How I started

[Alexander Wolfe]

Well, I'm one of the youngest members on this site at 14 but heres how i began( or am beginning, not too sure). A while back, when my parents were away along with my siblings. I tried on my sister's skirt(She's 9) and it was very amazing the feeling of it. The next couple times my parents left, I tried them on again until I took it one step up and starting wearing panties as well as her dresses.
This went on, and my parents never found out. Eventually I quit wearing my sister's panties for sanitation reasons and her own privacy.
Recently, I asked my english teacher as a joke if i could come to school without wearing pants. She responded that by school policy, one had t wear shorts or a skirt minumum. So I responded Fine I'll wear a skirt which made her laugh in disbelief. Afterwards, i told one of my friends(shes a girl but she already has a boyfriend) and she agreed to lend me hers. During the last period of the day, i got a pass to the restroom, changed in there, and walked out feeling slightly embarrassed but still laughing about the whole thing.
The next couple times i've been to this girl's house I tried on more clothes. Then I went to this other girl's house and tried one of her dresses on as a joke/for fun/ because i wanted to.
So the original girl ive been talking about is actually a minor crossdresser herself with a pair of shorts with a zipper in front. One day she went to the store with her mom and bought another pair of guy shorts and later told me that she was thisclose to buying man boxers. I told her that if she does to invite me and ill buy panties and she agreed. The unofficial date is sometime this summer. I think that is my story and sorry for rambling if i did. Tell me any suggestions you might have. Oh and By the Way my parents don't know about this whole thing.

[DonnaT]

Just don't get caught up in the euphoria of it all and get careless to where you get outed to your parents.

And continue to have fun.

[PhylissH]

Sounds a little familliar. Was spending the night with a friend in JR High. His parents left us home one evening and I am not sure exactly what i said but his sister, about three years older, left some things hanging in the bathroom. Anyway I comented about it and he dared me to try them on. i loved how the dress and panty hose felt on my skin. after that he always tried to have me over when his folks were going out. It was great fun, his sister would complain and tell his mother to make us stop wearing her things while they were out. Mom never took her serious.

Becarful who knows as most other guys your age will have issues with it as will your parents. and by the way the feeling never really goes away 35 yrs and i still love the way womens clothes feel on me

[Absaroka]

I've often wondered about the boys who issue these dares. I myself used that strategy on my friends and brother. Since most boys learn at an early age that you can manipulate another young boy into a great many things by phrasing it as a challenge to their courage, I suspect that many boys daring someone to try on girls clothes are crossdressing boys themselves.

Absaroka