As we reached the front door, as I turned the knob to open it for Amy, as she stepped in ahead of me, I heard "One Hundred Dollars. " Never turning back to me. Amy went up to her room. Amy was long gone before I managed to stagger up to my room. Anyone seeing me lying still on my bed with my eyes closed would have assumed I was at rest. Yet inside my stomach churned, my heart pounded, and brain crackled with activity. When I heard "One Hundred Dollars", for the tiniest fraction of a fraction of a second, my shocked mind tried to form "You rotten whore. . . " but I cut that notion down in mid-thought. Reigning in my runaway head, I forced myself to think. Who is obsessed with whom? I had no concept of how unappealing my requests might be to Amy. Maybe she totally hated those show-and-don't-tell sessions. Maybe she thought I was pathetic, or worse. Everything we'd done had happened after a lot of me hounding her. Maybe, maybe, maybe.
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. . And let's face it, if she'd just said, "You wanna screw me? Sure, no problem. Let's go do it. " Wouldn't I be tempted to call her a slut in anger some day?Eventually, I got past the wondering and doubts that were on the verge of making me a complete lunatic. Forcing myself to comprehend the awesome reality that I was only $100 away from losing my virginity, with the girl I wanted more than any other, allowed my thinking to finally straighten out, plus other things. School was about to let out. I could make a lot more money during the summer, naturally. But to clear a C-note, plus sticking to my savings goal, meant I'd have to bust my hump like never before. I'd sworn years ago to have a stash so I could start a business when I graduated; I HAD to follow my plan. Hey, if I could just make an extra $10 each week, in ten weeks I could be in heaven. With my thinking becoming more logical, I knew having Amy initiate me was worth a king's ransom. Whatever I had to do, I would. Having Amy was worth any sacrifice. Let's face it, could ten times that amount ever buy something that would mean as much to me? No way!So now I had a plan.
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My first decision was to stop pushing the vision of Amy, on my bed, with her legs spread, out of my mind! For now I'd drop my drawers and masturbate like crazy. Later I could list all the ways I could think up to generate extra income. Eleven weeks is what it took me. There was a two-week stretch where it rained damned near every day. Yet the day finally arrived when I came home with the final few dollars. After a shower, dressing, and generally doing everything I could to make myself as presentable as possible, I made my way with the money to Amy’s closed door. You might think I wouldn't be nervous, but I was, tremendously. Even my knock on the door sounded nervous to me. "Come in. " was my cue. Stepping in, I spied Amy on the old easy chair she used for most of her reading. Kneeling beside the chair, I clutched her left hand, opened her fingers until her palm was flat and then carefully laid the $100 into it. Her expression flickered, as it had registered, we hadn't spoken a word about our conversation of almost three months ago. But I knew this was a lot bigger deal than asking to see "boobs", I was paying her to take my cherry. My conscience compelled me to speak.
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"Amy, guess I'm worried that you might have thought I'd never want you enough to actually earn this money. I need you to know that I want you more than anything. But I can't tell you how much I adore you, then push you into something you weren't. . . "When I paused, searching for words, Amy ended my stumbling offer to renege with a simple, soft-spoken "When?""Well. . . there's girl stuff I'm mostly in the dark about. Guess, I'm pretty much ready all the time, so maybe you should just let me know when it's good for you. "A sweet smile spread across her face, her voice was warm. "I'll let you know. It was nice the way you asked. "Leaning in, I did something I hadn't done in ages. I kissed Amy, almost full on the mouth.
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Gently, her lips pursed slightly, returning my kiss. Never imagining this far ahead, having no further idea of what to do or say, I stood, turned, then beat a hasty retreat to my room where I spent all night dreaming of a day to come. Though outside it was a cool, dreary, rainy late August night, I was as bright and cheery as I'd ever felt. Our folks had just left to watch a concert. Following a fund raising dinner, they'd be staying for speeches and schmoozing with local wannabes. Since the drive alone would be nearly an hour each way, they clearly would be out until the early hours. Three days earlier, Amy had casually mentioned that this evening would be a good time to conclude out business. She was as poised as if she'd been suggesting it would be a nice night to help me balance my checkbook. Who knows, maybe it meant little more to her. It sure meant a hell-of-a lot to me. No start time having been mentioned, and me being too nervous to press for particulars, I'd merely showered and spiffed up before the folks departed. Having changed into nice pants and a pressed shirt, I waited expectantly in my room for events to unfold. I'd left my door open, choosing to read a new fiction book even though I'd just accepted the fact that no matter how many times I'd read page 1, tonight I wasn't going to remember what it said. Eventually a lovely Amy wearing a simple, but delightful frock appeared in my doorway. I arose from the bed a bit too fast.
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Desperate to appear grown up, calm, and collected, my voice betrayed my true anxiety when it croaked, "Come in, please. "Probably a girl could have told you every detail about the pattern and shade of her dress, I only recall it showed her marvelous figure, was a light color, and had some kind of flower pattern. My hyperactive male brain was too busy trying to see the female form within the dress for much else to register. Still, it was her face and eyes that consistently held my gaze. Before I had time to wonder what to do, she turned halfway around saying, "unzip me. "Hoping she couldn't feel my hands shake, I did my best to gracefully pull the tiny metal tab all the way down. Turning to face me, Amy offered, "I think it would be nice if we helped each other undress. " When she leaned a bit forward while lifting her arms towards me, at last I got the hint. Grabbing the material at each shoulder, I slid the dress down her arms until it cleared them, then I helped her step out of it. Amy took the dress from me, walked to my chair, folded the dress and then carefully draped it. As she did, my knees grew weak from the impact of her gracefully moving about in a matching lacy bra and panties. Returning to me, I muttered, "Wow" as Amy unbuttoned my shirt; she smiled and then slid it off me. My undershirt followed. "Well, you're bare above the waist, so I guess you get a turn. " Amy turned away, inviting me to unclasp her bra.
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Using two hands and looking right at it, it still took me two tries; now I was pretty concerned about someday having to try it with one hand, behind a back, under sweater, in the dark. From behind, I ran my palms from her lower back up to her shoulders where I tipped the straps forward, then down her arms. Amy slowly faced me; her breasts were even more beautiful than when I saw them months earlier. After a short delay, which allowed me to drink in her beautiful bosom, Amy walked the several steps required for her bra to join her dress. The tick tock sway of her tight buns, then the jiggle of her gravity defying breasts as she returned, left me excited as hell, and wondering if that short trip was calculated to have precisely just that effect on me. Reaching my side, Amy led me by the hand to my bed. Lightly touching my shoulders, she turned me and then guided me down until I sat on my bed. Kneeling, Amy removed my shoes and socks. That done, my belt was soon loose, my pants unhooked, my zipper lowered, and my slacks sliding off. Amy took my shoes and clothes over to join her things and then kicked off her loafers, leaving them next to my shoes.
By the time she turned around, I was already on my knees waiting for her. The moment she reached me, I took Amy's panties off. With the raised mound of her pussy practically in my face, my brain sent out a hundred different 'do this', no 'do that' type messages. There being so many things I wanted to try, I found myself frozen, unable to do anything. "Stand up, I have a turn left.
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" Thus prodded into action, I stood. My gaze shifted to her breasts. Sliding her fingers down the back of my arms, Amy ended up finding both of my hands. As she lifted my palms to her lips, she kissed each one before holding it against her cheek. "In all this time, we've never touched each other little brother. I think this is the time to start. " Amy still had each of her hands covering the back of mine. With a torturous lack of speed, she pressed my hands tightly against her warm skin as she guided them down until I felt a firm nipple pressing into each palm. Before releasing me, her fingers taught mine a basic fondling move. "If I'm going to be able to take your briefs off, I'm going to have to touch you now, judging by the bulge I see. "Despite my aroused state, Amy made me chuckle a bit as I realized what she meant. I never stopped playing with Amy's soft, spongy breasts, but I did hiss extra air into my lungs when I felt her fingers slide under my waistband, then onto the top of my buns. Moving her hands to my hips, indeed she wasn't able to lower my underwear very far because the elastic in front immediately snagged on my steely erection. Her right hand slid to down my outer leg, then across the front of it until she found my balls. Amy cupped and rolled them several times.
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Once I winced when she used too much pressure, instantly Amy played more gently. Soon her palm slid up my shaft, cupping around it, stroking me several times. With her wrist now preventing the earlier hang up, she worked my shorts down until they fell around my ankles. Her palm wrapped around my shaft once again. This time she fondled the swelling red glans in addition to stroking me. Naturally, my breathing had changed to deep inhalations. I'd been groaning steadily since her hand first touched my genitals. Into my ear she whispered, "Maybe we should get on the bed now. " Releasing my throbbing penis, Amy stepped past me, climbed onto my mattress, then stretched out on her back. My excitement was so high, that I was past thinking clearly. Immediately, I tried to climb on top of her, my hips tried to poke my erection into her groin. Using an almost maternal voice, Amy guided my actions, "It's too soon, I'm not ready for you yet. Lie beside me. I need you to touch me. .
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. between my legs. . . until I'm all slippery inside. "Rolling off her body, losing the intense warmth of so much naked flesh against mine helped me calm down a tiny bit. After giving me a minute to relax, Amy whispered. "Feel me up now; it's time to play with. . . my pussy. " Lifting my head as my right hand slid across her taut tummy, I saw Amy spread her legs farther apart. My dick jumped. My fingertips ventured into pubic hair for the first time. My dick jumped.
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My fingertips felt found the top of her slit, felt the increased warmth and moistness. My dick jumped. My middle fingers burrowed into her slick gash. My dick jumped. The scent of her increasing arousal reached my nostrils. My dick jumped. Everything was new; everywhere I touched was more exciting then where I'd just been. After leaving me to my own devices for a time, Amy reached for my hand, then showed me a way to massage her. She'd teach me a way she enjoyed being fondled, then release my hand. A minute later, she'd show me another way she liked to be stimulated, then release my hand again. Just when I was nearly out of mind with desire, I heard the magic words I waited 18 years to hear, "Do you want try now. "Being at an 'animal lust' level, I was climbing back on top of her divine body before she'd said ". . . now.
"The serious tone in her voice cut through my lust induced fog. I did hear Amy say, "You must not come inside me, I could get pregnant. "Grunting an "I'll be careful, promise. " I lay atop my sister's sensuous, sexy body. Holding her arms, raising my head, eyes closed, my hips repeatedly pushed my penis into her bush, but unsuccessfully. "Let me help you. Lift up; pretend you're doing a push up. "Taking Amy's suggestion, I rose up until my elbows locked. When I reached full stretch, her right hand was reaching between us; my eyes tracked it all the way. I got to see her grip my shaft, then aim me at her opening. When she gently tugged me towards her, my hips followed her lead, pushing gently towards her body. "OH GOD!" escaped me when my tender tip touched her fiery pink entrance. As passion engulfed me, I found myself unable to think. At best I was able to follow Amy's directions. Following several failed attempts to sink my erection into her, Amy held me stationary after pushing me back.
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With her free hand, she scooped out some of her fragrant lubricant, added it to mine, then smeared both around my shaft until it was rather slippery. Gripping me again, Amy guided me back into a short stroking rhythm, this time she lifted her hips slightly. An intensely pleasurable feeling immediately flooded my system as we not only connected, but I saw my penis begin to gradually sink deeper and deeper between her hair-lined vaginal lips. Nearly a third of my length was pushing into her, when I shouted, "Pull me out! I'm going to come. "Like a flash, we pulled apart. Amy pointed me towards her tummy; her free hand grabbed my butt, then pulled us together. She tipped her hips, rubbing her vulva along my shaft at the same time my hips cut loose, thrusting like mad as sperm flooded out of my body onto hers. My chin fell limp over her right shoulder. Her left arm went around my back, holding me close as my body acted out a virgin's first coitus related orgasm. The innumerable sensations from writhing atop my first female, from achieving a partial penetration, caused my body to jerk, thrust, and spasm for several minutes before exhaustion at last allowed me to lie still. Amy coaxed my sluggish body to roll off of her. While I lay panting, she slipped out of the room. It wasn't until I felt a warm washcloth cleaning me from head to toe that I realized she'd even moved. This time I was at least aware when she left the room. Too tired to lift my head, I at least heard her walk to the bathroom, rinse and wring out the washcloth, then snuggle up beside me again moments later.
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The warm rinsing helped revive me. Neither of us spoke for a time, but Amy trailed her fingertips up and down my arms, chest, neck and face for several minutes. Opening my eyes, I smiled up at her pretty face. "Are you back among the living?" she asked. I nodded an affirmative, though perhaps a tad more lazily than I'd intended. "Well, Little Brother, I promised to teach you about sex, but we didn't get far enough to finish the lesson. We have time, care to try again?""Amy, you're absolutely wonderful. I hope you know that. May I kiss you?"Amy launched into a hearty laugh. For a moment I felt hurt and rejected, then she managed to say between giggles, "Well, since I just allowed you to nearly screw me, I guess a kiss would be OK. You are a dear, you know. " That said, she lowered her lips to mine for a soft, lengthy kiss. "What do you call it when your sperm shoots all over the place?""Coming like a son-of-a-bitch!" I laughed. "Well, darling brother, I'd like to come now. If I come, I think you'll be able to get your nice penis inside me a lot easier.
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Just remember when you do. YOU MUST NOT COME INSIDE ME!""Understood, now teach me how to help you come. ""Let's start by seeing how good a kisser you are. Once we get comfortable with kissing, I'll steer your hands or mouth where I want you. Sound OK?"I let my lips silently speak for me. Pulling Amy close, I began kissing her. I had French kissed with a few girls, but never to a point where we got crazy from it. Weird as it might sound; it was more awkward for me to make out with Amy than it had been to try pushing my penis into her. Guess it was more natural for me to think about having sex with Amy, than it was to make love to her. Yet the longer I held her warmth close to my naked flesh, the longer I kissed the sweet girl in my arms, the easier it became to make love to the woman my sister had become. Her tongue wasn't as shy as mine, Amy soon improved my technique to such an extent that she was groaning into my mouth. Her body had been rubbing against me for several minutes when she guided my lips down her neck, then to hers nipples. I'd only been kissing her engorged nipple; she whispered that it was time to suck it into my mouth. In my head I heard, "Ohhhh yeah! That's what they're there for. " I went back and forth until Amy was outright panting.
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During this time, Amy had guided my middle finger into her vagina, showing me the in and out motion she wanted from me. Novice or not, I knew she was about ready to explode. Amy pulled my finger out of her, then dragged it up her slit. Carefully she steered my fingertip until I felt a teeny pearl-like button. "That's my clit. " She hissed. "It's super sensitive. Rub it. Yeah. Yeah. YEAH! Quick, get between my legs. "As I clambered between her inviting thighs, her left hand rubbed her clit like crazy; she was definitely having an orgasm. I was quick getting on top of her. As I'd done earlier, I held myself up with my arms. Amy was still coming, but her right hand found my renewed erection.
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Immediately she had me in the vicinity of her opening. Frantically Amy rubbed my crown around her slit, then whipped me to her entrance. Her left hand flew from her clit to my butt; she pulled me hard, simultaneously lifting her hips. I sunk nearly halfway into her. Releasing my shaft, her right hand grabbed my other butt cheek. She pulled us apart until only my tip remained inside Amy. "Now, push hard!" she barked. Already feeling like a coiled spring, when I felt her fingers dig into my buns, pulling me down for all she was worth, I drove my entire erection into her pussy. Hearing a gasp that sounded as if it were tinged with pain, I froze, still buried inside her velvety depths. I tried to wonder about any pain she might be feeling, but the extreme pleasure of feeling her muscles gripping my shaft, combined with the most perfect moist heat I'd ever known, made it so difficult to think straight. Just as I was about to ask Amy if she was OK, her mouth found mine. When her tongue slithered into MY mouth for the first time, I was so turned on that I almost forgot I was embedded in her glorious body. I was kissing her with a passion I'd never suspected was in me within two seconds flat. It was actually her hands on my hips, prompting them to rise, then to fall, that got me to begin screwing her while we kissed. Allowing her hands to control my tempo, we began slowly, but gradually sped up.
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When my thrusts became so fast that I couldn't kiss Amy very well, I dropped my head so we were cheek to cheek. When I felt my climax approach, I began to lift up on my arms so I could withdraw quickly when I had to. I warned Amy, "I'm getting close. "Being up on my arms also allowed me to drive my penis harder into her. Our hips were making loud slapping sounds. Funny, short, breathy sounds came out of me. "Almost, almost. I wheezed. "Amy had lifted her head, watching my shaft sliding in and out of her body. She had a hand between us. When I abruptly pulled out of her, her hand flew to my shaft, gripping me, thankfully giving me a sleeve to piston my shaft through. Like a madman, I pumped her fist. Looking between us, I saw strands of white sperm shooting all over her white skin. I groaned steadily from that moment until I finally fell on her like a limp rag. By pressing her legs together, Amy was able to keep my hips raised far enough that she was able to lovingly milk my cock while we shared post-coital kisses.
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When her legs got tired, I rolled off of her. It was only then as I surveyed the aftermath of our love making that I realized I'd been oblivious to something. My wilted penis, and her palm when I looked closely, showed little streaks of red. I had been so focused on losing my virginity that it never occurred to me that I was asking Amy for hers. Just because she was a little older, and so desirable, I'd assumed she was more experienced. I felt dumb as a fence post. Unable to think of anything worth saying, I held her close and kissed her with all the love and adoration I was feeling. As my passion ebbed, I was in danger of falling asleep. Seeing that, Amy got up, then pulled me to my feet. Holding hands, she led me to the bathroom where we washed each other off. With arms around each other, we went back to my room. Gathering up her clothes, Amy suggested I get into my pajamas, then crawl into bed before I fell asleep. I knew it was good advice. But before I let her leave, I hugged Amy through her armful of clothing, taking the opportunity to feel up her sexy butt for the first time. Giving me an affectionate good night kiss, Amy turned to leave.
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Pausing in the doorway, she turned back to me. Looking slightly concerned, she asked, "Is there anything you feel sorry about tonight?"This time I didn't have to think, "Only that I couldn't come inside you. Making love to you was a hundred times better than I dreamed it could be. I just wish I could make love to you and not have to pull out. I wish I could keep my penis inside your amazing pussy the entire time my sperm was pumping. I'd give a lot to know how it feels to coat your insides with my hot semen. "Meeting my gaze, yet not missing a beat, Amy simply responded "One hundred fifty dollars. " Before my chin finished falling, she'd turned, heading for her bedroom. By the time I reached my door to close it, Amy was already in her bedroom with her door closed. Crawling into bed, I felt way too good to be depressed. It had taken me all summer to earn $100, would I still be young enough to have sex by the time I earned $150? Somehow I'd managed, I was feeling highly motivated, also highly pleased with myself, now being a former virgin. So I was soon asleep, with a smile on my face. Next morning, I did something I hadn't done in years. I sat on the same side of the table as Amy. I hadn't thought about it until then, but we'd been sitting on opposite sides of the dinner table for years.
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Whispering, she teased, "Before you get any pain-in-the-ass ideas, I'm telling you now. . . you couldn't afford it. "We could go to a movie together next weekend? My treat, I think I can afford that. ""Yeah, I think I'd enjoy spending the evening with you. "During the coming week, I had had a ton of odd jobs lined up. I made better than average money. Being so busy, the days went quickly, and I slept soundly each night. Saturday afternoon I arrived home around 4PM. The day before I'd hit the bank to deposit most of the money I earned that week into my savings account. Before I undressed for my shower, I put $11 into a now empty cigar box for my 'Special' fund. Leaving $8 in my wallet for that night. By 5PM I was showered, groomed, dressed, and seated at the dinner table. By 5:30, Amy and I were on our way.
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"Before we get too far from the house, are you sure you brought your money? It'd be a long trek home, and I want to make the 6 o'clock show so we're out early in case we think of something fun to do later. "Taping my pocket, I felt my wallet. So I assured Amy that I was good to go. "Are you absolutely sure? Because if you're wrong, you know you'll never hear the end of it!" she teased me. To put an end to Amy's whining, I decided to wave my $8 bucks under her nose. Whipping open my wallet, I froze. My $8 was there, all safe and sound. But I also found six twenties, and a Hundred Dollar bill, exactly the amount I had already paid Amy for our previous ‘Lessons’. We never made it to the movies that night. Amy earned herself the $150 back off me before we got home. Amy comes to stay one or two weekends every month, she's due any minute now. I keep a guestroom just for her. When she arrives, on her pillow she'll find the same six twenties, and a Hundred Dollar bill!.
