Jack Learns to Jerk Off - Sex Stories

Jack Learns to Jerk Off

... more memories of whatever she had been doing, as she went and sat on my bed. “Hey...” she said. “I'm... sorry you had to see that.” “I...” I began, “It's okay.” It wasn't exactly okay. &#034We both know what you saw. It's nothing you should feel ashamed for.&#034 But it was. I turned away from her in my embarrassment. “I mean, masturbation is only normal and all, and I just had a bit of pent up-” “Master-what?” I asked, cutting her off. I turned around sharply in my chair. She looked at me in shock. “Wait, Jack, you're telling me you've never heard of masturbation?” She asked. I shrugged my shoulders in confirmation, amazed she even talked to me at all. “Oh...” she said slowly. “Okay, well, I guess I think it'll help if I explain what I was doing. You might understand that way. If not, well, we don't have to speak to each other for the rest of the week.” “Okay then.” I said, hoping this may just help and silently having a bit of curiosity for the female anatomy. “Well, you see,” she said, “I was masturbating, which is a way to make yourself feel good by rubbing yourself... down there. When you do it for a while, eventually, you have an orgasm, which is this thing where wave after wave of endless pleasure floods your body.” “That sounds really dirty!” I said, getting red in the face. “It is. Extremely so. But,” she continued, “it's a way to relieve sexual stress, in a way. Everybody does it, guys and girls.” “Should I be doing it?” I asked, growing somewhat more comfortable ...

... with all that she was saying. “That's really up to you, little b*****r.” She said. “Well, how would I do it?” I asked her. “Uhh...” she began, “well, I don't know. You'll have to ask someone else.&#034 &#034But everyone's out of town!&#034 I exclaimed. &#034Ugh, you're right.&#034 She sighed. &#034Who then to teach my little b*o how to blow his load?&#034 “Could... could you teach me?” I beamed. “Um...” she stopped. &#034I don't think that's... Okay.&#034 &#034You said it feels really good though! Please?&#034 &#034Ugh, a... Alright. If I teach you, you have to promise that we never speak of it again, you got it? Because this is some sexual stuff here, and i****t is super i*****l, but I don't se it as a huge crime if I'm just teaching you how to jack off.” “I promise, big s*s. So what's first?” I asked her. “Well, you'll wanna strip down. All your clothes.” She commanded. I followed her order. First I removed my shirt, then my pants. When I was down to my boxers, I stopped, and looked up at her. “Is it okay to be naked in front of you?” I asked her. “Of course, just for this.” She told me. I nodded, and slid my boxers down slowly. Then I popped back up and stood there, naked. “Good,” she continued. “Now go lay down on your bed.” I did so. I was actually excited to see what was next. This would be like my little secret thing. I was now down on the bed, my legs spread a little so that my balls drooped down a little. I turned to look at my s****r. She had zoned out while looking ...