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Judging Amy

Having Amy stay for the weekend was a horrible prospect.... but it didn't turn out so bad.
Judging Amy

Everyone was glad Amy was coming, everyone except me that was. It wasn’t that I hated my younger sister’s best friend, just that I was always unsettled around her. But, here I was, facing Amy’s company for two whole days before my sister flew in from Atlanta and my girlfriend headed off to Las Vegas for a girls’ weekend. Being alone with Amy for nearly two days did not fill me with enthusiasm.

“You should take Amy out to dinner tonight, take her into the city.” Carrie urged me as I drove her to the airport. For some unknown reason, Carrie had never viewed Amy with the same discomfort as I had.

“Yes.” I answered stoically. Nothing could have been further from my mind and there was no way I was going to do that!

It wasn’t that Amy was a horrible person, hell, she was pretty, vivacious and lively, it was just that for some reason she made me feel uncomfortable around her. It was nothing I could put my finger on specifically, but for sure the fact that she was so open about her sexual exploits, regardless of her company, probably had something to do with it.

I remember when she used to come to our family home and she would talk openly about what she would do with the male pop stars of the day. Later there would be lurid, mostly inappropriate, details of boyfriends. I recall seeing my father shake his head in wonder at the girl’s openness, and the fact that his daughter hung out with Amy. My sister had always maintained that I was judging her harshly, and that she was just a really nice, fun person, but I found it hard to change my opinion.

My sister and Amy had remained best friends even now they were at collage. They had planned a trip to Europe this summer and were meeting up at my house before setting off - Amy arriving two days before my sister, seemingly just to ruin my weekend and make me uncomfortable. Did I say that I wasn’t happy about this?

When I got back from the airport Amy was still sleeping so I quickly made some toast and set off out into the yard to do some chores. Two hours later I’d almost finished my yard work when Amy appeared on the patio, stretching and yawning in the tiny pink panties and string strapped vest she’d worn to bed. Her short black hair was tousled and her eyes were red with sleep, but it was hard to take my eyes away from her. She waved and I nodded back, not putting down the trimmer I was working with.

When I had put away the yard tools and dragged my sweaty self into the kitchen I found our guest slicing a banana into some oatmeal. “Morning Bob.” She had always called me that, even though I’ve always preferred “Rob”. She was just that kind of annoying girl.

I glanced at the clock on the wall. “Morning.” She was correct, but only by a few minutes. I grabbed a bottle of orange juice from the refrigerator and poured a glass. “What’s your plans for today?” I asked when I’d downed a long pull of the OJ.

“Nothing much.” Any spoke through a mouthful of breakfast. “Thought I’d just hang out here if that’s alright. Relax and read.”

I nodded my acquiescence and informed her, “I’m going to take a shower, then head out to run a few errands. I’ll be back later in the afternoon.” I didn’t want to open the door to her suggesting she came with me.

“Want me to make dinner?” She asked enthusiastically.

“It’s okay.” The last thing I wanted was an evening of college dorm cooking. I was only a few years away from having to endure that and happy about moving on. “I’ll grill a couple of steaks later.”

“Sounds good.” She picked up her bowl and walked to the patio doors. “Looks like a beautiful day.”

I shook my head as I looked at her, butt crack showing and oblivious. It was unlikely to be a good day for me.


It was almost 4:30 in the afternoon when I got home. I’d deliberately made the most of my time out of the house and two hours’ worth of errands had taken four hours. Amy didn’t appear to be in the house when I dumped a few shopping bags on the sofa and walked over to the patio doors.

She was lying on a lounger, eyes closed, forearms upturned to tan the underside and soaking up the early-summer sun… topless.

I took a step back from the glass, but continued to look for a few seconds. Amy’s lithe body was unmoving, her small breasts and stiff nipples drawing my gaze involuntarily. I shook my head, my every fear for the weekend confirmed, regardless of the vision presented to me. I saw it as nothing but bad manners on her part, not to mention a tease, whether she meant it or not.

I put away the few things I’d bought that afternoon and generally stayed away from the patio window until I heard it slide open. Amy walked into the kitchen wrapped in a towel. “How was your afternoon?”

“Fine. You just chilled?”

“Yep.” She pushed a large pair of sunglasses up her forehead to rest amongst her hair. “Read a bit, soaked up some sun… perfect. I’m just going to take a shower. That okay?”

“Sure.” I forced a smile. “I’ll get some food ready for… say, six?”

It only seemed like a few minutes when she reappeared, once again wrapped in a towel, this time with her hair slicked back and wet. The towel stopped half-way down her thighs and I guessed that she was naked underneath it. Or was that just my imagination?

“Can I help?” She offered.

“I’m good, nearly ready. Thanks.” I said, but thought, “Help? In a towel?”

Amy walked over to the sofa and sat down facing me. She ran a hand through her wet hair and picked up a magazine. “Anything good on TV tonight?” She called over.

“I doubt it. It’s Saturday.” I cut the last of the peppers and threw the remains into the sink. I glanced up and say Amy leaning back on the sofa, her legs apart and the towel only covering her crotch with a shadow. I quickly looked away, hoping she hadn’t seen me notice. Then I took another furtive peek, just to see if I really could see her pussy. It looked like I could.

She went up to dress while I cooked the steaks, getting back just in time to pour some wine as I plated the meat and some stir-fry vegetables.

“This looks great.” She exclaimed. “What a guy. He can cook too.”

We mostly spoke about the girls’ plans for their European trip as we ate. I told her of a few things I recommended they see as I’d been on a couple of business trips to London and Zurich. She seemed more interested in night clubs in Spain and beer in Germany. I felt old, and not very happy.

We cleaned up the dinner things together and agreed to watch a movie. Amy sat on a chair and laughed her way through the movie. I sat on the sofa, not laughing as I’d seen the film before, and snoozing through the second half. It was just after nine when I noticed the credits were rolling on the screen. I stood up wearily. “I’d better get some sleep.”

Amy declared she was going to find something to watch for a while, I said goodnight and left her surfing channels.

Dozing through the movie proved not to be a smart thing and when I turned out the light and lay my head on the pillow I was wide awake. I resisted turning on the TV in the bedroom and tossed and turned as the minutes slowly passed. I started to wonder how I was going to pass the following day, at least until my sister arrived, but didn’t get far with that as the distracting thought of Amy sunbathing came to mind, closely followed by the image of her open legs beneath the towel.

As much as I hated myself for it, I started to feel a familiar tingle of excitement as I thought of her and my cock started to react. An image of her towel falling away and leaving her naked before me filled my mind and my hand found its way to my hardening shaft.

At first I was annoyed by the excitement, given my distain for the subject of my thoughts, but the inevitable warm comfort of stroking myself spread over me and I started to think that jacking off might not be such a bad idea. A sleep aid even. I still thought about Amy though.

As I started to stroke with some more intent I pushed away the bed covers and exposed my erection to the cool dark light in the room. I lay back and stroked slowly, enjoying the sensations as they built and thinking about Amy. I imagined I was standing at the patio window, stroking as she ran her hands over her naked body. I thought about kneeling in front of her on the sofa, looking up under her towel and reaching out to…

The door opened.

“Bob? Are you awake?” The backlit outline of Amy appeared in the doorway and I quickly pulled the bedclothes up to my chest. “Are you okay?”

“I’m fine.” I answered. “What is it?”

“I thought I heard something. In here.” She took a few steps towards the bed and I saw that she was wearing the same panties and vest that she had the night before.

“Nothing.” Was all I could manage, wondering how suspicious my quick movement may have appeared. “I was just dozing.”

Amy sat on the end of the bed. “Oh. Okay.” I couldn’t see her face, but her voice seemed a little less sure than it normally was. “Maybe it was the wind. My parents always said it was probably the wind when I heard things in the night.”

“Maybe.” I agreed.

She sat there for a few seconds, not saying anything, just seeming to look at me in the bed. I thought of the weird way the bedclothes lay and wondered what she was thinking. I willed her to just get up and leave me alone.

When she spoke next all her normal tone had returned, and was even playful. “Were you…” She pointed at the bunched comforter. “Were you playing with yourself?”

“No.” I tried to sound indignant and offended, but was dimly aware it came across as defensive.

“You were.” She said immediately, almost gleefully. “You were jacking off.”

I said nothing, wondering where this was going and dreading the fact that Amy would think this was hilarious and was bound to tell my sister, probably even while I was in the room.

“I wasn’t.” Feeling helpless and cornered, my voice was now a cross between lame and pleading. I just wanted this moment to go away.

“Prove it.” Amy indicated the comforter. “Show me you weren’t.”

“No.” I said indignantly.

I didn’t expect her to simply reach across and pull the comforter away, but that’s just what she did, revealing my semi-erect cock. “I knew it.” Amy proclaimed victory.

I pulled the comforter back, covering myself up again. I felt embarrassed and angry, but somehow I mostly felt like a loser. Who knew what Amy would do with this information? But I didn’t know what to say. I wanted to shout at her and get her to leave, but didn’t want to make the situation worse. I felt paralyzed as Amy just sat there and grinned.

“Show me.” Amy tugged at the bedclothes but I held firm. “Show me what you were doing. I want to see.”

“No.” I protested.

Amy ran her hand under the bedclothes and started to feel for my leg. As soon as I diverted my defense she pulled on the comforter again and pulled it clean away. I was slightly more flaccid than then, but exposed to her gaze.

“Nice cock.” She appraised. “Stroke it. Let me see what it’s like when it’s hard.”

“Amy…” I stumbled, “this is crazy, I’m sorry, but I can’t…”

“Don’t be silly.” She shuffled up the bed. “If you won’t do it, I will.” She reached out and took my cock in her hand.

I could only watch as she picked up my limp member and started to shuffle it up and down, attempting to shake some life into it. Regardless of how embarrassed or angry I was, the proof that a man’s cock operates independently of his will came when I felt the familiar pulsing of a building erection. Amy felt it too and giggled.

“This is better.” She continued to work my shaft as it stiffened. “You have a nice cock. Were you thinking about me when you were playing with it? I know you were looking at me this afternoon.”

I said nothing, feeling that denial was useless and coming to terms with the pleasure Amy was starting to create as she worked my cock.

“I’ll bet you were wishing I was licking you, blowing you. Am I right?”

She looked into my eyes this time and I gave in, nodding in a defeat that was already starting to feel like a victory.

“I was thinking about you too.” She admitted. “It’s been ages since I had a good romp. I hoped we’d be able to use some of our time alone together. I won’t wreck your relationship. I promise. No one will know. I just think we need a little fun here. That okay?”

I was about to nod but caught my breath as she dipped her head and took my cock in her mouth.

Her warm, young mouth around me felt instantly divine and I laid my head back and let her suck on me eagerly. She was good. As her lips enveloped as much of my length as she could and started to slip up and down I felt her tongue rub along the underside of my shaft and then over the head as she almost pulled off, doubling the pleasure I felt. I looked up and found her eyes searching for mine, looking for feedback on her progress, wanting to know she was doing a good job. I believe she found it in my eyes.

Clasping her hand over my balls, Amy swiveled around to straddle my torso, still sucking on me but now presenting her ass to my face, and fingers. I looked at the material of her panties as it disappeared into the cleft of her butt, then expanded again as it followed the curves of her pussy and pubic mound. I reached out and ran my finger between her legs, feeling the tightness of her skin and the gorgeous hills and valleys of her form. I pushed a little harder at the valley of her pussy and she gasped, just lifting off me cock momentarily and then resuming her work.

I pushed two fingers inside her panties, down the side of her pussy and zeroing in on her hot hole. She was wet all around, slick folds of sweet juice and teenage flesh. My fingertip traced the line between her pussy lips and slipped inside a little. She was hot inside, hot and tight. I pulled at the sides of her panties and tried to pull them away. Amy stopped working my cock and slid them away for me, resuming her straddling position, then pulling off her vest before grabbing my erection and stuffing it hungrily into her mouth again.

I pulled her back towards me, positioning her over my mouth and letting me savor the sight of her shaved pussy before I started to lick between her lips. Her juice literally dripped down my tongue as I licked her and she squirmed with pleasure above me. I used my hands to pull her as open as I could get her and probed my tongue as deep as I could. I heard her breathy voice encourage me when she slipped off my cock again, pausing because her pleasure was rising faster than she’d expected.

Sensing her rise, I eased a hand around her leg and got my fingers up to her clit while my tongue lapped at her opening and probed her as far as I could. I felt her respond to my finger and rubbed harder. “God that’s good,” she panted, “don’t dare stop.”

I didn’t stop, eagerly lapping at her and rubbing harder as I felt her climax approach. Amy stiffened slightly, still holding my cock as I continued to rub her clit. I felt her hand clamp around my balls as she came, crying out, “Oh shit” at first, then the spasms of her orgasm were palpable on the tip of my tongue as I maintained contact with her pussy.

When the moment passed for her she turned around to face me, her wet pussy covering my cock in her juices, just because it was under her. “My God,” she breathed, “I guess I needed that more than I thought. That was fucking amazing. Quickest I’ve cum in months.”

I reached up to take her breasts in my hands. They were small, but soft enough that I could get a handful and feel her nipples with my palms. “Your cock felt so good in my mouth. You were so hard.” Amy continued her commentary. Her tone was a little unsettling as it was close to a “normal” voice, like she was telling me about something she’d experienced with another lover, but I shook the discomfort that caused and resolved to enjoy the moment. She’d promised not to tell anyone, and I believed her. “You want me to make you cum like that?” She asked.

“No.” I felt stronger now, part of this union now. “Later maybe. I want to feel inside you first.”

“Like this?” Amy shuffled her body back a little and pushed her pelvis up, obviously indicating that I could enter easily with her on top.

I nodded and Amy simply reached down, took my cock in her hand and positioned the tip at the entrance to her pussy. She paused in that position, searching my eyes and catching my gaze before she started to descend on me slowly.

Amy’s smile seemed to widen as she took more of me inside her. I tried to watch her eyes but the instinct to look down and see my shaft disappear onto her was too much and I diverted to see my thick hard on slide easily into her hot, slick, pussy. When she’d swallowed all of me Amy’s face changed to a grin and she asked, “Better?”

I gave a deep sigh and was vaguely aware of smiling back at her. “Incredible.”

“You’re so hard.” She pulled herself up an inch and slid down again. “I so love that feeling of a really hard cock. Your balls feel full too. You got anything in there for me?”

I watched the impish grin on her face and loved the feeling of freedom Amy brought to her lovemaking. She appeared to have no communication barriers and was simply out to share and enjoy the moment. I nodded an answer to her question, knowing that I had plenty of cum to flood her tight little pussy.

Looking down again I watched as Amy rose up my shaft until the head of my cock was almost out of her, then slid down on me again, slowly and deliberately. “You like me on top? You like seeing your hard cock slip into me?” Amy seemed to ask many more questions that I had answers for, but it didn’t seem to worry her. I continued to watch as the pleasure of her riding on me increased. Now I started to push up to meet her down strokes. “Is this too much of a tease for you? Do you want to fuck me harder?”

I managed to grunt, hopefully indicating that I was just fine continuing with her on top. Amy increased her speed a little but seemed to take care to make each stroke over me as long as she could. I looked back at her young face as she reveled in the control and freedom of her position. The first tingling of climax began to spark in my groin.

Amy must have seen it in my face and she immediately felt behind her to cup my balls. Something there confirmed my state to her. “I can feel you’re ready to cum. You want to cum for me now?” She must’ve seen me nod but continued her slow strokes, lifting off then covering me over and over, a relentless slow rhythm that was bringing me to climax. I wanted her to go faster. I wanted to cum more than any other time in my life but Amy continued her solid, slow rhythm. My legs stiffened as the climax started to radiate out, my body desperate for release now, knowing it was coming but having no control over its arrival.

I felt her squeezing my balls hard as I started to cum. I’m sure I grunted and moaned as the explosion of ecstasy went off and allowed sublime pleasure to flood through my body. I grunted again as the orgasm went on and on, longer than I’d ever known. It almost seemed like the climax would never stop, then it crested and I started to shoot cum into Amy.

I felt the warm flood of my seed flush around me as her pussy gripped me and she continued her relentless rhythm. She was smiling, a big, wide grin. All of a sudden it was hard not to like Amy. Maybe I’d misjudged her?

She slumped on top of me when she was sure that I was done. I expected her to wrap her arms and legs around me then but she squirmed off me and onto her hands and knees. “Fuck me. While you’re still hard. I’m close. I want to cum again.” It was almost like a command.

I wasted no time in getting behind her and guiding my sopping cock to her pussy. I slipped in easily and immediately started to thrust into her. I needn’t have worried about losing the erection, I was still hard and she was close to orgasm, which became evident almost as soon as I started to thrust and she quietly urged, “Harder.”

Pumping into her time after time, I heard Amy grunt with each thrust, obviously enjoying what I was delivering for her. I tried to reach down and touch her clit, but she shuffled away and simply said, “No need.” When she pushed back on to me and shouted a loud, “Oh”, I knew she was cumming.

I kept thrusting, feeling the first deflation in my cock but happy knowing that Amy had cum. Eventually she slipped off the end of my cock and fell face-down on the bed. “That’s better.” She giggled. “Good for you?”

I slumped onto my back. “Horrible. Maybe the best orgasm of my life.”

“Better than jacking off?”

“Just a bit.”

“Good.” Amy snuggled over to me, face to face. “How long before you can cum again?”

I looked at her, trying to work out just how serious she was with that question. “I just want to know how long I can nap for. I like a nap after sex, but I don’t want to miss out on fucking you some more.”

I promised to wake her when I was ready.

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