THE RISKY VENTURE: A slow burn “almost-cest” story
– This was rushed, but I wanted it out this weekend. So, I apologize in advance for the terrible and rushed editing.
*
You wouldn’t believe how hot and depraved I looked, all covered in cum on his birthday… but, I’m getting ahead of myself. I just wanted you to know where the story ends, because… well, it doesn’t start that way. So, let’s go back to the beginning real quick.
**
My husband was abusive, like, seriously. I won’t go into details, because that is serious mood killer, and this isn’t that kind of story, but the beginning of this story is decidedly darker than the end. The good news? I got up the courage to leave him, and then I did. The bad news? While I may have been a MILF, a hotwife, a swinger, and an all around sex-godess, I wasn’t an earner. When I was married, I wasn’t “allowed” to be. So, after over a decade of marriage that was a mix between delightfully wicked swinger sex, and horrifically violent abuse, I was, “free-ish”.
I was on my own, but I had no money, no college, no work history, rent due, and half the town was working with my ‘good upstanding’ ex to punish his ‘evil, divorcing, whore ex-wife’. I’d traded one hell for another.
But enough about that, let’s move on to what came next. You see, I was a swinger, a kinkster, and a dirty dirty sex freak (with my husband’s permission) while I was married. And among the many things that I WAS allowed to do, was flirt, and play online. So, while I had no friends locally, I had all kinds of virtual lovers who were still on my side. And one that I semi-adored. He was my favorite role-player, and my best virtual lover, and, most importantly, he was a super-nice guy. Sweet, romantic, and just all around wonderful. But he shocked the pants right off of me when, upon hearing about my woes, he asked if he could call me. Then, after we spoke for a bit, he offered to fly me out, halfway across the country, and put me up at his place until I got back on my feet.
It was super romantic… I thought. But things got strange pretty fast. It started at the airport. I landed, and I was picked up, not by my mystery lover of internet fame, but by his driver and ‘house man’. So… yeah. Apparently my rescuer was well-off. I mean, the plane ticket was an amazing gesture. But there is a difference between paying to fly a hot milf out to see you, and having your own personal driver, who is also a live-in servant. And it got stranger still.
It turned out that I had been flown to an airport that was three hours away, on purpose, so that I would have a long car ride to ‘the house’, wherein I could have my new living situation explained to me.
So, I was escorted back to the car but a giant, well muscled driver, only to find a beautiful woman waiting for me in the back-seat. She, she explained, was another servant of ‘the master of the house’, and was generally considered his right-hand in all things. So, nervous was a really good word for where I was at that point. But then… well, the info that they threw at me came so fast, and was so surprising at every turn, I went from on edge, to on the edge of my seat in pretty short order.
For starters, my apex lover from the internet had only been legally an adult for a few years. Also, he was close to a billionaire, he was a self-made one, and he’d started in poverty. But before I could recover from picturing my dashing hero as semi-baby faced, and, you know, fucking RICH, I start getting warned about how if I live in ‘the main house’, I’m going to see and hear some very disturbing things, because ‘the master’ is a man of many fetishes, and he isn’t shy about them in his own damn house.
Well, now I’m intrigued. Telling me your kinky is like telling an arm wrestling champion you’re strong. They thought they were warning me, when really they were challenging my credentials as kink-goddess. So, we got to talking, and, it turned out, they were not kidding when they said that they’d been instructed to be totally open and honest with me. I mean, I could not shock them, and they spoke as easily about hot wax being dripped onto nipples as I imagined they did about finances and stocks (or whatever).
So, in an incredibly refreshing back and forth with (almost) no resistance, I quickly learned that ‘the master of the house’ never did anything sexual with his staff, but that he’d had many lovers. That his biggest kink was such a taboo that he’d never had a girlfriend he trusted with it, and so he really only got his freak on with the occasional prostitute, or 1 night stand from the fet (fetish( community (and that was unsatisfyingly impersonal as identities were often off the table). After awhile, I learned that, ‘the big one’, was a Mom Son fetish. Apparently, my new host was super dominant, EXCEPT… for his biggest fetish. Then, he liked playing it a bit more hands off. After all, who had more authority than MOM? And where he was very possessive in life, when it came to this ultimate authority figure, he wanted to see her be slutty, depraved, wanton, and used. So, one the one hand, he was a powerful figure who enjoyed sex in his natural state, as a dominant male. But on the other hand, his biggest fetish involved finding out his ‘mommy’ was secretly an insatiable slut, and then watching her get group fucked by his school buddies (in role play, not real life of course).
So… Wow. I was moving in with a young, rich, pervert, who needed to know if I wanted my own place to stay while I got back on my feet because he might bring a hooker home and fuck her in the kitchen… while pretending she was his Mom! Now you tell me, ever had a morning start like that? Because, now I had! It was a lot to take in, but, far from scared off, I was FASCINATED. He was living this rich, kinky lifestyle, while keeping his friends, in luxury, and possibly saving my life on the side, just, you know, out of kindness and friendship to someone who was close to a total stranger in many ways. So, for everything they told, I was still full of questions. It was a three hour drive, and I never stopped asking, and, to their credit, they never stopped giving me answers.
By the time my old friend, and new landlord got back from work (it was late), I was settled in my new room, in the main house; and I’d already had a lovely meal provided by the live-in cook. I let one of his servants tell him that I’d decided to stay, that I was cool with everything, and that I was waiting to talk to him in the living room after he’d had some food. So, after he had dinner…
I made sure that he found me wearing a black silk night shirt that did next to nothing to hide my very large braless tits, a pair of sexy panties, and some color matched (but mostly just warm) socks. He saw me, and had a moment of shock, followed by sexual appreciation, a roaming gaze, and then a very ‘male’ smile.
To that, I smiled back, and said, “I hope you don’t mind. But I figured if you are going to be open and sexual, and where it all on your sleeve, then I could to… Can I?”. He nodded, we shared a hug like old friends, and we ended up sitting on the couch, having some drinks and popcorn brought to us, and talking about what movies and shows we liked until we’d landed on a movie to watch. Honestly, it was kind of great. Of course, his eyes constantly drifted down to my tits, and my body, but then, that was exactly why I’d put it on display in the first place. So I just smiled, and we kept it going.
For the movie, we’d agreed on an old favorite of both of ours; specifically so we could talk about it, but also keep talking to each other while it played, without getting mad at one another for other person making us miss something. So, I waited until about 30 minutes in, and then I scooted in close, my top dipping impossibly low and offering up two massive tits, hanging together in a perfect cleavage line with everything but the areola and nipples on display. Then, semi-awkwardly, like I was nervous, I started to ask him my planned questions. I started by asking, if it was okay, while I was staying there, if I kept having sex… with other people.
When he managed to pull his eyes away from my cleavage, he said, of course it was, and tried to reassure me that I was free from control, and totally safe to be myself while I was his guest.
To this, I nodded, but kept going. I asked him if he was sure, and told him that, while I’d learned all about his fetishes on the way over, I needed him to know that I was VERY kinky, and that I when I asked him if I could still have sex in his house, I meant kinky sex, and with multiple partners. To his credit, his smile warmed, and he raised one eyebrow slightly, almost approvingly, before he assured me that, so long as everything was mutual, and his house and its occupants were safe, I could do absolutely anything with absolutely anyone that I wanted.
Then I scooted a little closer, and moved the blanket he was wearing so that it covered both of us. Now, almost on top of him, I put one finger on his chin, and made sure he was looking me in the eye. Then I said, “Are you sure? I mean,” and I bit my lower lip uncertainly for a moment before adding in a low, sultry tone, “even though I’m your Mother?”. Then I placed one delicate hand on his thigh, much too close to his crotch, and slid it upward slightly as I looked him in the eyes again and, with my most tempting red lipstick covering my lips, I continued. “Because I really want us to have this talk, but, I need to know that you’re okay with it before I go any further”. And then, as if to drive home my point, I slid my hand up just a touch further, which put me just a touch away from “accidentally” being in full contact with his erection.
I knew my meaning had no way of getting lost, and there was a heavy pause in the air as he looked from my eyes, to my lips, to my tits, and back to my eyes again, his mind racing with consequences and possibilities. I gave one last, tiny push then, saying, “I want this… do you?”. And after another breath, something in him relaxed, and he let out a breath that he’d been holding for god knows how long before saying “yes”. And when he did, I couldn’t help myself, so I replied with, “Yes…..”, and after a moment his smile while bright and genuine when he got where I was going, and, almost bashfully, finished, “Yes, Mom”.
I let out a breath myself then, and I relaxed in beside him, placed my other hand on his thigh in a more natural pose, and said, “good, because I was worried we couldn’t talk like this sweetie, and I didn’t want to scare you off”.
His assuring reply that I couldn’t scare him was so certain it almost made me quiver inside. This was a man who could order me to kneel, and do so with such certainty, confidence, and authority, that I’d be wet before I hit my knees. But I knew he had another side, a ‘character’ he’d been dying to play, and I was determined to bring that out of him. So we played the game. We sat there, side by side, both in night clothes or pajamas that did little to conceal, ‘the goods’; and we had a heart to heart as Mother and Son while watching a movie.
I started by repeating myself from before, warning him that I was very kinky, and though I’d never let on about it before, I was practically addicted to sex, and the naughtier the better. Then I moved my free hand to his chin again, and once more turned him so he was looking at my face before saying, “I mean it honey. This lips are ADDICTED to Cock, and I need to know that you are okay with that.” To that, he just nodded, and his amazing confidence began to hide behind the facade of a teenager whose Mother was telling him the most wicked and wonderful things. The transformation was amazing, and I was adoring it!
“And those aren’t the only lips that feel that way,” I said slyly, and as I turned slightly to gesture to my pussy under the blanket, I made sure to accidentally brush my hand against his balls when I did. Then, as if I hadn’t noticed the touch, or his moan, I just kept going. “And you are okay with Mommy… uh, satisfying my cravings, even if you are home?” To that he gulped and nodded. “But…” I said, scooting a little closer, and using the motion slip hand up the length of his cock briefly in another accidental touch before settling it back on his thigh. “…if you’re home, you might see it baby. And you’ll DEFINITELY hear it. I mean, your own Mother, moaning, and sucking, and slurping, and getting her pussy filled”, and as I said it, I was breathy, and I may have moaned… just a little. But he didn’t seem to mind.
In fact, when he nodded again, I adopted a mildly surprised look, and asked him, “Honey! Is this, is this making you, you know, Hard?” And before he could answer, I very deliberately slid my hand back up his thigh. I gently cupped his balls, and I pressed my body closer to his, and I slid that hand up along his balls, and then his shaft, and when I got to the head of his cock, I quickly ran it back down and grasped all that hard cock in my hand, saying with an impressed voice, “Oh my god, you ARE hard. Do you… do you WANT to see Mommy that way?”.
And while I waited for his answer, I very slowly, and very gently, stroked up and down on his shaft. And when he told me yes through the wall of sexual pleasure that was making it harder and harder for him to think or speak, I turned up the heat a little more. I leaned into his ear, still stroking, and asked, “What if it was your friends?”.
I smiled when he blurted “what?!?”, but I knew it was in character. I’d learned most of his very specific fantasies earlier, and so I was very confident, when I stopped stroking his cock, sat back on my feet, and said, “Well sweetie, I just want to know how much you’ve thought about this. Because I’d never imagined that you would be okay with this before, but, now that I know that you are not only okay with it, but are INTO it, my head is spinning with the possibilities! I mean, I’m pretty sure you want to see me suck a man’s cock, don’t you?” And when he said Yes, I replied, “Yes…..”, and I smiled when he timidly replied, “Yes Mom”. In fact, I was so pleased with it, that I rewarded him by saying, “Oh sweetie, I know it’s wrong, but it’s hot hearing you say that when we are talking about dirty things.” Then I asked him if he wanted to see his own Mother getting fucked, and he replied, “yes Mom”. So I wrapped it all up. Saying, “So honey, if I want to do it, and you want to see it, what if we, you know, sort of, arranged it… You could bring some friends home from school tomorrow to play video games, and then you could go to the kitchen and leave us alone for a bit… And when you snuck back in later, we could be doing something that you want to see. So, I’ll ask you again, would it be okay if the guys I was getting fucked by, were your friends?”.
And I swear to god, every time I thought his cock couldn’t get harder, his face couldn’t get redder, or that I couldn’t get more turned on by all of it, I was proven wrong on all counts. The blanket bucked where his dick was tenting it, and he confessed that he’d be okay with his friends fucking his Mother while he watched. When he did, I adopted a very confident and pleased look as I leaned back and smiled at him. I simply said, “Wow”, but when I bit my lip this time, I ran my eyes over him in a very unmotherly way, and he made it clear without saying a word that he liked that too. “You are just opening up all kinds of worlds for us baby. I mean, a few hours ago, I was afraid if I said ‘fuck’ in front of you that you might disown me, and now we are talking about you bringing home two friends, TOMORROW, and watching them spit-roast your Mommy. I mean, just WOW. Right?”. He nodded, and I turned, noticed the movie, and said something along the lines of, ‘oh look, the thing where the thing happens is next’, and then I turned, put my hand back on his thigh innocently, and rested my head on his shoulder saying, “I’m so glad we had this talk Son”.
I could almost hear his internal screaming as he was torn between us continuing his fantasy in a very natural way, and him getting to cum. But I just kept playing the game, and soon, he did his best to relax back into it. But, a few minutes later, I accidentally brushed his dick again, and then, as a concerned Mother, I asked him, “Oh my goodness, sweetie, are you still hard from before?”. When he gave me a frustrated ‘no-shit’ look, with a semi-timid “yeah Mom”, I almost laughed and blew the whole thing. But I didn’t, and instead I told him, “Oh babyyyy. I’m so sorry! You must really need release…” Then I paused the movie, stood up, and leaned over, bending until my tits were on glorious display in his face, and I was looking at eyes that were very much not looking back. Then I said, “… I tell you what. Since we are going to be so open, and honest from now on, would it be okay if I, well, you know…” Then I knelt down, and finished, “… ‘took care of you’?”
His response was a charmingly timid ‘yes’. So I played into a bit, asking. “Are you sure it won’t be weird for you, seeing you own Mother’s lips sliding down a cock, and hearing her moan for more?”. For a second, I worried I’d killed him. But he recovered, and assured me that he would be very okay with that. So I smiled for him, and told him to watch closely then, because it wasn’t everyday that a boy got to watch a big, fat, teenaged dick push its way into his Mother’s smile, and certainly had to be even more rare, if the dick was his own.
Then, in what may have been just a little too far, I kneeled in front of him with my luscious red lips, and said, “PTA”, then I turned and looked like I was talking to someone else as I said, “Pick the kids up from soccer”, then I turned back the other way and said, “Bake sale”, and the I turned towards him and said, “Oh! Oh my!”, and then I just smiled, a sweet, happy, Motherly smile… just before I leaned forward, and forced his cock into it. Then I moaned, and slid all that cock into my warm and waiting mouth as he threw his head back and his knees trembled.
I did my best to make it last, but he’d had a lot of build up. Still, I was a woman of exceptional skill in this area, and so I pulled the blanket up over my head, hit play on the movie, and whispered, “Just pretend Mommy’s not here honey, and I’ll take care of everything”. Then I did my best to make the blowjob last so long that heaven and hell became a single, blurred place, where ultimate pleasure stretched on forever, but never climaxed.
I actually felt when I crossed the line. One little suck was slightly longer than it could be, and that was it, he was on the path, and boiling over the edge rapidly. So I figured as long as he was headed that way anyways, I may as well take him all the way. So as he started to build uncontrollably, I through the blanket back, ripped my night shirt so one tit was hanging out, and I begged, BEGGED him, to cum on me. “I’m sorry baby. I know I shouldn’t, but it’s just so FUCKING hot. I want you to cum on me! Can you do that for me baby! PLEASE!?! Will you cum on Mommy’s face. I want to feel it baby! Do it! Cum all over Mommy’s face!” and then he was screaming, and cumming, and I was moaning, and fingering myself, and as he blew the biggest load I’d ever seen in my life all over my face, I legitimately came while screaming to him that his hot load all over his Mother’s face was making her cum!
Suffice to say, we had a pretty good time my first night there. When it was all over, we were laughing, and panting, and smiling, and just thrilled to fucking death with how the whole thing had played out. We got cleaned up, he frowned after I’d wiped his cum off my face, and I smacked him for it, with a smile. We finished the night as friends, watched the rest of the movie, and one more after it, and then went to bed.
But the next morning, I had his cook make him breakfast, but I brought it to him, and pretended that I, his Mother, had made it for him. I was gentle as a lamb, kissed his forehead, told him he looked handsome, and wished him a great day at school as I saw him off to work that morning. Over time, we figured things out. I was no longer “staying until I got back on my feet”. I’d now been extended the guest for life pass, with full benefits, even if I never did another sexual thing for him again.
But… I eventually revealed to him that we were in a very unique position, because I was just his guest. And I while I liked him as a lover, I’d meant what I said about being kinky and wanting lots of lovers. So, I told him. I was in the odd place of being neither his girlfriend, or his wife. I was just his very free and sexually active house guest, who happened to enjoy playing his Mom from time to time. And that opened a door that someone as possessive and dominant as he was… had long thought would never be open to him, because if I could have lovers, AND play his Mom, then he didn’t have to spend the rest of his life just imagining and role playing what it might be like to see his Mom get fucked…
Oh, you should have seen his face when, after weeks of roleplaying, and using blindfolds and other tricks to simulate his best fantasies, I dropped THAT bombshell. For once, he wasn’t acting when his face went to shock and wonder and awe.
Then I painted two pictures for him. First, I told him to imagine wearing the blindfold again in just a few nights, and role-playing with me that his Mom was getting fucked, but this time, he took the blindfold off, and, there I was. My tits rocking back and forth with his cock directly below them, but this time… this time, there really was a guy fucking me, his Mom, from behind. And this time, when his cock found its way into his Mother’s mouth, he’d feel my body rocking, and feel me moaning, as he really watched a man fuck his Mother from behind right in front him.
The second picture I painted, was of his upcoming birthday. I told him to imagine if we picked up a bunch of people from the fetish community, and threw him a real, fake birthday party where his Mom wore a pretty dress and hosted a party to a large group of his horny, teenage friends. Then I told him, to imagine me being a little too flirty, and a little too sexy, and then, when he blew out the candles, and I asked him what he wanted for his birthday. What if he wanted something terribly wicked, but his Mother reluctantly agreed. And then, what if, just, what if… I told him. What if he got to, in real life, watch a room full of his ‘school buddies’, Gangbang his Mommy…
Well, let me tell you.
You wouldn’t believe how hot and depraved I looked, all covered in cum on his birthday.
***
Now normally, that would be a great way to end the story. Finish strong on my face and my tits! I mean… finish strong by tying the last line to the first, and creating a pretty little cycle. But, why not tell you a little bit more, just this once?
****
So, that was our new life. Most of the time we were amazing friends, who knew one anothers darkest past and most taboo secrets, and totally dug each other anyways. No hiding, no secrets, no shame; and total freedom. We saw movies, played games, played D&D, and just generally had the best life ever. But, over time, my “seductive voice” became his Mom’s normal voice, and so I could change my tone, and bam!, all of a sudden he knew we were role playing. Another trick we used was that he didn’t go be his legal first name, so I could pull that out, or, he would do something and I would turn to him and use his full legal name in a stern little Mom tone, and, once again, he would know that the game was on.
Of course, we also arranged TONS of fantasies. Some were his, and some were mine. At one point, during our D&D campaign, I deliberately made things WAY to sexual, and he (the DM) and I just kept rolling with it until I was the center of a weird half-real life, half-RP gangbang, where I was also his Mom but in a totally different setting. We had some fun by renting out theaters, we had fun in cars, we arranged parties, we had INSANE fun on Halloween and within the fetish, swinger, and kinky sex communities… And well. Eventually, I sort of loved him as a friend, and as a lover, and as a Mom, and, believe or not, he found himself over his hang-ups enough for us to get married.
**** Now, side note. One day, and this is all I’ll say on the matter. My husband and I had a nice long talk about escalation. Escalation, is when you go from 1 on 1 sex, to 1 on 3 sex, and all of a sudden, it is hard to get off to just 1 on 1 sex anymore. So, what do you do when you jump in head first like we did? To this, I assured him, we would have no problems. Because we were both very clever, and very open, and there would always be room for, just one step hotter.
But he was worried. And so, we had a rather infamous conversation that went a little something like this….
He remarked how the line “they gangbanged your Mommy”, was his ultimate. If I was jerking him off and telling him a naughty story about my adventures as his Mom, that that line was GOING to make him cum. And if he started to cum after I said it, and I wanted him to cum hard, I would just moan it again, louder, and make sure my body was pressed into his like I was getting fucked while I jerked him off. So… how do you top that? That was his fear. So I promised him that there was always more, but that I wouldn’t spend my life explaining this, and got 1 example and that was it! He agreed, and the next night I told him I wanted to do it again, just a handjob and a dirty story from Mom, but this time I deliberately rushed it and got to the end much too early. So, I finished the story, wrapped it with his favorite line, but, he wasn’t “there yet”. And so, he asked me if that was all that happened. And when he did, I asked if he mean, did things escalate from there. And he smiled, horney and willing to lend an ear. So, I explained to him that, I THOUGHT that was the end of it. The party was over, his little friends had all cum, and I was about to leave when one of them whispered something in my ear. And, as shocked as I was, I was also curious, so, after a moment, I nodded.
“Then”, I told him, “the boys all cheered and thanked me. And they started to get hard again. So, I got on my hands and knees, and crawled over to the boy whose party it was, and I positioned my tits over his cock.” And as I said, this, I showed my husband what I meant, but getting in a similar position, but also still stroking him. Then I told him to close his eyes (he often did anyways so he could better picture what I was describing), and once he did, I continued. I told him that, “I thought, for sure, they couldn’t do anything more to your Mother than that, I mean… honey, they GANGBANGED me! But, as I was kneeling there, just like this. And all those hard cocks started to gather around me again in anticipation of what was about to happen, well”, and then I yelped like a tongue had just run up my slit. “Well baby, that was when…” and then I half-yelped again, followed by a moan, and long push forward, where I was stroking him with more than just my hand now. Until finally, when I had him on the edge from anticipation alone, I finally told him, “… and that was when they let the dog in”. And then I was simulating hard fucking and moaning as I stroked a massive load out of him.
Now… this story is important for two reasons, one, it settled the topic of escalation once and for all with us, and he never doubted me again. But the second thing was, at breakfast the next morning, out of nowhere, my husband blurts out, “Would you though!? Would you want to? Would you be okay with it!?!” And… I had no idea what he was talking about. But you do, don’t your pervert? ;)
He wanted to know if I had any interest, or willingness to “be with an animal” while he watched. In response to his wording, I joked that he didn’t say dog so, what did he mean, a donkey, a horse… But, he didn’t laugh, and the conversation continued. Now, beyond that, I don’t want to get TOO sidetracked, so, all I’ll say is this… You know how escalation works…
*****
Back from our side note: I was just telling you about how we ACTUALLY got married. It was a surprise that none of us saw coming. But, honestly, I kind of loved it. And, it was different than he’d ever imagined.
He’d gone from someone who would nuke a town where another man once kissed his girlfriend (exaggeration… slightly), to someone who was an open swinger with a long history of the freakiest shit you can imagine. And Married life was even better than when we weren’t married, because wedding rings, wifes, and husbands are hot! Still, time passed, and one day when he was blowing his load inside his Mommy, he made her one. He made ME, one. And that wasn’t even the last time. So, there we were, pretending to be Mom and Son, tying one another down at fet events, and watching one another do hot and nasty things as swingers… but also doing our best to raise healthy and happy kids.
Well… time passed, and kids, I’ll have you know that I aged like I’d been bitten by a vampire. In fact, as my Son’s were approaching legal adulthood, every boy that they knew made it plain as day that I was the hottest milf they’d ever seen. That they were flat out incapable of not getting hard around me, and that only my husband glaring or clearing his throat could get them to tear their eyes away from my cleavage when I dressed a little slutty (and, I kind of always did when they were over).
*****
So, one day, my husband and I are discussing our fantasies while we half masturbate, half get one another off. Just, talking about what does it for us… and I mention that I love that I can not only still make a man who is the same age as my oldest Son, rock-hard, but that they are actually super into my age and my status as a busty, long-haired, Mom (with a perfect ass, of course). And when I do, my husband bucks like I’m talking about his fantasy, and when I push, he confesses that he finds it as hot as I do. So… we talked a little more and came up with some ideas. I mean, by then, all of them knew that we were swingers, and kinksters, and every other naughty little thing. So, I asked, what if I teased them a bit. Maybe told them some true stories? Maybe asked if any of them were planning on going to specific fetish events that we would be at now that they were older? And so, I teased them for months leading up to a big winter event that they were old enough to attend, and now knew how to get access to.
With this as the perfect excuse, my husband and I then told them that we were concerned about just how wild these things got, and that we wanted to make sure that, first of all, they could keep a secret, and second of all, that they could ‘handle’ the kinds of things that would go on there. Especially with us being there, and them all being so close to us and our kids…
So, with that pretty little excuse laid out, we filled our living room with horny, teenager/adults, and spent all night, and I mean, until sunrise all night, telling them true stories about my husband and I. Our role-plays, our fantasies, how we got together (no ugly parts, just naughty stuff), and after each tale, they were rock hard, squirming, and looking like if they didn’t run home and jerk off they’d die. So, I would say so, and offer them the chance to leave, or hear just one more story. And we played that game for damn 12 hours. I actually had them stay for breakfast before they left the next morning.
******
And, how do you think that played out? Do you think that they got to the event, and tried to find a nice girl to hook up with, or that they met up with all their other swinger and fet connections? Or… do you think that they spent the entire time trying to find ways to be naughty with me, specifically?
Yeah. That one.
My husband, who let’s lie and call Mr. Smith, doesn’t have a married name. That isn’t how this works. So me, “Mrs. Smith”, isn’t just what my Son’s friends call me, it’s what his friends called his Real Mom, because that was her real name. So, here we are on our little fetish retreat, and my Son is pretending to be 18, and I am his Mom, Mrs. Smith, and in come 10 strong young 18 year olds, begging to be his ‘friends’, so they can legit fuck their best friends Mom, whom they call Mrs. Smith, and have their whole lives…
Yeah… My husband hadn’t cum 4 times in one night in years, but by god, the first time we did that, he was as turned on as he had ever been in his life. That whole event was insane! 10 horny teenage boys seeking out Momma because they’d fantasized about me since they were 13. And now, they could actually look me in the eyes, call me by my name, and titfuck me while my husband watched approvingly and I asked them sweetly for a nice big load. But, as much as we role-played, and we got up to some crazy fun, my husband had a surprise for me that shocked even me.
See, he invited one of the boys to drive back with us. So, we drove home as husband and wife, and it was a two day trip, and I teased them both, we were just ourselves as I recalled events from the nights before, and made them squirm in their seats for fun and pleasure. But, on the second day, my husband tells me, kind of casually, that the reason he picked this boy, was because of how much he looked like our Son, compared to the others. That… seemed like an odd thing to say. And then, as we’re getting in the car, a voice in the backseat, doing its best impression of my Son, asks, “Hey Mom, can we stop and grab some food from that Italian place near here?”. And for once, it was my turn to be forced into arousal, to blush 10 shades of red, and to have a fantasy that I didn’t know about dropped like a live grenade into my lap. And as I turn to my husband, as red as I’ve ever been, he smiles at me, and says, “Hey Son, did I ever tell you that having a Father and his Son at the same time is one of your Mom’s favorite fantasies to read about online?”. And they just, started fucking role playing it! They talked about it, our ‘Son’ was awkward about it, but they talked about our sex lives that way we had at home with our kids, and it sort of normalized over time, they way it always does in a role-play. And then they were talking about if I’d ever gotten to do it, and when I said no, our Son asked what I HAD done. And… I told him, without any acting needed, that I’d been gangbanged by his 10 best friends. And the truth of it almost made me cum on the spot. But, he wanted to hear more. So, I kept telling him, but now I wasn’t just teasing them, I was teasing me. A lot!
So, we teased the shit out of each other, and then about 20 minutes from our house, we pull into a sleazy hotel parking lot, the two men lead me up to our room with one bed, and just, oh my god. The things we said, always so real for my husband, we so, So, SO REAL for me too all of a sudden. I don’t know if I’d been that turned on before. It was at least a tie! At one point I was standing between them, and I was stroking them both, and my husband asks me where my wedding band is, right at that moment. He tells me to describe to him, what it is doing, and where, and basically makes me say that I’m rubbing it up and down the length of my Son’s big cock! And then they were in my mouth, and then my tits. And then one was licking me, and then I couldn’t even tell who was mauling my breasts but it was making me moan so loud! And after that I hear my husband say that I’ve specifically said that I want to be spit-roasted by a Father/Son team, and the boy in front of me lifts my chin with one gentle hand, looks me in the eyes, and still using that damn familiar voice he says, “Get on your hands and knees Mom. Dad and I are about to make that come true for you”.
I came more times that afternoon than my husband did in the week leading up to it. And when we got home… well, every single day, my panties were soaked. Just, living in my house, going through my daily routine. And our Son’s friends would come over, and they kept the secret like good boys, but, they were ‘on my list now’. And sometimes one of his friends would go to use the bathroom, and we’d sneak into my room, hike my skirt up, and have a hot quickie while his buddies wondered why he was taking so long.
And one day, after my Son’s REAL birthday party, we arranged for an after party, where we, and I’m not even kidding, re-played the party from before, but with my Husband playing my Son, and this time, the party ended when one of boys “learned I was hooker on the side”, and paid me money right then and there to be there whore. In the middle of the party of course, so my Son watched, until he couldn’t take it anymore, dug out his wallet, and also took a crack at his whore Mother.
The games were so risky, and so close to home, and that wasn’t the last time that the boy from the ride home played my Son either… And when my husband asked them if they knew about escalation, and told them about our conversation about the same subject….
Well. I could go on and on and on. And… as for the question you are all asking? As for the one thing I haven’t mentioned yet…
I can’t really answer that. But I will say this. If you were old enough to tag along to a fetish event, and I was your Mom… what would YOU do?
– This was rushed, but I wanted it out this weekend. So, I apologize in advance for the terrible and rushed editing.
*
You wouldn’t believe how hot and depraved I looked, all covered in cum on his birthday… but, I’m getting ahead of myself. I just wanted you to know where the story ends, because… well, it doesn’t start that way. So, let’s go back to the beginning real quick.
**
My husband was abusive, like, seriously. I won’t go into details, because that is serious mood killer, and this isn’t that kind of story, but the beginning of this story is decidedly darker than the end. The good news? I got up the courage to leave him, and then I did. The bad news? While I may have been a MILF, a hotwife, a swinger, and an all around sex-godess, I wasn’t an earner. When I was married, I wasn’t “allowed” to be. So, after over a decade of marriage that was a mix between delightfully wicked swinger sex, and horrifically violent abuse, I was, “free-ish”.
I was on my own, but I had no money, no college, no work history, rent due, and half the town was working with my ‘good upstanding’ ex to punish his ‘evil, divorcing, whore ex-wife’. I’d traded one hell for another.
But enough about that, let’s move on to what came next. You see, I was a swinger, a kinkster, and a dirty dirty sex freak (with my husband’s permission) while I was married. And among the many things that I WAS allowed to do, was flirt, and play online. So, while I had no friends locally, I had all kinds of virtual lovers who were still on my side. And one that I semi-adored. He was my favorite role-player, and my best virtual lover, and, most importantly, he was a super-nice guy. Sweet, romantic, and just all around wonderful. But he shocked the pants right off of me when, upon hearing about my woes, he asked if he could call me. Then, after we spoke for a bit, he offered to fly me out, halfway across the country, and put me up at his place until I got back on my feet.
It was super romantic… I thought. But things got strange pretty fast. It started at the airport. I landed, and I was picked up, not by my mystery lover of internet fame, but by his driver and ‘house man’. So… yeah. Apparently my rescuer was well-off. I mean, the plane ticket was an amazing gesture. But there is a difference between paying to fly a hot milf out to see you, and having your own personal driver, who is also a live-in servant. And it got stranger still.
It turned out that I had been flown to an airport that was three hours away, on purpose, so that I would have a long car ride to ‘the house’, wherein I could have my new living situation explained to me.
So, I was escorted back to the car but a giant, well muscled driver, only to find a beautiful woman waiting for me in the back-seat. She, she explained, was another servant of ‘the master of the house’, and was generally considered his right-hand in all things. So, nervous was a really good word for where I was at that point. But then… well, the info that they threw at me came so fast, and was so surprising at every turn, I went from on edge, to on the edge of my seat in pretty short order.
For starters, my apex lover from the internet had only been legally an adult for a few years. Also, he was close to a billionaire, he was a self-made one, and he’d started in poverty. But before I could recover from picturing my dashing hero as semi-baby faced, and, you know, fucking RICH, I start getting warned about how if I live in ‘the main house’, I’m going to see and hear some very disturbing things, because ‘the master’ is a man of many fetishes, and he isn’t shy about them in his own damn house.
Well, now I’m intrigued. Telling me your kinky is like telling an arm wrestling champion you’re strong. They thought they were warning me, when really they were challenging my credentials as kink-goddess. So, we got to talking, and, it turned out, they were not kidding when they said that they’d been instructed to be totally open and honest with me. I mean, I could not shock them, and they spoke as easily about hot wax being dripped onto nipples as I imagined they did about finances and stocks (or whatever).
So, in an incredibly refreshing back and forth with (almost) no resistance, I quickly learned that ‘the master of the house’ never did anything sexual with his staff, but that he’d had many lovers. That his biggest kink was such a taboo that he’d never had a girlfriend he trusted with it, and so he really only got his freak on with the occasional prostitute, or 1 night stand from the fet (fetish( community (and that was unsatisfyingly impersonal as identities were often off the table). After awhile, I learned that, ‘the big one’, was a Mom Son fetish. Apparently, my new host was super dominant, EXCEPT… for his biggest fetish. Then, he liked playing it a bit more hands off. After all, who had more authority than MOM? And where he was very possessive in life, when it came to this ultimate authority figure, he wanted to see her be slutty, depraved, wanton, and used. So, one the one hand, he was a powerful figure who enjoyed sex in his natural state, as a dominant male. But on the other hand, his biggest fetish involved finding out his ‘mommy’ was secretly an insatiable slut, and then watching her get group fucked by his school buddies (in role play, not real life of course).
So… Wow. I was moving in with a young, rich, pervert, who needed to know if I wanted my own place to stay while I got back on my feet because he might bring a hooker home and fuck her in the kitchen… while pretending she was his Mom! Now you tell me, ever had a morning start like that? Because, now I had! It was a lot to take in, but, far from scared off, I was FASCINATED. He was living this rich, kinky lifestyle, while keeping his friends, in luxury, and possibly saving my life on the side, just, you know, out of kindness and friendship to someone who was close to a total stranger in many ways. So, for everything they told, I was still full of questions. It was a three hour drive, and I never stopped asking, and, to their credit, they never stopped giving me answers.
By the time my old friend, and new landlord got back from work (it was late), I was settled in my new room, in the main house; and I’d already had a lovely meal provided by the live-in cook. I let one of his servants tell him that I’d decided to stay, that I was cool with everything, and that I was waiting to talk to him in the living room after he’d had some food. So, after he had dinner…
I made sure that he found me wearing a black silk night shirt that did next to nothing to hide my very large braless tits, a pair of sexy panties, and some color matched (but mostly just warm) socks. He saw me, and had a moment of shock, followed by sexual appreciation, a roaming gaze, and then a very ‘male’ smile.
To that, I smiled back, and said, “I hope you don’t mind. But I figured if you are going to be open and sexual, and where it all on your sleeve, then I could to… Can I?”. He nodded, we shared a hug like old friends, and we ended up sitting on the couch, having some drinks and popcorn brought to us, and talking about what movies and shows we liked until we’d landed on a movie to watch. Honestly, it was kind of great. Of course, his eyes constantly drifted down to my tits, and my body, but then, that was exactly why I’d put it on display in the first place. So I just smiled, and we kept it going.
For the movie, we’d agreed on an old favorite of both of ours; specifically so we could talk about it, but also keep talking to each other while it played, without getting mad at one another for other person making us miss something. So, I waited until about 30 minutes in, and then I scooted in close, my top dipping impossibly low and offering up two massive tits, hanging together in a perfect cleavage line with everything but the areola and nipples on display. Then, semi-awkwardly, like I was nervous, I started to ask him my planned questions. I started by asking, if it was okay, while I was staying there, if I kept having sex… with other people.
When he managed to pull his eyes away from my cleavage, he said, of course it was, and tried to reassure me that I was free from control, and totally safe to be myself while I was his guest.
To this, I nodded, but kept going. I asked him if he was sure, and told him that, while I’d learned all about his fetishes on the way over, I needed him to know that I was VERY kinky, and that I when I asked him if I could still have sex in his house, I meant kinky sex, and with multiple partners. To his credit, his smile warmed, and he raised one eyebrow slightly, almost approvingly, before he assured me that, so long as everything was mutual, and his house and its occupants were safe, I could do absolutely anything with absolutely anyone that I wanted.
Then I scooted a little closer, and moved the blanket he was wearing so that it covered both of us. Now, almost on top of him, I put one finger on his chin, and made sure he was looking me in the eye. Then I said, “Are you sure? I mean,” and I bit my lower lip uncertainly for a moment before adding in a low, sultry tone, “even though I’m your Mother?”. Then I placed one delicate hand on his thigh, much too close to his crotch, and slid it upward slightly as I looked him in the eyes again and, with my most tempting red lipstick covering my lips, I continued. “Because I really want us to have this talk, but, I need to know that you’re okay with it before I go any further”. And then, as if to drive home my point, I slid my hand up just a touch further, which put me just a touch away from “accidentally” being in full contact with his erection.
I knew my meaning had no way of getting lost, and there was a heavy pause in the air as he looked from my eyes, to my lips, to my tits, and back to my eyes again, his mind racing with consequences and possibilities. I gave one last, tiny push then, saying, “I want this… do you?”. And after another breath, something in him relaxed, and he let out a breath that he’d been holding for god knows how long before saying “yes”. And when he did, I couldn’t help myself, so I replied with, “Yes…..”, and after a moment his smile while bright and genuine when he got where I was going, and, almost bashfully, finished, “Yes, Mom”.
I let out a breath myself then, and I relaxed in beside him, placed my other hand on his thigh in a more natural pose, and said, “good, because I was worried we couldn’t talk like this sweetie, and I didn’t want to scare you off”.
His assuring reply that I couldn’t scare him was so certain it almost made me quiver inside. This was a man who could order me to kneel, and do so with such certainty, confidence, and authority, that I’d be wet before I hit my knees. But I knew he had another side, a ‘character’ he’d been dying to play, and I was determined to bring that out of him. So we played the game. We sat there, side by side, both in night clothes or pajamas that did little to conceal, ‘the goods’; and we had a heart to heart as Mother and Son while watching a movie.
I started by repeating myself from before, warning him that I was very kinky, and though I’d never let on about it before, I was practically addicted to sex, and the naughtier the better. Then I moved my free hand to his chin again, and once more turned him so he was looking at my face before saying, “I mean it honey. This lips are ADDICTED to Cock, and I need to know that you are okay with that.” To that, he just nodded, and his amazing confidence began to hide behind the facade of a teenager whose Mother was telling him the most wicked and wonderful things. The transformation was amazing, and I was adoring it!
“And those aren’t the only lips that feel that way,” I said slyly, and as I turned slightly to gesture to my pussy under the blanket, I made sure to accidentally brush my hand against his balls when I did. Then, as if I hadn’t noticed the touch, or his moan, I just kept going. “And you are okay with Mommy… uh, satisfying my cravings, even if you are home?” To that he gulped and nodded. “But…” I said, scooting a little closer, and using the motion slip hand up the length of his cock briefly in another accidental touch before settling it back on his thigh. “…if you’re home, you might see it baby. And you’ll DEFINITELY hear it. I mean, your own Mother, moaning, and sucking, and slurping, and getting her pussy filled”, and as I said it, I was breathy, and I may have moaned… just a little. But he didn’t seem to mind.
In fact, when he nodded again, I adopted a mildly surprised look, and asked him, “Honey! Is this, is this making you, you know, Hard?” And before he could answer, I very deliberately slid my hand back up his thigh. I gently cupped his balls, and I pressed my body closer to his, and I slid that hand up along his balls, and then his shaft, and when I got to the head of his cock, I quickly ran it back down and grasped all that hard cock in my hand, saying with an impressed voice, “Oh my god, you ARE hard. Do you… do you WANT to see Mommy that way?”.
And while I waited for his answer, I very slowly, and very gently, stroked up and down on his shaft. And when he told me yes through the wall of sexual pleasure that was making it harder and harder for him to think or speak, I turned up the heat a little more. I leaned into his ear, still stroking, and asked, “What if it was your friends?”.
I smiled when he blurted “what?!?”, but I knew it was in character. I’d learned most of his very specific fantasies earlier, and so I was very confident, when I stopped stroking his cock, sat back on my feet, and said, “Well sweetie, I just want to know how much you’ve thought about this. Because I’d never imagined that you would be okay with this before, but, now that I know that you are not only okay with it, but are INTO it, my head is spinning with the possibilities! I mean, I’m pretty sure you want to see me suck a man’s cock, don’t you?” And when he said Yes, I replied, “Yes…..”, and I smiled when he timidly replied, “Yes Mom”. In fact, I was so pleased with it, that I rewarded him by saying, “Oh sweetie, I know it’s wrong, but it’s hot hearing you say that when we are talking about dirty things.” Then I asked him if he wanted to see his own Mother getting fucked, and he replied, “yes Mom”. So I wrapped it all up. Saying, “So honey, if I want to do it, and you want to see it, what if we, you know, sort of, arranged it… You could bring some friends home from school tomorrow to play video games, and then you could go to the kitchen and leave us alone for a bit… And when you snuck back in later, we could be doing something that you want to see. So, I’ll ask you again, would it be okay if the guys I was getting fucked by, were your friends?”.
And I swear to god, every time I thought his cock couldn’t get harder, his face couldn’t get redder, or that I couldn’t get more turned on by all of it, I was proven wrong on all counts. The blanket bucked where his dick was tenting it, and he confessed that he’d be okay with his friends fucking his Mother while he watched. When he did, I adopted a very confident and pleased look as I leaned back and smiled at him. I simply said, “Wow”, but when I bit my lip this time, I ran my eyes over him in a very unmotherly way, and he made it clear without saying a word that he liked that too. “You are just opening up all kinds of worlds for us baby. I mean, a few hours ago, I was afraid if I said ‘fuck’ in front of you that you might disown me, and now we are talking about you bringing home two friends, TOMORROW, and watching them spit-roast your Mommy. I mean, just WOW. Right?”. He nodded, and I turned, noticed the movie, and said something along the lines of, ‘oh look, the thing where the thing happens is next’, and then I turned, put my hand back on his thigh innocently, and rested my head on his shoulder saying, “I’m so glad we had this talk Son”.
I could almost hear his internal screaming as he was torn between us continuing his fantasy in a very natural way, and him getting to cum. But I just kept playing the game, and soon, he did his best to relax back into it. But, a few minutes later, I accidentally brushed his dick again, and then, as a concerned Mother, I asked him, “Oh my goodness, sweetie, are you still hard from before?”. When he gave me a frustrated ‘no-shit’ look, with a semi-timid “yeah Mom”, I almost laughed and blew the whole thing. But I didn’t, and instead I told him, “Oh babyyyy. I’m so sorry! You must really need release…” Then I paused the movie, stood up, and leaned over, bending until my tits were on glorious display in his face, and I was looking at eyes that were very much not looking back. Then I said, “… I tell you what. Since we are going to be so open, and honest from now on, would it be okay if I, well, you know…” Then I knelt down, and finished, “… ‘took care of you’?”
His response was a charmingly timid ‘yes’. So I played into a bit, asking. “Are you sure it won’t be weird for you, seeing you own Mother’s lips sliding down a cock, and hearing her moan for more?”. For a second, I worried I’d killed him. But he recovered, and assured me that he would be very okay with that. So I smiled for him, and told him to watch closely then, because it wasn’t everyday that a boy got to watch a big, fat, teenaged dick push its way into his Mother’s smile, and certainly had to be even more rare, if the dick was his own.
Then, in what may have been just a little too far, I kneeled in front of him with my luscious red lips, and said, “PTA”, then I turned and looked like I was talking to someone else as I said, “Pick the kids up from soccer”, then I turned back the other way and said, “Bake sale”, and the I turned towards him and said, “Oh! Oh my!”, and then I just smiled, a sweet, happy, Motherly smile… just before I leaned forward, and forced his cock into it. Then I moaned, and slid all that cock into my warm and waiting mouth as he threw his head back and his knees trembled.
I did my best to make it last, but he’d had a lot of build up. Still, I was a woman of exceptional skill in this area, and so I pulled the blanket up over my head, hit play on the movie, and whispered, “Just pretend Mommy’s not here honey, and I’ll take care of everything”. Then I did my best to make the blowjob last so long that heaven and hell became a single, blurred place, where ultimate pleasure stretched on forever, but never climaxed.
I actually felt when I crossed the line. One little suck was slightly longer than it could be, and that was it, he was on the path, and boiling over the edge rapidly. So I figured as long as he was headed that way anyways, I may as well take him all the way. So as he started to build uncontrollably, I through the blanket back, ripped my night shirt so one tit was hanging out, and I begged, BEGGED him, to cum on me. “I’m sorry baby. I know I shouldn’t, but it’s just so FUCKING hot. I want you to cum on me! Can you do that for me baby! PLEASE!?! Will you cum on Mommy’s face. I want to feel it baby! Do it! Cum all over Mommy’s face!” and then he was screaming, and cumming, and I was moaning, and fingering myself, and as he blew the biggest load I’d ever seen in my life all over my face, I legitimately came while screaming to him that his hot load all over his Mother’s face was making her cum!
Suffice to say, we had a pretty good time my first night there. When it was all over, we were laughing, and panting, and smiling, and just thrilled to fucking death with how the whole thing had played out. We got cleaned up, he frowned after I’d wiped his cum off my face, and I smacked him for it, with a smile. We finished the night as friends, watched the rest of the movie, and one more after it, and then went to bed.
But the next morning, I had his cook make him breakfast, but I brought it to him, and pretended that I, his Mother, had made it for him. I was gentle as a lamb, kissed his forehead, told him he looked handsome, and wished him a great day at school as I saw him off to work that morning. Over time, we figured things out. I was no longer “staying until I got back on my feet”. I’d now been extended the guest for life pass, with full benefits, even if I never did another sexual thing for him again.
But… I eventually revealed to him that we were in a very unique position, because I was just his guest. And I while I liked him as a lover, I’d meant what I said about being kinky and wanting lots of lovers. So, I told him. I was in the odd place of being neither his girlfriend, or his wife. I was just his very free and sexually active house guest, who happened to enjoy playing his Mom from time to time. And that opened a door that someone as possessive and dominant as he was… had long thought would never be open to him, because if I could have lovers, AND play his Mom, then he didn’t have to spend the rest of his life just imagining and role playing what it might be like to see his Mom get fucked…
Oh, you should have seen his face when, after weeks of roleplaying, and using blindfolds and other tricks to simulate his best fantasies, I dropped THAT bombshell. For once, he wasn’t acting when his face went to shock and wonder and awe.
Then I painted two pictures for him. First, I told him to imagine wearing the blindfold again in just a few nights, and role-playing with me that his Mom was getting fucked, but this time, he took the blindfold off, and, there I was. My tits rocking back and forth with his cock directly below them, but this time… this time, there really was a guy fucking me, his Mom, from behind. And this time, when his cock found its way into his Mother’s mouth, he’d feel my body rocking, and feel me moaning, as he really watched a man fuck his Mother from behind right in front him.
The second picture I painted, was of his upcoming birthday. I told him to imagine if we picked up a bunch of people from the fetish community, and threw him a real, fake birthday party where his Mom wore a pretty dress and hosted a party to a large group of his horny, teenage friends. Then I told him, to imagine me being a little too flirty, and a little too sexy, and then, when he blew out the candles, and I asked him what he wanted for his birthday. What if he wanted something terribly wicked, but his Mother reluctantly agreed. And then, what if, just, what if… I told him. What if he got to, in real life, watch a room full of his ‘school buddies’, Gangbang his Mommy…
Well, let me tell you.
You wouldn’t believe how hot and depraved I looked, all covered in cum on his birthday.
***
Now normally, that would be a great way to end the story. Finish strong on my face and my tits! I mean… finish strong by tying the last line to the first, and creating a pretty little cycle. But, why not tell you a little bit more, just this once?
****
So, that was our new life. Most of the time we were amazing friends, who knew one anothers darkest past and most taboo secrets, and totally dug each other anyways. No hiding, no secrets, no shame; and total freedom. We saw movies, played games, played D&D, and just generally had the best life ever. But, over time, my “seductive voice” became his Mom’s normal voice, and so I could change my tone, and bam!, all of a sudden he knew we were role playing. Another trick we used was that he didn’t go be his legal first name, so I could pull that out, or, he would do something and I would turn to him and use his full legal name in a stern little Mom tone, and, once again, he would know that the game was on.
Of course, we also arranged TONS of fantasies. Some were his, and some were mine. At one point, during our D&D campaign, I deliberately made things WAY to sexual, and he (the DM) and I just kept rolling with it until I was the center of a weird half-real life, half-RP gangbang, where I was also his Mom but in a totally different setting. We had some fun by renting out theaters, we had fun in cars, we arranged parties, we had INSANE fun on Halloween and within the fetish, swinger, and kinky sex communities… And well. Eventually, I sort of loved him as a friend, and as a lover, and as a Mom, and, believe or not, he found himself over his hang-ups enough for us to get married.
**** Now, side note. One day, and this is all I’ll say on the matter. My husband and I had a nice long talk about escalation. Escalation, is when you go from 1 on 1 sex, to 1 on 3 sex, and all of a sudden, it is hard to get off to just 1 on 1 sex anymore. So, what do you do when you jump in head first like we did? To this, I assured him, we would have no problems. Because we were both very clever, and very open, and there would always be room for, just one step hotter.
But he was worried. And so, we had a rather infamous conversation that went a little something like this….
He remarked how the line “they gangbanged your Mommy”, was his ultimate. If I was jerking him off and telling him a naughty story about my adventures as his Mom, that that line was GOING to make him cum. And if he started to cum after I said it, and I wanted him to cum hard, I would just moan it again, louder, and make sure my body was pressed into his like I was getting fucked while I jerked him off. So… how do you top that? That was his fear. So I promised him that there was always more, but that I wouldn’t spend my life explaining this, and got 1 example and that was it! He agreed, and the next night I told him I wanted to do it again, just a handjob and a dirty story from Mom, but this time I deliberately rushed it and got to the end much too early. So, I finished the story, wrapped it with his favorite line, but, he wasn’t “there yet”. And so, he asked me if that was all that happened. And when he did, I asked if he mean, did things escalate from there. And he smiled, horney and willing to lend an ear. So, I explained to him that, I THOUGHT that was the end of it. The party was over, his little friends had all cum, and I was about to leave when one of them whispered something in my ear. And, as shocked as I was, I was also curious, so, after a moment, I nodded.
“Then”, I told him, “the boys all cheered and thanked me. And they started to get hard again. So, I got on my hands and knees, and crawled over to the boy whose party it was, and I positioned my tits over his cock.” And as I said, this, I showed my husband what I meant, but getting in a similar position, but also still stroking him. Then I told him to close his eyes (he often did anyways so he could better picture what I was describing), and once he did, I continued. I told him that, “I thought, for sure, they couldn’t do anything more to your Mother than that, I mean… honey, they GANGBANGED me! But, as I was kneeling there, just like this. And all those hard cocks started to gather around me again in anticipation of what was about to happen, well”, and then I yelped like a tongue had just run up my slit. “Well baby, that was when…” and then I half-yelped again, followed by a moan, and long push forward, where I was stroking him with more than just my hand now. Until finally, when I had him on the edge from anticipation alone, I finally told him, “… and that was when they let the dog in”. And then I was simulating hard fucking and moaning as I stroked a massive load out of him.
Now… this story is important for two reasons, one, it settled the topic of escalation once and for all with us, and he never doubted me again. But the second thing was, at breakfast the next morning, out of nowhere, my husband blurts out, “Would you though!? Would you want to? Would you be okay with it!?!” And… I had no idea what he was talking about. But you do, don’t your pervert? ;)
He wanted to know if I had any interest, or willingness to “be with an animal” while he watched. In response to his wording, I joked that he didn’t say dog so, what did he mean, a donkey, a horse… But, he didn’t laugh, and the conversation continued. Now, beyond that, I don’t want to get TOO sidetracked, so, all I’ll say is this… You know how escalation works…
*****
Back from our side note: I was just telling you about how we ACTUALLY got married. It was a surprise that none of us saw coming. But, honestly, I kind of loved it. And, it was different than he’d ever imagined.
He’d gone from someone who would nuke a town where another man once kissed his girlfriend (exaggeration… slightly), to someone who was an open swinger with a long history of the freakiest shit you can imagine. And Married life was even better than when we weren’t married, because wedding rings, wifes, and husbands are hot! Still, time passed, and one day when he was blowing his load inside his Mommy, he made her one. He made ME, one. And that wasn’t even the last time. So, there we were, pretending to be Mom and Son, tying one another down at fet events, and watching one another do hot and nasty things as swingers… but also doing our best to raise healthy and happy kids.
Well… time passed, and kids, I’ll have you know that I aged like I’d been bitten by a vampire. In fact, as my Son’s were approaching legal adulthood, every boy that they knew made it plain as day that I was the hottest milf they’d ever seen. That they were flat out incapable of not getting hard around me, and that only my husband glaring or clearing his throat could get them to tear their eyes away from my cleavage when I dressed a little slutty (and, I kind of always did when they were over).
*****
So, one day, my husband and I are discussing our fantasies while we half masturbate, half get one another off. Just, talking about what does it for us… and I mention that I love that I can not only still make a man who is the same age as my oldest Son, rock-hard, but that they are actually super into my age and my status as a busty, long-haired, Mom (with a perfect ass, of course). And when I do, my husband bucks like I’m talking about his fantasy, and when I push, he confesses that he finds it as hot as I do. So… we talked a little more and came up with some ideas. I mean, by then, all of them knew that we were swingers, and kinksters, and every other naughty little thing. So, I asked, what if I teased them a bit. Maybe told them some true stories? Maybe asked if any of them were planning on going to specific fetish events that we would be at now that they were older? And so, I teased them for months leading up to a big winter event that they were old enough to attend, and now knew how to get access to.
With this as the perfect excuse, my husband and I then told them that we were concerned about just how wild these things got, and that we wanted to make sure that, first of all, they could keep a secret, and second of all, that they could ‘handle’ the kinds of things that would go on there. Especially with us being there, and them all being so close to us and our kids…
So, with that pretty little excuse laid out, we filled our living room with horny, teenager/adults, and spent all night, and I mean, until sunrise all night, telling them true stories about my husband and I. Our role-plays, our fantasies, how we got together (no ugly parts, just naughty stuff), and after each tale, they were rock hard, squirming, and looking like if they didn’t run home and jerk off they’d die. So, I would say so, and offer them the chance to leave, or hear just one more story. And we played that game for damn 12 hours. I actually had them stay for breakfast before they left the next morning.
******
And, how do you think that played out? Do you think that they got to the event, and tried to find a nice girl to hook up with, or that they met up with all their other swinger and fet connections? Or… do you think that they spent the entire time trying to find ways to be naughty with me, specifically?
Yeah. That one.
My husband, who let’s lie and call Mr. Smith, doesn’t have a married name. That isn’t how this works. So me, “Mrs. Smith”, isn’t just what my Son’s friends call me, it’s what his friends called his Real Mom, because that was her real name. So, here we are on our little fetish retreat, and my Son is pretending to be 18, and I am his Mom, Mrs. Smith, and in come 10 strong young 18 year olds, begging to be his ‘friends’, so they can legit fuck their best friends Mom, whom they call Mrs. Smith, and have their whole lives…
Yeah… My husband hadn’t cum 4 times in one night in years, but by god, the first time we did that, he was as turned on as he had ever been in his life. That whole event was insane! 10 horny teenage boys seeking out Momma because they’d fantasized about me since they were 13. And now, they could actually look me in the eyes, call me by my name, and titfuck me while my husband watched approvingly and I asked them sweetly for a nice big load. But, as much as we role-played, and we got up to some crazy fun, my husband had a surprise for me that shocked even me.
See, he invited one of the boys to drive back with us. So, we drove home as husband and wife, and it was a two day trip, and I teased them both, we were just ourselves as I recalled events from the nights before, and made them squirm in their seats for fun and pleasure. But, on the second day, my husband tells me, kind of casually, that the reason he picked this boy, was because of how much he looked like our Son, compared to the others. That… seemed like an odd thing to say. And then, as we’re getting in the car, a voice in the backseat, doing its best impression of my Son, asks, “Hey Mom, can we stop and grab some food from that Italian place near here?”. And for once, it was my turn to be forced into arousal, to blush 10 shades of red, and to have a fantasy that I didn’t know about dropped like a live grenade into my lap. And as I turn to my husband, as red as I’ve ever been, he smiles at me, and says, “Hey Son, did I ever tell you that having a Father and his Son at the same time is one of your Mom’s favorite fantasies to read about online?”. And they just, started fucking role playing it! They talked about it, our ‘Son’ was awkward about it, but they talked about our sex lives that way we had at home with our kids, and it sort of normalized over time, they way it always does in a role-play. And then they were talking about if I’d ever gotten to do it, and when I said no, our Son asked what I HAD done. And… I told him, without any acting needed, that I’d been gangbanged by his 10 best friends. And the truth of it almost made me cum on the spot. But, he wanted to hear more. So, I kept telling him, but now I wasn’t just teasing them, I was teasing me. A lot!
So, we teased the shit out of each other, and then about 20 minutes from our house, we pull into a sleazy hotel parking lot, the two men lead me up to our room with one bed, and just, oh my god. The things we said, always so real for my husband, we so, So, SO REAL for me too all of a sudden. I don’t know if I’d been that turned on before. It was at least a tie! At one point I was standing between them, and I was stroking them both, and my husband asks me where my wedding band is, right at that moment. He tells me to describe to him, what it is doing, and where, and basically makes me say that I’m rubbing it up and down the length of my Son’s big cock! And then they were in my mouth, and then my tits. And then one was licking me, and then I couldn’t even tell who was mauling my breasts but it was making me moan so loud! And after that I hear my husband say that I’ve specifically said that I want to be spit-roasted by a Father/Son team, and the boy in front of me lifts my chin with one gentle hand, looks me in the eyes, and still using that damn familiar voice he says, “Get on your hands and knees Mom. Dad and I are about to make that come true for you”.
I came more times that afternoon than my husband did in the week leading up to it. And when we got home… well, every single day, my panties were soaked. Just, living in my house, going through my daily routine. And our Son’s friends would come over, and they kept the secret like good boys, but, they were ‘on my list now’. And sometimes one of his friends would go to use the bathroom, and we’d sneak into my room, hike my skirt up, and have a hot quickie while his buddies wondered why he was taking so long.
And one day, after my Son’s REAL birthday party, we arranged for an after party, where we, and I’m not even kidding, re-played the party from before, but with my Husband playing my Son, and this time, the party ended when one of boys “learned I was hooker on the side”, and paid me money right then and there to be there whore. In the middle of the party of course, so my Son watched, until he couldn’t take it anymore, dug out his wallet, and also took a crack at his whore Mother.
The games were so risky, and so close to home, and that wasn’t the last time that the boy from the ride home played my Son either… And when my husband asked them if they knew about escalation, and told them about our conversation about the same subject….
Well. I could go on and on and on. And… as for the question you are all asking? As for the one thing I haven’t mentioned yet…
I can’t really answer that. But I will say this. If you were old enough to tag along to a fetish event, and I was your Mom… what would YOU do?
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