Confessions of a Teenage Nympho

Chapter 6: Pleasant Surprises

My brother avoided me for the rest of the time I was home for the holiday. I tried to talk to him, but he wasn't ready to discuss what had happened between us. I tried to be understanding, but it hurt that he wouldn't talk about it. So I gave him his space and just kept making an effort to let him know I wasn't bothered by it and that I wish he'd talk to me.

I decided while I was home, I was going to hang out with my friends and have a good time. I wasn't going to dwell on it and when Jason was ready to talk, we'd talk. So I called up my friend Hailey and we decided to hang out that night at her place while her parents were up in Vermont visiting her aunt. I hadn't seen Hailey since the summer after graduation so we had plenty of catching up to do.

When I knocked on the door, Hailey's younger brother Aaron answered the door. "Hey, where's Hailey?" I asked. He moved out of the way, watching me walk by him.

"In the kitchen," Aaron said, watching me walk up the stairs of the raised ranch home and straight ahead to the kitchen. I looked back and flashed him a smile.

"Boo!" I shouted to Hailey who had her back turned, pouring some dip into a bowl on the counter.

She let out a shriek and spun around. "Lindsey!" she shouted smiling as she caught her breath. She flung her arms around my neck and gave me a big hug. "I've missed you!"

"Missed you too!" I said, hugging back.

Aaron walked through the kitchen towards the outside deck. "Get a room!" he muttered as he passed us. He went out onto the deck, closing the sliding door behind him.

"So how's things?" she asked, emptying a bag of chips into a larger bowl as I took a seat on one of the stools at the kitchen island.

"They're ok. School's going good. I'm staying afloat," I said. I definitely needed this break though. "How are things here?"

She shrugged as she pushed the bowl to the center of us, and pulled up another stool to sit. "They're ok," she said. "I wish I had gone away for college like you. I hate this town and I hate the college."

I laughed. "I'm not that far. I'm only in Boston," I said.

"Yeah, but going to college in our hometown? It sucks," she said. "I just wish I had gone to the city instead, or even further away."

"Family driving you nuts?" I asked, dipping a chip and munching on it.

She nodded. "My mom and dad are thinking about selling the house and moving out of state, which I definitely don't want to do, but I can't really afford to stay and get a place by myself? I could get an apartment with Aaron because he wants to finish high school here, but we'd drive each other insane!"

I laughed, somewhat awkwardly to myself, thinking about my own brother, and wondering if Hailey and Aaron would end up in a similar situation if they lived together. "Well, next year I'm probably going to get an apartment with a couple of my roommates, as opposed to living in the dorms, so maybe you could move in with us. You could transfer credits to a school in Boston, or just take the commuter rail to school here," I suggested.

"That would be so awesome," she said. We snacked on chips and dip for awhile, catching up on town gossip, and reminiscing about high school days. We both agreed that as you get older, you start to miss what you had, and wish that you had taken full advantage of your youth.

"You know what we should do?" Hailey asked, suddenly getting excited.

"What?" I asked laughing at her reaction.

"We should have a sleepover!" she said. I laughed. "I mean it. We'll get out the old sleeping bags, and we'll watch scary movies in the living room and make cookies or something!" She was really into the idea. And I had to admit, so was I.

"Ok! Let's do it!" I said. I was excited to relive our childhood in her living room. We used to do that all the time, and it was a blast.

That night, we ordered pizza and laid out a couple of sleeping bags in the living room. We popped in the remake of "Prom Night" and curled up eating popcorn. The movie wasn't that great and soon, Hailey yawned and turned over, falling asleep. I shut off the movie and tried to do the same. Suddenly, I heard a noise and my eyes flew open. It was in the kitchen. Someone was up and getting a drink. I heard the refrigerator door open and close.

I laid there trying to stay silent as I heard footsteps come closer towards the living room. I closed my eyes and readjusted myself so that my cut off t-shirt was riding up my chest a little bit. I laid there with my arms stretched above my head and gave whoever it was a nice view of my slender neckline. I heard a gasp of breath and some rustling. Then I heard a zipper slowly lower.

Beneath the sleeping bag, my hand caressed my stomach and slid beneath my panties as I thought about being watched. I heard a soft groan, and shifted to try and hike my shirt up a little bit more. I licked my lips "in my sleep", and let out a soft sigh. I heard the voyeur stroking himself. The sound of his balls slapping lightly against his thighs was the only sound in the room. I didn't want whoever it was to wake Hailey up, so I shifted my position and heard him fumble with his pants to put his penis away.

I fell silent again and listened for him. He was trying to be silent but I could hear his breath heavy and nervous. As I rolled over on my side, the open side of the sleeping bag parted and I heard him gasp as my slender back and the smooth curves of my ass came into his view. The panties had shifted down somewhat and I was sure he could see the enticing cut between my cheeks. I turned, and opened my eyes, but I couldn't see anything. My eyes weren't adjusted, and I could only make out the shadow of my viewer as I suddenly heard him grunt softly. He gasped as he saw my eyes opened and quickly turned and scurried away down the hall.

I smiled to myself as my middle finger grazed over my wet slick clit. I curled my finger up inside my pussy and held myself tight, fantasizing about what just happened. But I was unfulfilled. I wanted a cock. That bastard came out here, jacked off while he watched me sleep, and then just went to bed. What about me? Getting me all wet and turned on, and then leaving.

I looked over to Hailey who was sound asleep. I pushed the sleeping bag down and crawled out , standing up slowly. I tried to be as quiet as possible as I crept down the hallway. I bet it was Aaron. I saw the way he looked at me when I got there. I stopped in front of his bedroom door. It was open a crack. I pushed gently and the door opened more.

I could just make out the image of him laying in bed, through the darkness. Looks like it was his turn to fake being asleep, but he had another thing coming if he though I was just going to stand there playing with myself while I watched him. No way. I pushed the door a little more and he didn't move. He just laid there, sprawled out on his back with his arms stretched. A thin sheet covered his legs and waist, his bare chest uncovered.

I stepped into his room silently, turning and closing the door slowly. I looked back over to him, the red glow of his alarm clock the only light in the room, illuminating the side of his face and stretching across his chest. I reached down and pulled my shirt above my head, dropping it to the floor. I reached down and pushed the edges of my panties over my ass and they dropped down to the ground at my feet. I stepped out of them and tip-toed slowly over to the foot of the bed, careful not to step on anything that might be strewn across the floor.

When I reached the foot of the bed, I reached down and grabbed the bottom of the sheet, lifting it and bending down to crawl under. With the sheet dropping over me, I slowly crawled up the bed, careful not to wake him if he was really asleep. I could feel the heat radiating from his spread legs as I crawled between them. When I got halfway up his body I stopped. I couldn't see a thing, but I knew that my face was now hovering over his dick. I could smell the strong musky scent of his manhood and I bent lower, pushing my ass up creating a tent with the sheets.

I slid my hand between his legs slowly and found him sleeping naked, my hand running over his balls and up the edge of his flaccid cock. It wasn't very big, but then again, he was younger than us. I smiled and licked my lips as I held it upwards and opened my mouth, guiding it inside in the dark. It was warm and soft in my mouth and I pushed my tongue up and down all around it. I took the whole thing in and sucked hard, pulling upwards, my lips sliding up to the head, then slamming back down on it and engulfing the entire thing in my mouth.

I heard a sigh come from him and his arms moved, stretching into another position as I continued to work his cock. It didn't take long for him to get hard, and soon my mouth was widening as his girth built to a normal size. I licked the shaft sideways, my mouth wet as I worked his cock with my mouth, holding the base with one hand. My other hand reached underneath me and tickled my pussy. I slid a finger in and out as I bobbed a little faster on his dick.

I felt movement, and soon felt Aaron's hands grab a handful of my hair and press down on my head, guiding me to the pace he wanted. He was awake now, and I was curious as to who he thought it was sucking his cock under the sheets. I wondered if Hailey had ever woken her brother up this way, or if he knew for sure it was me.

I could taste his sweet pre-cum leaking out as I continued working his dick in and out of my mouth, guided by his firm grip on my head. He pressed me down and I deep throated him without gagging. He wasn't very long, but the thickness was nice. He humped upwards at my mouth and I felt his balls tighten. I pulled myself off of him, pushing hard against his resisting hands. I heard him grumble, as he realized I wasn't going to take his cum.

"Uh-uh," I whispered to him, as I moved up his body and emerged from the sheets. His cock slid against my stomach and grazed my pussy lips as I moved above him, spreading my legs to straddle his body. I held my hips above him, letting them hover over his cock. "Not yet," I said softly.

"Lindsey?" he asked as I grabbed his wrists and pinned them down on the bed on the sides of his head.

"Uh-huh," I whispered as I leaned down and licked his lips, catching his bottom lip in between my teeth and giving them a soft tug.

"Holy shit!" he said. I could almost hear his mouth smile widely at the thought of what was happening. He arched his back, pressing his body against me. I felt a shiver run through him as my nipples grazed his chest and his cock found itself pressed between my thighs, the shaft resting on the length of my slit.

"You want it?" I asked, kissing his cheek, and leaving a trail of light kisses down to his ear and neck.

I felt him nod aggressively. "Hell yes!" he said, louder than he thought he was being. I moved my hips up and down, grinding my wetness against his rigid cock. It throbbed against my clit and I couldn't hold back and longer. I manipulated his cock with my body, positioning the head against my opening and pushed. It pressed inward against my lips and finally passed through them to my opening. I let the head slip past the ring and inside, and he groaned at the heat on his cockhead. Slowly I sank lower, letting it slide inch by inch deeper inside me. His breath was heavy and he pushed upwards, our thighs meeting as he entered me completely.

I squeezed the walls of my cunt around his cock, gripping it tightly. He let out a moan. "You like that?" I asked in a teasing whisper. "A lot better than jacking off while you watch me sleep, isn't it?" I rocked up and down on his cock, clenching it with my pussy each time I impaled myself on it. He didn't answer. He must have been too caught up in the moment.

I let his hands go and slid my hands down his chest, grazing through the curly hair that lightly covered the center of his chest. I pressed my hands flat on his chest firmly, sitting upwards to give myself better leverage to slowly rock up and down on him. As soon as I had let go of his wrists and sat up, his hands were on the small globes of my ass, squeezing tightly and guiding my hips up and down as he continued thrusting up to meet me.

My wetness leaked down his cock and through his pubes. His balls, now soaked with the sweet sticky nectar he was forcing me to produce, pressed against my ass with each thrust. I was so wet, fucking this younger guy. My best friend's younger brother. I thought of how innocent he was, now losing that innocence to me. Though he wasn't really that innocent. No boy is.

I rose up a bit higher than I wanted to and his cock slipped out of my pussy. It was rock solid, however, and stuck straight up, pointed at my holes. As I went to impale myself back on it, it slipped against my pussy lips and about 2 inches of it slid inside my ass. Both his cock and my asshole had been so wet from my cum that it slipped in effortlessly.

I stopped before it slid completely in, almost collapsing from the shock onto his chest. The sudden blast of pain shot through my body instantly and I almost screamed. I, myself, froze, not knowing what to do. I didn't want to just yank myself off of him, but I also didn't want to push more of it inside me. "What's wrong? What happened?" he asked me, his hands still gripping my ass and spreading my cheeks apart.

"You're in my ass!" I whispered loudly.

"Oh my god! I'm so sorry!" he whispered back. He started to move, but I pressed my hands against his chest, pushing him back down on the bed.

"Don't move," I said. "It's ok. I did it by accident. It's my fault." Suddenly, I realized that the pain was gone. His cock was a third of the way inside my backdoor and it was starting to feel good. As the walls of my ass had stretched and were slowly getting used to the feeling of him inside me, I decided that I wanted more. I had never done anal and always wanted to. At least his cock was a normal size and wouldn't hurt as bad as one of the larger ones my pussy had had the pleasure of milking.

I switched back into naughty mode. "You want it?" I asked. "You want my ass you dirty little perv?" I teased, pressing back against his cock letting another third of the length slide up into me. I groaned and he grunted at the tightness. His hands spread my cheeks and without warning he took control and slammed the rest of his cock up my ass and held me down on it forcefully.

I let out a low groan, my pussy soaking his abdomen as I came hard. With one hand on his chest to steady myself, I reached down with the other one and furiously rubbed my clit. I squeezed and contracted my muscles and he grunted again as he felt my ass grip his cock tight. He pulled his cock halfway out and then pushed back in.

The pain was now a mixture of discomfort and an immense pleasure. It was hard to wrap my mind around the mixture of emotions I was feeling. As he slowly but steadily began pumping in and out of my tight pink asshole, his cock stretching me, another orgasm built from deep inside of me. I panted as he began to pump harder and faster, pistoning in and out of my ass as I diddled my clit and let out a low moan. It was overwhelming. I came so hard again, gushing clear sweet cum which covered his stomach and my thighs. I fought to catch my breath, my hand pulling away from my cunt and clutching my heaving chest. I shuddered and shook, tears streaming down my face as I whimpered loudly.

He thrust hard, and I heard him grunting roughly as he gave one hard fucking motion with his cock, slamming it up inside me as deep as it would go before pumping shot after shot of thick cum inside my ass. I continued to ride my lengthy orgasm as I felt his cock throb as it unloaded his sticky wet balls up inside me, filling me up. I felt his cum leak out past his pulsing dick and trickle down to mix with mine.

My body contined to shiver and shake as I came down from my orgasm. We both breathed heavily, panting and dripping with sweat and cum. He slid his cock out of my ass and it rested on my ass cheeks. My hole was sore, but it was worth it. It felt amazing. I collapsed onto him, resting my head on his chest.

"That was fucking amazing!" I said to him as I curled up and rested, catching my breath. My head rose and fell in time with his chest and I curled my fingers through his chest hair. I wrapped my leg around him as I my body melted off of his and I laid beside him resting on his chest for what seemed like hours. He held me in his arms in the silence, the discomfort and slight pain of my freshly abused ass slowly subsided.

I looked over at the clock after awhile and saw that it was 4:30AM. I slowly sat up and his hand touched mine. "I have to go back to the living room. I don't want your sister waking up to find us like this," I whispered. He sat up as I pushed off the edge of the bed to stand. My legs were weak and I leaned my hand on the bedside for stability as I tried to regain my composure.

I made my way slowly across the room to the door and reached down, grabbing my clothes. I redressed and tip-toed back to his bed. Leaning down, I caressed his face and we kissed for the first time. It was soft and sweet and when I pulled away, I whispered, "Thank you. That was incredible." He smiled and I kissed his cheek one last time before turning and making my way back to the door.

As I turned to close it behind me, I whispered to him, "Good night." I tip-toed back to the living room and crawled back into my sleeping bag. I was still feeling light-headed as I laid back, covering myself up good this time. I didn't want the scent of me and Aaron's cum lingering in the air for Hailey so smell. I turned over and closed my eyes, exhausted.

In the morning, we woke up and Hailey's father made us breakfast. As I sat at the table next to Hailey, Aaron walked in and flashed a smile at me as he reached into the fridge for some orange juice. He sat across from me and looked at me with hungry eyes. His bare feet caressed the edge of my ankle under the table and I gave him a light kick. I smirked at him and glared, motioning slightly to Hailey. He smirked back and we stopped our little dance for the time being.

Later, when I was getting ready to leave, I brushed my teeth in the bathroom and as I was walking by the laundry room, I saw Hailey's dad standing in front of the open washing machine. He had been loading laundry, but stopped, holding up my sleeping bag. He raised it to his face and inhaled deeply, taking in the smell I left behind. He moaned as he exhaled and suddenly he froze as he saw me watching him. I smiled and his eyes widened.

I was about to turn around and walk away when he said, "I'm sorry about last night Lindsey. I know you saw me watching you, and I apologize. I couldn't help it." He shook with nervousness, and I raised my hand above me using it to lean on the door frame to catch my balance. It was him that had watched me and jerked off in the living room. Not Aaron! I was shocked. Hailey's dad had cum while watching me sleep.

I saw how nervous he was while he apologized and suddenly found myself feeling bad. I looked behind me up and down the hallway. No one was around. I slowly walked forward towards him. He froze, dropping the sleeping bag. I pressed myself against him, reaching down to grab his cock through his pajama pants. I felt the thickness and length of it began to get harder. I looked up at him with my baby blue eyes wide and innocent and I bit my lower lip. I leaned up and pressed my cheek against his as I whispered in his ear, "Next time I sleep over, don't let me catch you jacking off." I looked into his eyes as I pulled away. "There's no need to waste a perfectly good load of hot daddy cum by stroking this big thick cock, when my wet pussy would feel so much better wrapped around it than your own hands do." His mouth gaped open and his eyes were wide with shock. I gave his now hard cock a tight squeeze around the shaft through his pajamas and turned around, walking away.