Lesson Learned

"You sure talk a lot of shit," Ronnie chided as she took a long sip of her martini. Her eyes were deep green vessels that poured forth cool, unwavering judgment.

I was taken aback by her direct confrontation, and confused. I was a reasonably experienced date, enough that I at least knew how to be a little charming when I needed to be and very persuasive when I chose to be. But Ronnie had been combative all evening, and I was beginning to find it difficult and frustrating. I hadn't made her laugh or even chuckle. But I had made her smile, just once; it had been like a reward that I had to win more of.

Ronnie was a judge (which might explain a lot, in retrospect), 44 years old, probably five-ten (six feet with the heels) and three-eighty, though I didn't ask for hard numbers. She had advertised online as a professional woman in town on business looking for a man who could take her out while she was in town, show her a good time and "Perhaps I'll allow you to give me a foot massage, if you are smart, handsome, charming, and have strong hands", the ad had said.

The photo on her ad had stunned me. As taboo as it may sound to some, bigger, older women was my most favored sexual attraction of all. She had wondrous eyes and a cute, vivacious youth that seemed to shine forth through her, and she was slightly weathered and very rounded with age, which I of course found incredibly endearing. Her dyed-red hair was cropped short and was spiked, but its style was undoubtedly feminine, and the very red color very much became her.

Wild, unabated fantasies enthralled me as I had corresponded with her. I will admit that I was not interested in a relationship or anything of that sort. Not with Ronnie. This was pure fun, and I suspected that her ad implied that it was for her as well. Either way, I had felt compelled to make sure that I was the man she was looking for.

"Well, don't you? Can't you handle one direct question?" Ronne clanked her glass to the table firmly, and I stammered as I groped blindly for a response. She leaned forward, pressing, but her expression remained rather cold and lacked any real resentment. "You know, I'm so tired of guys like you. Mind you, you have your uses, as far as this kind of thing goes. But you think you're such predators, and that inflates your little egos even more than they already are. You think you can just do what any women what you did with the last, but you probably can't even please a woman properly." Her voice was firm and masculine but undoubtedly woman.

"Wha—?" I began, my face scrunching up involuntarily as I felt my face flush. But she pressed on.

"And for all the self-aggrandizing and machismo," she leaned back and held her hands up and out as she pointedly glanced around, "I ask to be shown a good time, and I get taken to my own hotel lounge? Classy."

I felt humiliated and a bit crestfallen that things had suddenly taken such a bad turn. Despite a physical attraction so intense it was almost painful, we obviously had had a clash of personalities, or bad timing, or whatever. Here was my chance to sound thoughtful, at least, and perhaps do some damage control. "Well, I know women like to be wined and dined, but—"

"Fuck your conjecture." She interrupted flatly, and took another sip of martini. She seemed about to put the glass down, but she paused, swigged the remaining drink down in a gulp, and began to gather her things.

"Hey, hold on. I'm sorry if this place wasn't good enough for you. You should've said something sooner. I think you are assuming at least as much about me as I am about you, here, so I don't understand why you're so angry."

"Oh, I'm not angry. I'm a judge; do you really think you could make me angry if you tried? This conversation's over, okay? And so is this 'date'. But you sure do look good, kid, so if you feel like shutting up and giving me a foot massage, I'll be upstairs. Executive suite one."

She stood and began to stride briskly toward the lobby and elevator. As she'd been sitting when I arrived to the date, I got my first real look at Ronnie's huge body up close. Although she wore an ankle-length skirt, the full shape of her impressive hips and ass were apparent as they wobbled and jiggled a tantalizing pattern at me. Thick, strong-looking calves clicked heels into the marble floor as she strode, rather elegantly and gracefully for such a big woman. Her upper arms were big around as my legs and seemed to strain the seams of her collared button-up shirt.

God damn. So perfect and I've blown my chance. As though she read my mind, or perhaps because she felt my obvious stare boring into her, she turned suddenly and yanked my stare from her body and up to her eyes. I expected her to curse at me or flip me off, but, always defying convention, Ronnie shook her head and waved an arm at me to come on.

I barely remembered to pay the tab as I fumbled after her, embarrassed.

*

I should probably just go. I have been humiliated, and I don't see anything good that can really come of this for me, I reasoned with myself at the elevator. What will we do? I'll give her a foot massage and she'll tell me to fuck off, now? But god, that ass! That huge ass and hips, and those calves in the stockings. I could imagine pulling those stockings off her calves and squeezing and sucking them and slapping them. I dreamed of taming this shrewd bitch, quite frankly. But she'll probably just string me along, I surmised.

When the light of Ronnie's elevator car finally hit the E for Executive and began its return trip, another man came to stand with me as I waited. I caught his eye and nodded curtly to him as I wiped a clammy sweat from my brow.

"She's really pissed at you, huh? That your wife?" I almost started at the question, but I held my cool and gave a shake of the head.

"No offense, but she's a little older, isn't she? How old are you, if you don't mind?"

The elevator dinged and as I fumbled for a lie, the man and I caught sight of a huge pair of black, lacey panties lying on the floor of the elevator. I felt my face go hot.

"Uh, you go on ahead. Have a good evening," the man said, stepping away.

*

I realized wholeheartedly that I was being completely and totally fucked with. There I stood, her massive panty in my pocket, one hand rapping on her suite door, the other on my hip. I was half horrified, half intrigued, half angry, half horny, and completely baffled as I stood there. My intent, at this point, was to cut my losses and get the hell out of the situation (to avoid any further humiliation, I wouldn't admit to myself), but first I had to have the last word. Even if she answered the door completely naked, if indeed she answered at all, I'd let her hear it and then leave, and I might toss the panties at her face in the process. It was an elegant plan, an appropriate forty-four stories in the making.

She opened the door promptly. She wasn't naked. But she stood with her shirt unbuttoned at her breasts and sleeves but still tucked into her skirt, as though she'd been getting undressed. Her look was cold as ever, but she had cracked a wry, crooked smile at me.

I stepped into the room, and began to spout. "So did you make this date just to fuck with me, or what? I'm through with this."

Ronnie closed the door behind me and lifted her shirt up over her head. Her huge arms and breasts wobbled heavily in the process, which I found intensely sexual, but I went on, determined to have the last word. "Wait a minute. You can't just insult me and then just expect that I'm gonna do anything for your pleasure, lady. I'm outta here." I started for the door, removing her panty from my pocket with the intent to return it.

But Ronnie blocked the door. Indeed, the width of her hips stretched nearly the entire breadth of the door; I would have to remove her physically if I wanted to leave. It was at that point that I realized how much bigger than me she was. She unbuttoned her skirt. It fell to the floor, and I stopped in place, my mouth agape. Her belly hung rested comfortably on trunk-like thighs that curved downward to stocking-covered calves that were almost as wide. The stockings were cuffed around the thickest part of her calves, accentuating the thickness of her legs further. Her round, massive tits hung heavily but snugly in her bra, which was lacy and looked expensive.

Without speaking a word, Ronnie approached me and roughly pushed me toward the bed. I staggered back and stood shocked for a minute, which was just long enough for the huge woman to barrel into me again. Her hands struck my shoulder with enough force to pitch me backward onto the bed. For a second I realized the absurdity of my situation, and I buried my face in the bed in a moment of consternation, and in order to push myself up to my knees.

But I felt Ronnie's big weight on me. She crashed into my side pinning me on my back, and before I knew it, she had pushed herself ponderously onto me, facing my legs, with her huge ass in my face.

And what an ass it was. It was huge and dimpled and sagged just a little, but the effect made it appear as though she had more junk down there. She inched backward onto me, and she took care to position her big calves onto my arms, pinning them. She remained leaning forward, though, keeping her ass up off of me, but the crushing weight of her was already making it difficult for me to breathe.

"What the fuck is this? I—" before I could finish, Ronnie sat back, and what must have been a hundred and fifty pounds of ass came smashing down into my nose and open mouth. The bulbous cheeks engulfed my face, and I could feel the squishy heat of her pussy pressed right between my eyes. She stayed there for a few seconds then leaned forward again, and I witnessed her ass rolling like an ocean as she shifted forward. I thought of kicking at her, but she supported the weight of her upper body on my thighs, her arms locked. I was pinned.

"I'm so tired of this shit," she sneered, finally showing some real annoyance. "You came here to fuck, I guess, but you had no interest in my pleasure at all, did you? Fucking hotel lounge. You see, women know."

She brought her ass down onto my face again, harder this time, and kept it there for a bit longer, until I struggled to breathe. As I began to squirm for release, I felt one of her hands on my belt. Finally, she released me, and I gasped.

"Women know when you just don't give a shit. You may have found that most are willing to play your stupid little kid games with you, and you may actually be convinced that they don't know that you're a conniving asshole that doesn't give two shits about them." She stuffed her colossal ass down onto my nose as she made her points. "But we know. Mostly women put up with it because they get lonely as they keep looking for someone who's not a complete asshole and who might give two shits about how they feel or if they get pleasure from being with them at all. I think you should feel what it's like to get fucked and be left unsatisfied."

She smashed her ass down on me once more, with all her weight, this time, and she lifted her hands off of my legs and rested them on her dimply thighs. Her entire weight was focused on my face now, and I couldn't breathe at all. Twist and kick as I might, I couldn't dislodge myself. My head began to pound. When my body registered alarm at the thought of suffocating, it involuntarily jerked forward with all the strength in me, but to no avail. Ronnie only leaned forward and said, "Don't you get it yet? Lick. Lick and I'll let you breathe, so I can show you, asshole." She smashed her pussy down onto me again.

I didn't lick. In fact, I was near panicked. It took two more near-suffocating face-sits for me to compose myself enough to begin to lick the already sopping wet and boiling hot pussy in my face. Her lips and fat inner thighs fully ensconced my cheeks, and before long I was feeling chafed, sweaty, and rather beat up. Ronnie sat back and grinded into me, hurting my nose, but allowing me to breathe if I tried hard enough. I had not even noticed that she had finished undoing my belt and pants had pulled my cock out and began to stroke it.

As my licking began to take effect and I could sense that she might be close to cumming, Ronnie would pull her ass up into the air and shake it, moaning slightly but always maintaining control, her fat shaking all around. I realized that my head was pointed directly toward a mirror, and when she lifted herself off me this way, I could look up to see the massive ass reigning above me, wobbling and clinching in ecstasy.

She must have repeated the process for an hour, bringing me to the verge of suffocation beneath that magnificent ass while she brought herself just short of cumming time and again. Her exclamations grew louder each time she raised her ass off my face, and I could see her pussy gripping and spasming, teased to the verge, frothing wet and creamy.

I hadn't even noticed that she'd loosed my cock from my pants until I suddenly felt her soft, quick strokes on it. She didn't please me with her mouth, though I wanted it so badly; it wasn't before I was hard as rock.

"At least you're good at that," she remarked as I licked. "It's probably better than a cock shoved in your throat, don't you think? Is that what you wanted to do to me tonight? Men think we get something from that. We don't. So lick more, asshole, and you can see how it feels for someone to not give a fuck." At that, she scooted herself forward just an inch, and when she pressed herself down onto my face this time, her asshole was directly on my tongue. I licked and darted my tongue in and out, working to earn the privilege of a breath.

But this time, my breath didn't come. Her asshole pressed down harder and harder onto me, and I felt myself becoming a bit light-headed as the heat and lack of oxygen began to take its toll. My nose must have been inside her asshole now, so forceful was her weight on it.

I realized that she had spit on her hand and was wetting my cock, and I gasped gratefully when she lifted herself off of my completely. I lay red and breathing heavily, getting my composure as I looked up at her. She towered above me, standing at my feet, and for a moment I stood appalled by the savage look on her face. She was flushed deep red, obviously relishing in taking her pleasure. I felt a relief that it was over.

But Ronnie grabbed my ankles, one in each hand, lifted them, and dragged me toward her. I slid on the bed, and she stepped forward over me, her column-like thighs over the backs of my knees, my feet in the air and her giant bulk between my legs.

There she held me for a second, looking down at me, her face vicious. I was still woozy from lack of oxygen, but I understood her when she said, "Now you can see what it's like to get fucked like a girl."

She grabbed my cock, which was still throbbing hard, at the base, pulled it down and between my legs till it hurt a little, and squatted down on it, finding her pussy with ease. We cried together in pleasure as her wetness squeezed down the entire length of my erection. I could feel the tip grinding into just the right spot—for her.

And so she had me, on my back, bent almost in half with my knees against my face, and she bounced her huge pelvis down onto my cock, her ass driving all the weight of her onto my shaft with each thrust. The bed yielded along with us, facilitating her fucking me, easing the ride a little. She fucked me hard, as a strong man would, and the slapping sound of her ass on mine must have been heard throughout the entire floor of the hotel. She kept a consistent rhythm that had me feeling the approach of a serious orgasm within four spanking strokes.

When I could, I looked down to see my cock slamming in and out of her—or was it the other way around. I felt completely emasculated.

"Ooo! Ooo! Ooo!" Ronnie cried with each bounce, and I could feel her pussy begin to grip me, tightly. I felt a pervasive, constant pleasure deep inside me, and I felt my orgasm coming on strong. Just a few more strokes--

But Ronnie suddenly stood, braced herself on the wall with one hand, and coaxed an intense, bursting orgasm from her clit with the other. Her pussy loosed a wet splatter at me as she came, and then the remains of her squirt showered me in a hot rain as it dripped from her inner thighs. Her giant pelvis shifted and bucked above me, sending her fat wiggling and jiggling.

"Aaah-hah-haah!" Ronnie exclaimed. She continued to bounce her ass and thighs as she exhaled sharply, catching her breath, still cumming. Then he stood fully upright and ran her hands through her hair. "Now that's how you fuck, boy," she exhaled breathlessly.

The sight of her dripping and flushed above me was more than enough to make me want to get my satisfaction. I began to stroke myself, staring up at her, taking her all in. But she dropped down on top of me, stopping me.

"No way," she said firmly.

"What? That was amazing, I—"

"Put your clothes on."

I sat dumbfounded for a moment as my erection subsided. I looked at her for a long while, and she returned my gaze unflinchingly. I tried to insert some kind of sentiment into that look, some innocent confusion, but as she had all evening, she rejected that sentiment as false. And she was right, of course.

When I finally did stand, she retreated to the bathroom and turned on the shower. I lingered for a moment after dressing myself, considering some kind of peace offering and just wondering what in the world to do with myself. I'd never been quite so frustrated in my life, and I wanted so badly for Ronnie to give me some kind of chance to alleviate that. But her head appeared from the bathroom door, and her look was stern as ever, her eyebrows raised.

"You can goooo nooow," she sang in a bitter tone.

I never saw her again, and I certainly never told anyone of our encounter, but I'll never forget the amazing lesson she taught me, and with so few words.