Anal Runs in the Family

bywalterio©

DATING JUDY

The next morning Matt woke up, showered and dressed. He was eating some cereal when the phone rang. It was his quasi girl friend Gail.

"Well what have you got to say for yourself," Gail yelled into the phone.

"Good morning to you too, what are you talking about?"

"Have fun at the party last night?"

"Oh, yeah, it was okay. I was at Joe's house and we got invited over."

"Don't you want to tell me something? I heard that you and Judy hit it off."

"So we danced, so what?" Matt snapped now annoyed at the interrogation.

"Pretty close from what I hear and you kissed her."

Matt wanted to say, "Right and I also ate her pussy and she gave me a hand job." However he restrained himself and replied, "Well you seem to have all the information, what do you want me to say?"

"An apology would be nice."

"Christ Gail it's not like you aren't dating other guys. Nothing happened so I'm not apologizing. In fact if you must know, I'm taking Judy to a movie this evening."

Gail slammed the phone down and Matt hung up. "Bitch," he whispered. He poured a cup of coffee and sat in the family room. He and Gail still dated but they also dated others particularly at college. Gail was an okay sex partner but nothing Matt was going to miss if she cut him off. Besides he was already thinking about Judy's super fine ass and fantasizing about fucking it.

That evening Matt took Judy to the movie and afterward they went a popular make out spot. Judy was wearing a blouse and a mini skirt and before long her blouse and bra was pushed up over her tits. Matt sucked her tits and stroked her thighs. He moved his hand inside her panties and stroked her clit. Judy went wild and humped his hand. Matt then eased her panties down and off her legs, moved between her legs and positioned them over his shoulders. Judy was shaking in anticipation as Matt began to lick her pussy and cupped her beautiful ass cheeks. Judy came numerous times humping her pussy against Matt's face and soaking him with her cum.

Matt moved up along side Judy and kissed her deeply allowing her to taste her own pussy juice. She wanted to reciprocate again so Matt steered her petite hands to his exposed engorged cock. Judy stared at it in awe before she began stroking it. Matt then guided her through other techniques and soon had Judy licking and kissing his cock. He moved her to the next level of sucking the head of his big cock and fondling his cum filled balls. Judy started to get into it and tried to take more and more of his cock in her mouth. Matt could feel his orgasm building but elected not to warn Judy.

His first burst of cum caught her totally by surprise and when she felt the second burst she tried to swallow the first. Her mouth quickly filled with cum and to prevent gagging she pulled his cock from her mouth. Matt's cock kept firing cum and it hit her in the face, hair and bare tits. Judy giggled as she held the spurting cock in her hands as Matt's cum flew everywhere.

Matt and Judy continued to date and went out every evening that week. The next several dates were repeat performances and Judy had become comfortable with both of them being totally naked. Matt added variations to their sex. He taught her about sixty-nine so they could eat each other together. He also introduced his finger into her asshole as he ate her pussy. He placed Judy on all fours, licked her pussy and rimmed her asshole. One night he placed just the head of his cock in her pussy and rubbed her clit with the soft head of his cock. Judy went wild and had multiple orgasms.

Judy told Matt that she was ready to fuck but not in his car. Judy told Matt that her mother would be gone all day the following Monday so they planned to get together then. That Monday Matt waited patiently for Judy's call and when she phoned, Matt headed for her house.

They were both anxious to be naked in bed and Judy was determined to lose her virginity. With Judy lying back on her bed, Matt slid between her legs and was gentle and patient as he eased his throbbing cock into her pussy. The pressure of his fullness almost negated the pain of losing her virginity. The pain soon subsided and Judy only felt pleasure as the large cock touched every fiber of her cunt. Matt fucked her slowly with long deep strokes and Judy began to hump her cunt up at him. She had numerous orgasms with the last ones violent and vocal. Matt tensed and flooded her pussy to overflowing with his cum. He continued to pump her pussy and she could feel cum running out of her cunt and trickling down her thighs. Judy held Matt tightly as she felt she was in heaven.

The rest of the day they showered, had more sex and stayed naked all day. At one point they took a bath together in a Roman style whirlpool tub. After the bath Matt gave Judy's body a massage with bath oil. First he massaged the front of her body paying special attention to her tiny tits and her pussy. Sensing that she was on the verge of another orgasm he slipped his cock into her cunt and Judy humped herself into frenzy.

Matt then rolled Judy over on her stomach and massaged her back, shoulders and the back of legs. He kneaded her gorgeous ass cheeks and as he massaged her ass he put an ample amount of oil on her asshole. Then Matt began to probe her asshole first with one and then two fingers. Before long his fingers were moving easily in and out of Judy's thoroughly lubed asshole. He lifted Judy up by her hips until her ass was in the air as she rested her head on the mattress. He removed his fingers and positioned the head of his cock at the entrance to her ass. As he eased his cock into her bunghole he heard Judy gasp and hold her breath. He assuredly told her to relax and that he would not hurt her.

As Matt eased his cock into her ass the head cleared her sphincter as Judy uttered an audible gasp. He continued to ease his cock in and out of her asshole feeding her an additional ¼ to ½ inch at a time, each time waiting until she relaxed. It seemed to take hours before his entire 8+" were lodged deep in her ass. If he had not cum so many times already he would have shot his wad quickly. He started to fuck her with long deliberate strokes as he admired her beautiful ass accepting his huge cock. Matt stroked her marvelous ass cheeks and told her how good she looked in this position with his dick skewering her luscious ass.

Matt felt his orgasm start down in his balls and rush up through his cock flooding Judy's rectum. He came more than he expected and his cum soon filled her asshole to overflowing and backed up coating his cock and running down the inside of her thighs. They both collapsed on her bed and rolled to their sides with Matt's cock still imbedded in Judy's ass. His cock softened and slipped from her asshole with an audile pop.

After that day Judy could not get enough of Matt's cock and Matt could no get enough of her incredible ass. Every time Judy's mother left the house Matt was over to fuck the daylights out of Judy. Judy was insatiable and she became reckless which is how they were discovered by Heather. Then it was Heather's turn to be coy and fake that she was leaving so that she could watch her daughter and her stud. Heather never suspected she had been discovered but Matt knew that she was spying on him and Judy.

NAILING HEATHER

One very hot Tuesday afternoon Heather was sunning by her swimming pool. Judy had invited Matt over but neglected to tell her mother. Matt arrived and headed right for the pool in the back yard. He spotted Heather lying on her stomach with her beautiful ass on display. She was wearing a thong bikini and her lotion covered buns glistened in the sunlight. Her bikini top was untied and Matt just stared at her beauty. Now he witnessed exactly what Joe had talked about.

Instead of going inside to look for Judy, he approached Heather. He sat on a lounge next to her and stared at her lovely ass. He knew that she had been watching he and Judy have sex and he often wondered why she had never put a stop to it. He assumed that it turned her on to watch her own daughter get her ass fucked. Matt wondered if Heather had even been butt fucked because she sure had the ass for it. He reached over and trailed his hand lightly over her buttocks.

Heather had dozed but she was not in a deep sleep. She felt the light caresses on her bottom and at first she thought it was perspiration running down her buttocks. She then felt the light lift on one cheek and she realized she was not alone. She snapped her head around and spotted Matt fondling her ass. Heather sat up quickly forgetting about her untied bikini top.

"Matt, what the hell are you doing? Where's Judy?"

"She's in the house. I just got here. You have a beautiful ass Mrs. Van."

Heather realized she was sitting up with her breasts exposed and she quickly grabbed the bikini top and put it on. "You need to leave," she scolded.

"You have nice tits too."

"Stop it, and got away from me."

"Oh come on Mrs. Van. I know that you have been watching Judy and me for days now. My guess is that you would like to have some of what your daughter is getting."

"That's not true," Heather stammered but she knew she was busted. Her embarrassment was obvious even with her golden tan.

"It's true all right. I want you to promise me that we'll get together when Judy's not around and then I'll leave."

"You're insane."

"Promise me," Matt insisted and then he pulled his swim suit to one side and freed his erection. "See what is waiting for you, promise."

Heather dropped her head and nodded she agreed. "Good," Matt said and then he put his dick away and headed to the house. "I'll get Judy."

Heather pulled a sarong around her body and waited for matt to leave before she went in her house. She changed into a tasteful two piece swim suit and later joined Matt and Judy by the pool. All day Heather kept thinking about Matt and his assertive behavior. She also could not get the image of him flashing his cock out of her mind. It would be a few days before Judy was out with her friends and Heather would call Matt but what a day it would prove to be.

On Thursday Judy and her friends went to the beach and they would be gone all day. Matt arrived at the house and Heather acted like a virgin on her wedding night. Anxious to get started, Matt took Heather by the hand and told her, "Lead the way to your bedroom."

Heather walked ahead of Matt and as she ascended the stairs Matt watched her marvelous ass undulate in her tight slacks. Heather walked into her bedroom with Matt right behind her and then she turned to face him. She was about to speak and tell him she changed her mind when he stepped up to her and kissed her driving his tongue into her mouth. She had not been kissed that passionately in a very long time.

Matt began to undress Heather as she stood still and trembled as her clothing was removed. Matt first removed her blouse, then her shoes and her slacks. Heather stood wearing only her bra and panties and Matt like what he saw. Matt stepped up behind Heather and unhooked her bra. Then he slowly pushed it down her arms and Heather instinctively covered her breasts with her hands. Matt massaged Heather's neck and shoulders gently as if he was trying to remove her tension. Then his hands encircled her waist and he kissed her neck. Heather trembled and goose bumps covered her skin. Matt's hands moved upwards and he cupped her breasts. He fondled them gently and toyed with her erect nipples. Heather could feel her body heating up and she felt like she was a teenager once again.

Matt then dropped to his knees behind Heather and began to pull her panties down. First he uncovered her buttocks and he kneaded them gently in his hands. Then he lovingly placed kisses on each of Heather's ass cheeks and let his tongue tickle her crack. Heather gasped aloud when the tongue slid over her crack and Heather sensed that Matt was experienced beyond his years. Heather realized then why Judy had been no match for Matt's seductive powers. Heather then felt her panties pulled all the way down her legs and she stepped out of them. Now completely naked Matt turned Heather around so that she faced her kneeling lover. Matt touched Heather all her around her vulva and probed her vagina gently with his fingers.

Heather's pussy was sopping wet by now and Heather was shocked when Matt moved in closer to lick her pussy. Heather groaned and shivered as the tongue danced over her labia and then she almost collapsed when the tongue found her clit. Matt pushed two fingers into her pussy and quickly located her g-spot. Then he massaged her g-spot and nibbled on her clit simultaneously. Heather lost it and she grasped Matt's head and held him tightly as her juices poured into his mouth. Heather almost lost her balance, her orgasm was so intense and she seemed to cum for minutes. Then Matt stood up and Heather saw his face coated with her love juice. Matt kissed her again and she tasted herself.

"Now it it's your turn," Matt said with all the confidence in the world.

Heather then realized that Matt expected her to undress him. She hesitated for a moment since she had never undressed a man in her life. Then Heather stepped up to Matt and pulled the tight t-shirt out of his pants and lifted it up over his body. Heather marveled at the chiseled physique of the young man. Then she unbuckled his belt and unfastened his pants. Matt then put his arms around her and hugged her tightly crushing her breasts against his hairy chest.

"You have great tits, Mrs. C," Matt whispered to her.

Then she stepped away and kneeling down in the process, she pulled Matt's pants down to his ankles. Matt kicked off his shoes and then stepped out of his pants. Now he was just wearing his underwear briefs but his package was prominently outlined. Heather's hands were shaking as she hooked her fingers in the waistband of Matt's briefs and slowly pulled them down.

Matt's impressive cock got caught in the waistband momentarily and then it sprung out like a coiled snake. Heather gasped when she saw the big cock bob in front of her face. Matt's cock was big but it was not huge. However at 8+" long and a little more than 5" around it was the biggest cock that Heather had ever seen and it looked menacing to her. She briefly recalled her husband's cock which was more the average size of 6" and not as thick. Heather just stared at the cock in front of her as Matt kicked off his underwear.

Matt reached for Heather's head and held it gently as he guided her face toward his cock. Heather knew that she was expected to take Matt's cock in her mouth but she was reluctant. Heather had only performed oral sex on her husband and that was in an effort to get him hard or to get him interested in sex. No one had ever cum in her mouth in her life. Heather let Matt guide her face to his cock and she opened her mouth wide to receive the impressive organ. The big fleshy mushroom head filled her mouth and she knew that she would never be able to take all of him in her mouth. Heather was inexperienced in oral sex but she tried to hide that from Matt. She bobbed her head up and down on the stiff shaft taking about half of it in her mouth.

Heather actually liked the soft feel of the mushroom head rubbing against the roof of her mouth as she sucked the thick cock. Matt then held her head gently and caressed her hair as Heather sucked him. Matt was very turned on and he knew that he would not last long. Matt felt his ball sac tighten and the pressure build in his scrotum. He opted not to tell Heather that he was close to cumming but instead held her head more firmly. Then Matt felt it and he ejaculated into Heather's mouth with such force that it startled her.

Heather tried to pull her head off of Matt's cock but he held her head tightly as jets of cum shot into her mouth. Heather felt the first jolt hit the back of her throat and before she could react, a second round shot in her mouth. Heather tried to expel the semen as quickly as she could without swallowing any and it ran out of her mouth covering Matt's shaft and flowing over his testicles. Matt kept shooting cum into Heather's mouth and she quickly learned to use her tongue to block the discharging cock. Six forceful jets were shot into her mouth and then the cock just oozed its remaining discharge. In spite of her efforts, Heather ended up swallowing some of Matt's semen. She at first was repulsed by the act but then she thought that the semen hadn't tasted that bad.

Matt's cock and balls were cum covered when Heather finally removed his cock from her mouth. She stared at the imposing weapon that had just ejaculated in her mouth and it was still as hard as steel. Heather felt Matt's hands on her pulling her to her feet and then he kissed her deeply. Heather was surprised that Matt would kiss her after she sucked his cock but he seemed unconcerned about the traces of semen in her mouth. Matt guided Heather over to her bed and had her lie on her back. Matt raised himself up and knelt between her legs. His huge cock looked menacing as it hovered above her hips. Matt held his cock and lined up the swollen head with the entrance to her sex. He pushed forward slightly allowing her tight cunt lips to open up for his impressive cock. He was about half way in when he pulled out and then slowly eased back into her causing her to moan in pleasure. Matt would push in a little and then pull out a little slowly working his cock deeper and deeper into her vagina. Finally his entire cock was buried in her and Heather sighed feeling completely full almost afraid to move. This was still a new sensation for her to be this full as his cock touched certain areas within her for the first time.

Matt held himself inside her waiting for Heather to start fucking him. He looked down at her and smiled as he knew he had her and she would be his for the rest of the summer. Heather was ready to be fucked and she needed his big dick to slide in and out of her and rub her clit. She began to move and then Matt fucked her using long slow hard strokes. Heather locked her legs around Matt's ass and pulled him into her. He began to fuck her harder and faster and she felt another orgasm on its way. She was at the mercy of his impressive organ as it pounded her pussy.

If Matt hadn't just cum in her mouth he would not have been able to hold on as long. Heather was so hot and she squeezed him with her tight pussy. Matt fucked her through one orgasm after another before he filled her pussy with cum. His orgasm was as intense as hers as their bodies ground together and they moaned and groaned loudly. Heather felt the warm liquid fill her womb as Matt fired round after round into her. Heather could still taste his cum in her mouth and now he had cum in her pussy too.

Heather could feel his cock softening but even then it still filled her cunt. Matt slowly lifted himself off of her body and in so doing his thick cock slipped from her pussy. Heather felt the void in her cunt as his cock left her body and she gasped as the coolness of the air touched her vacant pussy. Matt rolled Heather over on her stomach and looked at Heather's ass and he could not resist running his hands over her shapely cheeks. Her ass was so round and so shapely that he felt his loins stir with desire. Matt got to his knees behind Heather and kneaded her gorgeous ass cheeks.

Heather thought back to earlier when Matt had kissed her buttocks and tongued her crack. She secretly hoped that he would do that again and she got her wish. He then began to kiss her ass cheeks and run his tongue lightly in the crack of her ass. Heather wiggled her ass feeling very wicked as he tongued and kissed her. No one had ever done that to her and the feeling was incredibly naughty. Heather felt that she was made love to for the first time in her life.

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bywalterio© 3 comments/ 175674 views/ 71 favorites

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