The Chaperone

Sarah's POV

It's not unusual for a person to look forward to summer- barbecues, parties, no lengthy seminars in overcrowded lecture halls. But for me summer always meant vacation in the Adirondacks and even though I was 18 and it meant being several hours away from anyone I knew, I still looked forward to it just as much. Summer meant fresh mountain air, the close proximity to Lake George, and, most importantly, Kyle.

We started trips to the Adirondacks when I was four- me, my dad, my dad's business partner and his son Kyle. Kyle is eight years older than I am and the object of my affection for as long as I can remember. He has dark intense eyes and jet black hair which he usually keeps swept to the side. The best thing about him is his smile, which he doesn't do very often but when he does it travels all the way up to his eyes causing them to twinkle. During his later teen years I didn't see much of him; even though he came to the Adirondacks he was always going off with loud groups of kids that I didn't know and coming home smelling strongly of beer. But the last few years he has been different, quieter. Dad says he has "sowed his wild oats".

This summer was also going to be different because Dad and Mr. Silver (Kyle's dad)'s business required them to spend a month in Europe negotiating a merger with another company. For a while, it looked like I was going to have to stay in my hometown but then Kyle offered to "babysit" me so that we both got to enjoy the summers to which we were so accustomed.

My reaction to this was mixed. Part of them groaned inwardly, mortified at the thought of being seen as nothing but a kid. The other part of me was thrilled. Just me and Kyle. I'd have him to myself for weeks.

I drove up to the cabin one day in early August. Kyle had already been there for several days and the house contained plenty of evidence that it was home to a bachelor. Beer bottles littered the kitchen counter and cans spilled out of the overflowing recycling bin. The bedroom at the end of the hallway (traditionally Kyle's) was overflowing with clothes, creating a trail leading out to the hallway. Kyle was nowhere to be found and not wanting to be a burden, I immediately set to work cleaning. After I cleaned the kitchen, I took a few tentative steps into Kyle's room. I hadn't seen Kyle in months and I took a few deep breaths, inhaling the distinct aroma that was Kyle's- a combination of male muskiness, deodorant and a faint trace of cologne. I took a seat on the bed and picked up one of his inside out sweatshirts.

"Sarah watcha doing?" I practically pissed myself. There was Kyle, standing in the doorway with an amused but quizzical expression. His hair had grown longer and it covered more of his face, concealing his expression and making it harder to read. I jumped to my feet. Oh God, how was I going to talk my way out of this one?

"Kyle! Hey!" I said trying to sound casual while trying to think quickly.

"Sorry to be in here. I was looking for...a sweatshirt," I held it up hoping it wasn't completely see through.

"Forgot how chilly it could be up here? Well, come on Sarah give me a hug," he pulled me in for a hug, nothing overly touchy, the kind two cousins might give each other. Yet I felt my heart pounding anyway and prayed he couldn't hear it.

We spent a few hours catching up in the kitchen while he heated up some cold pizza. I was flattered when he offered me a beer, telling me it would be our little secret. Clearly he didn't think of me as a little kid anymore. I tried to look cool and sophisticated sipping at the beer even though I had only drank once or twice and the taste still felt kind of alien to me. After dinner, he suggested a fire in the pit outside.

"You sure you wouldn't rather go out with your friends or something?" I asked him, not wanting to be a burden. He smiled.

"Of course, Sarah. I haven't seen you in months. I want to spend time with you,"

The words (said in his deep voice which always had a touch of huskiness to it) sent tingles down my spine and into other places. Maybe it was the beer but I was feeling very warm, a heat beginning in my lower stomach and spreading throughout my body. I got to my feet, trying not to sway.

"Sure, just let me change into something else," I said and left the room, convinced he could see my knees shaking nervously and hoping he couldn't tell that I wanted nothing more than him to push me back onto the table and fuck me.

Kyle

I consider myself to be a man of considerable self-control. Which is why I wasn't worried about being left alone for several weeks with an attractive young girl who obviously had a crush on me. But I have to say my resolve wavered slightly when I saw her in my room, on my bed, holding my sweatshirt. I had watched her for several minutes hungrily examining all the curves in her young body while I had the chance. I wasn't exactly sure when Sarah had blossomed- there were quite a few years when I had been distracted with girls of my own and a wild college life.

But one day I turned around and instead of the awkward little girl, I saw a young woman in every sense of the word. Large breasts proudly jutted forth from her chest, something I'm sure she was a little self-conscious about at first as she tried to conceal them with sweatshirts and baggy shirts. As she grew more comfortable in her skin, her shirts grew more form fitting. Like today.

She was wearing a fairly modest but well fitting V-neck shirt exposing the very tops of her breasts. They bounced slightly when she walked and I struggled to not look at them. The rest of Sarah was on the smaller side but she had shapely hips and a nice firm ass which I couldn't help but check out when she turned around. What guy wouldn't?

Now it was just the two of us under the stars. She was seated directly next to me and if I was discreet I could see directly down her shirt. She wore a pink lace bra which did a pretty adequate job of hiding her breasts but I still felt the familiar stirring in my groin and had to stare at the grill for several minutes until it went away.

"So how's Roger? Are you still with him?" Roger was Sarah's last boyfriend- he had dropped by last summer and stayed for several nights in a nearby hotel. He was a nice enough guy but in my personal opinion sort of dull. Intelligence wise, there was no way he could keep up with Sarah.

"Nah we broke up a while ago"

"Sucks," I said taking a sip of beer and trying to look sympathetic. On some level, I knew I was pleased though.

"Nah its cool. We weren't compatible".

"Intellectually?" I asked taking another sip.

"Sexually," she said. I almost spit out my beer. Seeing the shocked look on my face, she backtracked quickly.

"Sorry," she said. I detected a slight slur to her words and decided the beer had gone to her head faster than she had expected.

"Nah, it's cool. You can talk to me about this stuff," I heard my own words and they sounded strange to me. Maybe I was a little drunk myself. "I'm sorry if he pressured you. Guys can be dicks that way".

"No...it was kind of the other way around," I looked over at her and noticed her staring at the ground, biting a lip an embarrassed look on her face.

"How do you mean? You can tell me," I repeated, trying to sound reassuring. I was just trying to help her out. Like a confidant, like a friend.

"He thought I was wild...like sexually," At this I burst out laughing. Sarah? Wild? Right now she looked the perfect picture of the innocent schoolgirl.

Sarah looked indignant. "I'm not as innocent as you might think!" she said heatedly.

"Okay," I said smirking "Well what made you wild? What was so crazy he wouldn't do?" Now she looked uncertain again. I smiled, trying to look reassuring.

"I wanted him to...you know," I shook my head, indicating my confusion "eat me. Down there".

She lowered her eyes, clearly embarrassed.

"Your pussy? He wouldn't do that?" I asked. What a dick! "But I bet he liked it when you sucked him off," She blushed again.

"Yeah but...well it wasn't just that. I wanted other things".

"Like?"

"Anal," she whispered "I wanted him to kiss my...and then..."

Jesus Christ, my member was growing hard at the very idea. I pictured pulling her cheeks apart, lowering my lips to delicious ass, inhaling her scent. She was still talking, clearly afraid that once she stopped she wouldn't be able to continue.

"And there's other things but...I can't really talk about it. Actually I shouldn't be talking about all this to begin with. I'm an idiot. I'm sorry."

"No, it's fine," I croaked. God dammit my mouth was dry. It felt like sandpaper "but I've had a long day and the fire's almost dead anyway. I think I'm going to head to bed".

She looked hurt and I realized how it must have felt for her to expose herself like that. Shifting one arm over my groin area so she would not see my hard-on, I used the other hand to tilt her head up so that her eyes met mine.

"Hey," I said softly "You have nothing to be afraid of. Someday you will meet a guy whose into all that. And trust me there will be plenty of guys. And the guy you choose will be very lucky".

As our eyes met it felt like there was a current of electricity flowing between us. I heard her breathing deepen. I tore my gaze away and got to my feet.

As soon as I closed my bedroom door behind me, I watched porn and touched myself, determined to get Sarah's face out of my head.

Around midnight I was on my way back from the bathroom when I passed Sarah's door which was opened a small crack. What I saw stopped me dead in my tracks. Sarah lay on the bed, legs wide apart, a tank top stretched over her voluptuous breasts, her hand between her legs as she stroked herself fervently. I was captivated. All I could do was watch as she stroked herself, her head back on her pillow, her eyes closed in pleasure, her cheeks flushed.

She let out a slight moan and slipped one finger, then two inside herself. She was clearly wet because her fingers slid in with ease. As she inserted a third finger, I heard the squelching sound of her pussy. She wasn't shaved, but neatly trimmed and even from the doorway I could see the edges of her thighs, glistening with her juices. Perfection.

"Kyle," she murmured. Oh sweet Jesus, I almost came in my pants right then. Sure, I knew she was attracted to me but I never knew she fantasized about me. She moved suddenly and I jumped back, out of sight, sure I was caught. After several minutes I stepped forward nervously. She had her head down in the pillow, her tight little ass in the air. As I watched she took one finger (clearly lubricated with her own juices) and fucked herself, slowly at first then faster. She inserted a second finger and I heard her breath coming in small little gasps as she became more and more excited.

I wanted to stay and watch but I knew that staying any longer was risking being caught. And if she did catch me, if she did look at me with her eyes, heavy with lust, I don't know if I would be able to control myself. Now that I know how much her body wanted me, I became aware of how much my body wanted her as well. I fell into bed, my cock erect and I immediately began to touch myself, my thoughts filled with nothing but Sarah. Sarah and her little mouth taking in the length of my dick, Sarah and her wet pussy waiting for me to plow her, Sarah and her tight ass stretching to accommodate my cock. I was past caring. I shot my load all over the bed picturing it covering her giant tits. Then I closed my eyes, exhausted, feeling a mix of both guilt and satisfaction.

Sarah

Kyle and I spent the next week as companionable housemates. We exchanged small talk over meals, we sometimes enjoyed baseball games together, but we never came close to that energy exchange we had the first night. I was beginning to suspect he was actually avoiding me- he avoided all types of physical contact with me, sometimes deliberately taking the long way around the table to avoid brushing against me. I felt embarrassed, knowing my confessions the first night had probably embarrassed him. He probably thought I was pathetic. Or worse, a pervert. Or a stalker.

On the bright side, I began to get closer with the family renting the cabin next to us. An elderly couple and their grandchildren- 21 year old Lori and 24 year old Ian. I liked them both at once. Lori was vivacious, friendly, and kind of wild. She filled me in on all her crazy escapades, usually involving booze, boys or both.

Ian was also outgoing but in a different sort of way. He liked my body and made sure I knew it. The first time Lori and I were stretched out on the beach sunbathing I caught him staring at my tank top which barely stretched over my boobs. Instead of looking embarrassed or looking away, he winked and gave me this naughty smirk and immediately I felt this familiar wetness between my legs.

Friday night (about a week after I arrived) Lori invited me to go with her and Ian to a party in town. I was hesitant. Kyle was pretty cool about me drinking beer at the house but in other ways he was kind of strict- calling me frequently, giving me the third degree about who I was hanging out with and even waiting up for me. So Friday I went to bed early with a headache, turned off my light and crawled out of the first story window where I then ran to Ian's waiting car. Lori had already helped me to pick out the perfect outfit- something a bit more revealing than I was used to but I relished how sexy it made me feel and the way Ian stared appreciatively as I climbed into the backseat of the car.

Lori and I had a fun time at the party, although there was no way I could keep up with her and barely even tried. She did about five jello shots, downed three beers, puked twice then went on the trampoline, then puked again. I stuck to beer and even though I ended up holding her hair while she vomited all over herself, it was still a thrilling night for me. Ian mostly stayed with a group of guys playing cards and smoking pot in the corner of the room. Several times I felt his eyes on me and it thrilled me. The alcohol gave me confidence and sometimes when I walked past him I gave him a flirty smile or a wink.

We left the party around four in the morning with Lori passed out in the backseat. Ian cleared his throat, breaking the silence.

"So...did you have fun?"

"Yeah," I said, trying to sound casual "Did you?"

"Yeah," he said, then glanced at me "Have I mentioned how much I like your outfit?" I smiled and felt myself blush.

"Thanks," I said ducking my head. By this time we had arrived at his house. We pulled into the driveway and he put the car in park. We didn't move.

"Don't act shy with me." he whispered, his eyes locked on me "You're wild aren't you little one?"

I'm not sure what would have happened if there hadn't been an angry rapping on the window. I looked up startled and found myself staring into Kyle's furious eyes.

Kyle

There have been very few moments of genuine panic in my life which is why tonight will stand out as one of the most painful nights of my life. Sarah was acting strangely all day and when she went to bed early with a "headache", I felt bad. I felt like maybe I had hurt her feelings. She probably thought I was uncomfortable about the other night. And I was...but for reasons she knew nothing about. Everything about Sarah took me back to that night- even if she was doing something as innocent as chopping peppers I stared at her fingers and imagined them drenched in her pussy juices. Consequently, I walked around in a state of permanent horniness. But maybe I had been too standoffish. She had been spending a lot of time with the kids next door which I was not happy with. Lori was pretty wild. And Ian- well I'd seen the way he looked at her. Hungry, like he wanted to devour her. When he did this I felt a combination of jealousy and further horniness. So Friday, I decided there would be no harm in bringing her a cup of tea.

But when I flipped on the light switch her bed lay empty, neatly made, like it hadn't been slept in at all. I immediately tried calling her and when I got no response I went next door, heart pounding. I had no idea where she was. Lori's mom (a sweet old lady who obviously had no idea what kind of antics her daughter got up to) told me she had heard Lori and Ian talking about a party and maybe they had taken Sarah with her. I was torn between calling Sarah's dad or waiting for Sarah to return. In the end I decided I'd wait for her to return, giving her a chance to explain herself. I spent an agonizing night waiting up for Sarah. Every time I heard a car outside I ran to the window, disappointed when the beams of the car disappeared around the corner.

Finally, at some ungodly hour, I spotted a car in the next driveway. I immediately stormed out of the house, a mix of fury and concern. When I saw Sarah sitting in the passenger seat, I felt an intense wave of relief somewhat overshadowed by my anger at the way Ian had his eyes locked on her. There was no mistaking his intentions. When I rapped on the window, she paled, all the color leaving her face. Ian, for his part, looked terrified. That, at least, was somewhat mollifying.

"Get in the house. Now," I snarled. Still an eerie shade of white, she scrambled out of the car and into the house. For a moment I could only stare at her, taking in the outfit she had on. It showed off every inch of her curves, leaving no illusion to the large size of her breasts or the curve of her hips. It barely stopped below her ass and her top dipped dangerously revealing the top of a lacy black bra. In short, she looked like a stripper.

I wasn't really thinking when I took her over my knee and flipped her skirt up revealing black lace panties snugly hugging her ass. It was a beautiful sight. I began to spank her, giving her several hard swats on each cheek. She squealed and I knew how mortifying it must be for her to be spanked like some errant child. She wanted to be seen as some mature woman and instead she was sprawled across my knee fighting to hold back sobs.

The spanking, intended to punish her, was having an interesting effect on me. I felt my cock began to stir as I watched her ass ripple with every swat and felt her tits bounce with the force of my hits. I yanked down her panties and continued to hit her, enjoying the rosy glow of her ass cheeks.

"What were you thinking, going out like that, dressed like some common slut?" At my words I heard a sharp intake of breath and felt her wriggle against me with a moan. I suddenly realized I was not the only one enjoying this. I felt her squirm as she struggled to press her clit against my legs. I immediately stopped, afraid she would discover how hard I was.

Sarah got to her feet unsteadily. Her face was bright red and she scrambled to pull up her panties but not before I got another glimpse of her neatly trimmed pussy.

"Kyle, I'm sorry. Please don't tell my dad!"

"Just go to bed. We'll talk about it tomorrow," I was way too flustered to deal with this now when all I wanted to do was throw her onto the kitchen table and ravish her. But I felt that wouldn't really be an appropriate way to deal with the situation.

I stayed downstairs a while longer, trying to regain my composure. When I got to the top of the stairs I heard the shower running and saw that Sarah's door was wide open, her panties lying on top of her skirt. Glancing down the hall towards the bathroom and still hearing the water running, I entered Sarah's room, holding my breath with every step. I picked up her panties and discovered that they were soaking, completely drenched in her pussy juices.

I held them to my nose and inhaled deeply. I thought I was going to cum right there, as I closed my eyes yearning to bury my face in her pussy and hear her squeals of delight. I imagined her face as I ate out her pussy and wondered how her ex boyfriend could have been so stupid. What an opportunity he missed out on.