I haven’t written anything here for a long time now. That’s half because I haven’t had time, and half because I haven’t dressed in about eight months now anyway. That is, until last Tuesday, when I had the most fantastic evening of my life crossdressed. Before any dirty minded readers get all excited expecting some kind of sex related story, let me warn you. It’s not going to happen. I’m an innocent. I enjoying getting dressed as a girl and I want to try to pass as a girl in normal everyday situations. When I can do that, that’s what I class as a good time. That kind of thing is a dream for me.
I knew for the past month that this day was coming because I knew for the first time in a long time I’d be able to take the time to do it and I could afford to do it. I bought myself a new dress and a pair of boots. I bought the boots because the heel is relatively flat, and I don’t want to appear any taller than I already am. It’s hard enough to pass as it is without making it harder. I think the boots are cool though anyway and are stylish. The dress I bought is a short purple and black kind of stretch dress. I liked it when I saw it, and I thought it might be good for my figure because the colours give the illusion of narrow waist and wide hips. Also I think the effect of the purple coming up near my shoulders might make them appear smaller. The only problem I have with it is that it’s not A line, or the skirt doesn’t flare out at all, and that really helps to hide the masculine figure. I took a chance on it anyway.
Tuesday morning I got up and went looking up eyeshadow videos online, because I’m never happy with how my eyes come out. I have three problems in the eye area, 1. eyebrows are too thick and can’t thin them all that much (although I do as much as I can get away with), 2. my eyes are kind of deep set, 3. My eyebrows are hooded a bit. It’s hard to do good eyeshadow on eyes like that. I found a few great videos on deep eyes, and on hooded eyes though and I did my eyeshadow a couple of times that morning to practice. It’s the first time I ever gave it such patience!. Then I looked up how to walk as a girl. I’ve done all this stuff before, but I wanted to improve it and I was never very good at it anyway. Again I found some good tips and practiced that for a while in the kitchen still in my pajamas and boots! I had planned to leave the house early and get a good day at it, but I kept getting interrupted by visitors and phonecalls. Eventually I got to have my shower and a good shave, which turned out to be a bad shave because I bled so bad. I can’t leave the house dressed because I could meet my neighbours, but I did get to do a couple of things.
I wanted to do my eyeshadow before leaving, so I could do it with a proper mirror and light. I could leave the house and drive with sunglasses on so at least that wouldn’t be noticed. I got dressed then in
- Black poloneck
- New black and purple dress
- Purple flowy cardigan
- Black leggings
- Black boots
I also fashioned a homemade gaff (for keeping male parts in place) out of a tesco’s bag! I thought of it one night in bed and wanted to try it. It’s very rough and ready, but it was perfect. Monday night I spent about two hours cutting and stitching to get it right. I made it because I’m always a bit concerned about things not staying in place and stuff. Usually when I go out I wear at least two pairs of knickers and one is a control panty. Last time I was out for example I wore two pairs of knickers, then leggings, then another control panty over that to keep things in place. Even with that, when I drive around and walk a bit I still have to tighten things up every now and again and I’m always a bit concerned about how it looks etc. This thing I made turned out way better than I expected. Those panties being worn in triplicate like that get very uncomfortable after a while and I do be dying to take them off at the end of the night. My hope made gaff was lovely and comfortable, cosy even! It keep things perfectly in place with no hope of moving and I could walk around in confidence and not have to think about anything showing in any way. I really was delighted with it.
After I was dressed I put on my eyeshadow, checked my outfit to see if I was happy with it. It was really only an experiment with it, but I was delighted when I saw it. I didn’t want to change it at all. Then I put on my sunglasses and put on a jacket and track suit pants over my girl clothes and walked out to the car and headed off. By the way I was delighted with my eyeshadow too. It turned out better than it ever had before. I couldn’t get over how good it looked. I drove to a quiet car park and continued my makeup, then some people came and I had to move on. I did that a few times before I was finished it. Thats the problem with that, it’s very hard to put on makeup in comfort.
I drove to a town about an hour away, and parked my car. Usually when I go out I’m always waiting until no one is around so I can build my confidence a bit, them I’m looking around all the time and afraid of getting caught or being attacked or whatever. This time I decided to just be confident and practice my walk in a public enough area. Doing the walk with my new tips felt wonderful. I felt twenty times more feminine than I ever did before. Not only did I feel my walk looked right, it actually felt good and feminine to walk that way. I discovered I had to feel like a girl to walk like a girl, but then walking like a girl made me feel even more like a girl. Let me tell you, that was intoxicating to feel that way.
I’ll finish up now by giving you the highlights of the night
- Parked on main street and walked about fifty yards, then took a chance and went into a hotel. No one batted an eyelid. The just didn’t take a second glance. If they did they might have noticed but they didn’t. I looked in every mirror I could find and loved looking at myself. Then went looking for the ladies which was even more exciting because I had to go upstairs. When I was going up I met a woman coming down and she just smiled at me. Heaven! Then went back to car.
- Parked further down and went into another quieter hotel. Was looking at the menu outside when an oldish man came out and told me the food was very good. He was out for a smoke and chatted me for about ten minutes. I don’t know if he read me but he gave no signs that he did. I was feeling braver now so walked down the street about 300 yards to another hotel. Had to walk past loads of people and some of them young but got no reactions at all. Didn’t go into this hotel. Was walking past video store on way back and staff were outside. All of them were young and I was sure they’d notice and laugh but none of them did. Then walked to a large supermarket and just walked in the door to see if anyone would notice me. People looked but no body seemed to notice I wasn’t a girl. I thought this was amazing so I went in and browsed around for ages.
- Then I drove out the road to another hotel complex. I went in there and went to the ladies and walked around for ages. I was looking in a mirror doing my hair and a man stood staring at me with a suspiscious look on his face so I think he read me but I didn’t care.
- I left there and drove around for a bit, then parked again. I got out of my car and walked about a hundred yards down the street when I realised I had just walked past a car and two people I knew were in it. I couldn’t go back to my own car because I was afraid they’d recognise me. I was trapped until they left. This was very exciting. I knew now I might as well just walk further, so I walked for ages, past loads of people. It felt so wonderful to be walking and feeling like a girl. Then I saw a quiet little Indian restaurant so I took a chance and went in and ordered food. I was the only one there which I was glad of. I don’t know if the guy read me. He was Indian and called me ‘sir’ but I don’t know if that was just his grasp of the language because other than that he was really really nice to me all evening. (Before you say it I don’t think he was gay either!) His friend came in then who was Irish and was chatting. He just said Hello to me as if I was a girl and didn’t look twice after that. That felt wonderful and the walk back to the car again was so much fun.
- Then I went to Tesco which felt like my biggest challenge of the evening because I knew it’d be bright and there was a long walk through the shopping centre to get to it. Also I knew it’d be busy. I walked right in and wandered around for ages with no problems. Then I saw two young girls (early twenties at the most) walking toward me. Normally I’d avoid these because I was certain I’d be read, but this time I wanted them to. I wanted to see what they’d do. The walked past me and around the corner and burst out laughing. I went back to them and said (in a friendly tone) “Do ye not like my outfit”. They said they thought it was amazing and they were shocked and they were saying how I had a better figure than most girls they knew and they kept asking how I got such an amazing body. They asked if my breasts were real (they’re not), so I told them to touch them and find out. They got a real giggle out of doing that. I stood there chatting them for ages (in my male voice, all pretences dropped) and felt wonderful. It was so relaxing and the best fun I’ve had for ages. Standing so close to two pretty girls and dressed like them, it was just wonderful.
- When I was on the way home then I stopped in a little town and there was a couple of quiet pubs. I went into one and there was an old couple drinking and watching tv and a young guy behind the bar. I asked the young guy (in my male voice for fun) if I could use the toilet. He said no problem, so I went through and admired myself in the mirror for a while, wondering what he was thinking outside. Then I went back out and ordered a coffee and sat there and drank it in the company of the others. Felt so wonderful. Felt so special and so normal at the same time.
So that’s it, more or less, the story of the most exciting and best time I ever had crossdressed. It makes me feel warm in my heart to think of it I absolutely loved every minute of it.
I’ll post pics from the night on flickr. The pics didn’t come out great though. I thought my makeup was the best it ever was that night, but the pictures make my face look all angular and masculine.