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As the months passed by I would wear my sister's clothes as much as Icould. I loved how I looked and felt in them. I wasn't very masculine andhad a so...t, small body for a boy so the clothes looked great on me. I sowanted to show people how good I looked but knew that it would beimpossible to do so. One night, my best friend was sleeping over my house. We were justbeginning our first year in high school. We were up late talking aboutsex and girls like most horny high school kids did. I commented. I jumped out and told her that it was too much for me, and I didn't want to go through with it. She told me "ok, let me try one more thing, it will help you, you'll enjoy it, trust me", I agreed. She told me to turn around and lay on my back, raise and spread my legs, she placed a pillow on my lower back to raise my asshole a little and the went to look for something on her night stand, she grabbed a normal size bottle of lube and said "I'm going to lube you also from the inside, I'll put in. More

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