Author's Note: All characters in this story at are least 18 years of age, and, even in role play, are "playing" characters at least 18 years of age.
***
The arrangement was as simple as a complicated thing could be...
My parents had been swingers since forever. But not just sharing, the whole nine yards. They were into all kinds of kink. They went to clubs, events, and parties that my highschool buddies thought that they'd made up in their heads, but, you know, the REAL ones.
It was weird for me at first... but in time I got used to it, and, eventually, I even worked up the courage to ask about it. I mean, on the one hand, it was my parents, and ew. I have no desire to picture my dad having sex. But on the other hand, they legitimately did the things that most people barely had the courage to fantasize about, and if there is one thing a teenager (18 going on 19) can appreciate, it's dirty, kinky, (great to masturbate to) and adventurous sex. So, yeah... I had questions.
Now, on the plus side, my parents were cool about it... sort of. My Dad seemed to like telling me about stuff that he didn't think I'd ever get to experience. It was like bragging for him, in a contest he figured he could never lose. Still, even if he told me because he was trying to be an asshole, he still told me, and I REALLY wanted to know.
As for Mom, she was super cool about it. At first, it was all about honesty. As long I was was talking to her, being honest with her, and having these talks with her, then she figured I deserved the info.
It was good for us bonding wise, and she got to keep bullshit information, regarding sex, away from her Son. At first... But, I could swear that, over time, Mom really seemed to like flirting with me. Like... "LIKE", liked. Which, as realizations go, should have been gross, but instead it was a lot of other things. Hot... crazy, stunning, kinda fun, hot again... I know I should have been grossed out, but my Mom was a sweet, kind, fun woman, with a great laugh and a delightful personality. Also... she had long hair, big tits, beautiful eyes, and an ass that could stop traffic and may have actually caused a car accident one time...
So, yeah. Sort of a mixed bag. But a fun one. It was always a bit of an adventure asking my Mom a sex question. I would brace myself, and find out about all this hot stuff, and then she would smile, lean in, and whisper something like, "at least that was what it was like when I did it". And we both knew, that she knew, that she was driving me crazy (in a good way) when she did stuff like that. Then she'd just lean back, glance down at the outline of an erection I had no chance of hiding, and wink at me. Mom had a very sexy smile when she wanted, and in those moments, she always "wanted". It never went further than that of course, but it was very hot, kind of fun, and, all things considered, pretty damn flirty.
And that brings us to the night that things went past "flirty". You see, Mom and Dad went to a lot of sex and fetish clubs. Not just the kind with music and dancing, but also straight up fetish clubs, with memberships. Places that were just decked out "dungeons". Big open rooms with privacy from the outside world, and no privacy from the other members.
These were places for a person to be tied up and whipped, put on a cross and spanked, or tied to a table and "tortured" until they had to use a safe word to make the orgasms stop. For some it was a complicated affair involving tool kits, and for others it was just about giving a stranger head, or getting fucked in a place where people could see you, but no one would arrest you or otherwise fuck-up your "normal life"... just because you wanted to cum in a very specific way.
So, anyway, Mom and Dad were supposed to go to a new club; one that was a couple of hours away. They were going to meet a mutual friend, have some fun, maybe grab a hotel room, and be back before the end of the weekend. But then Dad called from his business trip and said that he wouldn't be back when he thought he would, and he'd see us in another week. On top of that, Mom's friend called and cancelled too; which, you would think would be the end of it. But, even with her original motivation gone, Mom still REALLY wanted to go. She told me she'd been getting herself 'worked up' about it for a solid 2 weeks now, and to have it all fall apart on the same day that it was supposed to happen was frustrating her to the point of madness.
That... is probably why she got a conspiratorial grin, mid-conversation, and turned to me with the same look I'd seen her give Dad when she was going to try to sweet-talk him into something he knew he was going to hate. "Sayyyyy..." she began, and I was already instinctively scooting back. "...oh don't be like that". She said pouting. "I just have a proposition for you is all, and it's one that I think you might really like...".
Then she told me her plan, and, later that night, we were on the road to the club. Both of us.
Mom had made a very simple, and compelling case. After all, she wanted to go tonight, and I had wanted to go since I found out places like this even existed. So, if I was her escort, then we both got to go, she could have her fun, and, if things panned out, I might even get to have mine.
So, Mom informed me that, apparently, a fairly big part of what her and Dad did was all about the fact that, she, "Was Dad's". His presence, her sitting by him, the wedding rings, the hand holding... all of it, was a huge turn on for many. As such, for Mom to have the fun that she'd originally planned on having, she wanted a man with her. She wanted someone to walk in with her, hold her hand, sit and talk with her, wear a ring on the correct finger, and, when the time was right, she'd end up with someone else.
Mom explained it over and over again on the ride there, and it got to the point where I was stopping her half-way through her sentences with, "I know Mom! I know the plan!". Then I would tell her own speech back to her, just to avoid hearing her tell me it again. Simply put, we would "hang", and if anyone came up and asked her if they could do something terribly inappropriate with her, I would say yes, send them off somewhere, and then she would leave to have her fun, and I could "browse", and see if I could find any fun of my own. Honestly, my worst case scenario was to spent the night in a voyeur's paradise, witnessing first hand all the things I'd begged just to hear about.
It was... strange. I mean, I'd flirted with Mom for almost a full year now. I'd heard all kinds of stuff about her and her sex life, and, if I'm being honest, I had ABSOLUTELY masturbated to some of the things that she told me. And that required picturing them... But, that was all different from this. Because even if we weren't actually there to do anything together, I still parked the car with her in the passenger seat. Then we got out, held hands, and walked in together.
I was walking into a sex club with my Mom, and people were looking at us and seeing me, and this knockout MILF, with big tits, and long beautiful hair. Her top was low-cut enough to be sinful all by itself, but the fact that I knew she'd left her bra in the car only made it that much more erotic. Her skirt was much too short, and on the way in, I'd been a single stiff breeze away from knowing if she was wearing panties. Still, with that perfect ass of hers and that sexy little gait she had to her walk, I was struggling to walk correctly before we were even in the front door.
We signed our names, and no one blinked at the shared last name because we were playing husband and wife. And on top of that, the truth was that if we had "played" Mom and Son, no one would have batted an eye at that either. I mean, what's one more fetish in a place like that?
So, we got past the entry area, and into the first few big rooms of the club proper. I walked towards an area with a bunch of couches and chairs. There were people talking and laughing, and just having regular conversations, except in really sexy corsets, a few kinky outfits, a lot of leather, and some outright nudity.
There was lube, paper towels, and wet-wipes, pretty much everywhere. And though I was very aware of the sex, nudity, beautiful women, and naughty games that were happening all around me, I was just as aware, and just as turned on, by all the eyes that were looking right back. I mean, I was "on the menu" here, and people were checking me out like they might want a taste. Of course, they were checking out my date too, and somehow that was just as hot. Even girls were eyeing my Mom, like the sexy babe that she was, and I was a weird blend of proud, protective, turned on, and confused by all the attention she was getting. But I had to admit, though I didn't understand why it was hot, I was definitely finding it hot. And there is a pleasure to that "heat", all by itself, so I wasn't complaining.
Mom and I had a seat on one of the couches, and I was flushed, thirsty, and quietly looking around trying to "record" as much as I could with my brain. Meanwhile, Mom was relaxed, and, as always, charming. In no time at all she was a part of several ongoing conversations, and, on occasion, II heard her say something like, "Don't mind him, he's just the strong, silent type", and then her hand would pet my thigh.
I don't know how long all that went on, but at some point, Mom tapped my shoulder, and I was forced to look away from a woman in a stockade who was blowing a guy while a woman, literally, whipped her ass. When I did manage to look away, so I could see what Mom needed, she whispered in my ear. "This is nice sweetie, but it isn't exactly the attention that I'm here for. Do you mind if I... if I try something a little more drastic?"
That... got my attention. I was a little concerned at Mom's choice of words, but honestly, if nothing else happened tonight, I'd already seen some of the hottest shit I'd ever seen (in fairness, that wasn't saying much, but still). I'd more than had my end of the deal honored, and I was pretty sure the erection I'd been sporting since before we got all the way inside was proof of that. So, fair being fair, I nodded and told her yes.
At that point, Mom, very casually, continued her conversations, but, with a, "Oh no, don't mind me. I'm just getting more comfortable", as she straight up straddled me. And, as she ground herself down into my lap, I, not knowing it was coming, didn't move my hand away in time. So... yeah. That was how I found out that my Mom wasn't wearing panties. When her wet pussy bumped my hand, before grinding down onto the tent in my pants.
I won't lie, I moaned. I couldn't help it! Maybe if I'd known it was coming, I could have, I don't know, mentally braced myself or something. But instead, Mom just stood, threw a leg over me, straddled me, and as her body slid up the length of my hard-on (through my clothes), I moaned...