I Wish She Hadn't Ch. 02

I think she realized now that I wasn't mad. She was smiling again, as she used the bedsheet to wipe the mess from her face, and then she spoke again with a little less difficulty. "I wanted to make you feel good, too. That felt good, didn't it?"

"Well..." I didn't exactly know how to answer her question. "Well, yeah, it felt good, but, Madi, I don't want to feel good at your expense. I'm not interested in humiliating you."

She seemed to have fully recovered now, and her bright smile was as dismissive a retort as anything she could have said. "I don't feel humiliated! I just made my boyfriend cum, that's all!" She was grinning now like nothing had happened.

This was a new development. She had never before used that word to describe me, and now it made me think hard, very hard. Boyfriend? Is that what I was? Is that what we were - boyfriend and girlfriend? More importantly, was there a promise or a commitment in anything I had said or done?

A mature human being would have known the answer to that question. Of course, there was a commitment. Any time you put your dick inside a woman, there's a commitment, and that commitment is even more solidified when that woman is an 18-year-old girl who has a crush on you.

But I wasn't a mature human being, and so there was no clear-cut answer to that question bouncing around inside my cerebrum. I had always prided myself on keeping my promises, and I had made a few to Madi. I had kept all but one of them, but that one was still hanging out there like the slab of meat dangling garishly between my legs. I was supposed to keep that promise that same day, but only after we'd been graced with sleep, followed by the clarifying light of day. Now, I wasn't sure I could... or should.

"Do you want to fuck now?" she asked bluntly. All her inhibitions were gone, and there didn't seem to be anything that could embarrass her.

But if Madi had lost all of her inhibitions, mine had returned with a vengeance. Still, I'm a coward, and as a coward, and even more accurately, as a born procrastinator, I lived by the motto, Nothing you can do today, can't be put off until tomorrow. "I don't think so." I said, with a kind of sad passivity. "Like I said earlier, I'm pretty tired." I could have said why I was passing on her offer. I thought it was pretty obvious, but she didn't question me any further.

"Okay... we've got all weekend." Madi was nothing, if not an eternal optimist. She was just happy that she was with me and that our long weekend together had barely started. She could wait. I, on the other hand, had to. "I'm just glad I made you cum before we went to sleep. I would have felt horrible if I didn't." There wasn't a lot I could have said, except to bring the whole matter out into the open, and, as I mentioned, I had already decided to kick the can down the road again.

"I'm gonna clean myself up", I said evasively, and I picked my underwear off the floor and headed into the bathroom. As I bathed my cock and balls with soap and a warm washcloth, I noticed Madi's new purchases set out around the sink, sans anal toy. There was an open bottle of Astroglide standing next to a box that read Fleet Saline Enema. Her clothes hung from the hook on the back of the door.

I dried myself off, put my underwear back on, and went back into the room, carrying the warm, damp washcloth. Madi was standing next to the bed, holding her G-string in her hand. She looked like she was just about to tuck her breasts back into her bra. "Do you want to use this to clean yourself up?" I asked deferentially.

"Sure. Thank you, baby! I think I'll use the bathroom, too."

She took the washcloth from me and retreated into the bathroom herself. I climbed back into bed, and a minute or two later, Madi returned, leaving the bathroom light on and the door just slightly ajar. She'd hidden her breasts inside that sexy, purple bra, and she'd donned the G-string over her garters. She set her new toy - which she'd apparently washed and dried - on the night stand next to the bed, I presumed to remind me the next morning of the promise I'd made.

Then, she turned off the light by the bed, climbed back in, and scooted as close to me as possible so that she could snuggle with me. She leaned in to kiss me sweetly for a minute or so, and then said abruptly, "Good night, John! Thank you for a wonderful day!" Within two or three minutes, her breathing slowed, and a minute or two after that, I began to hear soft, snoring sounds escape her.

I couldn't fall asleep at first. I lay there for a long time with my arms around Madi, watching her sleep and thinking. That may have been a questionable strategy. How can you presume a threat from someone who's sleeping so peacefully? She looked so young and innocent, and it totally disarmed me. I decided that I was one third in awe of her; one third infatuated with her, and one third afraid of her.

Mostly, I was thinking of the next day, or, more accurately, later that same day. I really didn't know what to do. On the one hand, I was certain that having anal sex with Madi was a risky enterprise at best. If she assumed that we were boyfriend and girlfriend after I'd penetrated her orally and vaginally, what did it mean if I penetrated her anally? It seemed like that would logically commit me to a much more serious relationship, at least in Madi's mind, not to mention mine. I figured that it would move our affair to another stratosphere entirely, even if my cock moved only an inch and a half or so from that orifice I had already spent a fair amount of time occupying.

But it really wasn't Madi's assumptions that bothered me. She had already proven herself to be a woman who did her best not to pressure her lovers. She'd had sex with three guys before she ever met me, and never said a word to any of them about how they'd neglected her own sexual pleasure. She didn't seem offended by my decision to stop making love to her mid-coitus earlier that afternoon, and she had asked me as politely as she could have if I was willing to try other forms of sexual experimentation. Now, she'd accepted my decision to decline intercourse. She certainly wasn't pushy and seemed more than content to, as she'd said, "roll with the punches."

No, it wasn't Madi that was the problem - it was me. There was only one woman who I'd had sex with more than three times. I don't know precisely how that woman perceived that affair, but I don't think any of the women I'd slept with considered me anything more than a consensual sexual partner. None of them thought of me as their boyfriend, and I didn't consider any of them my girlfriends.

But it was different with Madi. First, and absolutely foremost, she was Libby's sister, and that changed things for me. And besides Libby, I knew a handful of other people that were friends and relatives of hers. Just by making out with her the night of Libby's wedding, I knew I had committed to something - what exactly I didn't know, at least not that night.

And now that I knew how she felt about me - knew the power of her attraction to me - I felt like my reputation as a human being was on the line. I didn't want to turn into an asshole by disappointing her as much as I was damn certain I would... at least eventually.

On the other hand, I was really attracted to Madi. I liked her in whole lot of different ways. She was way smarter than she gave herself credit for, and she was really fun to talk to - funny and quick witted. And she was really nice, just a sweet, sweet girl. And she was nice to everybody, not just me, even though she treated me as if I was the fucking Prince of Wales.

More than that, she was the prettiest girl I had ever been with, and I found her undeniably sexy. I couldn't get the image of her all gussied up in her lingerie out of my head. I kept imagining what she'd look like wearing that merry widow corset, thong, garters, and fishnet stockings. I knew seeing her like that would drive me crazy with desire.

Lastly, and most selfishly, I really did want to try anal sex. I think I had subconsciously wanted to try it for some time, and now I was with a woman who not only wanted to, but one who'd gone to a tremendous amount of effort to plan the whole thing out. I didn't want to back out, and I knew I couldn't.

I don't know how long I lay there thinking, but eventually I fell asleep, and when I awoke, Madi was gone! I couldn't figure that one out. I looked at the clock. It was only about 9:00 a.m. and then I noticed that her toy was not in its place on the nightstand. Where in the hell had she gone? And why had she taken that with her?

I was a little worried at first. I thought maybe I had offended her by turning down sex, and that she'd left in disgust (and taken her toy with her!). But that didn't make any sense to me. Her last words to me last night were, "Thank you for a wonderful day!" It didn't seem like she was mad, or even all that disappointed in me.

Then, I thought that maybe she had gotten up and was in the lobby or was walking around downtown somewhere. She seemed to have liked it when we walked around in the afternoon, and when I looked out the window, I saw that it was another beautiful day. That must have been it. That assumption seemed to calm me down a little bit.

I figured I would just wait. I decided I would use the time to call a couple of friends of mine to see if they wanted to go out and hear some music that night. My buddy Pat was already up and moving around when I called, and he said that he and his girlfriend Abby were already planning to go to a club that night. He told me he'd call me back at my hotel room and leave a message when he knew some more about his plans.

I also called up another friend - Dan - but he didn't answer, so I left a message on his answering machine, and told him it would be best if he got in touch with Pat, since I was staying in a hotel and wasn't sure I would get his message there. Dan and Pat were good friends, so that seemed like a good solution. I told him that if he did reach Pat, we could all probably meet up somewhere that night or even earlier.

After I hung up the phone, I decided to jump in the shower. I figured I would get cleaned up quickly, and then head down to the lobby to see if I could find Madi or, if I couldn't, to wait for her there.

I went into the bathroom, and the bottle of Astroglide and the box of Fleet still sat next to the sink. Madi's clothes from yesterday still hung from the back of the bathroom door. Besides Madi, the only thing that seemed to be missing was that toy!

I finished my shower, dried my hair, and then wrapped a towel around me and was just walking out of the bathroom when I realized that Madi had returned. She was sitting on one of the two big, plush, leather, high-backed chairs by the window that had a small table sitting between them. She had on a pair of glasses - something I'd never seen her wear before - and she was reading the newspaper, drinking coffee, and eating a muffin.

Another cup of coffee and a small, brown bag sat in the middle of the table. I could tell that Madi had cleaned up and done her hair. I noticed that it was still just a little bit wet. And guess what else? She was already dressed in that lingerie I'd bought her! I don't know if it was the glasses or the lingerie or the morning light bathing her fine form, or something else, but she looked amazing - absolutely fucking great!

Then I realized what that something else might be. She had her mouth open as she was reading, which, in and of itself, was a little strange, but very sexy. I don't know why I had never noticed this before, considering that I had been around Madi now for three weeks and had seen her on five different days in that span of time, but I never realized that she had a tiny, little space between her two front teeth.

Like her birthmark, it wasn't all that noticeable, and most of the time I'd been with her was nighttime when it was pretty dark. Anyway, I suppose that could explain my having missed that particular aesthetic detail. Now, she was sitting in front of the room's big window with the light of a bright, sunny, early September morning pouring through it, and I couldn't escape the allure of it. I was beguiled by that mouth, absolutely drawn to it.

All of this is interesting considering that that was the same mouth that had so shamed me on two different occasions. But on this particular morning, I swear that tiny, little crack between those two, brilliantly white teeth made hers the sexiest mouth I think I had ever seen.

I also hadn't noticed that like her sister, Madi had a little bit of an overbite. It wasn't nearly as severe as Libby's, but I could see it now. And somehow all of these details - the space between her front teeth; the slight overbite of her top teeth; the puffy, soft, pink lips' her wet tongue which just happened to be wetting those pink pillows at that very moment; the pair of glasses; her soft, pale skin; her breasts bubbling out of that corset; the fishnet stockings; the tiny thong that barely covered her sex - it all came together in one, grand gestalt to transform her into the most glamorously, erotic girl I'd ever seen.

I stood in the doorway for a second, just taking in the sight until she noticed me, and then I asked sort of innocently, "Where have you been? When I woke up, you weren't here. I thought maybe you were mad at me."

She looked at me over the top of her reading glasses and smiled, "That's silly! Why would I be mad at you? I just went down to the lobby to get us some breakfast and the paper; that's all!"

I came over to her chair, wearing only that towel, and stood next to it. I laid my hand softly on her shoulder and smiled down at her. "You wore that to the lobby?" I was chuckling just a bit at the thought of it.

"Well", she grinned up at me devilishly, "I wore a robe over it!" She gestured to the other chair. Slung over the back of it, I saw one of the hotel's white, terrycloth bathrobes.

"Why, you little hussy!" I joked. "You're getting more and more brazen in your old age! There's no telling what you'll be up to once you turn 19!"

"Well, we won't have to wait too long for that! My birthday's later this month, you know!" She smiled again and then paused. It's amazing how much difference a day makes. I reached out my index finger, put it under her chin, and lifted her face upward toward me. Then, I leaned over and kissed her gently.

Once we broke that kiss, she smiled up at me really sweetly, but in a sort of bewildered way. I could tell she liked that kiss, but she wasn't really ready for it. That astounded me. Here she was all dressed up for sex, and she seemed surprised that seeing her like that had had the effect on me that it did. Then she asked me kind of innocently, "Would you like to join me for a cup of hot coffee and breakfast? I got blueberry-walnut muffins!"

It was awfully nice of her. I always needed coffee in the morning, and so I was grateful she'd brought me some, and the blueberry-walnut muffin was especially nice. I didn't need much to start the day, and that was perfect. But on this particular morning, there was another type of sustenance that I desired more. I was already starting to get hard.

"I would, but..." I paused. "...you know, you look unbelievable in that outfit, Madi! Really fucking hot! Hotter than the coffee, I suspect! And I love the glasses! Kind of the sexy, schoolmarmish look!" Instantly, her expression changed. Gone was the sweet, innocent, confused look I'd just seen, and in its place, I saw only desire.

"I don't think schoolmarms have the kinds of thoughts running through their heads that I do right now!" She finished her last bite of the muffin and took a sip of coffee to wash it down.

"Oh yeah! What kind of thoughts do you have running through your head, young lady?"

"Well, for starters, I'd like to know what you have growing under that towel."

"I guess an intellectually curious girl could probably find out!"

She picked up on the suggestion right away and untied the towel around my waist and let it drop to the floor behind me. My cock sprang forward and fell to about a 45° angle. It was already stiffening with a rush of blood, and she could see the excitement in my eyes and elsewhere. "Too bad you already took a shower", she said facetiously, as she reached for it. "I could have licked you clean!"

"You licking me 'clean' is the reason I needed that shower in the first place!" I said sarcastically. "On the other hand, maybe you'd like me to lick you clean!"

She gave me that wry grin again, the one that made her look about five years older than she really was, and she said sarcastically, "Oh, too bad. I'm already clean, too. Cleaner than ever, I think!" She grinned really sexily and took a big gulp of her coffee. She still had my semi-erect cock stretched out across the palm of her left hand.

"Already! You already did it?"

She shook her head, smiling with pride. "I thought you might want to get an early start. I know there's other stuff you wanna do."

"Not as much as I wanna do this!" When I said that, she rose to embrace me, and I began to pepper her neck with kisses and caress her breasts through that corset. I hadn't mentioned this to Madi, so I don't think she knew it, but the corset's bra cups connected to it with Velcro tabs and were, therefore, removable. One at a time, I reached my hand inside those cups, fondled each modest breast for a couple of seconds, and then, in a violent jerk, ripped each cup from the corset, fully exposing her creamy tits. The loud tearing sound that the corset made when I pulled the first cup from its affixed place startled her, but when I did the same thing with the second one, she just giggled.

"You're in a good mood this morning, aren't you? I think you're looking forward to this almost as much as I am!" She could have been making reference to last night and my questionable antics or to the aggressive move I'd just made, I couldn't tell which. Regardless, I decide to apologize for the previous night.

"I'm sorry about last night," I whispered as I held her around her waist - made impossibly slender by that tightly cinched corset - and continued to kiss, lick, and bite her neck. "But I want you to know I thought about this all night long, kind of imagined what it would be like. I'll be honest with you, Madi; in all my imaginings, I just couldn't have pictured how good you look right now. You're fucking beautiful!"

She was staring down at my cock as she continued to hold it in her hand, and she never even bothered to look at me when she spoke. Then, she dropped to knees on the carpeted floor, pulled the glasses from her face, set them on the table, and then said slyly, "you look pretty good yourself!" Before I could say anything, she took me in her mouth.

If last night's blowjob was like the first one that Madi performed in her friend Kerry's living room two weeks before, then this morning's blowjob was like the second one - the one in Kerry's bedroom a half an hour after the first one. Both of those times, she was setting the stage for something else later on - not trying to make me cum. Consequently, there was no deep throat, no flying saliva or semen.

Instead, this was a polite blowjob by Madi's standards, much more romantic and sensual. She ran her hands all over my abdomen and chest as she sucked me and grasped my ass cheeks as she pulled me to her so she could control the depth of my penetration. She didn't take me too deep, but instead performed a combination of licking, sucking, and stroking techniques. Whatever the approach, it did the trick, and within a minute or two, she had me rock hard.