Crossdressing Stories


A NEW BEGINNING – Crossdressing Story

My name is David and I am 20 years old and live in Las Vegas. I have always been small for a man 5’4″ tall and weigh about 50 Kg, so growing up I was always teased as I look like a little kid. I hated it and always wanted to grow bigger that is till I was 17 and discovered girls clothes. Yes it turns out I am a crossdresser.

I just love dressing up with the makeup, hair, dresses and heels and I actually grew my light brown hair out past my shoulder and wear it in a pony tail so when I dress I can use my own hair. I actually make a fairly passable girl although my makeup skills suck and my collection of makeup and clothing is small.

My parents were killed in a car wreck when I was 18. I have been living off of the insurance money, I have a small apartment and dress at home and have never gone out as my clothing are all second hand stuff and really don’t look that great.

I had only been in the apartment about 2 weeks when I met Natasha she lived right across the hall from me. She is gorgeous, 22 years old 5’5″ and long blonde hair. Just the kind of girl I would love to date and if I thought she would go out with me I would try to stop dressing but she could have any guy she wanted.

She works at the Paris hotel casino as a cocktail waitress. We would talk and built up a friendship. About a year ago she was going on vacation and asked me to water her plants and look after her apartment and gave me a key.

So while she was gone I went over and watered her plants and I don’t know why but the second time I went over I just had to look in her closet and she had so many beautiful things and as we are about the same size I tried on one of her dresses.

Now I know this was wrong but I couldn’t help myself. The whole week she was gone I spent most of my time over there and tried on a lot of her stuff and wished I could have such beautiful clothing.

I couldn’t stop thinking of her clothes and wondered when she was going on vacation again. It was about 2 months later when I couldn’t control myself and as she worked the late shift at the casino I went over to her apartment when she went to work and tried on a couple of her dresses and I was in heaven.

I started doing this more and more to the point I was going over there almost every night when she went to work. I saw no harm in it even though I knew she would be mad if she found out but her stuff was so much more beautiful than the things I had bought at goodwill.

Well everything was going great till about a month ago, Natasha invited me over to her apartment for dinner and to ask me a favor. I was hoping she was going on vacation again as I would have way more time and not have to worry she would come home early.

Well I got to her place and she invited me in, the food she was preparing smelt so wonderful and we sat down at the table to talk. Natasha smiled at me in a way I have never seen before and said “I want to show you something David” and she turned her computer towards me.

She looked me in the eyes, “I forgot to turn my computer off a few weeks back and my web cam caught something I can’t explain.” I looked in terror as I saw myself in her bedroom trying on her red dress. She smiled again, “I started leaving my computer on and have many videos of you trying on my clothes.”.

I was really scared and just started to apologize knowing we were done as friends. She looked at me again, “I am mad at you but not because you were trying on my clothes but because you did it without asking.” I looked up as she smiled, “Please tell me why you did this?” I told her about my cross-dressing and how the clothes I have are all second had and don’t look good and I just couldn’t control myself when I saw all her beautiful clothes.

She smiled at me and gave me a hug, “I guess if you like to wear pretty clothes that is okay and I don’t mind you borrowing some of my stuff but you must ask first okay?” I shook my head yes and thanked her. Now was the biggest shock as she smiled at me, “we have about an hour till dinner is ready so why don’t we go pick out some nice dresses to wear.”

Now I was so excited and scared at the same time, I really wanted to but I have never let anyone see me dressed but then again she had several videos on her computer so I said yes. This time though instead of just the dress Natasha gave me a bra, panties nylons and heels to go with it.

In about 15 minutes I was standing there in a beautiful red dress and heels and Natasha had on this really cute black dress and yes she even had breast forms for me. We still had time so she had me sit down and she quickly combed out my hair and put some rollers in it, “if we are going to do this David we might as well do it right.”

Once my hair was up she started on my face with makeup and she was way better at doing makeup than me. My eyes looked perfect and she finished it off with a red lipstick. I looked in the mirror and could not believe it. I looked totally like a girl, even Natasha commented on it, “wow David no one would ever know you were a guy.”

We had a wonderful dinner and then sat around and talked. We became really close that night, not just best friends but there was a bond between us as she knew my deepest darkest secret and was okay with it.

We did this a couple more times on her nights off and had a blast. It was about a month later when I was over to her apartment and we were all dressed up, we both had on these really cute black cocktail dresses and 4″ heels and makeup done perfectly when she smiled at me, “you look so awesome tonight it is a shame to stay home.”

Now, I have never gone out dressed even though I often thought about it but with Natasha’s support we left and went down to her car and off to dinner at the Paris Hotel casino where she works. We had a wonderful dinner and then went to the casino. Now as I said I am not 21 yet so I was scared but no one questioned me.

It wasn’t till Natasha ran into a couple of her co-workers that I got really scared. She just smiled and introduced me as Julie her friend from High school. With that I was accepted as just another pretty girl. The 4 of us hung out together the rest of the night and no one had the slightest clue I wasn’t a girl. We stayed out till the wee hours of the morning before heading home.

I asked Natasha who Julie was and all she said was a friend from High school that she had lost touch with. We got in the habit of going out on a regular basis and I met some more of her friends and in every case I was accepted, my small size was really a blessing now plus Natasha and I grew closer more like sisters.

One night when we were out with her friends they told me I should apply for a job at the Paris Hotel Casino as they are always looking for people. I just smiled and said I would think about it as I knew there was no way I could.

Now I was spending two nights a week as Julie as I always went out with Natasha on her nights off and Natasha had taught me how to do my makeup so if I wanted I could dress on my own which I did on some occasion. It was Saturday morning and Natasha wanted me to get dressed up to go out which was new as we always went out in the evening but I was willing as I had become so comfortable as I passed so well. We left and went to a local shopping center and there was a beauty salon there that Natasha went to.

Now I was a little nervous about this as I am still a guy in a dress but she told me it would be fine. She just wanted them to fix my hair up in a little more feminine style. Natasha told the lady what she wanted and I just sat there. It was a wonderful experience as they shampoo your hair and massage your scalp. It was very relaxing.

She trimmed the back and cut my bangs and then put a cream in my hair. After a few minutes she rinsed the cream out and more conditioner and rinse and then she started with curlers and wrapped my hair up.

While my hair was drying we both went to the manicure tables and Natasha talked me into getting acrylic, “you can always take them off in a day or two if you don’t like them” she said. It really was a fun experience and after about an hour I had long beautiful red nails, they were about a ½ inch long just like Natasha’s.

I was back to have the rollers removed from my hair and a mass of curls fell down but something was different. My hair was now blonde. I wanted to scream but didn’t, as I didn’t want to cause a scene. We left the salon and when we got into the car I was ready to yell at Natasha and she knew it so before I could speak she spoke up “Don’t be mad David but the other night I got thinking about you needing a job and I figured why couldn’t you work where I do, I could give you a good reference.”

I just looked at her, “Natasha I am a guy, to get a job I will have to give them my real name, they are not going to hire a man who dresses as a girl.” Natasha got quiet and then started telling me about Julie her best friend from high school.

It turns out after high school she got mixed up with some guy and ended up on the street.. Any way it got so bad she had joined a cult and in doing so had moved away and was going by a different name as the cult likes them to forget everything from their past life. It was a really sad story. That’s when Natasha told me I could just use her name to get the job and work as her since all her friends already knew me that way.

Now I was about to say no but this idea did sound a little exciting, I could live as someone else for a while. I told her I would think about it so we went out shopping for the day and out with her friends for the evening.

Now the next day I got up and looked at myself in the mirror. With my new blonde curly hair and nails there was no way I could go around as a guy so I put on a nice skirt and did my makeup and went over to see what Natasha was up to. She was so happy to see me all dressed up.

We went out and had a nice lunch and did some shopping before she went to work. Now I have gone with her before when she had to go to work and came home by myself but this was the first time I was doing it as Julie, I had never been out as Julie on my own so I was a little scared. But I really did look feminine and the worst thing was some whistles from men I passed which on your own is a little intimidating.

Over the next few days I went out more and more on my own and was getting pretty use to it. It was Sunday night when Natasha and I went to meet her friends; well I guess they are mine too now. We went out to have a nice dinner and while we were talking I asked if they thought they had any job openings that I could do.

Natasha looked at me and got such a big smile on her face and gave me a hug. She told me we would go down to the employment office first thing tomorrow morning and she would help me put in an application. It was a fun night and we all had a blast but Natasha said we should not stay out as late so we could be there first thing in the morning. The next day I got up and got all dressed and went over to Natasha’s. She had me take my top off including my bra.

She had what she called a nude bra. What it really is are two silicon breast shapes and what woman do is attach them to the outside of their breast and then pull them together to increase their cup size. I really wasn’t sure what this would do for me. She attached it to the outside of my chest where I had a little bit of flab.

Once it was attached and had set for a bit she pulled it together in the middle and put on a tight bra. I was amazed, I had breast and cleavage. They were not huge but a nice C cup size. Natasha gave me a new top that really showed my new breast off and off we went. Now I was a little self conscious as I felt a little different.

We got to the Casino’s employment office and it turns out if you come in with a current employee you go to a different office, seems they give preference to friends of employees. Now I was introduced to a lady named Sara, she was in charge of all hiring. She asked me some questions and had me fill out an application which Natasha helped me with as I really didn’t know all the answers to Julie’s life such as birthday and such.

Turns out I was now 22 just like Natasha. Sara came back and asked me some more questions and had me stand up and turn around. She was really looking at me and I just knew she had figured out I was a man. She left again and Natasha smiled, “She likes what she see I think you may get a cocktail waitress job like me.

They only hire really cute girls for that. The money is okay but the tips are great.” Now I was still having a hard time thinking of me working as a girl but now I was picturing myself as a cocktail waitress in one of those tight skimpy outfits. Could I really pull it off? Sara came back and smiled.

“I think we have an open cocktail position that would be perfect for you if you are interested. It is the same shift as Natasha’s so she would be training you.” Wow I was offered a job. Should I take it? Could I pull it off? Natasha nudged me and I said “Yes I would love that, thank you.” Sara handed me some paper work to sign, I read it and it was authorizing them to do a background check on me or rather Julie.

I signed the paper work and the 3 of us walked from her office to the front desk, Sara handed the paper work to the receptionist and then looked at the Security guard, “This is Julie, a new hire, here is her authorization for a background check.” He looked at me, “everything looks good step up to the line.”

I did as he asked and he took a couple pictures and showed them to me. I got to pick out the one for my employee ID badge. Then he had me stand at the counter and he took my figure prints which caught me off guard. Now I have no criminal record and have never had any contact with the police so I knew my figure prints weren’t on record any place so I was okay there.

He looked at me, “Here is your temporary ID. You will get your regular one when you pass your background check and the Gaming commission files your paper work and gives you clearance to work in a casino.”

That’s when it hit me. It was not the problem of my figure prints being on file before it was the fact they were now going to be on file and for a woman named Julie. Officially in the eyes of the State of Nevada, and the gaming commission I was a woman and it was now in their computers that way.

I may be stuck now living as a girl. Natasha and I left and she was so happy that in the car she gave me a big kiss which, was the first time we had kissed and it caught me off guard. My first night was tonight to start my training and apparently my new life.

What will happen next, will I be found out, will it all work out okay, can I ever go back or am I now stuck as a girl full time, have I gone too far? Only time will tell.

The End

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  1. I loved this story!!!!!! As a girl “wanna be” I can so identify with wanting to be a girl full time. I dress almost everyday and it just seems so natural for me to be dressed as a girl. I imagined myself as “Julie” and wished that this would happen to me, and if it did I would NEVER think of going back to being male.

    1. Somehow it’s nice to hear that you’d like to be a girl all the time. I’ve always dreamed that one day I could meet a girl like you. I would like to be supported and safe and maybe we could even get married if everything went well. But let the future show.

  2. I wish this could happen to me cuz I love dressing as a woman being a woman I hate being a man wish I had a girlfriend like the one he’s got now

  3. I love the fact that it was just a little bit out of control! I could just imagine Julie realizing that wearing the clothes, the makeup and the shoes, plus the added work of tucking, creating cleavage, and doing hair was not optional. At what point does Julie ask her trainer whether the benefits include gender related or cosmetic procedures and medications?
    I had a dream one day that I was busted at work (in a warehouse on a loading dock) wearing sexy boots and a sexy outfit (I thought I was alone and the boss was busy in a different building). When he found me, I guessed that he liked what he saw, but he was so matter of fact in what he said. “I can’t have the guys being confused, so you’ll have to pick one or the other, Jon or Jennifer. And the way I see it, you’ve been doing this for a long time, so I’ll just go with Jennifer and change your badge and the schedule list. I was stunned. I knew the guys had seen me on TV in a documentary about female masking, but I was still surprised that the boss knew my female name. I could only reply with “ok”. He immediately said, “but you still have to wear steel toe boots and jeans. See you tomorrow.” And walked away. I thought, oh boy, will he tell the crew so they expect Jennifer to prevent sexual harassment liability? Or is he just messing with me, and is planning to watch from a distance to see the fireworks and drama unfold? He’s that kind of guy too. But he’s hard to read and always covers his ass when it comes to risk. I didn’t sleep much that night. In the morning I decided to try it, to push my limits and fears. The guys already knew where to see me as a woman, so it should be no surprise there. I’ve told several of them that I don’t bring it to work for their own comfort and consistency. And yet, I always have wondered if any of them were too afraid to say they would like to see it in person, or if they just didn’t want to see me that way. So I decided to find out.
    Positively no surprises. Some guys were teasing and some complimented, and others knew better than to say anything that could get them fired. But as with me hosting Rubberdoll events, even the skeptics came to realize that I am the same person, same humor, same work abilities and same conversation. I guess there was one surprise. One of the guys asked if he could try some stuff on at my place…

  4. Wow that beautiful comment about your life was dressing up as woman and your girlfriend was so amazing to help you out and tell her a truth

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