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What Are Big Brothers For?

I was always fascinated by makeup and girl's clothes when I was young. My mother once caught me putting on makeup in our bathroom when I was around 7 or 8. She blew a gasket and was going to make me wear one of my sister's dresses. I cried like a baby, not even sure if I pleaded my case or not. She backed down. I thought I learned my lesson and didn't "experiment" any further. Then when I was 11, my brother thought it would be fun to try on older sister's bathing suits. She had two piece and a black one piece. We took turns trying them on, and looked at ourselves in the mirror. Only problem was that when I tried on the one piece, I felt a funny sensation. Now I had had erections before, but none like this. That fashion show was soon over, but it made an permanent mark on my pre pubescent mind. I later went on to try on the black one piece again, this time on my own. That is a story in itself, but because of that next time by myself, I started thinking that, wow, this must be how girls feel all the time wearing their clothes. I then went back and forth for years wondering whether I should be a cheerleader or a football player. I chose football player. But I still liked to play dressup now and then.
So, one afternoon while my mom and dad were at work, both older sisters were away at college, and my brother was off listening to music somewhere, I decided to play dressup with one of my sister's dresses (oddly enought it is the same one my mother traumatized me with years earlier). Can't remember clearly, but I believe I also applied a little makeup. As I was checking out myself in the mirror, the phone rang which I ignored. That was a trigger for my brother to come looking for me to see why I didn't answer it. He opened the bathroom door to find me there strutting around in my sister's dress. He didn't laugh. Got more irate than anything. Started addressing me as "****** wears dresses". Not really a good name. I would have been happier with Janine, or Jackie. But he said that in passing for the next two or three years, never in front of any other family or friends, but any chance he got. Needless, it never did stop me from wanting to wear my sister's clothes.
JAGandVSfan JAGandVSfan 46-50, M 3 Responses Apr 3, 2011

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when i was younger i would try on my sisters panties

mom never caught me but my sister did she made fun of me all the time na tease me

when she have her gf over she would leave out panties for me to put on an then make me show them to her gf

Like you, I played football (linebacker), but I really would have rather been a cheerleader. It wouldn't have worked out because we had two male cheerleaders and they wore pants and the cheer sweater, not the nice cheerleader outfit the girls had.I did get to wear a cheer uniform one time though, in my senior year. The cheerleaders and band majorettes had a powder puff football game on senior day, and we senior football players donned cheerleader uniforms and led cheers. I had to wear boy undies under my skirt though because some of the cheers exposed our undies.

me too when i was 10 yrs old i went to my friends house for a chat while my mum was working with my friend mum downstairs selling tupperware my friend made me wear girls clothes and make up then we both play push pram dolls and play barbie dolls my mum walk upstair and scream what the **** you do doing i said to my mum i like it but mum and her friend was laugh i said no laughing i want to be a girl mum faint then few mintues later my mum rang my dad,then my dad pop over ask my mum what happend mum said it your son want to be a girl then dad got MAD mum,dad take me home asking me a question why why you want be a girl then i cried i told mum , dad i was rape at school by older boys.then mum and dad was shocked then both understand then my mum take me out to buy girls clothes.now i been woman for 30 yrs now i am proud of my family support me xxx