I Wish She Hadn't Ch. 02

"Take the toy out first and use a lot of lube, okay? Then, I think you should just touch me there, and after I get used to that, put the toy back in and try moving it back and forth a little bit, so that I get used to you moving inside me. Oh, and go slowly until I get used to it."

"What position?"

"I'm not sure, but the lady says she likes to lie on her back with a pillow under her butt."

"Okay. Lie back and I'll help you." Madi positioned herself on her back, in the middle of the bed, and I slid one of the pillows under her lower back so that her ass was sticking straight up in the air. She spread her long, slender stems apart and then held them behind her knees so that her stocking clad legs stuck straight up into the air. I crawled between them and positioned myself on my stomach, propped up on my elbows so that my workspace was directly in front of my face and hands. Then I reached for the lube on the nightstand and set it down next to me on the mattress.

I started by withdrawing the toy from inside her. I hadn't really taken a very good look at it before - at least not up close and personal like this - so I didn't really know exactly what it looked like and how it was supposed to work. When I started pulling on it slowly, there was a sudden, little pop, and the first and largest of these kinds of ball-shaped pieces of glass slid out of her rectum. A soft little groan escaped from Madi's throat.

"You okay?" I asked.

"Yes, that's the biggest one. Each one after this is a little easier to handle." I pulled again, and as she'd described, another smaller ball popped through her anal opening. I could see now how the thing was constructed. Each ball became progressively smaller so that the whole thing tapered downward toward the tip. I had thought of the thing as a plug, but it was really more like an anal dildo instead.

In between each ball, the glass narrowed so that the sphincter muscle would close around that narrower part of the shaft every time you pulled another ball out or pushed another one in. After each one popped out, I could see more of the lube's slick sheen on the glass. After the third ball popped through the opening, the last two slid out rather easily. I set the thing down on the nightstand on a washcloth Madi had conveniently left there.

I grabbed the bottle of Astroglide, squeezed just a tiny drop onto my index finger, and then, very carefully and gently, I started rubbing just the tip of my finger in small clockwise circles around her anus. I kept going, expanding and then contracting the circumference of the circles.

"Oh, that's nice! That feels really good, John. You're good at this."

I don't know whether or not that was true, but it encouraged me to try something different. While I continued rubbing in circles around her tight little backdoor, I went down on Madi's pussy. I alternated between long vertical licks up and down her pussy lips, and kisses and gentle sucking applied to her clitoral area. "Ooh god, that's good", she purred.

The verbal feedback was helpful, but there were other clues that told me what worked well and what didn't. When I hit a particularly pleasurable spot, Madi would experience one of these delightful, little contractions, and I could feel them most acutely when my finger was either directly on or, later, inside of her asshole. When those quick, little momentary spasms happened, I knew my labors were appreciated, and I was rewarded with more of her soft, erotic moans and groans.

And then after five minutes or so of light manual touching combined with my oral play, I sensed that she was ready for some penetration. "I'm going to use my finger to enter you now, Madi. Tell me if this hurts at all, and, if so, I'll stop." Madi took a deep breath as I added a little more lube to my finger. And then, just as I penetrated her tight chute, she let the breath escape. I didn't enter very deeply, just a half inch or so, and withdrew almost immediately.

"Yeah, that's nice. Keep going", she sighed. So, having tried it once slowly, I entered again, then quickly withdrew and reinserted again. She seemed fine with it, so I kept going - in and out again and again and again, still not very deeply and still with only the tip of my index finger. Madi had to calibrate her breathing to accommodate my rhythm, but now I could tell she was beginning to get used to it.

It was time to increase the penetration. The next time, I added more lube to the same finger and inserted it just a bit more deeply. I tried to leave as much Astroglide as possible inside her, so I withdrew very slowly. Now, it was for a bigger test. "I'm going to use two fingers now, Madi, I'm not going to go too deeply, but it's going to stretch you a little more."

"Okay, just tell me when."

I squirted a little more lube onto both my index and middle finger, and then I poised them at that slick and greasy opening. "You ready?"

"Yes." She took a deep breath.

I went in again, this time about an inch or so, still shy of the main joints of my fingers, and as I did, Madi let out her breath, along with a satisfied whimper, "Ooohhh, fuck yeah!"

"Okay, I'm going to keep going now." She didn't say anything, but she shook her head affirmatively, so I placed my middle finger at ground zero, the slick tissue of that pink starfish, and I began sawing those two fingers in and out, slowly at first, until I was able to build a rhythm. Madi began matching her breathing to my rhythmic intrusions, and I was slipping and sliding without resistance for probably around 30 seconds or so.

It seemed to me that there was one more natural step along this gradual accretion before we moved on to the real thing - the toy. If Madi could handle me moving that glass thing back and forth inside her, I figured she could probably handle my dick. "Okay, Madi. I'm gonna use the toy on you now. Let me know when you're ready."

I reached for the glass plug on the nightstand, squirted a steady stream of Astroglide on it, especially near the tip, then ran my hand back and forth it to spread the lube out evenly. Then, I placed it at her pleasure center and announced my intention, "You ready?"

Again, she took a deep breath, shook her head, though a little more timidly this time. I pushed in with one steady motion, while Madi let out her breath slowly. Then, once all five balls had disappeared, I reversed direction and withdrew each in turn. There was a tiny little popping sound, especially when the first two balls reappeared at the entrance to her ass.

"Jesus Christ!"

"You okay?" I inquired.

"Yes, oh it's fucking good. Keep going!"

So I did. I pushed in again, and then, once fully in, immediately changed directions. Then, I repeated the process... again and again and again. She was breathing in rhythm now, and moaning softly, "... ahh, ahh, ahh ...uhm, uhm ...sss, sss, sss ...ooh, ooh ...sss, sss, sss ...ahh, ahh... oh, oh, oh..." Madi was in a zone now, kind of oblivious to everything but her pleasure. So with that in mind, I thought I would revisit her kitty with my mouth.

When my tongue started dancing around her clitoris, the moaning became louder, and she commenced her own improvised mantra, chanting in rhythm, "oh yeah, oh yeah, oh yeah, oh yeah!" And then as I got more aggressive with my tongue, the language became bawdier and her voice more vociferous... "oh my clit, oh that's it, that's it, lick that clit... Aaahhh! Uuuhh! Aaahhh! Uuuhhh! Mmmmmm! Mmmmmm! Mmmmmm! Sss, sss, sss... Aaahhh! Ooohhh, fuck! Mmmmmm! Mmmmmm! Sss, sss, sss, Aaahhh! Oh yeah! Oh yeah! Oh yeah! Aw fuck!" and on and on.

And then her legs started shaking, and I knew she was starting to lose muscle control. It was pretty clear that, if I continued, Madi would soon reach the mountaintop, and we both knew what that might mean. But I didn't want her to cum - at least, not that way. She was ready now, and watching her passion grow, so was I. So, oblivious or not, I announced my intentions, "Okay, Madi. You're ready for me now. I'm going to pull the toy out, and very, very slowly I'm going to enter you, okay? Just my head at first, and then when you're ready for it, I'll give you more."

She didn't answer, but I knew she heard me, because when I first pulled my mouth away from her pussy, and then again when I withdrew the glass plug from her ass, I saw a look of disappointment cross her face, and then her eyes opened and she stared up at me in disbelief as I knelt between her legs.

Working that toy in her ass and simultaneously licking her clit with my tongue had given me an idea. It was the two-pronged approach that worked the best. I figured the more preoccupied she was with the sensations produced by her little man in the boat, the more distracted she would be from any pain inflicted by my cock on her ass. Since my cock and my mouth couldn't be maneuvered to within an inch and a half of each other, there was only one other solution. "Okay, Madi, I want you to start touching your clit. I'm going to enter you as soon as we're both lubed up. I'm gonna start with you, okay."

She shook her head, and began to gently finger herself, and as she did, I applied a generous dollop of lube to two of my fingers, and placed them at her sensitive opening. Then, I pushed inside and turned my fingers as far as I could before withdrawing them so as to leave as much of it inside her as possible. Then, I applied the same amount of Astroglide to my cock, and stroked myself several times. Interestingly, without any stimulation for the past 15 minutes or so, I was rock hard. I was nearly as excited as Madi.

When I was good and slick, I grasped myself around my root and placed the meatus on the tip of my bulbous head directly on the center of her anal opening. "Okay, are you ready? I'm gonna put the head in now."

"Yeah, do it; do it." She was already going to town on her clit, so I pushed. Her sphincter resisted at first, and I have to admit, what with all the lube on both of us, my target slipped elusively away a couple of times. But I kept pushing and then, suddenly, I popped through, and the moment I did, Madi unleashed a tortured cry, "Oh fuck! Fuck, it's big! It's so fucking big!"

"Are you okay? Do you want me to pull out?"

"No, no, no!" She kind of grimaced as she spoke, "It's just a lot bigger than that toy, but it's good. It's good. I just have to get used to it." Then, she must have reminded herself to breathe, because she instantly took in a lungful of air, and when she started to expel it, she said, "Okay. I'm ready. Give me more!"

I pushed in again, gaining only an inch or so, but that's the point where my cock starts to get pretty thick. "Jesus, fuck! Holy shit! You're fucking huge. I think you're going to rip me in two."

"Okay, okay! I'll pull out!" It felt fucking amazing - so different than her pussy - much, much tighter, but I sure as hell didn't want to hurt her. I figured I'd already done that enough times.

"No! No! No! Don't! Don't! Don't pull out!" She started breathing again really deeply - taking in big gulps of air, and slowly letting them out.

It struck me at that moment that while my job was pretty damn easy and kind of intuitive, hers was a lot more complicated. Madi had to multi-task: hold her legs in place, monitor her breathing, continue to finger her pussy and clitoris, and gauge the depth of my penetrations, all while trying to relax her muscles, which already seemed to have a mind of their own.

I knelt there stock-still for a moment and waited for her. "Oh! Oohh! O...kay! Give me a little more!"

I pushed in and moved myself another inch and a half into her. I hadn't intended to go so far, but her anal canal was so slick now, and I just slid. Madi's mouth fell open, and her head tilted back, and she grabbed her legs as if to pull them back even further, "Oohh fuck! Jesus fucking Christ! Is that all of it?"

I looked down at my rock hard erection. By the looks of things, I wasn't even half way in, but, truth be told, the thickest part of my cock was now wedged in her sphincter. Though there was a good three or four inches to go, her rectum wasn't going to be stretched any more than it was at that very moment.

I figured I would try to help as best I could, so I leaned forward, spread my hands out wide onto the mattress in front of me to support the weight of my body, and, in so doing, pinned Madi's legs against my upper arms so she didn't have to hold them up. This changed the angle a little bit and improved my leverage. Then, I answered her question.

"No. I'm not even half way in. Maybe I should stop."

"No!" It was but a single word, but it was shrieked with defiance at the top her lungs. Again, I froze. After 20 or 30 seconds more of deep breathing, she spoke again, "Keep going."

I am nothing if not a cooperative man, even, generally speaking, an obedient man, so I did as I was told. I pushed again and this time, I slid in a good two or three more inches before I stopped to gauge Madi's reaction. It was what I expected, visceral and vocal, "ahh, ahh, ahh... uhm, uhm... sss, sss, sss... ooh, ooh... sss, sss, sss, sss... ahh, ah..., oh, oh, oh..." I was nearly in to the hilt now, and only my root, perhaps an inch or so of my cock, was visible. But Madi was determined, and she had one more command for me that morning, "Start moving... start fucking me", she growled.

"Are you sure? Are you sure you're okay?"

"Just start fucking me!" There was no affection in her voice anymore, just insistence.

So, that's what I did. I started moving, back and forth, relatively slowly at first, but gradually building a steady rhythm. And just as I was afraid of, once I did, I didn't want to stop. It felt too good. The whole time her ass was just squeezing my cock, squeezing it tighter than it had ever been squeezed before, and nothing I had ever experienced sexually could compare to that feeling.

Still, if it felt good to me, it's impossible for me to convey how good it must have felt to Madi, and her vocal reaction evidenced an enthusiasm that couldn't be contained, "oh, oh, oh... mmmm... aahh... uh, uh... oohh, oohh... oh fuck! Aaahhh! Aaahhh! Fuck... yes, yes, yes, yes, yes, yes, yes... aaahhh, aaahhh... mmmmm, mmmmm... ah, ah, ah, ah, ah... Aaahhh! Aaaahhhh! Ooooohhhhh yeah! Aaahhh! Fuck! Oh, yes! Oh yes! Oh yes! Oh yes! Oh yes!"

I looked down to see her craning forward with her upper body, eyes closed, mouth open, and the fingers of her right hand flying back and forth over her clitoris like some winged bird of prey in resolute flight. She didn't seem as if she had any control over the tremors that those agitated fingers and my fat pecker were inducing. Pulsing quivers rippled across her shapely hips and down her slender legs.

And then she was cumming again, powerfully, "Jesus, fuck! Oh my... oh my god... cum... fuck! Cum... cumming! Aaahhh! Aaaahhhh! Aaaaahhhhh! Fuck... I'm cumming!" She must have squirted, though, I'm guessing, not as much as the night before. I couldn't really see - Madi's hand must have been blocking the spray. All I know is that I felt something warm and wet, and soon I was sliding even more effortlessly than I was earlier.

And that must have done the trick for me. Within a half-minute of Madi's climax, I was depositing rope after rope of ejaculate deep into her ass and grunting my own pointless warning, "Fuck, I'm cumming in your ass, baby! Oh, I'm fucking cumming! Uuuggghhh! Uuuggghhh! Uuuggghhh! Uuuggghhh!"

When I was done shooting, I was spent, and I wanted to collapse on top of her, but that would probably have pushed me in even deeper and hurt her, so I leaned back, putting my weight back on my knees and releasing my leverage over her legs, and then I reached down to withdraw myself from Madi's clutches. My greasy cock popped free. Then, I fell to the mattress next to her, resting on my side, waiting.

She still had her eyes closed and her mouth wide open, and she was still breathing really deeply. She wasn't ready to talk just yet, and so, without any verbal reaction, I couldn't tell whether she was feeling pain or pleasure or both.

Finally, her breathing slowed, and she opened her eyes and smiled at me. Then, she leaned in for a prolonged kiss. I had to wait a minute or two for her to speak. Finally, she did. "My god, that was intense! I didn't think I could do it, John! I didn't think I could handle it, but once you started moving - my god, it was so good! I loved it! I want to do it again, whenever you're ready! Did you like it? Did you like it, baby?" She put her arms around my neck and kissed me again.

"I sure did! I loved it! You are so tight down there, Madi! And because you are, I can't really last very long inside you like that, but I'm not sure that matters too much! It didn't take either one of us very long, did it?"

"No, it didn't!"

We talked like that for a good half an hour, both of us kind of marveling at the intensity of the experience, and by the time I was able to get it up again, we did it once more doggie style, and then with Madi on top of me facing away, while we both watched ourselves in the mirror beside the bed. Each of us came in both positions.

We had a little cleaning up to do, which took us a little while, so we didn't get out of that hotel room until well after noon that day. But there was no debate, we were both pleasantly astonished at how well our first foray into anal sex had gone. Madi said she was already addicted to it!

We hit the streets again, and a few minutes later, we stopped in a little sandwich shop right around the corner from the hotel and had lunch, and then I found a phone booth, and I called Pat up again. He and Dan had talked, and, along with Abby and Dan's wife Jan - they agreed to meet us at First Avenue that night.

We had some time to kill, so we walked back down around Loring Park and then over to the Walker Art Center, arguably the most important art museum in town. I didn't know if Madi gave a shit about art, but I thought she might get a kick out of seeing some of the modern stuff in the collection there - some Roy Lichtenstein, Chuck Close, Edward Hopper, and Andy Warhol. After we left the Walker, we walked around the sculpture garden outside, which also has a number of interesting pieces. Madi really liked "Spoonbridge and Cherry."

On our way back downtown, we strolled through Loring Park again and smoked a couple of joints. That inspired the munchies, so we stopped into a little pizzeria and grabbed a couple of slices each, before we headed over to First Avenue about the time it was starting to get dark.

There were two good bands playing - a New York countrified pop group, named Beat Rodeo that was led by a Minneapolis guy, Steve Almaas, who was kind of a legend around town, having played in the seminal Twin Cities punk band Suicide Commandos during the late 70s. I owned an EP by Beat Rodeo that I liked a lot.

The second band I'd never heard of. It was a local outfit, a country act called The Jayhawks. They had just recently formed, but the buzz about town was really positive, and they would go on to become quite influential, as one of the leading progenitors of alternative country music in the 90s and beyond. The singer/songwriter Mark Olson had penned some great tunes, and the guitar player Gary Louris was really talented.

We had a great time. I loved both bands, and Madi seemed to get along quite well with Pat, Abby, and Dan, and we all tolerated Jan, even though part of the time, she was pretty damn moody. We ended up closing the place, and considering that we didn't have to drive anywhere and only had about three blocks to walk, both Madi and I got really fucking drunk.