Adventures In Crossdressing

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.

Thursday, January 15, 2009

New Blog

I'm sorry I haven't posted in so long. I have a brand new adventure to plan but I will be starting a new blog for it. Please visit

It will be about planning my dream wedding. My girlfriend and I have been talking about marriage and she agreed it might be fun to have two ceremonies. Including one where I get to be the bride.

Saturday, March 29, 2008

Wax On, Wax Off

All I had ever heard about was how painful waxing is. They make fun of it in movies and on television, I've discussed it at bars and in private with girls who have had it done, I guess I needed to find out for myself. So on the Wednesday before my photo shoot I set up an appointment for a waxing.

Let me back up a little. Two months before my photo shoot I was researching waxing and I found an esthitician who had a private business doing waxings and that was all he did. I sent an email and he was generous enough to set up a free consultation.
He answered my questions about how long it would take, how long the hair would take to grow back, cost, and those sort of things. He explained how you need to follow the hairs growth patterns and how the movies made it look more painful than it really was for effect, he was very knowledgeable. When I asked him about the pain he said everyone is wired differently. He then did a couple of test spots on my arm, thigh and back. Little Band Aid size strips and warm wax cautioning that the wax might feel hot but wouldn't burn. A quick pull and the hair was gone. I was surprised at how easy and seemingly painless it was. So I set up an appointment the Wednesday before my photoshoot.

When I showed up he had me strip down and climb under the modesty sheet before he came back in to start the waxing. He started on my back, which I am lucky in that I don't have a lot of back hair. The wax was very warm and once he applied the strip, which was no longer the size of a band aid, it seemed about 2 inches wide and a foot long. The shoulders and upper back were no problem, I thought this was going to be a breeze. When he reached my lower back, where I had a little more hair, it started to hurt some. Sort of like touching a hot pan on the stove for a second. My back was done and I had survived, things were going along fine.

Then he started in on my legs. Now my legs are pretty hairy normally and you need to have at least 1/4 inch of hair in order to wax successfully. Again with the wax and the linen strip was applied and off it came. Ouch! It really does hurt. I will again go back to the touching a hot pan analogy but the thing with the hot pan don't keep going back for more. This kept on and on and on, then you get a little break and you realize I have another leg to go, and my arms, and then I have to turn over and do the front. It really, really hurt.

After my legs were done front and back, I was lying on my back as he moved on to work on my arms. We had been discussing all sorts of topics and I changed the subject asking if anyone had ever just said "I can't take it anymore, I quit." He said that in all the years he had been waxing people no one had ever quit on him. He asked if I wanted to quit and I said no I was just curious but deep down I wanted to know that I was at least a little braver than some one else and for sure I didn't want to be the first person to quit.

The entire process went on for about two hours. I realize now that I would not do very well in a torture situation. I do not like pain. To be fair, the esthitician was very good, the pic above is of my legs. He was a good listener and talker trying to keep your mind off the pain and moving at a good pace. He kept asking how I was faring or if we should take a break. So I bear him no ill will. It just really hurts.

My initial plan had been a waxing from the neck down, including the private bits. This, in fact, was his area of expertise. But after the two hours I had been though I was ready to call it quits. We had discussed why I had chosen to get a waxing and my crossdressing plans for Saturday, so he knew the look I was trying to achieve. In the end I settled on cleaning up the bikini area and my backside if I wanted to wear a thong. But the genitals got a late pardon from the governor.

The day after I felt and looked a little like a plucked chicken. I had little red spots where each hair had been pulled out by the roots. I put on the lotion he had given me for the next couple of days and soon enough it felt like a mild sunburn and then it was just smooth, pale skin. I didn't get hair growing back until about a week later and even then if was very light. I was able to wear stockings very comfortably for an extended period of time which is a very fun thing for me. Even now, six weeks afterwards, I have just enough growth on my arms that I can start to wear short sleeve shirts again.

Would I do it again? Maybe. When talking with the makeup artist for my shoot she said that her friend takes a valium before hand. Maybe something to help dull the pain first would help. All I know is nothing feels sexier than a pair of nylons sliding up a hairless leg. Yummy!

Wednesday, February 6, 2008

Fun With Immersion

As I prepare for my photo session in a couple of weeks I think back to my week in London in 2006 and how much fun it is to do a real photoshoot. I have played around with digital photography at home plenty of times, but there is something special about a professional photoshoot. Its nice to have someone else's perspective on things. They can give you real feedback on how a particular pose looks or if your facial expression is good or bad or if you have lipstick on your teeth. I found the number of quality photos is significantly higher. By quality photo I mean one that looks somewhat like me looking like a girl versus a guy in a dress. I highly recommend trying this if you have the means.

I have come to a point where I like trying all the fun things girls get to do when getting ready for a big night. Dressing is fun but immersion is really fun. As I was preparing for the upcoming shoot I remembered something my girlfriend asked me last Halloween. Yes, my girlfriend knows, which is cool but she is still acclimating to it. She has been very supportive and will talk issues out with me but I don't know if she wants to see me dressed or not. Short story quick, I thought it would be better to tell her early on in the relationship versus being discovered. She was happy I told her and has been great about it since I told her almost a year ago. Back to what she asked me last Halloween; "Why don't you do it for more than just one night or a couple of nights in a row?" It was a pretty good question and I decided to try a long weekend this time - morning, noon and night.

I had mentioned in a previous post that I had a waxing consultation. The esthetician tried three different test spots which allowed me to see how painful it was, how long it lasted, those kinds of things. It wasn't too painful and the irritation was minimal, so I am happy to say I have a full body wax scheduled for February 20th. That will give me three days before the shoot to get rid of the redness from the waxing. This is my first step in immersion.

Secondly, I have painted my nails before, I have had a nail technician paint my nails before, I have glued on false nails before but I have never had a full set of acrylics. Side note: My girlfriend did invite me along to a manicure pedicure with her about a month ago, it was fun but it was a manly mani-pedi for me. Back to the upcoming event. I found a salon and asked if they would be OK with a man getting a pedicure with polish and a full set of nails. I would rather people were aware of what I want going in so it is easier for me and for them. I don't like to force my hobby on anyone that isn't interested. They made sure their nail tech was OK with it and now I have an appointment scheduled for Feb 22nd. This will allow me to keep the nails for the entire weekend.

Thirdly, also in a different previous post "Fun With Hair" I talked about my coloring done at the salon. My hair isn't long enough to try that again and I am a little bored with the wigs I have. Mostly because they are small and give me a headache if I wear them for too long. So in order keep on with the immersion theme, I had a lace front wig made. If you are not familiar, this is the kind of wig that Beyonce, Tyra Banks or RuPaul would wear. It is made of human hair and is adhered to your head for days or weeks depending on how long you want to wear it. It is also sized specifically for your head. It was expensive but I am looking forward to seeing how it looks and lasts.

I also just ordered a new set of breast forms off E-Bay that are self adhering too. I don't know how they will work out, they were $100 which is pretty cheap for breast forms. I am hoping they give the right weighting on my chest. Beyond that it is just the same old, same old. Trying to find cute outfits for the photo shoot and to wear around the house all weekend. It's a tough job but somebody has to do it.

Thursday, January 3, 2008

New Year, New Plans

I have always enjoyed pinup art, the femininity the models convey is always something I wish I could achieve in my pictures. I have been lucky enough to have had an opportunity to try my hand at modeling a few times while dressed. The last time was in London in December of 2006. I am currently trying to set up another shoot sometime in February.

I was surfing around a few months back and I happend upon a web site that had photography for pinups. What's even better is that the studio is in my hometown. The concept for the studio was a burlesque dancer went to her photographer friend for some pinup photos for herself. This blossomed into a the idea that maybe there are women out there who want to have these kinds of photos for themselves. Kind of a retro/pinup Glamour Shots.

Since I thought this was this was the best idea ever, I decided to contact them. I explained my situation, no sense in surprising the photographer when you show up in drag. The dancer sets up the shot, does the makeup and those sorts of things. She e-mailed me back and said she had never worked with crossdressers before, at least in pinup photography, and said she would be glad to help.

This was two months ago and I have been waiting patiently to set up the appointment. Based on my schedule and my two times per year dressing up plan, I figured mid February was my best option. I sent off an e-mail the other day to schedule and I am now waiting for the reply.

In the last two months I have been diligently planning the shots I want to do. I will be going for the five photo's plan which will allow me to have a few different wardrobe changes. There are essentially two kinds of pinup shots. The "Oops" moment where the girl is "caught" in a situation with her delicates exposed. The other is just your basic look at me in my undies shot but tastefully done. I, of course, plan on doing both of these.

The studio web site suggests that you tweeze thos brows, shave/wax those legs and bikini area and polish those nails. All wonderful ideas as far as I am concerned. I found a waxing specialist and have set up a test appointment where I can have questions answered and have two test spots done for this upcoming Saturday. This is something I hae always wanted to try and I just might do it this time around assuming the test hair removal doesn't scare me away.

Next on my list is nails. I have had manicures before with a polish but I have never had a full acrylic set. I think this would be a perfect time to try. This also would mean having to remove them. I am going to do a little research on this but I think it can be done without issues. Since I will be having the nails done anyways I figure I might want to keep them for a few days too. My plan right now is to take a couple days off around a weekend and work from home one day. This would allow me to keep them for four or five days. I might just have to dress up for that many days. Oh, woes me!

Lastly, I have been looking for some fun retro clothing and lingerie. So far I have a dress picked out I want to buy. I also have made a purchase of an open bottom girdle and bullet bra. For one photo I plan to wear the girdle and bra with nylons and heels while I am "ironing" my dress before a big night out look.

Thats all for now, I will share more details as they come about. I might even post some pics here when I am done.

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.