Date: Tue, 04 Apr 2023 01:44:52 +0000 From: Clay Fox Subject: A Night to Remember with My Stepsister's Boyfriend The people, places, and events described are fictional. If you like the story support the Nifty archive by donating. If you want to contact me drop a note to . Feedback is always appreciated. * * * * * * * * * * My older step-sister Tracey isn't exactly a great role model for me. She smokes cigarettes, drinks booze, and hangs out with the bad boys at our school. Except for our blonde hair, she's the complete opposite of me - I'm shy, reserved, and not very popular. But for some reason, I can't help but be fascinated by her wild lifestyle. For her 14th birthday Tracey wanted to have a big sleepover party with all of her friends - girls AND boys. But our parents only agreed to let Tracey's new boyfriend, Dale, come over if he slept in my room. I didn't mind, but I was nervous about having to share my space with a guy I barely knew. I also couldn't believe my luck that my parents allowed me to join in on the party too. My name is Aaron, I'm 12 and just started seventh grade last month. I guess that I owe my sister some gratitude: her mean girl reputation probably stopped a lot of kids at school from bullying me. Tracey was a tough girl, and her friends were no different. She started dating Dale a month ago at the start of the school year, and he was a year older than her at 15. Once everyone arrived we had pizza and cake before Tracey announced that the girls were going upstairs to change into their PJs and give each other makeovers before joining us to play games. Sabrina was Tracey's best friend and a bit of a free spirit. Two other girls who I didn't know well were also invited. They all laughed at everything a little too loudly as they went upstairs. Dale and I headed down to my room to change as well. My room was nothing special, just a blue painted wall, a bunk bed, an old desk, and a Nirvana poster. Dale complimented me on my musical taste, and we started to change. I felt self-conscious about my Star Wars pajamas and hoped Dale wouldn't make fun of me for being too kiddie. I glanced over to try and discreetly watch Dale change. Dale was more developed than me, I could see his abs and the hairy tufts in his armpits as he took off his shirt. His hair was a dark brown and complemented his naturally tanned skin tone. I must've zoned out or something, because Dale noticed my hesitation to change and put a hand on my shoulder. "Hey man, don't worry about it. You'll catch up." His touch sent shivers down my spine, and I couldn't help but feel a little nervous around him. As I took off my shirt and jeans to change into pajamas, Dale noticed my Star Wars underwear and chuckled. "Those are pretty cool. Can I have them?" I hesitated, not sure what to say. The idea of Dale wearing my underwear made me feel weird, but I didn't want to disappoint him. "Uh, sure," I said, handing them over. I covered my junk so he wouldn't see that I didn't have much hair down there yet, and quickly slipped on my pajama pants. Dale slipped the briefs on over his sweats and did a little dance, making me laugh. I was surprised that they fit - Dale looked athletic but his abs were more likely the result of him being skinny instead of muscular. The briefs were tight and made his bulge looked enormous and obscene to me. Dale gave a little hip wiggle and then bent over to pick up his shirt so he could whirl it around like he was a Magic Mike stripper. Even though he had a reputation for being a bad-boy, I was happy to see him act silly. Dale tossed his sweaty shirt at my face. It smelled a bit like BO and deodorant, but I didn't find the smell unpleasant. Even though I was having fun, I couldn't shake the feeling that something was off. Dale seemed to be getting closer to me, and I didn't know how to handle it. "Did you enjoy the show?" Dale laughed and walked over to me. I turned bright red and could literally feel the heat coming out of my cheeks. "I love Star Wars, but I think we should change into something that will actually impress the girls." Dale mentioned that Sabrina had a crush on me, and insisted that I put one of his band t-shirts on and some gym shorts. We heard the girls rushing down the stairs, chattering about their excitement to play games with the boys. Dale tossed me some fresh clothes, and we quickly finished changing before joining the girls in the hangout space. Unfortunately I didn't actually get to see anything below the waist like I had wanted. The teens gathered in the basement, chatting, laughing, and playing music. Tracey put on some Pearl Jam, which I had never heard before. The music was loud, and the bass made the walls vibrate. Tracey and her friends were already drinking beer and smoking cigarettes. I watched as Tracey and her friends laughed and chatted in the basement. They were all older than me, and I felt like a kid amongst them. As I watched them, I felt a mixture of excitement and fear: I didn't know if he wanted to be part of this world or not. As the night went on, the party games began. We started playing truth or dare, and Sabrina spun the bottle. It landed on me, and I was nervous. My heart raced as she dared me to kiss Dale on the cheek. I hesitated, unsure if I wanted to do it. But Dale smiled and urged me on. I leaned in and pressed my lips against his cheek. It was a quick peck, but it sent a jolt of electricity through me. Dale laughed and said it was no big deal, but I couldn't shake the feeling that I wanted more. The game continued, and we ended up staying up late into the night. I had my first beer, smoked my first cigarette, and actually felt like I could be a cooler person than just Tracey's nerdy little brother. My head was swimming, but I felt great and the girls all made sure to talk to me. After a while, I don't know how long, the girls went upstairs to bed. Dale and I went back to my room and he laid down on the bed beside me. It was a bit cramped. "Hope you don't mind if I share the bed, I don't like the idea of either one of us sleeping in that old sleeping bag on the cold concrete floor." Dale took off his shirt and then turned on his side to look at me. Suddenly, Dale leaned in and kissed me on the lips. At first, I felt shocked and unsure, but as he continued to kiss me, I realize that this is what I'd been wanting all along. It was like a switch has flipped inside of me, and all of a sudden, I felt more alive than ever before. As he pulled away, Dale whispered "Fuck man, I have a serious case of blue balls." I could smell the alcohol on his breath and could still taste the memory of his tongue in my mouth. "Help me out," he whispered. I was still feeling giddy after our kiss, and I couldn't help myself from responding. I reached down and grabbed his crotch. He moaned softly as my fingers started to massage him through the smooth material his gym shorts. He grabbed my hand and placed it under the waistband, directly onto his dick. I could feel his hard length and bushy pubes, and I was thrilled to discover that he was bigger than I thought. I moved my hand lower and squeezed his balls, eliciting another moan from Dale. Dale rolled onto his back and pulled off his shorts, exposing his cock to me. The room was dark, so I couldn't see it clearly. Just a thick outline that curved slightly upwards. I was fascinated by how soft and hard it felt at the same time. I gripped his shaft firmly and gave it a few tugs. "Oh yeah, that's nice, keep stroking my dick, buddy!" I felt embarrassed at what I was doing, but I liked it. I started to move my hand up and down, faster and faster. I could hear Dale moaning loudly, and I realized that I was really getting turned on. "Dude. I need to bust a nut so bad." Dale whispered hoarsely. I figured he was doing his best to stay quiet and not wake anyone up. He grabbed my by the wrist and took it off his throbbing member. "I'm so close, I need you to suck my dick!" I was hesitant. I've never sucked a guy's dick before, in fact I had never even seen a hard one before tonight. I wasn't sure if I wanted to. But Dale was insistent. "Come on, dude. I know you want to. You won't regret it." Dale pulled me close and gave me another passionate kiss. It made my head spin, I couldn't believe such a cool guy would want to make out with me. "Just relax, and suck my cock little dude." Dale whispered into my ear. I took his advice. I slid down between his legs and could see his cock better now that my eyes had adjusted to the dark. He was uncircumcised just like me, but everything was a whole lot bigger down there, I licked Dale's shaft from the base to the tip, before closing my lips around his cock head. He tasted salty and musky, but I didn't care. I slowly bobbed my head up and down, taking more and more of his shaft into my mouth. His dick felt huge in my mouth, and I struggled to fit it all in. I started sucking harder, moving my tongue around his cock head in circles. I knew enough to cover my teeth from listening to older guys at school describe their first blowjobs. "That's it, man, keep going. Suck that cock for me!" Dale moaned. I tried to deep throat him, but I wasn't able to take even half of his length. He reached down and held my head in place as I sucked him off. I could tell he was close to cumming, because of his heavy breathing. Dale's dick was throbbing in my mouth, and it felt so hot. "Don't stop. Keep sucking me. I'm gonna fucking explode!" Dale moaned. I kept my head buried in his crotch as he continued to thrust his hips towards me, holding my head between his large teen hands. I felt his balls tighten close to his body and then release inside my mouth as he shot his load down my throat. He groaned loudly, and I tried to swallow every drop of his warm cum. I choked a little because of the bitter taste, but was able to take most of it. The rest of Dale's cum dripped off my chin and onto his stomach. He sighed deeply and fell back onto the bed next to me, exhausted. "Man, that was awesome. Thanks for sucking my dick buddy. You're the coolest dude ever." Dale laid back placing his arms behind his head. I crawled up and rested my his head on my chest. I could smell his manly aroma wafting from his bushy pits. My dick was hard as a rock inside the gym shorts Dale lent me, It pressed awkwardly against his leg. Dale reached down and fondled my stiff cock. "I should probably help you out with that since you were so good to me." I was surprised when he pulled my shorts down and started stroking my cock. "You have a nice one for your age. I'm not really into sucking cock so I'll jerk you off ok? It's only fair." It was the first time anyone had touched my cock. I was shocked at how good it felt, and soon I was on the verge of orgasm. Dale stopped jerking me off and laid down beside me, pulling me in close. My head was swimming in ecstasy. I caught another whiff of his pit smell and it drove me over the edge. "Fuuuuck! Oh fuck!" I grunted as I came all over his stomach. "That's it, come on man. Cum all over me." Dale moaned, almost in a trance. My body shook uncontrollably, my entire body felt like it was floating. Dale grabbed my shoulders and kissed me on the forehead. "That's for me, buddy. You're welcome." I was exhausted, and I could barely keep my eyes open. As we settled in, Dale pulled me in close and this time he didn't let go. My heart raced as I looked into his eyes, unsure of what was going to happen next. "Dude, can I be honest with you?" Dale said, his voice low and serious. I nodded, too nervous to speak. "I've had a crush on you for a while now. I know it's probably weird, but I can't help it. I see your cute butt in the halls at school and think you're amazing." My mind raced as I tried to process what he was saying. Was he really telling me he liked me? Did I like him back? If that's the case, why was he dating my sister? Before I could say anything, Dale leaned in and kissed me on the lips. It was a soft, gentle kiss, and I felt like my whole body was on fire. For a moment, I forgot about everything else and just let myself get lost in the moment. As we pulled away, Dale smiled at me. "I hope that's okay," he said.' I smiled back, feeling like a weight had been lifted off my shoulders. "Yeah," I said. "It's more than okay." We lay on the bed sweaty and sleepy from our experience. I confided in Dale about how I wanted to become cool like him, but didn't know how. Dale was surprised but flattered. He didn't think anyone ever looked up to him before. Dale talked about how tough his home life was and how he wished he could escape it. Aaron listened, feeling a kinship with Dale that he had never felt before. Dale fell asleep soon after, and Aaron lay awake, thinking about what he had learned. The next morning, my parents made pancakes for breakfast, and the group ate and chatted in the kitchen. As the sleepover party ended Aaron felt a mix of emotions. He was sad that it was over, but he also felt excited about what the future held. Dale gave me a wink as he left to go home.