Simon Bk 02 Ch 01

Vesper gasped as she pushed her favorite vibe inside her overheated pussy. The slim blonde was laying back on the couch in her college's green room, her short skirt pulled up as she pleasured herself, the 'vrrm, vrrm' of the vibe and the squelches of it penetrating her the only sounds in the quiet room that was normally used by the acting class, but empty at this time of day. "Umm," she moaned as she sluiced the sex toy inside herself again and again...she'd been so horny for weeks and had to find quiet places to take care of herself while she was sans boyfriend.

There was a thunk at the door...she stopped, quickly dropped the juicy vibe onto the couch, and rushed it. Ripping it open, she looked down at the young man who fell back, startled.

"What the fuck are you--?!" she began, but then her eyes fell on the sizable cock snaked out through the crotch hole of his blue coveralls. Jesus, she thought, that had to be at least nine inches long! It wasn't thick, but that was actually a good thing, as a proportionately thick nine-incher would probably be scary.

"Um, sorry miss!" the slim, dark-haired guy apologized, "I was just relieving pressure."

She pulled her phone out of her B-cup bra to snap a pic of the guy laying there with that trouser snake out. "What's your name, perv?"

"Simon von Trocken, miss."

He still hadn't put his hard cock away, and she realized from his vantage point on the floor that he was looking up her short skirt and her panties were still on the couch. However, she fought the urge to pull her skirt down or retreat; she had the upper hand here. "How old are you, Simon?" The kid looked to be in high school.

"Twenty."

Her age. She glanced at the school crest on his coveralls; he was a janitor at the college. "Gimme your phone number...yer ass is mine now, Simon."

"You want my ass?"

She looked down at him. "What?"

"Nobody's done that before. Would that make me gay? I don't wanna be gay...I like women too much."

She stared at him...he wasn't smiling, so was he serious? If so, this guy was not the brightest bulb in the box. "I mean you do what I say when I say it, shrimp." She looked back down at his still-erect flagpole. "Jumbo shrimp."

"Can you help me?" he asked, pointing to his turgid dick.

"I just found you whacking off while peeping on me and you want me to finish you off?"

"Yeah...please?" He gave her a winning smile.

"I...uh..." She *had* been interrupted during her masturbation, and that huge dick was compelling, but she didn't have any condoms. "Do you know how to lick pussy?"

His face brightened. "Oh, sure! Couple ladies from my home town taught me."

"All right, get in here, jumbo shrimp." She made way and he got to his feet to slip past, his bobbing dick leading the way while she closed the door behind.

He picked up the vibrator and gave it a sniff. "Mm! You smell good, miss."

She blushed a little. "Lay back." He complied and she got on top of him in the sixty-nine position, marveling at how long his dick was before she gasped upon feeling his tongue licking at her nethers. She took as much of his lengthy member as she could into her mouth, moaning into it...he was actually pretty good with his tongue. She'd already been rushing toward her release when she caught Simon peeping at the door, so redoubled her efforts on his cock, using her dainty hand to stroke up from the base as she sucked on the top half.

"Ohh, miss, I cum a lot, so be ready."

She could feel his cock throbbing and pulled back so only the head remained in her mouth. She knew she'd cum the moment his hot stuff filled her...

Simon pushed the vibrator inside her very wet pussy and turned it on.

"Hllkk!" she screamed into his dick as she came hard.

"Ahh! Cumming!"

His first burst of seed spattered her uvula and she struggled to breathe while a powerful orgasm blew through her. She gulped, breathed through her nose, and gulped again as another splash of salty cum followed while her body shook in pleasure. "Hnng! Nnh!" she groaned. Another spurt...another...

Finally, both of their orgasms wound down...she let go of his dick and collapsed forward. "Fuck," she moaned.

"Thanks, miss...you're pretty good at that."

"You too...my name's Vesper."

---

Vesper opened the door to allow Simon into her room. Her dorm was co-ed so nobody cared about who came and went. It was after classes and she'd been horny again, and since Simon had said that he needed 'help' multiple times a day, it seemed that they could help each other. Her roommate was out somewhere so she figured they had some time to play. "You're just a dick to me," she told him as she fished it out of his jeans, "so don't get all possessive, okay?"

"Okay...ohh..."

She'd sucked half of his length into her mouth, though she quickly realized that the guy didn't need any foreplay and, reaching down between her legs, she found that she didn't either. "Put this on." She gave him a condom.

"Oh, I hate these things."

She kept her eyes on that wonderful dick as she pulled off her skirt and panties. Could she...? She'd been on the pill for a couple months after her depo shot wore off, but it wasn't just about birth control...she'd just met this guy, so needed to trust him more before going without physical protection. "It's that or we sixty-nine again."

"Okay." For a moment, the twenty-year-old looked much younger with that boyish moue of dissatisfaction on his face as he fished the prophylactic out of its package. She pulled off her shirt and bra and enjoyed the look of desire on Simon's face as he beheld her slim, sexy body. He fumbled with the condom a bit, but then rolled it down his length, after which he removed his clothes and joined her on her bed.

"Go easy," she advised him as the skinny young man fisted his cock and nudged it at the entrance of her womanhood. After a couple of swipes up and down between her vaginal lips, he pressed it inside. "Ohh..." she moaned. It had been a few months since she'd broken up with her last boyfriend. "Oh fuck...that's good. Deeper...yes...oh wow...Simon, how are you this...ugh...gooood?"

"Some nice ladies...ugh...back home gave me regular help after I turned eighteen...they showed me what to do." He was most of the way inside her now, thrusting slowly but surely into her wet depths.

"Fuck...oh fuck...gonna...nnngghhh!" She was already cumming.

Simon felt her insides grip him and then relax, her orgasmic fluids lubricating his length and allowing it all the way inside.

"Fuuck...soo...deep..." She was gasping, her body still shaking as he continued to thrust into her. She gasped again as she felt him take one of her B-cup breasts in hand to suck on her hard nipple.

Simon was happy to be having sex again...after leaving home, he'd only been able to use his hand and he was starting to chafe. Vesper's breasts were the smallest of anyone he'd been with, but breasts were breasts, and he loved them. He nibbled lightly on her small nipples and felt her pussy squeeze him again. "I'm gonna cum," he told her.

She instinctively locked her legs around his midsection. "Yes...yes..."

"Unhh-OHHH!" His orgasm blossomed from his loins, rushing up his lengthy shaft before filling the tip of the condom. "Uhh! Ugh..."

"Oh!" Vesper came again as she felt Simon's cock throb inside her, deeper than anything had ever been in her life. Inside her, the head of his condom-covered cock rubbed along her cervix. "Unh! Ohh!"

Simon lay atop her as they breathed heavily, coming down from their pleasurable releases. He carefully pulled out, tied off the condom, used some tissues to wipe, and then balled the whole thing up before tossing it into the trash bin by her desk.

She'd pulled most of her clothes back on by this point. As she pulled up her panties, she told him, "I'll meet you tomorrow in the green room, same time as today, okay?"

"Okay!" He re-dressed and opened the door, almost walking into another woman, an attractive and voluptuous brunette as tall as his 5'9" frame. "Hello, miss!"

"Hello," she greeted him with a confused look before making way. Then he was gone. "Who was that?" she asked Vesper as she closed the door behind.

"A friend."

"Not your usual type."

"I said a friend, Stevie, not a boyfriend."

"Hmm..." Stevie could smell sex in the air, and from what she'd seen, the little guy had a good-size dick in his pants.

"I'm heading off to eat," Vesper told her and left.

Stevie went to the trash can, found the used condom, gave it a squish, and smiled.

As Simon headed back to his apartment, he thought back to the sex with Vesper. When he'd pulled out, he'd found that there were a few drops of his stuff on the outside of the rubber, so had quickly balled it up in some tissues before she got upset. He wasn't great at using those things, so assumed he'd put it on wrong. He still incorrectly assumed that condoms were to keep from making a mess, and hadn't seen anything dripping out of the hot blonde's vagina, so hadn't mentioned it.

---

As Vesper chewed her burger, she thought about her relationship with her best frenemy Stevie, which had been topsy-turvy since high school, with the brunette stealing Vesper's boyfriend just before prom. Of course, she'd said that was revenge for Vesper asking the guy out months before, when she knew that Stevie liked him. Well, you snooze, you lose, Vesper had told her, but stealing him just before prom was overkill. They'd patched things up afterward, Stevie having dumped the guy for having a small dick, but in the last couple years at university they'd been getting back at each other in little ways. Even with the fights, the two bitches really understood each other -- who else would? -- so they remained close.

She recalled how Stevie had been looking at Simon and felt her slut-sense tingling, or was that her pussy from the royal fucking the slim young man had given her a few minutes prior? Either way, something would have to be done.

---

"Ugh! Ugh! Ugh!"

"Yes, Simon! Yes! Oh, that fucking huge cock's pounding my cervix! Ahh, cumming again!" Vesper wrapped herself around the slim young man and ground her pelvis up into him to multiply her pleasure as they fucked on the green room's couch. "Uhh! Ohmi...UHH!" The blonde's sexy young body vibrated in pleasure as she came hard.

"Urgh! Cumming..." he moaned.

"Yesss..." she gurgled as she felt his lengthy rod throb deep inside her, additional sparks of pleasure emanating from her cervix as his ejaculating prong bounced off of it. "Nngh..."

Simon collapsed upon her, gasping. "That was really great, Vesper." Sex, even through a condom, was better than his hand.

"Yeah...fuuuck..." she moaned and shook as an afterorgasm shot through her slim body. "Mmm..."

Simon pulled out and took care of the filled condom, once again disappointed to find that he'd somehow messed up and some of his stuff was dripping out of the tip. Not wanting to upset his sex friend, he grabbed some tissues and balled it up like he'd done the first time before slipping it into his pocket, since she'd said not to leave anything behind. He'd toss it into a bin elsewhere on campus.

"Simon, I need to talk to you."

Oh no, he thought, she noticed the dripping condom! "Yes?"

She patted the seat next to her. "You remember my roommate, right, the curvy brunette?"

"Yeah, she's pretty." Noticing Vesper's frown, he amended, "But not as pretty as you." That got him a smile.

"When we're around her, I want you to pretend that you're my boyfriend, okay?"

"Okay...like with kissing and stuff?"

Vesper paused. She hadn't considered that. "I...guess so." Then she gasped as Simon kissed her, reflexively returning the tongue. She quickly recovered and pushed him back. "Only when she's around, Simon!"

"Okay."

"Now...she will probably want to get you alone to entice you into having sex with her. As my boyfriend, you will of course say no...she'll keep pushing, though, so eventually you should say yes. Any questions?"

"What does entice mean?"

"Uh, convince."

"Right...so I say no, then yes."

"Yes...uh, correct, and..." -- she went into her purse and pulled out a string of condoms that looked different than the ones they'd used -- "you should use these with her."

"I hate those things."

"I know, but that's the only way she'll let you do it." She didn't tell Simon that Stevie was allergic to hormonal birth control. Also, the condoms she'd handed him were special items purchased from the notorious sorority Phi Epsilon Tau that had been unpackaged, pierced with a needle, and repackaged, so there was no easy way to tell that they'd leak until the prophylactic was full of semen. She felt a little thrill in her own womb at the thought of Simon's no-doubt potent sperm dripping out into her frenemy's unprotected depths.

Simon slipped the condoms into his other pocket, smiling that simple yet endearing grin of his.

---

"Hi, Mom!" Simon hugged his mother Bonnie as she entered his small apartment, the only thing he'd been able to afford on his janitorial job.

"Hello, sweetie," she hugged him back. "Missed you."

"Missed you too! I've had to use my hand a lot lately. Do you think you could...?" His eyes scanned the tall, 40-year-old brunette's voluptuous body in her knee-length dress, her breasts noticeably larger since she'd had her second child over a year ago.

She looked around and, not finding a chair, sat down on his twin-size bed. "Could we maybe talk a bit first? It was a long drive, and I want to hear about your new life here."

He sat behind her and started to rub her shoulders. "Sure, sure. How's Jethro?"

"Mm..." she sighed as her son worked the kinks out. "He's doing well...I left him with your grandparents. Tell me about your job."

He pushed his knuckles between her shoulder blades, making her gasp. "I'm pretty good at it, and my boss says he'll be able to show me how to do plumbing and maybe electrical soon."

"Oh, that's wonderful, sweetie. I'm so happy you're making a new life here. Mmm..." He'd moved his hands to her lower back, which had been sore holding up her larger, post-pregnancy breasts. She moved her hand back to feel between his legs...yes, he was very hard. "You said you'd been using your hand a lot lately...you haven't found anyone to help you?"

"One lady is...uh, my girlfriend." Then he remembered that he was only supposed to say that to Stevie. Oh well, no point in taking it back...that would be confusing.

Frowning, Bonnie continued rubbing his erection through his jeans. "Girlfriend? What's she like?"

"Really pretty...blonde...little shorter than me."

She turned, her pulse racing. "Get your pants off."

He quickly complied and lay back on the bed. "Are we gonna do it?"

Bonnie remembered Simon's last year or so at home before he'd headed out on his own...she'd helped him with his medical need to ejaculate several times a day with her hand, then it had progressed to her mouth, and even one time between her thighs in the shower, though that was after she'd found out that she was pregnant from that one-night stand that had stealthed her while she was drunk. After Simon's regular helpers around the neighborhood stopped helping him as much, they'd graduated to full intercourse...just to help him get there faster, of course, and it wasn't as if she could get more pregnant. However, it had been almost a full year since she'd last had sex and she remembered what her son's big fucking cock felt like inside her. This was the absolute worst time of the month to have sex, which was probably why she was so horny. "That would probably be a bad idea." She took his compelling length in her fingers and began stroking.

"Maybe your mouth, then, or...oh, I have condoms!"

She slowed her stroking. "Well, look at you, becoming more responsible." She leaned forward and took his cock into her mouth.

"Ohh yeah, Momma..."

Bonnie reached under her skirt to rub at her hard clit through her panties as she fellated her son. He had a girlfriend now, which she figured would happen at some point, but she was his momma and their intimate connection transcended the simple, ephemeral one of boyfriend/girlfriend. She pulled off. "Where are the condoms?"

Simon watched as his mother rolled one of the rubbers that Vesper had given him down his length and pulled her dress and undergarments off, revealing her curvaceous form. His mother had already been curvy, but her second pregnancy had accentuated that even more. "So beautiful, Momma."

She blushed, moved astride him, and rubbed the tip of his cock between her extremely wet pussy lips. She couldn't believe that she was going to do this again after promising herself she wouldn't, but she was so horny. "Ohh..." she moaned as she sank down upon him, careful to not let too much of him inside all at once, given her year of abstinence. She could feel her out-of-practice pussy stretching to accommodate him once more. "Uhh..." Then she felt Simon's hands on her boobs. "Mmm..." Leaning forward to allow him greater access, she gasped as he took one of her gumdrop nipples into his mouth. "Mhm!" she moaned, her knees giving out, and suddenly most of his length rushed inside her. "OHH!" Simon continued to suck on her as her insides vibrated around his cock. Then she felt a familiar sensation in her breasts. "Wait, Simon, stop sucking or..."

"Mm!" Simon moaned as warm milk exuded from his mother's nipple and he gulped it down.

"Ohh..." she moaned. She'd been weaning the baby off of her milk, so hadn't even thought about what could happen with her son sucking her nipples. For the first time in twenty years, she was breastfeeding her first darling son again. She pulled up a bit and pressed down upon his manhood, groaning as Simon's nine inches bottomed out inside her, feeling that combination of discomfort and pleasure as the head rubbed at her cervix. She pulled up and then pressed back down upon him. "Ohh Godd..."

"Mmm..." Simon moaned as he continued to drink.

Soon, she was riding him faster, dislodging her breast from his mouth. On every downthrust, she felt the compelling pressure of his cockhead at the deepest point in her needy pussy, but she needed more. She pulled off of him. "Take me from behind, Simon!" She dropped to her hands and knees next to him. In a flash, he was behind and then back inside her. "Yes!" she exulted as the new angle allowed the head of his cock to rub along her G-spot as he pulled back. "Ngh...yesss..."

"Huff huff huff...I love you, Momma!" He reached down to flip her prominent clit.

"I love YOUUU!!" she screamed as pleasure burst from her clitoris, G-spot, and cervix all at the same time. "OHHGODD!"

"Ugh! Urgh!" Simon groaned as his mother's tight pussy practically sucked the cum out of him. Burst after burst of his cum filled the tip of the trick condom until the physical laws of the universe started pushing drop after drop of his sperm-filled semen out the tip to smear onto her vulnerable, spasming cervix.

"Guhh..." she moaned, her insides still contracting from the largest orgasm she'd ever had. As the entrance to her womb opened up, it sucked those drops of dangerous, incestuous seed right inside. Finally, she collapsed forward and the condom slipped off.

Simon quickly grabbed the rubber and pulled it out before it made a mess. It was getting dark outside, dimming his room as well, so he didn't notice the dribbles of his semen exuding from the tip before he tied it up and tossed it into his tissue-filled garbage can. His mother was laying on her side now, so he spooned her from behind. "Momma?" There was no answer; she'd fallen asleep. He reached around to palm her other breast, so full of milk, and pinched the nipple until he felt some wetness. His cock was hard again.

This reminded him of that time a couple years ago when his mother had come home and had sex with her date on the couch. After the guy had left, Simon had come to her for assistance only to find her unconscious. Undeterred, Simon had used her pussy to relieve the pressure in his balls until he'd cum inside her, not realizing that he was secretly impregnating her with her second child. Spilling the other man's condom had hidden what he'd done, but it had been the first time he'd ever had sex with his mother, even if she hadn't known, and it was imprinted on his mind. He lined his reinvigorated cock up with her still-wet pussy but then paused. He had no other person to take the blame for the mess this time. He grabbed another condom before slipping his babymaker back up inside her.