This was the biggest I have ever been and all I could do was fall asleep with a smile on my face. As time went on I found myself lonely. Riding my post every night was fun, but I wanted to be touched and caressed, I wanted the touch of a man. There was this guy in one of my college classes that has been asking me out for some time now and I think it was time to take him up on his offer. Bill was a class act and knew how to treat a woman. I didn’t tell him this was going to be my first date, after all I was almost twenty years old now, still living at home and never been kissed. All I had to compare with was erotic stories I have read and porn videos, but nothing real. In the back of my mind I had the fear of what he was going to say if and when I let him in my pants.Bill and I dated for almost a month before he started asking for sex. He was a gentleman about it and I knew this moment was going to happen, but I didn’t want him to be scared off so fast. My mother’s words kept. I informed him that I would go slow and that I knew his body well enough to know if the pain was too much and that he was too trust me. He murmured o.k., closed his eyes, and slumped against the table. After generously applying more lube, I moved in behind him to get ready. It was at that moment that I thought he might be right, that thing was huge. I gently squeezed and massaged his cheeks around the head of the dildo and slowly began pushing it into him. He was loosened enough from the previous dildo so that his ass accepted the new one, but I could see how much more it had to stretch and I could feel his apprehension under me. I went very slowly and it actually took several minutes for the head to pass his sphincter. He moaned loudly as it slowly began to enter him. I could tell he wasn't relaxing like he normally does but boy was this starting to look good. The site of that huge dildo slowly sliding into his ass got me going again. I held back though so as not to be to rough too.
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