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I tidied up the mess and put the underwear back away. Having gotten away with it once, I got more and more adventurous over the next few months. I ended having some amazing orgasms in various states of cross-dress. Over time I tried different lingerie including Basques, baby dolls and my favourite stockings and suspenders. I even refined my plan and when time was tight used a condom to avoid the dash to the bathroom. After a while I decided to go further and fully cross dress. The first time I tried it I got very excited. I picked a partially short skirt, stockings, suspenders, thong, matching bra and tight top. When I was dressed I borrowed some lipstick and finished the image with sexy vibrant red lips. Before long I had the skirt hitched up and was masturbating my erect cock. I was so turned on it didn't take me long to cum. I took the top and skirt off and started to put them away. At that point I heard the front door open and I started to panic. I quickly finished putting. Maybe it will change my mind.” Once again, all I could do was stare at him. “Come on, you’re a beautiful woman. A little chubby, but beautiful. I would hate to just go home thinking that you have this enormous fault, when maybe your tits really do look good, and I will be completely unfairly thinking they look awful.”I just couldn’t believe what this 14 year old boy was saying to me. But he wasn’t done.“If it makes you feel more comfortable, I’ll let you see my cock too.”“Oh yeah, that’s exactly what I want to see, Chuck,” I said. When I said it, I meant to sound sarcastic. But in my head, I knew that the statement held more than a bit of truth.He smiled and said, “Fine, then I guess I’ll just go wait outside if you are gonna be that way.”I stopped him before he left the kitchen. “Wait. If you show me your cock first, I’ll show you my tits.”Without saying another word, Chuck grinned and dropped his shorts. I couldn’t believe what I saw. I could tell he was semi-hard, and it was.
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