An Education Pt. 02 – Anal – Free Sex Story

All characters herein are assumed to be 18+ years of age and any similarities to persons living or dead is purely coincidental.

Continued from An Education – Part 1, Professor Jane Hoffman has uncovered an Anal Sex clique amongst the undergraduate population of U of M, spearheaded by a star athlete who has now invited the once-reserved professor to join, unlocking a secret side of her in the process. We rejoin them in her university office



The long black fingertips struck the glass buttplug hard, bouncing off with a dull ‘ping’ like keystrokes on a typewriter, typing out the message ‘GET READY’ in a language only her Ass could read. The shockwave it sent through the professor buckled her knees and she fell into Jerome LaGrange’s strong arms, hugging her close as she vibrated like a tuning fork.

The dilator had her stretched so wide that each movement made her hole spasm angrily, bobbing the plug in and out of her in short strokes as it rubbed up against the engorged g-spot on the other side of her Anal wall. Jane closed her eyes and let her weight fall onto the wide receiver.

“Here, here,” Jerome whispered in her ear, lifting her up by the waist as she melted in his arms. When she was high enough for their faces to be level, she wrapped her legs around his hips, opened her eyes and leaned in for a kiss. Their tongues met first; Jane’s short, thin tongue mashing against Jerome’s long, wide one only briefly before it behind her teeth. Advancing with her thin lips she sucked at the tip of his tongue, opening her mouth only to bring more of his sweet thickness into her.

When their lips connected, Jerome got to work, swirling around inside her mouth, thrusting deeper as it twisted. As he poked playfully around with his tongue, he picked her up, moving his hands from her waist down to her asscheeks, each of his wide mitts palming a cheek like a football and pushing her skirt up. This left his digits Free to weave together around the glass base of her buttplug and hold it tight, crisscrossing on either side and creating a little seat for her to rest her weight on.

“Mmmmmm,” the professor hummed, eyes blinking open while her mouth was filled with Mr. LaGrange’s slippery explorer.

“You got it in, that’s the first step, but now it’s time for your test to begin properly,” he said, pulling himself out from her mouth momentarily, “have you done the work?” His raised eyebrows begging the question while his soft tongue slid back into her mouth deliciously.

Resuming their deep kiss he bent the intertwined knuckles under the rim of the buttplug, the tiny tug pulling the plug down and placing pressure on her hole to keep it inside her, Jane having to clench to suck it in. This caused her to simultaneously suck his tongue equally hard, drawing it deep enough to rest the tip at the back of her throat comfortably as saliva poured from his mouth into hers.

Again testing the resolve of her asshole, Jerome moved his fingers out from under the base, placing fingertips on either side of the valley of her cheeks. As gravity pulled the toy down Jerome’s fingers pulled gently at the skin of her asscrack, spreading her cheeks slowly outward. This stretched her hole open, weakened her hold on the plug, and caused her to re-double the clench on her midsection, her abs flexing against the blouse and beginning to sweat.

Jane grimaced as she held firm, muscles in her belly and pelvic floor now twitching sporadically. Just as she was beginning to think she couldn’t hold it anymore, Jerome pressed her cheeks together and re-crossed his digits, allowing her to sit in his hands and catch her breath.

“You’re doing great,” he whispered to her as she looked down to her chest, panting, “and your grip’s amazing. What about depth? Have you studied that yet?”

Waiting for her to look up and nod, he lifted her higher yet, easily propping her Ass up and sliding his one arm, then two, under her legs so her knees now rested on his shoulders. Sliding his hands back up between her shoulder blades, he leaned her back, letting her Ass rest against his now-hard abs and pressing the glass phallus deep inside her.

“Oh, that’s deeeeeep,” Professor Hoffman squeaked out as the tip of the hard plug reached a new depth, forcing her body to shift around it.

“Actually, this is deep,” he countered, grabbing the tops of her shoulders and pulling down, slowly pushing her further against him, the unforgivingly hard object finding places only her soft, black dildo had reached. All of her muscles went taut as she went still, not daring to move. As he alternatively released and pushed her down against his torso Jane was speechless, air escaping her open mouth in little wisps.

After only a few seconds he stopped pushing and allowed her to relieve the pressure on her internal organs by bending forward. Jane held the back of his neck and bent further at the hips to lean in and kiss him again, showing off her flexibility.

“You’ve done the work, ma’am,” he said between kisses, thoroughly impressed so far, “but are you prepared for me to thank you properly?”

Professor Hoffman still had her knees on his shoulders as he turned and laid her down gently on the oak desk that dominated her office, biceps bulging as he cradled her head and neck down onto some random papers. With the speed and dexterity of a Horny teenager she untucked the blouse from her skirt, unbuttoned it and tossed it off the desk, revealing the tight lace bra that barely covered her areolas.

On the other end Jerome took his time, savoring the view of the fit 40-something woman undressing before him, tugging on the zipper to her skirt and shimmying it over her butt and over his head as he pulled it off. Her ankles now perched on his shoulders he followed the length of the thigh highs she had on, running his hands down the edge until they met with a clasp that ran up to her black lace garter belt. At the base of her inner thighs he noticed a small black triangle of lace covering up the bottom half of a patch of well-kept pubes, a little black tuft poking out from the top.

Finding the two strings that connected at the top he ran his fingers under the lace and pulled up, extracting the tiny g-string from her, the center strand catching on the glass toy and firing a bolt through her as it tugged past. Biting her lip from the shock, through gritted teeth she looked up at him and replied, “I’m ready.”

The professor lifted her heels from behind Jerome’s head and spread them as wide and back as possible, gaping her Pussy wide and pushing the dilator out an inch in display. She pressed down on her inner thighs to keep her legs open, high heels pointing east and west at once. The ring of her asshole strained against the widest part of the plug, her skin tensing and jutting out in a brown circle around it.

“I can see that,” the starting line Wolverine remarked and placed the middle string of her underwear into his mouth and dropping down to his knees, his eyes just barely visible to the professor as she looked down the gun sight of her clit hood. The thought of him sucking her moist undies opened her hips a fraction more, tendons stretching as she presented herself fully to his inspection.

His mouth was already slick with her panty juice but the sight of her gaping Pussy, dripping grool down and around the large glass plug fighting to come out of her Ass, made it gush. Grabbing the base of it with his fingers he turned it clockwise inside her, the plug spinning effortlessly as he turned her ecstasy up like one would a car stereo. As it spun silently in her Ass her Pussy began to pulse open and closed and started to quiver, her fourth Orgasm of the day reaching its peak.

Taking the initiative Jerome LaGrange dropped her g-string on the floor, leaned in and slid the length of his wide tongue into her wet slit as it spasmed, burying his face in her lips and resting the tip of his nose on her clit. As she bucked on the desk he grabbed her Ass and pulled her forward into him, letting the prof grind her wet, bald Pussy all over his face.

“Shit, shit, shit, shiiiiiiit,” she groaned as she wrapped her legs around the shaved nape of his neck and smashed him against her slippery vibrations. Wearing her Pussy as a face mask he held onto her, pushing his tongue deep and pressing his nose into her engorged nub. Holding him a little too long as she came down from on high, he wiggled his head out of her grasp and inhaled deeply.

“Ahhh! *cough cough* you are ready,” he sputtered out as he caught his breath, “but, as coach says, ready isn’t prepared.”

Tired but still alert, Jane understood the difference.

She lifted her legs straight up and wrapped her arms around the back of her knees, rocking back on to her shoulders on the desk, presenting her Ass to his kneeling face. The base of the plug now pointing to the ceiling it was begging to be pulled out.

Jerome hooked two fingers under the lip of it as Professor Jane Hoffman gave the flared dilator a slow internal push. It slid out of her gaping hole smoothly, stretching the ring of her Ass to its maximum and staying wide open after it had been removed.

At the same time they both let out a slow “ohhhh” as it came out, Jane relishing the pressure of the stretch, Jerome enjoying the view of it.

Examining the oversized plug Jerome saw it to be crystal clean, only some Pussy juice and lube streaking down the side. As he held it and looked for a place to put it down, he saw Jane’s face and smiled wickedly.

The professor’s tongue hanging out and dripping saliva he brought the plug up between her legs to her mouth and set it gently inside, stopping as the bulge made light contact with her back teeth. She circled the tip with her tongue, lapping at her juices hungrily, to show him she was prepared to accept his gift. As she sucked on the glass toy, Jerome grabbed a hold of each leg and held them back wide, again dropping down to his knees in front of her.

“I Love it when they come prepared,” he said, under his breath, and circled her gaping asshole with his tongue. Pressing firmly with the tip, his tongue ran along each wrinkle and bump of her ring like it was reading braille, spiralling each orbit towards the center. Once in the middle he toyed with the hole, sending little thrusts of a pointed tip in and letting it expand inside until eventually he was fully tongue-fucking her asshole.

Until a few days ago the professor could never have dreamt of experiencing anything like this: She was almost completely nude, legs spread wide in her university office, asshole gaping as a student and star athlete ate her Ass out, diving into her anus and savouring it as he sent his softest parts into her most forbidden places.

“Lick me deep,” she moaned, glass plug still lolling in her mouth.

Pushing her legs back and pressing his nose into her still trembling Pussy, Jerome sent his tongue as far as it could go into her rump, licking the insides and lapping at her stretched hole.

“Let me taste it, please,” she begged, tugging on his ears playfully, hardly believing the words coming out of her own mouth.

Jerome loved to hear them talk nasty and he always aimed to please, so he pulled his worm-like tongue slowly out of her Ass, taking extra time to rim the top of her sphincter and taint as he lifted his head. Still hanging out of his mouth he brought it slowly up to hers, letting her catch a bead of juice that hung from the bottom, then dipping it between her hungry lips. Kissing deeply, they both savoured her good work.

“Sorry for doubting you, professor, you’ve come prepared. Now I need to get ready so I can show you my appreciation,” Mr. LaGrange said to her and stood up straight, between her legs.

Pushing down on the waistband of his sweatpants he exposed his balls and shaft as they fell to the floor, the head of his dick below the table’s edge and not visible to Jane. Grabbing it with two hands he placed it on top of her stomach, his dark sack resting on her labia, the smooth shaft resting comfortably on her pubes and the engorged hooded tip pointing like an arrow at her belly button.

Although she was incredibly aroused, looking down on his big black dick gave her pause. It wasn’t as thick or veiny as she had envisioned in her mind, slightly thinner than her dildo actually, but where it lacked in girth it made up for in length, and the professor got a little scared as she calculated how far into her colon it could reach. The shaft arced up then down and the head was tilted slightly to the left, she noticed, creating a bow shape that touched her Pussy and stomach simultaneously with a little gap in the middle. Imagining it buried in her asshole made her quake involuntarily.

She had never been with an uncircumcised man, or even seen one in the flesh, her heart racing as she examined his covered tip. The head was the thickest part too, a shiny smooth surface peeking out from under his foreskin, his hole staring her like a lidded eye as she looked down.

As she peered into his tiny hole a drop of pre-cum oozed to the surface in anticipation. When the bead of cum threatened to drop, Jane reached down, scooped it with a finger and placed it in her mouth, savoring his salty present.

‘Delicious,’ she thought as her hands traced the down length of it on her stomach. When she reached the base of the shaft Jerome pushed her body away carefully across the desk, papers underneath her sliding alongside, until her head hung off the other side. Looking down curiously, she saw him walk around to her side as well, stopping above her head and this time placing his balls on her nose and draping his length down the front of her chest; his cockhead now pressing into her cleavage.

The musky smell of his balls intoxicated her as she breathed in deep, sucking each salty brown orb individually into her mouth and lapping at the bottom of his smooth sack as he purred above her. When she lifted her hands to stroke him, he pushed them away gently; she’d done enough research to know what he wanted her to do.

Jerome was impressed with the professor so far and his shaft hardened further as she set her palms face down on the desk and felt her push her tongue down flat against the underside of his shaft, indicating he was Free to fuck her throat as he saw fit. Pulling back a couple inches until his balls slid onto her forehead, he looked down to see her staring up at him hungrily, her eyes wide with his shaft sitting between them. He had to look away first as he stifled his Orgasm, not wanting to cum too soon.

‘Damn, I’m about to blow like I’m in highschool now?’ he thought, looking up at the ceiling to calm himself. ‘This is a grown-Ass woman, Jay, not some dumb sophomore, remember? Get it together!’

Her stare softened as he twitched on her tongue, his shaft straightening and adding yet another half-inch to its length as he looked up and away, delaying his eruption. Taking care not to set him off she kept her hands and tongue still as she smiled proudly to herself.

After a half-minute Jerome began rocking his hips painfully slowly, sliding his dick along her tongue and pulling the head slowly back up her neck until the tip of his sheathed cap rested on the tip of her tiny tongue.

Professor Hoffman darted her tongue up over the hole of his dick, tasting a salty patch as it poked up under his foreskin and wedged itself along the rim of his crown. Pressing down on his head Mr. LaGrange pointed it at her mouth allowing her tongue to run the under the tight hood of his hidden jewel, tracing the circumference inside and slathering it with her spit. Pressing her wet lips to his foreskin she paused and nodded at Jerome who was looking down approvingly, mouth agape.

The unspoken terms of their agreement now confirmed, he pressed his head down further, her mouth sliding over it and taking in three full inches in one stroke. Pulling it back out, a string connected his tip to the back of her tongue before he slid it back in further into her throat.

Just as her mouth had performed during her prior dildo training, her throat opened at the slightest push, barely providing any resistance as he inched his manhood into her neck with small, slow thrusts. When his tip started to poke at her vocal cords, she let her head hang of the edge of the desk and it opened her up even further.

On the next stroke his head slid past her throat barrier, unsheathing itself completely inside her, and the remaining length slipped right down into her neck, his balls again resting on her upturned nose.

He paused to halt another Orgasm as his whole rod tightened and fought against itself not to pump his seed directly into her stomach. As he expanded inside of her, she held her breath as her neck muscles quaked, creating a similar tensing of her kegel muscles below.

‘Naw, naw, there’ll be time for this yet. I got a plan for this nut. Stick to the plan, Jay,’ he scolded himself in his head.

A tap on his thigh pulled him out of his thoughts and he pulled himself out of his professor’s throat, dragging a mess of white strings out of her as she caught her breath. The saliva and slime dangled off his shaft in ropes and she tried vainly to catch them with her lips as they dripped on to her face, painting it in tiny streaks.

“More. Please,” the professor begged softly, but the wide receiver seemed to have other plans, hesitating instead of diving back in. He wouldn’t last another minute in her throat without busting his load deep inside her. So, the professor tried again, this time softer still.

“Please, let me taste it some more,” she repeated. Waiting a beat and remembering her research she added sweetly, “Daddy.”

All his careful plans were set ablaze once he heard her quiet plea and his resolve went up in smoke. His whole dick hardened, flexed up once, and flopped down on her face as he pulled back to guide his head back into her depths. Knowing he had only a few full strokes before he’d blow, he cradled the back of her neck off the desk as he sliced the length of his brown spear down into her, his balls slapping her face audibly.

Six full thrusts into her later his shaft started pulsating again, only this time Jerome let himself go, abandoning his grand scheme and allowing himself to release his cum inside her greedy neck.

As he leaned back and looked up at her office ceiling preparing to spurt, she clamped her hand around his sack and squeezed it firmly, tugging his balls down once and holding.

His eyes snapped back down and he felt the sharp stomach ache of pain that comes with being kicked in the testicles. She released his sack and the twinge of discomfort evaporated, along with his Orgasm, the third such fire having been put out. Jerome shrunk a little inside her throat and stood dumbfounded and reeling.

Still half buried in her throat, Jane rolled over on her desk, maintaining eye contact and taking care not to pull him out completely, until she was on her stomach. Using the side of the tabletop to push herself she slid backwards off his slightly deflated length and dropped her legs off the front of the desk bending at the waist. Like she’d seen in so many of her appointments with him, Jerome was rendered speechless by a new concept on the other side of her desk, only this time he was pantsless, his sloppy dick out and drooping into some papers.

Reaching her hands back to her Ass cheeks, Jane Hoffman rested the side of her head on the table and said confidently, “Sorry, but I believe that’s meant to go in here,” pulling her cheeks apart and smiling to make it clear she was not sorry.

After a few seconds of silence she looked up again to his stunned face and asked to be sure, “Am I wrong?” As his vision came back into focus, seeing her bent over the desk, a surge of energy ripped through his body and Jerome pulled his sweatshirt down and over his head in one fluid motion, revealing his long, toned black torso in response.

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