My first crossdressing Experience was on Halloween or Brandie's awakening

 I worked at a small retail store and they encouraged their employees to dress up for halloween. My store had 6 employees all women and I was the only guy. The employees came up with a group costume of pimp and hoe with me being the pimp. My reaction was why do you all get to have the fun? What if I wanted to be a hooker? To my surprise they said ok you can be a hooker also. So on my next day off I told my mother about my halloween plans at work. She said oh I got a dress you can use, she then gave me a red leopard print dress with slits up to the hips on both sides and a pair of black thigh high boots. I found a belt at a thrift store that said BAD GIRL and I also picked up a pair of black opaque tights. When I tried everything on I didn’t like what I saw, mainly my gut sticking out the tight dress. I showed my mom and she said I looked good. I showed her my gut problem and she said I got something for that. She brought me a one piece body suit with a built in bra and said here this will suck it in and give you a set of breasts. Halloween day I got up early to get dressed I combed out my hair. I did not need a wig, my hair was shoulder length and I was an avid hiker at the time. The sun lightened my hair  So I had shoulder length red hair with blond streaks in it. The night before I made pudding and poured them into water balloons so I could have breasts. I went to put on the body suit then noticed it was a thong back suit. After getting in the body suit I added the balloon breast with the knott of the balloons facing forward to simulate nips. I then slid my legs into the black opaque tights. Then came the black pvc thigh high boots looking down at my legs seeing them encased in black pvc and how accentuated my leg. I added eye makeup and a pair of girl sunglasses. I grabbed a purse for my things then I was off to work. Before I left my parents wanted a few pics of me, with my dads motorcycles. When I got to work I was hit on as soon as I was getting out of the car.Who could blame him though he saw a hot blond pulling up in a bright red 68 mustang wearing a sexy outfit. When I got out I heard “Hey there nice Mustang you know what they say great curves never go out of style.” I looked at him with a smile and in my male voice I said “I agree”. His reaction was “Ummmm is that a 65,66 ?” all while stuttering. I laughed and said it's ok man it's halloween. When I walked into work my boss was waiting on a customer and she lost her train of thought. She told the customer I'm sorry I got distracted when I saw him. The customer turned to look and said wait, is that a guy?? All day I got hit on by men and women. I also got a few numbers. I was invited to do drag shows at a local club. A friend told me if you were gay and dressed like that more often you would have guys chasing you. I walked by a couple and I heard the guy say to his girl “Why don't you dress like that for me?” she said back to him ”If I had legs like that I would.” Another guy said to me “I had to see you for myself, That was my son hitting on you when you were getting out of your car. He said he didn't know you were a guy until you spoke. He was right you do make a good looking woman.” I got a phone call from a former worker who asked me what I was doing. I said working she said” Im at the grocery store and over heard some people saying you have to go to the dollar store and see the hot as f#@k trannie. I knew you were the trannie.” The grocery store was on the other side of town. That was how my day went. I was being hit on and my boots got filled up with numbers. I even had pictures taken with me and of me. When I got off work a friend of mine pulled up and said get in I want to take you to see my mom. So I saw her family and then her girlfriend's family. All had great reactions. Her mom has an 8x10 of me in her living room to this day. One of the cashiers at work was flirty with me that day she told me the next day she and her friends thought I was hot. She was into guys that crossdress.