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Chapter 171: The flip Of a Coin

"Hey, mom, could I talk to you about something?" Joey asked his mom Cassie.

"Of course, you can, honey What\'s up?" the brunette mother asked cheerfully, playing a game on her phone. She set it down and gave her son her full attention.

"Well, I was um...just wondering if you heard of something called \'assturbation\' before?"

Cassie shifted uncomfortably, her asshole clenching in her panties. "I have heard a few moms talking about that. Why?" she asked, although she had a pretty good idea what was coming next.

"Do you um...know what it is?" the boy asked awkwardly.

"Assturbation?"

"Yeah."

"Well, from what I understand...if a boy doesn\'t have a girlfriend, his mom will allow him to stick his penis in her ass and get sexual release that way."

"Yeah, that\'s um...what I heard also."

"Is there a reason you\'re bringing it up to me?" his mom inquired, raising an eyebrow and smiling over at him teasingly.

"I was just wondering what your thoughts were on it."

"I think there are lots of exciting and pleasurable things a boy can do with his penis but putting it up his mother\'s butt IS NOT one of them," she expressed.

"So, you don\'t really like doing that kind of stuff?" Joey asked in disappointment.

"I didn\'t say that. I just mean that it shouldn\'t happen between a mother and her son, that\'s all," Cassie answered.

"Oh...um, I get it."

"Sorry, Kiddo," the mother consoled, reaching over to rub his knee. "I know you\'re single and it sucks, but you\'re gonna have to stick with your hand until you get a girlfriend."

"Will do," Joey muttered, majorly bummed out. He didn\'t really know what his mom\'s thoughts would be on the idea, but he had a feeling they wouldn\'t be favorable. His parents had a good marriage, and he highly doubted his mom would do something to jeopardize that. Still, even though she rejected the idea, it didn\'t hurt to try.

Later that afternoon, the family was at the park with friends for a cookout. The dads all manned the grill, cooking up the burgers and dogs, while the boys played basketball on the nearby court. Cassie stood with two other moms, Vanessa and Caroline, watching their younger children scurry around the

playground. It was a hot day, so the mothers all wore tank tops and shorts that fit snugly over their rounded bubble butts.

"You\'ll never believe what Joey asked me this morning," Cassie shared.

"Let me guess. He wants a motorcycle?" Caroline asked, brushing her platinum blonde hair back off her face.

"No, but I have a feeling that request is coming soon too," Cassie answered with a fearful expression. "He asked me if I knew what \'assturbation\' was."

"Well, it\'s about time," Vanessa uttered. "Wesley brought that up to me the day he turned eighteen."

"Benson and I had that talk about two months ago," Caroline added.

"You guys never told me this," Cassie complained. "I can\'t believe this is actually a thing. I mean, the whole idea is so ridiculously obscene."

"So was masturbation at one time. Now it\'s just common knowledge that most people do it," Vanessa pointed out. "Sometimes you have to just roll with what\'s popular, as long as it makes sense."

"Yes, but it doesn\'t make sense. Masturbation isn\'t the same as a boy sticking his penis inside his own mother\'s ass," Cassie retorted.

"It\'s a matter of perspective really, and what you see as being your responsibility as a mother," Caroline explained. "My number one priority is meeting the needs of my children. It took some negotiating, but Benson and I finally reached a compromise, and so far, it\'s working."

Cassie\'s eyes lit up. "Compromise? Caroline, are you telling me that you\'re letting Benson have anal sex with you?"

"Yes...but only once a week, that was the compromise. Thursday afternoon Susie has dance practice, so Benson and I have two-hours at the house alone to help him get some release. He knows not to ask me for it any other time."

"Wesley and I started with a similar arrangement," Vanessa added, "but now I\'m afraid it\'s turned into a \'every day\' thing."

"Jesus, both of you are letting your sons do this?!" Cassie exclaimed.

"Yes. Caroline\'s right. Masturbation is something for pubescent boys," Vanessa expressed. "Our sons are men now. They should be getting pleasure from women, and if they have no girlfriend, then it\'s a mother\'s duty to step up to the task and allowed them to use a part of our body for pleasure."

"You can\'t tell me that your husbands agreed to this?" Cassie asked, looking at them both in disbelief.

"When you give Joey a hug, do you tell your husband about it?" Caroline inquired.

"No, but that\'s a hug. We\'re talking about anal sex here. There\'s a big difference."

"Not really," Caroline muttered, shaking her head. "You\'re simply using a part of your body to HUG a part of your son\'s body. We don\'t need our husband\'s approval for that. If it was my vagina, that would be different story. THAT would be cheating."

"Are you guys actually getting pleasure from this?" Cassie asked.

Vanessa and Caroline looked at each other and snickered. "Really, Cassie...do you even have to ask?" Vanessa asked her.

"It\'s not the reason WHY we\'re giving our asses to the boys, but IT IS a pretty good side benefit," Caroline bragged.

Cassie went home feeling like a complete failure. She was being the prudish mother, who was letting her strict moral senses stand in the way of doing what could be best for her son. She knew the way boys bragged and that Joey must be having to endure listening to his friends boast about beating their dicks through their mothers\' assholes on a regular basis. She wished she could convince her husband that \'assturbation\' was a beneficial idea but knew that he came from a deeply religious background and would be absolutely sickened by her even entertaining the thought of anal sex with their son.

"What the fuck am I gonna do?" she thought, genuinely on the fence regarding what was best. Cassie believed deeply in fate. She would often resolve her conflicted feelings with a coin toss, wholeheartedly believing that however it turned out was the way it was truly meant to be.

The mother pulled a quarter from her purse. "Heads, and I forget all about this \'assturbation\' thing," she told herself out loud. "Tails...no pun intended...and I give my ass to Joey to use until he gets a girlfriend."

She flipped the coin into the air, and it landed on the ground with a CLINK. She stepped over and looked down to see which side was facing up.

The next day, Joey returned home from school. Cassie was right about the boys bragging. Most of the day her son was forced to listen to friends at school boast about fucking their moms up the ass. Some boys he knew even broke up with their girlfriends, just so they could get some hot tail from their mothers.

"Joey, is that you?" Cassie called from the workout room.

"Yeah, just me."

"I\'m just in here on the treadmill. Come in and talk to me."

"I would rather have a piece if your ass...but I guess a talk will do," he thought.

When Joey arrived in the doorway he froze in shock. His eyes nearly bugged out of his skull as he stared at his mom, who was walking on the treadmill. She was wearing the sexiest pink booty shorts he had ever seen. More than half her lovely round ass was hanging out of them.

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Cassie peeked over her shoulder, giving him a cute smile. "How was school, honey?" she asked.

"It was...um, ok I guess," he muttered.

His eyes were still glued to his mom\'s buttocks. It wagged alluringly with every step and her ass-flesh jiggled wonderfully.

"Any luck getting a girlfriend yet?" Cassie asked.

"No. There\'s a girl I like, but we\'re still just getting to know each other."

"So, she hasn\'t let you start POKING around at her quite yet?" the mother teased.

"No, not yet."

"Speaking of poking around," the mother said, drawing her son\'s attention to her eyes, "see anything back there you\'d like to sink your hard penis into?"

Joey could hardly believe his ears. "Well, yeah, but...I know you said the other day that it was off limits," he answered.

"I know what I said and that was really selfish of me," Cassie confessed. "I\'m your mom and that means when my boy\'s not getting his needs met, even if they are sexual, it\'s my job to step up and help him."

After the coin landed on tails, Cassie went over in her mind all the reasons that \'assturbation\' was right for her and her son. She then became determined to follow through with helping him.

Joey heart rate was increasing by the second. "So, does that mean that we\'re gonna...?"

"It does," she smiled, "with conditions."

"Conditions?"

"Yes, we have other people living here, Joey, including your father, who would divorce me if he knew I was doing this for you," she explained. "You can\'t just go around poking me in the butt whenever you feel like it."

"Understood."

"I know you masturbate a lot, so I wanna make sure you\'re using my ass at least once a day...until you get a girlfrienatteCassie promised.

"Wow! Once a day would be awesome!"

"This is a busy household, so the time of day we do it will most likely vary," his mom stated. "I\'ll need you to be on the ready mark all the time. There will be times that I\'ll just be throwing you some ass spur of the moment."

"I\'ll be ready," the boy blurted. Speaking of ready...Joey\'s cock was fully hard beneath his pants, drawing his mom\'s attention.

"I don\'t care If you brag to your friends. It sounds like most of them are stuffing their mom\'s assholes as well," Cassie remarked.

"Yes, most of them."

"Not a word to anyone else about it though, understand? If your father finds out you\'re pounding me up the shithole, we\'ll both be in trouble."

"Got it!" Joey assured her.

His mom clicked off the treadmill and stopped walking. "I think I\'ll finish this workout in your bedroom. Wanna help?" his mom winked, then stepped past him.

Joey watched her lovely bubble butt undulate atop her sexy legs as she made her way down the hallway. She paused for a moment and smiled back at him. "I know you have a big one, but you still might have a hard time reaching my ass from back there, honey," she joked.

"Oh, right," the muttered, snapped from his trance.

He followed her to his bedroom and his mom closed and locked the door behind them. He stood there for a moment, awkwardly watching her as she sat on his bed and slipped her dainty feet out of her workout sneakers. "Have you had anal sex with anyone before, honey?" she asked candidly.

"Regular sex, yes...but never anal sex."

"A woman\'s ass isn\'t like her pussy-hole. It doesn\'t self lubricate during intercourse," she explained. "Get the lube out of your nightstand and we\'ll put some on your boner."

"How did you know I had lube in there?"

"Honey, I\'m your mom...I know what\'s in your bedroom. Which reminds me, you have about four pairs of my panties in here. I need them back," she demanded, not seeming upset at all.

"OK, I\'ll round them all up today," Joey assured her, fetching his bottle of lube.

"Thank you," Cassie muttered as she stood up and peeled her booty shorts off.

Joey froze, staring at his mom\'s mound of Venus. She had a perfect triangle of thin pubic hair that crowned her cuntal cleavage. "Do you trim it that way?" he curiously asked.

Cassie looked down at her pussy and smiled. "Yes, it\'s called the martini-style trim."

"I like it."

"Thanks, honey...but I think what YOU need to be focused on is back here," she teased, turning around and displaying her thick bare ass.

"I don\'t mind focusing on that."

"Good, but why don\'t you take your pants off while you\'re staring. You\'ll have a hard time squeezing that boner inside me if it\'s still tucked in your pants," she giggled.

Joey quickly undressed. As he did, he noticed something round, pink and shiny peeking out from between his mom\'s meaty butt cheeks. "Is there something in your ass?" he asked.

"Yes. It\'s an anal plug. I knew from seeing the boners you\'ve been sporting every morning that you\'re much bigger than your father. I wanted to get my asshole used to being squeezed around something a little bigger that what it\'s used to."

"I see," the boy muttered, reminded of how un-fucking-believable her ass was gonna feel around his cock. He removed his briefs and his erection sprung upward at a perfect angle.

Cassie let out a tiny gasp as she saw her boy\'s naked cock for the first time since he was younger. That tiny penis she had remember had now sprouted into a bulky nine-inch hunk of cock-meat. Fat, bulging veins crisscrossed up the stalk, which was capped by a plump pinkish-purple knob.

"Well..." the mother sighed. "I certainly wasn\'t wrong in my assessment of how large you are."

She visually assessed that he was at least a few inches longer than her husband and much, much thicker. She had certainly taken cocks this size in her ass before, but not since college. "It might be uncomfortable at first, but I\'ll get used to it," she told herself.

"Let me show you how to properly lube yourself up, honey," the mother said, reaching out for the lube.

She squirted some on her hand, then began coating her son\'s erection with it. "The key to good anal sex is a properly lubricated erection," she explained. "While it\'s important to get the shaft, it\'s imperative to heavily coat your bulbous tip."

The teen watched in fascination as his mom coated his knob generously with slippery lubrication.

"Your crown will pop through the ring of my asshole a lot easier if it\'s heavily lubed up," she explained, then traced her long nails around the fringe of her boy\'s glans. "Do you see how the ridge flares out like this?"

"Uh-huh," Joey breathed, more turned on that he\'d ever been in his life.

"This is the part that\'ll be spreading my ass-walls the most, so it\'ll get the most friction," she explained. "Always make sure it\'s heavily coated."

"Got it," the boy sighed, his cock twitching in her hand.

"So...there are different ways we can do this. Doggy position is the most common, but for this first time I really want you to just be able to lay back, enjoy it and not have to stress of how you\'re performing. Let MOM do all the work this first time, ok?"

"Sure," Joey agreed. He never thought things would get this far, so he wasn\'t about to protest.

"Lay down on your back," Cassie directed, patting the bed.

Joey looked at the swell of her big breasts, still covered by her workout top. "Hey, mom...do you think I could see your boobs too?" he brazenly asked.

"Sure, but no touching them, ok? It\'s ass-only, Joey. I mean it," she reminded him.

"Understood."

Rather than take her top off, the mother lifted it up over her boobies, so the elastic hem crossed above them. Her fat round tits ballooned out from her chest, capped by thick wide areola and protuberant nipples. "Better?" she smiled.

"Can you shake them back and forth?"

"Joey!" she playfully scolded.

"Just once and I won\'t ask again."

"Fine...once!" she smiled, then rocked her heavy tits from side to side. She delighted in seeing her boy\'s eyes light up and decided to give him something a little extra. She bounced gracefully on her feet, making her mommy-melons leap up and down.

"Holy shit, that\'s awesome!" he sighed, his cock flexing in reaction.

"Glad you think so, and watch your language," she playfully scolded.

"Sorry, that was just...really incredible."

"Yeah, well...it\'s called \'assturbation\' not \'boobsterbation,\' so focus on the ass, not the tits" his mom giggled.

Joey sprawled out onto his back and watched his mom follow him onto the bed. Her big jugs hung down as she straddled his legs, facing away from him, so he was staring directly at her big unblemished ass. It hovered above his aching cock, and he could clearly see the pink jeweled base of her anal plug. "Can I pull it out?" he asked.

"No!" she giggled

"You told me to focus on your ass. That\'s what I\'m doing."

"I guess you\'re right. Go ahead then," she whispered.

He slipped the metal plug from her asshole, then watched the elastic ring of her anus clench closed. From this angle, he could also see his mom\'s shaved outer labium. He noticed how they were slightly peeled apart, and her thick inner flanges protruded out. "Do you want me to rub you between my ass cheeks before you stick it in?" Cassie asked, peeking back at him.

"Sure," the boy answered.

The mother sat up, trapping his boner in the crack of her ass. She swiveled her wide hips up and back, giving him a nice little bunny rub.

"That feels nice," the teen sighed, feeling his rigid dick slip through his mother\'s butt-crevice. It seemed almost surreal that he was staring at his own mom\'s naked derriere, and that she was

smothering his cock with it. Her butt-meat felt so amazing smothering his penis. He could feel the lips of her asshole dragging along the underside of his cock. "Oh, wow!" he gasped.

Cassie peeked back at him. "Don\'t get too excited, honey. You haven\'t even gotten through my back door yet," she giggled.

"Can I stick it in?"

"Ready when you are," she answered, raising up slightly.

Joey grasped his cock and fit his slippery knob to her asshole. As he thrust up, it popped from her butt-socket, plowing along her cuntal gash, then sticking out from in front of her crotch. "Fail!" his mother teased. She moved forward, slipping her cunt along the top of his cock. When Joey thought his knob had reached her butt-ring, he jabbed upward. Cassie let out a sharp gasp as his fat knob pierced her twat. Her vagina felt warm and wet with arousal.

"Wait...wrong hole, honey!" she blurted in a panic, reaching down and grasping onto his throbbing penis.

"Sorry," the boy blushed, feeling his mom drag his knob across her fleshy clitoris and back through her cuntal vestibule. Coated in a mix of lube, cunt-juice and pre-cum, his tip slipped along her perineum, then Cassie fit it to her butt-ring. Joey shuddered in delight, seeing his mom\'s pretty hand wrapped around the base of his boner. The way her big wedding ring sparkled reminded him of how wicked they were being behind his father\'s back. His dick looked so big and powerful pushing up between her rounded ass-cheek. He could feel her asshole beginning to stretch around his knob as it gained entry.

Cassie let out a cute little squeal as her son\'s bell tip popped inside her. She felt it mushroom against her clasping sphincter. She pushed her ass downward, making more cock-meat sink inside the tube of her ass. "There we go!" she mewled, pushing more of her ass-tract down around the stiffness of her boy\'s boner.

"Woah!" the teen gasped, feeling her anal walls clasping around the pink flesh of his dick. His knob sliced through her spongy walls, traveling deeper and deeper, way up into her rectum.

Cassie paused for a moment, letting her shit-hole adjust to such a massive cock. "Good grief, he\'s huge!" she thought. She had regularly engaged in anal sex with her husband, but already her son\'s boner had traveled much deeper than her husband\'s prick was able to. A tinge of guilt seeped into her mind, knowing how such a scene would sicken her husband and probably break his heart. "It\'s not like I\'m having a love affair. I\'m helping our son," she told herself, justifying her actions.

"Am I all the way in?" Joey asked, wondering if that was as deep as his dick could go.

"Maybe if I was a girl your age, honey," Cassie answered, smiling back over her shoulder. "I\'m not though. I\'m a mom, and we moms go all the way to the balls."

Joey watched his remaining cock-shaft sink inside his mom\'s obscenely stretched butthole, until it met the root of his cock. "Dang!" his voice quivered as he felt every inch of his young peter sheathed in his mom\'s hot anal orifice.

"Now, you just relax and let mom give you a nice tight ride in her caboose," Cassie cooed, then began slowly raising and lowering her rounded ass on him.

"Wow!" Joey exclaimed, watching his slippery boner emerge, then disappear through the ring of his mom\'s asshole.

For several wonderful minutes not a word was said as the loving mother skillfully worked her ass on him. Her big jutting boobs wobbled heavily on her chest to her steady cock-humping motions.

Inside her ass, Joey\'s cock flexed and tingled, feeling her smooth rubbery ass-walls gliding along his tender penile flesh. Cassie repeatedly flexed her anal muscles, compressing her shit-tube even tighter around her boy\'s purple-headed warrior. The teen\'s drooling knob plunged deep into her bowels, feeling the neck of her rectal ampulla gnaw wetly at his glans.

"Oh, God!" he sighed, marveling at how wonderful his mom\'s ass felt.

The boy wasn\'t the only one feeling good. April had forgotten just how amazing deep anal penetration could be. Waves of wonderful pleasure surged through her heavy-titted body each time her boy\'s cock plunged through the tube of her ass. "Fuck!" her mind gasped. "It\'s been so long since I\'ve had such a young dick like this. It\'s so fucking hard!"

Cassie peeked back at him with a pleasure-filled smile. "Is that what you wanted, honey? Did you want mom\'s ass to milk your boner, just like the other boys\' moms were doing to their dicks?" she cooed.

"Yes...it feels amazing!" he replied.

"Tomorrow I\'ll get on my tummy and let you climb on top of ME. I\'ll let you really pound your boner through my asshole as hard and fast as you want."

"Oh, man...that sounds awesome!" the boy exclaimed.

"Yeah? Won\'t that feel good slapping your crotch against mom\'s big rippling ass-cheeks?"

"Heck yes!"

"Sometimes, I\'ll get on my hands and knees and let you mount me from behind," Cassie said in a sexy tone. "You can watch mom\'s big boobies swing around while you smash your big young cock up my shit-hole."

Joey couldn\'t believe his mom was talking to him this way. He certainly wasn\'t complaining. It made his cock tingle even more.

Cassie slapped her fleshy, rounded buns down against his crotch and held him there in full penetration. Then, she began gyrating her hips like a hula dancer, stirring his prick in her clutching ass.

"Ahhh!" the teen shuddered. He didn\'t know what the fleshy parts were that his knob was digging around against, but whatever it was felt out of this world.

"Maybe I\'ll let you pick me up some days, pin me again the wall and fuck up into my ass, while I cling onto you," Cassie stated in a sensual tone. "Of course...that would mean that my big naked tits would have to be crushed against your bare chest. You wouldn\'t mind that, would you, honey?"

"God, no!" the boy sighed.

She began bouncing up and down again, even more vigorously this time, pumping her asshole down around his satisfying stiffness. The pleasure-stricken teen watched her round bubble butt SMACK against his pubic-base repeatedly. The fatty flesh of her ass-meat rippled wonderfully on every strike.

"Do you have some cummies for me, Joey?" his mom asked breathlessly. "Are you gonna throw some ropes inside mommy\'s tight cock-stroking ass?"

The incredible feel of her ass, coupled with her dirty words made Joey\'s prostate swell. Cassie felt his prick mushroom even bigger and give off pre-orgasmic contractions. She really started pounding the hell out of him, screwing the elastic ring of her butthole to his cock-root on every plunge. She beat her big mommy-butt against him feverishly, feeling his thick, excited cock thunder through her ass-tract. Like a good cock-humping mother, she flexed her shit muscles, squeezing the tubular flesh of his penis as tightly as she could to give him a cum he\'d never forget.

"AHHH, MOM!!" the teen grunted, humping with involuntary thrusts beneath her. Thick spurts of ball-juice began hosing out his ass-smothered meatus. He came so fucking hard he thought he might pass out. For nearly ten minutes his mom made little sexy whimpering sounds, making her rectum chew and pull at his cock, milking every ounce of cum from his twitching penis.

Finally, she lifted her butt, making his dick slowly worm out of her asshole. His knob popped wetly from her butt-socket, and his dick smacked stiffly back against his abdomen. He watched the cum ooze from his mom\'s puckering anal ring, before it clenched closed completely.

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"How was that for some \'assturbation,\' honey?" Cassie asked, peeking back with a smile.

"Insanely good!" he answered with a deep satisfied sigh.

"Now...I don\'t want the fact that I\'m doing this to detour you from getting a girlfriend," she preached. "Mommy\'s ass can\'t go to prom with you."

Her comment made her son laugh. "No, but it could be waiting for me AFTER the prom," he stated.

"Hmm, interesting thought," she said with a mischievous grin. "Banging mom\'s butt in the backseat of your car up on Lover\'s Hill," she suggested, talking about the local make-out spot.

"Sounds fun to me," her boy beamed.

"Maybe I\'ll wear my prom dress, from MY high school days," Cassie suggested.

"Heck yeah! You could attack me like you did dad on YOUR prom night."

His mom bit her bottom lip, gazing at him lustfully. "You better be ready for an all-nighter then,\' she expressed. "You\'ll load me up with so much jizz I\'ll be shitting cum for a week!"

They both laughed.