I brought it up, and it wouldn't be fair if I left it hanging. Here goes:
Many years ago, the summer before I went to college, I was seeing a girl who was older than I was. I was 17, and she was 24. 7 years may not seem like a big difference, but I always felt a little insecure about us. I was content with kissing and holding hands, and I didn’t push for more, especially since she told me she felt like I was with her for her, not her body. One of my biggest insecurities was my significant lack of sexual experience, which is probably why I didn’t try to talk her into having sex. I was, in fact, a virgin. I’d never done anything because of my shyness, brought on by being two years younger than everyone else in my classes at school.
My oldest sister and her family were staying with us, because her husband had gotten injured pretty badly at work, and had to spend a couple of months in the hospital because of it. She’s a little more than 16 years older than me. We had been very close growing up, as she had been the one to take care of the rest of us when mom or dad weren’t at home. We had always been able to talk to each other about anything and everything. The upcoming July 4th weekend, my girl and I were going to go to a holiday cookout/fireworks thing with a bunch of her friends. I knew I’d be the youngest one there, and didn’t know anyone else, so there was a lot of self-imposed pressure to be mature enough to fit in, and most importantly, to be fun to be around.
I talked to my sister about it a lot in the weeks before, explaining my shyness, my insecurity, and my lack of social experience, and how was I going to deal with the event. My sister knew there was more to things than I was telling her, and asked me if I was leaving anything out. I told her that I didn’t feel like talking about that with her, since she was my sister, and I thought that covered it. She asked me outright if the problem was that I was worried about maybe having sex with my girl. Somewhat flabbergasted, I told her it was, and that I had no clue how to go about the process, but ‘you’re my sister, I don’t know how to talk about this kind of thing.’ Well, we didn’t really come to any kind of satisfactory results. She promised me we’d talk more on it, after she’d had time to think about it.
The next morning I was outside early cutting the grass, while the rest of the family was out at work or off at friends’ houses, or whatever. Sis was around doing stuff, so we were totally alone all day. Around 10 that morning, I finished cutting the lawn, and came in for a shower. As I was coming out, she was waiting on me to get out of the bath. She was going to take a shower too, as she had to go out and do some shopping later in the afternoon, and wanted to get cleaned up before everyone else got home. I went on into my room, closed the door, and put on some clothes. A bit later, I thought heard her come out of the shower and close the door to her room as well. I decided to head downstairs for a snack, and as I stepped out into the hall, there she was, standing there in a bathrobe with a towel wrapped around her head. I apologized for holding her up, and started to go back into my room, when she asked if I wanted to talk more about the upcoming weekend. Again, I didn’t think anything of it, and told her to come on in when she got dressed. Well, she didn’t go into her room to dress. She just followed me into my room and sat on the desk chair. I flopped down on the bed, and asked her what was up.
Now, let me describe my sister. As I said, she’s 16 years older than I, so at the time she was about 34. In high school and college, she’d been a cheerleader and a couple of beauty pageants, so I’d say she’s an attractive woman. One doesn’t normally think about one’s sister as being hot, but she is one of the most beautiful women I have ever seen. She’s about 5’ 4”, with the most perfect figure I’d ever seen on any woman, before or since. The best way to describe her would be to say that she had the perfect body of a 1950s Gil Elvgren or Al Moore pinup. Slender, but rounded in all the right places. She has long auburn hair, bright green eyes, and a dusting of freckles on her very fair skin. She also has a stunning pair of magnificent breasts. If I had to guess, I’d say they were a full, round, 36D. Even after two kids, they were still firm and high. She still had a fairly flat tummy, and has just enough hip to have a clear difference in size from her waist. I’d seen her in a bathing suit before, and knew that she had a perfect, round, heart-shaped ass. If you want to see what her body was like, go
HERE or
HERE.
She told me she’d been thinking about my dilemma with the party and still didn’t know what to tell me about how to deal with it. I still had no clue in my innocence, and so I asked, if she didn’t have an idea what to tell me, then what did she want to talk about? She said she hoped that I’d be okay with how she decided to handle it. Puzzled, I told her that I was sure I could handle it, and what was she talking about? She took a deep breath, stood up, and announced that she had decided she was just going to show me what to do. So saying, she took the towel from her hair, and dropped the robe off. I was absolutely dumbstruck. It was the first time I had ever seen a totally nude woman in person. She had a little landing strip, but the rest of her from her eyes down was perfectly smooth and completely hairless. She had smooth, fair skin, and those perfect globe-shaped breasts. I still get aroused thinking about that moment, and I can still picture her standing there.
She said this was what she meant about showing me, stepped forward, took me by the hand, looked me in the eye, and told me that what was about to happen could never be mentioned again, I could never tell anyone, and that she had never thought about doing anything like this until a few minutes ago. She had just decided that the best way to advise me was to actually teach me how to make love to a woman. If I had a problem with that in any way, now was the time to say so, and that would be the end of it. The good brother/nice guy in me started to assert himself like an idiot, and I almost told her that there was no way I was going to let her, but then my hormones took over. ‘What do I do?’ I stammered. ‘Let’s get these clothes off of you, and I’ll show you.’ She replied. I stripped, with a little help, and stood there in front of her with a 17-year old tent-pole. She smiled, and told me that I looked like I was already ready to go.
She took me by the hand and pulled me onto the bed. She smiled, and lay down on her back next to me. ‘Run your hands over my body’, she said. ‘See what a woman feels like. Take your time and do it gently, just using your fingertips and palms. Don’t grab at me, just caress.’ Man, was I nervous. Nervous, scared, and a dozen other contradictory emotions all at once. I was so stupid in my inexperience. I followed her instructions exactly, paying special attention to those magnificent breasts. ‘Kiss them,’ she said softly, ‘play with my nipples.’ And she pulled my head down to them. Nibble a bit,’ she told me, ‘don’t bite, but be playful. They’re sensitive,’ she said, ‘this will get almost every woman aroused. Spend a lot of time exploring, to see what she likes and to get her aroused. The more time you spend on trying to get her aroused, the better the lovemaking will be. You have to pay attention to how she responds to what you do,” she told me.
I began licking and kissing. I don’t know how much time I spent on her breasts, but it seemed like forever. I didn’t notice at first that she was breathing a bit faster, but she let out a little gasp, and I thought for a second that I must be doing something right. Then she suddenly pushed gently on the top of my head, guiding me toward her tummy, and I began to kiss and lick everything in reach, until I got to her navel, where I stopped and looked up at her. She told me it was okay, I was doing just fine, and we were about to take the next step. ‘From this point on, there will be no going back.’ she said. I sat up, looking hard into her eyes. She took my hand, and moved it down to that mysterious place between her legs. ‘Just let it rest there a minute’, she told me. I could feel the warmth of her, and then she told me to move my hand around, to gently massage her.
She opened her legs, giving me better access, both to explore and to watch, and instructed me what to do, what parts of her I should be doing things to, and then to gently slide a finger into her, not much at first, firm and easy. ‘Slowly, gently’, she coached. ‘I’m pretty wet already, because I’m aroused, but sometimes a woman isn’t warmed up yet. So you can’t just stuff anything in there without getting it ready. You’re not poking a hole into something. There’s a hole already there” she giggled. After closely examining my very first vagina, she asked if I knew anything about oral sex, and if I did, was I okay with going down on her? I told her honestly, I didn’t really know much. ‘Well, I’m going to have to teach you then.’ She told me to move down some, and kneel between her legs. ‘You should begin by kissing around my navel,’ she told me. ‘Slowly move in circles on my stomach, getting lower and lower each pass. You’ll be getting closer to down there, and when you’ve gotten to it and are ready, use your tongue on me. Explore all around everywhere. I’ll tell you when you’re doing the right thing.’
I noticed a tiny drop of wetness run down the inside of her leg. It was completely fascinating to me, and when I leaned in a little closer, she took my head in her hands and guided my face right in. My heart was pounding in my chest. I started flicking my tongue against her labia (and quite accidentally, her clitoris, not knowing that’s what it was) and apparently she loved the motion, because she told me to keep doing it just like that. ‘Tell your girl to tell you exactly what you’re doing that feels good, and then do those things. Don’t do the same thing over and over for a long time.’ So I got my first lesson on how to go down on a woman. She must have been a good teacher, because she soon told me she was close to having an orgasm, and to do that flick thing with my tongue, it would send her over the edge. So I started doing it, gently at first, and then faster and harder, and she came, tensing up, clamping her thighs around my head, moaning, and grabbing my hair. I could feel her whole body shaking.
‘Wow,’ I thought. I started feeling a little full of myself at what I’d done to her, and asked her what was next. She lay back again, and pulled me up to her chest. She reached over, drew me to her, and kissed me full on the mouth, swirling her tongue, sparring with mine. We kissed like that for a long time, until she pushed me over onto my back. ‘I’m ready for the next part of the lesson, how about you?’ she said, with that playful tone in her voice. She got up on her knees, leaned over me, looked me in the eye and whispered, ‘you’re about to lose your cherry.’ She lifted her leg over, and straddled me. She had both hands on my throbbing erection, and told me this was the moment of truth. ‘Are you ready, little brother?’ She asked, and I nodded, keeping my eyes locked on hers. She lifted up a little, rubbed the head a little into her opening, and then in one smooth motion, slid down all the way onto me, enveloping my hardness with her wet warmth. She let out a sigh, and softly said, almost to herself, that I was really hard, and that I felt bigger than she expected. She told me that it felt good as I entered her. She smiled, leaned over to kiss me, and softly said, ‘Congratulations, little brother. You’re no longer a virgin!’
She sat still for a moment or two, resting her hands on my chest, and looking down at me. I smiled up at her, and she started slowly and moving up and down on me, grinding her hips as she moved. ‘Tell me when you’re feeling like you’re going to come again, so I can slow down. I want this to last a while’, she said. ‘Okay’, I gasped, feeling the warm, slippery wetness of her enveloping me. I began to feel a strange sensation. Not at all an unpleasant one, but something I never expected and didn’t know what it was at the time, not having any experience, but she was clenching and relaxing her muscles around me as she moved, and I could feel her squeezing and releasing around me. She’d pull up almost to the tip, and then slowly slide back down. She kept this up for a while, changing her tempo, the depth, and then suddenly announced that we were changing positions. She rolled off of me, and then leaned over onto her hands and knees, her breasts hanging deliciously below her. ‘Get behind me’, she said. ‘Put the head of your cock against my pussy. I’ll slide back onto you, so don’t you push yet.’ I quickly complied, staring at that beautiful ass in front of me, and I reached down to gently caress her. I ran my hands over her smooth cheeks, and said, ‘I don’t know how to tell you this, but you’ve got an incredible ass.’ She laughed, and said ‘That’s sweet of you to say, little brother.’ She reached back and guided me, and then wiggled away a little bit. ‘Rub the head of it around before you put it in. Some girls like that’, so I did as she told me, and then she slid very slowly back onto me. It seemed like forever before I was all the way in.
I watched in rapt fascination, I could see her wetness glisten, and I could feel every single bit of her as suddenly, I was all the way in. ‘Grab my hips’ she said, ‘I want you to pull me onto you, and then slide back out slowly.’ I simply could not believe that I had actually gotten my dick into a woman, and that the woman was my sister! As I began to slowly move in and back, I leaned over her to grab one of her breasts, and pinched a nipple as I pushed in and out. She let out a squeal, and began to push back harder against me. I straightened back up, and as I did, I could feel her reach down between her legs and begin to play with herself. I almost stopped, wanting to watch, but she started with that clenching thing again. I hesitated once more, and she said, matter-of-factly, ‘Give it to me little brother! Fuck me! Fuck me hard!’ It was the very first time I had ever heard her use that word, and it surprised me. I just watched myself slide in and out of her as we kept rocking back and forth against each other. She started wiggling her hips, and we picked up the pace, finding each other’s rhythm. She was still doing that clenching thing, and I was pounding away, ramming my full length into her with such force that her ass rippled and jiggled and her breasts swung violently beneath us.
She pressed her chest and shoulders down to the bed, spreading her arms wide, and began to groan loudly, interspersed with squeals and a long, low crooning sound. ‘Oh my God, oh my God,’ she kept repeating. Then, she jerked, her body taught, and let out a sharp yelp! I stopped, and said, ‘Too hard? Am I hurting you?’ She snapped right back, ‘Hell no and don’t you dare stop Goddammit, keep going! Fuck me hard!’ and she pushed back on me. She let out another squeal, a deep moan, and I could feel her clench around me much harder than she had before. ‘I’m coming, oh God, I’m coming again!’ she hissed through clenched teeth. I could feel her almost vibrating, as her whole body shuddered. It was the very first time I experienced a woman’s climax from the inside. My dick felt like it was being squeezed. I began to feel my own orgasm building, and I slowed down. She was panting hard and mewling again. I told her, ‘I think I’m about to come.’ I said I could feel it building and wanted to slow down, so we just stayed still like that for a moment or two. After a bit, she pulled away from me. ‘We don’t want that just yet’ she said as I slipped out of her. ‘You should never want to come right away’ she told me. ‘Always make sure you help your partner come a couple of times before you do.’
She flipped over on her back, and looked up at me. ‘Let’s rest for a bit,’ she breathed. We both were breathing a little hard from the exertion, and as I knelt over her, she said, ‘You have a beautiful cock.’ It’s just the right thickness for your length, and it feels so hard and big inside me. She pulled me down on top of her and I rested on my elbows, her hands on my sides, our chests pressed against each other, and those beautiful big tits mashed between us. I said, ‘I’m not complaining, but what on earth possessed you to do this?” She laughed and said, ‘Well, I have to be honest, little brother. I’m really not just doing it for you. You’re my brother, and I don’t like seeing you feeling the way you were, so I wanted to figure out a way to help. I’m a little horny too, since I’m not getting any right now ‘cause he’s still in the hospital. I was in the shower, sort of playing with myself, and I thought, what the hell, I’ll help both of us! So I wanted this too. I know it’s wrong, and I know it’s not like me, and I really hope you don’t think I’m sick or perverted or anything, but I love you, little brother. And two people who love each other can do this together, so don’t feel guilty about it, promise? Just remember, it’s only this one time, and you can’t ever tell anyone.’
After a few minutes we’d regained our breath, and she asked me how much experience I really had. I told her I’d never seen a woman play with herself, and would she, so I could watch her? She grinned, giggled, and said in a low, sultry voice, ‘So you want me to rub one out for you?’ I rolled off of her, and she slowly moved one of her hands down, and began to touch herself. ‘Damn I’m wet!’ she laughed. I was focused on the chocolate-brown nail polish on her fingers, and I saw her start to move her hips in time with her motions. I watched, mesmerized, as she inserted a finger deeply into herself, and then she pulled it slowly out, licked it clean, and continued. She began to move faster, and suddenly she was moaning and writhing beneath me. ‘I’m coming’ she panted. ‘I’m coming again!’ I couldn’t stop myself, and I just scooted down and started licking while she was doing herself. She let out a little squeal, and said, ‘Hey! I thought you wanted to watch me!’ I laughed and said, ‘well, I thought I’d get in some more practice.’ It wasn’t very long before she was coming yet again. Her body shuddered, tensed up, and she orgasmed, with one of her fingers and two of mine inside her while my tongue was doing laps around her clitoris. She lay there for a moment, panting. I just stared at her, watching her chest rise and fall.
‘Come up here, little brother,’ she said. I shifted back on top of her, and she reached down between us, took me in her hand, and guided me inside her once again. As I slid back into her, she shuddered, let out a little moan, and wrapped her arms around me. I could feel her hands on my back, rubbing up and down, and then she grasped my buttocks. I drew back out almost all the way, hesitated a second, and then I rammed it in all at once, making her let out an almost-scream, dig her nails into my back, and squeal again. I stayed still for a moment, looking her in the eyes, and then she grinned up at me. ‘That was a surprise!’ she said, ‘now just move in and out, slowly. Remember, you’re getting your pleasure out of this, but you should be working at mine too. If you’re only there to get yourself off, she won’t enjoy it. We’re going to make love now, so just go slow and steady. Try to make yourself last as long as you can. If you feel like your climax is building up, slow down or stop and just stay still inside me.’ She reached down and squeezed my butt again with both her hands, pulling me into her, something I’ve loved ever since, as it reminds me of that first time.
I remembered she’d said to go slow, so I kept my rhythm to a point where it was almost a lazy in and out motion. I could tell the change in her breathing as her pleasure mounted, as it came in gasps, almost punctuating the way we moved together. She was doing that clenching thing again, and it felt amazing. We kept at it for a long time, and then I could feel my release coming, so I leaned down, bit her earlobe, and whispered in her ear that I was going to come soon. That brought on more energetic bucking underneath me, and a long moan in my ear. ‘Come inside me’, she panted. ‘I want you to come inside me! Fuck me little brother! Fuck me hard and fill me up! Come hard, baby!’ I could feel her nails digging into my back as she pulled me into her harder and harder with each thrust. ‘I’m coming,’ I groaned. ‘Me too,” she grunted, nearly breathless. In the next instant, I exploded deep inside her. She was shaking violently, shuddering, as she wrapped her legs around me like a vise, and hugged me so hard it took my breath away.
I collapsed on top of her, and she stroked my hair. I looked down at her, and she smiled. ‘You’re not going to have any problems satisfying your girl,’ she said. ‘You’re really very good at this for it to be your first time.’ She said as her fingers drew patterns on my back. We rolled to our sides, looking at each other as we lay there for a while, just holding one another. I was actually starting to think about asking her if we could go again, when she wiggled out from beside me and stood up. As she was putting on the robe, she leaned over and kissed me again, and said, ‘I really wish we had enough time to do it again.’ She leaned over, and kissed me deeply, for a long time. Then she abruptly stood up and pointed her finger in my face and said mock-sternly, ‘Just you remember young man, nobody can ever know about this. We can’t ever talk about it, and we won’t ever be able to do it again. I almost wish we could, and I’ll be honest, little brother, you’re a natural. You’re eager to please, and that’s what makes a good lover. You’re going to rock her world, and I know she’s going to enjoy you.’ She draped her towel around her neck, drew her fingertips gently down my chest and stomach, leaned over and kissed the head of my cock, and said she was going to take another shower as she walked out the door.
So, that’s the story. 
Originally Posted by lancer525
I brought it up, and it wouldn't be fair if I left it hanging. Here goes:
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