Suddenly everything that was going on hit her at once. She was lying on her son's bed, completely naked with her legs spread open; she was fondling her breasts and thrusting a sex toy in and out of her pussy; she was doing this because her son's best friend had caught her masturbating and had order her to do it; and now he was taking pictures and videoing her while she did it, with the video playing out on her son's TV in front of her! Dennis was no longer her student in sexual matters...now the real adventure begins!
***WARNING*** This chapter is a bit long at 8 typed pages. But I hope you enjoy it!
Saturday, Afternoon (Day 2)
Closing her eyes she removed the vibrating toy from her pussy and just lay there trying to catch her breath. After several minutes her body stopped trembling and her breathing slowed to slow, deep breaths. When she finally felt the last sexual tensions drain from her body Cindy opened her eyes and looked up at the smiling face of her son's best friend. "Did you enjoy that?" she asked.
"Mrs. J that was totally awesome!" he said as he smiled down at her. Then, "I want to do that to you now."
"Dennis, before we continue I need a quick break." Cindy said as she lay there. "I don't think I've ever cum that hard while playing with myself before." Cindy reached over when she realized her toy was still vibrating and shut it off. Looking back at Dennis she asked, "So Dennis, is this the first time you've watched someone masturbate?" Cindy realized that sounded awkward, especially since she meant to ask if he'd ever watched a woman masturbate. But when Dennis suddenly went beat red and looked down a powerful curiosity came over her. "And may I ask who it was?" she asked him carefully. When Dennis still didn't respond she decided that this was too interesting to just let go. Besides, her body was starting to respond to her curiosity. "That was not a fair question for me to ask Dennis, I'm sorry. But I am curious and kind of excited to hear you tell me about the experience." She said as she watched for his reaction.
Still a little red in the face Dennis looked up and said, "It's just kind of embarrassing Mrs. J. I'm mean, it's not anything like what we were just doing. It was just kind of being in the same room, not really watching..." Dennis didn't really finish the sentence, he just let it go.
Now Cindy's curiosity was peaked, "You were in the same room with someone else while they were masturbating, but you weren't watching. So why was this other person masturbating and what were you doing while this was going on?"
"We were watching, some videos, and I was...I was masturbating too." he said before looking down again.
Cindy felt a slight jolt of excitement race up her spine when she asked, "So, it was you and another guy watching, pornography, and you were both masturbating while you watched it?" Dennis looked back down when she asked that question, so she said “Dennis, if you really feel uncomfortable talking about this then we can stop, but I really would like to hear about it. It kind of excites me to listen to other peoples experiences. In fact, you might get to use my toy on me sooner if you can get me excited now.” She said.
“Really Mrs. J?” Dennis looked up and asked hesitantly.
“You remember this morning when I asked you why you came into my room last night?” When Dennis nodded she continued, “Well, I just wanted to hear your side of the story, so I could understand exactly what happened. But, I also got exited listening to your side of the story. I’m pretty open minded about a lot of things Dennis, so I’m not going to judge you if you tell me something that might seem awkward…I promise. In fact it might just excite me, and I think you remember how I am when I get excited, don’t you?” Dennis smiled, blushed and nodded all at the same time. Cindy continued, “So wouldn’t that be worth sharing this story with me?” When Dennis nodded again Cindy asked, "So what were you watching?"
Dennis looked down for second, then looked back up and replied, "Well, we watch different things and...um, you know, just the normal stuff."
Cindy’s body was still feeling the effects of her last orgasm, not to mention the weed she’d smoked earlier, and felt a slight tingle when she realized, "You've done this more than once then..." Now she was definitely interested in hearing this story..."so did you talk about what you were watching?"
"Yes, we talk about what's on the screen." Dennis said as he looked down again.
Cindy was intrigued by his candid responses to what was obviously an embarrassing subject. "What do you talk about?" Cindy asked as she wondered if this was going to lead to a discussion about circle jerks, ‘that would explain his embarrassment’ she thought with an inner chuckle. "Do you talk about what you want to do with the woman?"
"Yes" Dennis replied without taking his eyes off the floor.
Cindy felt herself starting to feel a little naughty for pursuing this discussion, but she found she had to find out more. "What kind of women do you two like to watch?" When she saw Dennis look up suddenly with an odd look on his face she realized she had made an assumption. Thinking for a moment she asked, "Dennis, is there more than two of you involved in this little activity?"
Dennis thought for moment before looking up at her and answering, "There's just a few of us, we're kind of a club."
"A club? Does this club have a name?" Cindy asked feeling even more naughty. She suddenly began to wonder if her son was a part of this club, after all Dennis and he were best friends.
"We call ourselves The MILF Club," he answered.
"MILF? As in...?" Cindy asked slowly.
"Mothers I Like to Fuck," Dennis answered, looking at the ground again.
"So the pictures you were looking at on the computer last night are the type of women you guys like to masturbate to?" She asked
"Yes." He answered.
At this point Cindy began to feel a little more then just naughty, she was starting to get a little turned on, so she asked, "So do all of you like older women?"
"Oh hell yes Mrs. J, Gary's older brother told him...um, I mean, one of the guys' older brothers told a couple of us how hot MILF's were! He's in college and said that he, um, well kind of hooked up with the mother of one of his roommates and she was way more exciting then any three girls his age he had ever dated."
Cindy was really getting into the idea of several young men Dennis' age sitting around masturbating to videos of women her age. As she envisioned a group of his friends sitting around a computer all ogling HER nude body on the screen she reached down and began to softly trace her figures over her smooth pussy. She watched as Dennis’ eyes opened wide while looking down at her naked body.
"And what do you think The Club... would think about me?" Cindy asked as she brought her other hand up to fondle her breasts and pinch her nipples. Her breathing was coming faster now as she pictured a group of her son's friends masturbating to nude images of her.
"Mrs. J they'd go nuts if I showed them the video of you. I’d have Stud status for months!” Dennis answered eagerly.
At that moment Cindy suddenly remembered the video camera sitting on her son’s desk and pointed at her! Looking over she spotted the camera, and her naked image on the TV it was hooked up to. She couldn’t imagine how that little detail had slipped her mind. ‘I guess good weed and a great orgasm will do that to you.’ She thought. But something was different, there was a small white symbol flashing on the TV and the little red light on the camera wasn’t on. After a moment she looked up at Dennis.
Dennis had also turned to look at the camera and now looked back at her again. “Oh, put it on pause after that great finish Mrs. J.” Looking back she saw that the “symbol” actually was the word ‘Pause.’
“Dennis, did you plan to share this video with your Club?” Cindy asked as a slight shiver made its way up her back. She realized that although she had slowed her hands movement over her body, she hadn’t completely stopped caressing herself. Again the image of several young men stroking their dicks while they watched her masturbating on a video started to really excite her, despite her misgivings. Looking back at Dennis she found him looking back at the floor. “Dennis, its very flattering for a woman my age to get the attention of younger men…and as much as it excites me to imagine being the sexual fantasy of handsome young men such as yourself, it would be extremely embarrassing, if not dangerous, if word got out about this video…especially after half the boys in your school saw it.” Despite the reality of her words, Cindy could help as another shiver shot through her body at the thought of an auditorium, full of young men all stroking themselves while watching her video, flashed into her mind. The thought was almost overwhelming and she realized her hands had picked up their pace again on her pussy mound and breasts. Her breathing started to pickup its pace as well.
Dennis had been watching her hands the whole time and was visibly excited himself as his hard-on pressed against his shorts. Cindy watched as Dennis was obviously thinking hard about what she was saying and what she was doing. She realized the irony of the conflicting messages his young mind must be picking up here. He looked at the video camera and back at her.
“Mrs. J, there’s no way this would get out! It’s a real exclusive club, only a few of us, and your secret would be totally safe, I can promise that!” Dennis said as he looked from her eyes to her hands playing with her body. “And you'd definitely be the star of the collection. The guys are real protective of the club’s secrecy and wouldn’t do anything to jeopardize it!” Dennis was obviously eager to convince her.
“Dennis, young men will be young men. And although some are more, extraordinary then others…” Cindy began, then moved her hand away from her pussy and patted the bed next to her. Dennis slowly came over and sat down beside her. When he did she took his hand in hers, gave it a little squeeze and continued…”, and although you may trust your friends, you can’t possibly know that one of them might not decide to share a secret this exciting with someone outside of your little group.”
Dennis was deep in thought as he sat next to her. Cindy felt his hand turn over so he could hold hers. A little jolt of excitement shot up her back when he started lightly caressing her hand with his fingers. Cindy didn’t want him to think she was trying to put him off so she offered, “Dennis, just because there are only a few people in your club doesn’t mean it’s actually exclusive, it just means it’s a small club. And I don’t mean to cause you to distrust your friends, but how can you know that this video wouldn’t get out.” She watched him closely as she said this and hoped he would feel that she didn’t not trust HIM. She squeezed his hand and was rewarded when he looked up at her again.
Dennis looked at her a moment and then said, “The club really is exclusive Mrs. J. We have some very specific, requirements…and every member has to meet them. I guess the collection itself guarantees our secrecy.”
Cindy’s curiosity was peaked now. “What exactly what do you have in this collection, Dennis?"
"Well, to get into the club you have to...have pictures, or a video of..." Dennis started to blush as he paused in his explanation. When Cindy gave his hand a light squeeze he continued, "...you have to have pictures, or a video of your mother…” Dennis took a deep breath, then “…either nude or, having sex."
Cindy’s breath caught in her throat and a tingling shiver shot up her back as she realized what he was saying. Hesitantly she asked, "So you have...a video, or pictures of your mother…that you share with The Club?" Cindy gently squeezed his hand while her other hand began to softly caress her breasts again. This story had just gotten her body’s full attention and she was eagerly waiting for his answer.
Dennis turned beat red, but he didn’t look away from her. He did look down at that hand caressing her breasts though. “Yes…” he finally answered, “…a video…” he paused again before continuing, “…several videos actually.”
As another jolt of excitement shot up her back Cindy suddenly realized she had two needs; one to hear more about that club, and the other was for Dennis to touch her body. Squeezing his hand again she pulled it over and placed it on the smooth mound of her shaven pussy. Dennis looked down at where his hand now was, and when he looked up at her face she asked, “Is she just nude, or is she...having sex?" Cindy’s breathing began to deepen, both in eagerness to hearing his answer and because he was now lightly caressing her shaved pussy.
Dennis was still looking down at the smooth pussy he was now caressing when he answered her, "She's having sex."
Cindy brought her other hand up and was now caressing both breasts at the same time. She was still only touching them softly as she wanted this to last, but she was definitely getting excited by this little secret Dennis was telling her. After taking a deep breath she said, “Describe what she’s doing in one of these videos, something that really turns The Club on.” She had to take another deep breath before she said, “Describe it as its happening, as if you were watching it right now.”
Dennis looked at her a moment, then looked back down at his hand on her pussy again. Then he asked, “Can I record this…for The Club?”
Cindy just looked at him for moment, and then looked over at the video camera sitting on her son’s desk. A moment later she felt his hand leave her pussy. She looked at him and saw his hand was now resting on the bed on her other side as he leaned over slightly just looking at her. ‘Oh he’s good,’ she thought, ‘I didn’t teach him THAT.’ Thinking for a moment she answered, “You may record it...” her decision caused another jolt of excitement to race up her spine, “…but we need to talk about it more before I agree to let you share it.”
Dennis looked into her eyes and smiled. Cindy had to suddenly take a deep breath at the response his look was causing her body. “Agreed.” He responded as he got up and walked over to the desk.
“And…” she suddenly said, “…I’d like to see it on the TV, please.” Again she felt her body respond as he turned and looked deep into her eyes. She watched as he looked to the camera and then at the bed. He made a slight adjustment to the camera’s position. Cindy watched the TV as he did this and wondered if he were trying to find an angle where his body would not block the shot. As he adjusted the camera she saw the image in the TV get larger and then smaller. After a minute he seemed satisfied and came back to the bed.
As he walked back to her Cindy realized that she probably didn’t have to worry about a question that had been burning her mind since he mentioned the club. If admittance to The Club required that EACH boy have a video or picture of their mother’s naked body, or of her having sex, to share then her son Bobby couldn’t be a member. She knew a lot about teenage boys from her youth and had gone to great lengths to ensure she didn’t add to the discomfort of puberty. She was by no means a prude, but had always been careful not to give him opportunities to sneak glances down her shirts, or up her dresses. And though her bathrobe was kind of short she took great care not to flash him. She knew he did on occasion try to sneak a peak, and she felt a little flattered by it, but he was her son. Of course that was before she had seduced Dennis. Now the thought of her son sneaking a peak caused her to feel an emotion a little stronger than mere flattery. A small shiver caused her to close her eyes as her body trembled slightly.
When she opened her eyes again she saw Dennis standing at the foot of her son’s bed looking down at her naked body. His smile as he looked over her nudity reaffirmed that he liked what he saw. The bulge in his shorts told her how much he liked it. She watched him pull the camera’s small remote control out of his pocket and point it at the camera. Looking over Cindy saw the little red light on the camera come on and the ‘pause’ symbol on the TV screen go off. Then Dennis walked around to the opposite side of the bed this time and sat down. Cindy realized he did this so his body wouldn’t block the camera’s view. Now she watched the TV as he reached out with his hand and began to gently caress her pussy.
As her hands found and began to softly caress her breasts she looked up at his and said, “Now tell about your mother’s video.”
Dennis looked into her eyes for a moment longer before looking down at his own hand as his fingers continued lightly stroking her smooth pussy lips. “She’s lying on a soft rug or blanket of some kind...” he began, “…she’s naked with her legs spread open, wide open.” Cindy slowly spread her own legs open as wide as she could on her son’s twin bed, Dennis’ body limiting one right leg. Dennis looked up at her when she did this and then back down at her pussy. “Her knees are bent and her feet are touching each, kind of close to her…ass.”
Cindy had to smile. Here he was describing to her his mother’s sexual position in a sex video and he hesitated when he had to mention her ass. ‘I guess I didn’t destroy his innocence completely,’ she thought. Closing her legs she brought her feet together. Then she slowly slid them up the sheets until her heels touched her ass cheeks. Dennis had lifted his hand from her pussy and watched until she was done. Then a huge sheet-eating grin spread across his face as he looked up into her eyes and then back down at her crotch. When he continued to just sit there looking at her new position, huge grin still plastered on his face, Cindy had to ask, “And just what is so amusing?” Normally she wouldn’t mind indulging the young who had brought her so much sexual pleasure, but she was in desperate need again and wanted him to continue describing his mother’s video. His sudden blush told her this was going to be interesting.
“For a moment there, I was imagining you actually acting out the video, the whole video…and wondering if you would really do it or not.” He admitted.
Cindy smiled as she realized that’s what it looked like she was doing, to him. The thought that it might actually turn him on, to act out the same sexual situation he’d watched his mother do in the video excited her greatly. “Would you like that Dennis…would it really turn you on, if I acted out the scene you’re describing to me?” She couldn’t begin to count how many orgasms she’d had because of his desire to please her. If he had a secret desire, an Oedipus fantasy, then she’d be more then willing to let him use her in proxy to fulfill that fantasy.
“Yes, it would REALLY turn me on Mrs. J!” He answered her eagerly. His face took on a look of wonder as he asked, “Would you really do that?”
A sudden intake of breath caused her chest rise up sharply, caused by the feelings coursing through her body. Dennis noticed it too, she realized as his eyes followed the sudden rise and fall of her breasts. She reached up and guided his hand back down to her pussy and said, “You’ll just have to finish telling me about this video and find out.” She smiled at him as she resumed caressing her breasts.
The grin on his face faltered slightly and he just stared at her for a moment before saying, “Yes ma’am.” Taking a deep breath Dennis looked back down at her pussy again and began to caress her. “Well, she’s on this soft rug-looking-thing, with her knees bent and legs spread, and she’s pinching her, nipple with one hand and…rubbing her, pussy with the other.” Cindy began to lightly pinch her nipples in response to his mother’s actions. Dennis looked up at her breast, then at her and then began rubbing her pussy, just as he described it.
Cindy’s back arched as his hand began pressing harder on her pussy mound, especially when his fingertips began rubbing over her sensitive clit. She’d met his mother before and considered her an attractive woman. Now she used that image to picture just how she would look like doing what Dennis was describing.
“She starts really twisting her nipple and then pulling on it so the breast begins to lift up.” Cindy immediately pulls both nipples upward, lifting her breasts and starts twisting them. She’s immediately rewarded as another shiver races up her back. Dennis continues, “Then she pushes her middle and ring fingers into her…her pussy.” Cindy’s back arches again and a soft, “aaaahhhh…” escapes her as Dennis slowly pushes two fingers inside of her. Cindy closes her eyes and again imagines his mother in this very scene, except she visualizes Dennis doing to his mother what he’s doing to her now. “Ooohhh….Oooohhhhh…”
“She starts pinching and twisting her nipple even harder as she really starts pushing her fingers into her…self really hard and fast.” He said as he thrusts his two fingers into her pussy harder and faster. Cindy’s back again arches off the bed as she in turn starts really pulling and twisting her nipples to match his narration. Suddenly she feels one of his fingers rubbing against her clit and suddenly, “Ooohhh…Aaahhhh…OOOHHH MYYY GOOO…” her hips started bucking upward against his fingers and both hands let go of her breasts and grab the sides of her son’s mattress as her orgasm washes over her. “Oohh Dennis…faster…Aaahhh...faster Dennis…Oooohhhh…Aaaaahhhhh…” Dennis starts thrusting his fingers into her pussy as fast as he can. He reached over with is other hand and grabbed a nipple in a two-finger death grip and began twisting and pulling, hard. Cindy’s whole body started trembling uncontrollably as she reached down with one hand and began pressing down on a spot just above her clit, mashing downward. As she cried out in passion and her hips began to thrash about as her orgasm continued washing over her, wave after passion filled wave. Again and again her hips thrust upward until finally she felt her passion falter. At some point Dennis released her nipple and pulled his fingers free of her. Cindy never noticed.
Finally she relaxed for her body lie still, but it took another minute for her breathing to begin to slow. Before it slowed completely down she opened her eyes and looked right at Dennis. After another deep breath she asks, “What happens next!” Even after her orgasm she feels a need within her to complete his fantasy. Dennis just looked at her for a moment and she said, “Its OK Dennis…I really NEED to hear the rest…trust me, I’m just getting started young man!” With that she watches as Dennis gets that wide grin again.
“Well, after several minutes she looks like she getting really excited…then a man walks into the scene, from by her feet, and kneels down by…my mom…he’s naked too…” Again a blush comes over Dennis, but he continues, “…and she reaches up with one hand and grabs his dick…then she… starts jacking him off.”
Cindy leaned over and grabbed the top of his shorts with both hands. She pulled them down as far as she could in his current position. She tugged him towards the edge of the bed until Dennis scooted off the bed stood up next to her. Pulling his shorts all the way down to his knees she then reached up and grabbed his dick and started jacking him off. She heard his sudden intake of breath, looked up and saw him close he eyes and exhale a deep breath. After a moment of pulling on his dick she asked, “Then what happens?”
Dennis opened his eyes and looked down at her. With her jacking him off it took him a moment, but then he said, “After a couple of minutes…she leans over…and starts…starts sucking his dick.” Cindy realized he must feel really awkward describing this sex scene involving his parents. But she knew how to add degree of difficultly to his situation, so she leans over farther and took his dick into her mouth. Again she heard his sudden intake of breath and felt his body stiffen just a bit, but then it relaxed a bit. After a minute of sucking him she took her mouth off his dick, started jacking him off again, and said, “Dennis, now what happens?” She quickly replaced her hand with her mouth and continued his blowjob. She felt his fingers begin to spread her pussy lips, then he said, “The guy reached down and started fingering my mom’s…pussy.” Suddenly one, then two of his fingers were inside her pussy sending incredible feelings shooting through her. Cindy really started sucking his dick now. She wanted to return the flavor he’d given her more times then she could count, literally.
Suddenly Dennis pushed her off his dick and back down on the bed. Cindy was totally taken by surprise and had no clue what she had done wrong. Looking down at her Dennis said, “Then the guy pushes my mother down on to the rug…” He removed his shirt and began climbing between her spread legs, “…and then climbed between her legs. Then my mother reached done and guided his dick to the entrance of her, pussy.” Cindy quickly reached down, grabbed his dick and began rubbing it against her wet pussy.
Without warning he shoved his hips forward and buried his dick into her pussy in one thrust. Cindy cried out as a spasm of pleasure shot through her, “AAAHHHH…”
Dennis said, “He shoved his dick into her and then began fucking her without mercy.” Suddenly Dennis pulled back and began fucking her for all he was worth. Again and again he pounded into her and she felt herself suddenly on the verge another orgasm. She grabbed his shoulders and held on, trying to match him thrust for thrust. But the sudden roughness of his actions and his jack-hammer like thrusts sent her over the edge yet again. “OOOHHHH…MMMYYY…GGGOO!” she cried out as her body once again began thrusting, and thrashing, and giving in to total abandonment. She had no say or control and she didn’t care. This animal of young man owned her at that moment and she’d do anything to make this moment happen again and again. “AAAAHHHHEEEEAAAA…” she cried out again as another orgasm began before she thought the first one was even finished. Again and again her body was wracked with passion. Again and again she met his thrusts until she just couldn’t think straight anymore. Soon she just lay there gasping for breath as another, smaller wave of passion rolled over and through her. Eventually she lost all track of time as she drifted off in a completely euphoric state.
Cindy suddenly opened her eyes as another wave of passion washed over her. This one was smaller, but it was enough to cause her body to tremble with pleasure. Dennis was still inside her, but he was no longer pounding away with reckless abandon. He smiled as he continued fucking her with slow, gentle strokes. “Wow…” she said smiling up at him “…that was great! Well, since you obviously haven’t cum yet, is there more to the video?”
Dennis smile again and said, “Yes, but I thought you’d want to be alert enough to hear it before I continued.” Then he asked, “Did you just pass out?”
“Dennis, it’s been a long time since I’m cum that hard, that often.” She said. “And although a woman can experience more orgasms that a man, it can still be exhausting. So where did leave off in the video?” She asked.
“Lets see, after my mother had two or three orgasms – the club actually has been debating the official count since we first watched the video – the man finally cums inside her. Then he rolls off her, gets up and sits down in a chair just behind her. My mother then rolls over, gets on her knees and starts sucking his soft dick.”
‘I guess she planned to fuck him again. This must be where Dennis gets his stamina.’ She thought as she wondered if that kind of thing really ran in the family. Her ex-husband had pretty good stamina, especially when drinking. ‘Now where did that thought come from.’ She wondered to herself. As she was musing Dennis suddenly pulled out of her, walked to the head of the bed and sat down on the headboard. Cindy immediately rolled over, got on to her knees and took his dick into her mouth. ‘Well…’ she started thinking, ‘…since he’s still hard I guess we’ll be moving to the position soon.’ Taking his dick out of her mouth she started stroking it with one hand as she looked up and asked, “Now what happens?” Before Dennis can answer Cindy replaces the hand stroking his dick with her mouth and starts back into a good rhythm.
“Well, then the man reaches up with both hands and pulls her head down on his dick as she sucking him…” Dennis tells her. Cindy then feels his strong hands on the back of her head gently pull her head down until his entire dick is buried inside her mouth. He holds her head firmly in place and says, “…and then a second man walks in, kneels behind my mother and positions his hard dick at the entrance to her vulnerable pussy.”