The MILF and Her DILF Read online

  “Very nice, now stay still and you may come when you are ready,” he said, sliding his fingers back into her very damp pussy.

  She was surprised that he planned to make her come while she held this position, and as her arousal escalated, she wondered if she could stay where she was. He was hooking his fingers into her, rubbing the inner wall of flesh just behind her clit. It was marvelous, as she could feel sparks of electric pleasure filling her sex and she knew she would come soon if he kept toying with her that way He did, and in just a few minutes she felt the wave building inside her, her legs starting to tremble as she tried to remain on her knees.

  “Ahhh…Ahhh…. OOOOHH!” she hissed, as the orgasm hit her. She shuddered and swayed, but somehow remained kneeling in place. Then the hand moved away and she felt her head pulled forward until she hit the sheets, the waves of orgasmic pleasure pulsing through her and making the moment seem surreal. She did not notice Jason jump off the bed, drop his pants, and aim his cock at her pussy. He nudged the head against her gaping slit, grabbed her hips, and driving it deep into her, ramming it right into her cervix.

  Annie’s head was spinning when she felt his shaft spear into her twitching sex and a gasp of air was forced from her when it slammed into the back of her vagina. Then she felt him start to fuck her, slowly at first, but with an ever-increasing pace. She felt new orgasms start to erupt like firecrackers throughout her body, and she screamed in feral ecstasy as Jason throttled her from behind. Reality became skewed as all of Annie’s focus was centered on her pussy and the massive organ reaming it out like a pile driver.

  As Jason thrust into Annie’s dripping pussy he could feel her body fully surrender to him, she was a pure fuck toy, just the way he liked it. Either she was easily manipulated in her depressed state or she was a natural submissive, if not both. But either way, Jason knew he had himself a real spitfire here, and he rammed her extra hard forcing moans of discomfort from her as his enormous cock ravaged her sex.

  Finally he stopped and pulled it out, letting Annie collapse face first onto the bed. He simply walked around to the other side and grabbed the delirious woman by her hair. He snapped, “Get up here and suck him off now!” dragging her toward his cock as he spoke.

  She lifted her head as his hand pulled her toward him and she saw his soaked dick in front of her. She was so dizzy that the normal revulsion she would have felt if she could think straight was gone and she gladly took it into her mouth. She sucked furiously on it, wanting to make him cum so bad. Her whole body was infused with sexual energy and all of it was centered on her mouth and tongue. The way he had made her feel, she wanted to make him feel that good too.

  Jason was impressed with her enthusiastic attempt to suck him off, but he also knew she would need lots of instruction to learn how to do it properly. But he was aroused enough watching her effort that he was able to reward her with a good mouthful of his spunk. When his cock stiffened and started to pump, she clamped down on it like a baby at a teat. She sucked down every drop, and loved every minute of it. She felt a pang of loss when he pulled the softening rod from her mouth, but smiled when she saw him offer the glass of juice again.

  She took another swig, the refreshing liquid washing away the musky taste in her mouth. Then he took the glass away, put it down, and grabbed her by the hair again, tilting her head backward. He kissed her again, driving his tongue deep into her inviting mouth. They kissed passionately, just like the first time, with Annie starting to feel an attachment to Jason and with him feeling well in control.

  He broke it off and said, “Your clothes are on the chair, get dressed and meet me downstairs. I will have some instructions for you before you leave.”

  He pulled on his pants and walked out of the room, leaving Annie wondering what just happened. One moment he was hot and adoring and the next he was cold and callous. But she buried those thoughts and crawled off the bed, walking over to the chair. She found her shorts and tee shirt, but her underwear was missing, so she looked under the chair but only saw her flip-flops there. She guessed he had confiscated them, and given the way thing were progressing, it almost made sense. She put on what was there and headed downstairs to receive her ‘instructions.’ He was playing a compelling game, and she was now happily playing it too.

  She found him in the kitchen, sitting at the table sipping on a beer. He pointed to a chair and she took a seat. Then he said, “You will go home and take a nice long bath. Then make Beth a nice supper. Is she going to be home tomorrow?”

  “Yes sir,” replied Annie, but she also said, “but she told me she was meeting some other students tomorrow night on campus.”

  “Then you will come back here as soon as she leaves, right?”

  “Yes sir,” she said, all too eager to commit to his game now.

  “Now for some ground rules while you are away from me. No touching or playing with your pussy, it belongs to me now. When you return you will bring all your bras and panties with you, the ones you wore today were unacceptable, so I disposed of them. I will decide what you wear from now on and you will never wear pants or shorts when visiting me. Only skirts or dresses are acceptable, and until I select appropriate underwear, you will wear none. Have you got all that?”

  “Yes sir.”

  “Good, Now you may go home. Oh, I may text you to do some simple things while at your house, make sure to do them properly when you receive the texts. So keep your cell phone close by,” he said, as he stood up and took her hand. He led her to the door and showed her out, watching her walk home slowly, her mind filled with many questions and even more amazing memories.

  Chapter 4: Under His Control

  Annie stumbled into her house and mindlessly walked up to the bathroom. She turned on the water and heard the tub start to fill. She removed her top and shorts and then stared at herself in the mirror. What is happening to me? Her body never felt so…alive. It was like every nerve and muscle was heightened and her swollen pussy still throbbed between her legs. She wanted to touch it, but he said she could not, so she did not. Why do I feel like I HAVE to obey him? Deep down she knew she was playing his game the way he wanted, but it felt like she had no choice now, like she had to do what he said. It was dangerous and decadent, but the normally conservative Annie was no longer constricted by her prior beliefs. He had opened a door in her mind and now she had to find out what was on the other side.

  She turned off the water and slid into the tub, wincing when her over stimulated pussy entered the steaming water. At first it stung, but in a few short minutes, after the water had seeped into her pores, she felt a wave of relaxation consume her. She rested her head on the edge of the tub and drifted off, falling into a half-sleep, where her memories of their sexual liaison filled her thoughts.

  Jason was watching her on his laptop while sitting in his kitchen. He smiled when he saw her obey him by running her bath, just as he demanded, and also by the way she avoided touching herself. He could tell she was looking at her inflamed sex in the mirror, but she kept her hands away from it. Once she stepped into the tub he finished his first beer and grabbed another from the fridge. By the time he sat back down he saw that she had already drifted off into her semi-conscious state, her submerged body still plainly in his view.

  He was still surprised by how easily she succumbed to his seduction, and he was confident after watching her at home, that she would be an earnest little student. Clearly her divorce had left her feeling unsure about her sexual future, and now he had released all that pent up desire. It was like opening a floodgate, he thought, she needed sexual validation so bad that she took to our little romp like a fish to water. But he also felt she displayed some tendencies that would make subjugating her even easier than he first thought.

  As he watched her soaking in the tub he realized that she was predisposed to serve. Everything he had seen her do since she first pulled into his driveway was now validating that idea. His only concern was that Beth would pick up on Annie’s change in n
ature and figure out what happened. He needed to keep their fling a secret between them, but if Annie suddenly showed a renewed vigor for life, her daughter might just discover what they had begun. He decided his first text to her would address that.

  He slowly sipped his beer, waiting a half an hour before sending her a text message. He typed in the words, editing them a few times until it sounded just right. He then waited a while longer, letting Annie bask in her post-orgasmic bliss. Then he pressed the send button and sat back to watch what she did.

  Her phone beeped as it sat by the sink in the bathroom and the sound startled Annie out of her sex-induced stupor. She turned her head to see the phone on the sink and she hoped it was Jason, not Beth, sending her a message. She lifted herself from the tub, grabbed a towel and wrapped it around her body. She stepped from the tub and grabbed the phone, feeling her heart pounding in her chest. Why does the sound of a text message make me feel so anxious? She wondered.

  She flipped open the phone and hit the key to display the text and it read:

  Your bath should be over by now. It is time for you to cook dinner for Beth. Just remember, this is our little secret, so watch how you behave around her. You would not want her to know you are such a horny slut, now would you?

  Annie looked at the message and realized Jason was right, she had to act normal around Beth. She definitely did not want her girl to find out about her erotic escapade and think less of her for it. Despite Beth’s suggestion that she should consider pursuing Jason, all her maternal instincts told her that Beth should be kept in the dark about this. Especially the way it was progressing, becoming Jason’s ‘sex-pet’ was not something Annie wanted Beth to know.

  She typed in, ‘No sir, I will keep it to myself…and thank you sir.’

  Once she sent it she felt a shudder run through her body. She deleted his message, and hers, afraid that Beth might see them if she kept them. But the way he talked to her, even in his text message, sent shivers of arousal through her. Why does it arouse me when he calls me such dirty names? She wondered. But like the dutiful puppet she was becoming, she remembered the first part of the message and ran for her bedroom. She quickly dried herself off and went to get dressed, only to stop when she looked into her underwear drawer. No undies allowed, she cautioned herself and she closed the drawer. She just put on a pair of shorts and a tee shirt, then headed downstairs.

  Jason was enjoying the show immensely, watching her obey every one of his commands without hesitation. He remained fixated on the Annie show for most of the night, happy to see how she handled herself with Beth. She somehow managed to revert to her old form, giving her daughter no clue about what happened that day. They ate dinner, watched some TV, and then both of them went to bed.

  When Annie retired to her bedroom Jason sent her another message:

  ‘From now on you will sleep in the nude, but you still will not touch yourself.’

  He watched her jump when her phone beeped and then race to it to read his message. When she saw it she typed a simple, ‘Yes sir,” and then she removed her clothes and crawled into bed. She got under the covers and made sure to lay her arms at her sides on top of the blanket, providing her with a barrier and making it easier to obey his command. Soon she was asleep, and Jason shut down his laptop, confident that Annie was fully immersed in his game.

  The next morning, and through most of the day, all seemed normal in the cottage, with both women still settling into their new home. Jason watched them off and on; while he was working on the scenario he had planned for Annie’s return that evening. He had decided that she would learn about bondage tonight, and how it could be used to drive her to even higher levels of passion. He was fairly sure that once he had her bound that she would sink even further into his trap, since he planned to tease her until she begged for sexual release.

  By late afternoon he had everything ready and sat down to watch his toy and her daughter having dinner together. Once again, Annie seemed perfectly normal, even though he was sure her mind was fixated on what would happen after Beth left for the evening. Then, during their banal dinner conversation, Beth said something that perked up his ears.

  “Mom? Would it be a problem if I stayed overnight on campus? Debbie said her roommate won’t arrive until next week and I am welcome to use her bed tonight?” Beth asked her mom.

  Annie paused for a moment, and then she said, “I suppose so, but be careful, OK?”

  Jason watched Annie closely after that, wondering if she would volunteer the news that Beth was not coming home that night. After he saw Beth finish her dinner and tell her mother she was going to pack a bag for the night, he watched Annie as she cleared the dinner dishes from the table. He decided to send her another message,

  He watched her leap for the phone when it beeped, quickly reading the message: When is Beth leaving?

  She typed in her response and sent it back. Soon Sir and she told me she was spending the night.

  He smiled as he read it, then responded with: And you would like to stay with me tonight?

  It took her only a few seconds to respond: Yes sir.

  Remember what I told you to bring with you, you have fifteen minutes to get here after she leaves.

  After receiving his last message he watched her go into high gear, cleaning up the kitchen in just a few minutes. Then she headed upstairs with a trash bag and by the time he switched to the bedroom camera, he saw her emptying her underwear drawers into it. He heard Beth knock on her door and say, “I’m leaving mom, see you tomorrow, probably by noon.”

  “OK honey,” replied Annie, “Have a good time.”

  By the time Beth pulled out of the drive, Annie had collected all her under things and bagged them. Then she went to her closet and picked out the sundress she had already chosen for this evening. Knowing what was in store for her, at least she thought she did, she stripped and put on the simple dress. It barely contained her braless tits and the hem came down only to her mid-thighs, making her look quite fetching. She slipped on a pair of heeled sandals, but the heels were short, something he would address in the near future. Then she left her room. He watched her head downstairs, grab her purse, put her phone in it, and then depart through the kitchen door.

  As Annie walked toward Jason’s house and another night of decadent sex, she thought her heart would pound right out of her chest. A small voice in her head kept saying, this is wrong, stop, turn around and go back. But her legs kept walking and her pussy got wetter with each step she took. Though part of her mind knew what she was doing was dangerous, her body needed the kind of relief that Jason could provide. Ever since she left there yesterday all she could think of was him, and that massive cock. What he did to her yesterday was scandalous, but the way it left her feeling could not be ignored. It was as if he turned on a switch inside her and now she was alive again. Until yesterday all her energy had been focused on Beth and her own life was just a shadow. Jason changed that; he had shown her that she was still a vital and passionate woman, one that needed what he had to offer. As she passed through the gate into his yard, she saw his silhouette standing in the doorway and she felt a lump in her throat, eager to feel his strong arms wrapped around her again.

  Jason watched her walking toward him; smiling as he thought about the demeaning things he had planned for her tonight. And now he could extend it for the entire night, glad that he could stretch out the treatment over a longer period of time. He guessed that by the time she woke up tomorrow morning she would be much closer to becoming his sex slave than she would have after the simple session he had originally planned. As she approached his porch he squared his shoulders and stood there with his arms crossed over his chest.

  When she reached the base of the steps he said, “Stop. Put your bags on the steps and kneel Annie.”

  She obeyed him, falling right back into the role he required without a moment’s hesitation. She even went so far as to spread her legs and lock her fingers behind her neck as she did it. He said
nothing else as he bent down and picked up her things and carried them into the house, leaving Annie kneeling on the path at the foot of the porch stairs. He returned in a few moments and looked down at her, very pleased that she was already totally obedient to him. He was about to test that obedience.

  “Remove your dress and hand it to me,” he said.

  Annie started to look over her shoulder, afraid someone might see her, despite the fact that they were secluded in his yard. But she stopped when he barked, “Eyes forward! I did not give you permission to look around.” She snapped her head back to look at him and then started to lift her dress off, feeling nervous as she removed the simple clothing. She then handed it to him, hoping he would let her inside and not leave her out there naked and exposed.

  But he shocked her again when he said, “Crawl around the house to the front door, I will meet you there.” Before she could digest this new order he stepped inside and slammed the door, leaving the naked woman alone in his yard.

  Oh my god! What the hell am I doing? She thought. But she quickly dropped to her hands and knees, swiftly crawling around his house through the cool damp grass. Her large breasts swayed and slapped against each other as she shuffled as fast as she could around the building, utterly terrified that someone might see her like this, even though the chances were slim. It took her only a couple of minutes to reach the front door to find Jason standing there waiting for her. He ordered her to stop again and she froze in place, now at the base of his front steps.