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Out Of The Blue

So it was 2002, my wife says "Why don't you dress like a woman?" I was like "What? No way". She says, "Yeah it is Halloween". We had plans to go to a friends costume party, and I hate spending money on a costume that I am going to wear once, so we were looking for ideas.

I agreed to it, with her not knowing that I actually am a closet crossdresser and had been dressing as a female since I was 12 years old (more so between 1989 and 1999 which was prior to marriage).

She picked out an outfitof hers for me, a hot pink leather skirt, a black corset, black stockings and hot pink sandals. She and I wore the same size at the time (size 12, though I used to be a 6/7).

After a shower, she put the corset on for me, I did not want to give her the idea that I knew how to lace a corset alone, so I had her do it. As she tightened it, I told her "It can be tighter" so she continued to tight, until she couldn't anymore. She says "Are you sure you can breathe?" I said "Yes, it is fine". My waist had been taken from a 32 to a 26 and probably could have been taken in more. I gained weight, but it was fat... LOL

I had her put on my stockings. I did not like the way my legs looked with hair on them, so I told her I would trim. I grabbed clippers and shaved them down to wear it looked like they were smooth under nylons. I then put on the matching g-string. She had me look in the mirror saying "This is what you would like like as a woman". I laughed, saying "wierd huh?" But I could have done better in my past. She was jealous because with a tight corset, I had an hourglass shape, something she never has had.

I put on the skirt and it was a little loose because my waist was smaller than anticipated, so she got me a wide stretch belt to put over it. She sat me down and did my make-up. She almost was going to make me look like a drag queen (which I hate that look) and Isaid, just make it subtle, so she did my eyes in pink, I had black eyeliner, she applied some false lashes, and did mascara. After finished with my eyes, she matched my lips with the skirt color, applying my liner first and filling in my lips with a hot pink lipstick.

Lastly, it was shoes. She has a pair of 4" hot pink sandals that matched the skirt, though she wears a size 8 1/2 and in women shoes, I wear an 11. I was able to get them on, but hate that my foot hung over the ends in both directions. My wife, hates heels, and even in smaller heels, she noticed I had no problem walking in them. I just said since I was an athlete growing up, I guess it was natural for me... hahaha My wife hates heels, despite having 40 pairs (I think I have bought all for her), so I didn't mind wearing them because if she won't I will... I have many of the same heels she does, in storage, because I love them.

After she completed the look with some bracelets, she teased my hair and put on a choker. I had a skater do at the time, shaved underneath and all one length down to my mouth when wet. Teased, it looked very similar to Victoria Beckhams hair so it was passable as a short haired woman look. She loved the way I looked and this is when she said to me, "I have always been curious to be with a woman". I loved hearing that, 1. because I thought this would open doors for me to dress how I am comfortable with her at times and 2. Because I would love for my wife to be with a woman.

We went to the party, no one knew it was me. I was passable as a woman. She went as a sexy woman also, so really, we went as a lesbian prostitute couple... Hahaha... It was my friends, and she had only known them or met them like 5-10 times, so we stayed off to the side, talking to a good friend of mine at times, who knew the who we were, but most kept asking from what we heard, "who are the sexy chicks".

I want to do this again, only the next time, dressing myself, and wearing clothes and heels that fit me...
garterbeltgirl19 garterbeltgirl19 36-40, M 3 Responses Jul 10, 2011

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What a great story. Too bad your plans fell through for the next Halloween. It's great your wife did your makeup and hair.

Yeah, last Halloween it was to be fun, but when my wife drinks she gets emotional... I have since came out to her that I am a crossdresser, and have since I was 12, she is completely supportive and has even bought me clothes... She has a few pounds to lose, but she looks forward to the day that we can share a wardrobe (her words not mine haha)

Sounds like you have a wonderful wife. Help encourage her on exercise and diet. Maybe you'll be going shopping together and can write another story.

Excellent, Anything happen after that? do tell!<br />
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I asked my wife if I could this halloween and at first she was for it but then backed out. I SOOOOOOO wanted to, I was quite bummed out.

Yeah it was a good night... I have since came out to her that I am a crossdresser and she is completely supportive and loves me as a she...

YES! What fun. I dressed up as a woman once for Halloween - with clothes I bought for myself! A satin bridesmaid dress (10 bucks at a second-hand store), lingerie and hose, plus pumps I got at a cut-rate shoe store. I bought a wig at a costume shop. I did my own makeup too and even applied some sweet perfume. It was so fun and I got a lot of attention.