Author's Note: All characters in this story are at least 18 years of age, and, even in role play, are "playing" characters who are at least 18 years of age.
***
...I still had no idea how any of this was going to work, but Mom very clearly wasn't shutting it down. Like at all. And just when I thought we were about to go and sit with Dad and get ready to enjoy some fireworks, Mom used my arm to pull me in close so she could whisper something. Then, she purred a question into my ear from so close that her breath was hot along my skin, and sent little shivers down my spine. She whispered, "So kiddo. Exactly how kinky does this Mommy fantasy of yours get?" I pulled back enough so that I could see her face when I answered her, and the moment that I did, I could tell from the look in her eyes that, if I played my cards right, my second incredible sexual adventure would start on the same night that my first one had!
The first signs of twilight were starting to show, and people at the cookout were starting to engage in the seemingly annual American tradition of "getting ready for the fireworks to start" WAY too early. That early buzz of "oh look, the sun will be setting soon, we should find good seats" started to go through the guests at the party.
So, as the guy that my Mom and I had been talking with moved up to meet up with his date, Mom held me back a bit and pressed me for an answer to her question again. "Well?" She said, her tone mildly teasing. "Just how naughty do I get in these fantasies of yours?"
It was a big question, one that was way bigger than I suspected she knew, and I gulped at the prospect of just answering it. Like, lesson learned, I definitely wanted to be honest! But at the same time, I didn't want to say too much and have my Mom never be able to look at me the same again.
So, I tried to soften the blow by giving a little laugh, and clarifying that, obviously, there was a difference between what I fantasized about and what was actually possible. I was referencing the fact that most people could fantasize about a gangbang all they wanted, but not only was that never really going to happen, most people wouldn't know how to handle a real one anyway. But Mom knew EXACTLY what I was talking about, and after I said it she grinned, raised her eyebrows at me, and took a moment to glance around at the swingers and kinksters who made up the total guest list of this party. Then, as if to emphasize the fact that this was her world, and I was the one who was only now dipping a toe into it, she said, "Oh, I wouldn't be so sure about all that kiddo."
I almost made the stupid mistake of pointing out the gangbang example, when, not only did I remember that the guy we'd just been talking to had said that he'd seen my Mom in action at the center of a blowbang, but that Mom had heavily implied that she'd already done all kinds of stuff that I could only find in the most hardcore porn available. I caught myself in time, but I still hadn't taken back what I'd said, so Mom added onto the pile of evidence countering my sensibilities.
"I've even heard," she said, lowering her voice and looking around before stepping into me to whisper the rest. "That one of the women here, deep-throated her own Son in front of a cheering crowd..." Then, with my blush growing and a fresh wave of heat melting my brain, she pulled away from her intimate whisper and shot me a sexy little wink.
I was at a loss for words after that, but Mom didn't let my stunned silence discourage her. Instead, she just started naming off kinky things and waiting for me to chime in, like I was going to point and say, "that one" at any given moment.
Then she started talking about how Dad considered her to be his "dream girl", his ultimate sexual fantasy, and so that lent itself really well to the swinging lifestyle, because there were a lot of things that you couldn't see or hear the woman of your fantasies do unless they, well, did it! So, he quickly got comfortable with not being the only guy she was with, if it meant that he got to watch his fantasies play out in real life.
At that point, Mom stopped and gave me a knowing smile as she said, "So, those fantasies of yours... the ones you worry would need to be left out of reality and exclusively in fantasy? Yeah... Mommy's probably already done them. Twice. In costume!" Then she wiggled her eyebrows at me. She was being playful, but she was also teasing me with the woman of my dreams doing the dirtiest things from my fantasies, and, you know, also my MOTHER! So, I was overwhelmed on a variety of levels.
But, since I wasn't giving her a ton of feedback, Mom just kept going. She talked about how Dad loved taking her doggy style, but he realized that he wanted to actually watch her get taken doggy style. To see her breasts swaying, and see the faces that she made when she was moaning out for more. Then, once that door was opened, he asked her how she felt about being with a woman. Or multiple partners, and so on and so forth.
"But, to really summarize all of it sweetie", Mom said, her tone still low enough that it was a private conversation while no longer whispering into my ear. "The answer to all of your Dad's, but 'Wifey Would You' questions, was a yes from me. Every time. So, what I'd really like to do here, is skip to the end a bit. Or at least to the middle!" She said, giving a charming little laugh and petting my arm reassuringly.
I... was still struggling. I know! She was offering me anything I could say, and I couldn't find the courage to say anything! It was just... That's my Mom! You know? I wanted it all, but I didn't want to fuck any of it up.
Mom waited, her eyes scanning my face and studying my expressions intensely as my mind raced and I tried to figure out what to say. But after a minute, her expression turned thoughtful. She seemed to go deep into thought for a moment, then her face lit up in an "aha!" moment, and she once again patted my arm, this time to make sure she had my attention.
"I know," she said, her smile absolutely stunning. "So, let's start by saying that I'm glad what happened tonight happened. I was serious about all of it. You know my policy on honesty..." She said, her tone serious for just a moment.
Then she went back to excitement as she continued, "So, I loved it, you clearly loved it, and here we are wondering what comes next right? What's in the future? Well, why wait for the future, why not try something crazy, and dirty, and fun... right now?"
Yeah, she had my attention. Everything about my body language told her to "go on...", and in traditional Mom-fashion, she read me like a book. "Okay..." she began, her tone going conspiratorial as she excitedly whispered to me what she had in mind while also leading me around the side of the house and, in a very round-about way, towards our car. "Let's start with some first timer stuff, but make it a little more advanced. So, the first thing I need to know is, do you want to watch? As in, is the idea of watching your Mother having sex hot to you?" I started to open my mouth to answer, and Mom turned slightly and touched a finger to my lips to stop me. "Honest answers only. Please don't disrespect me or yourself by wasting our time with half-truths."
I was going to answer honestly, fully and truly. Not sure why I was more okay with that now that I had been just moments before, but I was. So I nodded to assure her, and then I told her "Yes". I thought the idea of seeing her be sexual, and engage in sexual acts, was super hot. I'd honestly been fantasizing about catching her at a swinger party ever since I'd learned she went to them!
When I admitted it, Mom grinned from ear to ear. She seemed super excited and happy. Honestly, I felt the same. This was crazy! But in a good way. When we got to the car, I opened the door for Mom since she waited at the passenger door, and then, since there was no one else there, I got into the driver seat of my Dad's car.
"Won't Dad need..." I started. But Mom quickly hand-waved my concerns aside and assured me that he was hoping to "sleep-over" anyway; and the plan was always for Mom to take the car at the end of the night so that she could meet up with my Big Sister, Tasha.
In the car, Mom dropped a bombshell of a question on me. "So..." she started, the tone shifting and the mood suddenly a little awkward. "If we rule out stranger danger, and the people who are at this kink party or one of the other ones, that sort of just leaves your friends as people who might enjoy what we are talking about, and who can be trusted to, you know, not murder us. So... does that still sound good to you?"
She sounded so unsure of herself all of a sudden. Her hands were clenched in her lap, and now it was my turn to read HER body language. She seemed anxious, but only because I think she was afraid I would say no. It was a really bizarre question, and on any other night it would be either the stuff of nightmares, or at least it would have very much screamed "trap!". But now?
"Do you mean that you would... them?" I asked, like a suave person would.
Mom nodded, and I took a moment to think about it. "Would that work?" she asked into the silence. I'll be honest, at first I wasn't sure. Like, at all! But, the moment I pictured my Mom on her hands and knees, moaning, her tits swaying at she got fucked from behind... HOLY SHIT! Yeah, the answer was yeah! As long as she was safe and she was into it, I was beginning to realize that I didn't fucking care who it was!
In my head, I acted like she couldn't tell my face was now bright red from blushing, or that my cock was rock hard and pressing hard into my clothes again. I just cleared my head, and cool as I could, I told her that yeah, I would be okay with that.
But, the "how" of it suddenly hit me, so I asked her how we would even pull that off. At which point Mom let out a laugh, and I saw all the tension leave her. She'd been worried about my reaction, but not about anything that came after.
She patted me on the leg with an "Oh you! You're so silly" gesture, and then made the reason for her confidence clear when she asked me, "Sweetie... Do you think that your Mom is going to have a hard time trying to seduce a room full of teenage boys? Let alone a group of 18-19 year-olds that have been blatantly trying to sneak peeks at my cleavage line for the entirety of their post-pubescent lives?"