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I had a ton of time on my hands during the day, especially because my dad and his legal partner were in court all day at least two or three days a week. This was in the pre-Grindr era (I’m dating myself), so one of the only ways to meet guys in a place like that was Craigslist. I had a few friends at college who were into older guys or something else that you couldn’t find on our small liberal arts campus, so I knew the basics but I had never tried it myself. Still, it took me about two days to get curious I wasn’t out in high school and I wondered what kind of guys would be posting craigslist ads in my area. I logged on to kill time one afternoon and found the usual mix of stuff, a lot of older closeted guys who were looking for real love and companionship, and a bunch of pervs who just posted dick pics. There was also one ad for a glory hole that someone posted every single week and I’m still kind of sorry that I never checked it out, but I digress. After about an hour I worked up. The head of his penis slid inside, pushing it's way into my vagina. Mr Ryan kept it there for a few seconds, before pulling back a bit, then sliding in just a bit further. Each time it slid in easily, and him giving me time to adjust to his size also gave to time to think about what an amazing feeling it is to have a man spreading my legs open and spreading the walls of my vagina apart with his penis. The skin on skin feeling of a bare penis is so much nicer I decided. As he finally got the full length into me kissed me again, and asked if I was all right.I replied with a moan, and pushed my hips toward him. He smiled at me again, and began to slowly slide his amazing shaft in and out of me. As he thrust faster and faster, he lifted my ankles up to his shoulders, letting me feel even more of him inside me.As he thrust into me he took my right hand and moved it down to the top of my vagina. I could feel his wet shaft sliding into me, but I wasn't sure what he was trying to get me to.
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