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When I started to slowly push my finger in my little pucker it was too much for me and I started orgasming all over my stomach and hand. I lay there for a few minutes recovering from what had to be the greatest experience to date. It became a daily routine for me to come home and put on the clothes that I had and masturbate myself to orgasm. As years went on I actually started buying women's clothing. I would go into stores and pass it off as if I was purchasing something for a girlfriend then I'd go home and play dress up for the evening. I even picked up a new name for myself in costume, Tiffany. I felt it was a sexy name yet very playful, like me.It was my senior year right after my 18th birthday when I had my first experience with another person. I had met Jeff online. He was a few years older than me, 28, not married and a fun guy. I don't remember how it was brought up one night online, but somehow I said I had worn panties before to high school one day. He told me he thought. Diane nodded and grunted something about cramp to him again.I heard her husband carry on a conversation with the neighbor. Diane turned back to me and whispered “My God, how does Amy get this thing to fit? I've never had a cock this big - the head is as big as a fist.” Diane started pushing herself back against me as I rammed my cock deep into her. My hands reached around her, and I started to play with her tits which hung down invitingly. Her age meant they sagged slightly which in my mind just made them an even sexier sight. I pulled them hard and kneaded them roughly as I rammed my cock in-and-out of Diane. She clearly liked it as every time I pushed my cock into her she thrust back against me to maximize my penetration. I wasn't yet fully inside her, but my hand reached around to grab her stomach so that I could pull her back properly and fully enter her. I could feel the slight sag and overhang of her stomach which again was a sign of aging. It felt great and I grabbed her.
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