tagAnalAnal Runs in the Family

Anal Runs in the Family



Heather Vanvanderen was spying on her 18 year old daughter Judy and Judy's 20 year old boyfriend Matt. It was the fourth time that Heather was spying on them ever since the first time she mistakenly saw them having sex. She had decided not to confront either her daughter or Matt as she found that she liked watching them as it turned her on. They were both naked with Matt on his back in Judy's bed. Judy was by his side kneeling over Matt sucking his impressive cock. Matt was caressing Judy's superfine ass and tickling her anus with the tip of his finger.

Matt wasn't a freak but he was well endowed and he had the biggest cock that Heather had ever seen. Heather watched as Matt took some lube and applied it to Judy's nether hole. Soon he had one and then two fingers sliding in and out of Judy's asshole. Upon Matt's signal, Judy released his cock and got on all fours as Matt knelt behind her. This was Heather's favorite part as she watched Matt ease his big dick into her daughter's shapely ass.

Heather had never had anal sex but ever since she saw her daughter take it in the ass, she was curious. Heather had a vibrator that she used to satisfy her needs these days and she had started to tease her ass with it. Heather had progressed so that with lubricant she could insert the vibrator into her asshole. She was thrilled with the tingling sensation and understood why Judy liked a cock in her ass. Heather continued watching Judy and Matt as they fucked like crazy. Judy was begging Matt to drill her ass.

Heather noticed the strain on Matt's face and she knew that he was close to cumming. Matt then pulled out of Judy and aimed his cock at her asshole and buttocks. He fired streams of semen onto Judy's body and then pushed his cock back in her ass. Matt would gather up his spunk with the head of his cock and push it into Judy's hole. Judy wiggled her ass in delight and cooed softly.

"Oh, I love that," she said softly and then she rolled to her back spread her legs and said urgently, "Here eat my pussy, I need to get off now."

Matt lowered his face between Judy's legs and lifted her thighs onto his shoulders. He kissed her inner thighs teasing her briefly before his mouth found her juicy pussy. Heather moved away from her vantage point as she knew what would happen after that. Matt would eat Judy until she came and then he would drill her pussy with his vibrant cock until the both came again. Heather knew they would be at it for hours since she wasn't expected home until later. She would have time to satisfy herself with her dildo before she left the house again.


Matt's best friend was Joe Murphy. The Murphy family lived next door to the Vanvanderen family. Joe was the oldest of four boys and he and Matt had graduated from the same high school. They played ball together in school and had become very close. Joe and Matt attended different colleges but they always hung out together over the summer. Judy was a sophomore when Matt was a senior and he didn't pay much attention to her or any underclass girls. He was dating a girl named Gail and they were inseparable in high school. Matt and Gail still dated occasionally when they were home from college.

One Friday afternoon Matt and Joe were playing basketball at Joe's house. The two of them were pictures of fitness having shed their tee shirts. Both boys were ripped and their bodies glistened with perspiration. Matt was 6'1" and weighed 190 pounds. Joe was 6"3" and weighed almost 195. They had both played varsity basketball in high school and they loved to compete one on one with each other.

Mrs. Murphy walked out on their deck over looking the driveway where the court was set up and called out. "Matt would you like to stay for dinner tonight? I made a big meal and we have plenty."

"That would be great Mrs. Murph, thanks! Matt accepted.

Matt always called her Mrs. Murph just as he shortened other parent's last names when he addressed them. The guys kept on playing until Mrs. Murphy told them it was time to clean up for dinner. Matt had showered at Joe's house before and he had even stayed over several times. The two of them showered and dressed for dinner. After dinner they were shooting pool with Joe's younger brothers in the game room when Mrs. Murphy came in.

"Mrs. Vanvanderen called and Judy is having a party. Judy would like you two to come over," she told Matt and Joe.

"I don't think so mom," Joe replied.

As it turned out the Vanvanderen's were insistent as there were more girls then boys at the party. Mrs. Murphy pleaded with her son and Matt to stop over even for just a short while. "Heather is relentless with her daughter's request."

Matt looked at Joe and shrugged his shoulders. "I guess we could for a while," Joe agreed.

The two guys then headed over to the neighbor's house. "Have you seen Judy since you've been home?" Joe asked.

"No I haven't. I never paid much attention to her in high school," Matt replied.

"She is 18 now and I expect everyone at the party is too. She's cute, petite but cute. She has no tits but a killer ass," Joe shared.

"Okay but we're not going there to get laid or even hit on these girls are we?"

"No really but we'll see what happens," Joe laughed and then added, "I'd really rather fuck Judy's mom but that's not going to happen."

"Her mom, why do you think she is hot?"

"Oh yeah, she has a great body. It's obvious where Judy gets her hot ass from. I watch Mrs. Van at her pool sometimes. She wear's the skimpiest bikinis and it gives me a hard-on."

"Well try to behave tonight," Matt joked.

"I will, it's just a fantasy of mine," Joe admitted.

They got to the house and rang the door bell. Judy's dad let them in and showed them downstairs. "Thanks, Mr. Van," they said.

Both Joe and Matt had always called the parents Mr. and Mrs. Van. They entered the finished basement where about 20 recent high school graduates gathered. There eight couples and four single girls and Judy was one of them. Her date was a no show and she was livid until Matt showed up. Judy had always had a crush on Matt but she never told anyone. She would watch Matt and Joe play basketball at the Murphy's and she would fantasize about him seducing her. Now he was in her house and she would make her intentions known.

Most everyone at the party remembered Joe and Matt so introductions were not necessary. Judy moved right to Matt's side and offered him a drink. Matt accepted and watched Judy as she got his drink. Joe was right she had an incredible ass. Judy was just 5'4" tall and she couldn't have weighed 100 pounds. She was flat chested as Joe had said but what an ass. Judy wore her brown hair short in a pixie style and she looked as cute as a button. She was wearing plaid slacks and it looked like her bottom stuck out a good 10-12 inches from her waist and thighs. Judy returned with the drink and they chatted idly.

Matt looked over at Joe and he was engaged in conversation with the other three girls who were without dates. Joe was telling jokes and had them laughing. Matt noticed that on several occasions Joe fondled two of the girls and they seemed receptive to his advances. The three girls were not very attractive but that didn't seem to bother Joe and they were pleased with the attention he gave them. The music was playing and the other couples were dancing to a slow song when Judy asked Matt to dance with her. He put his drink down and Judy melted into his arms. She wrapped both hands around his waist and snuggled in close.

Matt was surprised by Judy's actions but he went along with it and wrapped his arms around her petite body. They stayed locked together for three straight slow songs and by the end of the second on Matt had a raging hard-on. During the third song Judy moved her thigh so that it pressed firmly against Matt's erection. She tucked her head in against his neck and his face nuzzled her hair. When the fourth slow song started Judy lifted her head and whispered to Matt.

"I can feel you. I like that I can feel you."

"You are very cute Judy," Matt told her as he let his hands slide down over her buttocks.

Matt cupped the firm shapely bottom and pulled Judy against his erection. She lofted her head to be kissed and Matt obliged her. She surprised him when her tongue darted into his mouth but Matt matched her assertiveness. The French kissed as they moved to the music. It couldn't be called dancing as they just rubbed their bodies together as Matt fondled her incredible ass.

They broke their kiss and Matt looked around at the other teenage couples. They were all locked in tight embraces kissing. Matt was convinced that it the parents were not home that the party could have turned into an orgy. Joe was still missing as were the three girls he was talking with earlier. Matt smiled to himself as he suspected that Joe was probably outside fucking all three of them.

Judy snuggled in tighter if that was possible. Matt whispered to her, "Judy, we can't start something that we can't finish. Your parents are right upstairs."

"Come with me," Judy told him in a soft voice and took his hand.

Matt noticed the other couples were so involved that they never saw him and Judy leave the room. Judy led Matt into a storage area and she turned on a dim light. She lifted her face to be kissed and Matt kissed her. She ran his hand over the bulge in his pants and fumbled for his zipper. Judy was nervous but she managed to free his stiff cock and she stroked it in her small hand. Matt felt her tremble in his arms.

"You're big," she whispered.

Matt unfastened Judy slacks and pulled then down to her knees. He felt her panty covered pussy and the panties were damp. Judy moaned and shivered as he stroked her vulva but she continued to play with his cock. Matt slipped his hands into the back of her panties and cupped her lovely ass cheeks. Her skin was so smooth and so firm, her ass was magnificent. Matt lowered her panties to her knees and then turned her around. Judy was reluctant to let go of his cock but she complied.

Matt looked at her ass and he had never seen one more shapely or more beautiful. He dropped to his knees and planted kisses on her buttocks. Judy trembled again and goose bumps appeared on her skin. Matt kissed, tongued and fondled her fantastic bottom and Judy flinched when his tongue darted into her crack. He continued to make love to her ass until she told him that she thought she was going to cum. Matt turned her around and pulled her slacks and panties down to her ankles so that he could get to her pussy.

Matt lifted Judy onto a table and ducked his head between her legs. He quickly located her pussy with his mouth and fingers. Matt found her g-spot quickly and fastened his mouth on her clit. Judy moaned in pleasure as she grabbed his head with both hands. Within minutes she was moaning and squirming as her orgasm approached. Judy covered her mouth with her forearm to muffle her screams of ecstasy and her body bucked and jerked as she climaxed. Matt stayed with her and drank down every drop of her sweet nectar.

Matt moved out form between her legs and looked at the petite beauty on the table. Her slacks and panties were around her ankles and her pussy glistened with moisture. Matt moved toward her and she took his cock in her hand and stroked it again. Matt sensed that he would only get a hand job but he was fine with that given the situation. Judy stroked him and jerked him off until he was spurting gobs of semen onto the storage room floor.

The two of them composed themselves, dressed and returned to the party. A couple of others gave them a weary eye but no one said anything. Matt got something to drink and then Judy's mom came downstairs to check on everyone. Matt checked her out remembering what Joe had said and sure enough she had a hot body and a killer ass. Judy was talking with her mom so Matt decided to look for Joe. He went outside to the pool area and looked around.

Matt spotted Joe over by the supply shed with the three girls. All four of them were naked from the waist down. Joe was fucking one girl from behind as the other two stood close by. Matt's suspicions were correct that Joe would probably fuck all three of them. Matt returned to the party which had started to break up. Judy corralled him for another slow dance and she whispered.

"I hope we can see each other again."

"What about a movie tomorrow night?"

"That would be wonderful."

"I'll pick you up about six and we'll go to the early show."

Judy nodded and then laid her head against his chest. As they were dancing Joe and the three girls returned and they were all smiles. Matt told Judy that he should be going and that he would see her tomorrow. Judy nodded and kissed him goodnight. Matt and Joe left the party.

As the walked back to Joe's house Joe asked, "So how did it go with you and Judy?"

"Okay, she's cute and she's nice," Matt replied.

"Did you get any?"

"No, we had a nice time that was it. What about you?"

"You should have hung with me. I fucked those three horny babes," Joe bragged.

That was the difference between Joe and Matt. Joe always bragged about his sexual exploits and Matt kept his mouth shut. When they got back to Joe's house, Matt got in his car and drove home. On the drive home he couldn't get Judy's magnificent ass out of his mind. Even in bed that night he kept thinking about Judy's ass and he recalled his first anal experience which had led to his obsession with the female bottom.


It was the summer after graduation and Joe and Matt were hanging out at the community pool on day. It was overcast with a threat of rain so the pool was not very crowded. Usually the basketball court was packed with teams of five waiting to challenge the winners. That day there were only enough players to conduct three on three half court games. Joe and Matt would play for awhile and then go for a swim. There was only one girl there that day who they knew. Marilyn had graduated with them but she did not run in their circles. They both knew that she put out.

Marilyn openly flirted with Joe and Matt and let them know with her body language that she was theirs for the taking. Marilyn was not a pretty girl but she was not offensive either. She hated her hair which was coarse and straw like, so she kept it pulled back. Marilyn was stacked though and she filled out her one piece bathing suit which displayed all her curves. At 5'6" and 115 pounds Marilyn cut a hell of a figure. She had 36 B breasts, a narrow waist and an ass that one could crack an egg on. Her legs were shapely and finished off her curvy figure.

The three 18 year olds were sitting on a picnic bench sipping sodas and chatting when it began to rain. The few people there headed for their cars. Marilyn, Joe and Matt headed for shelter and stood under an overhang. The rain let up briefly and Joe suggested that they move to the back of the building. There was a larger overhang there and it was more private. Just as they got there the sky opened up again and it poured. The rain pelted down on the roof and it was the only sound they could hear. Matt looked at Marilyn's shapely bottom and patted her on the ass. Marilyn giggled and wiggled her ass in response. Matt was turned on by her reaction and patted her ass again only this time he left his hand on her curvy buttock. Marilyn just turned and smiled at Matt.

"So you like your ass played with do you," Matt said as he squeezed her ass.

"I love my ass played with, it is so sensitive," Marilyn replied in a sultry voice.

Joe walked up behind her and grabbed her tits, "How about your tits are they sensitive too?"

"Oh yes they are very sensitive," Marilyn answered as she held Joe's hands firmly against her breasts.

By this time both boys were sporting erections and Marilyn passed her hands over the boy's crotches. "My, what have we here," she teased.

Joe slid the bathing suit straps off Marilyn's shoulders and pulled the top down to her waist. Marilyn's firm tits stood straight out from her body and Joe quickly covered them with his hands.

"Oh man look at these tits!" Joe exclaimed.

Matt then pulled her bathing suit down her legs to her knees. "Look at this ass," Matt called out.

"Don't take our bathing suits all the way off in case somebody comes back here," Marilyn told them.

The two boys were beaming with excitement at the unplanned turn of events. Marilyn smiled at both of them and then she dropped to her knees and peeled the boy's swim trunks down to their knees. Their erect cocks bobbed in front of her face. Marilyn was pleased to see that the cocks were bigger than average.

Marilyn took both cocks in her hands and took turns licking the cock heads as she stroked them both. Both Matt and Joe were ready to blow their loads so Marilyn sucked off Joe first until he came in her mouth and then she sucked Matt's cock until he too filled her mouth with cum. Marilyn kept sucking them and playing with them and managed to keep the boys hard. Then she lay on her back and told them to fuck her. Joe mounted her first and fucked her until he came again. Marilyn had orgasmed several times before Joe came. Joe pulled out of her and Marilyn's pussy was quickly filled with Matt's cock. Matt fucked her until he came again and Marilyn also orgasmed several times with him in her. The three of them lay on the ground and the two boys were enamored with Marilyn's body. They kept caressing, sucking her tits and playing with her ass as if they could not get enough of her voluptuous body.

"When you guys get hard again I want you to fuck me in my ass. Would you like to do that? Have you ever fucked a girl in the ass?" Marilyn challenged.

Neither Joe nor Matt had ever butt fucked a girl but Joe was not interested in anal. Matt couldn't believe his ears when Marilyn asked them to fuck her ass. This was a girl who was experienced beyond her years. Marilyn told Matt to get the suntan lotion and to grease her asshole with it. She told him to put it on his cock and then to use saliva to make his cock really slippery. Marilyn got on all fours and cradled her head on her arms with her face turned to one side. Then Matt fucked Marilyn's ass and Joe shoved his cock back in her mouth. They were overcome with desire and tried to prolong their ejaculations as long as possible. It was the most fantastic sensation of his young life when Matt shot his spunk into her beautiful ass.

The three of them continued to go to the pool and hang out for the rest of the summer. They had sex together as often as they could. Marilyn loved foreplay and one of her favorite things to do was to stand with her bathing suit around her knees with the boys on either side of her. The boy's swimsuits were around their knees as they played with her tits, ass and pussy and she stroked their erect cocks. Marilyn loved to have her holes finger fucked and the boys often did that while she stroked their cocks. One day Marilyn decided that she wanted both of them to fuck her at the same time so for the rest of the afternoon Joe and Matt double fucked her. Joe lay on his back as Marilyn sat on his cock and Matt guided his cock into Marilyn's ass. The three of them fucked like this four times with them cumming in Marilyn's ass and pussy. Marilyn was full of cum and she loved the feeling of its presence in her ass and pussy. The boys were overcome with lust as they double fucked her repeatedly.

Matt and Joe never told anyone about Marilyn and they kept on dating their high school girlfriends. It was Marilyn's incredible ass and her passion for anal sex that converted Matt. He became enamored with the female bottom and loved fucking it. There was nothing more pleasurable for Matt then to watch his big cock slide in and out of a shapely ass. Matt fell asleep that night and dreamt that he was fucking Judy's incredible ass.

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bywalterio© 6 comments/ 290000 views/ 185 favorites

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