- Joined
- Oct 8, 2015
- Messages
- 508
Been awhile since I have done one of these, but this one was too novel and too wild to not post.
Final weekend of October. Saturday. I had gone out the night before, and been utterly disappointed with how little people and establishments were participating in Halloween festivities. I was the only person dressed up at two of the bars I checked on (my costume: a sexy devil, with horns and a striking crimson cloak). I live 25 minutes from downtown and only tried the local bars, but I really thought there’d still be more of a Halloween crowd.
Anyway, I was bummed out, because a blizzard hit Saturday morning, and I knew this would seriously damper my chances at some Halloween mischief. I went about my day as normal, including grabbing a lift, and then convinced my roommate to accompany me to the hot tub for a post-workout soak.
It was still lightly snowing, so the thought that I might meet a woman at the hot tub didn’t even cross my mind. Yet as I approach the tub, sure enough there is a beautiful woman, along with what appears to be her young teenage son. She is 5’2” or so, looks either hispanic or Italian, and is wearing a bright red one-piece that shows off her tits and legs. I say hi to her and give her my typical warm yet smirky smile as I get in the tub. She returns the greeting with enthusiasm.
My roommate and I talk for 5 minutes or so, and I eventually bring her into the conversation by complimenting her courage in braving the cold when most girls wouldn’t dare. She has been sipping on what seems like tequila, and is thus very glib and happy to have two younger guys to chat with. I also include her son, who I find out is thirteen, and build him up to his mama as he tells me about some of his achievements and interests, which she loves. I’m keeping my words pretty platonic, but there is a slight flirtiness to my tone I can tell she is picking up on and reciprocating.
I have her and her son do most of the talking, and find all about her job (nurse), some of her interests, her previous relationship, and more. I also break the touch barrier by having her give me her palm so I can see her bracelet. From here I start giving her little, incidental touches with my hand and forearm, and my legs and feet under the water. Which she also reciprocates. And she is now giving me these intense looks. The two of us start throwing out innuendos here and there. I find out her astrology sign, Cancer, and bust on her for it which makes her laugh hard. I eventually comment on her height, and take her arms and pull her towards me so we can stand facing each other. I stand up right in front of her, and stare down at her with a smirk. I’m a foot taller than her, and I can tell she is feeling very girly.
Anyway, I’m still more in flirtation mode than killer mode, since I have never been with a woman over 40, and since her son is right there. But by this point she starts abandoning tact and starts finding all these excuses to touch me as we keep conversing. And then out of nowhere she touches my right cheek with her hand and says, “You are REALLY cute”.
My roommate, who had kind of been competing for her attention, gets the message and announces he is heading back to the apartment. I tell him I will stay, and give her a sultry look. Once he leaves, I have her sit next to me, and we start touching each other, mostly under the water. I do this as I am making conversation with her son. I nonchalantly talk to him about his school and I slide my hand down her back to her ass, which elicits an expression of shock and excitement from her. She starts overtly touching me all over, above and below the water.
Just a little disclaimer before I continue: yes, she had been drinking, but this woman was not that tipsy. We had been talking about fairly involved topics, like certain kinds of surgeries and diseases she had recently had experience with, and even by the point where she started getting pretty handsy with me, she seemed very in control of her capacities. No slurring, no stumbling, no over-expressiveness, no recollecting of her thoughts, etc.
Back to it. With her son RIGHT THERE, I lift her up a bit, and slide my hand past her ass and to her pussy. It is dark out, the light in the hot tub is out (as it has been for months now), and the bubbles are on, so I am confident he won’t be able to tell what I am doing. I rub outside her suit for a bit before moving my hand out from under her. I then go over her leg back to her pussy (she is practically sitting sideways on my lap at this point), and slip under her one piece and start “diddling her skittle”
before outright fingering her.
She goes from libidinous to downright ravenous. She seems unaware her son is right there. She is staring hard at me, and with her eyes wide keeps telling me how bad I am, which I either ignore or respond to by giving her an intense look. All this time, I am still making polite conversation with her son, who I can tell is starting to get uncomfortable with how his mother is draped over me (though I doubt he knew what I was doing below the water).
Though somewhat drunk on my own power, I am reminded of a time when I was her son’s age. I was 13, and my parents had decided to go to Old Chicago for dinner. My mom was and still is a very pretty lady, and there was this drunk guy at the restaurant who was captivated by her and kept trying to talk to her and kept making lewd comments at her. Which made me absolutely FURIOUS, to the point where I grabbed the guy by the shirt and threatened him, and my dad had to pin my arm down to deescalate the situation (I honestly think I could have taken this guy even at 13 lol… I was a very big, aggressive 13 year old and champion wrestler, and he was small and drunk). This hot tub situation is fairly different, but makes me very curious what my younger self would think if he were to see me as I now am. I eventually stop fingering her and whisper in her ear to send her son home.
She goes into authoritative parent mode and has her son leave despite his apprehension at leaving her alone with a strange man. The way she goes about this further confirms in my mind that her lust for me is not just the alcohol talking. He finally leaves, though keeps texting her to see if she is ok. I smile at her and tell her he is a good kid, to which she agrees. Not expecting anyone else to surprise us due to the cold, I start touching her all over and hovering near her lips with my own, teasing her. After I start fingering her again I finally break the tension by kissing her, and then start kissing her down her neck and to her tits, which I take out. I kiss and suck her tits while placing her hand down my trunks and fingering her with my other hand (who says guys can’t multitask!). Eventually I take my trunks all the way off and insert myself in her. The water from the hot tub makes this difficult, but I anticipated this and just wanted to break that barrier before inviting her back to my apartment. We do a little bit of awkward thrusting before I pull out and go back to fingering and kissing her, and then put her tits back beneath her suit and put my suit back on. I grab her by the hand and tell her to come on, assuming the sale, and when she asks where we are going I tell her I have a very interesting ceiling I want to show her, which makes her burst out laughing. We dry off, I help her get in the robe she brought with her, and we slowly walk back to my apartment, marveling at the beauty of the light, falling snow and the great, vast night…
Once back, I have her take her boots off and I offer her bourbon, which she happily accepts. My roommate is in the kitchen, and I give him a big smirk which earns an exasperated chuckle from him. I show her around briefly before taking her to my room, and we are all over each other within 20 seconds of banter. The sex is pretty vanilla but still good. I am pleasantly surprised she is still pretty tight despite having had two kids. I am able to make her cum very quickly. Makes sense she’d know her body well enough to easily get into an orgasmic state by this point of her life.
We end up having four 15-30 minute sessions in a variety of positions over the course of the night. She has very nice legs and skin, though is of course not the same as a girl in her twenties. I was half-expecting her to have all these sexual tricks to throw at me, due to her age and experience, but she was extremely submissive and had nothing particularly interesting for me. Oh well, I enjoy taking the full reins. And she is highly orgasmic, cumming hard and repeatedly without me putting in unusual effort. She is even able to cum on command, which I take full advantage of. I make her cum especially hard in cowgirl, manhandling her ass with my hands as I thrust hard up into her, and ordering her to cum for me, then doing it again before she has had much time to recover.
Beyond that, we both drank a LOT of water. We have some deep pillow talk with her draped across my side. She tells me she is a witch (lmao), and that she can tell me a lot about myself and my future, which I entertain, calling myself an “ally to witches” (which is true in spirit; I love pagan art despite probably being a materialist). She tells me a bunch of vague, nice-sounding statements (hello Barnum Effect), though I am into it, and she is actually very good at it. I even attempt to cold read her (I used that exact term which she didn’t bat an eye to, which tells me she is studied). We chat more about astrology, and I share with her my very genuine affinity towards the Moon (which just so happened to be full that night...). After about three hours, I suggest she go home to her kids and help her find all her stuff. Turns out her apartment is virtually right next to mine lol. We passionately kiss goodnight, and I watch her leave in her soft white robe and furry boots.
The next morning I text her saying I had a good time and that I hope she isn’t too sore today. She happily echoes my sentiment back, though later in the day sends me a long text saying how guilty she feels regarding her son, that she was dealing with emotions from a bad breakup (which she alluded to the night before while we were in bed talking), and that what happened can’t happen again. I tell her I understand and ask her if she regrets the night and she tells me she doesn’t and that it was actually quite beautiful, to which I agree. We both send flirty “see you around” texts, and that was that.
…
All in all, was a fascinating and fun experience. I had never been with a woman past 40, and I certainly had never fingered a woman while chatting with her freaking son! She was very hot for her age, though I am plenty content with it just being a one-night thing. And against the odds, I still got laid despite a blizzard!
I have always prided myself on my duality and my extremity. Take my response to that fucktard that was harassing my mom all the way back then. I was ready to break his bones and gauge his eyes, yet out of a righteous sense of protection. Years later, and this time I find myself the threat to a boy’s mother’s virtue before his very eyes (though a VERY welcome one at that). I played a role in corrupting a mother in front of her son, and tantalized and excited her to the point where she threw away her responsibilities for a night to cum her brains out with me. Yet at the same time, I gave this woman a night she sorely needed (pun not intended). I gave her passion and intrigue and spontaneity and warmth, during a time in her life in which she seemed to especially need it. I was a willing subject for her cold reading and wisdom, making her feel powerful to have influence over someone like myself. I gave her son a lesson on the nature of women without showing him too much. And I’m sure I made her feel young again.
How I love being human. How I love seizing my privilege to bask in both light and darkness. I hope to only heighten my virtuosity and depravity, always in balance.
Final weekend of October. Saturday. I had gone out the night before, and been utterly disappointed with how little people and establishments were participating in Halloween festivities. I was the only person dressed up at two of the bars I checked on (my costume: a sexy devil, with horns and a striking crimson cloak). I live 25 minutes from downtown and only tried the local bars, but I really thought there’d still be more of a Halloween crowd.
Anyway, I was bummed out, because a blizzard hit Saturday morning, and I knew this would seriously damper my chances at some Halloween mischief. I went about my day as normal, including grabbing a lift, and then convinced my roommate to accompany me to the hot tub for a post-workout soak.
It was still lightly snowing, so the thought that I might meet a woman at the hot tub didn’t even cross my mind. Yet as I approach the tub, sure enough there is a beautiful woman, along with what appears to be her young teenage son. She is 5’2” or so, looks either hispanic or Italian, and is wearing a bright red one-piece that shows off her tits and legs. I say hi to her and give her my typical warm yet smirky smile as I get in the tub. She returns the greeting with enthusiasm.
My roommate and I talk for 5 minutes or so, and I eventually bring her into the conversation by complimenting her courage in braving the cold when most girls wouldn’t dare. She has been sipping on what seems like tequila, and is thus very glib and happy to have two younger guys to chat with. I also include her son, who I find out is thirteen, and build him up to his mama as he tells me about some of his achievements and interests, which she loves. I’m keeping my words pretty platonic, but there is a slight flirtiness to my tone I can tell she is picking up on and reciprocating.
I have her and her son do most of the talking, and find all about her job (nurse), some of her interests, her previous relationship, and more. I also break the touch barrier by having her give me her palm so I can see her bracelet. From here I start giving her little, incidental touches with my hand and forearm, and my legs and feet under the water. Which she also reciprocates. And she is now giving me these intense looks. The two of us start throwing out innuendos here and there. I find out her astrology sign, Cancer, and bust on her for it which makes her laugh hard. I eventually comment on her height, and take her arms and pull her towards me so we can stand facing each other. I stand up right in front of her, and stare down at her with a smirk. I’m a foot taller than her, and I can tell she is feeling very girly.
Anyway, I’m still more in flirtation mode than killer mode, since I have never been with a woman over 40, and since her son is right there. But by this point she starts abandoning tact and starts finding all these excuses to touch me as we keep conversing. And then out of nowhere she touches my right cheek with her hand and says, “You are REALLY cute”.
My roommate, who had kind of been competing for her attention, gets the message and announces he is heading back to the apartment. I tell him I will stay, and give her a sultry look. Once he leaves, I have her sit next to me, and we start touching each other, mostly under the water. I do this as I am making conversation with her son. I nonchalantly talk to him about his school and I slide my hand down her back to her ass, which elicits an expression of shock and excitement from her. She starts overtly touching me all over, above and below the water.
Just a little disclaimer before I continue: yes, she had been drinking, but this woman was not that tipsy. We had been talking about fairly involved topics, like certain kinds of surgeries and diseases she had recently had experience with, and even by the point where she started getting pretty handsy with me, she seemed very in control of her capacities. No slurring, no stumbling, no over-expressiveness, no recollecting of her thoughts, etc.
Back to it. With her son RIGHT THERE, I lift her up a bit, and slide my hand past her ass and to her pussy. It is dark out, the light in the hot tub is out (as it has been for months now), and the bubbles are on, so I am confident he won’t be able to tell what I am doing. I rub outside her suit for a bit before moving my hand out from under her. I then go over her leg back to her pussy (she is practically sitting sideways on my lap at this point), and slip under her one piece and start “diddling her skittle”
before outright fingering her.She goes from libidinous to downright ravenous. She seems unaware her son is right there. She is staring hard at me, and with her eyes wide keeps telling me how bad I am, which I either ignore or respond to by giving her an intense look. All this time, I am still making polite conversation with her son, who I can tell is starting to get uncomfortable with how his mother is draped over me (though I doubt he knew what I was doing below the water).
Though somewhat drunk on my own power, I am reminded of a time when I was her son’s age. I was 13, and my parents had decided to go to Old Chicago for dinner. My mom was and still is a very pretty lady, and there was this drunk guy at the restaurant who was captivated by her and kept trying to talk to her and kept making lewd comments at her. Which made me absolutely FURIOUS, to the point where I grabbed the guy by the shirt and threatened him, and my dad had to pin my arm down to deescalate the situation (I honestly think I could have taken this guy even at 13 lol… I was a very big, aggressive 13 year old and champion wrestler, and he was small and drunk). This hot tub situation is fairly different, but makes me very curious what my younger self would think if he were to see me as I now am. I eventually stop fingering her and whisper in her ear to send her son home.
She goes into authoritative parent mode and has her son leave despite his apprehension at leaving her alone with a strange man. The way she goes about this further confirms in my mind that her lust for me is not just the alcohol talking. He finally leaves, though keeps texting her to see if she is ok. I smile at her and tell her he is a good kid, to which she agrees. Not expecting anyone else to surprise us due to the cold, I start touching her all over and hovering near her lips with my own, teasing her. After I start fingering her again I finally break the tension by kissing her, and then start kissing her down her neck and to her tits, which I take out. I kiss and suck her tits while placing her hand down my trunks and fingering her with my other hand (who says guys can’t multitask!). Eventually I take my trunks all the way off and insert myself in her. The water from the hot tub makes this difficult, but I anticipated this and just wanted to break that barrier before inviting her back to my apartment. We do a little bit of awkward thrusting before I pull out and go back to fingering and kissing her, and then put her tits back beneath her suit and put my suit back on. I grab her by the hand and tell her to come on, assuming the sale, and when she asks where we are going I tell her I have a very interesting ceiling I want to show her, which makes her burst out laughing. We dry off, I help her get in the robe she brought with her, and we slowly walk back to my apartment, marveling at the beauty of the light, falling snow and the great, vast night…
Once back, I have her take her boots off and I offer her bourbon, which she happily accepts. My roommate is in the kitchen, and I give him a big smirk which earns an exasperated chuckle from him. I show her around briefly before taking her to my room, and we are all over each other within 20 seconds of banter. The sex is pretty vanilla but still good. I am pleasantly surprised she is still pretty tight despite having had two kids. I am able to make her cum very quickly. Makes sense she’d know her body well enough to easily get into an orgasmic state by this point of her life.
We end up having four 15-30 minute sessions in a variety of positions over the course of the night. She has very nice legs and skin, though is of course not the same as a girl in her twenties. I was half-expecting her to have all these sexual tricks to throw at me, due to her age and experience, but she was extremely submissive and had nothing particularly interesting for me. Oh well, I enjoy taking the full reins. And she is highly orgasmic, cumming hard and repeatedly without me putting in unusual effort. She is even able to cum on command, which I take full advantage of. I make her cum especially hard in cowgirl, manhandling her ass with my hands as I thrust hard up into her, and ordering her to cum for me, then doing it again before she has had much time to recover.
Beyond that, we both drank a LOT of water. We have some deep pillow talk with her draped across my side. She tells me she is a witch (lmao), and that she can tell me a lot about myself and my future, which I entertain, calling myself an “ally to witches” (which is true in spirit; I love pagan art despite probably being a materialist). She tells me a bunch of vague, nice-sounding statements (hello Barnum Effect), though I am into it, and she is actually very good at it. I even attempt to cold read her (I used that exact term which she didn’t bat an eye to, which tells me she is studied). We chat more about astrology, and I share with her my very genuine affinity towards the Moon (which just so happened to be full that night...). After about three hours, I suggest she go home to her kids and help her find all her stuff. Turns out her apartment is virtually right next to mine lol. We passionately kiss goodnight, and I watch her leave in her soft white robe and furry boots.
The next morning I text her saying I had a good time and that I hope she isn’t too sore today. She happily echoes my sentiment back, though later in the day sends me a long text saying how guilty she feels regarding her son, that she was dealing with emotions from a bad breakup (which she alluded to the night before while we were in bed talking), and that what happened can’t happen again. I tell her I understand and ask her if she regrets the night and she tells me she doesn’t and that it was actually quite beautiful, to which I agree. We both send flirty “see you around” texts, and that was that.
…
All in all, was a fascinating and fun experience. I had never been with a woman past 40, and I certainly had never fingered a woman while chatting with her freaking son! She was very hot for her age, though I am plenty content with it just being a one-night thing. And against the odds, I still got laid despite a blizzard!
I have always prided myself on my duality and my extremity. Take my response to that fucktard that was harassing my mom all the way back then. I was ready to break his bones and gauge his eyes, yet out of a righteous sense of protection. Years later, and this time I find myself the threat to a boy’s mother’s virtue before his very eyes (though a VERY welcome one at that). I played a role in corrupting a mother in front of her son, and tantalized and excited her to the point where she threw away her responsibilities for a night to cum her brains out with me. Yet at the same time, I gave this woman a night she sorely needed (pun not intended). I gave her passion and intrigue and spontaneity and warmth, during a time in her life in which she seemed to especially need it. I was a willing subject for her cold reading and wisdom, making her feel powerful to have influence over someone like myself. I gave her son a lesson on the nature of women without showing him too much. And I’m sure I made her feel young again.
How I love being human. How I love seizing my privilege to bask in both light and darkness. I hope to only heighten my virtuosity and depravity, always in balance.
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