The MILF and Her DILF Read online

  Jason was ecstatic, so daddy took a younger model? Annie my dear, you just showed me the lever I need to capture you.

  “I don’t know, he is kind of cute, but I am already fielding a bunch of advances from some of the guys I met at registration. Maybe if he shows some interest in me I might try him out, but I still think he would be better for you.”

  “We are not having this discussion young lady, I am your mother and it is inappropriate,” replied Annie, as she stood up, then she said, “I am going to take a nice hot bath.”

  Jason enjoyed the show Annie provided that night, especially when she started masturbating in the tub. He had to wonder if what Beth had said to Annie had prompted the bathing beauty to satisfy herself like she was. But at least he learned that she had a sex drive, given how she shuddered in the tub when she came. After she recovered and finished her bath, she went to bed, but little Beth soon took her place for Jason.

  She also took a bath and followed her mother’s lead, also playing with her pussy in the tub. Jason had to beat his meat while watching Beth, still aroused from Annie’s amorous adventure. They were like mirror images of each other, both with large breasts and an apparently high sex-drive, the only difference being their disparity in age. He could picture himself with either of them, but when he imagined them both catering to his desires in unison, he popped his cork, splattering is spunk all over the place.

  When he had showered and climbed into his bed that night, having watched both of them head for their beds first, he had no idea that his pursuit of Annie would begin just the next day. But he slept well, knowing that his voyeurism was only the first step in his quest. Soon, he knew, he would feel what he could only see for now. He had decided that Annie would be his first conquest and that Beth could wait a little while, at least until Annie was under his control.

  Chapter 2: Making Mama Squirm

  When Jason awoke the next morning he saw that their car was gone, and after checking his spy cams, he saw that it was Beth who had left. Annie was in the kitchen, loading a basket with eggs, bacon, and other breakfast goodies. He guessed that she was about to bring him his first meal, so he quickly got dressed and headed downstairs. A few minutes after he arrived in the kitchen he heard a knock on his door and he went to answer it.

  Annie stood there with the basket hanging from her arm and a bright smile on her face. “I hope I am not intruding, but I owe you a meal and thought breakfast would be a nice way to start.”

  “Breakfast sounds great, where is Beth?” he asked.

  “She has a full day of orientation today, she won’t be back until dinner time.” replied Annie. She was wearing her shorts and a large t-shirt that obscured how large her breasts actually were. Her legs were bare and clean-shaven, and she was only wearing a pair of flip-flops on her feet.

  Jason stepped back and said, “Come on in.”

  She smiled again as she walked past him, heading for the kitchen. He followed, enjoying the way her ass wiggled when she walked. He took a seat as she emptied her basket, found some pans, and started to cook his eggs and bacon. They engaged in some idle chitchat, with Jason making sure to drink in her beauty as she cooked for him.

  Once the food was done and she sat with him to eat together, he decided it was time to go fishing. He said, “Forgive me if I am intruding, but why did you and your husband divorce?”

  She paused for moment, looking like she was not sure if she should respond. But she replied, “It is rather embarrassing actually,” her face blushing as she spoke, “but he had an affair with his secretary and now she is pregnant.”

  “What a fool,” replied Jason, actually believing it. “Forgive my intrusion, but I think that a man who had such a beautiful woman in his life is just an idiot for fooling around like that. Are they together now?”

  Annie’s blush deepened as she replied, “Thanks for the compliment, but it is partly my fault. Our relationship had cooled and I did not realize it until it was too late. And to answer your other question, yes he is with the bitch…oh…excuse me!”

  “No need, you have every right to be upset about that, it was his responsibility to keep the spark going in your relationship too. You can’t be the only one who made a mistake, he is accountable too.”

  “Yes but he has a new wife that is barely a few years older than my daughter, you can imagine how much that hurts,” she replied, her voice a bit shaky as she spoke.

  Jason put his hand over hers, feeling her flinch at first, but then she quickly relaxed. He said, “I still think he was a fool, you are a very attractive woman Annie.”

  “Thank you Jason, but it will take some time for me to believe that again.”

  “Time heals all wounds,” Jason said, and then he withdrew his hands and began to eat. She followed suit, looking somewhat dejected that Jason brought up her past, but she was in a frame of mind where he knew he could make his first move. Once they finished eating, she stood up and took the plates to the sink. As she started to wash them Jason stood up and walked up behind her.

  He stood very close to her and said, “Can I help?”

  She could feel him standing behind her and she remembered what Beth had said the night before. His simple question had many answers for the depressed and self-esteem starved woman, but she was afraid to do anything other than wash the dishes. So she said, “I can handle a couple of breakfast dishes, but you are a dear for asking.”

  But Jason remained just behind her, looking over her shoulder as she washed the breakfast dishes. Then, once the plates were clean and in the drain board, he said, “I wasn’t kidding when I said you were an attractive woman, in fact you are quite beautiful.”

  She turned to face him, but he did not step back, so they remained very close to each other with his face just inches from hers. She whispered, “Thank you Jason, you really are very kind.”

  “Kindness has nothing to do with the facts Annie, you are a very hot lady. The way you look I still find it hard to believe you have a full grown daughter.”

  Her blush returned and her breathing became faster, as she stared up into his blue eyes. He could see the need inside them, she wanted him to remind her that she was more than just Beth’s mother; she wanted him to show her she was still a woman. But all she managed to say was, ”Stop it Jason, I am old enough to be your mother.”

  “So?” he said, just before crushing his lips against hers and snaking his tongue into her mouth. She hesitated for a few moments, but then the dam burst and she was kissing back, very passionately. While their tongues wrestled in their mouths, he lifted her up to sit on the edge of the sink. Once she was seated, she wrapped her legs around his torso and her eager tongue went into overdrive.

  Jason gripped her firm buttocks, squeezing them hard as he kissed her deeply. In response she started to rub her crotch against his jeans and he could feel the heat emanating from between her legs. After he was sure she was as hot and ready as he needed, he broke off the kiss and said, “See? You are a hot and delicious lady.”

  She replied, her voice barely a whisper, “This is wrong we should stop,” but she did not seem convinced of it.

  He reached up with his right hand and took a fistful of her hair, pulling her head backward, before saying, “You are a free woman and if your husband can enjoy a younger woman, why can’t you do the same with a younger man?”

  “But…” she said, but nothing else came out once his lips had crushed into hers again. He broke away after a moment and said, “Ask me to take you to my room and show you how good it can feel to be with someone new, someone who wants to pleasure you Annie.”

  “Yesss, please take me Jason, I need to feel a man want me again,” she replied, her voice absolutely breathless, as she forced the words out from between her luscious lips.

  He simply lifted her up, with her legs still tightly clamped around his waist, and carried her upstairs, kissing her every step of the way. When they reached his room he gently lowered her to the bed and fell on top of her. They kissed deeply for a long time, while he kept his body draped over hers, making sure she stayed in place. He was already starting to take control, wanting her to let him direct the action.

  She kept clawing at his shirt, trying to pull it off, but he would not let her. Instead, he broke off the kiss and straddled her prone body. He reached down, grabbing the bottom of her shirt and said, “Arms over your head Annie,” as he started to pull her shirt up her body. She obeyed, and he thought that was a good sign, as he slipped off the cotton tee to expose her sport bra. Seeing that it was a pullover bra and once her top was off he said, “Keep them there while I let those beautiful breasts free.” She complied again and in a few moments she was lying beneath him with her generous tits on display.

  He smiled at her and said, “They are spectacular Annie, but it’s a pity you keep them in such tight bras.” Then he shuffled forward until his knees were touching her tits and he reached behind his back to grab the waistband of her shorts. “Lift your legs Annie,” he said, as he started to pull them down her legs. She just stared up at him with pure lust in his eyes as she helped him dispatch her shorts and panties all at once.

  Then her eyes went wide when his hand found her highly lubricated sex and she let out a small moan when his fingers penetrated her. She reached for the fly of his jeans, desperately wanting to find and feel his cock. But in response he removed his hand from her pussy and used it to swat her hands away from his pants. “Not yet, only when I say so, do you understand?”

  She wanted to cry, ‘NO!” but she heard her voice say, “OK, I understand.” She was in such a haze of erotic heat that she did not want to do anything to stop Jason, and his tone of voice seemed severe when he spoke to her.

  “Good, now scoot up to the pillows and relax, I want to taste that wet pussy of yours.”

  He eased his grip on her with his legs and helped her slide up to the head of the bed. Once her head was on the pillows he reached up and grabbed her wrists and moved them to the vertical bars that formed the headboard. He said, “Hold onto these and don’t let go, let me do all the work. When was the last time someone went down on you Annie?”

  As she gripped the cool metal bars above her head, she said, “I don’t remember, it was a very long time ago.”

  “Then just relax and let me stir up some memories,” he said. He grabbed an ankle in each of his hands, pulled her legs wide, and dipped his face into her wet slit. It was well covered by her dark blonde bush, something he would have her fix after they were done, but his nimble tongue easily snaked into the damp tissues hidden below her bush.

  Annie hissed, “Yesssss!” with her body arching off the bed and her grip tightening on the bars of the headboard. Jason was good and very experienced, learning early on that giving a woman an orgasm with your mouth was a powerful way to seduce them. He kept her legs spread wide in his firm grip, giving her a taste of being controlled by the way he was handling her. Her ample juices tasted good and he could tell she had washed her pussy thoroughly before coming over, another good sign in his book.

  Annie’s mind was in turmoil, the feelings she was experiencing were magnificent and long denied, but she also felt a pang of guilt. But as Jason’s wonderful tongue explored her inner folds of flesh, the guilt diminished as her passion escalated. It had been over a year since had climaxed with her ex, and even though she masturbated regularly, it was nothing compared to this! When the orgasm broke over her with Jason’s lips sucking on her clitoris, all she could do was writhe in his grip while crying out, “Yes, yes, yes…”

  He could have given her more, but he had some hoops he wanted her to jump through first. So he backed off when he felt her climax and gently licked her twitching sex lips, allowing her to come down from the ecstasy she just felt. As she started to catch her breath he began to slide up her body until his face was over her heaving tits and his jean protected cock was rubbing against her snatch.

  She stared up at him and said, “Thank you Jason, that was marvelous.”

  “You make it sound like we are done. Are we done yet Annie?” she had released her grip on the bars, but Jason reached up and kept them above her head. “Did I tell you to let go yet?”

  “No…no…I am sorry Jason, of course I should take care of you too.”

  “What makes you think I am done taking care of you yet? Now hold onto the bars and keep quiet, let me tend of you,” he said, as he slowly rubbed his hard cock against her slit.

  “Ok,” she replied, not knowing what to think about this young stud. She was feeling decadent and dirty, wanting him to ravish her as hard and fast as he could. She could feel his hard dick rubbing against her slick sex and wanted him to take off his jeans and stuff it inside her. But for some reason she just lay there quiescent, waiting for him to make the next move.

  He reached down and found her panties, picking them up and wadding them into a ball, then he said, “Open your mouth Annie.”

  She looked at what he was holding and said, “No, please don’t put them in my mouth.”

  He gave her a stern look and said, “Do you want to stop Annie? The game we are playing is do as I instruct, if you don’t want to play anymore you can get dressed and go home.”

  Annie stared up at him and her wadded up panties with part of her really wanting to pursue this wicked game he was playing, but the idea of having her used panties in her mouth was still a bit revolting. There was something about the way he was staring at her that told her he was serious and she felt torn by her conflicting feelings. But he suddenly rubbed his cock harder against her sex and she felt her mouth drop open, unable to resist her raging desire.

  “Good girl, now make sure they stay in there or I may have to spank you,” he said, as he was pushing her pussy juice laden undies into her mouth. She whined a bit, but let him gag her without any resistance.

  She was rewarded when he slid back down her belly, spread her ankles again, and returned to licking and sucking her pussy. She moaned through the panty gag, as his tongue drove her right back to the edge of an orgasm faster than she could believe it possible. She shuddered and quaked as he did some strange twisting with his tongue around her clit that sent intense sparks of pleasure through her dripping pussy. She barely noticed when he let go of one of her ankles, but he caught her attention when she felt him drive two fingers deep into her pussy.

  She gasped when they first penetrated her, but once he started fucking her with them she thought she would lose her mind. Oh my God! Who the fuck is this guy? My pussy feels like it is going to explode! Her mind was filled with scattered thoughts and unanswered questions, as her body was wrenched into a sexual frenzy like she never could have imagined. His hand was pistoning inside her, slamming into her clit with each thrust while his teeth tugged her clit hood up, exposing its inner bud. It took all her strength to not pull away from this intense onslaught of sexual fury, but the pleasure was so intense she could not will herself to move.

  Jason knew she was starting to have a powerful multi-orgasmic experience, the way her body responded to his rough attention. So far everything was pointing to this bitch becoming very submissive to him. He was pressing all the right buttons and he was combining sexual ecstasy with the rudiments of obedience. Before Annie knew it she would be willing to do most anything for Jason, and he would make sure she did. But now that he had her thoroughly worked up, it was time to toy with her mind.

  He gave her a few more hand thrusts before stopping while deep inside her and grabbing her mons with his thumb, essentially seizing her by her cunt. He looked up at her and asked her, “Is she having a good time?” while tugging on Annie’s sex.

  Annie stared down at him with fevered eyes, nodding her head slightly to answer his question. Her panties were still fully tucked inside her mouth, making Jason smile knowing she was already under his spell.

  “Would you like me to take out the panties?” he asked her nicely.

  She nodded again, but he said, “First I want you to answer a few yes and no questions, can you do that?”

  She stared at him with such desire, as she responded positively again.

  “Do you like the way I play with you?”

  Nod.

  “Would you like to play this way more often?”

  Slight hesitation, but then she made a definite nod.

  “There are rules, ones that I will make. You will follow them,” he smiled as he said that.

  A look of puzzlement followed, pretty much what he expected, so he said, “You can think about that while you are sucking my cock.”

  He reached up and pulled the panties from her mouth and then jumped off the bed. Before she knew what was happening he was standing beside the bed with his cock jutting out from his now naked body. It was enormous! It was thick and long, much longer than her ex’s. He can have his little cunt, look at the cock I found! She nearly gasped when she got a clear view of it.

  “On your hands and knees and crawl over here Annie. Time to get my cock nice and wet so I can fill your hot pussy with it!” Jason barked.

  Annie was in a haze of mind numbing lust, so when Jason snapped at her she automatically dragged herself up to her hands and knees and then crawled to the edge of the bed. He stood just out of her reach, his cock pointing at her face. She had not sucked a cock for a long time and was not really very good at it when she had, but now she wanted to devour Jason’s. She looked up at him standing there, not sure what to say or do.

  But he was ready for her ambivalence, as he said, “Wiggle those tits for me while you beg me to let you suck this,” brandishing his fat member in front of her face.

  She thought that this was a nasty game and she liked it. She started to sway, making her tits swing and slap against each other. Then she said, “Please Jason, let me suck your cock!”

  He stepped a little closer, but not close enough. Then he said, “You can do better, try again and this time, call me Sir.”