Anal Runs in the Family


"Would like a massage Mrs. Van? I give great massages," Matt whispered.

Heather just nodded her head accepting the offer. Matt then began to work on her shoulders and neck. Heather cooed as Matt massaged her body. He worked his way down from her neck and shoulders to her lower back. Then he purposely bypassed her buttocks and moved to her calves. He massaged her calves and then moved to her thighs where he spent a long time. Heather could feel her body heating up again even though she didn't think that she was capable of another orgasm. Matt then moved his hands to Heather's shapely fleshy ass and molded the soft globes in his hands.

Matt liked the look and feel of Heather's ass and he thought about fucking her in her ass but then decided against it. He would have plenty of time to take her ass. He was sure that she had never been butt fucked and he didn't want to scare her away on their first day together. As Matt looked at Heather's ass he was tempted to plow it with his big dick. Instead Matt lifted Heather to her knees and slipped his cock back in her pussy and fucked her doggy style. Heather turned her head to the side and groaned when the big cock filled her again. Matt fucked her in the doggy style position and he caressed Heather's curvy ass. He sensed that Heather was getting hot again so he pulled out of her pussy and turned her over on her back. Then he positioned himself between her legs and fed his cock into her pussy again. It had been so long until today since Heather had a real cock in her and Matt filled her completely. Every fiber of her vagina tingled as the big dick made its way in.

"Oh yes, oh it feels so good, oh, oh, fuck me, yes fuck", Heather cried as she was close to another orgasm.

Heather couldn't remember the last time she ever orgasmed three times in one day or if she ever did. Matt slid in and out of her pussy slowly allowing Heather to adjust once more to his size and he continued to go deeper with each thrust until he was buried balls deep in her pussy. He was surprised and pleased when he heard the sophisticated Heather use the fuck word.

"Oh my I have never been so full, fuck me, make me cum, make it last forever", Heather cried out not caring that she was fucking her daughter's boyfriend.

Matt pounded her pussy making sure that his cock was in constant contact with her clit. Heather had multiple orgasms as he fucked her. Heather had pretty firm tits with rock hard nipples that extended a ½ inch. Matt twirled the nipples in his fingers and then leaned over taking one then the other in his mouth. Matt couldn't believe how things had worked out and how well it was going with Judy's mother naked and he savored every moment. Heather was one hot lady.

Heather went wild telling him. "Oh yes, suck my tits, suck my nipples, fuck me good!"

Matt could feel his balls start to tighten and he knew it wouldn't be long before he filled her pussy with his cum for a second time. Heather stiffened and then had another violent orgasm. She thought to herself that Matt was incredibly experienced for his age as he fucked her and sucked her tits.

Heather yelled, "Hold me, please hold me, I'm cummmming!"

Matt reached around behind her back and pulled Heather toward him as she shook and trembled throughout her intense orgasm. As she was cumming so did Matt and he fired another barrage of cum into her pussy. As she started to recover Matt laid her back down on the bed and slowly fucked her as his cock softened. Matt's cock was swimming in her cunt; there was so much cum in there mingling with her own juices.

Heather ran her hands over Matt's muscular arms; pecs and washboard abs. Then Heather looked down at Matt's soft cock and took it in her hand for the first time. Even soft it was bigger than her husband's cock. She felt his cock harden in her hand and at first she couldn't believe that he was ready to go again. Even in her exhaustion, she held her arms open to him welcoming him between her legs again. Matt crawled between her legs and slipped his hard cock back in her pussy. Matt never wanted this to end and he wanted to fuck Judy's mother all day. Heather knew she had crossed the line but right now it felt so good to have a real cock in her. Matt fucked her as long as he could before Heather pleaded with him to let her rest.

However Matt ignored her pleas and he began to pick up the pace. Soon he was pounding her pussy and fucking her into submission. Heather moaned and groaned as Matt relentlessly fucked her. Matt just kept at her with his hard-on until she screamed and pleaded with him to stop. Finally Matt came for a fourth time that day and collapsed on top of Heather. After a few minutes Matt pushed his body up and he eased his cock out of Heather's well fucked pussy. He was thrilled with the encounter with Judy's mother and he was proud about how many times she had orgasmed at his hands. Matt looked forward to many more sessions with Heather.

Heather rolled over and looked at the clock and saw that they had been having sex for almost five hours. They had fucked right through the lunch hour and it was almost 2:00 PM. Heather remained in bed while the self assured Matt took a shower in her bathroom. Matt came out of the bathroom naked and calmly went about getting dressed. Once he was dressed he came over to the bed and kissed Heather.

"Mrs. Van you were wonderful and I look forward to seeing a lot over the summer," Matt said confidently and then he left Heather naked in her own bed.

Heather remained in bed for another 30 minutes before she summoned up enough energy to make it to her bathroom. She ran a hot bath for herself and while the tub was filling up she straightened up her bedroom. Then she eased her achy body into the hot bath, closed her eyes and tilted her head back on the tub. As she soaked in the tub she thought about what had happened. She never had better sex in her life but now she was worried about how far things might go with Matt. She would have to be very discreet and not even mention his name to anyone. Heather didn't have anything planned for Friday so she had no excuse to use to keep Matt away, not that she really wanted to keep him away. Heather soaked in the tub for an hour and then dried off and got dressed before Judy got home from the beach.


For the next two weeks Matt had more sex than he had ever expected with Judy and her mother. He loved drilling Judy's hot ass and he loved making Mrs. Van cum until she nearly passed out. Matt was enthralled with Judy's magnificent ass and he fucked it often. He really didn't need to fuck Mrs. Van in the ass to satisfy his anal cravings but he decided to do so anyway. He was convinced that she had never been butt fucked and he had no idea that she often used her vibrator on her nether hole.

After her husband went to work and Judy left for the beach with her girlfriends, Heather put on her robe and went downstairs to make coffee. She was surprised when Matt entered the house that morning. The front door was unlocked and Matt was walked in as he had become accustomed to do doing. Matt took a seat at the kitchen table as he greeted her that morning.

"Good morning Mrs. Van, how are you today?" Matt asked assuredly.

"I'm fine Matt. I just didn't expect to see you so early," Heather replied nervously as she poured Matt's coffee.

Heather was nervous since she was naked under her robe that morning. Matt sat at the kitchen table sipping his coffee as Heather worked at the sink facing away from him. Heather was extremely confused over the strange relationship. She struggled internally with her emotions. She had agreed to let her own daughter's boyfriend fuck her and she enjoyed it as it was the best sex she had had in years.

Matt then got up from his chair and walked over to her as she was reflecting on the day before. Heather felt his presence behind her and she trembled. She wondered why she suddenly felt so insecure in his presence. Matt put his arms around Judy's mother's waist, pulled her back toward him and nuzzled her neck. Matt moved his hands up to her breasts and began to massage them through her bathrobe.

"You have very nice tits, Mrs. C," he told her once again using the word tits again instead of breasts.

Matt moved his hips forward and Heather felt his enormous cock pressing into her bottom through the robe. Matt then dropped to his knees behind her, lifted her robe up and trailed kisses up and down each leg and on her ass cheeks. Heather was trembling with desire and she wondered where Matt had learned these things in so short a time. Matt turned her around toward him and began to tongue her sopping wet pussy. Heather came violently humping his face and covering it with her pussy juice. Heather was too weak to stand any longer so she allowed Matt to lower her to the kitchen floor. Matt removed her bathrobe and spread it out so that Heather could lay on it.

Matt then stood up and removed his clothes. His stiff hard cock looked menacing from where Heather was on the floor. Matt knelt down and maneuvered between Heather's legs. Then he eased his cock into her sopping wet pussy and Heather grunted as the big dick filled her womb. Matt began to fuck her slowly and then he picked up the pace. Heather couldn't believe how sexually charged her body was as she humped up at the virile young man. She wondered how they must look on the kitchen floor. What if her husband or Judy had returned because they forgot something?

Heather had several orgasms before Matt's body stiffened and he flooded her pussy. Heather could feel his cum shoot into her as jet after jet seemed to splash against her womb. Her pussy was drenched with their combined love juices and Heather's clit ached from her intense orgasms. Matt pulled out and knelt above her and Heather saw that his cock was still hard and ready for more action. Heather rolled over on her stomach in an effort to protect her pussy from any more attention.

Matt looked at Heather's ass and he could not resist running his hands over her shapely cheeks. Her ass was so amazing that he felt his loins stir with a renewed desire. Matt had no knowledge of whether Judy's mother had ever been butt fucked but he assumed that she never had. Matt got to his knees behind Heather and kneaded her gorgeous ass cheeks. He then began to kiss her cheeks and run his tongue lightly in the crack of her ass. Heather wiggled her ass feeling very wicked as Matt tongued and kissed her. Matt lifted her by her hips so that her ass was perched in the air. Heather's head was still on the floor and she turned it to one side on the bathrobe and let out a gasp as Matt's tongue licked close to her asshole. Until Matt no one had ever licked her asshole and again she was surprised with his sexual maturity. Matt ran his tongue from her pussy to her ass causing her to tingle in anticipation of what might be next.

Matt spread her ass cheeks with his hands and dipped his tongue into the crack locating her nether hole. His tongue slowly circled her anus and she flinched at the contact. He then pushed his tongue as far as he could into her asshole and he found himself wanting to fuck her up the ass. He continued to ass fuck Heather with his tongue until she was at his mercy. Heather's desire grew as Matt worked her ass to the point that she suddenly felt that she wanted something more in her ass. And she thought of her vibrator.

Matt removed his tongue from her ass and ran his hard cock between her ass cheeks as he spoke to her, "I want to fuck you in the ass Heather. Do you want me to fuck your hot ass? I can see that your ass is asking to be fucked."

"Matt no, don't you dare try," Heather yelled in a panic.

"Stay right there," Matt told her as he retrieved a bottle of vegetable oil from the pantry.

Then he knelt behind her and once again shoved his big dick into her pussy. Heather was relieved when he put his cock in her pussy. She didn't mind being fucked dog style and it gave her clit a rest. He started to play with her ass again and squirted the oil in the crack of her ass. He massaged the oil into her asshole and began to finger her ass. The oil made Heather very slick and Matt's finger slid easily in and out of her anus. It was Heather's first anal penetration other than her vibrator. Although it seemed wicked, Heather found that she liked the finger in her ass while his cock was in her pussy. Then he pulled his cock out of her pussy and let the head rest against her anus.

"You want it in your ass Heather?" She heard Matt say as she felt his cock press against her virgin ass hole, "I want to fuck your hot ass."

"No please no!" Heather cried shaking her head from side to side with her face pressing against the robe covered floor. "I've never done that, you're too big. You'll ruin me."

"Don't be silly I'm not going to ruin you. You just need to be stretched a little. If your petite daughter can take me, you certainly can," Matt said in a confident tone.

Matt had gone this far and now he was determined to take Heather's ass. It was the last frontier for her and besides he loved fucking girls in the ass ever since that time at the pool with Marilyn. Matt spread plenty of oil on his cock making it very slick. Then with one steady motion he plunged his cock into Heather's asshole. He seemed gigantic, long and wide and Heather screamed as he began to work his way into her poor tight ass. She could actually feel her stomach cramping around him as he stirred her insides and it burned when she clenched her ass muscles convulsing around his thickness. Shaking and sobbing with painful ecstasy, Heather fell forward onto her robe with Matt's hands keeping her ass high in the air for him to plunder.

Heather screamed into her robe as it felt like a hot thick poker had just been rammed into her ass. Tears filled her eyes as her violated asshole spread to accommodate Matt's thick cock. She tried to get away but Matt was too strong and held her in place. Heather cried out loud only to have the sound muffled by the robe as his complete length filled her. Heather felt him flex his cock deep within her bowels as the searing pain continued. Matt reached one hand under her again and teased a nipple. Then he moved his other hand down and rubbed softly against her clit. Heather's body responded to his stimulus and her stomach convulsed with mixed signals.

The intrusion in her ass didn't feel quite as bad now as Matt's fingers continued to tease her clit. Heather felt him move inside her ass now and she tried to relax her ass muscles. Heather's body was working back and forth on his cock now and she was amazed at the feeling of the cock in her ass. Heather's clit was buzzing and the fullness in her ass just seemed to excite her pussy even more. Matt started hammering into her ass now. His fingers were still busy on her clit but now he had two fingers drilling in her pussy as the others fluttered around her clit. Heather's whole body was aflame as she could feel his fingers pressing against the thin membrane separating her ass from her pussy. She could feel his hard cock sliding in her and the pressure of his fingers on his cock through her thin membrane. Heather didn't need Matt to force her on his cock anymore, nor did she need him holding onto her tightly. Her entire body was fucking back at him of its own accord. Heather could feel an enormous orgasm building within her and her pussy was swollen to new proportions.

"Oh God," Heather thought to herself, "I'm going to cum again, Oh God!"

Matt continued plowing into Heather. The hot depths of her ass were so tight around his cock she knew that he was going to cum hard too. He worked his fingers faster inside her as he rammed his cock hard into her ass. Heather started biting the robe like a mad woman as his groin made hard contact with her ass. Heather felt her pussy spasm suddenly and then her whole body went rigid. She felt his cock swell in her rectum and then hot spurts of liquid lava hit her deep in her bowels, giving her a cum enema. Heather screamed into robe. Both of them shuddered hard as every muscle tensed and then relaxed. Heather felt a hot explosion as her body was overcome with the most violent orgasm she had ever had. She could still feel Matt's cock throbbing and spurting deep within her. Heather felt Matt's cock shrink in her ass and then slowly back out making an audible popping sound. Heather's ass was still high in the air and her thighs were aching. Matt lovingly caressed her shapely ass cheeks.

He was proud of himself and his conquest. He had never expected to fuck Judy's mother in the ass so soon but he couldn't stop once he got started. He was pleased that he was her first ass fuck. Matt backed off as Heather lay face down on the floor and she refused to look at him. Heather was humiliated by the act and she was embarrassed by her behavior. She was still stunned that she had been fucked in the ass and by someone young enough to be her son. Heather then felt herself lifted off the floor and then she was carried upstairs to her bedroom. Matt left his clothes and her robe on the kitchen floor as he carried Heather in both arms. Heather had both hands around Matt's neck and she had her head buried in his neck. Heather was ashamed of what just happened and she couldn't even look Matt in the eye.

Matt walked into the bedroom and deposited Heather on the bed. Then he went into the bathroom and turned on the bathtub faucets. Matt located some oily beads and added a few of them to the water. Matt waited until the water temperature was just right and then he went back into the bedroom to get Heather. Reluctantly Heather allowed herself to be led into the bathroom to bathe with Matt. Heather got into the tub and Matt got in with her and got behind her. Matt guided Heather's body back so that it rested against his and he wrapped his arms around her.

"Now let's relax and enjoy the bath for awhile," Matt said as he spoke the first words since taking Heather's anal cherry.

Heather was still speechless as her mind was cluttered with thoughts. She had never expected things to turn out like they did. Heather felt dominated and submissive in the hands of the young stud. On one hand she was having great sex and on the other she was scared of the way her body betrayed her. Heather never knew that she was capable of such behavior.

Matt reached up and caressed and fondled Heather's breasts and toyed with her erect nipples. Her tits and nipples felt particularly good in the oily water. Heather then felt Matt's cock harden and press against her buttocks. She knew that she was in for another round of sex but she had no idea what he had in mind this time. They soaked in the tub for almost and hour with Matt caressing Heather's body before they finally got out and dried off. Matt dried off Heather's body and then she dried Matt.

Matt's cock stayed hard the entire time that Heather dried him off with a fluffy towel. Heather let her hand brush against the erect cock several times and she enjoyed watching it twitch each time. All of a sudden the cock did not look so menacing although it was still hard to believe that something that size had been in her ass. Heather had a strange desire to take the cock in her mouth again and she dropped to her knees in front of Matt.

Matt was pleased when Heather wrapped her lips around his cock without any urging from him. Heather sucked the cock deep into her mouth and tested her gag line seeing how much she could take in her mouth. She then fondled Matt's balls and she was pleased when he groaned with pleasure. Heather closed her eyes with her lips snugly wrapped around his shaft as she bobbed back and forth. She was incredibly turned on and her pussy was soaked again.

Matt brought excitement into Heather's life with his 8+" cock and she was now addicted to it. Heather was so enamored with his cock that she discovered she loved to suck on it. Heather was happy to please Matt again and to make him cum. Heather wanted this to be Matt's best blow job and she put all her efforts into it and it did not take her long to bring Matt to the edge.

Report Story

bywalterio© 6 comments/ 289706 views/ 185 favorites

Share the love

Report a Bug

4 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: