A blog about the adventures or misadventures of an occassional crossdresser. Writing about why's, when's, how's or what's that I like about dressing in womens clothes.

Tuesday, December 4, 2007

Halloween 2006 - part three

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 pretty well what I would need to do and when that 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 to 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 bridesmaids 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 actually pretty 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 those features out 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 thier dresses to hang right and then it was time for me to get dressed.

I walked back to my bedroon where everything had been all laid out. I took off all my boy clothes and proceeded to dress in my lingerie with my two 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 straight 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 too. I added a few final touches, like pearls on my neck, wrist and earlobes all of which had been my moms 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 wierd 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 hardcores 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 thier 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 squeeked 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 brough a 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 frost off my windshield before I could be on my way. At the time it was cold and I felt very conspicuous but it does mae 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. As I write this I am already planning something big for February of 2007 but that is for another time.

Halloween 2007 - part 2

OK, its been a while. I freely admit that I tend to fall out of habits for long periods of time. I do the same thing with exercise, which reminds me... Anyways, back to my Halloween adventure.

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. The 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 seamtress 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 ade in China and won on EBay. After pinning 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 friends 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. (Mark is in the pic on the left, Kayla from the previous post is on the right) 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 improper. 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 bridesmaids 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 planty 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 crossdress 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.

Maybe I should post a Part Three or this will be very long and that way I get to post another picture. You won't have to wait long. I will post them both the same day.

Monday, October 1, 2007

Halloween 2006 - part 1

Two posts ago I mentioned I had purchased my first wedding dress. In honor of October and Halloween, here is the story of how I bought my second wedding dress and wore it to Halloween in front of all my friends. 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 get together every Friday during the summer. We had been 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 a 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 an 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 would 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. None of my friends know about my hobby yet random chance, with a little bit of help by me, set it up so they asked me to wear a wedding dress to Halloween.

Next entry I will finish the story - the dress arrives, alterations, a wedding party, and more.

Monday, September 24, 2007


The topic for this entry is hair. Not the good kind of hair like Debra Messing has on top of her head. I'm talking about the legs, arms, chest and belly hair that makes me look like the wolfman.

Early on in my crossdressing career I was enamored of the constrictive feel of a bra wrapped around my chest or panyhose encasing my legs. That along with the adrenalin rush from sneaking away to enjoy dressing was enough for me. Now I live alone and can dress when I want. As my crossdressing desires have evolved I have discovered an esthetic quality to it now that has become more important than just dressing alone.

I really don't like dressing now unless I am able to enjoy how much nicer stockings look and feel on a cleanly shaven leg. That has trickled over to other areas too. A bra doesn't look pretty when there are stray chest hairs poking out. A halter top dress looks gross if I have hairy underarms not to mention a forest of armhair. So I choose to get rid of it. The hair, not the halter top dress.

To reiterate, I am not public about my dressing tendancies. So in the summer, it would be very noticable if I went golfing with my buddies and I had clean shaven legs and arms. So I have taken to a seasonal shaving schedule. Right around Halloween and again in early March I am able to shave from the neck down and I enjoy a full weekend of silky soft bliss.

Here is a hint - while in the shower spread baby oil all over your clean shaven skin. Rinse it off but don't wash it off. The baby oil seals in the moisture and your skin feels like butter. I learned this from an ex-girlfriend. Yummy! One warning though, thigh high's don't work well if you do this, wear stockings and a garter belt. The elastic will slide right down your smooth legs.

Now back to the silky soft bliss. Shaving usually lasts for a couple of days before I start to see stubble. The worst part is the red bumps around those sensative areas. Stubble I can get rid of, but the bumps are there for a good week or so and I don't suggest shaving over them. This limits my dressing to a few short days twice a year. I would really like to try something a little longer lasting.

I have thought abuot getting waxed for about three years now but...someone will mention how much it hurts or I will watch The 40 Year Old Virgin waxing scene and I talk myself out of it. I still want to see for myself how bad it really is though. I am again thinking this is the year to try it. I really want more than just a couple days of stubble free legs.

I have plans on talking to a waxing technician just to get their opinion on the whole process. I already have found a salon on the web who waxes male customers. Feel free to share your stories or comments.

Tuesday, September 18, 2007

The Wedding Dress

It didn't take too long before I hit a lull and didn't write something in a while so here is another episode of Real Adventures in Crossdressing. I enjoyed writing about my hair coloring adventure and I thought I might enjoy writing about another adventure of mine. Writing helps me remember the event in more detail than just looking at the pictures. The adventure is the fun part.

I had just ordered my first wedding gown off of E-Bay. Yes I said my first. There's a little foreshadowing for another Real Adventure. When it finally arrived, I immediately had to try it on and was a little disappointed when I couldn't get the zipper to stay up. I eventually found the back hook closure at the top of the zipper and just like that, the zipper stayed in place and it fit like a dream. The bodice was off the shoulder with long sleeves, there was a full skirt with layers of soft tulle that puffed out nicely with the hoop skirt I had ordered with it.

At the time, I had been attending night classes at the local community college and had become familiar with the Japanese Gardens on campus. Since it was around Halloween when my gown arrived I naturally put two and two together and thought, "Wouldn't it be cool to have a bridal shot with such a lovely background." and I could always blame getting caught on Halloween. I decided to scout it out one Saturday evening and as I pulled into the parking lot I discovered I was not the only person with this idea. There was an actual wedding happening as I drove up. I made a mental note that Saturday afternoon/evening was not a good idea and decided I would try Sunday morning.

That Sunday I woke up at 6:00am and started to prepare for my wedding shot. After makeup and getting dressed, I loaded my car with my camera, a set of emergency male clothes, I even had a tupperware bowl with water and a washcloth if I needed a quick clean up. I put the hoop skirt in the back of my pickup and climbed into my truck. If your looking for a challenge, try to get a full length gown situated behind the wheel of your car. It's not as simple as it might sound. Every now and again I get a glimpse of what a real girls world is like. Now I know why brides rent limosines.

When I finally pulled in at 8:30 there was a single car in the parking lot but it was parked right at the Gardens. I decided I might take a few shots on the walking path from the back parking lot to the school proper. It was a nicely wooded path where I could have some privacy. Much to my disgust I found an early morning tennis match taking place and had no way of discretely donning my hoop skirt and taking my camera off to the woods without the people playing tennis seeing me.

I looped back to the Gardens and found the lone car was pulling out of the spot leaving me all alone in the lot. I pulled my vehicle into the closest spot, quickly scanned the area and hopped out. After grabbing my camera, tripod and veil, I went to the bed of my truck to get my hoop skirt from the back and slip it on. Just as I stepped into it, I saw a big pickup pull into the lot. I quickly jammed everything back in the cab, including myself in my full gown and now hoop skirt, backed up and pulled away. Remember how hard it was to fit in the cab with just the dress, now I had on a hoop skirt. Anyways, I made another loop through the back lot and back to see a construction worker setting up to do some work on the sidewalk right by the Gardens. Come On!!! Construction! On a Sunday morning!?!?

I drove back past the tennis match and out to what is affectionally known as the Back 40. This was the overflow parking lot that was way out there from the college building. I managed to set up up for about five shots, it was really windy and the sun was too high in the sky so my eyes were all squinty and the shots look over exposed. I packed up my things and returned home with a failed mission. I immediately decided to try again the following week.

That next Sunday, I woke up at 4:00am to prepare for my day. After loading up the truck with the same gear as last time, I got all dressed up and pulled out of my driveway in the pre dawn light. An uneventful drive took me to the Gardens with the sun just brightening the day and the parking lot all to myself. I took out my camera and tripod, this time I just grabbed my underskirt and veil and decided it's now or never. I left the relative safety of my truck behind me and walked the hundred yards to the entrance of the Gardens. I saw that the large wooden door was closed and I breathed a sigh of relief as I discovered the latch was not locked. I felt a little better closing the door behind me but still felt very exposed in such a public space.

I managed to step into my hoop skirt make a few adjustments and get my veil in place before I wandered the Gardens to take my photos. There were so many little places to take a great photo. There was an arching bridge leading up to a small pagoda, a long wooden bridge over the pond and a grassy little knoll with a small waterfall behind it. I managed to walk around for half an hour taking lots of photos before I decided I had pressed my luck enough for one day. I also managed to to make it back to my car without encountering a single person. All in all it was quite a fun little adventure.

Friday, August 24, 2007

Fun With Hair

I have a few fun stories about me dressing so this will be the first episode of Real Adventures In Crossdressing. This is a true account and I'm telling you up front it does not end up Penthouse Forum style so just relax and enjoy.

In March of 2005, I had been growng my hair out for sometime and decided it was time to have some fun with it. It was March after all and is was time for one of my twice a year Becky weekends. I decided I would try to convince a hairstylist to do somthing girly with my hair as a goof. I picked a tiny salon near my house and set up an appointment on a Thursday afternoon. I sat in my car for about five minutes gathering my courage and working on my story before heading in. For any closet dressers out there you are probably very familiar with this. Spending time walking past a Victorias Secret with your stomach in knots waiting for just the right time to go in. Thinking what if someone I know sees me or what if the salegirl suspects I am shopping for me. Thankfully I am a little more courageous now but its one of those I feel like I'm doing something wrong things. Anyways...

Once I gathered my courage to go in the salon the place was basically empty and I was introduced to my stylist. She was a cute little 5'3" blonde who I was guessing was in her lower 30's. She asked if I was just here for a haircut and I decided to try my luck. I told her my "story" about how my friends wife kept bugging me about my long hair and wondered when I was going to get a permamnent or something. I was going to help him drywall later that day and wanted to surprise his wife by showing up with a girls cut. She had a confused look on her face but said ok. She wanted to know if I had anything in mind and I told her she was the expert and to do what she thought best. She thought curls would be too old lady and suggested I have my hair frosted.

As I settled in she started mixing the hair color and explained the process. Never having had my hair dyed before it was interesting. We talked and I explined how I would just be getting it cut again tomorrow trying to make my backstory feasible. Eventually we just started making small talk. She asked where I lived and and where I grew up, that sort of thing. When I told her what high school I had attended she said me too. She asked what year I graduated and it turns out the random stylist I found to give me a girls haircut was in my graduating class. Exactly the kind of thing a closet crossdresser fears. Does she know my friends? Will she tell someone who knows someone I do? Luckily my graduating class was about a thousand people. We asked several did you know Tom? No? Did you know Kelly? type of questions. We had run with different crowds and didn't have any classes together.

After she had about a hundred of those little tinfoil squares in my hair and brushed every other layer in hair color she put me under the dryer for about fifteen minutes. When I was done she made a big show about the big reveal turned me away from the mirror. Of course, there was a mirror on the other wall but I need glasses to see far things anyways. I still closed my eyes wanting the surprise as much as she did. She took the foil out and turned me back towards her mirror. I was a little shocked not having been blonde before. It hadn't been styled yet but it was definately blonde.

She spent quite a bit of time putting in some product and blowdrying plenty of body into it. I paid close attention to what she was doing because I would need to do the same thing over the course of the weekend. In the end, the back and top was very full, she set aside some bangs to pull forward and curl under. The photo shows my attempt the next day to get the same style she had done at the salon. As she finished up and we walked to the front of the salon she said she was glad I agreed to the frosting. Then she said and I quote, "This way you look like a proper young lady." Which was pretty cool and funny. If only she knew how appropriate her comment was.

I did see her again at our high school reunion about five months later. The haircut never came up, she was about three sheets to the wind and my parents had just passed away. She was very kind and told me she was sorry to hear about my parents. So I hadn't seen this girl in twenty years and here I had seen her twice in five months and the first time I I asked her to make my hair look like a girls. It just goes to show you, no matter how safe you think you are being, be ready for anything.

Wednesday, August 22, 2007

Dressing Season

I am a crossdresser. I have spent the better part of my life trying to understand why I do it. To tell you the truth I really don't have a good explanation, I just know that I like it. Early on, during my teenage years, there was the thrill of doing something taboo. I would dress up in pantyhose and slips I found in my mothers dresser when my parents were out. I was always careful to put things back where I had found them. Eventually I got lazy and my hobby was discovered by my parents. That wasn't much fun but it didn't stop me from wanting to dress up.

During college and after I started to aquire my own items that I kept hidden away and would sometimes find time to enjoy my special hobby. Again, part of the alure was keeping a secret that I was sure no one else would understand. Then about ten years ago I was living in my own house with a roommate. My crossdressing evolved into something different. It was no longer about sneaking around but it became about trying to achieve a complete look. It was more than just pantyhose and slips. I started to buy dresses, wigs, makeup all to better achieve a completely female form. Eventually my roommate moved out and I could dress whenever I wanted. Sneaking about had lost its appeal.

Over the last five years I have fallen into a pretty standard pattern of dressing. In the fall, just after I start to wear long pants again, I am able to remove any extra bodyhair that I have. And I have a lot of body hair. Where I used to be able to just pull on a pair of pantyhose, now I can't stand the look or feel unless my legs have been shaved. This is why I wait until the fall to start dressing again. I am also able to remove armhair because I can just wear long sleeve shirts to cover up. This usually satisfies my desire to dress for a while and then I might shave it all off agin in March. This gives me time to grow things back to normal before Summer.

Fall is just around the corner and I find myself starting to look forward to "dressing" season. I don't know why I decided to blog about this sort of thing. Maybe you are interested, maybe not, maybe its not about you reading it but more about me writing about it. I might write about the things I plan to do this year or things I have done in the past. Who knows, I might just write about sports if thats what I feel like. All I know is that I am a seasonal crossdresser and fall is coming up fast.