My Halloween As A Bride

Here is the story of how I bought my second wedding dress, yes second, and wore it to Halloween in front of all my friends who do not know I am a crossdresser. Some names have been changed to protect the innocent.

Back in late July of 2006 I was at a bar with some of my friends, we had been getting together every Friday during the summer. We were discussing an upcoming trip to Las Vegas the following March. Sharon and I were discussing the likelihood of Kayla actually showing up for the Vegas trip. You see, Kayla was currently pregnant and would be delivering in January. Sharon said it was too early after giving birth and that would keep Kayla from wanting to go to Vegas. I argued it was her second baby and she would be ready for some party time after nine months of pregnancy and two months of dealing with a newborn.

Since it was an argument about Las Vegas I thought it would be a good thing to make a bet; we would know in March what the correct answer was. Sharon agreed and we spent some time trying to come up with a good bet. Paying for drinks, paying for dinner, making the other sing karaoke, having to eat brussel sprouts, all sorts of options were discussed. Later in the evening Sharon said she wanted to do something that would really embarrass me, something like I would have to wear a wedding dress on the town one night. I just laughed it off but the wheels were turning. A couple of minutes later I said OK, I will do that, if you will wear a gorilla suit if you lose. She thought about it, agreed and we shook hands. Sadly, I felt I was about ninety-eight percent sure I was right.

To be honest, I’d be happy to wear a wedding dress in Vegas but it was nothing I was looking to accomplish in my life and I would rather see Sharon in a gorilla suit. The next day I e-mailed Kayla asking if she was really sure she would be going to Vegas. She assured me that she was and I made sure to hint that there would be repercussions for me if she didn't show up. I had been fishing for her to ask what they were but no luck she just replied she was definitely in. One last thank you stating that I really didn't want to end up walking around Vegas in a wedding dress and the e-mail stream stopped. I figured that was the end of that.

The next Friday at the bar Kayla was there and things were going along just like every other week. Then out of the blue Kayla changes topics and asks what I am going to be for Halloween. In my mind I am thinking "Jackpot!" but I decide to slow play it and say "I have a couple of ideas, maybe Mr. Peanut, why?" Kayla finally came through and suggested that I go as a bride for Halloween. This is perfect for me, someone else suggesting I crossdress for Halloween. Still trying to sound not too excited about the idea, I tell the table that's what I thought I was trying to avoid in Vegas. A little more conversation and a couple of "great idea" comments from the peanut gallery and I left it at saying "We'll see." Of course my mind was already made up. How can any self respecting crossdresser not jump at the opportunity.

A little searching on E-Bay and I found a fantastic deal. There are some shops in China that make knock off designer wedding gowns custom sized. When I say custom sized I don't mean size 14 or size 16. They want your bust, armhole, waist, length of your leg, everything including your height. I'm 6'4", My height is a big issue when wearing a dress. The really cool part was I found one that had no reserve and the current bid was twenty-five dollars. I bid it up to twenty-six dollars and two days later no one else had bid. I won a custom sized wedding dress for twenty-six dollars. I will be honest here, they charge a lot for shipping in order to make up the cost. The dealer I found was good because they posted the shipping right on the items description page. My total cost was still under a hundred bucks. I have tried other times to buy from China and have had them try to charge me two hundred in shipping. I threatened to report them to E-Bay and the purchase was canceled. So be careful.

After I had won the item, I sent Kayla an e-mail explaining the whole E-Bay story and she thought it was very funny. So through random chance with just a little bit of sneakiness by me, it worked out that someone else asked me to wear a wedding dress to Halloween.

About a month before Halloween the dress arrived. I was giddy with excitement as I opened the package and pulled out what appeared to be a very well made dress. I noticed the fabric was very heavy and as I found the back zipper it looked by sight like it might just fit. I quickly undressed down to my boxers and stepped into my wedding dress for the first time. I soon discovered that measurements via e-mail are not as accurate as one would hope. The dress fit fantastic from the waist down but I clearly needed some help in the bust area. It was a strapless dress so pretty much had to fit right upstairs. I made a second attempt with a bustier and some padding but it was clear that the dress was just too big.

I found a few alteration shops and called, left voicemails, sent e-mails, explaining my situation and didn't have much luck. Finally, I found a seamstress who was willing to help me out. If you've never had alterations done to a wedding dress before, they can be pricey. She quoted me about $200 over the phone and I was a little shocked. I said I would think about it and eventually my desire to be a bride won out and I scheduled a visit. She was impressed with the quality of the dress considering it was made in China and won on EBay. After pinning it up in the back she said it would be ready a week before the party. She even talked me into adding a bustle so I wouldn't have to carry around the train all night long. I'm quite grateful she did too.

Still one month before the party and just before the dress arrived, I thought I would try to disguise my intentions a little better. I called my friend Mark who I thought would be brave enough to be a bridesmaid. Once I had him on the team I enlisted the help of another friend’s wife, Angie, to convince her husband Art to join in the fun. We all got together and with Angie's help picked out the bridesmaid dresses. We found a website that had pretty inexpensive dresses and while I wanted them to go with the red, they were a little shy and picked out black. The dresses were halter top so adjusting the size would not be an issue. Shoes were left to my bridesmaids. I let them know I was planning on going all out but again they were timid and claimed they didn't want to outshine the bride.

After my bridesmaids were settled on, there was more planning for my special night. I found a cute white satin shoe that had a two inch heel. I would be on my feet most of the night and didn't want to tire out. I also ordered up some new lingerie: a new white bustier as the dress was strapless, new panties and white stay up stockings. I toyed with the idea of garters but the dress was mermaid style so it was tight on the thighs and I didn't want to appear too slutty. I also called a couple of makeup artists both of whom were willing to hire their services to me but I went with the one with a more professional web site. We met once before the party so I could explain what I was looking for and she was up for the job. The best part was she would come to my house to do my makeup.

About one week before the party I went to pick up my altered dress. When I tried it on it fit like a glove, a good seamstress is a wonderful thing. Lisa had done an amazing job that was well worth the money, she even posed for a couple of pics with me in the dress, without any makeup of course. 

Finally, it was party weekend. That Friday before work I sent an e-mail to my bridesmaid’s wives that if they wanted to see the transformation they were welcome to show up at 3:00 on Saturday. They are part time stay at home moms and have a little bit of free time. Friday night I went about removing any excess body hair. Let me tell you, I have plenty of extra hair, I spent the better part of an hour using clippers just getting ready to shave. I also had a hair issue to work on. I had been growing my hair out for some time, not long enough to get a girls style but long enough that I could use hair clip-ons instead of a full wig. I'm sure any crossdresser knows how hot a wig can get. The problem was that the clip-ons were darker than my hair, they were almost black and I have brown hair. So I tried a temporary hair dye which worked out ok but was very, very messy.

The morning of the party I was quite nervous, soon enough I would be crossdressing as a bride in front of all my friends. I had planned what I would need to do and when I needed to do it for the whole day. I spent the morning shaving my arms, underarms, chest, legs, and trimming up my bikini area. I knew no one would see anything too revealing but I wanted to play the part well. After a light lunch I was off to the nail salon. I didn't go overboard and get a full set but I had been growing my nails out a little and asked for a french tip look. I did get a couple of weird looks from other nail salon patrons, but it was Halloween. It took longer than I had expected and only had 45 minutes before Angela would be there to do my makeup. I did get a little overzealous with my razor and nicked up my face a little just as Angela arrived. That wasn't too big of a deal though as there was plenty to do. About fifteen minutes after Angela showed up Zoey stopped by with a camera. Zoey was one of my bridesmaid’s wives that I had e-mailed on Friday. I didn't know she would even be there but was glad she did stop by to take pics for me.

For the next ninety minutes Angela worked her magic. Concealer, makeup, eye shadow, eye liner, mascara, blush, lip liner, lipstick everything in her arsenal. I will admit that the makeup I had done on my London trip was better but they had experience with crossdressers. Nevertheless, Angela did a very nice job. Zoey kept taking pictures when I reminded her, she was enthralled with the whole process. She kept saying thing like wow, you have really great cheekbones or your lashes are so long. I'm sure the makeup is what brought out those features but it was fun to hear those things. Angela spent quite a bit of time on my hair getting the clips in to blend well and creating a fun updo. Eventually Zoey had to go collect her kids from daycare and Angela had done all she could. I did get a couple of pics with Angela and quick put on the dress so she could see the final product.

I had to wait about forty minutes for my bridemaids to arrive and they thought the makeup was very funny with me in boy clothes but well done. They didn't do any makeup at all, had pretty cheesy wigs and Mark didn't even shave his goatee but I was grateful I had a little support via a group costume. They spent a little time getting their dresses to hang right and then it was time for me to get dressed.

I walked back to my bedroom where everything had been all laid out. I took off all my boy clothes and proceeded to dress in my lingerie with my two male friends just down the hall. First I stepped into the panties and drew them up my legs. I hooked the bustier around my front and shifted it around my torso until the cups were properly positioned and slipped in a couple of fillers for the cups. I sat on the edge of my bed and took out the brand new pair of stockings and slid them up my freshly shaved legs, the elastic holding firm against my thighs as a slipped a garter with a blue bow up my right leg. I slid my foot into the white satin bridal shoes and took a quick glance in the mirror. So far, so good. As I stepped into the dress I enjoyed the sound of silk on nylon swishing over my legs and torso before zipping the gown into place. It fit perfectly. The square bustline filled out well but didn't gap, the waist was tight, the dress allowed for me to sit and walk but showed off my hips and legs well, like the mermaid design was supposed to do. I added a few final touches, like pearls on my neck, wrist and earlobes all of which had been my mom’s which I kept after she passed away.

I opened the door to my bedroom and walked out to meet my friends, the swish, swish of each footstep was very loud announcing my feminine garb. Art and Mark both greeted me without laughter but with wow's and a very nice. I love Halloween!

Just as we were getting ready to leave Zoey called and asked if I had a veil. I said I didn't and I was afraid of covering up Angela's work. Zoey said she would lend me her veil which clipped on the back of your head. It was official, that made for old, new, borrowed and blue. We all drove over to Mark and Zoey's where their three kids saw me and their father wearing dresses. The babysitter was also impressed with the lengths at which I was willing to go for Halloween. Zoey clipped the veil in place and I was off to the party.

The party was a fun as always. I got some weird looks and some praise. I was surprised that I received more weird looks from girls than from the guys. My favorite part was when Kayla saw me passing by her and caught my profile. She said, "Wow, who knew you were so slim." What a lovely thing to say to a bride. After midnight, most of the partygoers had left and only the hardcore players stayed on for a little game we play involving passing a bottle of vodka around. By the end of the bottle I was in no shape to drive so I stayed the night at the hosts along with a few others. After taking off my makeup, so as not to leave an imprint of my face their pillows I slipped out of my dress and climbed into the spare bed.

The next morning I must have looked like a wreck with no makeup, tons of hair spray holding some curls in place but the rest of my hairdo unclipped from my head. I didn't bring a change of clothes so it was back on with the dress and upstairs. Kayla and Ted's house was very old and each step squeaked as I walk up the steps, the dress swishing louder than ever in my lightly hungover state. I had planned on sneaking out but Kayla heard me, which isn't too hard to believe if you had heard the dress, and let me out. That night had brought a hard frost and the morning was bright with frost reflecting off of every tree and blade of grass. I had to walk in just the dress about three houses down and scrape the ice off my windshield before I could be on my way. At the time it was cold and I felt very conspicuous but it does make for a great story whenever I get to tell it. The girls just love the morning after story.

So that is my great Halloween adventure for 2006. I have done so much more since then but it was fun being able to dress up and have fun with my friends who have no idea I have a secret other life. I also took some funny photos a few days after the party to send to my friends letting them know the money I spent was not wasteful.  I could wear the dress when working around the house.