When I met my ex wife, I had dressed up for Halloween on our second date, borrowing some of her clothes, wearing some of mine and adding a few things I bought in the Halloween isle. (before coming out to her, or anyone)
After I had come out to her (Before we were married) I decided to try to make a trial run and spend the day (Halloween) dressed as a female, and told her that I wanted to look as real as possible. I wanted people to actually believe I was a woman.
She made me up wonderfully. I had to work 2 jobs that day and people I worked with everyday thought I was a real female and did not recognize me (until, as most of us experience) I opened my mouth to talk. We all went out to a club that night after the second job and had a great time. I actually got to spend a full day, 2 jobs and a night out on the town, with eating out during lunch and a couple of stops at stores along the way, as a female. I was dressed and looked great and felt great, I was comfortable, and most of all, I FELT LIKE ME! Everything felt right more than it ever had before in my life. That, more than anything made me realize that I couldn't fight it anymore and I had to start coming out, so I did, slowly at first.
A few months later, a local radio station was having a contest....a DUDE LOOKS LIKE A LADY CONTEST. I got fixed up the same as that Halloween and went. I Won the contest and got to travel to an Aerosmith concert and got back stage to meet the band , who are a few of my lifelong musical heroes!
It wasn't long after that that I started getting the courage to go out in public dressed up on a normal day when I had no other excuse for crossdressing other than "This is me, and this is how I like to dress". It was scary at first, but didn't take long to be comfortable, the more I did it.
Halloween is a great springboard for crossdressers and all trans people.

Sometimes they would say "I would really like to do your hair and makeup like a girl one day to see how you'd look, but you probably wouldn't let me do that, would you?" I would always replay by saying "Hell. I don't care, why not, it would be a lot of fun!"
Once in a while a girl would try to make me look like a girl and it looked ridiculous. Some girls will make you look like a man that is trying to look like a woman or they give you the theatrical look like a drag queen would wear on stage, which is fine, just not the look I was after (and it's hard to tell the girls what you are after without outing yourself). But for those that did a really good job and made me look and feel really sexy, WOW! lol we had a lot of fun. If it didn't look good, I would go wash it off when we got done, but it it looked really good, I would leave it on and even go out with the makeup and hair done. Every now and then, when girls would make me up as a girl, they would ask if they could dress me up. Usually, it just ended at hair and makeup, so I loved the few times I could do this and it was their suggestion. They would fix me up and have me put on an outfit, a dress, a skirt and whatever else just so they could see their work completed with the outfit to see just how much they had pulled off making me look like a girl.
The disappointing thing about that was when I was looking really good with the hair and the makeup and the outfit all together, I was not out yet (was even in the closet to myself to an extent, but I still always knew in my heart and the back of my mind) So I would still keep the makeup and hair done and go out in public, but I would not wear a dress or skirt out in public............
...........................UNLESS IT WAS HALLOWEEN!!!!
THEN Halloween started to become really fun for me.

As I got older and grew my own long hair and was in bands, during the 80's, I could get away with wearing some feminine clothing and some makeup and have my hair done everywhere I went and no one knew I was crossdressing/transgender. lol
Of course, I was not wearing dresses or skirts, but you could wear quite a bit of feminine looking to obviously womens clothing back in the 80's and it was the "Cool Rocker Look". You could be both feminine and hard edge at the same time. (To this day I still love the 80's rock groupie look. lol) Before I ever came out as Transsexual to anyone, the 80's was such a great time for me in many ways. I was still in the closet, but I could still dress to a greater extent to that which met with my personal inner identity. Girls would always love to play with and fix up my hair. Sometimes they would want to French Braid it and was afraid I wouldn't approve of anything that feminine, but I always welcomed them to fix it in any way they wanted as long as there was nothing permanent that couldn't be put back. (Could not cut it short or give me green mowhawks, etc. lol)
Girls always would let me borrow their clothes. I wouldn't even ask them, they would just say "I think this would look great on you, why don't you wear it tonight. (Zebra Spandex, a blouse, a sexy but rocking scarf, etc.)
Girls loved to do my makeup for when I played out with the band or just going out. Sometimes they would be worried that the makeup would be too feminine and I wouldn't like it. Occasionally, I would have a girl that didn't do my makeup well, but usually, whoever was doing it did a really great job and I loved it. Quite often (once again BEFORE I came out) girls who would be doing my hair and/or makeup would bring up that they would like to make me up like a girl one day just to see how I'd look (they brought it up, not me) Of course, I always wanted to, but would try not to give it away that I wanted that more than they did.

I remember when I was a kid and trying to go dressed as a girl for Halloween and was always disappointed in the outcome. Sure, I still had fun trick or treating with my friends and brothers, but when I said I wanted to be a girl for Halloween, and though I knew in my heart I wanted to really be a girl, I had no female clothing of my own, no makeup and no knowledge of how to apply it, etc., so I was at the mercy of whatever anyone threw together on me. The few times when I was younger and went as a girl for Halloween, it was done as funny and a joke and the dresses I had to wear did not fit right and was not the kind of style I liked either, my mom had a few wigs laying around that we'd play with sometimes to be funny, but my mom never wore wigs. They looked ridiculous, but I was always given one to wear with my girl "Costume". And the makeup was never pretty.

I have a transgender friend who is an EMT and a couple of others that work in hospitals. You never know these people, who we all expect to always conduct themselves in a respectful and professional manor and put saving lives above all else, may some day find themselves in a situation where their very life may depend on that transgender EMT or hospital medical professional. How would they like it if transgender professionals were making jokes while they were laying there needing medical attention, possibly to save their life?

At a couple of jobs I would use the womens restroom when I was dressed female, but they were single restrooms and not multi-stall.
At a few gay night clubs I have used the womens room many times, but, of course, it is never an issue there and some of the restrooms there are multi-stall unisex anyway.
At the straight bar I worked in, men were not allowed in the womens room or women allowed in the mens room, but if a man was dressed as a woman, they were respected and were allowed to use the appropriate restroom, so I wasn't getting special treatment just because I worked there. lol
I usually go to LGBT Pride Night at Kings Island Amusement park in Ohio every year (which is coming up again September 10th) The first time I went there dressed as female, it was the first time it was the OFFICIAL pride night. They had pride night there for years, but it was not official, it was called "Red shirt day" because people just spread the word to be there on a certain day and if you were LGBT you wore a red shirt to identify yourself to other LGBT. So the first year that the Cinci LGBT community center bought out the park for the day and held the first official event, I went dressed as female but when it came time to use the restroom, I used the male facilities because I was not sure what the parks rules were even for that night, or if anyone had possibly educated the park staff on issues of gender identity and use of restroom facilities. So I simply decided to play it safe just in case.
The last time I went, I did use the womens restrooms as I was told that it had been discussed with the staff and security and the all clear had been given to use the restrooms that were appropriate for how you were dressed.
Most places in public, I try to use womens single restrooms as much as possible.
I have been out with my girlfriends who were going into the womens multi stall restrooms a couple of times and when I said I would wait for them outside, or would go to the "other" restroom and meet them back outside, they said "No, you're coming with us" and pulled me in with them. Surprisingly, when they have done that, most of the other women in there are not bothered by it, but I have seen a couple of women that seemed to not be comfortable with me being there as they looked nervous and made a hasty retreat. lol
That is the one big thing, other than legal issues, is that I don't want to make anyone else uncomfortable.

I have never purged, but after a while in my current situation not being able to dress for, but finally coming out to my mother and getting back into it, I found that so many of my clothes no longer fit. I had not realized how much weight I have gained in such a short time.
This is frustrating because after suspending my transition before due to my fathers poor health at the time when I had already began transitioning before, I was planning to tell my father soon and begin full time transition again by October.
Now I will either have to start building a new wardrobe or lose weight. Money is really tight right now until I can get my business to pick up full time. I need to lose weight either way, so I guess I need to start dieting (for my figure as well as my health) then figure out how to make some extra money to do some shopping. Don't get me wrong, I don't mind shopping for new clothes, I just don't want to have to get rid of my old clothes.
I don't think I could ever purge intentionally.

Halloween is definitely the best time for new crossdressers to test the waters of going out in public dressed. I had dressed female a few times in my life for Halloween, although early on it was more other people throwing things together on me to make me look more comical than convincing as a female. When I was a little older I had some girlfriends that had fixed me up really nice on Halloween and made me look much better and did good make-up and clothes that looked right and did not make me look like it was all for a joke, although those friends at that time did not know I had the desire to dress like a female all the time because I was not out and open about it at that time and was actually still repressing those feelings and in denial to a certain degree to myself as well, but I knew deep down that this is what I wanted.
On my second date with my ex-wife (but before coming out to her) we were on our way to a Halloween event and I Was scrambling to put a costume together. We stopped in a Walgreens to see what costumes and accessories they had. She had some clothes in her car and I asked her if she thought she may have a skirt and a feminine top that may fit me and if I could borrow them and she said sure, so I bought some black fishnets and the playboy bunny ears and tail, put those on with a black skirt and a white off the shoulder top that she let me borrow and just did the best I could on short notice. I won 3rd place in the costume contest that night and I didn't even have on any make-up other than eyeliner.
I did come out to her before we got married and told her I wanted to become a woman and she was awesome about it.
A couple of years later, I decided to go out as a female for halloween again. I was working 2 jobs that day, and they were both having costume contests. My ex was a model and she helped me so much with teaching me how to put on make-up and so many other things. She fixed me up really good. I went in to my first job and was amazed that people I worked with every day were not recognizing me....until I spoke. lol I turned some heads and one girl I worked with told me that her boyfriend and one of his friends were there talking to her and saw me walking past and she said they were drooling an her bf said "wow some long @$$ legs on that b!t@#. " lol We had a lot of great laughs over that! I won the costume contest at that job and then went in to my second job and won that one too. A bunch of us from my second job went out to eat and then to a couple of clubs that night and I had so much fun and my wife (ex-wife now) who already supported me completely, told me that if she wasn't already convinced that I needed to be a woman before, that night would have done it. She saw how happy I was and how much fun I had.
A few months later, I entered a "Dude Looks Like A Lady" contest and won that. I got to go backstage to meet Aerosmith at a concert in Lexington, KY. I did not go to the concert dressed up, but now I wish I would have, but I did have the band sign a picture of me dressed up for the contest.
After that, I started going out in public more as Racquel.
Halloween is a great springboard for crossdressers, but as good and free as you feel on Halloween, it does not compare to the feeling of freedom (and fear) when you go out crossdressed on any other random day of the year.

This is AWESOME! Great story.