I Am a Teenage Crossdresser Stories of Experiences (Page 35)

I'm 19 and have crossdressed since I was 13. In high school my biggest wish was to wear the cheerleader uniform. I knew that I would never ask any of the girls if I could where there uniform so I figured that it would just be one of...

It has been quite the long time since I have written a story on here. Partly because of the huge amounts of school work that have been taking up all my free time, but also because I was thinking. I really stepped back and took at look...

I'm ugly. Mother fucking ugly.
I'm a sophomore in high school, and ever since the summer between fourth and fifth grade, I've been letting my hair grow. It is now down to my middle back, and except for the occasional trim for split and...

So yesterday I said I was going to a wedding for my cousin and his fiance. It was a beautiful wedding but it was a short wedding. It lasted a grand total of 20 minutes. The reception didn't take much time either. So Kim's grandmother...

Okay, so, today I have a wedding to go to. After that I have a dance my friends want me to go to. I'm going to go to both surely. So I'm wearing a normal dress shirt and pants for the wedding because I believe unless you dress daily in...

Okay to start off how fuckin cool is lucid dreaming like seriously I have been wishing for this to happen for years and guess what.It does but I only get half control it is sort of like that fem dominiation sub sort of deal, my mind is...

Forgive me for bad mistakes.
My Femele name is ashley. and i started crossdressing since I was 14 years. First i dress my mother clothes, and do it for 3 years. Acctualy i haven't buy ant clothes for my self. ;) nobody supports me, i do...

I started liking crossdressing when I was 5 or 6 years old, cus my older sister and her friends used to dress me up in my sisters older stuff (she is 3 years older). It even got to the point that my mom asked me if I wanted the clothes...

Hi this is my first story. I LOVE crosssdressing even though I only started 6 months ago and only got to actually do it on a handful of occasions. I love all girls clothes but especially stuff like lingerie,  pantyhose, swimsuits...

Okay so i heard that you absolutely have to be skinny to crossdress. Im thick. But you cant even tell...

Last year sucked; I came to the realization that I was bisexual and that made me so anxious and stressed.I finally got over it, though, earlier this year. Of course, a new revelation took its place, and that was how much I loved to...

Things are better..... I have a transgender boyfriend. (: Well he is my first boyfriend. Ive only been with girls before so who knows what might happen...

So I just wanted to know how many of us have had close calls of getting caught crossdressing for all of us that first time is accelerating with the thrills that u could get caught but for me that has happened many times and here are...

When I was 8 years old I had to spend several weeks with an aunt, soon struck me wearingunderwear, and also that of my cousins ... secretly took them to use them, it continued to do so when visiting, even after returning to my home...

I changed the names of my cousins just for privacy reasons anyway here is my story.

A couple of years ago we visited Queensland where my cousins lived for the weekend. There was Glen the 16 year old in charge of the younger kids. Riley...

You know its amazing how when you crossdress or think about it you sort of act like a girl over a period of time such as; I adjusted to going to the toilet sitting down now I can't go sitting up. I have started to think like a women...

ok so Im a straight 16 year old boy and I usually don't write about my crossdressing but I'm like really confused. I started when I was like 7-8 when I joined swim team and I had to wear a green speedo. At first i didn't like but for...

I was totally a teenage CD back in the day. I don't know when it started exactly but it was really before I was a teenager. It's just that it got interesting as a teen...hormones and all. :)

Teen CDs out there...just know that there...

When I was little, I would've given anything to be a boy. I played with the boys, I wanted to dress like a boy, think like a boy, BE a boy. Now, I indulge myself sometimes and wear men's clothing. I shop in the men's section sometimes...

I discovered that I'm fascinated by girls' clothes a year or two ago (I'm 15 now), so I want to try crossdressing, only in private. I've tried my mom's clothes, but they aren't the kind of clothes I wanna wear (I want sexy, teenage...