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 .