“That will help some; try and relax. I expect to get to use that hole someday too”, leered Frank. “Holy fucking shit”, I shuddered at the thought. Bill positioned his cock at my virgin (almost) hole and pressed while he told me to relax and enjoy. Even though he had prepped me for a while, it still felt like this was not going to work. All of sudden the head popped past my ring and motherfucker it hurt! I started to slide back up the couch trying to get away from him and he grabbed my nipples and pinched. “Relax and lay still; you’ll get used to it. Calm down!” I tried to relax but the pain was sharp; I thought someone had shoved a hot poker up my ass! I felt a tear run down my cheek and my cock went totally soft. Bill kept stroking my nipples while he held himself in me. I took a very deep breath and let it out trying to relax. Some of the pain went away and I felt like I would live again. “That’s it, just relax and let me in”, Bill cooed. I finally eased up and Bill. Where her eyes had conveyed initiative and infatuation a few minutes earlier, they now looked tired and worn.“What time do you get off work?” I asked.It would have been my next move anyway before her brother spoiled the mood. “I’m a good listener, especially when someone buys me coffee.”It was an honest friendship offer. She hesitated a few seconds, but my smile encouraged her. She grabbed a pen from her pants pocket, took my hand and started writing something on it. The pen hesitated a bit, too, so she brought it to her mouth and breathed on the tip. When the ink finally flowed, it arranged itself in the outlines of a phone number.“Give me a call at around five, okay?” She raised her eyes at me and smiled timidly, finishing the doodle with a little heart.“Can’t believe I’m doing this,” she added with a nervous giggle, “but I’d love to buy you that coffee.”“Okay, then,” I said, barely able to contain a giggle myself. I checked my hair one last time in the mirror and grabbed my.
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