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I felt a cold liquid spread around my cheeks and up my asshole. He had brought a lube, why should I be surprised? He was here for a reason.I felt pain as something warm entered my asshole. It was pain at first but it started to feel surprisingly good and my cock started to get hard again. He moved faster and faster and my body started to warm but I knew I would win the bet until he pulled out. I figured he had gotten off and I had won but that’s when he let me know that had been only his finger. Still with only minutes left, the eighty bucks was surely mine, or so I thought until he pressed his dick against my ass. Immediately it felt good and as he pushed deep into me it was as if a dam burst. This was obviously not his finger but it slid in me just as easy. I felt heat and a little pain but most importantly my rock hard cock began to leak pre-cum as his cock massaged my prostate. I heard grunting and groaning and figured he was enjoying my virgin ass until I realized it was me. ‘Oh, don’t be. You’ll do fine. Here. Drink.’ Angela handed him the beer. ‘Thanks.’ Jason took a long swig of the beer. The phone rang, and Angela excused herself to go answer it. She came back in a little bit and sat down. Eric and our mystery guest for you will be here shortly,’ Angela said. ‘We have dinner almost ready.’ ‘And it’s smelling great, Angela,’ the brown-haired girl said as she came out of the kitchen. ‘So, are you going to introduce us, or are we going to fuck as strangers?’ Jason’s eyes grew large at her statement, and he started to sweat. Angela looked sharply at the girl, relaxed, then winked. ‘Jason,’ Angela said, ‘this is Sherry, Eric’s assistant at the office. Sherry, this is Jason, a coworker of mine at the spa.’ ‘Nice to meet ya,’ Sherry said, walking to him and extending her hand. Jason shook it. ‘Same here,’ Jason said. ‘Sherry and I have known each other since high school,’ Angela explained, ‘and when I found out she worked at Eric’s office, I simply had to.
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