I know its alittle rough, I'll clean it up and add in some parts over time.

I got into an arguemet with my girlfriend and her friends, about which sex is the hardest to be. They said a man wouldn't last night as a woman, and I said he would. The arguement continued on for some time, then one of her friends suggested that I try being a woman for a night. Of course I said for the right amount of money I would do it for Halloween. They decided they would give me $100 if I did it for the whole night and another $150 if no one discovered I was a man. There is one condition for the $150 to get it I have to get dressed and ready to go out as a woman by my self with no help from them. I have a small frame so size wize I can pass for a woman, but other than that I need some advice and help on things I should do and need to do to pass as a woman.

I need advice on everything, Clothes, underwear, makeup, perfume, acessories, and everythng I need to do to make my self look more like a woman.

I have a small body so I look small enough to be a girl, but need to add some curves any ideas?
I need a full discribtion on how to put on make up, never done it before...
I need to know how to walk in heels, and how to walk and sit like a girl.
Also if anyone could post links to stores that have online sites to show me what kind of clothes to wear.
And I am commited to shave my legs, arms and armpits.

I did some shopping today, I got a shirt, skirt, and a bra and a pair of panties, Everything fits good. I tried it all on today, to see if I had any problems, so i have time to adjust. I am just having a little bit of trouble sitting in a skirt, I have a habit of sitting with my legs spread a part. I am learning to keep my knees together, I can cross my legs but it is really uncomfortable. Wearing a bra is something to get used to too.

Being a girl wasn't that hard, it is alot more prep work though. The hardest part was being a man, trying to pass as a girl with out getting noticed.

The whole night was a great experience, first we went for super. I found out the hard way, that it is really really cold wearing a skirt in october. The enterence to the resturant was kind of crowded, we had to walk through quite a few people. I was paying too much attention to keeping my balance in my heels that I forgot about my boobs. I ended up getting elbowed in the boob by a guy, I knew that when my girlfriend gets hit there she says it hurts, so I played it out alittle.

When we left we had to cross the street, I went to step up on to the side walk, and didn't notice the storm drain there. My heel got stuck in the drain and I fell down. Everyone on the side walk got a look up my skirt, good thing it was dark.

Next we went to a bar lounge, keeping my legs crossed or together was my biggest problem there. Also you don't notice how much guys stare at boobs untill their staring at yours. Other than that the rest of the night went pretty smoothly.

Long story short, I got the 250 dollars, but since my girlfriend was so nice through all this, I took her out for super to a great resturant a few days later.

I gained alot of respect for my girlfriend though, getting ready takes alot of time. And a bra is one of the most uncomfortable things I've ever worn, and hard to put on.

This was a lot of work though. I spent two weeks learning how to walk in heels and wear a skirt. And I dressed up the last four days before halloween, and spent the whole night as a girl practicing. In total I spent five nights as a girl, the day after halloween it felt weird not having boobs. In the end I learnt alot, and it really opened my eyes as to how much work a girl goes through just to get ready for a night. I will never tell my girlfreiend to hurry up again. Also I found the attention and staring from guys to be very uncomfortable, I kept thinking to my self "I'm only a b cup how much is there to look at?"

I worked late a couple of nights ago, and well I was gone she went to work changing out all my clothes, shoes and stuff to hers and her friends. I didn't notice tell I got up and opened my underwear drawer to find it full of bras and panites, and after going through all my other drawers I noticed that every thing had been switched out to girls clothes. They even snuck in a took the clothes that I wore the night before, that were beside my bed. next I went to take a shower and found my bathroom full of every thing you would expect too find in a girls bathroom, again all my stuff was gone. I had to go outside and grab my cell and some other stuff from work from my truck. I got to the door and noticed that all my shoes where replaced with 3 inch spicked heals. Then seen the last shock , My jacket was replaced with my girlfiends, which is hot pink. Then I looked out in horror as my street as full of people, as it usaully is on a week day.
I knew that I couldn't go out side with my girl firends jacket and heels on, with out getting noticed. I thought of waiting until some of the people left, but I needed to get that stuff asap. So I went back to my room found a pair of jeans that fit, and quickly but my wig and alittle bit of make up on. Put on the jacket and the heals and went out to grab my stuff, no one noticed anything weird, except my neighboor might thing I'm cheating on my girlfriend.

But I got the last laugh, when my girlfriend came over later to see what I did, to see me sitting on the coach watching tv, still wearing what I wore earilier. The look on her face was priceless. We both had a good laugh.

But I did what I had to do, I didn't have anyother clothes to wear.

To be honest, I miss my boobs, although I didn't like wearing a bra my girlfriend said that I would get used to it.

Over the last couple of weeks my bra has gotten tighter, and was obviously too small. I can't just go my local lingerie store to be fitted, so I searched online and found a website that you enter in your measurements and it calculates your bra size. Turns out I need to increase my cup size, I am now a B34. My new bra's fit good and are very comfortable, even the ones that I had before that I bought again in my new size.

But as some of you know it was just one night out, the days after halloween my girlfriend realized she liked my shaved legs and how much of a thrill it was when she unclasped the bra I was waring on halloween. from then on me dressing up a girl became a spark in our relationship. We became closer and closer as she taught me how to be a girl. Last december she asked me if I would grow boobs for her as her christmas present, after she showed me how I would do this I agreed to... After all what guy wouldn't want his own boobs? She had planned to give me my first bra for christmas, but my I got breast buds on december 20th, a few days to early. So she gave me my present early a baby blue training bra, that allowed me to sleep comfortably and protect my new boobs.
Over the last year I've gone from flat chested to a large B/ small C cup, from a son to a daughter, from a brother to a sister, and from a boyfriend to a girlfriend I'm everything you expect a 21 year old girl to be.

It was easier for me then for most people in my position, mother's will usually accepted it, a father rarely does and it takes time. My father passed away when I was young, but I think he would have accepted me, but probably not as fast as my Mom did.

The first time my Mom found out was at Christmas last year, I live about five hours from my Mom's place, so I only make about five or so trips a year. My girl friend and I got to the door my Mom welcomed as as always, then as she looked up and noticed I was wearing a wig and makeup, she raised an eyebrow and asked how the drive was and carried on with normal conversation. Then I went to take my jacket off and she noticed my boobs for the first time, although they were still breast buds, they were noticeable and so was my training bra (Why can't they make them more like t-shirt bras?) This sparked alittle conversation about what was going on and my plans to start living as a woman, after that my Mom treated me normally for the rest of the visit.

The nest time I went to visit my Mom was for her birthday in late february. She continued too treat me just like see did at christmas, but near the end of my visit. She said that somethings been bugging her for the last while and asked me to take of my shirt. I giggle and said "Mom"? Realizing that she was serious I did as she asked, first thing she said was "Nice bra". Then she poked my boob with her finger, and said "wow it feels real". Then she asked me to take my bra off, I did then she stared at my boobs for a few seconds which were an A cup at the time, I had just stopped wearing training bras and started wearing regular bras a two weeks earlier. Anyways then she squeezed one of y boobs, a really weird moment and to begin with I'm her son and she was stareing at my boobs! She couldn't believe they were real.

My sister has also accepted me as a her now younger sister, she joked the only thing is to not let my boobs get bigger then hers. Were pretty much the same size now.

The only person that hasn't accepted me on any level is my Girlfriends Dad. Well for obvious reasons he wants whats best for his daughter and he didn't really like me before anyway.

Right now I'm not planing on getting surgery, because everything still works, although I don't think I'm fertille anymore. The only thing that might make me get surgery is that my girlfriend is an avid swimmer and although I fill out my top the bikini bottom doesn't fit too well . I think I'll have to find a bottom that has like a mini skirt with it.

And as for natureday, I've heard those types of products rely on body chemistry to work, so results will very from person to person. And I'm not sure what it could do with saggy breasts, I'm not looking forward to that,,,

When I was out shopping at my local mall today, I had to use the restroom. And as I have for the last year I used the woman's bathroom. I just go in do what I need to do, quickly check my hair and make-up and get out. Today, after I used the facilites I was at the sink digging through my purse looking for a gift card. When I went to set a hand full of cards down on the counter, I dropped them on the floor just as a woman walked in, she politely picked a couple of them up. But the one she did was my drivers licence, she looked at my licence and me a few times and said "You.. Your a.. a. Guy!"

Then she went on a big rant on how it is everything but legal for me to be in there. I argued with her saying that I had to go to the washroom and I can't exacty walk in to the mens room in a tank top, skirt, and heels can I?

Eventually she calmed down, and told me to leave and to never use a woman's washroom again.