Simon Book 2 Chapter 2

"Bye, Momma...love you!" Simon waved as his mother drove off after dropping him off at work the next morning.

"Oh, hey...Vesper's friend, right?"

He turned to see Vesper's roommate standing there. "Hi, yes, I'm Simon von Trocken, miss." He stuck his hand out.

She hesitantly took it and they shook. "Stevie...Vesper really should have introduced us the other day." She had noticed the woman dropping off the lanky young man. "Do you like curvy brunettes, Simon?" She subtly stuck her chest out and tilted her hips in her tight yoga pants. She felt his eyes upon her and smiled.

"Sure do!"

I'll bet, she thought to herself...a man's first love is his mother. "So, how did you and skinny Vesper meet?"

"Through the theater."

"You're in the theater class?"

"I clean up in there."

She noted his coveralls. "Right. Um..." She was having trouble conversing with the guy; his weird energy threw her off.

"I gotta get to work, Stevie...bye!" He headed toward the campus.

She frowned as she watched him go. "Huh."

---

"Fuck, yes...fuck me...FUUCK MEEE!" Vesper cried out on the couch of the green room as Simon slammed his long dong deep inside of her. When she came, it set off his own release...she could feel the throbbing of his voluminous load inside her, the thin wall of the condom the only thing keeping his seed from her womb...or so she thought. Once again, Simon hid the evidence of what he thought had been his mistake when he put the prophylactic on.

She had him come to her dorm room after work to fuck her again, she was so horny, and his lengthy member never failed to make her cum. When they were done, he kissed her.

She pushed him back. "Simon?" His eyes shifted to the side and she turned to see her roommate there, sitting on her own bed. "Oh! Stevie."

Her frenemy gave her a salacious grin. "Just a friend, huh?"

"Okay, more than friends...unhh..." Vesper moaned as Simon pulled out. "Simon!"

The young man, seemingly not caring that his still-hard cock was sticking out, looked back at her. "Huh?"

"Jesus..." Stevie moaned at the sight of his thin nine-incher.

"Put that away before you take someone's eye out," Vesper directed him with a giggle as she pulled the sheets around her naked form.

"Right, uh, sorry." He took care of the condom and grabbed his tighty-whities.

Vesper turned back to her roommate. "How long you been there?"

"Huh?" Stevie blinked and tore her eyes away from Simon's manhood. "Oh, just came in for the finale...you're really loud, Ves."

"Well, he's really good."

Simon blushed as he pulled his clothes back on. "I should go?" he asked Vesper and she nodded. "Okay, bye, ladies." He gave both of them a winning grin and left.

"I should go too...get some dinner," Stevie commented as she left a few seconds later.

Vesper smiled as the door closed behind.

---

"Hey, Simon!"

"Oh, hey, Stevie, did I forget something?" He patted his pockets, but his wallet, keys, and phone were there.

"No...I, uh, wanted to know if you two were together-together."

"She's my girlfriend." He gave her a proud smile.

"Yeah, but exclusive?"

"Huh?"

She sighed. "Can you fuck other women?"

"Yes." Then he winced...he was supposed to turn Stevie down when she asked him to fuck, but that wasn't exactly what she'd asked.

"Cool...meet me at this address at eight." She handed him a business card, pulled out her phone, and walked away as she dialed.

"Uh..." The card was white, with embossed lettering saying Phi Epsilon Tau.

---

"Whattaya think?" Stevie presented Simon to three lovely ladies in a closed room at the sorority house, a voluptuous older blonde that reminded him a bit of his mother flanked by two twentysomething brunettes who looked exactly the same.

"He's kinda skinny," commented the left-hand brunette.

"How old is he?" the right-hand one asked skeptically...he looked too young.

"Twenty, miss."

"He's skinny, but big where it counts," Stevie told them. "Simon, take out your cock."

He did so, making the sorority sisters gasp even though he wasn't fully hard.

The blonde leaned forward. "Okay...Sienna and Sierra, get naked...we'll see how big it gets."

The brunettes peeled off their clothes, showing off their trim figures with C-cup breasts, and posed...then their eyes widened as Simon's member rose to its full length.

"Wow," the blonde breathed. "You girls, bend over the table. Simon, show us what you got." When he went to pull off the rest of his clothes, she clarified, "No, just start fucking."

The twins held up an arm toward each other. One, two, three, and they were both holding up the sign for scissors. They tried again and both had rock. Finally, on the third try, the left-hand one went back to scissors while the other went to paper. "Me first!" The left-hand one called back at Simon with a grin. "Lick me for a minute, willya?"

"Yes, miss!" Simon dived between her shapely long legs from behind to tongue at her shaved nethers.

"Not bad..." Sienna sighed. After a bit, she called him up. "Oh shiiit..." she grunted as he sank his babymaker inside her. "That's...wow..." she winced as he bottomed out...then she fell forward as he grabbed her hips and started pounding. "Ghh...ghh...ghh..."

The other twin, Sierra, rubbed at her own clit as her sister got fucked. She loved this because it was like watching a sex video of herself, one that she never remembered making. After several minutes of her sister getting fucked hard, she felt like she was going to cum soon.

"Oh fuck, I'm cuuuumming..." Sienna moaned as her body shook.

"Simon, pull out and shoot it all over her back," the blonde instructed him.

With a disappointed grunt, Simon did so, jacking his cock until he spewed his load onto the sexy brunette's spine and ass.

"Please tell me you can go again!" Sierra moaned from next to him as she rubbed at her clit.

"Yeah!" He moved over behind her and shoved his slick, still-hard member inside.

"OHH FUUUCK!" the second twin cried out as she came hard, she'd been so close to her own release.

"Feels good..." Simon moaned as he felt the young woman's pussy grip him. She was already so wet that he was able to fully embed himself inside her sultry depths without difficulty.

So focused was he on his partner that he didn't notice the blonde come around to scrape much of his first load from Sienna's backside into a test tube. When she was done, she licked up the girl's spine and swallowed some of his stuff. "Mm! You eat a lot of fruit, Simon?"

"Huff huff! Yeah, Momma insists I eat healthy."

"Nice...you can shoot your next load inside Sierra." Then she stepped out of the room with the sample in hand.

Sienna groaned in disappointment and reached around her back to capture some of his stuff on her fingers, which she sucked into her mouth with a satisfied purr.

Stevie was sitting in a chair watching Simon's performance, rubbing her thighs together as his tight ass powered into the second twin's wanton body. She really wanted to jill off, but knew that this room had hidden cameras and didn't want to give the sorority any more leverage over her.

The blonde slipped back into the room and sashayed over to Stevie. "Nice high count...you did good, girl," she whispered.

"So we're even if he helps with the pledges?"

"Your favor pissed off some regulars, but yeah, I'd say so."

Stevie gave her a grin. "Nice!" Then she and the older woman looked up to see that the fucking pair were finishing up. "Oh..."

"Urghh!" Simon grunted as he thrust deep and blasted Sierra's hot depths.

"FUUUUCKK!" the hot brunette twin screamed as she came again. "I...feeel...ittt...ughh...urghh...NNH!" Her orgasming body seemed to dance on the end of his spewing cock until she fell forward, stunned.

Simon pulled out and caught the girl as her knees almost gave out. "Whoop!"

The blonde came forward. "Simon, you're invited to Saturday's pledge night for more sex, and the next three Saturdays afterward. Show up at the same time. Goddamn..." She gave his softening member a stroke. "Big things do come in small packages. You can't tell anyone about this, though, okay? Otherwise nobody from this sorority will fuck you anymore." She licked at her fingers.

Simon nodded, thrilled...more women helping him! He headed out with Stevie on his arm.

The blonde moved behind Sierra with another test tube. "Okay, push out as much of his stuff as you can." A few minutes later, she boggled as her microscope showed barely any difference in the sperm count of the skinny man's still-voluminous second load.

---

Stevie could feel her prominent pussy lips rubbing together as they walked. "So, after all that, do you think you could get it up again?"

He considered. "Maybe."

She traced a hand up his slim arm. "Can we go to your place and..."

Then he remembered Vesper's instructions: "Uh, no."

She stopped. "No?"

"You're Vesper's roommate, so that would cause problems." He shrugged and gave her a 'sorry' grimace.

"I, uh..."

"Oh, I see my bus coming...see you later!" He dashed across the street.

When she got back to the dorm, Vesper was there doing homework so Stevie couldn't masturbate. She finally went to bed unfulfilled.

---

Vesper was so happy the next day when Simon told her that he had rebuffed Stevie's advances that she blew him to completion in the green room, gulping down his expansive load as he moaned and gazed down at her beatifically. "Wow, I don't think I'll need lunch after that," she commented with a burp.

After class, since her period was due, she decided to finally have sex with him without a condom. When he finally blasted her insides with his hot load, she came hard, her nubile body shaking as his seed penetrated her deepest, most personal place. "Ohh Goddd..." she sighed, her nipples incredibly hard at the thought of his copious seed invading her womb, despite her being on the pill and it being a safe day. She loved how he was just ready to go when she was.

---

Saturday rolled around and Simon arrived at the Phi Epsilon Tau house as directed, where he was greeted by the older blonde wearing an elegant gown.

She held out a yellow pill and a glass of water. "Welcome, Simon! Please wash this down...it'll make sure you're good all night."

He did as directed and handed the glass back. "I don't know your name, ma'am."

She frowned. "Ma'am? Make me feel a million years old, why don't you? I'm Helen Stockton, the mother for this sorority...call me Helen."

"Pleased to formally meet you, ma--uh, Helen. You're not old...you're like my mom's age, and very sexy."

She blushed. "Thank you, Simon. C'mon..." She beckoned him to follow her down some stairs. "Our pledges will be playing a game where they ride your cock for a minute at a time. The one who gets the most loads moves onto the finals, so be sure to be very vocal when you cum, okay?"

"Okay."

She opened a door to reveal a room with weird-looking, angled sofas along the walls and a wooden chair bolted to the floor with a couple of metal wrist bracelets in the back. "We'll be securing you in this chair so the girls feel safe...do you have any problems with being restrained?"

He took a closer look. The bracelets had some soft fur on the inside. "Never done anything like this before, but I think it'll be fine."

"To protect everyone's anonymity, the girls will be wearing blindfolds. If we have to talk to you, we'll call you, um, Cockboy, okay?"

He giggled at that, imagining himself wearing a superhero suit with a rooster emblazoned on the chest, and nodded.

---

"Ladies, welcome to pledge night! You are the first week's contestants. Your blindfolds will only allow you to see shapes with no detail so you won't trip over anything, but don't take them off or you're immediately disqualified! Your task is to ride this young man's cock, a minute at a time, and get him to shoot as many loads inside you as you can. You've been using the birth control pills we gave you for two months now, so you don't have to worry about unintended consequences. Any questions?"

Simon, whose cock had hardened after he'd been fastened into the chair and remained that way due to the pill he'd taken earlier, examined the three naked women who shook their heads. The first had brown hair and a birthmark on her upper lip that he thought looked cute...she was tall, he figured almost 6 feet, and curvy, with large D-cup breasts. The next was small, almost boyish with her slight figure and small breasts...with her darker skin he figured her family was maybe Filipino or from some other East Asian country, though it was hard to tell with her blindfold on. The third was a slim, pale redhead, though her B-cup breasts were topped with long, prominent nipples, hard from the cool air of the sorority house basement.

"Cockboy, think of a number between one and ten and show us with your fingers. Girls, call out a number."

The tall girl called out eight, the Filipino two, and the pale one five. Simon was holding out seven behind his back, so the tall girl was closest. She was directed forward and astride him, her vaginal lips already glistening from either natural or artificial lubrication, and she was able to slip his length inside her without trouble.

"Ohh my Godd..." she moaned as she settled upon him. "That's...really...ugh...long..."

Helen continued the narration as the tall girl finally got all of Simon inside her. "Applicant A is eighteen years old, has only had one boyfriend, and wants to have a couple of children...after she gets married, of course."

"Ng...ngh..." 'A' moaned as she ground down upon Simon's length, thrilling at the novel feeling of such a lengthy cock stirring up her insides. She rose up and down upon him. "Jesus..."

"And that's time!"

The tall girl groaned in disappointment and dismounted.

The pale redhead stepped forward and was careful as she spread her pussy open, nibbling her lip as she felt Simon's bulbous head slip inside.

"Applicant B is also eighteen years old...she's never had a boyfriend because she's a lesbian."

Simon blinked, surprised as the slim girl took half of his length.

"However, her mother is a Phi Epsilon Tau alum, and insisted that she join. Membership has its privileges, after all."

"Ugh...shit..." the redhead grunted as she finally took all of him. "Ohh...my toys aren't this big." She moved upon him slowly, getting used to the feeling.

"'B', of course, doesn't want any children. And...that's time!"

The redhead vacated her position and the short Asian girl clambered into Simon's lap.

"Applicant C is twenty years old, has a fiance back in her hometown, and wants lots of children after she graduates."

"Ohh!" the diminutive young woman moaned as Simon's head popped inside her small body. She moved upon him energetically, her well-lubricated channel assisting as she took inch after inch of him inside her. "Ow!" she cried out as the tip impacted her cervix.

"Time!"

The tall girl's pussy gobbled up his prick again and she bounced upon him vigorously. "Ngh, fuck..." she moaned into his ear, "you wanna suck my boobs?" He nodded and she pressed one fat nipple into his mouth. "Ohh...goddamn, your cock is so big...shit, might cum soon..."

"Time!"

"Fuck!" She extracted herself from him.

As the redhead's hot pussy surrounded his turgid member, she whispered into his ear, "Your cock's the first real one that's ever been inside me, you know." She bounced in his lap. "Ungh...ugh...c'mon, don't you want to be the first guy to ever cum inside me? C'mon...you know you wanna..." She nibbled on his earlobe.

"Cumming!" Simon hollered and shot his first load of the night deep inside the lesbian.

She continued to bounce. "Oh wow, that's...wow..." She instinctively wrapped her arms around him and ground down upon him as he inseminated her. "That feels so weird..."

"Remember, ladies, don't spill any or you're disqualified!" Helen called out. "Lay back on the insemination settees when it's not your turn." She was referring to the specially-angled furniture set up along the walls of the room.

The redhead reached down, cupped her pussy as she pulled off of Simon's spermy cock to keep his load in place, and carefully shuffled over to one of the settees. After laying back on it, she lifted her legs up over the raised arm so that her body was reclined, the angle making sure that his load stayed inside her.

Applicant C, the short girl, was happy to find that Simon was still hard as she climbed astride him. His cock, covered in a sheen of semen, easily slipped back inside her tight box. "Ugh...ugh...ugh..." she groaned as she bounced upon him, careful to not let him get too deeply inside again, as that had hurt! Soon enough, though, her time was up and she dismounted with a disappointed grunt.

The tall girl quickly shoved her tit back into Simon's mouth once she got him back inside her and thrust her crotch into his, hard. "Ergh...yeah...suck it...suck my titties...YEAHH!" Then she was cumming, her body shaking. Finally, she collapsed upon him. "You didn't cum?"

"Sorry."

"Time!"

The redhead carefully shuffled over while making sure she kept his first load inside her vagina. In a flash, she took him inside her again. "Hey, Cockboy," she whispered in his ear, "you're gonna be the only man to ever cum inside me...that's quite the honor. You should do it again...whattaya say?" She moved upon him faster.

"Oh shit..." he moaned.

"Yeah...c'mon..." she urged.

"Time!"

"Shit." She carefully extricated herself and returned to reclining on her settee.

Applicant C, the short girl, found Simon's cock covered in slick whiteness once more due to him having been inside the inseminated redhead again...this made it the second time that she was pushing sperm inside her that night without a direct ejaculation. However, once she situated her tight pussy around his primed babymaker, he cried out and blew his second load of the night inside her. "Oh! Thank you!" she sighed as she felt the pulsing. Then she carefully withdrew, covered her vaginal opening with her hand, and went to lay back on the furniture to elevate her hips.

Applicant A, the tall girl, had been playing with her clit while watching the short girl get seeded. She was glad she was on the pill, as this was a dangerous day for her, which explained why she was so horny. As she took 'Cockboy's' slick erection back inside of her, she thrilled that this was the first time that she'd actually had sperm inside her vagina, even if it was second-hand. "You gonna be able to cum again?" she asked as she rode him.

"I...think so..."

"Pleeease...I'm so fucking horny...you cumming inside me's going to set me off, big time...I just know it..." Soon enough, though, she had to dismount and the redheaded lesbian took her place.

"You got one more load for me, right?" she whispered into Simon's ear as she rode him. "What do I have to do to get it?"

"Can...can I suck on your nipples?"

She looked down...her nips were long but very sensitive. "I...okay..." She brought a breast up to his mouth and gasped as he took it between his warm lips. "Ooh..." He was licking while sucking...it was nearly overwhelming...

"Time!"

"Damnit..." She dismounted and made sure that none of his first load spilled out as she returned to her settee.

"You wanna suck my little titties?" 'C' asked him as she took his still-hard cock back inside her inseminated depths. She squeezed one of her A-cups to make it stick out a bit more, pushed it at his face, and he took the dark nipple into his mouth. "Ooh!" With one hand occupied, she lost her balance and sank all the way down on him. "OW!"

Simon felt a tremendous pressure on the tip of his cock. With how numb it had become after cumming twice, and with all the nipple play stoking his libido, he grunted and sucked on the short girl's hard nipple as he came again, the tip of his spewing member pressing directly into the entrance of her uterus. "NGH! NHH!"