I Am a Teenage Crossdresser Stories of Experiences (Page 3)

Hey, just uploaded a couple of pictures of me crossdressed, this is the first time I've ever taken pictures while dressed, go check them out :) x

I have decided to come out soon, but I don't know how? Any tips?

Ever since I was a small child I've always felt different about who I am. I always wondered what it would be like to be girl for a day. I never acted on this then. I continued to be a regular boy all through primary school. It wasn't...

I am a teenage crossdresser I wish there were more of my friends that were crossdressers also

Okay guys I'm back again with another help thingy. So my family is going through really bad money issues. And I want to tell my mom that I am transgender but she will want to do all of this stuff for me but we can afford a single dress...

I told my best friend about my crossdressing, after weeks of thinking about telling someone. I never thought that he would've been the one I told, but I'm glad I did. This had been weighing on me heavily for months and I didn't know...

My name is Garrett, I am 16 y/o and I am a crossdresser. Today I finally decided to tell someone, and that someone is my best friend Cameron. Cameron, I like wearing women's clothes. It was extremely hard for me to admit but you deserve...

I'm a cross dressing teen who has since I was 13. I was wondering if anyone out there would wanna chat and talk with me about all this stuff

I haven't crossdressed in a while now and I hate it. I hate not being able to do it when I want too. Especially when I went girl shopping with my gf yest and we looked at lots of pretty clothes. I just wanted to go try it all on! I can...

 I first got in touch with crossdressing , when I was about 5. I got in contact with the daughter of a good friend of my mom. She was a big Sailormoon fan and had got some cosplay costumes looking like their uniforms and also a blonde...

Can someone tell me how I can get some more clothes to dress in? I'm currently making do with the one dress I have, but I want to get some more that fit without raising suspicion. If you have some ways I can try please comment below.

im a full time cross dresser i take hormone pills and grew my hair out everyone know i wear girls clothes because i dont own any guys clothes. Im 16 years old and go dressed to school im not gay or straight im a sexual. I would love to...

Recently I've had alot of thoughts about telling someone about my crossdressing, and every time I get this swelling pain inside and I just want to let it out, but I can't. I know i'm not the only one that has this problem, and that's...

I am 16 y/o and I have been a crossdresser for about 6 years. I carry alot of stress from school, trying to hide it, trying to get new clothes discreetly, ect. and I want to tell someone, but it's so hard to believe that anyone it today...

Crossdressing is a way that makes me feel like nothing else does. It's really exciting when you know you are alone and you have the chance to slip on some sexy panties or a cute dress or even paint your nails a pretty colour. Even if it...

Today I showed my closest friend this site because i've been on it alot and I wanted to share its capabilities. So I made a new account and showed him the site(I did not use my own because it would reveal more than I care to explain to...

Hey everybody!!! So i think i'm finally ready to face the fact that i'm Bi. Just every-time i get dressed up i get so horny that i would do anybody. I know that sounds really bad on my end but its true. Like if i guy asked me to give...

I like feeling pretty and crossdressing is just great. I love nail polish so much! My favourite colours to try on are bright red and bright pink because they are I think the prettiest colours to wear. Make-up is another that I can't get...

Being a closet CD is so hard...The amount of times you just want to tell people. I keep it a secret because I'm scared and I think people wont accept me. I can't help that I like women's clothing and feeling pretty. I don't see why...

One of my favorite things to wear are these white and pink knee high socks that have these little multi-colored hearts on them. They're so warm an cozy and they make me feel pretty. ; )