Trinity Finishing School Ch. 03

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Hugh takes school's admin Polly.
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Part 3 of the 4 part series

Updated 06/08/2023
Created 07/13/2017
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Mark and I returned to his office and sat down. "So what else do we need to discuss?" I said.

"Well, fall term starts in two weeks; I'd love to have you here for the start of classes," he looked at me and I nodded affirmatively. "Wonderful, then we just need to take care of some administrative details, there's an employment contract that has some NDA language, payroll forms; you'll need an office and supplies plus we'll need to settle on a class schedule and syllabus. Bob Jenkins handles the class scheduling -- I'll have him reach out to you tomorrow to discuss that." He pressed a buzzer on his desk. "Polly handles all the other clerical aspects -- she's actually the graduate we didn't place some six years ago that I mentioned earlier. We decided to keep her on here instead and she has been an absolute jewel."

Polly walked in and stood in front of Mark's desk with her hands clasped behind her back. "Yes, sir? How can I be of service."

"Mr. Jorgen here has just accepted the position of math and computer teacher. He will start with the fall term."

Polly turned and flashed me a big smile that could melt icebergs. "Why that's wonderful! Welcome to Mount Trinity Mr. Jorgen, I'm sure it will be a pleasure working with you."

"So we need to get some paperwork together for him, would you please go fetch the standard employment packet."

"Of course sir, I'll be back in a moment."

"Mark, thank you for the offer and the demonstration -- I'm incredibly excited for the opportunity after that demonstration."

Mark walked around the desk to shake my hand and looked down to notice my still uncomfortably bulging crotch. "Yes, I can see how excited you are. I'm sorry about that but even allowing you to be in the room today was pushing it a bit. After all, the girl had never seen you before that moment."

"I understand completely."

"Still, we can't have you getting the wrong idea about us -- we take care of our own." Polly walked in with the promised documents. "I have some business to attend to right now but Polly can handle the paperwork. Polly, Mr. Jorgen attended a discipline session with me earlier today and it has left him somewhat agitated -- I expect you to be a team player and comfort him to the full extent of your abilities. His niece will be returning from her tour of the grounds in about half an hour or so; until then you are to obey him as you would me. Are my instructions clear enough?"

"Crystal clear sir," Polly glanced at the bulge in my pants. "My Jorgen does seem to be abnormally flustered but I'm sure I will be up to the challenge of easing his discomfort."

Mark smiled, "Hugh, I leave you in capable hands." He leaned in close and whispered in my ear, "Use her well -- you don't need to be at all gentle." He turned and walked out of the office leaving me there alone with Polly. Any ebb in the strength of my tumescence since watching Jenny's punishment was gone -- I was rock hard again. I would have gone far out of my way to meet a woman that looked as good as Polly in other circumstances, and here she had simply been made available for my 'use'. Matt was right -- I was going to owe him big time for introducing me to this place.

"Let's take care of the niceties first, shall we?" I said. She nodded and spread the papers out on the principal's desktop. I moved behind her right shoulder and put my left hand down flat around her other side -- effectively trapping her. Even in heels she was considerably shorter than I am, and much slimmer. "So, where do you need my signature?"

"Here, here and here," she flipped a few pages and pointed.

"Hmmm, let me read this for a second," I moved closer and leaned forward, pressing my body into hers and pinning her against the desk so there was no question she could feel my stiffened manhood against her hip. I scanned the documents and found them generally basic and reasonable -- the non-disclosure part protected me as much as the school -- but I liked the dynamic so I took my time. "So, what does your job consist of?" I asked, not looking at her though I was no more than a couple of inches away from her face.

"I manage the principal's calendar, including all travel arrangements; I deal with all external vendors for school and office supplies; and I answer the phones and handle all mail to the school." She was clearly not rattled by my aggression so I reached over to sign my name, pressing against her even closer. She smelled fantastic -- fresh and feminine -- and her trim toned body felt even better.

"Is that everything?" I put my hand on her arm.

"That's all the paperwork -- let me just put these away." She walked to the other side of the desk, unlocked a drawer and slid the papers in before returning to the front of the desk. I put my back to the desk and Polly came back to stand in front of me, just out of arm's reach. I smiled, stood to one side and took a long look at the young woman that was mine to do with as I pleased for the next half hour. Polly was raven haired with pale, ice-blue eyes and flawless alabaster skin; she was quite slim and petite -- at most 105 pounds -- but with shapely legs and a reasonable bust; this was going to be very enjoyable.

"Before we start, is there anything I should know? Any preferences you may have? Anything that is off-limits?"

"Sir, Principal Scoletti has directed me to see to your needs, whatever they may be, and I will do my absolute best to comply with his instructions. I am yours to do with what you will." She looked sideways into my eyes, "Nothing is off-limits."

"Perfect. First, until Principal Scoletti returns to this office you will call me Master. If you forget, I will punish you."

"Yes, Master."

"Good, now take off your blouse," she didn't hesitate, unbuttoning her top and sliding it off her arms revealing a surprisingly full pair of breasts covered by a lacy black brassiere. She moved to put it down but I stopped her, "You are not to move unless I specifically tell you to. Stand right there." She froze and held her place. I held my hand out for her blouse, folded it neatly and placed it on a nearby table. I walked up behind her ran my hand lightly across her bare shoulders; she shivered involuntarily. I strolled around to the front of her, tracing my finger down her side and along her ribcage under her bra as I moved. "You're very quiet," I observed. "Do I make you nervous?"

"Yes sir, I mean no sir. I mean, Master," she reddened, realizing her mistake. "I'm a little nervous -- I'm not really sure what to expect."

"So that's one punishment you've earned. We'll come to that shortly." I continued to circle, now running my whole palm along her tight stomach and fit young body. "Do you have any other...duties here?" I asked.

She blushed slightly, "Yes, I am sometimes asked to...entertain certain clients who visit the school and I sometimes accompany the principal when he travels as well."

"Entertain? I assume you don't mean hosting dinners or cocktail parties." I was now behind her and cupped one of her ass cheeks with one hand while I unsnapped her bra with the other. She took a quick breath in but otherwise did not flinch.

"No Master, my entertaining duties are generally more intimate."

I came around to her front again and slid her bra off, tossing it onto the table next to her blouse. Her breasts were very nice, full and round B/C cups that barely sagged with long nipples that had each been pierced with a small silver ring. "Well, this is interesting," I said as I took each of the rings between my fingers and gave them a tug. "These must make your nipples very responsive to stimulation -- I'll bet it hurts if clients get a little rough."

"Yes Master," she gasped. "The piercing makes my nipples very, very sensitive and it's painful when they get abused."

"I can imagine. Put your hands behind your head." When she did her already firm tits stuck out and up even more, almost begging to be fondled. I couldn't resist stroking and squeezing them before rubbing the tips of her nipples gently. They hardened almost instantly and Polly moaned softly. "I'll bet you like it when your nipples get mistreated, don't you? Your breasts are so sexy and exciting men can hardly control themselves can they?"

"Yes Master, I love it; it makes me incredibly hot. I know I arouse men when I display myself like this -- I get a serious thrill from the seeing the effect my body has. I know it is wicked and naughty to tease them and it is only fair they get to enjoy my body in return. They get quite worked up when I excite them and they often handle me quite roughly. The pain mixed with the pleasure turns me on, reminding me of my guilt and my obligation to submit to their wishes so they can satisfy the urges I triggered."

I had made my way around to her back again and roughly grabbed one of her enticing globes, pinching the nipple hard as I did so. "Like that?"

"Ohhh! Yes, Master, like that."

"Do you have a chain?" She nodded. "Get it." She retrieved a heavy silver chain from a drawer and handed it to me. I clipped it to the nipple rings and the chain dangled below her navel, pulling down noticeably on the engorged nubs.

"Who are the people you generally entertain? Do you service the faculty on a regular basis? Principal Scoletti?" I unzipped her skirt as I said this letting it hang for a moment on her hips before I slid them to the floor. "Step out." I folded the skirt and placed it on top of her other clothes -- she needed to return to her front desk in reasonable order at some point. She was wearing very sheer black stockings with a garter belt and a tiny little black lace thong that covered her mound only barely and her round, athletic ass not at all.

"No, Master, the faculty usually has their hands full with the students -- though Principal Scoletti will sometimes make use of me, especially when we are travelling together. Most of the time I interact with potential placement clients who can get quite...Unnhh!" I had torn off her thong and reached around to begin rubbing her clit, "hot and bothered...Ohhh! after interviewing some of the prospective graduates at our job fairs. Nnnggh!" I was pressed against her back now, my throbbing penis wedged between her cheeks, one hand rubbing her twat in tight circles while my other was mauling her breast making the chain swing and tug on her nipples. "Clients are not allowed to touch the students or speak with them without a chaperone present, though they can and do ask very intimate questions and request students to model very revealing outfits. Mmmm! Oh sir! I mean Master! You are distracting me terribly! Unnhh!" I had put a finger inside her box and she wasn't kidding -- she was sopping wet.

"That's twice now," I breathed in her ear. "Continue."

"Ahhh! The clients can get quite flustered by the interview process and Principal Scoletti often directs me to...Unnhh! alleviate their distress, sometimes several of them at once. They also often instruct me to call them Master and take their frustrations out on me most savagely. Since I am a graduate of the school as well, Principal Scoletti calls me the best advertisement for the program he could ever have."

"Do you talk with the students often?"

"Unnhh! Yes, Master, all the time. I'm like an older sister to them, plus I've been through the same program so we can relate. The girls...Unnhh! want to know what life is like as a graduate, get inside info on the placement process and clients...Ohhh! swap gossip about the staff. Ahhhh! Master, please!" I was now sliding two fingers in and out of her juicy little quim and she was having difficulty obeying my order to stand still. I spun her around, grabbed the hair at the back of her neck and forced my mouth onto hers, invading her mouth with my tongue as I grabbed her shapely ass. She responded enthusiastically, kissing me back with abandon and pressing her naked body against me while her hand slipped down to grab my unit through my pants. After a minute or so of making out I broke away -- she was flushed and panting.

"All right, get on your knees and take out my prick," I ordered. She couldn't wait to comply, fumbling with my belt before yanking down my pants and boxers. When I'm fully erect, my cock is a little over twelve inches long and four inches around -- Polly must have known I was packing some weight but she still gasped in shock when it sprung out in her face.

"Master! Your cock is gigantic! I've never seen one that size in my life! It's almost as big as my arm -- I don't know if I can handle such a monster!"

"We're about to find out. It's extra thick and painfully hard because of that hot little body you've been shaking and rubbing against me. Show me how good you are at taking care of the problem you created."

"Yes, Master. I'm very sorry to have gotten you so aroused with my shameless teasing. I should be severely reprimanded for my behavior. You must teach me how dirty little sluts get treated when they affect you this way." God she looked hot, kneeling at my feet in just a garter and stockings, knees spread displaying her shaved box, fantastic ripe tits sticking straight out with the chain connecting her nipples swaying from her elevated breathing rate. She looked up at me with those big eyes, pure white skin slightly flushed from excitement, a little apprehensive over handling my unit but acting like she genuinely felt guilty about it.

"Suck on it. I want to feel your silky mouth caress every inch of my manhood. Show me how good you are at swallowing a real man's dick."

She swallowed nervously but nodded, "Yes, Master." She spat on my hammer and began to stroke it softly with her dainty hands, licking the precum off the tip before moving her tongue along the underside of the shaft. After a minute of this preamble she stretched her mouth wide and managed to get the head past her lips. I didn't see how it was going to fit down her gullet but I was not about to let her off the hook so easily. She started bobbing her head, getting about three inches in at a time, jerking the rest and looking up into my eyes bravely -- I could feel I was hitting the back of her throat. I have to say it felt terrific but I wanted more. I glared down at her and she knew exactly what I intended.

She rose up as much as she could and pushed her head downward on my pole, swallowing in an effort to get it deeper. She struggled, gagging and drooling for several seconds before backing off and taking a breath. Her second attempt got no further so on her third try I grabbed her skull with both hands and shoved it down on my shaft with all my strength. She was swallowing and trying to stretch her neck when finally the head slipped past and another three or four inches disappeared. Her eyes bulged and began to tear up, as I pumped my thick tool past her distended lips. She was definitely working hard, gulping down eight inches of meat between coughing, retching and slobbering when I let her up for air. There weren't many women around who could deep-throat my colossus as far as she had so I enjoyed the opportunity for a while longer, fucking her face with a steady rhythm while she gazed up at me, tears streaming down the sides of her face and long gobs of spit hanging from her chin.

I didn't want to finish before I sampled more of her charms though, so I withdrew and let her catch her breath before asking if she had any rope. She composed herself, stood and walked to the same drawer she got the chain from, removing a coil of silk rope and handing it to me without batting an eye. "I haven't forgotten about the punishment you earned for disobeying me. Give me your hands."

"Yes, Master." I tied them together and grabbed the chain dangling from her breasts. "Ohhh! Oww! Owww! Master, it hurts!" She stumbled behind me as I dragged her by her nipples over to the desk. I looped the chain over the back of her neck and pushed her face down over the desktop tying her hands to the legs on the other side. She was pretty helpless in this position, legs pulled straight but still standing on the ground and derriere sticking invitingly in the air. I got the belt out of my pants and cracked it in my hands as I stood behind her. Polly twisted her neck back and forth to see where I was but she didn't have enough slack in the rope to do much. I admired the view of her long, toned, stocking-clad legs on three inch heels leading up to her sweet pink vulva, already swollen and wet with excitement, topped by a firm round ass accentuated by her being bent at a right angle over her employer's desk.

"You were instructed to obey me yet you ignored my wishes twice -- I cannot let that pass without a response. You must learn to follow directions. If you show proper contrition and welcome the consequences I might be inclined towards a shorter lesson."

"I understand, Master. I have been insubordinate and need to be punished for my transgressions." Thwackk! She stiffened as I brought the belt down on her exposed bottom. "Ohhh! Thank you Master!" Thwackk! "Ahhh! Thank you, Master!" I varied the time between blows so she could not anticipate them. Thwackk! "Oh, Master! Teach me well!" Five more swats from the leather and the snow white skin of her bum was bright red. I had seen enough; my dick was so hard for this lithe, submissive young woman that I almost felt a little lightheaded. I needed to take her -- now.

I swung the belt in the air so she could hear it, but instead of strapping her again I guided the head of my foot-long bar of pink steel into the opening of her tender pussy. I heard her sharp intake of breath as she realized I was poised to take advantage of her vulnerability in a more invasive manner. "Master, I am at your mercy! Please do not violate me with your monstrous cock too brutally! It may be more than my slender body can handle!"

"You insisted on learning how I treat dirty teasing sluts -- my tuition is at your door. You should be prepared for instruction that will be neither easy nor gentle." I slid about three inches of my prick inside her juicy cunt.

"Aannnhhh! Master, it's so thick!" I began to work my phallus in and out of her tight little box, deeper with each thrust. "Unnhh!...So big!...Unnhh!...Never felt anything...Ohhh!... like it!...Annhh!" I was about halfway in now and she was as tight as a novice, her slick velvet tunnel squeezing me delightfully.

"You're deliciously snug, Polly -- completely at odds with your stories about your entertainment exploits." I continued to force my fat snake deeper into the hole.

"Mmmhh! Yes, Master -- part of my job requirements...Unnhh!...is to keep my whole...Unnhh!...body toned. Annhhh! I work out regularly...Unnhh!...including Kegel exercises. Ohhh!" I was sliding ten inches of meat into her now, hammering against her cervix, one hand holding her hip while I spanked her already reddened ass with my other hand as I pumped. She was moaning with each stroke, a thin sheen of sweat appearing on her body, her hands clenching and unclenching in a fruitless attempt to grab onto something as I abused her. "Unnhh!...Master! So deep!...Annhhh!...So full! Owww! Ohhh! Master, I can't...Unnhh!...believe I am taking...Annhh!... so much dick!"

She now thought she was taking all I could give so it was time to unleash the final measure of my manhood. I grabbed her tiny waist with both hands, cocked my hips back and rammed my fuck stick into her as hard as I could. I felt the knob squeeze through her cervix as I sank the last two inches into her. "Aaaiiiee!! Annnhh!! Oh my God! Unnnhhh! Master, you're splitting...Ohhh!...me open! Unnhhh! I can't evade...Unnnhh!...the brutal pounding!...Annhhh!" I held her tightly and pushed her down into the desk as I ravaged her, slamming my crotch into hers with abandon.

I was into a rhythm now, my thick piston like a jackhammer relentlessly reaming her defenseless cunt. I could feel her cervix slip over the head of my prick with each push, exciting me tremendously. "Unnhhh! Master!...Ohhh!...So rough!...Unnnhh!...Too much! You are...Unnnhh!...rubbing my clit...Annhh!...on the edge...Unnhh!...of the desk!" I sucked my thumb to get it wet and jammed it into her little rosebud. "Owwwww!! Ohhh! My ass too!...Annhhh!" Her ass was tight as well and I could feel my shaft sliding past through the thin wall separating the canals. Though I was intrigued I was getting too much action out of raping her sweet quim to change gears now. She was wriggling and her arms were straining against the rope, desperately trying to end the harrowing defilement she was enduring -- there was no escape. "Ohhh!... Unnhhh!...Master!...I'm going to...come!...Unnhhh! Fuck me! Fuck me harder! Unnhh! Force your massive cock inside me! Annhh! Make me take...Unnhh!...every colossal inch! Annhh!" I complied, of course, smashing my hips into her ass and then also reaching out to grab the chain that was behind her neck. She arched her back and screamed from the pain as I pulled hard on the rings through her tender nipples -- at that moment her entire body shuddered in a massive climax. "Aiiiee! Eeeeeeoooooww! Unnnhh! Ahhhhh! Mmm! Mmm! Unh! Unh! Unh! Unh!" She twitched and spasmed as the orgasm rippled through her, the contraction in the walls of her vagina sending me over the edge as well.

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