"The Unplugged Challenge" - Sex Stories

"The Unplugged Challenge"

... make sure that there was no other possible reason she’d be asking my friends questions about me before I had the courage to approach her. The couple other girls I’d kissed had all made the first move. Objectively speaking, that even one had done so suggested that I was good looking, but somehow when I looked in the mirror I never saw what they did, so the anxieties continued. For a while as I pumped up and down on my dick, I wondered which of her friends might like me, but that thought fled as I noticed her dipping her fingers into her hole, sliding them inside and withdrawing them slick. It wasn’t a one-time motion, she repeated it over and over again. Her thumb would, every so often, make a circular motion, pressing in, not on the clit itself, but on the flesh immediately above it. She was starting to breath differently too, like she was holding her breath for short bursts and then releasing it all at once. Seeing my s****r masturbate so openly made me pick up my pace as well. “So, do you think I’m hot?” she asked suddenly. “I mean, forgetting that you’re my b*****r. Just pretend you’re some guy and we don’t know each other.” “Yeah,” I said. It was getting hard to speak and maintain focus. I was no longer urging an orgasm on; I was trying to hold it back. “You’re gorgeous. I mean, I always knew you were pretty, but with that body, wow.” I smiled weakly. “If you weren’t my s****r I’d…” I’d trailed off, so she prompted. “What?” “Anything you’d let me,” I said. Unfortunately ...

... that was the way it always was with girls. Sexually speaking, a guy would be willing to do anything a girl would let him. Didn’t my s****r know that? “Fuck, I’d eat you out for an hour, even if all I got out of it was a close up look.” Her legs moved closer together, squeezing slightly. “Ha,” she said. “As if.” Her fingers quickened. I guess she was starting to get into it. Maybe I’d even see her cum. That thought pushed me over the edge. My dick felt like it suddenly stiffened one last bit, even thickened, and no longer did it depend on my motion to give it pleasure, it felt incredible with no motion at all. Pressure rose up from the bottom of my shaft. My s****r said something, just the word, “So…”, but I couldn’t pay her any attention. Before my mind blacked out entirely for its moment of bliss, I reached over to hurriedly grab some tissues, put them in position. I didn’t moan or grunt, just shook a little as the first jet burst up and out of me, landing in the Kleenex while I was overcome with a more intense orgasm than I’d ever felt before. A second and third jet followed, not quite as pleasurable, but still better than the average first cum. After that, there would be a few more waves as the rest of my cum made its way out over the next thirty seconds or so. There seemed to be a lot of it this time, but then I’d been saving up. “I guess you’re done,” Krista said. It was funny, she sounded almost disappointed. “Yeah,” I said. Once again uncertain and awkward, I began said ...