Mother's Shoe Mystery Pt. 15

It was 5th period for Billy, and he had been struggling to concentrate all day at school. He used to think about sex a lot, but now it consumed most of his thoughts. He had gone from being a virgin a short time ago, to fucking his own hot mother, and his best friends hot mother. He had also gotten blow jobs from both of them as well as his grandmother. He kept thinking about all the things he wanted to do with them. He was also thinking about how just the day before, he had licked his mothers piss slicked pussy, and he loved every second.

Billy was also excited that his sexy grandma was going to introduce him to her bridge club tonight. He had never met any of her friends but he had seen a picture of all of them together in his grandmother's house, and he knew right away he would fuck all of them. He had taken that picture into his grandmother's bathroom a few time in the past, and jacked off to the image of a group of grannies wearing summer dresses. He would picture himself eating all of them out before bending them each over and fucking them with his young cock.

It also didn't help that he was in Mrs.Bonnaire's French class. She was 49, with short brown hair that was greying a lot. She had amazing legs, and a shapely ass, hat Billy would stare at all the time. She always wears pumps too, and always dangles one off her foot, while she sits at her desk. Billy fantasized so many times about smelling her pump, and licking it to get her foot taste on his tongue. He had always known that was never going to happen, but lately Billy had a lot of his fantasies come true. "Why not this one?" he thought.

Suddenly Billy's sex thoughts were interrupted by the classroom door opening. One of the school's office aids walked in with a note, and handed it to the teacher. Mrs.Bonnaire thanked the aid, and then looked at Billy.

"Billy, please come to the front," Mrs.Bonnaire said, with concern in her voice.

Billy got nervous, not knowing what all this could be about. He made his way to the front.

"What is it Mrs.Bonnaire?"

"Billy, your mother is here to pick you up. I don't know the situation, but apparently there is a family emergency, and she needs you to leave with her right now."

Immediately Billy thought something must be wrong with his grandma. He made his way out of class, and ran through the hallway, and across the quad, making his way to the front of the school. He saw his mother Peggy parked along the curb. He ran over and jumped in the car.

"Mom, whats wrong with grandma? Is she OK?!"

"Calm down Billy, your grandma is fine."

Peggy began to drive out of the front of the school.

Billy was confused since his mother wasn't telling him what the emergency was.

"Mom, please tell me what's wrong! Why did you pull me out of school? Where are we going?"

"We are not going far Billy. Don't worry. Everything is fine."

Billy realized his mother had driven around the block to the back entrance of the school. It was a big parking lot that was only really used when his high school's football team had home games. The parking lot would fill up with spectators. But other than that, it stayed empty. The lot was adjacent to the track that surrounded the football field. From the lot you could see the back, and underside of the bleachers, which partially blocked the view of the field.

"Mom, why did you drive us here?

Peggy looked at Billy with a hungry look in her face.

"My little baby boy. I couldn't stop thinking about you at work, and I know you are going out for a while with your grandma tonight, and I will be out with the girls really late. My cravings are too strong. I knew I couldn't go that long without sucking your cock. I'm so hungry for your cum baby. I had to come get you. I decided to come here on my lunch break. I told my boss I would take an extra long one."

"You came all the way here, and pulled me out of school, so you can suck my cock?"

"Yes baby. I have become a slut for your cum. I'm your own, personal, mommy cum slut. I love the jars of cum you prepare me for lunch, but I still prefer getting it straight from the tap."

They both laughed, and then Peggy looked down to see the bulge in Billy's jeans.

"Mmmm, there it is. There is my son's big, veiny, fat, beautiful cock, just dying to burst out. Let me help him."

Peggy undid Billy's jeans button, and the pulled down his zipper. She told Billy to lift his hips and she pulled his jeans and boxer shorts down to his knees. She grabbed his hardening cock and began to stoke it. She still marveled at her young son's perfect cock. She increased her stroking speed, and Billy began moaning. Periodically Peggy looked through her car windows to see if anyone was coming. While she was doing that she saw that the girls track team had started practice. From the cars view, she could see a quarter of the track, but the rest was obscured by the bleachers. The girls started doing laps and it caught Peggy's attention. Peggy may not have been focusing on Billy's cock at the moment, but she kept stroking him expertly. Billy realized her gazing at the track.

"What is it mommy? Why are you staring at the girls running?

Peggy kept looking at the track, and finally she spoke.

"Isn't that cute blonde over there, with the red headband, Rena?"

Billy looked over and tried to see who his mother was talking about. He finally got to see the girl she was talking about, and it sure was Rena.

"Yup, that's her mom. Why do you ask?"

"Don't you have a crush on her Billy? Didn't you tell me you thought she was the hottest girl in school."

It was true. Billy had wanted Rena for years, but he never had the guts to ask her out. A few times he had snuck into the girls locker room, and gone into Rena's locker. He had guessed her locker combo was her birthday , and he was right. He had gone in her bag, and sucked her sweaty, post track practice, underwear. Once he had gotten bold and took his fat cock out. He took her sweaty underwear, and draped it on his cock rubbing the inside along his shaft. He had nearly cum, and had to stop himself just sort of it.

Peggy could see Billy was nervous to say it, probably thinking she would get jealous, but in truth, Peggy thought it was hot. She began to think how much she would love to see two young people fucking, especially her son, and the hot piece of ass teen girl that was now making her wet, just by seeing her little shorts ride up her tight little ass. Peggy looked over at her son again.

"Billy, I'm going to stat blowing you, and while I do, I want you to think about taking off Rena's shorts and underwear, and wringing the sweat out into your mouth, and then fucking her with your young cock. Keep your eyes on her sexy body, running and getting very sweaty, just for you."

Billy gave a little smile.

"OK mommy, if you're sure."

Peggy lowered her head and began licking the whole length of Billy's shaft, from just under the tip, down to his balls. Peggy loved the musky smell of her son's big balls. She gave them a few licks, and then sucked one into her mouth. It hurt Billy a little, and he jumped a bit, but he loved it. She then began sucking his cock, and swirling her tongue around his massive cock head, Billy put his hand on the back of his mother's head pushing her head don on to his cock with more force. He kept his gaze on Rena running on the track, and began picturing her sucking his cock. He imagined how good her pussy and ass would taste after a track meet. He would spread her ass cheeks and breathe in deep.

While Billy was lost in fantasy, Peggy was bobbing her head on her son's 9 inch cock. She loved the feel of it in her mouth, and she had gotten much better at deep-throating. She couldn't get enough of his gorgeous, vascular cock. She stopped sucking his cock and began giving him a hand job so she could speak to Billy.

"You still watching Rena baby? You still thinking about fucking her? You probably want to fuck her more than anyone."

Billy continued staring at the track, but he answered his mother.

"I do want to fuck her really bad mommy. But she is not the one I want to fuck most in the world. That would be you mommy. It will always be you."

Peggy slowed her cock stroking pace without realizing. What Billy had just said made her want to cry. He had just said, and she believed he was telling the truth, that she would always be number one for him, no matter what other girl, or woman, came into his life. Peggy kept stroking Billy with her right hand, and reached up to his face with her left and grabbed him by the chin, turning his head to face her.

"I love you Billy."

Billy looked at his gorgeous mother, and knew he was the luckiest son in the world.

"I love you too mommy."

Peggy stared at him for a few moments before moving in and planting a deep, passionate kiss on her son. Their tongues danced together and Billy instinctively reached around and cupped his mothers ass. Mother and son made out for a good 5 minutes until Peggy pulled away. She stared at Billy's eyes for a few seconds.

"Billy, get in the back seat with me."

Peggy got out of her car and climbed back into the back seat. Billy zipped up, and did the same. When Billy got back in he noticed for the first time that his mother was wearing black stockings and high heels, just like Mrs.DiNucci had for their date. Seeing his mother wearing that made his cock fully hard instantly. It was also hot that she was wearing a very short skirt.

"Billy, I think it's time."

"Time for what mommy?"

Peggy turned her body away from Billy, so she was leaning against the back rest her backside facing Billy. She lifted her skirt, exposing her panty-covered ass.

"It's time, my young stud boy, for mommy to give her ass for you to fuck."

Billy gave his mother a look of ecstatic surprise.

"Really mommy?! I'm really going to finally get to fuck your ass?!"

Peggy turned her head around to look at Billy with a big smile.

"Yes baby boy. You have given mommy so much pleasure, and licked her ass so good, it's about time for mommy to give you what you have wanted for so long."

Billy had the biggest smile on his face, and kept thanking his mother for what she was about to let him do.

"You don't have to keep thanking me baby. But a few things before we start. First, you need to go slow, and just start with your cock-head. Your cock is way too thick and long for you to just ram it in. Mommy hasn't had anal sex since right out of high school, and my asshole is very tight. Secondly, you are too big to go all the way in at any point. Mommy can't handle all 9 inches you are packing, so at most, put half your cock in. Third, don't pull out when you orgasm. Mommy wants you to fill her rectum with your warm, incestuous, boy cum. Think you can follow those rules, stud?"

"Oh yes mommy. Anything you say!"

Peggy lowered her panties and slipped them over her high heel pumps, and put them on the car seat next to her. She reached behind her to her bubble butt with her right hand and spread her right ass cheek, exposing her tight, brown asshole.

"Oh one more thing Billy. I haven't showered for two days, so there might be some smell."

Peggy winked at her excited son, who was now smiling bigger than ever.

"Thank you so much for not showering mommy!"

"You're welcome baby boy. Now, before you start, spit on your cock, so that you can lube it up, and not hurt mommy with a dry ass fucking. Mommy's asshole is sweaty, but not enough for the monster you are about to put in it."

Billy did as he was asked, and lubed up his cock thoroughly with his spit. He turned sideways so match his mother's position, and arched his hips forward, placing his cock just outside her asshole. His mother wasn't kidding about the smell from her unwashed ass, and he loved it.

"You ready mommy?"

"I am baby. Remember to start slow."

Billy placed his right hand over his mother's hand, helping to spread her ass cheek even further. He could feel his mother's body tense up in preparation for his cock to penetrate her asshole. Billy slowly pushed his cock forward until the tip made contact with her asshole opening. He hesitated for a moment, fearing he would hurt his mother. Realizing his hesitation Peggy reassured him.

"Don't be afraid Billy. Mommy wants this so bad. Mommy's asshole is hungry for your cock. Do it baby, please."

Given the final go-ahead Billy pushed his cock-head into his mothers incredibly tight asshole, stretching it wider than it had ever been stretched. It wrapped tight around his cock head. Peggy let out a moan of pain. If his fat cock-head was causing this much pain, she had no idea how she'd be able to take his thick shaft too, but no matter what, she would. Billy withdrew his cock-head again and repeated his penetration. It felt amazing to him, feeling his mother's dirty, smelly, sweaty asshole, suctioning on to the head of his cock. After a couple minutes Peggy knew Billy needed to be encouraged to go further.

"Billy, mommy is ready for you to give her more of your perfect dick. Give me some of your shaft."

Billy slowly penetrated her once more, this time pushing until about 3 inches of his cock were in her. Peggy began moaning in pleasure and pain. Her son's cock was stretching her anal walls, and she could feel every vein and ridge of his cock against them. Billy was in pure ecstasy. It was the first time he was having anal sex, and he instantly loved it. He had dreamed about putting his dick in his mother's ass since he was very young, and now it was finally happening. He kept his slow rhythm for a while, but his animal instincts kicked in and his speed increased, as well as his depth of penetration into his mother's anus. He was now pumping fairly fast, and going in about 7 inches deep. Peggy started screaming now, and was trying to deal with the pain of being anally rammed by her son's huge cock, for his benefit, but finally she couldn't take anymore.

"Slow down there stud. You are going to rip mommy's rectum apart. Just take it nice and slow, and give me one less inch."

Billy immediately adjusted his speed, and penetration depth.

"Mmmmmm. Much better baby. Now mommy can really enjoy the ass fucking. You getting close to cumming baby?"

"Yes mommy. I'm really close I think."

"Well, mommy is loving the ass fucking, but her asshole is getting sore, so let me help get you there a little quicker."

Peggy reached down and pulled her right high-heel pump off her foot and put it over her shoulder.

"Take my pump Billy. Mommy's feet have been sweating in these stockings all day, and I haven't aired out my heels today. They smell so bad, the way you love them. Bury your nose in the pump, and keep ass-fucking me until you cum."

Billy did not hesitate in grabbing the pump from her hand and burying his nose as far as he could into it, breathing in her sweaty foot smell, and licking around the inside of it. Even more of Billy's pleasure centers were hit, and he felt his orgasm building. Peggy could feel him starting to tense up and pump the way he does every time he is about to cum.

"Remember baby, cum deep in mommy's asshole."

Billy was breathing hard and he began pumping slightly faster.

"Mommy, it's happening. I'm going to...Uggghhhhhhh Fuck!!"

Billy pushed all 9 inches in as his cock exploded, sloshing into his mother's rectum, and coating her anal walls with his copious amounts of cum. Peggy yelp at the sudden pleasure and pain of her son's full 9 inch cock buried all the way to the hilt inside her ass. She felt jet seam after jet stream filling her. After a good 20 seconds of cumming Bily withdrew his cock and fell back onto the car seat exhausted.

"Oh mommy, that was, fucking... fucking amazing!"

Peggy looked back at her son and winked.

"It sure was lover."

She grabbed her panties and quickly slipped them all the way on.

"Mommy doesn't want any of your cum to drip out. I'm going to keep your cum inside my asshole when I go back to work. I want to feel your cock cream inside my ass, all day."

Billy didn't know what to say, he just smiled at his mother.

"So baby boy, does it turn you on that your cock smells like your mommy's stinky asshole?"

"Fuck yeah mommy! I love your ass smell so much. I want it on my dick all the time!"

"Well you are going with your grandma to visit her bridge club friends tonight, so you need to ower up. Ill drop you off at home, and then head to work."

"Sounds like a plan mommy."

Peggy slowly got out of the car, her ass sorer than it had ever been. Billy joined her in the front, and they drove home. Peggy headed back to work, the whole time feeling incredibly turned on having her anus filled with her young son's cum.

Billy showered, and played video games until a few hours later when the doorbell rang. He hurried down stairs and opened the door. Standing there was his grandmother Claire, wearing a micro-mini skirt and high heels. She was wearing a silk blouse with the buttons so low, Billy could easily see her beautiful breasts in a lace bra. Billy's cock got hard, and he wanted to pull his grandmother inside and finally get to fuck her. But he didn't want to presume his grandmother was ready for that.

"Hi Billy!" Claire said before quickly noticing the tent in his pants.

"It makes me so happy that granny can make you so excite so quick! You like what I'm wearing?"

Billy was starting to drool.

"Fuck yes grandma! You look so fucking hot!"

Claire started blushing. The thought of her hot grandson wanting her turned her on like she never had been before in her life.

"Grandma would love nothing more than to pull your pants down right now, and suck your magnificent cock until you filled my mouth with your sweet cum for me to swallow. But I we are running late, and the ladies are anxious to meet you, so calm your trouser snake down, and let's head out."

Billy made the mistake of staring at his grandmother's ass as he followed her towards his car, ensuring his hard-on was not going away anytime soon. His grandmother's car was in the shop so she took a cab over to his place so he could drive them both over. They chit-chatted on the 20 minute drive. Once they got there, they hurried up inside. Sitting at a table were Claire's friends. They all immediately began to check out the young stud their friend brought in. Claire began introducing them.

"Ladies, this is my grandson Billy."

Billy moved forward to shake each of their hands around the table as they were introduced to him. These were the grannies in the picture Billy used to jack off, and they were so hot. He couldn't help the hard-on that popped up. He tried to pretend it wasn't there. Maybe they wouldn't look down. Billy was wrong.

"Billy this is Janine."

Billy shook her hand and saw that her eyes went down to his crotch, her eyes widening atthe huge tent his cock was making.

Next Billy was introduced to Gina. Gina looked up at Billy, and it was clear she was trying hard not to stare down at his pants.

Following her was Betty. She shook his hand and smiled at him.

"Your grandma told us she had a hot grandson, and she was right."

Theresa also smiled at Billy and shook his hand. She seemed to have no problems keeping eye contact and not taking a peek at his obvious erection.

Last up was Gloria. She had been caught by Claire fucking her own grandson in the back of the bridge club last week, and it had only fueled Claire's fantasies about doing that with Billy, even further. Gloria gave a very seductive look to Billy, and without hesitation, looked at Billy's crotch and licked her lips.

"Very nice Billy." Was all she said.

Billy walked back and stood next to his grandma. Theresa and Betty both discretely started rubbing their own pussies through their pants while staring at Billy. Gina then spoke.