In the Darkness of Her Night

P used just the one finger to move slowly in and out of J's ass, completely withdrawing a few times to add more lube. She kept gazing at J, occasionally sucking on one of her own fingers as if it was a lover's clitoris. Then she gave J another probing with her tongue before entering two fingers. Slow, gentle movements, in, out, side to side, frequent pauses, twisting her fingers ever so gently in J's ass. She could have been J's secret lover. I watched J's head carefully. It was moving just a bit. She was moving her head side to side ever so much. What was she feeling? It was unlikely to be pain. P was much too skilled. Pleasure, possibly, but J knew where she was. Fear was a more likely emotion. But then, I wondered, could it be anticipation? That was simply too delicious. It was also unlikely.

P removed her fingers slowly, licked them as a cat licks her paws and her other hand went to her own smoothly prepared vulva. Her hand was moist with the lubricant which she massaged over her labia and down to her own ass. Then she put the two fingers in J again, this time working her ass to stretch it, but not forcefully. That was to be my pleasure. Her other hand worked her own self, and I could P shiver as well. As P slowly got more aroused and moved her fingers in J, I felt my penis respond. As P worked herself she was moving her hips and grinding herself against her own hand. A few minutes passed. My erection steadily gained. I resisted the urge to masturbate, as that was P's pleasure. Mine was about to start.

I stood up and walked over to see more closely what P was doing to herself and to J. I knelt down beside P and caressed her neck. She purred. I gave her ear a slow, gentle nibble. This time she arched, stretched and turned to offer me her tongue. I gave it a not so gentle nibble. She left her tongue extended and I sucked on it for a few more seconds, then let her get back to concentrating on other more important things. She did. She always did. I truly loved to watch this woman work.

P was really into herself now, physically and emotionally. Two fingers in her vagina, straining to reach her own G spot and very likely succeeding. She took her other hand away from J and squeezed her own clit shaft, moving it up and down. She started to rock on her hand. I knew it wouldn't be long before she climaxed. I wondered if she thought that this time would be different. I wondered if she was thinking about anything but getting off. I waited about thirty seconds as she started to climb to a peak and said "Stop". She did. She stayed there, panting and rocking, but her hands were on her hips. I let her stay that way for a minute as she slowly backed down from her unfulfilled emotional and sexual rush. My penis was now as full as it would be. P stood up and waited by the horse, facing me.

She rubbed some of her own wetness on my penis and sighed. J was motionless. Silent.

The rule was no damage, at least physically. J's ass was ready. It was well lubricated and partially stretched. I didn't know if she had already been anally violated. Most likely yes, but I didn't care. If I wanted an anal virgin, they were everywhere.

J was now my expertly prepared anal fuck toy. I wanted to abuse her, to feel her ass give way and accept my penis. I was thicker than two of P's fingers by a considerable margin but I didn't want to damage J's ass. I just wanted to fuck it. J was stretched over the horse, immobile, already vaginally fucked, and now P had prepared her ass for my pleasure. P had also prepared me with her show of finger fucking in J's ass and masturbating at the same time. I stood up, glanced at P, and then motioned to my erection. P reached for her suit jacket, took out the condom, opened it and unrolled it onto my penis. She sensuously applied a liberal amount of lubricant and gave me a minute or two of her ever so special hand attention. Her work was not over but I didn't need her for a while. She would stay, she would watch but for now she was not needed. I was ready.

The first stroke into a new girl's ass was important. The rule was important. If a girl was damaged, reparations had to be made. This was not a serious concern, but if a club member complained about damaged goods too often, then club membership was at stake. This was important. The first stroke required a little care. Almost like entering your own lover's ass. Not quite, but similar.

I put the tip of my penis against J's ass and held it there. No violent thrust this time. I could fuck her ass and was going to. I just couldn't make it bleed. It was simply a matter of slow and steady pressure. J likely knew what would happen if she didn't try to let her ass ring relax. They always knew. I knew it might take a few seconds, maybe longer, but the result was inevitable. My penis slowly worked against her ass and I felt it stretching her rim. Then her ring started to open, quickly shut, then partially opened again as she struggled to control something she was not used to controlling. I had no problem controlling the pressure of my penis against her ass. As I felt myself starting to overcome her anal tension and her muscles did relax a barely perceptible amount, my penis slowly entered, and my head was past her ring. I paused to feel her anal muscles quivering, unused to this presence. J was able to keep quiet except for a slight groan. Good. I glanced at P. She smiled.

It was now fuck time. It was time to fuck J, fuck her ass and fuck her dignity. Fuck her. I slowly went in deeper. J tightened around me and let out another slight groan but she was helpless. Good. Fuck J.

Deep was not important. Pounding her was not only unimportant, it was unadvisable. Rules. It wasn't so much that I just wanted to fuck J in her ass. I was doing that. I would continue to do that. I wanted to fuck J in her ass and then some. I wanted to fuck J in her head. And she was going to help me.

"J, I want you to listen. You must listen. Don't talk, just nod your head. Do you understand?' J's head nodded yes. I was very slowly moving in her, an inch or so only. Just inside. Gentle. Like ass fucking a lover for her first time. Not withdrawing, just back enough to feel the head of my penis pull back to her ring. No further back. Having a decent head, a little wider than my shaft was a blessing. My penis was made to fuck ass. J was going to learn.

"J, in a while we are going to play a little game, But for now you do as you're told and I will make this as easy on you as I can. Do you agree?" J nodded yes. As if she was going to do otherwise. "Good. For now just don't do anything." I glanced at P. She smiled. I continued to move in J. As usual, P had done well. J was well lubricated and her muscles were not too tight around me. Tight enough that I knew I was fucking her ass, not her vagina, but it really felt quite good. I slowly worked in a bit, a little deeper. J was breathing very steady. I knew she was fighting to keep herself in control. They always do. At least at this point. My friend's sister didn't but that was different. No rules applied.

For a few minutes I just slowly and gently ass fucked J. She was silent. Her body was tense under the stretch of the horse, but she was in no real discomfort. At least she gave no indication. Her ass cheeks which had been so taught at the first touch of my penis and had visibly contacted at my first penetration were now fairly relaxed. Was she OK with this? No I thought. She just wants it to end. Good. I kept the ass fucking going and glanced at P, then motioned to my penis, still stroking in J's ass. I slowly backed up and felt the ring, and then eased my way out. J's ass was good. It was actually very good. P put a little more lube on me and some more on J.

I held my penis to J and waited only a bit as I pushed steadily. This time I entered before waiting for any sign from J that she was trying to relax for me. She let out a slight gasp but nothing untoward. Fuck her. She was my anal fuck toy, I was anally fucking my anal fuck toy and she was learning to accept her position. I watched her cheeks contract at the penetration and smiled. Her anal muscles tightened and she was squeezing on me, but not because she wanted to. Good. I stroked a little faster, and went a little deeper. The anal fucking of J continued.

I came out, and went right back in. Forced penetration is so much more degrading than just being there. I liked to see my penis entering her ass again and again. I gave myself the pleasure. P was good and added a bit of lubricant every third or fourth time. I liked it to be smooth, well oiled and slightly tight. I enjoyed feeling my penis head against her ring, effortlessly expanding it to glide in, then draw back and over it and out again. All J consisted of now was a smooth and luscious ass, oiled and hot, deliciously tight, so helpless and exposed. My own private anal fuck tunnel. J had a good one. I felt a slight tinge of regret that this was my only chance to enjoy it. Rules. However there would be others. There were always others. In and out of the club, there were always others.

J was squirming a bit at this continued anal penetration but she was unable to make it stop. After I had penetrated her ass a few dozen times, I just stroked in her, shallow and gentle, like before. After a few minutes, J was breathing deep and steady again, but a bit faster. Her skin was flushed and wet with glistening sweat. She was struggling to maintain control. With the lube, her ass was accepting my penis rather well, but I could feel her muscles quiver around my shaft, then stop, then quiver again. She was struggling. Good. I wondered if she was thinking about how this would end. The anal fucking of J was about to really start.

"J, its time for the game to begin. This is what I want you to do. Will you listen?" J again nodded yes. I continued to stroke in her, my penis getter even harder at the thought of what I was going to do. "J, it is very simple. I want to come in your ass, but I want you to help me. Do you think you can do that?" J hesitated, perhaps not understanding what I meant. I thrust into her, deeper than I had and grabbed her hair, pulling her head back. I thrust into her hard and fast a few times, then forced my way into her ass as far as I could and held. J gasped out loud and her whole body shook. J tried to nod yes but my hand pulling her head back wouldn't let her. I let up on her hair and she nodded yes. The squeezing of her violated ass around my thickened and throbbing penis was ecstasy.

I went back to slowly love fucking her ass. As if. P was starting to breathe a bit heavy as well. She looked at me with her eyes lit up and touched herself. I frowned at her. She stopped. The anal fucking of J was going well. The head fucking was about to get serious. But first, I enjoyed a few more minutes of pretend love fucking, as if to calm J a bit. I smiled. I was in no hurry.

"J, if I have your attention, I will explain. Do I have your attention?" A slight nod yes. J was in pain. I could tell. After the quick, deep violent anal thrust, they usually were. The sister was beyond pain, but that was different. I kept on with the slow, almost gentle ass fucking and waited for J to recover as much as she could. When I felt her ass relax a bit and saw her body tension level fall, I continued with the rules of the game.

"J, all I want you to do is this. I want to fuck your ass until I come. I want it to be like this, slow and gentle." I was slowly working in a bit deeper now, as deep as I felt necessary and was again almost fucking her ass like a lover would. "Now listen. What you do is this. As I go in, you relax your ass. And as I come back I want you to squeeze on me. That's all. I want you to massage my cock with your ass until I come. Do you understand?" I gave her a few seconds to comprehend and she nodded yes. I withdrew out of her ass. I glanced at P and she smiled. She remembered this game. I did it every now and then. P put a final bit of lube on my penis and a bit on J, just above her ass and we both watched it slide down and I started.

"Remember, relax as I enter, squeeze as I withdraw. I'll let you know how you are doing." J nodded yes. . Good. As gently as at first, I entered her ass. She was getting quite used to it now. I slowly glided in, her ass just comfortably tight around my shaft. I paused. I felt her squeeze on me. I slowly drew back, just to the point I was against her ring. I was good at this. I smiled. I felt her relax a bit.

"Good, J, very good. I think this will go well for both of us. I started in again, then paused, felt her tighten around me, and I drew back. We kept that up for a few minutes, a slow, gentle ass fucking. She really was doing well, all things considered. A few slips on her timing but I was pleased. The massaging ass fuck of J was going well. I was feeling like a slowly tightening spring. My body was getting going, my penis was being treated very well by J's ass and my mind was drinking in the liquor of the night. I let myself start to make a few appreciative noises. I wanted J to think she was doing well.

"J, this is good. This feels so good. I want you. I want to come in your ass. Your ass feels so good. Make me come. I want to explode in your ass. Squeeze me just a bit harder."

P smiled. I felt J work my penis a bit harder. The ass fucking continued. The head fucking was starting to go to my head. I wasn't sure but I think I felt myself thicken a bit more. Hard to tell when your penis is deep in a tight, well lubricated ass. I wondered how long J would be able to keep working her ring around me. It's not like she was used to it. She would tire, eventually.

"J, you are pleasing me. You are doing this for me and I want to reward you. If I keep this going, do you think you could come for me? I think you deserve to come." I waited. J was thinking. I didn't want her to have too much time. "J, it's OK if you think you can't. Please be honest. It's important."

J nodded no. I wasn't surprised. She knew she couldn't come this way and she knew enough not to lie.

"That's all right, J. I understand. But I want to feel you come. I want to feel you come when I'm in your ass. I want you to come for me. P will help you. She will help you come. P, I want you to help J. She deserves a bit of special care. Help her to come. Do it for the both of us." P smiled. And obeyed.

P sat down under J, between her legs, facing me, and moved her mouth to J's vulva. "J, it's important that you keep doing to me what you are doing now. That must not stop. Do not stop." J nodded yes. Good.

P started to work on J from her side while I continued J's ass fucking from mine. P was good. As expected, she seemed to enjoy her role. She was as gentle and tender with that part of J as she was with her ass. But J's ass was no longer P's concern. P gently probed, licked and sucked on J, using her hands, her lips and her tongue. She was careful to work J over in a lover's fashion, caressing her, kissing her, moving a wet tongue up and down J's inner thighs, pausing here and there to pay special attention to a special place. P really was like a porn star in a woman's twosome. She seemed to be unaware of me, of what I was doing, as if concentrating only on fully pleasing her helpless lover. J was slow to respond. It took at least five minutes. I wasn't surprised. She really wasn't in a position to enjoy what was happening in front of and behind her. She was trying so hard to match my rhythm, aware of what might be a penalty for failure, that it took that long for the first slight sighs to be heard. I wondered again, how long J could maintain composure and concentration, under this amount of tension, indignation, sensory stimulation, sexual penetration and degradation. I also thought about the fears she must be feeling, knowing what might happen if she did fail to do my bidding. She really was in an emotional bind. Head fuck. My kind of head fuck. My real reason for fucking J. My real reason for letting P do the same. It was only going to get worse for J.

P kicked it up a notch and started to finger fuck J. Two fingers, two of her long, well trained fingers. I knew she was alternately between simple finger fucking and then massaging J's G spot, all the while making oral love to her entire vulva. J was breathing more quickly now. Short, shallow breathes, the way a woman does when she is concentrating, trying to keep from losing it. I could feel that her anal efforts towards my penis massage were flagging. Tired muscles, or wavering concentration. Both was my guess. J was into this fuck session for almost an hour now. I was somewhat bemused by her perseverance. Considering what she must have already experienced over the past days and nights, and my imposed sleep deprivation, she was doing remarkably well. So much the better. The longer she held up, the longer I got to fuck her. I wondered if J had considered that. Of course the fear of what might happen if she didn't hold up might have a part to play. Either way, I would win. She may have understood that, and perhaps wasn't able to decide what way out might go best for her. Head fuck.

"J, you are not keeping my penis massaged as I want. Please don't disappoint me." An instant result as she tightened on me and put some effort into it. Good. How long could she keep that up? P, understanding the signal, kicked it up another notch. I could feel her fingers go into pure G massage mode. My penis, separated from P's fingers only by J's tender tissues, could tell exactly what P was doing in J's vagina. I also could tell P was now seriously face fucking J. Her head was moving up and down as her mouth and tongue concentrated on J's clitoris. P had one hand to own vulva now. I allowed that. She was earning that. I started to feel that I was not going to last too much longer. J was really working on my ass massaged penis and seeing P so into her work and herself was liquid sex, pouring down my throat, and going straight to my brain. J was doing exactly what I wanted her to do. Not that the physical fucking was something she could avoid, but she was compliant, to the point that I was ready to consider a finish to the session. My own personal fuck toy session. My vaginal, anal, brain and dignity fuck session.

J was arching her neck now, then moving her head back down, obviously trying to move more her pelvis but unable. I knew if she could move her pelvis, she would be grinding against P's face, moving on P's fingers and moving back onto me. She was, despite all of the pain, indignity and abuse she had been subjected to, trying to come. Perhaps she was using this as a type of emotional anaesthetic. Perhaps she felt it might simply be the best for her, doing what I wanted her to do. I would let her know just that.

"J, I want you to come. I want you to come as I do. I'll come in your ass as you come on P. You deserve to come on P's face. She wants you to come on her face, don't you, P?"

Her short gasps and barely concealed moans made it ever so clear that J was trying to do just that. Even if she hated herself for it, she was trying to come. And she was being helped along, not so much from my fucking, but definitely from the expert and passionate fucking that P was giving her. P, ever so well trained was backing off the face fucking, and continuing with her vaginal finger fucking. J could not move her pelvis but she could squeeze down on P's fingers and she was. My penis felt it. P stopped the facial work and simply held her fingers in J, forcing her to work her own vagina around the fingers. My penis massage was forgotten as J was lost in her own efforts to have a vaginal orgasm, the possibility of a clitoral orgasm being on hold. I waited a minute as P deliberately held J back, holding her finger tips to J's G spot, but only letting J give herself insufficient pressure, expertly letting her come close but not close enough. Head fuck time.