Chapter 7
Starring: Kaia Gerber and Maude Apatow
With: Kate Beckinsale, Cindy Crawford, Amy Adams and Leslie Mann
Tuesday, August 4th, 2020
Parent-teacher nights at Sofia Vergara’s Summer School for Girls were always a sight to behold. Such evenings at more traditional schools generally made for a rather drab affair, and while crowning moments of such events might include a balding, divorcee English teacher questioning a dumpy housewife about their daughter’s choice of literature, or a bespectacled algebra geek urging a jock dad to convince their disappointing son to try out for the mathletes, parent-teacher nights at SVSSG were one of the highlights of the semester.
And this particular edition of the annual event was no exception. Indeed, all manner of exchanges were taking place in classrooms throughout the famed institution, each one more curious and offbeat than the last. In one room, Evan Rachel Wood regaled Christi Lukasiak about her daughter Chloe’s penchant for 69ing. In another, Kristen Bell talked Madison Beer’s mother, Tracie, through her daughter’s favourite sexual positions. While in a third, Brie Larson gave a concerned looking Uma Thurman a rundown on Maya Hawke’s struggles with double penetration. But that was the mere tip of the iceberg and soon parent-teacher conferences would be taking place throughout the school that made those sexually charged discussions look like a night at the library.
Kate Beckinsale was sitting at her desk in Room 69C, slurping from a cup of decaf, when there was a knock at the door.
“Come in.”
The door eased open and in stepped first year student, Kaia Gerber, and her mother, legendary supermodel Cindy Crawford. Cindy, like Miss Beckinsale herself, was wearing a form fitting, professionally tailored suit. Kaia was dressed more casually in a light summer dress.
“Miss Beckinsale?” asked Cindy as she closed the door behind her.
“That’s me,” the teacher replied, rising from her seat. “And you must be Miss Crawford. Lovely to meet you.”
She extended a hand and Cindy shook it.
“Please, have a seat,” she added, gesturing to two leather bound chairs at the other side of the desk.
“Thank you.”
All three women sat down.
“So, you’re my daughter’s teacher for Blowjob 101, right?” asked Cindy, popping the question like it was the most natural thing in the world.
“That I am, Miss Crawford. That I am.”
“Right. And how’s she doing?”
“Very well, actually. She’s a very quick learner and has a real passion for giving head. Isn’t that right, Kaia?”
“Mmhmm,” Kaia grinned.
“Kaia is great at dealing with precum and never leaves the guy leaking, which, as I’m sure you’ll agree, is one of the most important aspects of sucking dick.”
“Oh, absolutely,” Cindy agreed.
“She’s very good at handling balls. Be it sucking on them or fondling them whilst working the shaft. She’s one of the best multitaskers I’ve ever had. Eye contact is fantastic and she generates a heck of a lot of saliva. Honestly, I don’t know how she does it sometimes!”
“Wow!” Cindy exclaimed, turning to face her daughter. “It sounds like you’re doing really well, baby!”
A smug grin stretched across Kaia’s face.
“She really is,” Miss Beckinsale confirmed. “Though if there’s one area in which she could improve, it’s her deepthroating. Now, don’t worry, it’s quite a common thing for girls her age, and she’s not the only one in the class having a little trouble in that area, believe me. My daughter is 21 now and even she still struggles with it at times. Kaia’s first effort at choking down my TA’s dick came in at...I believe…” She consulted a sheet of paper on her desk. “Yes, 8.2 inches. Not bad at all for a first attempt, but I have yet to see much of an improvement in the following weeks.”
Cindy listened intently as Miss Beckinsale explained, nodding along like the brown-haired British teacher was describing her daughter’s struggles with trigonometry.
“We managed to get it up to…” Miss Beckinsale looked at the sheet once more, “9.4 inches on Monday. A slight improvement but still some way short of our target.”
Cindy puffed her cheeks. If nine inches was seen as coming up short, just how big were these dicks her daughter was being expected to swallow!?
“I see,” she said. “Is there anything we can do to improve that? Do you offer private tuition?”
“I do, but I think it would make for a better learning environment for Kaia if she were to be taught these things by those nearest to her. I mean, we’ve gotten close to one another over the course of the semester. Very close, in fact. Haven’t we, Kaia?”
“Mmhmm,” she replied with a suggestive grin.
“But there really is no substitute for the bond of a mother and daughter.”
“So you think I should teach her?” asked Cindy.
“I do, Miss Crawford. Very much so. Now, I’m sure you know plenty of guys who would be up to the job, but if not I’m more than happy to lend out my TA for a weekend or two to aid in your tutoring. In fact, why don’t we bring him in right now? I’m sure he’d be very willing to assist you. Tyler!”
The door opened and Tyler stepped inside, the handsome TA kitted out in his usual get up of tight white boxer briefs as he strolled into the room. Cindy’s jaw dropped; so much so she almost had to pick it up off the desk, as she caught sight of the young stud’s ultra-chiseled from and the girthy, snake-like bulge coiled in his undies.
“Hi, Tyler,” said Miss Beckinsale. “Come here, honey.”
Tyler stood at the side of the desk.
“Now, as you know all too well, Kaia is struggling a little with her deepthroating,” the teacher contnued. “So I’ve offered up your services to Miss Crawford here, so she can give her daughter a little one on one lesson. Hope you don’t mind.”
“Not at all,” Tyler grinned, as he looked down at the smoking hot freshman and her equally gorgeous, super MILF mother, his mind whirring with the endless possibilities such a configuration could provide.
“Yeah, I didn’t think you would,” said Miss Beckinsale with a smirk. “Come on then, honey. Whip those pants down. Let’s show Miss Crawford what we’re working with here.”
Tyler slid his fingers under the waistband of his boxers, and like a magician preparing the big reveal, he whipped them down, quick as a flash. His giant, footlong rod came shooting out; Cindy’s deep brown eyes nearly popping from their sockets like a cartoon character as it flopped up and down before her. Miss Beckinsale chuckled, a devilish grin stretching across her flawless features as her student’s mother stared listlessly at the massive dong jutting from Tyler’s groin.
“What’s the matter, Miss Crawford? Never seen a dick that big before?”
“Err...w-well, it’s been a while, I must say,” she managed in response, the stunning supermodel utterly dumbfounded by the sheer size of the TA’s wang.
Cindy reached out and took Tyler’s cock her hands, her mouth hanging open as she took in the full extent of its magnitude. Time seemed to stand still as she inspected the huge dong, her hazel peppers taking in every stretch of skim, every thick vein and pulsing capillary. But as anyone with a means of timekeeping would attest, an entire two minutes had passed since the catwalk legend had first wrapped her paws around its girth.
“Whenever you’re ready, Miss Crawford,” said Miss Beckinsale.
“Hmm?” Cindy replied, looking across at the teacher with a comically vacant stare as she held Tyler’s dong in her mits. “Right, yes, sorry,” she said, finally gaining some semblance of lucidity. “My God! Look at the size of this thing!” she said, taking one last scan at Tyler’s cock. “No wonder you’ve been struggling, baby! OK, Kaia, so the first you’re gonna want to do is get that dick nice and wet. The slicker it is, the easier it’ll slide down your throat.”
Cindy and Kaia rose from their seats and squatted next to one another by the side of the desk. Cindy parted her shiny pink lips and fed the dick inside; the gorgeous brown-haired MILF gazing up at Tyler as she started to blow him. Kaia watched on attentively; the teenage model making a pad’s worth of mental notes in her pretty little head as her mother sucked on Tyler’s wang.
Cindy’s lips roamed up and down Tyler’s giant dong; the plump pair accomodating a little more of his monstrous length with each pass and leaving behind thick trails of sticky, wet saliva as they went. Inch and after inch of Tyler’s girthy span disappeared between her lips; his lengthy pipe getting wetter and slicker by the second as she choked it down. With just an inch or two to go, Cindy retrieved Tyler’s sopping cock from her mouth; the brunette relaying some closing instructions to her daughter before she took the final plunge.
“So, baby, the key to deepthroating is to relax your gullet. Once that dickhead pushes past your tonsils, your gag reflex is gonna be doing all it can to stop it from entering your esophagus. It’s up to you to fight that bitch with all you’ve got. Like this.”
Cindy placed her hands on Tyler’s hips and took his cock between her lips once more. This time, however, she plunged right down to the base on the first pass; her lips puckering at his groin as all 12 of his thick, veiny inches vanished into her maw. Kaia’s lips gaped in disbelief; the teen’s pretty little mouth falling slack like a trailer park dweller’s as her mother choken down every inch of Tyler’s mammoth schlong like it was nothing. Even Miss Beckinsale, who had swallowed her TA’s wang more times than she could count, was staring in wonderment at the oral exhibition taking place before her. Cindy kept Tyler’s cock between her lips for some time before finally releasing it, the giant dong slathered it spittle from the tip to the base as it retracted from her maw.
“Wow, mom!” Kaia gushed. “You sure know how to suck a dick! Dad is a lucky guy!”
Cindy chuckled. “Baby, your dad’s dick isn’t anywhere near as big as this one! My talents really are wasted on him.” She looked up at Tyler as she stroked his meaty wang, her sultry gaze indicating that she wanted to do a lot more with his dick in the future than just stick in her mouth. “OK, your turn, sweetie.”
Kaia gulped nervously.
“You’ll be fine, baby,” Cindy added. “Just remember what I told you.”
Kaia wrapped her hands around Tyler’s dong and steered it between her lips. Her pretty head bobbed and dipped at his crotch; the runway model dousing his already spit-slicked rod in yet more slippery, warm spittle as she slurped at his veiny shaft. Kaia reached down to fondle Tyler’s nuts; the weighty, cum-filled orbs rolling around in her hands like big, flesh stress balls as she sucked his mighty dong.
“That’s it, Kaia,” Cindy encouraged. “Play with those balls, baby. You were right about her multitasking, Miss Beckinsale. You sure have taught her well!”
The teacher grinned. “Well, I aim to please, Miss Crawford. And your daughter is a very last learner. Just look how she’s choking down that dick!”
Cindy and Miss Beckinsale watched intently as Kaia sucked down Tyler’s pole; stretches of thick, vein-encrusted cockmeat coming and going as she guzzled his throbbing junk. In almost no time at all, Kaia’s glossy lips were poised mere inches from Tyler’s groin; the A-list student gripping his muscled hips as she reached the home straight.
“Come on, Kaia,” said Miss Beckinsale. “You’ve got this, sweetie!”
“You can do it, baby,” Cindy added. “Just fight that gag reflex and suck it down!”
Kaia braced herself as she went for the final push. She closed her eyes, tears of mascara trickling down her cheeks as she practically forced the last few inches of Tyler’s wang into her heaving gullet. All manner of choking and coughing noises spluttered from her throat, the dark-haired teen battling hard against her stubborn gag reflex; fighting the urge to eject the mighty penis with every ounce of will.
“That’s it, sweetie,” Cindy encouraged. “Nearly there!”
Another inch vanished between Kaia’s lips. Then another. And another. She willed herself to the finish line; the young model pushing on with all her might as Tyler’s massive dong journeyed down her gullet, not stopping until she felt the wispy hair of his neatly trimmed pubic bath tickle her button nose. She eased an eye open and saw nothing but beach-tanned flesh; Tyler’s ab-lined midriff the only thing staring back at her as she held his cock in her mouth. She’d done it. Sucked down that mammoth span of meat like a seasoned sword swallower. All 12 inches of it.
“YES!” Cindy shrieked, gripping her daughter in a bear hug as she released Tyler’s cock, volleys of saliva raining from the shaft as it retracted from her maw. “You did it, Kaia! I’m so proud of you, baby!”
“Thanks...mom,” Kaia replied, her face squished against her mother’s chest as she squeezed her to within an inch of her life.
“Well done, Kaia,” Miss Beckinsale added. “I knew you could do it.”
“Thanks, Miss B,” said Kaia as her mother finally released her from her clutches.
“So, we should probably make this dick go off now, right, Kaia?” Cindy suggested. “We can’t very well leave it like that can we?” she added, watching as Tyler’s cock twitched and spasmed before them; the spit-drenched dong hopping about like it had a mind of its own. “What do you think, Miss Beckinsale? The other moms won’t mind if their appointment is a little delayed, will they?”
“Well, I doubt they’ll be best pleased if they have to wait,” Miss Beckinsale grinned in response. “But if they saw that dick, I’m sure they’d understand!”
“Great! Have you shown Kaia and her friends how to share a dick yet?”
“No, Miss Crawford. I teach that class to my second years.”
“Well then, Kaia, it looks like you’re getting two classes today,” said Cindy. “Just follow my lead, OK, sweetie?”
“OK, mom,” Kaia replied.
From here, Cindy proceeded to talk her young daughter through the ancient art of cock sharing like she was teaching her about the birds and the bees. Though in this instance, the bird was Tyler’s cock and the bees were his big, low hanging balls!
“Let’s start by sharing this thick ol’ shaft,” Cindy declared, grasping Tyler’s meaty wang about halfway along its span. “Just wrap your lips around the side and work them up and down it. Like this.”
Cindy demonstrated, swathing one side of Tyler’s dong with her soft, pillowy lips and guiding them along the shaft like she was playing the harmonica. Kaia joined her and soon mommy and daughter alike were sharing Tyler’s rod like a giant popsicle; their twin sets of pouty pink lips roaming up and down the twitching pole in flawless unison.
“OK, now let’s take care of these balls,” said Cindy, palming Tyler’s weighty scrotum like a sack of gold coins. “You suck one, I’ll suck the other.”
Cindy and Kaia dipped down to get at Tyler’s balls and fed them between their lips; the supermodel and her teenage spawn gobbling away at the large, churning orbs like they were sharing a bag of candies.
“And don’t forget to stroke the shaft while you do it, baby,” Cindy went on, momentarily releasing her designated nut so she could give further instruction.
Soon, two soft hands were venturing up and down the length of his dong, one below the other; their silken mits roaming up and down his shaft and over every vein and capillary along the way.
“OK, keep sucking on those balls, Kaia, while I return to the shaft.”
Cindy fed Tyler’s dick back between her lips and got to sucking; the randy MILF choking down inch after inch of his giant rod while her daughter saw to his balls. Cindy and Kaia shared Tyler’s junk like a tub of Haagen-Dazs; the young model sucking away at each of his heavy, dangling balls in turn, while her mother worked the shaft. Before long, every inch of his genitalia was drenched with spit, from the tip of his dick to the bottom of his sac.
“Right, let’s switch now, baby,” Cindy suggested, retracting Tyler’s dong so Kaia could take over. “Actually, I think I’m gonna…”
Without a single indication of what she was going to do next, Cindy crawled around behind Tyler’s muscled form, parted his butt cheeks and buried her face in his crack. Taken aback by this sudden and unexpected move, Kaia released Tyler’s cock almost involuntarily.
“Mom!” she exclaimed, stroking Tyler’s rod as she peered around his groin, staring in bewilderment as her mother burrowed into his crack and munched on his stripwaxed rear.
Miss Beckinsale chuckled from her seat at the desk. “What’s the matter, Kaia?” she grinned. “No idea your mom was such a slut?”
“Uh uh,” Kaia replied, still looking a little shocked as she returned Tyler’s dick to her mouth.
Cindy’s unexpected foray into the depths of Tyler’s rear might have taken her daughter by surprise, but to the TA himself the excursion was most welcome. In fact, he was loving every second of it; the chiseled stud trembling like a leaf as the mother-daughter combo of stunning supermodels attacked him from both ends.
Behind him, Cindy was holding his ass cheeks apart; her long fingernails digging into his muscled flesh as she tongue fucked his rear. At the front, Kaia was sucking away at his pulsing rod like she hadn’t eaten in days; sliding the lengthy pole down her throat and drooling and slobbering over every stretch that came her way. Finally, and with the handsome TA shaking from head to toe, Cindy emerged from Tyler’s rear, her face red and slicked with spit as she returned to the front to join her daughter.
“Wow! You looked like you enjoyed that, Miss Crawford,” Miss Beckinsale declared, grinning at her fellow MILF from behind her varnished desk.
Cindy suddenly looked a little embarrassed, her already glowing face flushing even further as she knelt back at Tyler’s feet. “Sorry about that, Miss Beckinsale. I don’t know what came over me.”
Tyler grinned. He knew exactly what had come over her (after all, she wasn’t the first woman to lose every ounce of their decorum in his presence), and exactly what would be coming over her next; his massive cock!
“Please, Miss Crawford, don’t apologise,” Miss Beckinsale replied. “I freakin’ loved it! And I think Tyler quite liked it too. Didn’t you, honey?”
“Uh huh,” he groaned, the shredded hunk still not fully recovered from the rampant rectal probing he’d just recieved.
“Actually, I’m starting to feel a little left out over here,” Miss Beckinsale continued, rising from her chair. “You ladies don’t mind if I join you, do you?”
“Not at all, Miss Beckinsale,” Cindy replied. “He’s your TA, after all.”
“Thank you,” the teacher replied, dropping to her knees and sliding her toned frame between the first year student and her A-list mother. “Three heads are better than two, right, Tyler?”
Miss Beckinsale made out with Cindy, then turned and did the same to Kaia. Tyler’s pole twitched as he watched his gorgeous boss lock lips with celebrity mom and daughter alike, tongues jostling every which way as she kissed the two women in turn. Three sets of hands pawed at his genitals; teacher, student and mother alike squeezing his balls and stroking his rod in equal measure as they made out at his feet. By the time they were done, Miss Beckinsale was wearing an interesting mixture of three types of lip gloss; the brown-haired beauty licking her now very sticky pillows as she turned to her TA.
Without further delay, the trio of heads all went for his groin; his dick throbbing like mad as three sets of plump pink lips seized his junk from every angle. Kaia was sucking on his balls; the first year student guzzling at each of the spunk-filled orbs in turn, while Cindy and Miss Beckinsale shared his cock; their soft twin mouths roaming up and down his rod in perfect synchronicity.
Tyler looked down at the three women gathered at his feet and presumed he must have been dreaming. Group blowjobs were a regularity in his profession, but even for someone with a sexual history as colourful as his, this was quite something. By now, the A-list trio were lined up in front of him, passing his cock back and forth between them like a game of pass the parcel. His dick went from Kaia to Miss Beckinsale, then onto Cindy and back again; each woman taking a single, deep plunge on his lengthy rod before passing it onto the next. His dick twitched and spasmed as it was passed from teen to MILF to MILF; MILF to MILF to teen- the three women handing his dick back and forth like an assembly line.
But soon, things started to get a lot less regimented, and before long, the celebrity trio were practically clamouring over one another to get at Tyler’s junk; three pretty mouths jockeying and jostling for position, and licking and sucking at any stretch of pulsing man beef they could reach.
“Hmm, it’s getting a little crowded here, ladies,” said Miss Beckinsale, the British actress currently the meat in a Gerber-Crawford clan sandwich. “Kaia, why don’t you go lick Tyler’s ass while me and your mum share his dick? It’s nice and clean, right, Miss Crawford?”
“Mmhmm,” Miss Crawford replied, the runway legend answering as best she could while Tyler’s mammoth dong throbbed between her lips.
“How do I do it?” asked Kaia.
“It’s easy, sweetie,” said Miss Beckinsale. “Just stick your face in his crack and jam your tongue up his ass. Just like you do to me.”
Cindy carried on sucking away at Tyler’s girthy wang like nothing had been said; the gorgeous supermodel not even batting an eyelid at the revelation that her teenage daughter had been eating her teacher’s ass for extra credit. In fairness, she had Tyler’s lengthy span lodged too far down her throat to object to much of anything.
Kaia circled around behind Tyler, just as her mom had done earlier and spread his ass cheeks apart. She peered into his crack- the waxed crevice a mess of saliva and smeared lipgloss from her mother’s earlier jaunt- the freshman taking but a single moment’s pause before sinking into his darkest depths.
“Uhh!” Tyler groaned, as Kaia stuck her face in his ass, her tongue shooting out and plunging into his rectum.
By now, he was shaking from head to foot; the muscled TA getting shelled from all angles by a trio of foes and their endless array of oral artillery. Miss Beckinsale was working his dick; her full, shiny lips roaming up and down the lengthy wang from tip to base. Cindy was sucking his balls; the brown-haired beauty dousing each of the brewing spunk tanks in turn in oodles upon oodles of spittle. And Kaia was tonguing his ass; the first year student rooting around in his anal cavity like she was searching for loose change.
This went on for some time. A line of students and their impatient mothers started to form outside Miss Beckinsale’s classroom door, some of which had been waiting on their appointments with the oral expert for close to an hour. Back inside the room, the three women were showing no signs of slowing down. By this stage, student, mother and teacher alike were circling Tyler’s body like planets in orbit, the randy trio running a line from his dick, to his balls, to his ass; all three of the A-list beauties taking turns to choke down his rod, gobble at his nuts and feast on his stripwaxed rear.
Tyler had managed to hold his own throughout the whole ordeal. Indeed, the handsome TA had withstood countless assaults on every one of his pleasure points; a ruthless campaign of three pronged attacks that would have seen lesser mortals blowing their beans in a matter of moments. But after 60+ minutes of threeway dick sharing, his stout resistance was starting to wane.
By now, Miss Beckinsale had her face buried in his ass, while Kaia and Cindy worked their twin sets of full pink lips up and down his cock; the lengthy pole seeming to twitch and spasm more violently with every pass. Sensing that Tyler’s orgasm was close at hand, Cindy released his dong from between her lips and addressed her nearby daughter.
“I think he’s ready to cum, Kaia,” she declared, stroking Tyler’s rod and feeling it throb and pulse in her hands.
The mere mention of her TA’s ejaculate pricked Miss Beckinsale’s ears and she surfaced from the depths of his crack in almost comical style, the English actress circling around to rejoin her two companions in the blink of an eye.
“That true, baby?” she asked, gazing up at Tyler as she slotted in between Kaia and Cindy. “You gonna cum for us, Tyler? You gonna streak these faces with all that boiling hot nut?”
Tyler pulled himself off as three women pressed their faces together. Tongues darted every which way; brushing against one another and flicking at his drooling tip. Miss Beckinsale reached up and fondled his swelling balls. Cindy stuck a finger in her mouth and sucked it seductively, before reaching around and jamming it up his tuchus.
“Come on, honey,” she purred as he fingered his rear. “Give us that cum. Shoot that gooey load over these pretty fucking faces!”
Tyler tugged at his dick so violently he nearly yanked it straight from his groin; the giant dong throbbing and pulsing like nobody’s business as he jerked himself off. Tongues lapped at his dickhole. A finger plunged into the depths of his rectum and tickled his prostate. Long, carefully filed fingertips grazed the skin of his nutsack as a multitude of digits squeezed his heaving balls.
He held off until he could no longer; the muscled TA emitting what was quite possibly the most violent blast he’d ever shot (no small feat, considering he spewed his wad at least four times every day); a gooey load of piping, off-white semen jetting from his tip and splattering across all three of the assembled faces in equal measure. By the time he was done, the trio of women were drenched in his nut; his eruption so copious he’d been able to give all three of the A-list stars a facial that most men could only dream of. Thick ropes streaked their faces, clung to their eyelashes and messed their shiny hair and expensive clothing.
“Wow, Kaia! Your school is incredible!” Cindy exclaimed, licking a glob of spunk from her upper lip. “No wonder you wanted to go here so bad!”
“Mmhmm,” Kaia grinned. “Who are we seeing next, mom?”
“Let’s see,” Cindy replied, consulting her itinerary. “Miss Wood. Lesbian 101. Sounds interesting.”
All three women rose to their feet.
“Thank you, Miss Beckinsale,” said Cindy, giving her daughter’s teacher a hug. “This has been very eye opening,” she added; a rather ironic statement given that one of her pretty brown peepers was now glued shut with cum!
“My pleasure, Miss Crawford. I hope your next appointment is as eventful as this one.” Miss Beckinsale checked a sheet of paper on her desk. “Kaia, send Chloe and her mom in on your way out, would you?” She looked across at Tyler. “And you- you stay right there. I have a feeling you may be needed again!”
*
Meanwhile, down the hall in Room 69K, Amy Adams had just finished her meeting with Olivia Holt and her mother, when Maude Apatow and her mom, Leslie Mann, came strolling through the doorway.
“Hi, Maude,” said Miss Adams, smiling warmly at her third year student as she entered the room. “Miss Mann, it’s great to meet you,” she added, rising from her seat and shaking Leslie’s hand.
“Great to meet you too, Miss Adams. And, please, call me Leslie.”
“Certainly, Leslie.” Miss Adams returned to her seat. Leslie and Maude sat opposite. “Thank you for coming in this evening. So, I’d like to give you an update, if I may, on Maude’s progress in my class, Anal 301.”
“Please. Go right ahead, Miss Adams.”
“OK. Well, I’d like to start, Leslie, by saying how fond I am of your daughter. She’s one of my most diligent and attentive students. Her essays are nothing short of exemplary and she’s well on course for an A in the written segment of the module.”
“Wow!” said Leslie, turning to her daughter. “Well done, sweetie.”
“However, I’m afraid to say that her showing in practical assignments falls some way short of her success in the written modules.”
“Oh, dear,” Leslie replied, suddenly looking rather concerned. “In what way?”
“Well, Leslie, I’m sure Maude would be the first to admit that she’s been struggling a little with the penetrative module of the course. Isn’t that right, honey?”
Maude looked down sheepishly at the classroom floor. “Yes, Miss Adams.”
“Now, there’s nothing to be embarrassed about, Maude,” Miss Adams declared. “Lots of women have their share of difficulties with anal when they first start doing it. I know I did.”
“Me too,” Leslie added. “It’s fine, baby,” she added, giving her daughter a reassuring pat on the thigh. “It’s nothing to be ashamed of. Right, Miss Adams?”
“Absolutely, Leslie. Absolutely.”
“But, hold on a second,” Leslie went on, looking a little confused. “Maude showed me her report card when we went out to dinner last week, and it said she was on course for an A.”
“Yes, Leslie, she is currently near the top of the class for this particular module. However, I’m afraid that grade is based solely on her written assignments and certain other...activities she has completed for extra credit.” Miss Adams did her best to stifle a grin as she explained. “And it is my duty to tell you, that if Maude fails to complete the practical exam in two weeks time, she will average out at a D for the semester.”
“Oh, God,” Leslie gasped, the fair-haired actress reacting to the announcement like it was news of a terminal illness.
“Now, Maude and I have been working closely with one another, both during class time and in private study sessions, to try and rectify this problem, and have tried a number of different techniques to help...ease the entry. So to speak.”
“Such as?’
“Well, we’ve tried fingers, haven’t we, Maude? Tongues. Toys. In fact, your daughter has taken a number of different items up her butt with considerable ease. Buttplugs. Anal beads. But when it comes to penetration, that cute little asshole just clams right up. Doesn’t it, sweetie?”
“Yes, Miss Adams,” Maude replied, still looking a little embarrassed as her mother and teacher discussed her sodomic shortcomings.
“Hmm, do you think it could be an arousal issue?” Leslie asked.
“I don’t think so, Leslie. It’s an avenue we’ve explored, isn’t it, Maude? But, I went down on your daughter for close to an hour the other night and, I’ve gotta tell you, Leslie, I was nearly drowning in her juices by the end! But then, when my TA tried to enter, her asshole repelled his dick like the Red Army! It’s size, I fear, that is the issue.” She looked at Maude. “It’s Aaron’s dick. It’s just too big, isn’t it, sweetie?”
“Yes, ma’am.”
“I see,” said Leslie. “So would it not make sense for Maude to try and take a smaller dick first? Rather than going straight for the big ones?”
Miss Adams chuckled. “There are no smaller dicks, Leslie. Every TA at this school is incredibly well hung. Sex with lesser endowed males isn’t something we encourage here at SVSSG, but if Maude wants to tackle a smaller penis on her own time, then that is entirely up to her. But taking a cock up your ass is a mostly mental endeavour, and all I think Maude needs is a little more support. Don’t get me wrong, I have been assisting her throughout the semester in every way I know how. As have her friends. However, I think a show of support from those closest to her could be the final piece of the jigsaw.”
“You mean me, Miss Adams?”
“Yes, Leslie, I do. I truly believe that all Maude requires is a little encouragement from someone dear to heart to get her over that final hump, and if she had a close family member, such as yourself, to walk her through the act of anal sex, she’d be taking dicks up that peachy little ass of hers left, right and centre! Now, obviously I can’t allow you to assist during class time, but you’re more than welcome to help Maude in her own time as much as you both desire. And since we’re all here now and my assistant, Aaron, is waiting just outside that door, this might be an opportune time to start.”
Leslie looked over at her daughter. “What do you think, baby? Do you think it would help if I was there to assist you?”
“I don’t know, mom,” Maude replied. “But if Miss Adams says so, then I think we should give it a shot.”
“OK, honey. Let’s do that.”
“Brilliant!” said Miss Adams. “Trust me, Maude. This is just what you need. Shall I bring out my TA?”
“Mmhmm,” mother and daughter replied in unison.
Miss Adams grinned. “Aaron!”
The door swung open and Aaron strolled inside; the handsome young man strutting across the classroom with a confident swagger only a man with a 10 inch slab of meat tucked away in his undies can possess.
“Here he is, ladies. Maude, why don’t you start by whipping down those boxers? Let’s show your mom that cock!”
Maude rose from her chair and knelt at Aaron’s feet. She clutched two handfuls of his white cotton undies and tugged them down, the TA’s soft, though immensely long prick falling free and dangling pendulously between his thighs.
“Oh my God! He’s huge!” Leslie exclaimed, blue eyes bulging upon sight of his dong. “He’s even bigger than that guy I ordered for us while your father was out of town!”
“Get that dick in your mouth, Maude,” said Miss Adams from behind her desk. “Let’s get that thing nice and hard. I’m sure you already know this, Leslie, but your daughter is a fantastic cocksucker.”
“Oh, I do, Miss Adams. I do. She got an A+ in Blowjob 101, don’t you know?”
“I can believe it. Miss Beckinsale taught her well.”
Maude gripped Aaron’s cock in her hands (even in its flaccid state it, his wang was still long enough to fill two mits with room to spare) and fed the crown between her lips. She sucked at the big pink head and stroked the lengthy shaft, feeling the limp prick stiffen and grow in her mouth and hands as she worked it over.
Leslie watched on from her seat at the desk; the blonde MILF gazing longingly at Aaron’s rod as Maude released it from her lips, the giant member already vastly outmeasuring her husband’s dick despite having yet to reach its full rigidity.
“Here, why don’t I give you a hand with that, baby?” she said, squatting down beside her daughter.
Maude was, in fact, doing a fine job on her own. By this stage she was sucking away at Aaron’s balls while she stroked his cock, the thick rod seeming to get harder and longer with each pass of her silken hand. But Aaron had easily the biggest dick Leslie had ever seen, and she simply coudn’t let the opportunity to suck such a large hunk of meat pass her by.
She guided the ever swelling head between her lips and worked them along the shaft; the girthy rod growing and growing to the point that she was wondering if it would ever stop. Finally, after what felt like aeons had passed, Aaron’s dick had grown to its full 10 inches, the veiny prong throbbing between her lips and against her tongue as it reached its final mass. She retracted it from her maw, stroking the shaft as she beheld the mammoth schlong in all its full, erect glory.
“OK, let’s lube this thing up,” said Leslie, jerking the massive member with both her dexterous hands.
Miss Adams fetched her box of sex toys from under her desk- a treasure trove of exotic marital aids that Maude was already more than fimiliar with- and took out a bottle of lube.
“Here you are, Leslie,” she said, sliding the bottle across her desk, her fellow MILF catching it in her painty paw as it tumbled over the edge.
“Thank you, Miss Adams.”
Leslie flicked open the cap and drizzled a long trail of the clear, slick goo across Aaron’s rock hard pole. She set the bottle down on the carpet and gripped his dick at the base, gazing up at the TA she stroked his dick, greasing the mighty wang from tip to base.
“There,” she said, inspecting the rod from all angles as she admired her handiwork. “That’ll do nicely.”
“Here, Maude, why don’t you bend over my desk,” Miss Adams suggested as she rose from her seat.
“Great idea, Miss Adams,” Leslie agreed. She turned to her daughter. “Take those clothes off, baby, and get in position.”
Maude stood and pulled off her top, baring her perky, young titties. Then, she inched down her frayed denim short shorts, removing her skimpy white cotton panties along with them. She leant over the edge of the teacher’s desk, gazing nervously over her shoulder as Aaron stroked his massive, greased up wang. Miss Adams squeezed a glob of lube onto Maude’s asshole and smeared it around with her dexterous fingers.
“Ready, Aaron?” she asked, standing beside her student and spreading her student’s ass cheeks for the coming invasion.
“Always,” he replied as he stepped up to the plate, long flesh bat ready to swing.
Leslie leant over the desk opposite her daughter, looking deep into her eyes as she stroked her glossy brown hair.
“Just relax those glutes, OK, honey. Trust me, you’re going to love it.”
Aaron pressed the tip of his wang against Maude’s puckered pink sphincter and pushed; the skittish senior yelping in pain as the girthy tip split her asshole open.
“It’s OK, baby. It’s OK,” said Leslie, clasping her daughter’s hand. “Deep breaths, OK, sweetie?”
Maude nodded, blowing out sharp, ragged breaths like a birthing woman undergoing contractions. Aaron continued to push, placing a hand on the small of her back as he fed his turgid schlong slowly, (literally) agonisingly so, into the student’s rectum. Maude’s asshole fought the giant dong for every solitary centimetre, and despite a good deal of exertion on his part, Aaron had yet to fit even a single inch through the stubborn pink slot.
“Hmm, I think we’re gonna need a little more lube,” Miss Adams declared, clocking the minimal progress of her TA’s thick wang.
She gathered the bottle and gave it a squeeze; the tawny starlet damn near draining the entire thing as she soaked Aaron’s dong in grease. She ran her hand up and down the shaft; Aaron’s member so drenched in the sticky goo that her hand glided from the head to the root and back in a fraction of a second. The extra dousing had helped but only to a point, and it still took every ounce of Aaron’s considerable musculature to guide his length inside. Finally, the first inch slipped inside, then the second, then the third; every span of thick, veiny meat causing the third year student to squawk and squeal anew as it slid into her rectum.
Aaron began to buck his hips, working his dick back and forth and guiding an extra inch into the senior’s virgin hole with every motion. Maude continued to emit all manner of ear piercing sounds; her high-pitched yelps sounding less like pain and more like pleasure with each passing second as Aaron’s wang started to ream her backdoor. Before long, he was pounding away at her maiden rear with little mercy, this thick, swollen cockhead tunneling deeper into her anal passage with each new thrust.
“You’re doing great there, Maude,” said Miss Adams, looking back at her student as Aaron’s girthy rod surged through her virgin tunnel. “Just a few more inches to go.”
“Oh, wow! I’m so proud of you, sweetie,” Leslie added, kissing the back of her daughter's hand. “Just look how well you’re taking that dick! How does it feel, baby?”
“It feels amazing, mom!” Maude replied, her pained expression now morphed into one of rapturous ecstasy as Aaron’s giant dong drilled her rear end. “It feels fucking amazing!”
Aaron gripped Maude’s hips, holding the slender brunette in place as he pounded her from behind. His balls swung back and forth, the heavy, cum-filled orbs slapping against the student's clit as he plowed her tight pink ass. Another inch vanished into her rectum. Then another. Then another. Soon, he was hitting it ballsdeep; the chiseled young stud driving his dick right to the hilt, his bulging crown mining into the darkest depths of her colon with each pass.
“Goddamn, Maude!” Miss Adams exclaimed. “You’ve taken the whole thing!”
“Oh my god! You hear that, baby?” Leslie asked. “You’ve got every inch of that big, fat cock in your tight little ass!”
She certainly did. In fact, by this stage, Aaron’s muscled pelvis was clapping against her asscheeks with each pass, the force of each thrust making her entire body shake as he buried his cock in her peachy, round rear.
“Oh, fuck!” Muade squealed. “It’s so fucking deep!”
“It is, baby!” Leslie purred in response. “It’s BALLS freakin’ deep! You gonna cum, sweetie?”
“YES! Yes, mom, I’m gonna fucking cum!”
“Cum then, baby. Scream this fucking school down. Do it, baby. Cum for mommy!”
No further encouragement was needed. Aaron sunk his dick into Maude’s murky depths one final time, sparking an intense, bone rattling orgasm that made, not only Miss Adams’ desk, but the entire room rumble, like a subway train was passing overhead.
“UUUHHH! FUUUCCCKKK!!!” she screamed, a deep, guttural cry that surged from her throat like a lion’s roar.
Aaron, Miss Adams and even Leslie exchanged glances; the trio seemingly unaware that a young lady so lithe and petite could even emit such a sound.
“See, Maude,” said Miss Adams. “Didn’t we tell you you’d love it?” She looked up at Aaron. “Now pull that dick out, baby. I wanna taste her ass right off of that cock!”
“Mmm, me too,” Leslie added, scurrying around to the other side of the desk and squatting beside her daughter.
Soon, Maude’s backside had two gorgeous, mature faces flanking it from either side. Aaron prized his dick from the vice-like grip of her snug pink asshole and plunged it into each of the waiting mouths in turn. He started with Leslie; the handsome TA steering his dong straight into her gaping pink maw and giving her a taste of her daughter’s ass right off of his rod. Leslie sucked at his big, fat cock like a child with a popsicle; the pretty blonde MILF slurping up her offspring’s juices until it was almost sparkling clean. Then, she passed it into Miss Adams, allowing the A-list teacher to mop up the last of the fluids, until Aaron’s wang was practically glistening with a cocktail of saliva.
“What do you say we show her some more positions now, Miss Adams?” Leslie suggested, grinning naughtily as she stroked Aaron’s dripping wang.
“Good idea, Leslie,” Miss Adams replied. She reached around and gave Aaron a hearty slap on the butt. “Lay down.”
Aaron sprawled out on his back across the desk.
“OK, Maude, let’s try a little cowgirl,” Miss Adams went on. “This is a great position, ‘cause you get to be in control.”
Maude climbed up onto the desk and straddled Aaron’s frame.
“Just aim that dick at your asshole, sweetie, and lower yourself onto it.”
Maude gripped Aaron’s dick at the base and pointed the thick, round head at her greedy, winking asshole. She sunk down onto his cock, her sphincter stretching as it slipped inside.
“Mmm!” she groaned as it entered her; the bulging pink crown venturing up into her rectum as she lowered herself on his rod.
“Hmmhmm,” Leslie chuckled, grinning at her daughter’s satisfied whine and the look of ecstasy etched across her face. “You’re starting to like that, aren’t you, baby?”
“Uh huh,” Maude groaned, bringing a hand down to tease her clit as she rocked slowly atop Aaron’s muscled form.
“This boy sure knows how to work that rod,” Leslie declared, unbuttoning her blazer and slipping it off. “I wonder what he’s like with his tongue.”
With that, Leslie removed the rest of her clothing and hopped up onto the desk. She threw her leg over Aaron’s torso and perched down on his face. Aaron knew just what to do next. Leslie’s peachy, round buns had barely alighted upon his person before he shot out his tongue; the burly young hunk sinking it right up into her puckered asshole.
“Ohh, fuck!” Leslie gasped, eyes popping; the fair-haired actress evidently unprepared for the chiseled TA to devour her so greedily right off the bat.
But he wasn’t done yet and no sooner had his tongue plunged into her rectum, was he wagging it around in there like a deadly viper; the chiseled TA rooting around in her juicy rump like he was searching for his keys.
“Ohh! Ohh, yes!” Leslie purred, her voice aquiver. “Yeah, baby, just like that!” She reached around and gripped a handful of his hair, shoving his face so deep into her crack that he couldn’t have escaped if his life depended on it (and, who knows, maybe it did). “Get up in that ass like you mean it!”
While he ate Leslie’s ass, Maude continued to ride his muscled frame, her tight, gripping asshole venturing further down his girthy shaft with each pass, until her supple, round buns were clattering against her thighs. But it didn’t end there, and as if anally probing two members of the same celebrity family with different parts of his anatomy wasn’t enough, Aaron soon felt the attentions of a third unrelated, though equally gorgeous and famous woman, as Miss Adams squatted between his thighs and started sucking on his balls!
Aaron was on cloud nine; the young hunk practically buried alive under a pile of A-list beauties and enjoying every second of it. He grasped Leslie’s shapely MILF ass with all his might; his strong fingers digging into the creamy white orbs as he tongued at her anus, scoffing at her delicious, round rump like it was his last meal. Meanwhile, Maude was hopping and bouncing atop his shredded form like there was no tomorrow; the horny senior riding his massive dong like a cowgirl at a rodeo. Then, Aaron reached down and gripped Maude’s waist, holding the brunette in place as he bucked his hips and drove his dong up into her ass.
“Uhh, JESUS!” she cried, reaching down to knead her clit as he threw his dick up into her; the mighty member snaking deep into her colon with each pass.
“Yeah, that’s it, honey. Play with your pussy like that,” Leslie cooed, mirroring her daughter’s actions with some strumming of her own; the blonde beauty kneading her pulsing bud as she perched on Aaron’s face. “Make yourself cum, baby. I want us both to get off together.”
Miss Adams circled around to the side of her desk, making out with mother and daughter alike as they squatted over her TA’s brawny young body.
“Yeah, come on, ladies,” she purred, fixing both women in turn with intense, simmering eye contact. “Shoot those loads! Drench that stud in those luscious lady liquids!”
Leslie and Maude thrummed themselves like mad, their almost genetically identical bodies trembling all over as huge, veiny cocks and skilled, wet tongues alike burrowed into their related rectums. Then, in what can only be described as a mother-daughter bonding experience like no other, both women came; emitting harsh, deafening screams as twin jets of clear, wet girlspunk blasted from their twats, drencing Aaron and each other in a deluge of frizzling fluids.
“Uh, holy fuck!” both women sighed in panting, gasping unison as they climbed down from Aaron’s body, leaving the handsome TA half drowned in a sea of slippery squirt juice.
“Damn, girls!” Miss Adams exclaimed. “That was quite a show! You ladies really are close, aren’t you? Me and my mom just eat ice cream and watch movies together!”
Leslie and Maude laughed as they approached the auburn beauty and flanked her from either side. Two sets of soft, feminine hands roamed across Miss Adams’ toned body as she found herself sandwiched between the third year scholar and her hot, A-list mother. She and Maude locked lips as the student undid her blazer, Leslie kissing her neck as she slid it down her arms. Miss Adams turned her head and made out with Leslie, Maude unbuttoning her blouse and unzipping her pants.
Aaron watched on from the desk, stroking his squirt-drenched cock as he watched the mother-daughter duo undress his gorgeous boss; his brain nearly bursting as he tried to discern just what wondrous, fourway delights were coming his way next. By now, Miss Adams was entirely nude, Leslie and Maude trailing licks and kisses across her naked body.
“Bend over the desk. Leslie,” she said. “I’ve got an idea.”
Aaron climbed down from the desk and Leslie took his place; squirt juices further soaking her torso as she leant over the wet surface. Miss Adams clambered up next; kneeling on the edge of the desk and setting her ass down on top of Leslie’s. Maude, the youngest and most supple of the three, went up last; completing the trifecta with a third set of peachy, round buns, perched atop her teacher and mother like a stack of pancakes, squirt juices trickling over all three bodies like a jug of maple syrup.
Aaron slathered his dick in a further dose of lube and looked across at the triple decker sandwich of gorgeous A-list women stacked up before him; all three of them fixing him with all manner of sultry stares, giggling and making out with one another, in wait of his greased up wang. He started at the bottom and worked his way up. He poked his crown against Leslie’s asshole and entered; guiding the bulbous helmet into her experienced rectum with far greater ease than he had her daughter.
And speaking of her daughter, she was next to experience the wonders of his sexual prowess when he lent forward and buried his face in her ass; the handsome TA tonguing at Maude’s ass while he fucked her mom. Moans and groans chorused up and down the stack of celebs from top to bottom; the lion’s share coming from Leslie, as Aaron worked his thick, lengthy schlong back and forth in her rectum, drilling harder and deeper into her anal cavity with each pass.
Then he moved onto Miss Adams. Her ass was positioned a little too high for his tall frame to reach, but no problem- he pulled up her desk chair and climbed aboard. He squatted slightly until he found the perfect height, pointed his dick against her round, winking anus and steered it inside. His raised stance didn’t allow for the smoothness of rhythm of his previous position, but he plowed away at Miss Adams’ shapely MILF ass as best he could; sinking his bulging pink crown into her darkest recesses with every motion.
The seat groaned and creaked beneath him as he pounded his boss’ ass, and Aaron feared it may give way entirely, leaving him on the receiving end of a rather painful bedroom related injury as his muscled form went tumbling to the ground. But the chair held strong, its sturdy frame capable of withstanding not only the TAs massive, sinewy bulk, but also his practiced sexual manoeuvres like it had been crafted with that purpose in mind.
Then, as he moved up to the top tier, Aaron’s positioning grew bolder still. He climbed up onto the desk, squatting legs spread over the stack of women, his bare feet teetering on each edge as he pressed his dickhead against Maude’s fledgling rear and guided it in. This position, precarious though it may have been, allowed for a greater range of motion, and Aaron leant over the pile of women, hammering his dick down into Maude’s back entrance with little restraint. Coos and groans continued to chorus beneath him, the sounds and sights of his tawny boss making out with student and student’s mother alike, causing his dick to twitch and throb in the depths of Maude’s bowels.
“Fuck, I’m gonna cum!” he blurted it out, virtually bellowing it into Maude’s ear as he swathed her slender frame.
“Wait, wait!” barked Miss Adams from between her two companions. “Not in there!”
Aaron pulled out of Maude’s rear and practically leapt down off the table. The women came down after him one by one, and Maude took her mother’s position on the desk.
“Do it over her ass!” Miss Adams ordered, pointing down at Maude’s peachy rear as it stuck out over the edge of the desk.
Aaron was back inside the student’s rump in the blink of an eye, pounding away at her budding backdoor like there was no tomorrow. Meanwhile, Leslie and Miss Adams had circled around behind him and squatted beside one another. They nestled together and shot out their tongues; the gorgeous MILF duo taking turns to lick at Aaron’s stripwaxed rear, meeting each counterthrust with a wet plunge into the depths of his rectum.
Having just spent the better part of an hour plowing away at not one, not two, but three tight, A-list butts, the tandem tonguing of his own silky smooth rear proved to be a bridge too far. Aaron prized his dick from Maude’s snug pink asshole and started jerking, Leslie and Miss Adams still lapping at his anus as he prepared to plaster the student’s bottom with his seed.
His hand roamed up and down the length of his dong at a mile a minute; two slick red tongues alternating deep pases into his backside as he pulled himself off. Leslie, Miss Adams; Leslie, Miss Adams- their moist flesh seeming to sink further into his anal cavity and tickle more of his intimate areas each time. His dick pumped and pulsed in his trembling hands, the young stud violently beating his meat until finally it went off.
“URRRGGGHHH!” he roared as his dick erupted; a copious wad of gooey spunk spewing from his tip and hitting a lot more than its intended target as it splattered across his female counterpart.
Aaron’s load had sprayed across Maude’s ass, make no mistake of that. The thing was, it had doused nigh on every other stretch of a smooth, alabaster skin along with it; thick ropes of the stuff travelling all the way up her back and even peaking at the long brown strands of her hair. In short, he’d made one hell of a mess, but never fear, Leslie and Miss Adams were on hand to clean it up. They lapped up every last ounce of spunk from the student’s frame in double quick time, sharing it out with a long, sloppy kiss before gulping it down.
“Oh my god! This school is amazing!” Leslie declared, licking her cum-smeared lips. “I can’t believe I let Judd come to the last two parent-teacher nights! What was I thinking?!”
Miss Adams chuckled. “Yeah, I remember Mr Apatow coming along to this last year. I must say though, Leslie, you’re a lot more fun!”
“It was incredible!” Leslie replied. “I hope Iris wants to come here too, so I can come back next year!”
“Me too!” Maude added. “Does this school have a teacher-sister night too, Miss Adams?”
Miss Adams laughed. “Not that I know of, Maude. But I’m sure Principal Vergara wouldn’t object if you wanted to come along too. I know Aaron here certainly wouldn't. Would you, baby?”
“Hmm?” Aaron asked with all the strength he could muster, the muscled TA looking only moderately conscious as he slumped back in the teacher’s chair.
“Aww! He’s a little tired, bless him,” Miss Adams grinned. “You better wake up, honey. Leslie here was only our second parent of the evening.” Aaron gulped nervously as she continued. “We’ve got another eight to come yet!”
End of Chapter 7