I Wish She Hadn't Ch. 02

I don't know why we didn't move to the bed right away - we would both have been more comfortable - but I suspect that we were too excited to take the time to do so. Instead, we used that big chair that Madi had been sitting in. It was kind of an unusual chair for a hotel room. It had this really high backrest and thick armrests on it, and maybe the attraction was the fact that I don't think either of us had ever seen anything quite like it.

I didn't know if we were going to start with anal penetration - that seemed like it might be something that we needed to work our way up to - but regardless, I figured I needed to get Madi ready, just as she'd done to me. So, once I couldn't get any harder, I encouraged her to stand, gently lifting her by her shoulders.

Once she'd risen to meet me, I started kissing her again all over - her face, ears, neck, and breasts, and then I turned her around and pulled that tiny thong off her. The back of it was only a string that ran up the length of Madi's ass crack. She had such a nice butt, really shapely and full, and when I pulled it off her hips and down her legs, you can probably guess what I found protruding from her tight backdoor!

I turned her around, spread her legs wide, and with her right leg resting on the floor, I lifted the other one so it was supported by the armrest on the chair's left side. Madi had to brace her right arm on the other armrest, and now she was leaning back, so that I had full access to her pussy. I knelt between her legs.

I started, as usual, just by licking her opening, and as I didn't want to make her cum just yet, I steered clear of her clit. Pretty soon, I began to penetrate her leaking slit with two fingers from my right hand, and then, since it had worked so well the night before, I started ringing her doorbell again, pushing the pink jewel in her ass in and out with the thumb of my left hand, while I continued to lick over and around her clithood as I fingered her pussy.

She started breathing faster, and I knew I couldn't keep that up for long without sending her spiraling into another powerful orgasm. I didn't want that at the moment. I wanted to be inside her and to make her cum with my cock.

So, without asking permission, I pulled away, and then, in one motion, turned her around, lifted her left knee onto the armrest, while her other leg still rested on the carpeted floor, and positioned myself so I could take her from behind. Since my access to her ass was obstructed, I decided to take what was presenting itself to me. Besides, I didn't have any lube, so as excited as I was to explore that forbidden place, I decided that, at the time, it was preferable to concentrate on her other hole.

Madi was plenty wet by now, but I still worked tentatively. I bent her over, and placed just the tip of my cockhead inside her opening. Then, I pushed ever so slowly, and, as I did, she let out the longest, most sensual groan, "Ooooooooooooooooooooooooohhhhhhhhhhhhhhhhhhhhhhhhh!"

Once I was most of the way inside her, I started moving. Madi tried clinging to the top of that huge backrest with one hand, but because it was so tall, she couldn't reach it. Instead, she could only put her hands against the front of it. With one arm stretching nearly to the top and the other directly in front of her, she used the backrest to push back against me when my plunges increased in speed and depth. She was purring non-stop now, and though she started fairly quietly, her vocal responses were building in volume when I heard the occupant of the next room turn the shower on.

I was concentrating on the sensory experience that morning. It was an incredibly distinctive feeling, and I knew that something was clearly different. I think my cock could vaguely feel the contour of that anal toy inside Madi as I moved in and out of her pussy, and I could tell by the expression on her face that having both of her holes filled was a particularly intense erotic sensation for her. Her mouth was open, and her eyes were closed, and the look on her face promised to get me to the same place I knew she was soon headed.

And then she reached down between her legs with her left hand. I couldn't see, but I was fairly certain that she was caressing her clit. Her other arm was still stretched vertically upward, and a moment later, I could see her open and close that right hand in a futile attempt to grab a fistful of leather. Madi had never touched herself before when we were fucking, so this was a new move, but within seconds of that inaugural act, she went off like a firecracker.

The sounds grew in volume and intensity as her climax started roaring through her, and I remember being grateful that our neighbor was in the shower at the moment, "Yes, yes, yes, oh, oohh, ooohhh, oooohhhh, cum... I... I'm... cum... I'm cum... Oh, I'm cumming. I'm cumming! Fuck, yes! Yes! Yes!" She kept screaming, but I didn't know what she was saying.

I don't know how long it lasted, but when she was finished, I got the sense that maybe that position was a bit of a strain, especially on her legs. So, I chivalrously offered another option. "Do you want to get on top of me?" I asked.

"Oh, thank you, baby. I don't know why, but I'm getting a little tired like this, and that would give me a nice break. But, John, I want you to know this - right now the important thing is to make you cum, so you take me however you want to - whatever way is gonna get you there the fastest. I want to concentrate on you, now."

"Okay, Madi, whatever you say!" I smiled at her as she looked back at me encouragingly. That was nice of Madi, but I already knew something about her and her own sexual proclivities - whichever position I chose and whatever I did to get myself off, I was certain to get her off, too, probably before I got there!

I withdrew from her, and helped her off the chair. Then, I sat back, leaning against that tall, leather chair back. I grasped Madi by her slim waist, running my hands over the thick fabric of that corset, and then I turned her around backwards, so that the laces that ran up the back of it were now staring me in the face. Then, I held myself around my root and wordlessly encouraged her to climb aboard.

She slipped my thick shaft into her wet opening and sat down on me with her legs straddling mine. I started moving again, and when I did, Madi leaned back in the saddle to accept my even more invasive thrusts.

And then we both realized something sort of magical almost simultaneously. When she was leaning back against me like this, her butt was resting on my pubic mound, and when I started stroking into her pussy, my pubic bone was in direct contact with the little, glass knob on her plug! Every time I thrust up and into Madi, I was pushing that toy deeper into her!

She commented right away. "Oh, my god! Do you feel that? Do you feel what you're doing to me?"

"I can feel myself pushing against your toy. Is that what you mean?"

"Yes, yes! Oh my god, yes! Oh, Jesus Christ! Oh, don't stop! Don't stop! Jesus, you're gonna make cum again! You're gonna make me cum!" It was funny how quickly she'd forgotten about the person on whom we were supposed to "concentrate", but it didn't matter. This position was really good for me, too, and when I realized that we were directly in front of the full length mirror on the other side of the bed, and I could watch my cock slamming in and out of Madi's tight pussy while her tits bounced up and down above that corset, I knew I was going to cum real soon. The fact that I was going to make her cum too was only icing on the cake.

I was holding her around her hips at the bottom of that black merry widow where her garters stretched across her taut ass to her fishnet stockings, and when Madi bent her knees and lifted her legs so that she could support her feet on the armrests of the chair, I realized I could stroke into her even more vigorously. I was pounding away now, grunting with every deep thrust, and I could feel Madi's pussy starting to squeeze me around the base of my shaft every time I pushed all the way inside her. When I was thrusting into her pussy, I was also pushing that toy against whatever it was that produced that intense and powerful climax the night before.

So, I really started going after it hard, leaning backwards and arching my back so that I could gain more leverage and pivoting my hips so that Madi was bucking up and down like she was riding one of those fucking mechanical bulls, like they showed on that fucking John Revolting movie - "Urban Cowboy" or whatever it was called. I have to confess, though, watching Madi riding atop me like that was not unlike watching Debra Winger in that movie. They even looked a lot alike!

We got there at almost exactly the same time. I had reached my top speed and deepest penetrations, and we were both making a really loud ruckus. And then, strangely, I heard the water shut off in the shower next door, and at that exact moment, we both slipped over the edge. Madi started to say it first, "I'm... I'm...", and I then finished her sentence... "...cumming! I'm cumming!"

I started unloading inside her, spraying my warm, viscous milk against the walls of her velvety pussy, a pussy that was convulsing around my engorged shaft in synchronicity to my ejaculations. In all, I deposited a good dozen jets of goo inside her, and Madi experienced an equal number of intense orgasmic contractions. Looking at her reflection in the mirror throughout, I could see her legs quaking and shivering, not with cold, but with the intensity of an orgasm that she was riding to its conclusion atop my non-mechanical bull.

It was pretty amazing, and what made it even more astounding was that the main attraction hadn't even started! When she was finally done, she climbed off me, and then my semen must have started dripping out of her, so she quickly ran to the bathroom with her hand between her legs to clean herself up before she leaked jism all over the carpet.

I stayed where I was, kind of slumped back in the huge chair, half exhausted even though it was only 9:35 in the morning. When Madi came back in, she was carrying the bottle of Astroglide. She set it down on the nightstand and then asked if I wanted to move to the bed.

I shrugged my shoulders. "Sure." I said. I wasn't really nervous anymore. I was all prepared for what was coming, and I was looking forward to it. I knew that since I'd already cum, I wasn't likely to pop off in her ass right away, and that was probably a good thing. But I was just a little tired and awful hungry, too, and I really needed that coffee.

"Do you mind if I take a short break for breakfast now, Madi? I'm kind of famished, and I could sure use that coffee."

"That's why I got it, John. Go ahead; we've got all morning. Hey, while you're over there, would you mind bringing me mine?"

I grabbed the tall cup of coffee she'd brought me, the brown, paper bag with the muffin inside, and her own half full cup of Joe and came over to the bed and sat down next to her.

"Thanks", she said appreciatively, as I handed her the paper cup.

"No, thank you, Madi! That was really nice of you to get us breakfast! This is going to hit the spot. Can I pay you back for all this stuff?"

"Fuck no! You drove; you paid for the room, for dinner, and for the cover charge and the drinks last night. It's the least I can do!"

"Well, thanks. I'm just glad you came with me. This is fun!" I reached into the bag and found some creamer for the coffee, as well as the muffin, which was fucking huge and really delicious. I poured the creamer into my coffee and stirred it with a swizzle stick, then put the lid back on and set it down on the nightstand. Then, I made a kind of plate out of the paper bag for the muffin and started in on it.

Madi watched with rapt attention, just sitting there looking sexy and sipping her coffee. After I'd taken a couple of bites and washed them down with coffee, I offered her an update. "By the way, I called a couple of friends while you were gone, and I think they're gonna meet us somewhere later today or tonight. Does that sound okay?"

"Sure. If they're friends of yours, I'm sure I'll like them. Besides, I enjoyed listening to those bands last night - they were funny!"

"Yeah, they were funny! Tonight, I think we'll probably see somebody that takes a little less comic approach. I have a couple of ideas; but I'll see what my friends think."

"Music's a big deal to you, isn't it?" It was an interesting question, because I think it was the first time that Madi had really tried to find out exactly what made me tick. Most the time, I think she thought that sex was the foremost priority in my mind. It really wasn't. I was just naturally horny like everybody else my age. But hearing her question, it struck me that she really didn't know me very well.

"Well... yeah. I mean... I don't know, I guess music and books - those are the things I get the most enjoyment from."

"Not sex?" She smiled at me like it was a joke, but I don't think it was. "You're like Tommy. He's the same way."

"Yeah, I suppose so. I guess that's why we're friends." I took another big bite of the muffin and was chewing away at it, and then I noticed that she was staring at me. I could tell she was thinking. And that made me think. For some reason, her bringing up Tommy bugged me just a little. Tommy was my friend and all, but I didn't like the idea of being compared to him. I was just starting to figure out where Tommy was coming from, and there were a few things about him that bothered me, not just a little, but quite a bit.

For starters, Tommy was sort of a latent misogynist, one of those macho fuckheads that I had spent the wee hours of last night thinking about. I had already heard and seen some of the things that he had said and done to Libby, things that I didn't approve of. It was like he thought he was better than she was because he was a man. I don't know why you would ever want to be with, much less marry, someone you considered lesser than yourself. Besides, Libby wasn't lesser. She was smart, funny, determined, and pretty, and Tommy, for all his good qualities, was a lazy fucker, and, it was already abundantly clear to me, that he was never going to change.

But even more than that, I already knew that Tommy would eventually do everything he could to prevent Libby from becoming the person she wanted to be. She'd already told him several times that she wanted to go to college to study nursing, and he acted like that was the dumbest idea in the fucking world. How can you love somebody and not want to encourage her to be the best version of herself?

All of a sudden I was thinking out loud. I probably shouldn't have, but I brought it up. "Do you ever wonder about Tommy? I mean, him being married to your sister?"

"What do you mean?"

"Well, have you ever heard him talk down to Libby? I mean, discourage her from doing things that you know she really wants to do?"

"Yeah, all the time, but that's just Tommy. He's not that bad a guy. He's just an asshole sometimes."

I laughed. "You might be setting the bar a little low, don't you think? Maybe he shouldn't be an asshole at all!"

"Well... you're right... he shouldn't ever be an asshole, but not everybody can be a good guy all of the time, can they?" She paused to reconsider that statement. "On the other hand, it's possible that you might be the exception to that rule!" She smiled at me with this look of unvarnished adoration, and it instantly made me really fucking nervous again.

"I wish that was true, Madi, but there are plenty of times that I've been ashamed by things that I've done or said - the way that I've treated people, even people I love. Maybe, you're right... maybe, we're all assholes some of the time." I paused and took a drink of my coffee, but I was still thinking about Tommy and Libby. "Still, if Tommy has to be an asshole, I just wish he wasn't an asshole to Libby. That shit bothers me." I took the last bite of my muffin.

"You like her, don't you?" She was staring at me with a kind of amused suspicion, not envy exactly, just a fascinated, newfound comprehension of something that she'd long suspected and now understood thoroughly.

I didn't even stop to swallow my food. I felt that question deserved an immediate response. "Of course, I like her! She's my friend! As her sister, I would think you would like that. Don't you want me to look out for her?"

"No, that's not what I'm saying. I mean, you're attracted to her. I can tell. You've got the hots for her, don't you? I think you have for a long time!" She was grinning at me with this all-knowing, kind of sarcastic expression.

"What are you talking about? I don't have the hots for Libby! She's married to one of my best friends, for God's sake! Besides, she's your sister!"

"But you already said that he's mean to her sometimes, right? So, if you're so worried about how 'one of your 'best friends' treats my sister, then I figure you have to have some feelings for her. Am I right?"

I was flabbergasted, and, I realize now, I was also lying. "No, you're not right! Can't I think that it's a bad thing when someone is mean to someone else without wanting to get into that person's pants? Shit, when I was in high school, I saw dozens of fucking assholes teasing the smaller, weaker kids, and it always fucking pissed me off! It wasn't that I was fucking in love with some freshman boy, some 98 pound weakling that the football players were terrorizing! I've just always felt revulsion when I see people acting like assholes to other people. And, by the way, it's not just guys that act like assholes - there are plenty of fucking, asshole girls that we'd all be better off without, too!" I certainly wasn't talking about her, and I wasn't mad at her either, but I wasn't entirely sure that Madi knew either one of those things at that moment, since I was so vehement in my denial.

"Okay, I'm sorry, John. I was just teasing you. But see, you've just proven my point - you are a good guy! You can't deny it!"

"A good guy that wants to fuck your sister?" It was my turn for sarcasm.

"Hey, come on, I've already apologized, and like I said, I was just teasing anyway. Besides, I figure if I fuck you good enough, you'll never want to fuck her, anyway!" She gave me that ironic, sexy smile of hers that I knew was a prelude to something else, and then she set her coffee down, got up on her knees, and kind of climbed up behind me. She wrapped her arms around me, and then she started running her hands all over me, rubbing them on my arms, my shoulders, my chest. We started kissing, and then she reached between my legs and started stroking my cock and playing with my balls.

It was bizarre for her to have brought all of that up right before we were about to embark on something that would catapult our relationship into a whole different galaxy. But the even weirder thing was I knew that what she had said about me and Libby was more than teasing, and more significantly even than that, I suspected she was right.

Moreover, she was right about just about all of it. I was attracted to Libby. I had been for a long time. I couldn't deny that, at least not to myself. And since I couldn't have Libby, I was lucky enough to have a proxy. It was like what I said earlier - I think that fucking Madi was a means to fuck Libby vicariously. But, that said, once I started fucking Madi; that was enough. I didn't need to fuck Libby.

"Are you ready for this?" I asked once she had gotten me hard.

"Absolutely!"

"How do you want to start?"