1st time EVER - my story & pics

[ilianar17]

Glad to be part of this forum! Hello everyone, I'm Iliana from Greece and I'm 18 years old.

Here's my story:

I was thinking about crossdressing since the age of 14. Two years later, aged 16, I started wearing a few things here and there from my mother's closet when she was away. Another two years later, aged 18, I got to crossdress FULLY (makeup, dress, heels n' all) twice.

The 1st time - Around February there is the corresponding "Halloween" for us Greeks. I got my girlfriend to dress me up entirely and do my makeup (she has a lot of skill), while I was claiming that it's a "fun idea". And it was. I had a full night out dressed as a girl WITH my girlfriend (whom I love like crazy) around a lot of people which I knew. 80% of the people I talked to didn't recognize me at first glance. I was feeling super pretty and like I was walking on a cloud. It felt awesome. [I also finally understood how ladies feel like when it's cold outside .. ]

The 2nd time - I'm quite a normal guy. By my looks you'd never guess I've ever crossdressed. I have a beautiful girlfriend and I visit the gym regularly. Although, one day my mother got out again and she would be away from home for quite a lot of time. A massive and strange urge to crossdress struck me out of nowhere. I thought I was done with it. Lo and behold, here I am again trying out clothes from my mothers closet. But things were different. I had in mind precisely what I wanted to wear and I also for the FIRST time did my own makeup. I remember the exact makeup-stuff my girlfriend used on me so I did around the same (and got it!). So first I shaved my face clean, plucked my eyebrows a bit and started working on the make up. I immediately got the clothes I wanted from my mom's closet. Suddenly there I was, all ready. The heels were a number smaller and my feet were hurting me badly, the wig was all over my face and it was pulling my earring and my stockings were nearly torn (from haste of putting them on .. lol). Male clothes are ofcourse never that difficult, but I felt better dressed like that. I felt VERY beautiful, free. I didn't want to lose that moment so I grabbed my phone and got a few pictures.


I don't know if I'll ever go full time since I still have trouble deciding whether I should keep it as my very own secret.

I'd like to have some feedback on my "other side" looks though, because I'm almost certain this will happen again!

Thanks for reading and sorry for any bad English.

Much love to all of the beautiful members in here!

[Brandy Mathews]

Iliana,
Very nice pictures, and I am glad that you had so much fun. Good luck in the future and I hope that you just have fun in life. I wish that I had a girlfriend in my life like you have there.
Hugs,
Bree

[Lexi_83]

Welcome, glad you are enjoying your new expression.

[Curiosity666]

Welcome to the dark side

A massive and strange urge to crossdress struck me out of nowhere.

It's funny, it was the exact same thing with me. I had dabbled when I was younger, but hadn't even thought about dressing for years. Now that I'm living away from home, bam, I want to be the prettiest girl I can be.

I wish you all be best on what I'm sure is going to be a weird and wonderful journey

[Alice_2014_B]

Looking very nice!

[Bridget Ann Gilbert]

Hi Iliana,

Welcome to the forum. One thing I think everone here will tell you is that now you've had this experience it will stay with you for life. You may find youself in stages of life where dressing may not be possible or open up conflict with other people. How you handle that will be up to you, but your female self will always be a part of you. My other advice is to start buying your own clothing. It is not respectful to wear other people's clothing without their permision. Plus, you will get to establish your own style. Good luck.

Bridget

[ilianar17]

Thanks for the advice. It is extremely hard to find, purchase and even store my own clothing anywhere. I'm working on it though. It is so comforting to know that the "female me" isn't going anywhere!

Thanks everyone for your kind words!

[kimdl93]

Thanks for sharing your story. Please remember that you can decide how big a part this plays in your life. Take your time and enjoy!

[Sissy Jane]

A massive and strange urge to crossdress struck me out of nowhere.

I know that feeling… I have always dabbled with women’s clothing, nothing very substantial – but a couple of months ago I had an overpowering urge to try on lady’s clothing! Overwhelming really. I was immediately addicted and wanted to be as sexy as I could – love taking photos.

I started by sneaking around and borrowing my wife’s items but we have always had an open relationship and couldn’t do that to her. I came out to her recently and we are working on this new part of our relationship. I have bought my own clothes and I am loving putting on MY items now!

You look amazing and I am glad you too found that excitement – enjoy your travels in this exciting world wherever they take you!

- Jane

[Janine cd]

You look great. Keep dreaming of being a female and join us.

[ilianar17]

Thank you! It started as a small sort of kink but I never thought it would be of such magnitude (and I guess this is only the beginning!). I feel complete whenever I do it. It's more than a simple addiction. It's a beautiful expression of self like Lexi_83 has said. I used to feel bad and guilty doing it but your wonderful reactions and my sense of finally belonging in a community has shifted my look on crossdressing for the better.

[Beverley Sims]

I am sure you will do this again, you look quite presentable.

[DaniF]

You look great!

[emma-louise]

You look great x