Your mother has been out of work for a while now, but that doesn’t stop you from asking her for cash every now and then. Usually, she gives in, hands you a twenty and you head off – most often to the strip club. But today, she tells you no. You’re surprised, but you figured the well must run dry at some point. She’s standing in front of you, telling you how she doesn’t like that you go to the strip club with her money, especially when things are so tight. She’s dressed in a tight black skirt and a button up shirt – ready for an interview. You watch her check her outfit, smoothing her hands over he r curves and settling the fabric. She looks so hot.
It’s impossible not to get hard watching her, and when she turns around, she notices. Shocked, she tells you how inappropriate it is, turning around and giving you a great look at her ass. Of course, you being so blatant, she catches you. She freaks out, telling you that she knows your staring, that you think about her when you masturbate. She’s not wrong. You tell her that you’re not leaving the room unless you get cash or she shows you something. She acts offended at first but you can tell she’s considering it. It’s a crazy request but you have to try. She’s just so damn sexy.
Shockingly, she agrees, stripping down and telling you to stroke your cock. She lightly bounces her ass, touches her breasts, all while telling you to hurry up, get it over with. You tell her you need something more. You need her to tell you to jerk it. She resists at first but not for long. You can tell she sort of likes it. She starts to make jerk-off motions with her hand, pumping her f st as though its on your cock. You can’t believe it, you never want it to end! But she’s had enough. It’s gone on too long! She gets on her knees and crawls to you, taking your rock-hard dick into her hand. She tells you that she needs this to be over with, handing you her panties to sniff while she puts you into her mouth. She instructs you on how to sniff the dirty gusset while she deep-throats your cock expertly! You can’t believe this is happening. You’re going to do everything you can to draw this out.
But she’s determined. And your starting to see a glint in her eye…what does she want? After some expert cock-sucking and stroking, she tells you that she has an idea. “I’ll give you what you want. The ULTIMATE taboo, if you’ll just commit to providing for me. No more job searches, no more talk about finding a job just…this. This is my contribution. C’mon, I know you want it. To fuck your mother. Just three feet over there, on the bed. I can give you that. If you just commit to your mother.”
Looking down at your mother on the bed, you can’t believe this is going to happen. Bareback, you slide into the wet cunt of your sweet mother, who gasps at first, acclimating to your thick cock, before she grinds onto your cock, bouncing her hips and making your cock drive deep into her. Pushing against her cervix, pressing your cock against her womb while its ready to explode…you can’t cum inside her, that’s what she said at first but now…she’s giving in, she’s begging for your cum. You groan, feeling a thick load pump from your balls, depositing deep inside your mother, buried inside her, filling her with potent sperm!

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You didn’t plan on this happening. It wasn’t like you signed up for that hook app because you knew she was on there. It’s just…when you saw her, her profile. Zero miles away. Her cleavage pouring out of her shirt…your mother. You knew what you had to do. You logged out and created a new profile. You used a picture of a guy on the cover of a romance novel and swiped right. On your mom. No surprise, she swiped right on you, too. Well, sort of you.
It was way easier than you thought to convince her that you just didn’t like to put your image out on the web, for anyone to have and use. After that, it was a matter of telling her what she wanted to hear mixed with some lines from 50 Shades of Gray, and your mother was smitten. Like, really, really smitten. Like, agree to be anally trained, send a stranger pictures of her gaped asshole smitten. You didn’t realize you were going to take it this far. You really didn’t realize you wanted to! But when she started opening up about how inexperienced she was, how she wanted to be more adventurous, there was a part of you that, son or not, wanted to give that to her. She deserves happiness. Passion. All of it. And if you had to be the one to give it to her…so be it.
You knew eventually, she’d want to meet up. You didn’t want to stand her up, but what were you going to do? I mean, you had her eating out of the palm of your hand, doing whatever you asked, whenever you asked, but still. That would be a bridge too far, no? But you had to try. So you agreed, “you” would go to her house. When the day arrives and you show up on her doorstep, she’s eager to get you out, telling you that she has a date. She’s wearing the outfit you told her to wear – sheer pants, gold thong, tiny bikini top and, under that tiny gold thong, a glass buttplug you sent to her.
You tell her you ran into her date outside and he gave you something to give to her. He told you to tell her to go put it on. She smirks, taking the small bag from you, and goes into the bathroom. Quietly, you creep to the door and peep in, watching your mother pull from the bag an even bigger plug. It’s the biggest thing she’s had in her ass. Almost as big as your cock. You watch her slide it in and groan, and you know this is going down, today. When she comes back from the bathroom, you decide to tell her.
She’s aghast at first, but you use the words you know she loves, all the dirty talk and little phrases you know make her pussy wet. You can’t believe you’re doing this to your own mother! But the way she squirms and mewls is making your cock rock hard and it would be a tragedy to waste all that anal training, wouldn’t it? Reluctantly, she agrees. You know she’d like to bend right over and give you her ass, but she’s gotta put up a front. A show of resistance, however fake and futile. And the facade does fall, once she pulls her panties down and shows you that thick glass plug gaping her asshole. You make her play with herself for you, stroking her pussy while she works the plug, pushing it, popping it up, showing you her stretched asshole. It doesn’t take long before she’s bent over the coffee table, sliding her tight virgin asshole onto your throbbing cock. You watch her work her ass onto your dick, grinding and pumping her hips until she can’t take it, until she’s bouncing hard and long on your dick, bringing herself to an intense anal orgasm, the spasms making your own orgasm follow quickly. You spunk deep inside your mother’s ass, then you make her pull off, dripping the massive load onto the granite table. Then, just as you discussed, she slurps the cum from the table, like a well-trained slut.

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Your dad recently started working from home which has really put a damper on your relationship with your mother. Before he started his new schedule, you and your mother would spend hours each day, exploring each other’s bodies and making one another cum over and over. She’s sexy, young for a mother, tattooed, wild…did you mention sexy? Being with her is second to nothing else in the known universe, and without your alone time, the sexual tension between you two is off the charts, so when dear old dad announces he has to go away on a business trip, you two feign disappointment, telling him how nice it’s been to have him around, while you secretly celebrate the forthcoming alone-time together!
When the day comes, you waste no time, going directly to her bed and finding her laid out already. She immediately crawls towards you, pulling your already hard cock out, stroking your desperate throbbing cock while she dirty talks you, a skill she has mastered completely, making your cock-head drip with pre-cum as she teases and draws you in, pulling you forward onto the bed and on top of her, guiding you deep inside her and imploring you to fuck her, fuck her harder, until her already soaking wet pussy gushes around your cock and she orgasms hard, moaning loudly, lost in herself. She wraps her arms around your shoulders, pulls you in tighter, coaxing you gently, telling you to cum, kissing you gently and gasping as she feels your hot load erupt inside her.

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Your new girlfriend has invited you to meet her mother, which means driving out of town and sleeping at her mother’s house. She’s a sweet woman, and honestly, a bit of a smokeshow, if you’re being completely honest. You’d never say that to your girlfriend, of course, especially because her mother’s even sexier than she is. Again, you’d never tell her that. You’re not an idiot.
Being no idiot, you don’t have to think too long about what to do when her mother sneaks into the guestroom, late at night, and sits on the end of the bed, telling you that she needs to make sure you resist the temptation of going into her daughter’s room tonight…and that means jerking off. While she watches. “I have to make sure you do a good enough job, right?” she says, smiling.
You pull your cock from your pajamas and stroke as she leans back, revealing her low-cut lingerie, her big breasts spilling from the silk fabric. She tells you to stroke it nice and slow, so you get everything into your balls and are able to empty them of everything. You start to get the feeling that this isn’t just about temptation…especially when she snakes a hand down between her legs and starts to touch herself.
It doesn’t take very long before she’s admitting that she does this with all her daughter’s boyfriends. It’s not like they don’t want it, she says. They always want her. Want her more than they want her daughter, even. She starts to touch your balls, massaging them, milking you towards a huge orgasm, as she tells you all about her daughter’s boyfriends, how they use her, how she loves being a dirty slut for all of them, in all her holes. She’s got you tugging your cock and groaning as she explains all the things she can do, all the dirty, filthy things she can do for you. Your powerless to this dirty slut’s wiles, as you lay back and watch your girlfriend slutty mother mount you, riding you hard until she had a huge, spasming orgasm all over your dick. You love the way she takes it bareback, groaning and begging you to fuck her back, to fill her with cum, to make her your filthy, dirty little slut!

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Ever since that day last week, all you can think about is seeing your mom like that again. It’s been awkward, both of you avoiding each other, not wanting to talk about it, but you think that maybe she wants it again, too. Sometimes she smiles at you, just a little smirk, before quickly looking away like she’s embarrassed. Sitting on the couch, you decide to call her bluff – to stare and not stop until something happens. Finally, she puts her book down and says that you should talk.
“What happened was…totally wrong,” she says, but you can tell there’s a part of her that wants to say something else, something more. You can sense it. You ask her to talk to you about it, about what happened, and the two of you start to discuss how you feel about it. You make it abundantly clear that you enjoyed the experience, enjoyed watching her touch herself for you, enjoyed jerking off to her naked body. You can see that she’s getting more and more aroused as you tell her this, so you keep it up, rubbing at your hardening cock through your pants until your mother confesses that she wants it to happen again.
That’s all you need to hear to pull your throbbing cock out and start stroking. She’s lost in lust the second she sees how hard you get for her, touching her breasts, sliding a hand between her legs and moaning as she watches you. You stroke just how she tells you to, long, slow movements all the way to the base of your cock, making precum leak from the head, which your mother tells you she’d love to lick clean.
“But no touching,” she says, “that would be very, very bad.” she takes her breasts out of her shirt, teasing you with them, before bending over and pulling down her yoga pants, unsnapping the crotch of her leotard to reveal her already soaking wet pussy, which she fingers for you, giggling and moaning at how transfixed you are by your mother’s sexy body. She lays on the couch and tells you to get closer, to stroke right between her legs. In just one movement, you could be buried inside her, and the thrill makes your balls draw up tight. If you came right now, you’d cover her in cum.
She reaches between her legs, and asks if it would be ok for her to touch it. “Just with my hand?” she asks, tentative but overwhelmed with desire. When you say yes, you feel your mother’s hand wrap around your cock, tugging you closer to her as she moans with delight. She strokes you while she plays with her pussy, jerking you off, grazing the head of your cock against her pussy, delighting in how crazy it makes you. You can’t keep back much longer, and she can tell. She strokes you faster, asking if you want to cum all over her. “Cum on me,” she begs, “cum for me!” she strokes and pumps your cock until you unleash a huge load across her mound, her stomach, and her tits, covering your mother in a thick load! Once you’re done coating her in your seed, your mother’s eyes drop to her messy body. “Oh god,” she says, “we really shouldn’t have done that!”

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Ever since your parents announced they were getting a divorce and your dad moved out, your mother has been bringing home dates. Guys. Young guys. Really young guys…like, your age. You were upset at first, but it took you a bit to realize that the real reason behind that was you were jealous. You hated to admit it but there was no denying that when you saw her run up those stairs, pulling some young dude along by the hand, to go into her bedroom and get fucked, your cock sprung to attention. And of course, when the noise proved louder than usual last night, you just had to investigate.
What you found was a mostly-open bedroom door, looking right in on your mother and her young lover. And the things she was saying…you thought you were going to cum right there, hands free! She was calling him son, her baby boy, and herself…mommy. Hearing your mother begging for cock, telling this dude you went to high school with to “cum for Mommy…” it was too much! You knew you should just walk away but it was too hot. Of course, you can only blame yourself for getting caught.
This morning, she tells you that you need to talk. She sits you down and tells you that you can’t be spying on private moments. Frustrated, you tell her that she can’t be doing stuff like that! She’s irate, telling you that you can’t tell your own mother what to do with her body. She admits to the mother-son roleplay stuff, and you try to fight the tent in your pants. It’s no use, though. In a moment of white-hot lust, you blurt out that she doesn’t need to go out of the house to get what she’s looking for. She’s floored, insisting that you stop saying such things but since it’s out of the bag now, you’re going for it. You tell her how hot it was seeing her like that. How much you loved her dirty talk. She is begging you to stop but you don’t let up, asking her why she can’t handle it from you, when she loved it last night.
Frustrated, she cries, “because it’s turning me on!” She looks like she wants to take it back, but its too late for that. You reach down to unzip your pants, and she begs you not to. You let your cock fall from your underwear and you can see all her reservations fall away, all her self-restraint disappear as you stroke for her. She’s steadfast that you can’t touch, but agrees that you can watch one another, dirty talk, encourage. You stare down at your mother’s naked breasts, her dripping wet pussy, and stroke as she tells you how hot it is. How she’s always wondered what this would be like…

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“Thank you so much for inviting me in. I never do stuff like this, but…well, this is a big deal. Huge, really. All my son wants is some time on the field! He’s good, too! I know you don’t think so, and you have to think of the team as a whole, but I would do just about anything to get him more time. Anything. Really.”
You’re not a stranger to parents who beg for their brats to get special treatment, but normally they aren’t so…well, hot. And dressed like this. Timmy’s mom is a total MILF in her strapless sundress, which just barely contains her big, round tits. You never thought you’d be jealous of that twerp but if he got to suck on those big tits, well…anyways. You tell her that you can’t do anything to help her and she starts to toy with the top of her dress, pulling it down just a bit as she tells you just what lengths she would go to. You really don’t care either way but you push back, knowing that this lady is truly willing to do anything, that she will, in fact, take that dress down and let you do practically anything if you just act like you can’t be made to put Timmy in. She’s smirking, pulling her dress, scooting towards you, then leaning in to kiss you. You act surprised and she just goes in again, her soft lips pressing against you as she finally lets her big tits free. Your cock is straining against your pants and she leans forward, pressing her hand against you, pulling your cock out before telling you to lie back. She mounts you hungrily, her tits in your face, bouncing on your dick and starting to dirty talk like an absolute pro. Something tells you this isn’t the first time Mommy dearest has gone to bat for her son, so to speak.
Looking up at her bouncing breasts and her soft lips parted in an ecstatic oh, you watch as she cums on your cock, clearly hungry for a good lay. This isn’t just a favor for her son – she needs this dick. You tell her to get on her back and dutifully, she reclines across the couch, spreading her legs for you. You push into her wet, hungry pussy, bringing yourself to the edge of a huge orgasm. You ask her where you can cum and, like a truly dedicated mother, she tells you anywhere. You’re tempted to unload inside her but instead, you tell her you want to cover her face in cum. Smiling, she gets on her knees, looking up at you and stroking your cock against her face, draining your balls all over her lips and cheeks!

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From your hiding spot, you can see her leaning in to have her hands tied, the blindfold secure around her eyes. This is the chance you’ve been waiting for. Once he leaves, they way they agreed, leaving her to think up some strange scenario, to imagine anyone coming and taking her like, tying her up and having their way, that’s when you can make your move.
You approach her cautiously, loving how she jumps when you touch her. “Back so soon!” she coos, spreading her pussy for your rigid cock, already out and pressing against her wetness. “Oh god,” she squirms beneath you. You knew you were bigger than him and she confirms it, talking about how the blindfold makes it seem so much bigger, her sense of touch so heightened. Yeah sure, you think, it’s the blindfold, and you push deeply into her. It feels even better than you imagined and you love the way she works her pussy down, hungry for it. You keep quiet. She notes this, telling you how she likes it that way – you could be anyone, she says. If only she knew the truth of it.
Seeing how wet and horny she is, how exciting the whole ‘roleplay’ is for her, you decide to take it a step further, pulling your cock, wet with her juices, from her and positioning the head against her asshole. She sounds alarmed at first but there’s no time for that as you push your cock firmly into her asshole. She loves it, of course, and it doesn’t take long before she is bent over, bouncing her ass up and down on your cock and remarking, over and over, about how big it feels. With the tightness of her ass and the awareness that he’ll be back any minute in your head, you quicken your pace. She recognizes the urgency and begs for your cum. “That’s it,” she hisses, little bitch in heat, “cum in my ass, I want to feel it!” You unload with a thick and saved-up load, thick and voluminous, fucking it into her until it oozes out. Then, you bounce. As you make your hasty exit, you hear the door open again and his voice as he asks her what the fuck is going on…

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You still can’t believe your mom found her gloves in your room. It was such an embarrassing moment to be confronted like that! Of course, it quickly gave way to utter lust, as she slipped them on and you watcher her thin fingers flex inside the warm, cozy wool. There was no hididng that and once she saw what an effect she had on you, how big and swollen you got, well…
You thought it was just a one time thing, but only hours later, your mother comes into the living room, when everyone else is in bed, with another pair of cozy wool knit gloves. She brandishes them, smirking. She tells you she can’t stop thinking about your big, throbbing cock, that she needs to wrap her gloved hand around you again, she needs to make her son’s thick dick cum for her! You watch her drop to her knees on the living room floor, pulling you from your pajamas and expertly stroking you, running her warm, fuzzy fingers gently up and down your cock, ensconcing your dick in her velvety soft hands, until you just can’t take it. She holds out a gloved hand and strokes out a huge load onto her woolen palm!

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When your father passed away, you knew your mother would be sending for you at the boarding school where you started last year. You knew she wouldn’t want you to go back, either, now that she was all alone. But you never expected to return to a house so changed from the one you had left. It was evident first in the way your mother was acting. Sure, she was upset about your father’s passing, but not like you expected. And she seemed to be very flirty with several of the men, none of whom you recognized, that stopped by to pay their respects. In some attempt at grieving in a way that you found more appropriate, you went to look through your father’s belongings, only to find a stash of thumb drives hiding in the closet.
Popping them into your dad’s laptop, you sat on his bed and watched as your mother appeared on the screen. Then, another man. Your father’s voice behind the camera as…oh my god. You shouldn’t have watched, but you did – you watched your mother take cock after cock, each one enormous and stretching her shaved pussy as your father encouraged them, stroked them, helped guide them into your mother. Your father was a cuckold! Your cock rigid, you stroked to the videos until you had a shameful orgasm there on your parents bed. The very same bed from the videos. When you were done, you put everything back where you found it…but all of that was for nothing, when your mother sat you down the next day to “talk.” About what she saw you watching in her bedroom.
You assume that there’s a lecture on respecting privacy coming, but instead she tells you that you have a role to play in all this, now that your father is gone. What? You can’t believe what you’re hearing but your mother goes on to admit that the fiber supplement in your OJ was actually something to put you out, so that she and the neighbor boy, a former classmate of yours, can tie you up. And train you. Break you. Now that dad’s gone, she needs a new cuck to service all her strong, thick-cocked bulls. And you’re going to be that boy! You try to fight the effects of whatever it was she slipped you, but its no use. You fade into oblivion, only awakening when you hear your mother’s teasing, lilting voice. She stands before you, naked except for these sexy black thigh highs. She is instructing someone behind you, but you can’t turn. You are tied to the bed, completely immobile as she instructs the boy behind you to spread your ass and place his cock against your hole.
You try to resist but its no use. You’re not going anywhere, your mother teases, as you feel the impossibly large cock of your mother’s new bull pres against your anus. Your gorgeous, sexy mother places her pussy right up against your face as she tells the bull to push in, to pop your anal cherry with his huge cock. She taunts you as he begins to pump your virgin asshole, pressing deeper, fucking you balls deep while you watch your mother finger fuck her delicious, dripping wet cunny. You want to please her, you realize, even as what is happening to you is shameful, painful, shocking. You find yourself losing the will to fight as the massive dick in your ass bottoms out, and cums deep inside your bowels, filling you with sticky seed. Your mother has begged him to do so and now, seeing your face as you register the warmth spreading inside your ass, she cums hard and you watch her perfect pussy spasm in delight at her own son, broken by her bull.

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