3 comments/ 84549 views/ 8 favorites Mature Woman Takes the Lead Ch. 01 By: JustABitKinky Is it 2 AM already? Jim can't believe the time. It's a Saturday night and he has been out drinking since 8 PM. Earlier in the week he pretty much got dumped by his girlfriend of about 2 years and the depression hadn't settled. Like most guys in this situation, he decided to hit the bars and get completely wasted which at this point is exactly what he was. He started the night with a few of his friends but at this point was alone and about to head home. He is startled though by a sudden tap on his shoulder. Turning around he is met by quite an attractive woman in her mid 40's. Being only 25, he hasn't dated over 29 and is unsure of how to react to this approach. The fact that he is barely awake isn't helping much either. "Hi, my name is Sarah," she says boldly as she extends her hand. "Oh hi, yes, I'm uhh Jim," he replies still unsure of what's going on as he shakes her hand. "How are you doing tonight, Jim? You look quite tired and bored, figured I'd come on over and say hello," she says with the sweetest smile. Jim catches himself just staring at her face, her smile and beautiful blue eyes putting him in some sort of trance. "I'm doing ok Sarah, thanks, my friends left a short while ago and I was on my way out," he finally says. He looks her up and down, liking what he sees. "How about you? How's your night going?" he asks while smiling back at her. "I'm doing well and the night has been fun. I've been dancing with my girlfriends for the past few hours and they just left as well. I did come out tonight though to have more fun," she trails off and winks at him. He can't believe how forward she is being. He didn't expect to be having sex tonight but it looks like things might be working out in his favor. "Oh, really, I think I came out with the same intentions," he replies while winking back at her. "I'm glad we're thinking alike, Jim. How old are you by the way? You look young," she says with a smirk. He notices she isn't giddy over meeting him but so sure of herself, exuding so much confidence like she knew the outcome before she approached him. "I'm 25," he says smiling shyly, suddenly feeling out of his league. "I thought so sweetie, you're a cutie. Come on, let's go," she says smiling at him as she wraps her arm around his waist and leads him out of the bar. "Oh, ok where are we going?" he asks stupidly, feeling out of control but excited. "We're going back to my place, unless you mind Jim," she says rhetorically. Jim can't believe how lucky he is, this never happens to him, there must be a catch but at this point he just doesn't care. He's looking forward to having sex with this minx and getting over his ex. "Alright then, let's go," he says almost as if he's giving in to his better judgement. Sarah just smiles to herself and leads him to her car. Sitting behind the wheel, she starts the car and glances over to him in the passenger seat. "Ready to have some fun, Jim?" she glances over at him with that infectious smile and then looks down at his already tenting pants. "Well, I already know the answer to that hun," she says sounding excited and motherly at the same time. "Yup," is all he says as he smiles at her knowingly, his face turning a bit red. At this point they are barely 10 minutes from her house. She looks back over at him seeing he is still seemingly rock hard and can't help but take advantage of this young and somewhat shy boy who she knows she can control. "Take it out, " is all she says, focusing back on the road. He wasn't sure he heard her right and it caught him off guard. He sat there unsure of what to do or say for about a minute. "Jim, unzip your pants and show me that hard cock sweetie," Sarah says calmly, sweetly and softly but authoritatively. "Oh, thought that's what you said," he replies shyly and with a slight chuckle. This couldn't be any easier, he thinks to himself. Jim has never really been the aggressor and Sarah sure as hell seems to have sensed that about him. He also notices how much he is enjoying how controlling she is. She is so sweet and caring but knows what she wants and he is ready to follow her lead. She doesn't even respond, knowing he now understands and just awaits his action. He unzips his pants and pulls them down along with his boxers just enough to expose his cock. She glances over quickly and smiles. "Very nice Jim, keep it out until we get to the house," she says as she reaches a red light. He is now aware that they are stopped at a red light with his hard cock exposed. He is doubting anyone else is around when of course, his luck, a car pulls up in the left turn lane right along side them. He starts to pull his pants back up but she stops him by placing her hand on his. He looks at her pleadingly but she isn't phased. "It's no big deal, Jim," she looks over to her left and sees a woman probably about her age in the car alone. "See, it's nobody you know, right?" "Sorry I'm just not used to..." he trails off as he feels her hand wrap around his cock and slowly stroke him. He closes his eyes and now doesn't care who is watching. He feels her thumb rub around his cock head and he lets out a moan. Opening his eyes briefly, he sees the woman in the car looking at them with interest and resentment. He is so turned on now he could cum. The light turns green though and she releases his cock and she goes back to driving as if nothing happened. "Don't even think of touching it," she warns while chuckling knowing how frustrated he must feel now. He doesn't care much though, this is the most exciting a time he has had in a long time. He can't wait to see what happens in this woman's house. Five minutes later she turns into a driveway and announces their arrival to her house. "You want to cum badly, don't you Jim?" she asks with a devious look on her face. "Hell yes, Sarah, I can't wait to get inside," he says while starting to pull his pants back up again. "Who said we were going inside?" she says causing him to stop dressing, seeming confused. "Wait there," she instructs as she gets out of the car and walks around to the passenger side. She opens the door and sees his confused face staring back, not sure of what to do. "Pull your pants all the way back down hun," she says as she bends over his lap. His cock couldn't have gotten in her mouth faster as she starts to blow his now quivering cock. Bobbing her head up and down while she strokes the bottom half of his cock with a slight twisting motion doesn't last much longer. She senses he is going to cum and slides her tongue out along his cock and then sucks hard. He erupts in her mouth and her hands now are stroking his cock as quick as she can, getting every last drop of cum into her mouth before she swallows. Jim is still dazed and has his head back against the head rest with his eyes closed and a devilish smile on his face. "Ok, now we're ready to go inside!" she says as she stands up and catches her breath. Mature Woman Takes the Lead Ch. 02 Jim finds the energy several minutes later to get out of the car and follow Sarah inside the house. She has already gone inside, leaving the door open behind her. "In here," he hears her say. Following her voice he walks through a decent sized kitchen to what looks to be the living room. He notices she must do well for herself as he looks around and appreciates the well furnished and modern looking house. Sarah is already sitting comfortably on the couch with her legs crossed and that lovely smile planted on her face. "Oh no you don't!" she exclaims as Jim tries to sit down next to her. He stops in his tracks, unsure of what to do. That seems to be what the theme will be like tonight, he thinks to himself and awaits for her to proceed with what will surely be another command. "I prefer my boys naked, Jim. Strip for me hun," she says as she seems to get even more comfortable, ready to enjoy her private show. "Well, yes ma'am," he says somewhat sarcastically with a huge grin on his face. Standing directly in front of her he proceeds to perform the best dance he could for her which he knew really sucked. She seemed to enjoy the awkwardness and how uncomfortable he looked doing this for her. He was getting used to this already, loving the feeling of pleasing her regardless of what it required of him. After several butt shakes Jim continues awkwardly dancing as he removes his button down dress shirt and tosses it to the side. He is in decent shape and Sarah sure seems to like it as her eyes light up a bit, trailing along the line of hair running from the base of his pecs down to his belt buckle. Even though she's pretty much seen him naked already, she is enjoying this tease. He undoes his pants for the second time tonight and slides them down his nicely built legs. Stepping out of them he kicks those to the pile and follows suit with his boxers. "Very nice," she says staring intently at him. "Very nice, indeed," she continues seemingly appreciating what she couldn't see that well in the dark earlier. He just smiles back at her sheepishly feeling a bit odd standing there naked in front of her still completely clothed. "Damn I am sure going to have fun with you Jim," she says with a look on her face that says she is formulating quite the plan. "Sounds good to me," he says blushing a bit, barely able to look her directly in the eyes. "I did say to get naked, didn't I? Lose the socks hun," she says and as before it was definitely an authoritative command but at the same time was said with a sweet motherly tone which he was beginning to love. Reaching down he removes his socks and adds them the pile and now he is officially completely naked before her. "Turn around for me babe, let me see that cute ass," she says as she uncrosses her legs and then crosses them again with the other leg. He turns around for her and proudly displays his ass to her. "Mmm nice ass Jim, so cute and pudgy," she says as she continues admiring him. "Reach back and grab both those ass cheeks," she says sounding more excited than a few seconds ago. "Yes, just like that, spread your cheeks for me a bit," she continues as he does what she asks. "Oh yes, that's good, I like that view baby," she says sounding even more excited. At this point Jim is feeling quite on display to say the least but is loving the attention she is giving him. He rarely ever gets compliments like that from women. He is always going out of his way to compliment women yet here was a beautiful older women showering him compliments. He is feeling like a million bucks and is feeling more and more relaxed with her voyeurism and extreme interest in everything about him. "Lay down on the floor, on your back," she says apparently now satisfied by the view of his ass. He obediently lays down on his back for her and notices his cock is all hard again. "Hun, are you enjoying yourself?" she asks slightly rhetorically. "I wouldn't want to upset you with how I am with my men," she continues. He notices how again she refers to him and obviously many others as 'her men' and something about that gives him a thrill. "Oh I definitely am Sarah, I'm liking this a lot," he hesitantly replies fearing if he didn't she would perhaps stop. "Perfect, I just have to make sure before I continue," she says with a wink. "I have so much fun planned for you sweetie," she says again winking at him. He is not sure whether or not to be afraid but at this point he feels committed and is along for the ride. Sarah gets up off the couch and walks over to him, towering over him and looking down at his naked body. She kicks off her heels and removes her stockings. This generates a jump in Jim's cock, seeing her finally removing something even if it is only her shoes and stockings. Kneeling down she gets on her knees next to him and sits back on her feet. "Damn, she is quite flexible," he thinks. Leaning forward a bit she begins to very lightly run her fingers along his legs, down to his feet and back up to his thighs. Her other hand does the same thing up and down his stomach and chest. Eventually her one hand rests on the inside of his upper thigh while the other hand continues to lightly trace circles and lines from his chest down to right above his twitching cock head. She notices pre-cum beginning to drool out of his cock. "You better have good control sweetie. I don't want you cumming too soon," she says as she begins ever so lightly tickling his balls. He lets out a light moan as she continues playing with his balls. Using a couple fingers from her other hand, she now very softly runs her fingernails up and down his cock at a torturous pace. She continues this for several minutes but then suddenly stops and stands up. "Stay right there and don't you dare touch yourself," she says as he groans in frustration. She then walks out of the room leaving him laying there with his throbbing hard cock just dying to cum. A minute later she returns holding a large container of lubricant. Getting back in the same position on the carpet floor, she squeezes a nice amount of lube into her hands and rubs them together making a wicked sound. Carefully taking hold of his cock with one hand, her other hand goes back to his balls and massages them. She then decides to let go of his cock for now thinking he will cum too soon with what she is about to do next. Jim is enjoying the feeling of her slippery hand squeezing and playing with his balls. Suddenly her hand slides lower and then her middle finger glides downward towards his ass crack. He feels himself start to panic. "Is she doing what I think she is going to do?" he asks himself. "Aw, it's ok sweetie," she coos, still not retrieving her finger from his ass area despite the discomfort he is displaying. "It will feel really good, I promise, trust me," she says smiling wide, loving this uncomfortable introduction to one of her favorite fetishes. He is not sure if he wants her to do this but he is not moving either. Something is telling him to stay and endure what is about to happen. It's that motherly affection she is showing him and the amount of pleasure she is deriving from this that is making him stay, he realizes. Sarah takes his stillness as a sign that he wants it. Oh how she loves this. She slides her finger further down until she feels his tight asshole. During the past minute, as she expected, his cock got slightly softer so she now grabs his cock again with her other hand and begins to slowly and methodically stroke him until he is fully hard again. Once he is all hard again she wiggles her finger around the opening of his ass trying to get him to relax so she can enter him. Increasing the pace on his cock seems to do the trick as she starts to breath a bit heavier. "Yes baby, does that feel good? Hmmm? How does that feel hun?" she repeats as she gradually increases speed. "Uhhh," he groans in response as his ass lifts slightly off the floor to meet the pumps of her hand. With that, she feels him almost completely relax and lightly but swiftly slides her finger all the way into his very tight asshole. Wiggling her way in with precision. "Ohhh godd!" he exclaims not sure if he likes it yet. He doesn't care though because her slippery warm hands are becoming a blur on his sensitive cock and he is so close to cumming. She can sense this and wiggles around to find his sensitive and engorged prostate which she begins to massage with expertise causing Jim to yell out in ecstasy. "Mmm you like this don't you?" she asks with a devilish grin as he erupts all over his chest while continuing to scream out in pleasure enjoying the best orgasm he has ever experienced. "I'll take that as a yes my boy," she says still grinning as she tortuously continues pumping his cock at full speed. The submissive feeling he has felt this evening is increased by her referring to him as her boy. Again something about the way she says things like that seems to drive him crazy and she obviously knows that about him. He is now yelling out in pleasurable pain though as she is still rapidly jerking off his spent sensitive cock. Finally she slides her finger out of his ass and stops stroking his cock but not before she rubs his cock head with her thumb several times. Jim can't do anything but lay back almost motionless and spent. Sarah leaves the room for a moment to clean and dry her hands. Returning she sees Jim has found the energy to clean himself up. He is still naked though which she loves. He is sitting on the couch so she sits down next to him and puts her arm around his shoulders. "I'm glad you enjoyed yourself," she says as he turns a bit red in the face. "It's ok, you'll learn to explore certain things with me and you will definitely enjoy it, won't you?" she asks sounding a bit stern letting him know she expects a yes. "Yes, I will," he replies somewhat reluctantly. She kisses his cheek. "Good, the night is still young," she whispers in his ear. His head falls back in exhaustion as she emits a giggle. He knows she is serious though.