He could tell that it would be a difficult fit, despite the fact that she was sopping wet from him eating her.He applied a slow, consistent pressure as he began penetrating her. He was not even glans-deep when he ran into the resistance of her hymen. She was trembling, her eyes screwed tightly shut. “Tell me if it hurts, okay?” She nodded. He continued on, gently piercing her maidenhead. He saw a tear trickle down her cheek. “Do you want me to stop?” She quickly and decisively shook her head no. He continued pushing, an inch at a time, feeling the hot, velvety pressure of her unused sheath give up its resistance and allow the intrusion of his shaft.It took a while, but he was finally fully inside her; his scrotum firmly against her rectum. He paused. He could feel her tightness squeezing him in time to her breathing, which was ragged at first but which calmed a bit as she became more accustomed to the fullness. He then began to slowly withdraw. Half-way out, he reversed, slowly. "Don't you dare! Damm, you know how I like you to fuck me!"John smiled. He knew I knew he had planned this all out ahead of time. And been patient enough to pull it off. Now I was his weekly fuck-toy and I was enjoying it.FWB: Friends With Benefits. I didn't expect these kind of benefits but I'm sure glad John knew about them.It started about six months earlier. I had chatted with him on adultfriendfinder and we agreed to meet and chat. He told me he enjoyed giving blowjobs and thought he was pretty good at it. Sounded interesting. Since I didn't have a steady girlfriend, I invited him over to see how good he was.Yes, he was pretty good. Better than most girls. And he brought some weed. Getting blown while high has always been better for me and he was pretty good. Damm good! The first time we chatted for a while after my first blowjob. He worked Sunday through Thursday and always had Fridays off. I worked ten-hour shifts taking care of the computer systems at a chain of assisted.
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