Mrs. Ruby

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This story took place half a lifetime ago, when I was just 18 years old and a senior in high school. I won’t generalize about adolescents and their susceptibility to peer pressure; I’m sure there are some strong independent thinkers in the high school age bracket–but I sure wasn’t one of them. I never had the courage to admit to my tastes and preferences whenever there was a strong consensus among my friends that I did not share.

This applied to music, movies, television–you name it. It was okay to differ about who was a better rapper or rock musician, but don’t let anyone catch you enjoying a country song, not even a little. If you did you had to keep it to yourself, a private “guilty pleasure,” lest you risk enduring the ridicule of the crowd. It wasn’t until I was well into my adult years that I gained the courage to own up to my unpopular tastes.

As a teenager, one of my guiltiest pleasures of all was fat girls. It may be that I’ve simply m.atured, or it may be that the cultural zeitgeist has shifted toward greater acceptance of different body types since I was a kid, but all I know for sure is that not a single one of my male friends in school ever admitted to finding bigger girls attractive in general. I am sure some of them were sincere about their tastes, though probably conditioned by the self-appointed aesthetes of our society who choose the (in my opinion, disgustingly emaciated) cover models for fashion magazines. But I suspect others were like me–secretly admiring the big girls but cowed into silence by the fear of ridicule.

Being a secret fat admirer as a teenager had its pros and cons. The disadvantages are probably pretty obvious. The popular culture seemed almost never to cater to my tastes. Not being much for skinny chicks there was precious little wankable material out there in general circulation: from Playboy to the Victoria’s Secret catalogue to the Sears catalogue, there seemed to be an anti-fat conspiracy; I was forced to use my imagination more than most.

On the other hand, there were some plusses to digging the plus-sized. Because it was rather unexpected at the time, a person could actually more easily “get away with” checking out a big girl. It was as if all the skinny chicks were constantly policing the available views of their T&A, and woe betide he who got busted scoping bustage. “Why’nch you take a picture, perve, it’ll last longer!” But with the bigger girls, I found that I could sometimes feign a detached, spacey gaze into the middle distance when, in reality, I was positively memorizing a bit of cleavage or a visible panty line for later use. Where skinny chicks were taken in stolen glances, with bigger girls it was sometimes possible to literally stare.

One example was Mrs. Ruby (not her real name) who taught my senior algebra class. To this day, even with an adult’s experience and hindsight (and even in light of the story I’m about to tell) it is hard to imagine that she knew how hard she was making me. Day after day I would have to choose a time, usually about ten minutes before the bell, to stop checking her out and just stare at my desk taking deep breaths and willing my hard-on to fade so that I’d be able to stand up from my desk after class without embarrassment.

Was she doing it on purpose? Hard to tell. Most of the guys in class either didn’t find her attractive or, like me, didn’t admit to it. If they got a bad grade or caught detention they would complain about “that fat bitch.” But to me she was a goddess–size 20, with big f-cup boobs that could squeeze together and suggest cleavage even with a neckline in full compliance with the school’s teacher dress code. She had a nice round belly and an ass that must have measured 60 inches.

And when she would help a student with a problem she was always bending over to look at their work. Sometimes she would stand in front of the desk, bending over and viewing their work upside down, giving me a glimpse of cleavage and, if I was lucky, a bit of brassiere. Other times she would bend over to look over a student’s shoulder, giving me a chance to study that ponderous ass and, hopefully, visible panty line. And of course sometimes she would be at my desk, bending to help me–too close to get a visual, but intoxicating me with the mingling aroma of cosmetics and pheromone.

She was white, fortyish, possibly Jewish, and had beautiful, lustrous, long, straight black hair that shone like the kind you see in a shampoo commercial. Almost daily she wore bright nail polish and lipstick, fire-engine red or some other loud color. Her eyes were a shimmering black, like oiled, burnished ebony. She was always extremely well put together, with designer clothes that, only in retrospect, it occurs to me to wonder how she could afford on a teacher’s salary.

I had a ritual with her. Apart from the random, sporadic occasions when we were working in class and I could steal random glances acıbadem escort as she bent to help this or that student, there was an almost daily activity where she would, on request, work out a problem on the board from the previous day’s homework. If no one else presented an appropriate one, I would pick out a long, complicated word problem and ask her to work it out on the board. This would make her turn her back to the class for a prolonged period and, if the problem took enough board space, eventually compel her to bend pretty low in order to finish it.

The best part was that the ploy was never implausible because the word problems were naturally the most difficult and most likely to require explanation. I would just sit there and gape at her enormous ass, salivating, heart pounding, cock throbbing. It was amazing. The only hard part (pun intended) was that this activity was usually close to the end of class and it would sometimes bump up against my ten-minute rule. But life is all about hard choices, and this ritual was quite worth the risk.

Then one day she caught me.

She had brought in a variety of circular objects of differing circumferences to demonstrate the discovery of pi. We all knew about pi from middle school, but she wanted us to discover it in the way our ancient Greek forbears must have done as a property of things circular, so she split us up in groups with tape measures and a Frisbee, coaster, coffee saucer, chrome hubcap, etc. One by one each group sent a representative to the board where they would prop their group’s circular object on the chalk tray and demonstrate their results.

Then in the last quarter of class she erased the pi calculations and offered to do her usual demonstration of last night’s homework. As usual, I picked a nice long one from the word problems section and raised my hand.

At first it worked the way it always had. Her lilting voice mingled with the squeaky staccato scrape of her chalk as she explained the steps in the solution, supplying a sort of warm soundtrack to this lovely dance as she worked further and further down the board until she was bent at a nearly perfect right angle. “Uh huh,” I would say from time to time, pretending to listen, “mm-hmm,” all the while staring at that giant ass, imagining myself coming up behind her, hiking up her skirt and yanking down her panties, thrusting inside of her, and feeling her big jiggly white ass slap rhythmically against my belly, moaning as I deposited every last drop of my virginity into her warm pink goodness.

That day I was particularly fixated: she had on a particularly flattering ecru blouse and khaki skirt. I was staring, staring, staring, completely lost in that luscious rump, when I vaguely detected something had changed. What was it? In my daydreamy state I couldn’t be sure. Then I realized what it was. The room had fallen silent–the sound of her chalk and her New Jersey vocal cadence had both ceased, but I hadn’t noticed (I could have used one of those canned record-scratch effects you get on TV shows). I heard her say, in the distinct tone of someone who is repeating herself, “Mr. Waylon (not my real name), are you still with us?”

Then I realized what was happening. She was still bent over, back to the class, but I suddenly found myself making eye contact with her in the reflection of the chrome hubcap still propped on the chalk tray from the pi exercise! There was no disguising what had just happened. I was staring hard at her big butt and she had caught me in flagrante. I could feel my face rapidly reddening, wondering if it was as obvious to the other students as it now was to Mrs. Ruby.

“Mr. Waylon?”


“Are you chewing gum, Mr. Waylon?”

Huh? What the hell kind of non sequitur question was that? Of course I was chewing gum! I always chewed gum in her class (her class was my last of the day, after lunch, and I self-consciously wanted my breath to be minty fresh if she ever came to my desk to help me with a problem). She had never mentioned it before. “Um,” I stammered, a bit confused, “yes,” I finally said, “yes I am.”

She rose and faced me. “You do know it’s against the rules to chew gum in class, don’t you, Mr. Waylon.” I was literally stunned silent; I just stared at her stupidly without replying. She strode up to my desk, extended a supine hand in front of my face and, with a snap of her fingers, said “give it to me.”

This only added to my shock. “In your hand?!” I was incredulous.

“Spit it out, now, Mr. Waylon. And remain after the bell. You have detention.” I took the gum out of my mouth and diffidently placed it into her palm. Pardon the hackneyed phrase but as she proceeded to drop my gum in the trashcan I understood what people mean when they say you could have heard a pin drop in the room.

Just then I realized what was happening–or akbatı escort at least I thought I did. She had busted me checking her out and wanted to punish me, wanted me to have detention for it, but didn’t want to embarrass me by announcing the real reason to the class. She used the gum as a pretext for my own good.

Same with spitting the gum into her hand. Her calling me out had caused my hitherto massive hard-on to list to starboard a bit but, even so, I was in no shape to stand up and put my gum in the trash. She must have known that, which is why she came to me–to spare me the embarrassment. In that moment, even though I’d caught detention, I suddenly felt grateful to her. Then I cracked a smile as I caught myself thinking: “Her heart is as big as her ass.”

Algebra was my last class of the day so reporting for detention just meant remaining in class past the bell. “Mr. Waylon, could you come here please,” she said, motioning for me to come to the front of the now empty room. She handed me a thick red accordion file and said “These are the ungraded midterms from all five of my classes. I want you to sort them into alphabetical order by student last name, keeping them in their separate periods. That should be about a half-hour’s work. If you finish early you can leave early, but if you’re still here in 30 minutes you can leave whether you’re done or not. Use my desk.” With that, she disappeared into the hall and left me alone at her desk.

She had the standard issue teacher’s desk, putty-colored aluminum with chrome legs and handles and a simulated woodgrain top. Her office chair was a lime-green swivel job on casters, scratchy polyester fabric except for the armrests, which were sticky vinyl. The whole desk was shoved into a corner, directly abutting the thickly painted cinderblock walls, leaving plenty of the front of the classroom as a stage for her daily blackboard demonstrations. I sank into her springy office chair and briefly surveyed the landscape from this perspective.

On a corner of her desk, facing her chair stood a framed Olan Mills, she with her skinny husband and skinny ten-year-old son in their best clothes, smiling out at me. Mr. Ruby looked like a lawyer in his blue suit and curly but closely cropped salt-and-pepper hair. “So that’s the guy who gets to fuck Mrs. Ruby,” I thought. The son had his father’s hair but it was allowed to roam free in a tousled unruly fro. I sat there for a moment taking in The Ruby Family and then began alphabetizing her first-hour class’s tests.

After maybe five minutes she returned to the room and came directly to her desk. “Could you excuse me a moment–I just need to get a few things out of this file drawer.” She was referring to bottom drawer of her desk and, before I could even offer to get up, she pulled out the drawer and began fingering the manila tab tops. I rolled my chair as far back into the corner as I could but there was no hiding from it; her enormous khaki-clad derriere was no more than twelve inches from my face, closer than I’d ever been before.

Almost immediately I started swelling in my pants as my head filled with visions of reaching my hands up under the material, tracing the curve of her thick milky thighs, locating the elastic of her giant panties, sliding them down over her massive roundness. I imagined my face lowering into the valley of her buttocks, I imagined locating that warm tangy gash in a trim forest of black hair and–I was virgin–I could only imagine the taste!

This went on for a surprisingly long time, two or three minutes at least, as she shifted her weight from foot to foot causing her big pear bottom to shift in an enchanting waggle. From time to time she would pull a file out and set it on her desk but at the time it did not occur to me how improbably protracted her search had been, as though she were just randomly thumbing the files. I recall thinking with my big throbbing hard-on: “Doesn’t she know what she’s doing to me?! Maybe it was the gum after all.”

Finally, after what seemed like several minutes, she said “This is taking longer than I thought.” I started to offer to get up but she cut me off: “How about I just sit in your lap for a minute.”

“Um, I, uh–”

“Won’t be much longer.” Whereupon she lowered her big beautiful warm bottom onto my thighs. I couldn’t believe it. I was holding perfectly still. My fingers were in a white-knuckled death grip on the arms of the chair and I was staring at where my knees disappeared under the soft globe of khaki. My heart was pounding and my breath deepening. I was so nervous that I actually started to lose my hard-on, if you can believe that. But that wouldn’t last long.

I began mentally revising my theory. “Aha!” I thought, “She does know what she’s doing to me: this is part of the punishment.”

But then, with the only warning a hastily aksaray escort uttered statement “I just need to get into the back files here,” she abruptly pulled the file drawer all the way out and simultaneously thrust her fat bottom all the way back into my belly, pinning me to the wall with her girth. It was too sudden and there was nowhere to hide. I tried with all my might to squeeze backward into the chair but it was no good: What was left of my hard-on was poking conspicuously into her right butt cheek.

She froze instantly on contact. For a moment she held completely still, but then began shifting her bottom in a side-to-side motion as if to be certain of what she had detected. Then, in a wry, knowing tone, she said: “So, Mr. Waylon, I see someone has been paying attention in class.”


Without another word she began thrusting her bottom back and forth, back and forth, grinding against my cock which, needless to say, was now once again hard as a rock. In response, and without even thinking, I started meeting her rhythm with a forward pelvic thrust of my own. She picked up the pace and the springs of the office chair began squeaking in time with the bouncing rhythm of the ride.

The sensation of my hard cock digging into the crack of her khakied ass was at once ecstatic and unbearable. Before I knew it I was arching my back in a pounding upward thrust trying desperately to press harder into that big beautiful rump. Then she reached back and took my hands from where they were still gripping the armrests and she placed them on her body, where the curve of her hips rounded into her big booty. I immediately accepted the cue and reached forward, fondling her love handles, her belly, even trying to reach her breasts before moving back down to her pelvis.

I began putting her love handles to their intended use, pulling her hard against me as I thrust harder and faster against her soft jiggling backside. She put her palms flat on the desk, feet on the floor, and changed her stroke, began lifting her ass into the air and slapping it down hard against me.

By now it occurred to me what was going to happen, and how inconvenient it would be to deal with it here at school, and I thought about trying to stop it. For the first time I stopped staring at her ass, closed my eyes and tipped my head back to clear my mind. When I lowered my head to the side and opened my eyes I found myself face to face with that paragon of familial bliss, The Ruby Family. I looked at the father, then the son. I thought: “I’m dry-humping your mom, kid.”

And suddenly there was no way to stop–I was past the point of no return. I was thrusting hard and fast, pulling her toward me and pressing the whole length of my shaft–as much of it as I could through my jeans–into the place between her buttocks when, seized with that telltale tingle of inevitability, I froze, shuddered, and felt my whole body start to seize up. She easily detected what was happening and momentarily pulled away from my grasping urgency. “You making a mess in your pants sweetheart?” she asked as, to my amazement, she quickly and deftly pulled up her skirt exposing acres of cottony yellow panty, and ground herself heavily down into me just in time to meet my last desperate thrust.

My buttocks tightened into an impossible pucker as I pushed forward involuntarily and, gasping, felt shockwaves of pleasure rippling through my body as generous spurts of hot semen began coursing into my underpants. I felt I’d had the wind knocked out of me. She was still pressing hard against my sputtering member until the last contractions finally faded and, when she rose, just before she let her skirt slip back down to cover the evidence, I could see where my load had soaked through my jeans and left a spot on her lemon-colored underwear.

She stood and wheeled her massive body around, gazing down at my spent form with a satisfied smirk. “You seem to have had a bit of an accident, Mr. Waylon. In light of your problem I think it’s appropriate to dismiss you from detention early so you may attend to it. Have a pleasant afternoon.” I looked down and the spot was actually not quite as noticeable as you’d think; thankfully I was wearing dark jeans.

It was really just more uncomfortable than anything else. I had shot quite a healthy load and, as I walked down the hallway from her classroom in a daze, I was vaguely aware of the rapidly cooling sticky mess trickling down past my scrotum and lingering on my perineum.

I stopped off in the boys’ room but, as you might imagine, the mess was more or less impossible to clean up. I finally gave up on the inabsorbent institutional toilet paper they stocked in the stalls (it was just shredding and making an even bigger mess) and finally just stripped from the waist down and used my jockey shorts as a rag, wiping down my cock and balls and adjacent cracks and crevices. I remember wishing for warm soap and water but, even a half hour after the bell, there was no way I was leaving that bathroom stall naked and cum-covered. Instead, I stuffed the soiled jockeys into a pocket of my backpack and walked all the way home with my cock hanging loose, grazing the damp denim of my spunk-soaked jeans. It was uncomfortable as hell–but 100% worth it!

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