my knees, I quickly moved behind her and put my hands on her hips. She lowered herself so that her head rested on the bed, leaving her hands free to reach behind and spread her cheeks for me, and exposing the crinkle of her anus. Sis had gotten me hard enough that my dick was pointed more at the ceiling than where she wanted me to put it, so I had to release one of her hips so that I could lever myself down. Edging myself forward, it didn't take long for me to get positioned so that the head of my penis was pressing against her rear opening. With both of us ready, I tried one last time, telling her 'Sis, we don't have to do this -' now, or ever.' She responded by saying 'No, we don't have to; but I want to find out, okay? I promise, if it hurts, I'll let you know.' At that point there was nothing left for me to say or do -' except what she so obviously wanted. Holding myself steady and in position, I began slowly and carefully easing my hips forward. I could feel myself slightly spreading her nether entrance, but what really surprised me was that I could tell she was deliberately trying to relax herself there to make it possible. When that little gem of discovery finally sank in, I realized that I not only could, but should, be trying a little harder to get into her. Gently increasing the pressure I applied against her opening, I could feel it slowly spread to accept me even more as Sis told me 'That's it, Danny! Like that!' As I pressed myself more and more against her, the tight ring of her anus went through a number of cycles: first tightening slightly, then relaxing and opening up to me even more as Sis voiced her pleasure and encouragement to me. Finally, it happened: with a suddenness that I think surprised both of us, my dick finally slid through -' accompanied by a soft squeak from Sis -' leaving her anus clenching me just behind the head. I was so worried about hurting her that I almost pulled myself back out of her before I realized that the noise she'd made had been one of surprise, not pain. Even so, I couldn't help asking 'You okay, Sis? Should I pull it back out?' 'Don't you dare! Oh, God, it feels so weird. Good, but weird!' A few moments later, she told me 'That's it -just hold still for a bit. You aren't hurting me any, but it's still going to take me a little bit to get used to it, okay?' before releasing her hold on her ass cheeks in favor of reaching forward to fill her hands with the bed covers, clenching them so tightly that I could see her knuckles turn white. As instructed, I held myself steady in her -' delighting not only in the warmth of her bowels, but how she felt around me as she slowly adjusted to my presence in such an intimate area. Since I could feel it as she got used to me and became more and more relaxed, I wasn't surprised when she finally told me 'Okay, Danny, I'm ready. You can go ahead again.'
'I don't think the rest of it will be too tough, Sis. I mean, what's already in you is the biggest part.' I could hear a trace of relief in her voice when she said 'Yeah, I guess you're right. But you'll still stop if I tell you?' 'Of course I will!' I answered. Still, I gave it an extra few seconds before beginning to ease my hips forward again; I had nearly half my cock buried in her ass before she asked me to hold still again, which I quickly did before I heard her say 'You aren't hurting me or anything, so don't worry. I just need to catch my breath, is all -' I've been holding it without even realizing it!' A minute or so later, she told me 'Okay, go ahead, again, like you did before.' With my cock firmly in place, I moved my hand back to her hip to help steady myself before pressing into her again. It wasn't much longer before I felt her anus clenched around the base of my penis; below, my balls were softly resting against the cleft of her sex, and I could feel them being wetted slightly by the overflow of her oils. Leaning forward and supporting my torso with my arms, I was able to lower my head enough to kiss her on the back of her neck -' causing her to shudder slightly before she told me 'That's it, just hold still again.
Jeez, it feels like I've got one of your baseball bats inside me!' Even though I figured it was where I was more than how much of me was there, that last part still did wonders for my teenage ego. Supporting myself with just one arm, I was able to lift my hand and begin playing with her breasts to try and help her relax. After gently squeezing them, and softly pinching her nipples for a couple of minutes, I gradually worked my hand down to her pelvis. There I collected a goodly sample of her oils and used them to keep things lubricated as I began teasing her erect clitoris. As I'd figured it would, the extra attention did wonders on helping her get used to having me filling her bowels; it was only a few minutes before I was able to bring her to an orgasm. As glad as I was to be able to help her that way, I damn near ended up regretting it, too: the sensations she created around my penis as it happened damn near had me blowing my load in her, ending things before they'd really gotten started. It got a hell of a lot closer than I'd have liked, but I somehow managed to keep from filling her with my cum, so I was more than ready when Sis had gotten her breath back again and told me she was ready. I started backing out of her real slow -' as much to try and get a little more control over myself as in sheer delight in how it felt to be moving in her that way. I only slid about a quarter of my erection out of her before easing it back in again just as slowly: we'd gotten that far without hurting her, and I was determined not to do anything to spoil that record, so 'take it easy' was the rule I was operating by. That seemed to be just fine with Sis, too, since I could hear her pleased moan when I began entering her again. The next time was marginally faster and longer, as was the one after that.
Slowly, gradually, and most of all carefully, I did my part in Sis' and my first experience with anal sex. As things progressed, it came as no surprise to me that Sis got more and more excited, and more active -' even to the point of pressing herself back against me in response to my gentle thrusts. Even without any direct stimulation of her clitoris, she still had a small number of orgasms; the first fairly small, but each one after that progressively stronger. We'd gotten to the point that I was quickly and steadily stroking in and out of her for nearly the entire length of my cock when I realized that she was getting closer and closer to having one Hell of a powerful climax. That was just fine with me, since I was rapidly approaching my own release and certainly didn't want to disappoint her. I was on the very edge of emptying myself in her, and worried that I'd failed her when I felt her begin to tighten around me even more with the approach of her orgasm. That was all it took for me, and after a couple more quick strokes into her, I buried myself as far into her as I could. I figured that if she climaxed from what we were doing, it was going to be much more powerful than anything I'd witnessed before; but I still wasn't ready for the power and volume of the cry she released when the first hot jet of my semen erupted into her bowels, or the way her opening clamped down on me almost painfully tight, or the way her body froze for several long seconds before going into a series of powerful spasms. The sensations she created around my cock were amazing, and it was only because of that added stimulation that I was able to generate the force needed to continue spraying her insides with my cum as her cry continued through the spasms wracking her young body. I was nearly done emptying myself in her when her scream finally tapered off, followed by a gasp and moan from her. I had no choice but to stay hard and inside her as she tried to catch her breath between the waves of pleasure I could see, and feel, coursing through her.
Still, even with the advantage of our young age, there was only so long that she could climax like that. When her energy finally gave out, the force of her orgasm quickly tapered off, leaving her exhausted. If I hadn't been watching for just such a possibility, she would have collapsed onto the bed. I'll have to confess that my motives weren't entirely altruistic: her anus was still clamped around my cock so tightly that I was afraid of what might happen if I didn't control her descent and keep myself close!
Holding her in my arms as we lay there on our sides, I was amazed to discover that Sis hadn't completely lost her senses: when I softly kissed her shoulder, she somehow managed to turn her head enough for me to hear it as she whispered 'Thank you, Danny.' I simply smiled at her and said 'That's okay, Sis. Just lay here and relax -' I could tell that hit you pretty hard, so just take it easy and get yourself back together, okay?'
She managed a smile and weak nod before turning her head to rest on the bed again. I ended up holding her like that for quite a while. Longer, in fact, than I expected I'd have to -' but she was my sister, and I loved her, and I was happy to do it. It didn't take long for her to relax enough that I was able to ease my hips back and more-or- less rescue my cock; when I slipped free of her, I was surprised as hell when she shuddered and released a soft moan. I was softly caressing her when she decided that she was ready to move again. She started to get up, but I easily held her down before telling her 'No, you just rest. If there's something you want, I'll get it for you.' Blushing slightly, she softly told me 'I'm starting to feel a little cold and – icky back there, and I was going to clean up a little and get something to drink.' I gave her a gentle hug before saying 'Fine, I'll take care of it. You just stay here and get your energy back, okay?' I could hear a trace of embarrassment in her voice when she softly said 'Danny, it's my butt!' I just smiled, kissed her shoulder, and answered 'Yeah, I know -' I was there, remember?', drawing a Look from her before I went on 'Look, I helped get you like that, so I can help fix it, okay? Besides, the way you look, I'd have to help get you to the bathroom and do it anyway; so why not just stay here, save your energy, and let me take care of it?' That wasn't anything she could really argue with, and after a couple of seconds, she nodded her acceptance. After another kiss to her shoulder, I got up and quickly made my way to our shared bathroom.
Once I had a couple of warm, damp washcloths and a small towel, I got her a glass of cool water and headed back. When I got into her room, I saw that she'd rolled over onto her stomach, making it easier for me to take care of cleaning her up. One washcloth got most of the lotion and the little bit of my cum that had leaked out of her. The second washcloth finished the job, and I used one end of the towel to make sure she was dry before folding it so that she could sit on it. That done, I helped her sit up with the towel under her. She looked at me in curiosity, and I
