The guy was laughing hysterically. But he also kept looking at me as if to ask, "Are you serious?"And that's when it dawned on me. I was serious. I was going to do it. At that point it seemed clear to both of us that that night was the night. We excused ourselves and rambled home. Soon I found myself bent over on Mac's bed, my chest pushed up against the mattress, while she strapped the harness around her long legs and smooth hips.When she penetrated me for the first time I tensed up and let out a long succession of soft, high-pitched "ow"s. I was not off to a manly start."Are you ok baby?" she whispered. The strap-on was inside me but she wasn't thrusting. Instead she was leaning over me, her weight on my back as her fingers petted my face."I'm fine," I lied.Mac knew I was bullshitting. Her movements were gentle and deliberate as she started to slowly rock against me. My ows dissolved into whimpering."Shhhh," she hushed, kissing my back, "you're doing such a good job."But I wasn't. After our sessions, I had some of the best orgasms of my life. It wasn’t that I didn’t want to have sex, but deep down, I knew Colt wasn’t who I wanted to lose my virginity to and he respected our relationship enough to never pursue it further and, let's be honest, what guy would ruin their chances of no longer getting a daily blowjob? Now as the year was winding down the realization that Colt was going to go back home for the summer hit me... I needed a new conquest to continue exploring and that person became Jimmy. As I moved back home for the summer, I realized I was desperate for a car. I began waitressing at Denny’s and this is when I met Jimmy. Now for anyone who has ever worked in a restaurant, it is probably one of the most sexually deviant places, full of sexual tension, innuendoes and lots of boredom when the place is slow. My first week working was hard, the waitresses viewed me as annoying because I was young, barely knew the menu and probably was a bit too.
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