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When I Was 11

I remmber this so well i wa one of the few boys in school who had long hair teased a lot buy other boys and some girls,until one day i was at a friends house he had a sister who was 3 years old and some time dressed him up for fun,she said she would dress us both and soon i was in my frist school girl out fit panties and bra i just loved it.After that i was at his house when ever i could Tim grew out of dressing up but i did and lucky for me Ann loved t odress and see me dressed
bobbyboy652 bobbyboy652 13-15 5 Responses Oct 26, 2011

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like wearing dresses because they are comfortable! I also like the looks of them! I feel less bored when in a dress! I feel more comfortable and confident in a dress! I dislike mens clothes as they are drab and seldom fit right therefore extremely uncomfortable! I wish I could get away with wearing womans clothes 24/7! I know when crossdressed I look like a beautiful girl.....

You need to tell her how much you luv being dressed up and also ask her to paint your nails and toes and help you with makeup. Tell her you want to look like and act like a girl all the time. She may give you some of her hand me downs to get tarted with.

I know that wonderful feeling too sweetie<br />
Hugs<br />

hi sammi thanks maybe we could chat some time

Very Nice Bobby, You are lucky to have a friend with a sister like that. Are you still having her dress you or dressing on your own? I would love to see some pictures. Message me and I will give you my email address.

hello no now i dress my self she when away :)
my email is

yes i did thank you :)

thank you i just tell her

Melodie your like a guys best friend. ok so one time when i was sleeping my mom snuck in when i was grounded and was sneaking me into girls clothing a blue flower gown white tights and some black sandals

Did you talk to your mom? What did she say? I would love to hear more.