πŸ“š simon b. 02 - Part 3 of 4
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EROTIC COUPLINGS

Simon Bk 02 Ch 03

Simon Bk 02 Ch 03

by rosis
19 min read
4.36 (818 views)
adultfiction
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"Hey, you!"

Simon turned to see a tall woman separate herself from the shadows as he left the Phi Epsilon Tau house. As she got closer, he noticed the birthmark on her upper lip; it was Applicant A from the competition earlier. "Uh, yeah?"

The brown-haired young woman stepped up, towering over him at her height of almost 6 feet. "You're 'Cockboy', right? I couldn't make out much with the mask on, but you seem the right size."

"Uh, yeah, I'm Simon." He held out his hand with a smile.

"You owe me."

He dropped his hand. "I do?"

"Getting into this sorority would have opened a lot of doors for me, guy, and then you blow two loads inside that shapeless Filipino chick? I mean, the hot redheaded lesbian, sure, but why not me? Am I not sexy?"

Simon ran his eyes up the curvy girl's tall form in her t-shirt and tight jeans. "Yeah, you totally are...sorry, but the redhead really had me going, the other girl was right after her, and she was really tight, so it just kinda happened."

"So if I'd have been after the redhead...?"

"Then you'd probably have won. I'm sorry it didn't work out, miss...?"

She sighed. "Muriel." As he offered his hand again, she shook it.

"So what do I owe you?" he asked as he gave her another winning smile.

She shuffled her feet in her pink All-Stars. "Um...a load in my cooch?"

He rubbed at his crotch and winced. "It's sore...not sure it'll be possible tonight."

"My place is close...you ever have someone give you a boob job?"

"Yeah...you want to do that? It might help."

And sure enough, once they were alone, Muriel was able to revive his member by surrounding it with her saliva-slicked D-cups. After that, she lay back on her bed and opened her arms and legs for the slim young man. Simon, reminded of his tall, curvy mother, enthusiastically fucked the young woman for half an hour, giving her three orgasms before he filled her unknowingly, artificially-fertile depths with his last ejaculation of the night and pushing her into her fourth release.

"Guhh...huhh..." she moaned and shook as she felt Simon's hot load soak into her vulnerable reproductive system. "Yes, that's what I needed..."

"I'm really tired..."

She wrapped her arms around him. "You can sleep, just like this, Cockboy."

And he did, his half-hard member sealing his seed inside her.

---

Simon woke to find his cock inside Muriel's hot mouth as her oral ministrations returned him to full girth. "What time is it?" She pointed to her clock as she sucked. Then he realized: "Oh, wait, it's Sunday."

She turned and presented her plush ass to him. Mostly recovered from the marathon sex the previous night, he was able to hold off for twenty minutes before he grunted and filled her primed baby chamber with another large load of swimmers. "UGH! Ohh..."

"HHGG!" she screamed into her sheets as she came hard.

He carefully pulled out and gathered his clothes. "Thanks, Muriel...I should head home."

She awkwardly grabbed at her phone. "Wait...gimme your number?"

Simon smiled...another helper!

---

The next day, Vesper texted Simon that her period had started, so she had no sex drive, but suggested that he go make himself available to Stevie, even sending him the curvy brunette's schedule. He made sure to be sweeping outside one of her classes as it got out.

"Simon! Fancy seeing you here."

He stopped sweeping and looked down at his coveralls. "Fancy?"

Stevie blinked. "It's...just a saying..."

"Oh."

She touched his arm. "Ves is on her period...a vigorous young man like yourself, you're probably backed up, right?"

"Well, yeah, I guess." He remembered Vesper telling him to not be too eager.

She sighed. "I'm offering my services, Simon...I have some free time right now if you can take a break."

He gave her expansive chest a glance. "Sure...the green room should be empty right now."

He locked the door behind as Stevie pulled off her yoga pants, panties, t-shirt, and bra before laying back on the couch that he'd fucked Vesper on several times. She kept her eyes on the slim young man's crotch as he pulled off his coveralls to reveal his nine inches of steel-hard phallus. "Jesus, look at that thing," she breathed as she stroked at her wet pussy lips. She'd been super horny for him since he'd fucked the twins at the sorority house. Then she shook her head and grabbed a condom package from her shoulderpack. "You have to wear this."

Vesper had said that he should use the condoms she'd given him but he couldn't switch them while Stevie was watching, so he rolled the thicker prophylactic down his member. "I can go down on you..." he offered.

"I'm so fucking wet right now," she said as she schlicked two fingers inside herself. "Just fuck me!"

She was well-lubricated but tight, so it took a few tries before he got all of himself inside her.

"Ughfuuck..." she moaned as she felt him deeper inside her body than anyone had ever been. "Easy...go slow..." Despite her promiscuous nature, she actually hadn't had sex in months, choosing instead to concentrate on her studies. As Simon leisurely withdrew and then pushed back in, she moaned, "Ohh shit...Vesper's a lucky woman..."

"Let's not talk about her right now." Simon started thrusting harder.

"Ohh...okay...fuuuck...oohh fuuuuck..." Then she was cumming, her mouth open and her eyes unseeing.

Simon continued to thrust. He wasn't close to his own release due to the thickness of the condom Stevie had given him, so he concentrated on making her feel good. He took one of the pronounced nipples of her D-cups between his lips and sucked.

"Fuuuck! FUUUCKKK!" she screamed as she came harder, her body shaking. Finally, she lay back, unmoving.

"Stevie?" He gave her a few more thrusts, but determined that she'd passed out. He withdrew, rolled the thick condom off, and replaced it with one of the ones that Vesper had given him, since those were thinner and would feel better. Then he turned the curvy brunette on her side, raised one of her legs over his shoulder, and thrust back into her sopping depths. Yes, that definitely felt much better.

"Uhh..." she moaned and looked up at the thin young man with half-lidded eyes as he sawed into her. "That was...holy shit..." She reached down to confirm that he still had a condom on. "You fuck machine..."

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"Huff huff!" Simon huffed as he thrust harder into Stevie's nubile body. He was going to cum soon.

She moved her fingers to her prominent clit. "C'mon...c'mon, fuck me..." Her other hand went to squeeze one of her hard nipples.

"Nnh..."

Her eyes widened...he was going to cum! She squeezed her nipple harder as her other hand rubbed at her love bean.

"Nnhh..."

She could feel his cock swelling inside her as he thrust hard. "Ohh...yess..."

"NNNHH...UHH!"

"Yessss...NGH! Unhh!" She came hard with him, her pussy squeezing his cock as if it was trying to wring all of the seed from it. "Ohhh..." She shook as she felt his cock pulse inside of her, his hot seed blocked by the condom.

Or so she thought. As Simon's load filled the reservoir of the trick rubber, the pressure pushed several drops through the tiny holes that had been poked there. As he thrust as deeply inside Stevie's hot depths as he could, those drops soaked into the spasming entrance of her womb. After being squished against her cervix by his repeated thrusts, some of his seed slipped inside.

For the first time in her life, the ignorant, curvy brunette had dangerous sperm inside of her pristine womb. She moaned as her orgasm calmed down, her body feeling sluggish and warm. She moaned again when Simon pulled out, but otherwise didn't care about anything at that moment.

Simon once again noticed several drops of his stuff on the outside of the condom...he'd somehow put it on wrong again! However, he hadn't made a mess, so he wrapped the defective rubber up with some tissues and slipped it into his coveralls' pocket.

"This is our secret, right, Simon?" At his nod, she asked, "Can I have your phone number?"

He smiled.

---

Vesper grinned as she read Simon's report. She and her frenemy Stevie were at odds in more ways than one...while the slim blonde was currently on her period, the voluptuous brunette had hit the midpoint between hers and was currently fertile as a turtle! She giggled at the thought of Simon's no-doubt-potent sperm swimming deeper inside the stupid whore. She almost decided to masturbate, but then a cramp hit. *See if u can do her again tonight, jumbo shrimp,* she texted him.

---

"Bit small," Stevie commented as she stepped into Simon's apartment.

"All I can afford."

She dropped her shoulderbag inside the door and nibbled her lower lip. "Soo...what can you tell me about pledge night?"

"Helen told me it was a secret."

"I was there when she said that, remember?"

"Oh, right...well, then I guess I can say." He told her about being restrained in the chair while the three young women rode his chemically-enhanced cock.

Stevie had pulled that cock out of his fly hole and was licking along the shaft. "And one of them was a lesbian? That's so fucking hot. Did she cum?"

"No...the other two did."

She saw a drop of precum exude from the tip and licked it up...Helen was right, it was sweet. Then she realized what she'd forgotten. "Fuck!"

"What?"

"I came here straight after class and didn't have time to get more condoms from my room. Ugh...guess I can just suck you off..."

"I have some."

"Yeah?" She didn't usually trust any condoms that she didn't supply herself, but her pussy was throbbing after hearing about pledge night, so she decided to trust the simple man. "Okay...you sit there and I'm gonna ride you like they did."

"Cool." Simon applied the thin membrane about his turgid member as the curvy brunette got naked and then she sank down upon it.

"Unghff...goddamn that's a magnificent beast, Simon...ohh..." she gasped as he started groping and sucking on her large boobs. She thrilled as she bottomed out and the tip of his cock pressed insistently at her lowered cervix. "Ngh...tell me, who did you cum in first that night?"

"Ugh...ungh...the lesbian..."

She was moving upon him now. "Oh, that's so sexy...ohh...so you might be the first and only guy to ever do that?"

"Yeah...uhh...that's what she said."

"Ohhfuuuck..." She came a little at the thought. "Who was next?"

"The short one...she was really tight."

"Mmm..." she moaned and moved faster upon him. "Really filled her up, huh?"

"Yeah...unh..."

"And next?"

"Short one again...she slipped and something weird happened...ugh...felt really good and I came again."

"Ohh, you probably penetrated her cervix...shot right inside her little womb. OHH FUUCCKK!" Then Stevie was cumming as she rode Simon hard, doing her best to jam his cock as deeply inside her as possible, feeling that slight discomfort as it tapped away at the entrance of her own uterus.

"I'm...cumming!" he announced and wrapped his slender arms around her curvy body, holding her tight as his load rushed up his lengthy shaft, blasted the inside of the condom, and then started to push his dangerous seed out of the tiny holes in the tip.

"Ungh! Ohh Simonnn!" Stevie ground down upon him, unaware that in doing so, she was smearing his sperm-filled semen onto her own vulnerable cervix. For the second time that day, drops of his proven seed slipped inside her defenseless baby chamber at the worst time of the month. "Unhh...can I stay the night?"

Simon let her, and took her from behind a couple hours later while she slept, though she quickly forgave him when she reached down to find that he'd wrapped it up again. She had a nice cum as he filled the condom up, once again dripping some of his boys inside her. As the unsuspecting girl snuggled back into him, his sperm swam deeper inside her, and they would not be denied.

---

"Hey, can I get more condoms to use with Stevie?" Simon asked as he fucked Vesper from behind. The slim blonde's period had stopped after a few days and she hadn't asked him to put one on since she now trusted him and was on the pill anyway, just starting her third month.

"You used 'em all up already? That's so hot..." She reached down and rubbed at her prominent clit as she thought about Simon's sperm burbling out the tip, deep inside her frenemy's unprotected reproductive system. "Oh shiiitt!" she cried out as she came, setting off his release as well. As he grunted and she felt the pulsing pressure of one of his massive ejaculations, she continued cumming. "NGH! Uhh! Jeeesus...ohh..." She sighed as he carefully withdrew. She actually didn't have any more of the trick prophylactics. "Uh, just ask her to supply them...tell her you don't need 'em with me anymore. Mmm..." She played with his warm spend as it dripped out of her.

---

"You're fucking without rubbers now?" Stevie asked as she mounted his condom-covered cock. "That's so hot...ohh..." She managed to take all of him inside her without much trouble, she'd been fucking him so often lately. "Unhh...so who do you prefer, her or me?"

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"I don't like to compare..."

She gave him a light smack on the cheek. "C'mon, don't be a pussy...tell me." Then she started riding him again.

"Okay...her."

She stopped moving and stared at him. "What?"

"Uh...her?"

She smacked him hard and dismounted. "Fucking asshole!"

"Uh, what's going on?" he asked as she angrily pulled her clothes on.

"You're a fucking asshole, that's what's going on!" Then she exited his place, slamming the door as she went.

Simon rubbed his cheek, frowned, and rolled the condom off to toss it into the waste basket. Then he pulled out his phone. "Hey, Muriel, you busy?"

---

On Saturday, Simon returned to the Phi Epsilon Tau 'dungeon' for the second week of the pledge challenge. The three women this time were a basic blonde with C-cup breasts and pigtails that made her look like she was still in high school, and two Black girls, one with absolutely massive breasts and the other with maybe B-cups.

After determining their order, the one with the huge gazongas clambered into Simon's lap. She lined their crotches up awkwardly due to her boobs getting in the way, but then they both gasped as she took him inside her voluptuous body. "Ohh, that's quite the snake," she told him sexily.

Helen performed the MC duties again. "Applicant D is nineteen years old, has had a few boyfriends but nothing serious, and is uncertain about having children because she's afraid that her breasts will get bigger...those magnificent mammaries are J-cups!"

"Ugh...I swear they grew a little in the last couple days too...stupid pills...ohh..." She'd managed to get Simon all the way inside her and was riding him quickly.

"That's time! Next."

The next girl was the blonde. "Applicant E just turned eighteen years old today -- happy birthday! She graduated high school a year early because she skipped first grade due to her being able to read and write in kindergarten. We expect big things from her." Like her belly in a few months, Helen added in her head.

"Ohh...myy..." the blonde moaned as the head of Simon's cock popped inside her.

"She was a virgin up until a moment ago -- congratulations, you two! 'E' would like to become a doctor and maybe have a child when she's around forty."

"Ugh...oww..." the blonde moaned as she got halfway down his cock.

"And...that's time. Oh, can we please get a towel to clean up the blood? That's not sanitary. Thank you, Sierra. No, don't lick his...Sierra?"

"Just making sure it's clean," the sexy brunette replied before she headed back to her seat with the blood-streaked towel.

The other Black girl settled onto Simon's length. "Oof! Damn!"

"Right?" the busty one called out. "You good, sis?"

"Yeah..." the newcomer adjusted herself and was soon grinding down upon him.

"Applicant F is the twin sister of Applicant D -- fraternal, of course."

"But this is a sorority," Simon called out.

"Fraternal twins instead of identical...keep your mouth shut unless you're cumming, Cockboy," Helen chastised him.

Simon looked back and forth between the sisters...he hadn't noticed at first, but there was a definite family resemblance below their blindfolded eyes.

"She's only had one boyfriend, though she broke up with him before coming to college last year. She would like to have children as soon as possible once she finds the right man. Perhaps Cockboy, 'F'?"

"Ugh...shit..." The girl was moving slowly as she got used to Simon's length. She had no interest in a white boy, though his trouser snake was seriously impressive. "Mm..."

"Time!"

As 'D' slipped his cock back inside her, she rubbed her J-cups along his cheeks. "You ever fuck someone with huge tits like me, Cockboy?"

He shook his head, which was quite the feat while between those meat balloons.

She moved closer to whisper in his ear, "You know, if you only cum inside me and my sister, we can make it worth your while later. You ever fuck twins side-by-side?"

Her boobs had dropped as she leaned forward so he could nod and look over at one of those twins, Sierra, as the sexy brunette looked on with lust, her fingers rubbing between her legs. At the remembrance of fucking her during his initiation, he felt his balls give up their first load of the night. "Cumming!" he grunted.

"Ti--! Oh...well, we can wait for him to finish, I think," Helen decided as she watched the boobiferous Applicant D get inseminated and wondered if the girl's chest would get bigger while she carried Simon's baby. Finally they were done, and she reminded the applicants not to let a drop spill out as the stacked young woman reclined onto her insemination settee, inadvertently making sure that the slim young man's virile seed soaked into her lowered cervix. "Applicant E?"

The blonde touched Simon's glistening, still-erect cock, and pulled back. "His stuff is...um..."

"You want that stuff inside you to win, 'E'...a lot more, so get fucking," Helen directed her.

"Uh, okay..." The blonde awkwardly mounted him again, which was a lot easier with the semen as lubricant. Her tummy thrilled at the thought of the sperm from the young man, whose identity she would probably never know, swimming up inside her. She was very glad of the sorority's free birth control pills, as she was right between periods, the worst time for this. As she moved upon him, she marveled at how the discomfort was lessening. She reached down to rub at her clit, which helped. Soon enough, her time was up.

"Did you cum when my sister mentioned you fucking us both later?" the smaller Black girl whispered in his ear. He nodded. "Yeah...that'll be fucking hot...you got a load for me, Cockboy?" She bounced on him as she approached her own orgasm.

"Time!"

"Sorry," Simon told her as she switched out for her sister.

"Unhh...gotta be careful..." 'D' whispered to him as she moved slowly upon him, "if I get you close, you'll cum inside blondie instead of sissy." At his nod, she slowed her movements.

"Move faster, Applicant D!" Helen called out.

"Damnit..." the big girl sped up, getting close to her own orgasm before her time ran out.

"Ungh..." the blonde grunted as she quickly mounted Simon. She'd been masturbating while waiting for her turn, not realizing that her horniness had been amplified by the hormone-filled, fake birth control pills that the sorority had supplied all of the applicants for the last couple of months. Within thirty seconds, she came hard on Simon's long dong, her tight, recently-devirginized pussy practically sucking out his dangerous load. "OhhAAAHHH!" she screamed.

"Cumming!" Simon announced as he filled the blonde up, her very fertile, shaking body accepting his manly tribute.

"Damnit!" one of the twins called out.

The blonde managed to keep it together so that she didn't spill any of his load as she dismounted and approached her settee on unsteady legs.

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