An Education Pt. 04

"I'm so, so, sorry," Dewayne blurted out, trying to pull his shirt down over the inflation in his pants.

"Don't be sorry, honey," Jane retorted, "you have nothing to be ashamed of." She stretched out her big toe and touched the end of the trouser snake sending a full-body shake through the sophomore. "Once you're hard, take your condom and roll it down over the head. Don't pull, just let it unravel as you push the edges gently over the tip. Now some of you boys are very well-endowed, so make sure to get the extra-large condoms so you can roll it right down to the base like this." Getting the rim of the rubber all the way down to the simulated scrotum she leaned over and let another glob of saliva drip down onto the covered tip, smoothing it down its length with her hand.

"Make sure it's nice and wet before sticking it in," Jane explained, stroking the shaft, the mass in his pants flexing every time her grip reached the silicone sack. Turning back to Dewayne, she asked, "Easy, right honey?"

"Uh, yeah, yes, uh miss Jane," he said, uncertainly.

"That's a good boy," she acknowledged sweetly, "now show me."

Dewayne's eyes grew wide as he fumbled around with the foil packet in his hand before tearing it carefully like he was shown. Fishing out the condom he went to stand up and illustrate what he had learned on the dildo stuck to the desk, but the professor placed her left foot on his chest to stop him.

"No," she said firmly and gave him a gentle push back down into the chair, "you have everything you need, honey, right there." She smiled and stared down her nose at his pants.

A red hue immediately washed over Dewayne's face as he looked to Isaiah for guidance.

"Do as she says, bro," Isaiah told him with a smirk.

Holding the condom between shaking lips, Dewayne frantically unzipped his jeans and shimmied them and his boxers over his knees. His thin penis followed the curve of his left leg, bending up near the narrow, uncircumcised tip and it rippled in the light of the office, one long vein splintering down the whole shaft. Grasping the condom with two hands he tried to roll it over the tip, only for it to slip off. Trying again he placed the tip on but couldn't roll it; it was inside out. Reversing it and attempting again he almost got it over the head, but his foreskin shifted underneath and it redirected the condom off the top. He was flustered and embarrassed when the professor slid off the desk and grabbed his hands in hers.

"Aw, honey, don't be ashamed, this is normal," Jane comforted him softly, "let me give you some pointers." She plucked the condom from his hands and pulled him up out of the chair and on to his feet while his pants fell to his ankles. Squatting down in front, his cock was at eye level when she grabbed it with one hand and pulled the hood back, exposing the purplish, brown glans underneath. His dick was hard as a rock, standing up at 45 degrees and looked painfully engorged, Dewayne wincing as her breath wafted over his exposed cockhead.

"If you roll your foreskin back, it's easier to put the condom on, AND you'll feel it more intensely when you're having sex. If you have a nice partner, they can always help you too," she explained, placing the rolled condom on the tip. "If you have an experienced partner, they can make it fun," she continued, putting her lips around the reservoir tip of the condom and pressing down with her mouth. The condom rolled down over the edge of his mushroom tip as she pushed the rim with her lips, taking his covered head into her mouth. Coming off his dick and looking up, he looked as if he had seen a miracle, his face displaying wonder and awe.

She smiled at him and went back down on his dick, using her lips to unravel the condom down his length in longer strokes. The bitter taste of the latex and lubrication were eventually washed away by her saliva as she took his length in her mouth, the tip just cresting the bend into her throat when it was fully buried. Seeing the tendons and muscles in his legs were taut as piano wires, she knew he was ready to cum. She pulled him out of her mouth and looked up at him again.

"Ok, honey, now show me how you fill it up," the professor demanded up at him before sliding his fully bagged cock back down into her throat, clenching a couple times as her throat convulsed around his tip. With her free hands she directed his to the back of her head and he gently pushed her face further down into his pubes. She grabbed onto his clenched ass-cheeks and pulled herself in as far as possible as he began to spurt, inflating the balloon tip in her neck with his warm jizz. Holding on to the base of the condom, Jane withdrew her mouth slowly, lolling her tongue on the bag of semen as it came out. As his dick hung down, she pinched the condom just past his tip and pulled the stretched rubber off of his dick, the last inch snapping loudly as it came off.

"Oh my actual God," Dewayne finally exclaimed, his naked ass hitting the chair as he fell back into it. Isaiah and the professor chuckled as she stood up and leaned back against the desk once more, holding his used condom up for inspection.

"You can dispose of this in the garbage or wash it down the sink if you think someone is going to try and take it," she explained. She watched the heavy, distended end of the condom twirl around as her thoughts shifted back to the athletic center when she was filled with three similar gifts. "All of you boys make the biggest, thickest loads," she noted as she licked her lips, eyeing the warm goo as it swung like a hypnotist's watch. Bringing it up to her face she pinched her lips around the open end and tipped it up, sucking the salty prize out and down her throat like the end of a freeze pop on a warm summer day.

"Mmmm." She traced the path of his cum with her hand, down her neck, over the mounds of her sweater and patted her little tummy. Looking down she spread her legs and giggled, "Oh, my!"

"Oops, I guess I got a little worked up too," the professor remarked, hopping up onto the edge of the desk. Leaning back and spreading her legs further she showed the boys what she meant as a dark spot had formed in the seat of her otherwise gray trousers. "It's very important that you take care of your partner, Dewayne," she said, turning her attention to the other man in the room. "Isaiah, baby, can you show him what to do?"

Without saying a word, Isaiah jumped to his feet, the bulge in his sweatpants announcing his erection as it bounced between his legs. Jane unbuttoned and unzipped her pants and leaned back on her elbows, lifting her ass up for the point guard. In one uninterrupted motion, Isaiah hooked her panties and dress pants with his long index fingers and pulled them over her cheeks, down and off her legs.

The professor wiggled her toes as she spread open her legs to display her glistening lips. She had shaped a tuft of her pubic hair into a line that led directly to her clit, the slick round orb poking out from its hood like a pearl. Widening her hips and pulling her legs back, her labia bloomed open, sticky tendrils of her wetness stretching across the gap. Like Pavlovian dogs, both men sucked their lips and swallowed the spit that welled in their mouths. Isaiah knelt in front of the desk and dove in without prompting.

"Good boy," Jane whispered as she placed her hands on his bald head. Looking over it she observed Dewayne as he gawked at Isaiah driving his tongue into the professor. "Dewayne, watch as he sucks on the labia, ooh, and dips his tongue inside in equal measures; never stay in one place too long," she instructed. "Your partner will, nggh, let you know if you're doing it, oh god, right," she continued, gripping his head and pressing it harder as he reached the clitoris. Rubbing his head counterclockwise, Isaiah's tongue followed suit, drawing circles around her engorged nub as it thrummed with energy. Beads of sweat formed on the wrinkles of his head as she held it tight against her crotch until she felt the familiar pulses of ecstasy threatening to spill out of her.

"That's it, baby, right... fucking... there!" the professor whisper-yelled, leaning back on her desk as she locked her legs around the athlete's head. Lifting her hips to force-feed Isaiah her pussy, each time she came down the black plug in her ass knocked on the desk as it pushed deep inside her. Waves of oxytocin flooded her sphincters, alternatively contracting and dilating her holes, as dopamine washed over her brain. She lay down on the desk fully and panted as she released Isaiah from his carnal prison.

Isaiah stood up and smiled at Jane while rivulets of her juice ran through his black beard. Coming down from on high, she opened her eyes, smiled back, and waved him up to her face. Guiding his head to hers she kissed his thick lips and sucked his tongue into her mouth, savouring the taste of herself.

Intertwined on the desk, Isaiah and the professor writhed as they made out, oblivious of Dewayne, or anyone else in the world. Holding her tight, the monster between his legs rubbed up against her dripping pussy, threatening to turn his sweatpants into a cotton condom.

"Can I get in that?" Isaiah asked softly, between breaths.

"You know how to ask, baby," Jane replied, staring at him as they swapped fluids.

"May I?" he whispered in her ear, pausing and quietly adding, "Mommy?"

"Mmm, yes you can, baby, that's a good boy," she cooed in response.

Isaiah shuffled out of his sweatpants like they were on fire, releasing the thick beast she had allowed inside her a few days prior. The shining tip of his immense dick filled her with heat as it pressed past her labia and stretched her hole wide open. She extended her legs straight up in front of him as he crawled up on to the desk with her, kneeling over her as her ankles settled onto his shoulders. Gravity pulled his massive frame down onto her, bending her legs back and inching the width of his cock into her vagina, past the narrow point made by the toy in her ass.

When he was fully inside her, the professor reached up and grabbed her feet by the toes, her hips opening wider than during any hot yoga class she had attended. The stretch was incredible as he began the slow stirrings of his pelvis, hitting every wall as he drew more counterclockwise circles, this time around her cervix with his tip. He leaned down and kissed her again as he began the rhythm of his thrusts: In-stroke and exhale on beats 1 and 3, out-stroke and inhale on beats 2 and 4, they made music in her university office. Little whimpers from the professor added to the harmony as he fucked the air out of her in bursts, while the slap of his heavy balls on her anal toy added much needed bass. A grunt every fourth measure signalled the repeating pattern as they increased tempo and volume. Reaching a frenetic pace, the desk itself contributed to the music, the legs adding a skrrt skrrt sound as they scraped across the floor by millimeters. As their symphony climaxed Isaiah punctuated the crescendo of noise with five consecutive full thrusts, their thighs slapping together like crashing cymbals, and five increasingly louder groans.

"Unnggghhh!" he belted out in the now-silent office. Jane released her feet and reached up to pull down his sweaty head as they kissed quietly, each catching their breath as little pumps of semen filled her vagina.

"Ooh, you are a good boy," she whispered to him as they exchanged the hot air trapped between them. Kissing his head, she gently pushed him up and let her legs dangle off the desk again, the ligaments in her hip and the muscles surrounding her vaginal walls crying out with a delicious burn. Isaiah stepped back on to the floor and pulled up his sweats when they both remembered Dewayne was still in the room, slack-jawed and naked from the waist down, his erection once again sticking up out of the office chair.

"That, Dewayne, is a masterclass in missionary sex," the professor quipped, "and Mr. Williams has obviously had lots of practice, so don't be intimidated." Turning to Isaiah, she said, "Baby, I need to finish up with Mr. Smith, but you can go now," she slapped his ass playfully as the basketball player nodded and made his way to the door. "I think Dewayne is all sorted out now, isn't that right, honey?" she asked the sophomore, and he nodded quickly in response. Isaiah gave him a knowing look before exiting the office and closing the door behind him.

Sitting up again the professor began pulling the arms out of her sweater as she watched the lanky man in the chair stroke his thin dick slowly. She watched as his wide-eyed gaze darted to the milky white puddle forming on the desk between her legs, then to his own cock with a scowl of disappointment.

"Aww, honey, don't compare yourself to him," she consoled him, removing the sweater, folding it, and placing it on the seat behind her. Elbows out as she unclipped the bra between her shoulder blades she continued, "Everyone has their own style and you won't have any problems pleasing a woman." Dropping the bra, she beckoned him up as she slid to the edge of the desk, spilling some cum off the edge in a slow, thick waterfall.

"Come up here and I'll help you," the professor comforted, pulling him close by the hooded head of his dick when he stood up. "This is what makes you special," she told him, running a finger around the rim of his glans. The last inch and a half of his dick bent upwards, creating a fleshy hook with the foreskin pulled back, the thick ridge circling his head acting as the barb. "Angle your penis in and up, not very deep, and stimulate the G-spot by dragging it in and out." She simulated the manoeuvre by hooking her first two fingers in and up towards her pubic bone. The buttplug added extra pressure to her motion, the rubbing of the rough patch inside sending tasty little vibrations through her core. Pulling her digits out she spread them open to show their viscous cream coating before swirling them around the tip of his penis and lubing him up.

"Now you try, honey," she directed him, wrapping her arms loosely around his neck, her legs around his back, and tilting her hips up to help with the angle of penetration. Dewayne hesitated at her entrance for a second until she added, "I'm in menopause, Dewayne, you couldn't get me pregnant if you wanted to." That was all he needed; he slipped himself in and up until the tip pressed against the roof of her vagina.

"Oof, that's it, honey, just pull back from there," she directed him, cooing 'ooh' when he followed instruction. "Mmm that's how you scratch that itch," Jane said as he picked up the pace with his tiny upward thrusts. Each little hop bounced her tits between them and sent multiple shockwaves through her, one originating from her engorged G-spot and the other from her ass, where the base of the plug slapped against her sphincter like a rubber mallet. She pulled his head to hers and kissed the sophomore, mixing their saliva and passing it back and forth. Pulling away she admired him as he craned over her, Dewayne focussed intently on the trajectory of his dick inside her.

"You're doing great, honey, but here's another thing a manhood like yours can do. If you slide it in deep, towards the back, you can slip the tip into a nook just above my cervix and stimulate the A-spot. Hit it right and you can make a woman so wet. Want to try that, honey?"

"Uh huh," he mumbled, focussing on the work he was putting in.

"Good boy," she replied, "pick me up and let me fall slowly on your cock." Dewayne obliged, placing a large hand under each ass cheek and lifting her off the desk. His dick stood straight up as he looked the professor in the eyes and let her weight sink onto him. Each inch she dropped down resulted in his dick sliding up equally inside her, running along the anterior wall of her vagina until the head slid past the top of her cervix and slotted into the crease at the back. The warm tip trembled inside her as he struggled to hold her up.

Jane curled her legs tightly and locked them around his back by the ankles. She moved her hands from around his neck down into a bear hug and squeezed tightly, nestling her head under his chin as she wrapped around him like a backpack worn backwards. Her pussy quivered and gushed internally, adding more volume to Isaiah's deposit, while she squeezed her pelvic floor muscles in long pulses that sent a train of translucent liquid sliding down his shaft. The toy in her ass pushed out and receded as she clenched and released, his grip on her cheeks spreading her hole open wickedly.

"Yum, you're in that spot right now," she whispered into his chest as she held him tight, "can you feel how wet I've become?" Dewayne nodded silently. "Isaiah can't get there, just so you know. He's got a big dick, and he knows how to use it, but most girls can't handle or want that much dick." Coming off his chest she looked up and him and added, "You're a good boy, and your cock is perfect." Bearing down on him again the plug finally broke out of its prison and popped out of her ass, bouncing on the floor. She felt the warm breeze coming from the floor registers lapping at her open hole, tickling and teasing as Dewayne continued to milk her wet pussy in little strokes. She squeezed hard and rode him as he squished his wet thighs against hers.

"I want to cum with you, honey," she softly whispered as she kissed his collarbone and neck, "but first we both get to try something new." Dewayne looked down confused with beads of sweat forming on his forehead as he concentrated on bouncing her on his cock. The professor reached under her legs and ran a hand from his balls and up the shaft, gently scraping a pool of their natural lubrication into her palm. Looking up for second she flashed a mischievous smile before reaching beside them and smearing it up and down the wrapped dildo that was still suction cupped to the edge of her desk.

Observing the implication, Dewayne's eyes grew wide as dinner plates and a second wind reinvigorated his straining muscles. The professor hugged him close once more as he shifted them both over a couple feet until her gaping asshole hovered above the floppy tip of the condomed dong. Her sphincter winked open and closed in anticipation as he guided her stretched cheeks down, slotting the head in with little initial resistance.

"Slowly, honey," she begged his sparse chest hairs as the phallus wormed its way higher inside, spreading and encompassing the space entirely, while squeezing Dewayne's manhood like a vise. Jane had never been so totally filled before, each subsequent inch finding a place inside her she never knew existed.

"Oh oh OH OH... my... God," she mumbled to herself as she slid down both poles, her pussy and anal sphincters spasming uncontrollably on both rods as they wound up and through her. The quivering below slowly fizzled out as both holes gave up the futile fight against their penetrators, replaced by an overwhelming sense of acceptance as the muscles in her abdomen relaxed. When her cheeks finally hit the desk, she pouted to herself quietly knowing there wasn't any more meat to take in.

She had forgotten entirely about Dewayne so when she looked up, she noticed the frozen expression plastered all over his face. He was gobsmacked, like he had been hit with a hard left hook, the tendons in his arm beginning to loosen as he let her weight rest on the desk completely. When he caught her gaze, he snapped out of the stupor and smiled at her, uncertain of what to do next.

Taking charge once again the professor leaned back on the desk, bending the dildo at the base so it angled back with her, placing her heels on the edge and giving Dewayne full view of the situation. Both cocks were equally balls-deep but when she tilted her hips up, they pulled out asymmetrically: for every quarter-inch that came out of her ass, a full inch withdrew from her pussy, dragging the trapped goo out of her in gobs. So, little-by-little, Jane began to grind up and down the slick members, watching Dewayne with a hungry stare as his uncertainty turned to awe.