Simon Book 2 Chapter 4

Finally, the sorority sisters helped Applicant E, the devirginized blonde that Simon had inseminated twice that night, off of his still-hard cock.

"What's your name?" the blindfolded girl called back to Simon as she was led away on shaky legs, his glistening seed slinking down her inner thighs. She'd already won, so didn't need to make sure that it all stayed inside her anymore.

"His name's Cockboy!" Helen called out over the speakers before turning off the microphone. "Make sure that girl is nowhere nearby when he leaves," she asked Sienna, one of the sexy brunette twins assisting her.

Her sister, Sierra, went to unfasten Simon's shackles. "Um, Simon, do you wanna stay the night...with me?" She eyed his persistent, chemically-enduring erection.

"Yeah, sure, Sierra."

He was able to cum one last time that night, deep inside the twin, after she made love to his cock with her mouth enough to get him close again. After that, they snuggled up together in her bed and fell asleep.

---

Simon woke in the morning with Sierra moving slowly and softly astride him. "Oh, hey."

"Shh." She motioned to the side, where he saw the real Sierra still sleeping beside him.

"Sienna?"

"She got to feel you cum inside her twice now, while Helen made you pull out with me," she whispered at him, "You're gonna fill me up, Cockboy."

He smiled. "Okay."

Sierra stirred as the rutting couple began to shake the bed as they got closer to their releases. "Hm? Ah, my needy sis. Lemme help you with that." She moved forward and took one of her sister's hard nipples into her mouth.

"Oh shiiit!" Sienna cried out as she came, setting off Simon. As his pulsing cock filled her with his hot baby batter, her orgasm redoubled and she shook upon him. "Fuuuuck..." Finally, she collapsed upon his slim chest. "How can that be so big while the rest of you is so small?" she sighed.

"Whore..."

She snapped her head up.

"...moans. Hormones. Doc said so."

"Oh."

---

Simon made the rounds with his helpers: Vesper, Muriel, and now Sienna and Sierra. Stevie was still spurning him for telling her that he preferred Vesper.

Saturday rolled around once more and Simon found himself again strapped into the fucking chair in the Phi Epsilon Tau sex dungeon. A lithe East Indian woman with perky, B-cup breasts was bouncing on his cock.

"Applicant G is 18, hasn't had any boyfriends, but is arranged to be married to a family friend. She wants a boy and girl...after marriage, of course," Helen called out over the PA system.

"Ngh...ngh..." the girl groaned. She'd been able to rupture her maidenhead herself with a toy a few weeks previous, but her first real sex was difficult, even with the lube the sorority had provided. When her time was up, she made way for a stacked white girl with brown hair and a rounded tummy.

"Applicant H is single, 19, and had a child just a few months ago. She doesn't want any more and would prefer to concentrate on her studies." Helen frowned...the poor girl was on the same fake birth control hormone regimen as the rest of the applicants, and right in the middle of her cycle, so there was a chance that Simon would give her a second child within the year.

"Oh...oh...oh..." the girl moaned as her body accepted Simon's trouser snake and began riding him. Soon enough, her minute was over, and she was replaced by an older woman with slightly sagging C-cup breasts.

"Applicant I is 38, another mother, though her children are grown and off at different universities themselves. She's been a housewife long enough and is here to finally get her business degree."

The auburn-haired woman settled her warm and wet pussy around Simon's prong. "These girls don't know how to get a man off," she whispered in his ear as she undulated her insides.

"Ooh..." he moaned.

"You just let it go inside momma when you're ready, Cockboy," she hissed into his ear as she rode him. However, she only had a minute before she had to dismount.

The dark-skinned Applicant G barely settled her tight pussy around Simon's cock before he grunted, "Cumming!"

"OH!" the East Indian girl gasped in surprise. With the sudden warm wetness, she was able to get all of him inside her before she, too, came as Simon's first load of the night pressure-washed the spasming entrance to her womb. "Oh! UHH!"

"Ugh..."

"Ooh..."

The young woman barely managed to keep his load contained as she stumbled over to one of the insemination settees to unknowingly let his load soak into her vulnerable cervix.

"Unh..." Applicant H grunted as she slipped Simon's spermy, still-hard dick inside her unprotected depths. "You're really big, Cockboy...can you shoot again so soon?" Despite the shake of his head, the young mother did her best before her time was up.

"C'mon, Cockboy..." Applicant I moaned into Simon's ear as the older woman rode him hard. "Give it to me...c'mon..." However, she was likewise unsuccessful, as was the already-inseminated Applicant G after her.

However, when Applicant H resumed riding Simon, he noticed a bead of white exuding from one of the younger mother's nipples. In a flash, he moved his head down and took her nipple into his mouth, sucking hard.

"Oh!" she gasped. "OHH!" Then she was cumming as Simon blasted her artificially-fertile depths with his second load of the night while drinking her milk.

While 'H' lay back on a settee and recovered from the massive insemination, 'I', the older woman, took her place and easily slipped his sperm-slicked cock back inside her. "I know you won't cum quickly again, but I really want your third load, Cockboy...save it for me, would you? Momma wants a warm tummy too..."

Simon whined as she dismounted. The East Indian girl came again on his cock but he didn't...then the single mother clung to him as she chased her own release, but neither came.

Finally, 'I' practically jumped on him. "My husband doesn't know I'm doing this...ugh...my pussy is his but I'm letting you borrow it tonight, Cockboy. You're bigger than him...unhh...you're right at my cervix...ugh...where both of my beautiful girls came from...c'mon...give Momma what she needs..."

"URGGHHH!!"

"YESSS! OHH FUUUCK! I'M CUMMINNGG!" She wrapped her arms around him, burying his face in her boobs as he blasted her defenseless depths with sperm-filled semen. "UGH! Ohhh...such a good boy..."

"Ooh..." Simon cooed as he dripped one last dollop inside the sexy MILF.

"What do we do now?" Sienna asked Helen in the sound booth. "Three-way tie?"

Helen grabbed the microphone. "Simon...fuck...Cockboy, do you think you can cum again?"

He sighed as the older woman pulled off of him and protected his load from escaping her depths. "I think...maybe." His penis was still hard, and the previous two Saturdays he'd been able to get it up one last time after the initiations.

However, the three women could not urge a fourth load from his balls, despite the repeated use of breast milk or tweaking his 'momma' kink. Soon, all three women were complaining about soreness from both their muscles and pussies.

Helen turned to the twins. "Sexiest orgasm of the three?"

"Applicant I," they both said together, referring to the older mother.

"Yeah, I agree. Okay..." She turned the mic back on. "Summary judgment, Applicant I wins...sorry, G and H."

"Booya!" 'I' crowed out from her settee as she threw the horns.

Simon stumbled home and barely managed to reach his small bed before he passed out.

---

The young man recuperated for all of Sunday. By Monday, though, he was back to needing 'help'. He met Vesper in the drama class' green room where he filled her up with an extra-large load, making her cum hard.

"HNNGGH!" she screamed into a pillow as she felt his massive ejaculation penetrate her depths. While she always had to go to the washroom after one of those to drip out his stuff, it felt incredibly good when he blasted her cervix.

Later, after classes were done, he joined her in her dorm room for another session. So focused were they on each other that they failed to notice Stevie slip into the room. She sat on her bed across from the rutting couple as he took the slim blonde doggy-style. As the voluptuous brunette pulled off her yoga pants, panties, and bra, her mind slipped back three months...

---

Stevie pushed the door open to the dorm room, her luggage in hand. "I'm here! Ves?" She looked around the empty room. Her frenemy hadn't arrived yet.

"Delivery."

She turned to see one of the other students holding out a brown box. "Oh, thanks." It was for Vesper, and the sender was the online prophylactic company that she bought her own condoms from. She pulled the bill of lading out of its plastic sheathe...not just condoms, but birth control pills...

She quickly took the box to the Phi Epsilon Tau house and offered to pay for a rush job, replacing the box's contents with the sorority's patent-pending hormone tabs and pierced condoms. She had been forced to offer a favor to the house mother, to be determined later, but soon had a repackaged box that she dropped in front of her room, knocked on the door, and hid while the newly-arrived Vesper opened it to find that 'her package' had arrived.

---

Now, Simon's dangerous cock was delving inside Vesper's completely unprotected and hormonally-enhanced body. Counting back, Stevie realized that her frenemy's period had started just over two weeks ago, so she was either ovulating or about to.

"Ugh...ugh...ugh..." Simon grunted as he thrust inside the slim blonde.

"Oh...ohh...ohhh..."

Stevie played with her clit as she watched, slipping two fingers inside herself in time with Simon's thrusts.

"Urgh...unghh...hrnn..." Simon had picked up speed and grabbed Vesper's hips.

He was going to do it! Stevie's fingers thrummed her clit. With the young man's high sperm count, there was a good chance that he would impregnate his unsuspecting partner, the stupid slut.

"Nnh! Nhhn!" Vesper reached down between her legs to rub at her own clit, her eyes closed as she chased her own release.

"UNH! UNGHH!"

"OHH FUUUCKK!" Vesper cried out as she felt Simon's load exploding within her and came hard. Overwhelmed, she lost strength in her arms and flopped forward, allowing Simon's cock to blast her vulnerable cervix at an advantageous 45-degree angle.

"NGH! GHH!" Simon grunted as he thrust as deeply as he could, grinding the tip of his spewing cock against Vesper's spasming cervix.

"Buhh..." Vesper moaned as her body lost all control, her insides wringing Simon's cock for all of the dangerous, sperm-filled semen it could.

"NGH! OHH!" Stevie cried out as she came on her fingers thinking about the delicious prank she was playing on her best frenemy.

"Urghh...Stevie?"

The voluptuous brunette was laying back on her own bed, recovering from that massive cum. "Oh...hey, girlfriend," she replied beatifically. When Simon pulled out of Vesper, her eyes locked onto his dripping, still-hard cock. "Goddamn."

Vesper gave her a smile as she turned on her side. "I know you fucked Simon a few times...it's fine. Y'wanna do it again?"

"She's mad at me," Simon informed her.

"Oh, right, he said he prefers me," Vesper gave Stevie a grin, "but he never said why, right?"

Stevie thought for a moment, but then shook her head.

"She lets me do her without a condom," Simon revealed.

"Your period's due, right?" Vesper asked Stevie as she shifted forward in her bed. "Why don't we do a proper comparison, since it's a safe day?"

Stevie felt her pussy itch as she continued staring at Simon's compelling phallus. "I...I don't..."

Simon got up from Vesper's bed and went to Stevie's, his bobbing prong leading the way.

She continued staring at that nine-inch babymaker. "Um...um..."

Then Vesper was next to her. "It feels so good when he cums inside, Stevie...c'mon, just once..."

Simon got on the bed and Stevie realized that she was opening her legs to him while her shirt was being pulled up and off by Vesper. Her period was due, she reasoned -- might even be a little late -- definitely no chance to get knocked up today. She lay back and opened her legs wide as Simon's cum-covered cock zeroed in on her wet, vulnerable pussy. "Oh shit..." she moaned as she felt the head push between her engorged folds. At the thought of the remains of his last ejaculation with all those dangerous spermies being inside her unprotected reproductive system, in combination with her brain cross-wiring upon seeing Vesper possibly get impregnated, she came hard. "UNGH! OHHH!"

As her insides lubed up with her orgasmic juices, Simon pushed inside her all the way. "Yeah..." He pulled back and thrust inside again and again, faster and faster.

"Ghh! OHH!" Stevie was still cumming. She wrapped her arms and legs around Simon as he took her. "So good...soo goood..." Sex for the first time without a sensation-deadening condom was overwhelming, and her insides kept squeezing Simon's cock, bringing him to his second orgasm quickly.

"Cumming!" he cried out as he thrust as deep inside the voluptuous brunette's lush body as he could.

"FUUUUCKK!" Stevie screamed as she felt the hot, wet pressure of one of Simon's massive inseminations blossom deep inside her and her orgasm, which had calmed a bit, bounced back. "UGH! UNGH!" She held onto Simon's slim body for dear life as he pulsed inside her again and again. Finally, she collapsed, her extremities falling to the mattress.

"So which of us do you prefer now, Simon?" Vesper asked him.

He looked back and forth between them. "Uh, I think I may need to compare some more."

Stevie's body shook with an afterorgasm. "As many times as you need. We can keep doing that until my period arrives...and maybe during, if that doesn't bother you? Maybe a couple days after it stops...?"

Vesper smiled.

---

Back in the Phi Epsilon Tau house, Helen was editing some of the footage from Simon's first round of initiates when Sienna entered. "Well?"

"All three are a week late."

"Really? Even 'A'? He didn't cum inside her." She was referring to the tall girl, Muriel.

The hot brunette nodded. "We figure it was the stuff left over on his cock from when he came in 'C'. I told them that they might miss a period after being on birth control pills for a couple months and they seem to have bought it, so we should be good until the finals."

Helen's pussy throbbed as she turned back to the video. She was going to have to get a piece of 'Cockboy' after next week's initiation.

---

"You okay, Stevie?"

The curvy brunette frowned at her phone calendar. "I'm a few days late."

Her frenemy stepped up beside her. "That can happen if you're stressed. You were worried after you fucked Simon unprotected, right? And then again the next night. Your brain's trying to reconcile what we did versus years of the strict sexual rules you created for yourself. How about Simon gives you a nice, relaxing massage tonight? At the very least, you get a few days' reprieve from 'Aunt Flo'."

Stevie bumped her shoulder into the other girl's. "Yeah...thanks, Vesper."

Of course, a massage turned into a different activity, ending in another massive insemination inside Stevie's sexy body, and then another in Vesper's after she got turned on watching them fuck.

---

"Week four of the Phi Epsilon Tau initiations! Welcome, ladies! There's only two of you, so whichever of you gets inseminated moves onto the finals. First is Applicant J, 18 years old, from the Ukraine. She comes from a big family, so would like a whole bunch of kids one day."

"Your penis is...ohh...amazing," the hourglass-figured platinum blonde moaned as she sank down on Simon's cock. "Yes...please to be cumming inside me..." she drawled with her exotic accent. However, Simon wasn't a quick shot, and her time quickly ran out.

"Applicant K is 19 and has a boyfriend, but what her man doesn't know won't hurt him. She's not sure if she wants kids but might be convinced one day."

The bronze-skinned young woman moaned as she settled her curvy hips in Simon's lap and slipped his cock inside her puffy pussy. Her wide B-cup breasts bounced as she rode him. Simon couldn't tell if she was Mexican or Native American, but she was pretty, with full lips.

The two women alternated until Simon couldn't take it anymore. 'K' was riding him, the bronze-skinned girl's hot insides urging the cum out of his balls, but just as he was about to release...

"Time!"

'K' dismounted just as Simon grunted and blasted her midriff and crotch with his load. "Ugh! Urgh..."

"Um...does that count?" she asked.

Helen considered before speaking into the mic, "No...he has to cum inside, but we also won't disqualify you because some of his stuff is now dripping onto the floor."

'K' nodded and went to lay back on one of the settees. As 'J' started riding 'Cockboy' again, 'K' looked at the ridiculous amount of semen the young man had shot onto her tummy, thighs, and pudendum. Feeling incredibly horny at this time of the month, she gathered some of the pearlescent stuff onto her fingers and then thrust those digits inside her needy hole while manipulating her clit. "Mm..."

"Time!"

'K' re-mounted the young man. "I was just shoving some of your cum inside my pussy...can you feel it?" she whispered to him as she rode his slick prong. "How about you give me more, deep inside?"

"Ohh..."

However, he didn't reach his second orgasm before she ran out of time. After the hourglass platinum blonde re-mounted him, she moved her mouth to his ear. "I am, how you say, bisexual? If you cum inside me, I will make my girlfriend lick it out after."

"Ohhfuuuck cumming!"

"Ahh! Yesss..." she hissed as she felt him blow inside her. "Ohh, that feels...OHHH!" Then she was cumming as well as she felt his hot seed pressure-wash the deepest part of her vagina.

"That's so hot..." 'K' moaned as she rubbed her clit...a moment later, she was cumming as well, her consolation prize.

"We have our winner!" Helen turned the mic off. "Clear everyone out...I'll deal with Simon," she told Sierra with a wink. Then she headed out to the dungeon. "Simon, I've been watching you inseminate initiates for four weeks now, and I'm boiling over!" She unfastened the top few buttons of her blouse. "You said that I was sexy...can I try you out?"

His eyes devoured the voluptuous older blonde, so much like his own mother, other than the hair color. "Yes, ma-- uh, Helen."

"Good answer, Cockboy." She pulled off her blouse to reveal a stalwart brassiere restraining her D-cups below a dusting of freckles. In a moment, her titsling joined her blouse on the floor, quickly followed by her skirt. She was wearing only stockings held up by a garter belt; she had forgone panties in preparation for this.

Simon gulped. His cock hadn't flagged at all.

The older woman climbed astride him and rubbed her very wet pussy along his semen-slicked member before moving upward and ramming herself down upon him. "Unghf! Oh, it's been a while, but I'm so ready, Simon...ungh...oh, suck my boobies..." She offered one large mammary to the still-restrained young man and he took it into his mouth. "Ohh, good boy...ohh...OHH!" Then she was cumming, slamming herself down upon him, feeling the tip of his compelling cock tapping at her cervix. "Ungh! Ohh...and you can keep going...soo good..."

She managed to cum twice more, but felt her energy waning...she wasn't a teenager anymore. "This reminds me of my initiation, almost 20 years ago," she informed him, "but my partner wasn't as big as yourself...I didn't even cum once. Do you like my body, Simon?"

He nodded. While Helen had large breasts, she actually had a thin waist, difficult to tell while she was clothed. She was like one of those sexy cartoon women.

"Unhh...I never had kids, but I know from last week's initiation that you've got a bit of a MILF kink, don't you?" At his blush, she continued, "Well, I'm this sorority's mother, so we'll pretend, hm?" She brought her mouth near to his ear. "C'mon, give mommy what she wants..." She undulated her pussy along his length. "Cum inside mommy..."