Another Wednesday Night

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A light hearted little story to fap to.
7.5k words
4.5
70.1k
104

Part 1 of the 2 part series

Updated 06/08/2023
Created 10/10/2016
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This by no means a major literary work. It was something I wrote the opening paragraph for, then came back to every now and than and add a little at a time. I hope you like it, especially the interplay between the characters.

Don't look for anything deep here, this is just something to fap to, so just relax and enjoy yourself.

All characters are over 18, or the legal age of the jurisdiction the reader is masturbating in.

* * * * *

Another Wednesday Night

"Do you ever think about me when you're jerking off?" Sarah Colson asked her son, Billy. They were sitting on the couch in the den, watching another old rerun on TV, when Sarah suddenly realized that she was both bored, and horny.

At thirty-seven, Sarah easily passed for twenty-something, and constantly had men propositioning her and making lewd comments to her. With her classic models features, her face got alot of attention, but what attracted the men to her like flies, were her big bouncy tits, and tight round ass. Most people found it hard to believe that she had a nineteen-year-old daughter and an eighteen-year-old son.

Even after nursing both of her children, her thirty-six DD-cup tits stood up firm and high on her chest. She didn't need a bra, but wore one most of the time anyway, mainly because it was just more comfortable. She saw the way her friends tits sagged, and she wanted to avoid that as long as she could.

She dated on a regular basis, but rarely went out with the same guys more than once or twice. She liked most of the guys she went out with, but there was always something lacking, usually between their legs. Her husband had been extremely well hung, and she missed his huge cock terribly. She had yet to find another guy with an equally impressive hunk of cock meat.

"Wh...what did you s...say, Mom?" Billy sputtered, staring at his mother in disbelief.

"I asked you if you ever fantasized about fucking me when you jerked off." She said casually, turning on the couch and resting her back against the armrest. She spread her legs, letting her short skirt fall down between them, barely covering her panty covered cunt. "I know you jerk off, you leave cum stains all over your sheets."

"Jesus, Mom!" Billy said, blushing bright red. "That's not the kind of thing you should be asking me!"

"Maybe you're right, honey." Sarah smiled. She looked him over appraisingly, her eyes falling to his crotch. "But do you have a big dick, Billy? Your dad had a big one, and judging by the loads you leave on your sheets, your balls gotta be fucking huge!"

"Mom! What the hell has gotten into you?" Billy asked her. "Have you been drinking or something?"

"No, I haven't been drinking." She laughed. "I'm just really horny all of a sudden. None of the guys I date can fuck worth a damn, and most of them have little dicks that I barely feel when they stick them in me. I was just wondering if you had a big cock, you know, like your dad's."

She gave him sultry look and smiled at him. "If I show you my pussy, will you show me your cock, baby? I can see you're already getting hard, and I think you do have a big one. Come on, whip it out, and show it to mommie."

Billy gulped and stared as she slowly drew her skirt up, moving it from side to side. The bottom of her panties came into view, and he swallowed hard.

"Well, do you want to see mommies' pussy, Billy?" Sarah giggled. "I think it's really pretty, and I know you'll like it. All you have to do is say yes...hell, just nod if you want."

Billy's head bobbed up and down like a bobblehead doll, making his mother laugh with delight. She drew her skirt up quickly, and Billy's eyes got wide when he saw that the crotch of her panties was soaked with her juices. He could see the clean shaven lips of her pussy outlined behind the thin material.

"You still haven't answered my question, honey." His mother said lightly as her fingers hooked under the sheer fabric of her panties, pulling them to the side slowly, then dragging her fingertips up the length of her cream soaked cunt slit. "Do you ever think about fucking me? Do you lay in bed at night and think about sticking your big, hard cock in mommy's tight, wet, little pussy while you jerk off?"

"I...I...well, you know, som..." Billy sputtered, unable to take his eyes off of his mother's pussy as she ran her fingers up and down between her puffy pussylips.

Watching her son closely, Sarah smiled when she saw that he was stroking his cock through his pants. She made sure that her son was looking at her when she brought her hand up to her mouth and started licking her fingers clean.

"Oh shit!" Billy grunted, stroking his cock harder through his jeans.

"Go ahead and take it out, Billy." Sarah purred. "I want to see it. You've seen my pussy, so it's only fair that I get to see your cock now."

Billy kicked off his sneakers, then opened the button on his jeans, jerking the zipper down. He pushed them down over his hips, and his mother grinned when she saw that he wasn't wearing underwear. Kicking them off over his feet, he leaned back on the couch, spreading his legs as he wrapped his hands around the thick shaft of his jutting cock.

"Oh my fucking god!" Sarah panted, staring in wonder at the enormous hunk of cock meat standing up between her son's legs. Her son's cock looked like it was at least eleven inches long, and as big around as a beer can. Sarah's pussy drooled as she looked at it.

Sliding over closer to him, she reached out, her fingers inches from his throbbing cockshaft, when she heard the front door slam, and her daughter Cindy's voice called out, "Mom? I'm home! I'll be in my room."

"No, come in here first." Sarah called back, smiling at Billy as she reluctantly withdrew her hand. "I'm talking to Billy, and I might as well do both of you at the same time." She gave Billy a wink as she sat up, smoothing her skirt over her legs.

Cindy stuck her head in the door and smiled at them. "I'll be right with you, I just need to go to the bathroom real quick. Won't take a sec."

"You can wait a couple of minutes, Cindy." Sarah said, turning and looking at her. She was immediately suspicious because her daughter was keeping her body out of view. "You come in here right now."

"No, Mom. I have to pee really bad. I'll just be a minute." Cindy said as she disappeared down the hall.

"Goddamn it." Sarah muttered. "That little bitch is up to something."

She got up and moved quickly out of the den, catching sight of her daughter as she started up the stairs to her room.

"Stop right there, Cindy!" Sarah laughed when she saw the outfit her daughter had on. "Hmmmm, I can see now why you wanted to get to your room in such a hurry!"

Cindy was wearing a white button down shirt with no bra, a short, pleated plaid skirt that barely covered her asscheeks, and white thigh high stockings. A pair of five inch heels completed her outfit. Her clothes were rumpled, and there was a long run down the back of one stocking. From behind, it was obvious that she wasn't wearing panties.

"Wow! You look hot, baby!" Sarah giggled. "Turn around so I can get a good look at you."

"I...Mom, I really have to pee! Can I go do that, then come ba..."

"No, I want to see something first. Now turn around and stand right here in front of me."

Cindy reluctantly did as her mother instructed, turning on the stairs, her crotch at eye level with her mother. She stood, head bowed, her hands clasped in front of her.

"Those are my fuck me heels, aren't they?" Sarah said as she ran her eyes up and down over her daughter's body.

At nineteen, Cindy was following in her mother's footsteps physically. Blonde, blue eyed, with a tight round ass and already packing a pair of thirty-four D-cup tits. She had a steady following of boyfriends, and they seemed to change every week, if not every few days.

"Ye...yeah, I bor...borrowed them earlier." Cindy said quietly. "I'm sorry, Mom. I should have asked."

"The patent leather flats would look better with that outfit, and be a hell of a lot easier to walk in." Sarah said lightly. Her gaze settled on her daughters legs, just under the hem of her skirt. Leaning closer, she smiled as she saw a gleam of creamy liquid on the insides of her thighs.

"You went out with that Henderson boy tonight, the one with the van, didn't you?" She asked her daughter.

"Ye...yeah. His name is Bobby, Mom."

"So how many times did you fuck him, Cindy?" Sarah asked, looking up at her. "Did you do it in the back of his van, or did he take you somewhere nice, so you could be comfortable?"

"Mother!" Cindy said, staring at her mother in shock. "How could you say something like tha..."

"Oh please!" Sarah laughed, reaching out and pushing her hand between her daughter's legs. Her fingers slid easily over the soft smooth skin of her thighs on a sheen of girl cum and jizz. Sarah looked up at Cindy as her fingers probed at the opening of her pouting pussy hole, then slipped easily inside.

"Goddamn, Cindy! How many loads did that boy dump in here?" She asked as scooped out a thick glob, holding her hand up so the gooey mixture ran down her fingers. She held them up in front of Cindy's face, smiling at the stunned girl. "If that's not cum, would you mind telling me just what the hell it is?"

"I...well, you know...I..." Cindy sputtered.

"Mmmmmmm, not bad." Sarah moaned as she licked up a thick glob of the sticky mixture, swishing it around in her mouth. She held her fingers out to Cindy again, but she shook her head, her long ponytail flying.

"Have it your way." Sarah said, popping her fingers in her mouth and sucking them clean.

Cindy stared at her, unable to believe what she was seeing. She felt a shiver ripple through her freshly fucked cunt hole, followed by a flood of girl cum.

"Come on, I was having a little chat with Billy, and I think you'll want to get in on it too!"

Taking her daughters hand, she pulled her down the hall and into the den, leading her around the couch.

"Holy shit!" Billy muttered when her saw his sister. His cock got even harder as he stared at her as she crossed the room.

"Jezzus, mother! What do you think you're doing?" Cindy asked, her own eyes glued to her brother's humongous horsecock as she came around the end of the couch and caught sight of him.

"I really don't know yet." Sarah laughed as she pushed Cindy down on the couch, then looked back and forth between her children. "I can't seem to make up my mind! I don't know what to do first, Suck a nice hot load out of Billy's big beautiful cock, or lick all that jizz and girl cum out of your juicy little pussy. What do you think I should do?"

"Eat her pussy first, Mom!" Billy grunted, his fist flying up and down over the rigid length of his cock. "I wanna see you eat Cindy's cunt!"

"Shut up you little perv!" Cindy whispered huskily, unable to take her eyes off her brothers throbbing cock meat.

"I think you're right, Billy." Sarah laughed, dropping to her knees in front of her daughter. She looked up at her as she pushed her legs apart, staring hungrily at the lightly furred slit of her freshly fucked young cunt. "Your sister's pussy looks absolutely scrumptious!"

"Mo...mother!" Cindy gasped, unconsciously sliding down so her ass was perched on the edge of the couch, her soft, silky smooth thighs spreading wider of their own accord.

"Eat her pussy, Mom!" Billy groaned, getting up on his knees on the couch so he could see better. The fat, jizz dripping knob of his cock was inches from his sister's face, and she stared cross-eyed at it, her mouth watering.

"Doesn't Billy's cock look delicious, Cindy?" Sarah purred as she paused, her face brushing the soft brown fleece covering her daughter's cunt mound. She inhaled the intoxicating aroma drifting up from her cream filled cunt hole, her own mouth watering furiously. "Why don't you suck it for him while I suck all this hot, sticky jizz out of your pretty little pussy?"

"Oh my Go...mmmpplllhhh!" Cindy gasped, cut off in mid-sentence by her brother's enormous cock plowing into her mouth. She wasn't sure just how it got there, whether he had shoved it in, or if she had engulfed it on her own. All she knew for sure was that the fat, spunk dripping knob felt incredible filling her mouth, and the taste of his hot creamy cock milk was driving her wild.

Sarah giggled as she pressed her face against the gaping gash of her daughter's pussy, moaning as she tasted the delicious mixture of creamy girl cum and gooey white jizz drooling from it. Her lips locked around the puffy pink labia as her tongue slipped up into her cunt hole, sucking lightly as she darted her tongue in and out.

Cindy moaned around her brother's cock, bringing one hand up and wrapping it around the thick throbbing shaft as her hips humped up at her mother's hungrily sucking mouth. Her other hand dropped down, her fingers wrapping in her mother's hair, pressing her face harder against her sopping wet pussy.

Billy had both hands on his sister's head and was fucking her mouth with fast, frantic strokes, his fat cock plowing between her wide stretched lips and beating at the opening of her throat. His ass was a blur as he jerked her head back and forth, forcing more of his cock into her mouth on every stroke. His hot, stacked older sister starred in most of his fapping sessions, and actually having his cock in her mouth was a dream come true.

Cindy gagged when Billy's cock drove down her throat, the fat knob tickling her tonsils. She tried to pull her head back, but he had his hands clenched in fists in her hair as he fucked her mouth harder and faster than any other guy had ever fucked her pussy.

Moving her hand up from her mother's hair, she pressed it against her brother's stomach as she dropped her hand off of his cock and wrapped it around his balls. Squeezing his balls as she pushed as hard as she could on his stomach, she jerked her head back, turning her head as his cock slipped from between her lips.

"Fuck! That thing is huge Billy!" She panted, wrapping her hand back around it, jerking on it with a rapid motion. Her hand slid easily up and down over the spit slickened shaft, and she brought the head back to her mouth, running her tongue around over the knob, licking up his pre-cum as it drooled from his piss slit.

"Shit Cindy! I was gonna cum in a minute!" Billy grunted, trying to push his cock back into her mouth, but Cindy turned her head, and his fat cock slid across her cheek, leaving a sticky trail of pre-cum and spit.

"I know you little asshole!" Cindy moaned, tugging on his cock, trying to get him to move between her legs. "But I want to feel this monster in my pussy before you cum. I've never even seen a cock as big as yours, much less felt it filling me up!"

"Oh, we definitely have to correct that situation." Sarah laughed as she gave her daughter's pussy one last lick, then slipped up onto the couch on the other side of her. "Every girl deserves to feel what it's like to have a huge, hard horsecock filling her pussy at least once in her life."

She smiled at her son as she dropped her hand down, spreading the lips of Cindy's pussy with her fingers.

"Get down between her legs Billy." She said, glancing down at his enormous cock throbbing and dripping in front of them. "Be a good boy and stick that fat fuck pole in your sister's juicy little pussy and show her what a real cock feels like."

"Fuck yeah!" Cindy moaned, watching her brother scramble off the couch and get on his knees between her legs. "Bobby's cock is barely six inches long, and not very thick. That monster you have between your legs makes his look like a pencil!"

Billy's cock throbbed, swelling and stiffening even more when he heard that. Bobby Henderson was the star running back on the football team, and he had been bullying Billy for years.

Wrapping his hand around the root of his cock, he fit the fat knob between the lips of his sister's pussy and started to press forward.

Cindy groaned as his huge cockhead spread the lips of her pussy, stretching them wider than any cock she'd had in her. And he didn't even have the head in yet!

Sarah giggled at her son's eagerness, and moved her fingers from Cindy's pussy, wrapping them around the thick shaft of Billy's cock, just behind the head.

"Slow baby." She said, smiling down at him. "Put it in slow, and let her get used to it. Just put the head in, and stroke it in and out a little, then feed her a little more when you feel her pussy relaxing around your cock. Take your time honey, we've got all night, and you're going to get all the pussy you can handle, I promise."

Billy gulped, nodding as he started rocking his hips back and forth slowly. He watched his mother's hand bump against his sister's pussylips as the swollen knob of his cock eased in and out through the tight ring of muscle guarding the opening of Cindy's pussy.

"Oh fuck, that thing is so fucking big!" Cindy whimpered, arching her ass up off the couch, trying to get more of his cock inside her. "Fuck, I can't believe how its stretching me! Oh god, it feels so good! I want more Billy! I want it all! Just shove it in and fuck me!"

"You heard her." Sarah laughed, moving her hand off Billy's cock. She brought it up and opened the buttons on Cindy's blouse, baring the full fluffy mounds of her tits to their gaze. "Go ahead Billy, shove it in and fuck the shit out of her, she really wants it."

Cupping one of her daughter's tits, she lifted it, letting her tongue run lightly around the areole before sucking the nipple into her mouth. She squeezed and molded the spongy tit flesh as she nursed on the stiff little bud, waiting patiently for what she knew was coming.

Billy put his hands on the insides of his sister's thighs, spreading them wider as he humped his ass forward, forcing almost half his cock into the tight, wet depths of his sister's quivering cunt hole. Pausing for a moment, he drew back a little, then drove forward again, forcing another three inches of his cock into the spasming hole.

Cindy let out an ear splitting shriek as she felt the throbbing bulk of her baby brother's enormous cock bulling into her pussy. Her body arched up off the couch, unconsciously forcing another couple inches of cock meat into her wide stretched cunt hole. Pain blossomed in her brain as a searing heat swelled out from her crotch.

Sarah bit down on her daughter's nipple, knowing how much she enjoyed rough treatment on her tits, and hoping her daughter liked it just as much. Her teeth dug into the stiff little tit tip, and she drew her head back, lifting her tit mound away from her body.

Cindy screamed again, her body flopping mindlessly as he brother started pounding his cock in and out of her, going deeper with every stroke. She was overwhelmed by painful and pleasurable sensations that swarmed over her in fiery waves.

Billy stared down at his sister's crotch, watching his fat cock plow in and out of her tightly clasping cunt channel. His ass arched forward again and again, driving his cock as deep as it would go. He felt the head of his cock bumping against something deep inside her, and he thrust even harder, trying to get every inch of his cock inside her.

"Is it good baby? Is it everything you though it would be?" Sarah asked, moving up to whisper in her ear. Her hands roamed over Cindy's body as the girl writhed and thrashed around under the onslaught of her brother's powerful fucking.

"Gahhh...whaaaa...mmmmppphhh." Cindy gurgled, her eyes rolling up in her head.

She'd never felt anything like this. None of her boyfriend's cocks ever filled her pussy like Billy's was, and they never went as deep as he was. She could feel the head of his cock beating against the knarled knot of her cervix, and the thick shaft scraped across her g-spot on every stroke. The way his cock was stretching her pussy, the sensitive gland was getting constant stimulation, and his cock hairs were grinding into her clit as he bottomed out in her.