When I was a kid I used to cat-sit for one of my neighbors when they went out of town. I got a decent pay and I would do it every couple months. When I hit puberty and discovered masturbation, I took up the habit to jacking off to the neighbors' daughter, who was a couple years older than me. I at one point started pulling out her clothes and cumming on them, imagining that she was in them.

The summer I turned 16, I was asked to watch the neighbors' cats for a week. I was offered the usual pay, but the mother said that she would "pay me extra" if I did my job did. Of course my teenage mind knew what she meant, so I made sure to do extra good in feeding their cats. I didn't even jack off to her daughter to prepare for what I knew was coming.

At the end of the week, the mom credited me for my good work. She paid me my $75, but she also invited me upstairs to see her bedroom. She was in her late 40s and looked good for her age. When I went in there, she was already taking her clothes off. She helped me take my clothes off as well, until we were both standing there completely exposed.

She walked over to me and threw me onto her bed. My heart was pounding right out of my chest as she slid on top of me and began to fuck me. I think she could tell I was a virgin, because she took it pretty slow to start. After a while, we picked up the pace and I could feel that I was getting close. She said I could cum inside of her, and that's exactly what I did. The biggest load of my young life went deep inside of her. It was the best thing I had ever felt at the time. We laid there for a while and fell asleep with my cock still inside of her. When I woke up from that nap, I cleaned up and went home.

We fucked once more after that, with that session being much more intense than the first one. I also fucked her daughter that same year when she came home from college for winter break.

I've had some good sex in my life before, but nothing beats that very first time when I lost my virginity to the one person I did not expect to lose it to.

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