"The Unplugged Challenge" - Sex Stories

"The Unplugged Challenge"

... it, but mostly it was just my own anxieties. I’d never shown another girl my erect dick, much less masturbated in front of them. I didn’t even undress in front of other guys if I could avoid it. I slacked off in gym class almost solely so I wouldn’t build up enough sweat to really need a shower afterwards. Like most of my anxieties, there was no particular reason behind it except raw, unfocused fear of what other people might think of me. I didn’t know if my dick was normal, too small, too big, looked funny, maybe even smelled funny, or anything like that. I assumed it was probably too small, but I didn’t want to be told it. Especially not by my s****r. “So, let me see. I’m showing you my tits.” I still didn’t want to show her. So I tried to make excuses. “Yeah, but tits are nothing. You can see tits in PG-13 movies. Masturbation is like a sex act.” At first that’s all it was, an excuse so that I wouldn’t have to show her. Either she’d accept it and stay, or leave and I could fap to the memory. Her response surprised me. “So, what, I have to do it too, to make it even?” It wasn’t what I’d intended, but the thought jerked my dick a little. I was going to have to wash precum stains out of my pillowcase if it kept up like this. “Yeah,” I said. If she refused, I still wouldn’t have to show her. If she didn’t… wow. “I don’t know about that.” Damn. I was more disappointed than I thought I’d be. “Well, or at least get all the way naked,” I suggested. She considered that briefly, ...

... then said, “Okay, but you have to take the pillow away first.” I hesitated one last time. “You’re not going to tell anybody about this?” “Oh, sure. I’m going to run out and tell everybody I watched my b*****r jack off while I stripped for him,” she said with a roll of her eyes. Then she looked at me deadly serious. “You better not tell anyone either.” “I won’t.” I took a deep breath, and then pulled the pillow away. Free from resistance, it sprang forward, flopping down, fully erect. I held myself very still, bracing for possible humiliation. Instead, she just looked at it for a few seconds, tilted her head, and said, “It’s bigger than I thought it would be.” I let out a breath I hadn’t realized I’d been holding. Without waiting any more, she pulled her top completely over her head, and then started to unbutton her jeans. Her ass looked good in a pair of jeans, but even better in just a pair of purple and green panties that clung tightly to her. My eyes fixed on her crotch, waiting to see if they’d drop next, not really believing they would. “So are you going to start doing it, or what?” It was as though I was hypnotized. Still staring at her, my hand slowly moved towards my cock of its own accord, and I began to rub up and down, slowly at first. Once I’d begun, she pulled the panties down, all the way, and I saw her pussy, at the bottom tip of another tan line triangle. She was shaved bare, and her mound was beautiful jutting outwards just a little. The slit itself looked ...