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I don't remember anything else until I woke up holding her in the back of her Suburban. I was shocked and painfully hung over. She dropped me off at my house after a painfully silent ride, but kissed me on my way out of the car. The next few days she texted and called me nonstop. When I finally responded a week later she asked me out... I am an average to below average looking guy. This simply does not happen in my world, so I was skeptical and unenthusiastic. After dinner she asked me to come back to her place. I didn't know how to react to this so, jokingly I told her if we were going to have sex she'd have to be tied up. Her eyes got real big and asked if I was into that, not picking up on my sarcasm. "Yeah... is that a problem?" "Not at all."I was 19. I had never tied a woman up before. All my experience in bondage had come from kink.com or other BDSM sites I stumbled upon in my internet misadventures and my lack of knowledge showed. I had her hands tied behind her back in a. .He looked at the original dildo that we used to get the girls excited. Made some comment like "its not that big" I told him if he could take that in his ass I would let him have mine.WTF was I thinking? Anyway that toy disappeared right before my eyes.I'm not sure if I was more shocked at the fact that he just popped it in like nothing, or that he was all over that deal, or maybe it was the fact that I was about to let a friend of many years take my virgin asshole.All I know is, I found myself bending over in fromt of him, kneeling on the couch. as he told me a deal is a deal. So I slowly rolled my boxers over my ass and offered my tight hole for him. I kinda felt dirty waiting for a cock with my clothes half off.He said ready? Started to aproach me from behind.When his cock hit my hole, he pushed afew inches, I relized how big that cockhead really was.... It hurt like hell and I jumped forward saying "Hell no, Sorry to big"He must really wanted it cause he just looked at me.
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