped petticoat, beautiful hoopskirt and top, very lacy yellow satin pantellettes, gray wig with hanging curls, basic makeup, earrings, a broach, a string purse.

I was a hit and most persons thought that I was actually a woman!

I have had the urge to CD from an early age. But this was my first time at age 57. I certainly regretted not doing it earlier and enjoying my feminine side.

I will have to upload a copy to my public photos. It was my de but dressed as a woman.

 

 

 

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

My first outing was to a party - and so were the subsequent two outings.

Both the latter were with my wife - I selected every item for the first party, which was a Halloween party in East London.

To get there from our central London hotel meant a long tube ride, to which I was looking forward tremendously.

To my delight, the tube station next to our hotel was closed, and we had to walk half a mile across central London to the next nearest one.

The 3 inch heels were felt so natural for me to walk in, so my first time out properly in them was a total pleasure.

Got a few snotty comments from guys we oassed, but entirely admiring ones from ladies, "Nice one, mate!" was the most common.

I met a lot of ladies that my wife worked with, and have not been allowed to forget it - as if I could!

The next (and last) party was my wife's birthday party, and she chose the dress - and the name which I kept :0)

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