Little Sister's Dilemma

My Little Sister’s Dilemma

I always considered myself to be a typical teenager, but looking back, I may have qualified as a bit of a “nerd”, for lack of a better term. I never really had a problem with academics, and as a result, never had to study all that hard, or that much. At the ripe old age of seventeen, and in my last year of high school, I should have had the world by the balls. For the most part, I did, too, except for one small, insignificant detail. I had a sister that was a year younger than I was. Now, that might not seem like a big problem, and for the most part, it wasn’t. Except that this particular sister was an absolute knock-out, in my mind.

I was born on the first of November. My Dad always said that he and Mom had been out trick-or-treating, and I was the treat. My Mom, on the other hand, figured that I was a dirty, rotten trick that someone had played. To this day, she still believes that. Anyway, my sister, Joanne, was born the following September, and she was always Mom’s “little baby”. The title used to drive Jo absolutely crazy, but I’d use it if I needed to get her attention. She’d usually retaliate with something like an object that was both close at hand, and suitable for use as a lethal projectile. As you can tell, we had the usual sibling rivalry happening between us.

But it wasn’t all cats-and-dogs fights. Despite the fact that we had our battles, we had our good times, too. If I was feeling down and out, Jo was always there, trying to cheer me up. Whenever it was her that was on the outs, I felt compelled to try and be there for her. At the time, I had no idea of why, but I always seemed to be concerned for her happiness and welfare. So when Jo knocked on my bedroom door one evening, entering before I could say a word, I could tell by the scared look on her face that something in her little world wasn’t quite right. At the time, I was a little upset at the way she just barged in, but looking back, I would have granted her access without hesitation, and my permission wasn’t really necessary.

“Jim, can I talk to you?” she almost whispered. That look on her face made it almost impossible to refuse her request. Even at sixteen, she knew how to push my buttons, and that sad expression, those red-rimmed eyes from crying, all found just the right heart-strings to pluck.

“Sure, Sis,” I conceded, “any time, you know that. You look like you just lost your best friend. What’s up?”

Joanne just stood there, staring at the floor, seemingly trying to find just the right words, and having no success whatsoever. I got up and walked over to her, wrapping my arms around her and pulling her to me tightly, then kissed her forehead. She might only be my sister, but she was a very special person in my life, and the sight of her hurting ripped a huge chunk out of my heart. Finally, she found the courage to look into my eyes, and I could see that she was deathly afraid of something.

“Okay, I give up” I eased into her space. “Something’s got my little sister all twisted and out of shape. Are you gonna tell me about it, or do I have to play twenty questions?” I had another line that I usually used, but this wasn’t the time for it. In the time it took Joanne to finally get the words out, I could have created another half-dozen opening lines, all of them new and untested.

“Jim, am I a . . . lesbian?” she squeaked. You could have heard a pin drop, even on the other side of town. How the hell was I supposed to answer that one? Hell, how was I supposed to even understand her question?

“Okay, Jo, I give up” I sputtered. “I’m a guy, and guys read newspapers, not minds. What the hell are you talking about?” I was somewhere between being very confused, and feeling like the stupidest person on the planet.

“Jim, I’m scared!” she almost screamed at me, then regathered her cmposure. “I was over a Sarah’s last night, and we were . . . well . . . fooling around, you know? Anyway, Sarah got some booze from her old man’s liquor cabinet, and we got a little drunk. Somewhere along the line, we started talking about . . . sex, among other things. She asked me if I’d ever kissed someone, you know, on the lips? So I told her the truth, no. Suddenly, she leaned over and kissed me! Not just a little peck, either, but a full-blown, open mouth, tongue swapping, french kiss. At first, I was shocked, but the longer she kissed me, the more I began to enjoy it. The next thing I knew, I was kissing her back!”

“Umm, I don’t think one kiss would qualify you as a lesbian, Jo” I advanced an opinion. “The booze might have had something to do with it, and with the way it felt.” The look on her face told me that my reassurances hadn’t done a damned bit of good.

“It . . . it wasn’t just one kiss, Jim. There were lots of them. We must have kissed for almost an hour. Then Sarah grabbed my boob, and began to squeeze it, playing with my . . . my nipple, too. And you know what? I loved it!”

I took the time to let her words sink in. Hell, she was sixteen, and probably as curious about sex as I was, and maybe more so. But like me, I was pretty sure that she was still a virgin, which would explain why a kiss would spark her interest. The fact that it was from one of her girlfriends was a little hard to understand for a guy like me, but then, I wasn’t all that knowledgeable as to how a girl’s mind worked.

“There’s more, isn’t there?” I quietly asked. The look in her eye told me that those kisses were just the beginning.

“Yeah, there is” Jo continued. “When she grabbed my boob, and began to play with it, I did the same to her, and it felt so wonderful. I just knew how to touch her, to excite her, to give her the same kind of pleasure she was giving me. We kept on kissing, and playing with each other’s tits. Jim, I couldn’t stop! I just wanted to feel her boobs, and how hard her nipples got! Pretty soon, we were on the floor, and Sarah lay on top of me, pulling my shirt and my bra off, then taking hers off as well. When she mashed her tits against mine, I thought I would die, it felt so good!”

Joanne took a deep breath, letting it out slowly before going on, as if to bolster her courage. Then she looked deep into my eyes, and if I had any questions as to her femininity, they disappeared in that one second. She must have found that courage she needed, because she went on with her tale.

“Jim, Sarah reached down between my legs, and began to rub me down there, and it felt absolutely fabulous! I followed her lead, and the next thing I knew, we were both naked, touching and feeling each other, and I couldn’t get enough of her fingers tickling or teasing me! Sarah was so wet, and so slippery. I loved that texture of her sex. She began to finger me, and I thought I was going to explode, it felt so heavenly! I wanted to do the same to her, to make her pussy feel as good as she did mine. Then Sarah must have had an orgasm, or something, because she began to moan and groan, and I felt her shaking and shuddering. At first, I didn’t know what was happening to her, but she pulled me tighter to her, then shoved herself down on my fingers and made sure I couldn’t pull them out. God, she must have shook like that for over a minute. When she was done, she started playing with me some more, and the next thing I knew, my pussy was tingling, my tummy got all fluttery, and I felt like I was losing control of myself! And the scary part? I just didn’t care! Whatever was happening to me, I wanted it more and more! I guess I must have gotten those same shakes that Sarah got, because all I can remember is that I felt like someone had zapped me with electricity. My head was swimming with what seemed like bright lights! Al I could think of was that I wanted Sarah to keep doing whatever it was she was doing to me!”

At that point, Joanne dropped her gaze from my eyes, and began to stare at the floor again. All this time, I’d been holding her by the shoulders, but I had a burning desire to hold her tightly in my arms. As I did, the tip of her nose rested against my Adam’s apple, and I kissed her forehead again, holding my lips to her in an attempt to tell her that everything would be alright. It may have been a pipe-dream, but I had to try. Then once again, I pulled back just enough to look into her eyes.

“Sis, it sounds like you two had your first orgasms. Not being a girl, I’m only guessing, but it sure sounds like it. That’s a good thing, in that now you know what to expect. But I doubt that makes you a lesbian.” I had to ask her the next question, if for no other reason than to help calm her fears. “Sis, can I ask you something personal?” I waited for her response.

Jo looked up at me, not sure whether or not she wanted to open herself up that much to her brother, but she swallowed hard, then nodded her affirmation.

“Have you ever been with a guy? I mean . . . well, you know what I mean. Have you let a guy into your pants yet?” I got a resounding smack for my trouble, and it hurt like hell, although I think a lot of it was the shock of my little sister actually striking me, more than the impact of her hand on my face.

“Oww!” I screamed. “What was that for? Shit, I asked you if it was okay, and I told you it was personal. You didn’t have to smack me like that!”

“Whether I have or not is none of your fucking business!” she snapped. “And just for your information, no, I haven’t!”

“Okay, okay! But you didn’t have to smack me. It may not be any of my business, and it really doesn’t matter to me, personally. Hell, it’s your body, and you can give it to anyone you feel comfortable with, for all I care. But I had a reason for asking, and it sure as fuck wasn’t to be nosey, or nasty. So, can we try that again, without the slapping and hitting?”

My sister looked into my face, and I could see her remorse staring back at me. She leaned up and kissed me lightly on the jaw bone, then pulled me tight to her young adolescent body, almost as a sign of desperation for the safety of someone’s embrace.

“I’m . . . I’m sorry, Jim. I shouldn’t have done that, but your question just made me furious for a second there. I guess I lost it. Forgive me?”

“Umm, shouldn’t have done what, Sis? Slapped me, or kissed me?” It was an attempt to break the tension, and it must have worked, because my sister actually began to smile, for the first time since she’d walked into my room. That smile made it completely unnecessary to answer with words, and I kissed her forehead one more time.

“Jo, if you haven’t had sex with a guy, how the hell are you supposed to know what you want? So you and Sarah had sex together. So what? It’s probably no big deal, and I’ll bet she’s feeling as unnecessarily guilty as you, right now. And I’ll also venture that you two aren’t the only girls to experiment with another girl, either. But until you’ve had sex with a guy, don’t bother labelling yourself as straight, lesbian, or even bisexual! You have no way of knowing until you have all the information . . . and right now, you don’t!”

Joanne stared at me for the longest time, her little mind whirring with thoughts and schemes. I could hear the gears going around, and some of the teeth weren’t lining up quite correctly, I swear. She had something devious that she was plotting, that I knew by the expression on her face.

“There’s one way to find out, Jim” she said softly. “You and I could have sex . . . couldn’t we?”

“Jo! What the fuck are you talking about? I’m your brother! That’s wrong, and you know it!” I almost screamed at the top of my lungs. And yet, her idea got caught in the cobwebs of my mind. My sister sure wouldn’t qualify as the ugliest girl in the world, that’s for sure. Okay, maybe she wasn’t as developed as some of her friends. Even at sixteen, she was still only an A-cup. She’d asked me, several times before, when she’d finally get bigger boobs. I tried to chalk it up to her being a late bloomer, and had always assured her that one day, her bust would fill out. In point of fact, it never did, and even today, a few decades later, she’s still an A-cup. On her, though, it looks good.

“Besides,” I went on, “Mom and Dad are home. If we got caught, there’d be hell to pay, and you know it!” It was an excuse, and a pretty flimsy one, at that. She still had the prettiest face I’d ever seen, a lean and trim body, if somewhat flat-chested, soft and gentle curves to her waist and back out to her sensuous hips, then down to a prominent butt that projected out from the small of her back, slowly returning to those firm thighs that topped her legs. And those legs! Of her five-foot-four-inch height, I sometimes swore that the first four feet were leg! God, they were gorgeous!

“Are you saying that you wouldn’t want to have sex with me, big brother?” she threw in my face, knowing what the real answer would be. I’d have to be a eunuch to not get turned on by her body! But she was my sister, for God’s sake! And yet . . . and yet . . . .

“Oh, for Christ’s sake, Joanne. That’s cheating, and you fucking-well know it!” I snarled in exasperation. “You know damned well that if I ever had the chance to make love to you, I’d grab it. But we can’t tonight, and by tomorrow, you’ll have changed your mind . . . right?” She continued to look at me with that conniving stare, leaving me guessing at what her answer might be.

“No, I don’t think so, Jim,” she finally declared, “unless you don’t want to. If Mom and Dad weren’t right downstairs, I’d have sex with you in a heartbeat, to be honest. You may be my big brother, and it may be wrong, but you’ve always turned me on, in your own, sweet way. But, if you really don’t want to . . . “

The turmoil in my head was almost bad enough to take an aspirin for. Here I was, talking to one of the prettiest girls I’d ever met, her wanting to get into my pants – there’s a switch! – and I was choking because of what? Because she was my sister, for crying out loud!

Somewhere in the cosmos, there’s supposed to be some kind of supreme being that looks down on us, attempting to guide and nurture us. I don’t know if any of that is true, but if it is, he’s a sadistic son-of-a-bitch, in my opinion! And right then, he was probably laughing his guts out, knowing how badly he had me squirming! I could think of quite a few names to call him, and most of them went through my head, missing my vocal chords by mere fractions of an inch. ‘Fuck you’, I thought.

“Okay, just supposing we did go through with it, Sis. Where do you propose we do it, and when? Tonight’s out, obviously, but what about tomorrow, after school? Mom’s working until four, so she won’t be home before five, and Dad never gets home much before six.”

Shit, I was really grasping at straws here, but the thought of being with Joanne, feeling her soft and smooth skin, her warmth, her femininity? There was no way I could pass that chance up! Maybe the excitement and taboo of incest was another driving factor, but it felt thrilling as hell to think about!

“Okay, tomorrow, after school, then" Jo volunteered. "Do you want to meet me here, or should we walk home together? We don’t, usually, and Sarah might get a little suspicious if we do. But I’d like it if we did walk together, if for no other reason than I enjoy being with my big brother, sometimes” she suggested.

“Yeah, that might be kind of neat, walking home with you. But why not walk with Sarah, too? We just won’t let her know that we’re going to be . . . you know. No one would suspect a thing if Sarah was with us . . . would they?” I threw in. We discussed some minor details, but finally agreed that we’d all walk together on the way home, and try to make it seem like a coincidence that Joanne and I happened to be on the same street at the same time. That was another detail we had to orchestrate, but my little sister seemed to think she had it taken care of.

The next day, it was all I could think about, this liaison between my sister and I. The day seemed to drag, and my thoughts were everywhere but on my schoolwork. Even my math teacher snapped my head off for making so many mistakes in class, and I’m good at math. Our lunch break was only an hour, but it felt like a week. I kept looking around the cafeteria, trying to find Joanne in a sea of four thousand other students, but with no luck. It was probably for the better that I didn’t, for I’d have had no idea what to do if I did find her.

Joanne had arranged it so that she and Sarah would just happen to be by the side door as I came out, then she’d call out to me, and we’d go from there. I tried to act casual, and to this day, I still think I should have won an Oscar for my performance. But we did manage to pull off our casual meeting at the side of the school, walking and talking like we sometimes did, whenever it became necessary to make the trip together. That was something that happened during snowy weather, but today, the sun was out, the grass was green, and it was pleasantly warm. Oh well, I thought, close enough for what Jo and I had in mind. Yeah, right!

Most of the talking was between Sarah and Joanne, with me eavesdropping like a snoopy brother, and keeping my big mouth shut. I don’t think Sarah even knew I was there, half the time. She kept commenting on this boy, or that person, speculating on whether they were interested in her or not. I knew the answers, but I wasn’t about to deflate her ego with the truth. My gut instinct was that Sarah desperately wanted to get laid, and she didn’t seem particularly fussy about who took her cherry.

If she’d only known what Joanne and I were about to get into, she’d have wet her panties!

Finally, and I do mean finally, we arrived at the house, and Sarah said her good-byes for what seemed like a month, then eventually turned and left for her own house. I was so tempted to run up the stairs and through the front door, but that would have broken the illusion. We sauntered up and into the house. As soon as that door closed, though, the illusion was no longer necessary, and we sure didn’t waste any time. I had just enough time to hang my coat up and remove my shoes before my sister threw her arms around me and pulled me to her hungry lips. Somewhere in the process, I dropped my books, hitting my toe, but never felt a damned thing.

Instantly, my little sister became the Alpha and Omega of my conscious world. Her lips tasted so damned good, and when her tongue began to trace across my lips, I would have danced on hot coals for more of her kisses. She demanded that I grant her access to my mouth, and I willingly surrendered. Oh God, could that girl ever kiss, too! She ran a probe over my upper teeth, flicking the tip along my top palette, then running over every surface of my tongue. Her passion sent shivers up and down my spine, and I held her to me as tightly as I dared, almost as if I was afraid that this was all a dream, and I might wake up. We must have stood just inside the front door, kissing, for fifteen minutes or more. By then, my blood was no more than one or two degrees off the boiling point.

“Still interested?” Joanne quizzed me. I kissed her one more time in reply, and she melted in my arms. As we finally broke our lip-lock, she almost ran up the stairs, then stopped at the top landing, waiting for me to both catch up, and to indicate which of our two rooms I preferred. I chose my own, simply because that’s where I figured we’d be the most comfortable. As soon as I guided her into the room and closed the door, Joanne pulled her top off, then turned to me with just her white bra covering her underdeveloped breasts, and beckoned me to her again. As I began to kiss her soft, sweet lips, my hands migrated to her diminutive mammaries, pressing and squeezing her deliciously pliable skin through the fabric of ...

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