Cassandra' Taboo Pool Parties

Story by: Cassandra
Edited by: B.C. Kingston
Artwork by: B.C. Kingston

Editor’s Note:

WARNING: This story involves the taboo topic of incestual sex. If you are offended by such things, please turn away now.

What follows is a “true” story as relayed to me by Cassandra in numerous email exchanges. Her original description of events is presented below with minor edits for readability. Afterwards, there is a QA style exchange between Cassandra and I clarifying additional details about what happened.

The events took place in the early 2000’s. The memes are inspired by the story, but based on more recent pictures that Cassandra provided. I have no proof to any of these claims beyond the details Cassandra has given me. Do I believe her? Yes I do...


Cassandra’s Story

I had a very boring and plain sex life until my first marriage ended. My first husband was my first for everything; including kissing, the first man I saw naked, the first person who saw me naked, etc. I grew up very conservatively, my dad is a pastor so we were basically taught sex is very private for man and wife. So we grew up thinking sex was as an act for man and wife, almost like it was just something you did when you were married to have kids. We grew up in a different time totally different from now where everything on tv and the internet is about sex. The internet didn’t even exist!

So when that marriage ended my close friends and my sister always tried to convince me to "let my hair down" and go party, to meet and sleep with random men, to have some fun and see what I was missing out on. Well the idea always turned me on, but I was very hesitant to do anything, since I never had before.

This is when things got a little strange. Thinking about being with random men, and letting loose sexually really turned me on. I mean, I wasn’t out having sex with strangers 24-7 but I was always horny! Mostly, I just had a toy that was very heavily used, but my sexual nature was starting to slowly come out.

Well one night my middle son and a bunch of his teammates/friends were over at the house, they were probably all 16-18, and I overheard them talking about me. Commenting on my appearance, mostly my boobs, and that they noticed I wasn't wearing a bra. And they started asking my son about if he had seen my boobs, or seen me naked, then went into what they wanted to do to me.

Keep in mind that this was all before my breast reduction. I’m a DDD now, but they were even bigger back then (FF).

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Well I slunk back into my room thinking I was a bad person for letting them think that or that I was being inappropriate by not wearing a bra. But I never wore a bra at home and most of those boys were around as small kids, so I didn't change the way I dressed around them figuring they were used to it and it wasn't weird without thinking about the fact that they were hormonal teenagers now.

But at the same time part of it really excited me and it brought the exhibitionist out in me over time. Like I would purposely walk around them without a bra on and on nights I was feeling daring at the time would bend over in front of them and show some cleavage, or move in a way they bounced. Then would try to see if I could catch them talking about me. The more I heard the more I liked it. Which lead me to start wearing more revealing tops around the house, or even a few times wearing one of my son's wife-beater/tank tops without a bra, which was almost see-thru with my chest. It just drove me crazy knowing they were looking and admiring. I never had that kind of attention before so it was very, very flattering and a new exciting feeling.

So I took it a little further and when they were around I would wear my basically non-existent tiny bikini's around the pool. Really they barely had enough cloth to cover my nipples, and if I didn't shave my downstairs area, you could see it. I normally only wore that if I was alone, just had family around, or in a tanning bed. Well I started wearing them around the boys, pretty blatantly showing off. Which backfired a few times when they got in the pool with me, or pushed me in. I had so much boob crammed into the small top that any movement would jar one loose. But seeing their faces when that happened, and hearing them talk about it excited me even more.

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This was mainly my fault, but eventually I caught my son and a couple of his friends trying to spy on me. Like watching me through windows or cracked open doors trying to catch me changing or something. After catching them a couple of times. I sat my son down and talked about it. He told me that I was "the hot mom" all of his teammates and friends talked about, and once I started wearing the little bikinis and skimpier clothes around the house, he started to notice what they were all talking about and he was curious.

It didn't make me mad or anything, it just creeped me out some not knowing who it was watching me. And since I was basically asking for it by the way I dressed and teased them, it was totally my fault. But again, knowing they wanted to see more badly enough to try and peep on me also excited me.

So I teased them a little. I never really knew when/if they were looking until they told me later, but I would start changing in my room where they could see through the windows, but I would never let them see anything but my underwear, or a few times I would take my top off with my back to the window where they could only see my back, then I would go in the bathroom and close the doors where they couldn't see anything.

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It was really exciting teasing them and wondering if they were watching. When it started getting out of hand was when I told my best friend and sister about it. They loved that I was doing that. They were both very, very promiscuous and well slutty for lack of a better word, so they convinced me to keep it going. Which excited me more knowing other women approved of it.

So I took it a little further, and would just wear a robe around the house and let it "slip" open on accident, or walk out in a towel wrapped around me barely above my nipples showing a lot of cleavage. Well the first time it really started pushing boundaries, my sister and friend were over at the pool (they wanted to see what was happening), with my son and a few of his close friends over.

So I came out in my tiny bikini. After we hung out for a while, my sister blurts out, Cassandra you might as well just take your top off, you aren't hiding anything anyways. Well I got embarrassed and tried to play it off. Then she asked the boys if it would bother them, which of course they weren't opposed. Well I'm bright red embarrassed and kind of in shock. My sister comes swims over to me and unties my top. I wanted to stop her but just sat there.

When she pulled it off I kind of snapped out of it and went underwater to my neck to cover myself. Well eventually her and my friend cheering me on got me stand up and just show them. I went inside not long after, but it was one of the most exciting things I had ever done, especially after my sister and friend told me about all of the boys being erect from it. But that lead to anytime I was around the pool one of the boys would tell me it was okay if I went topless or something, so after a while I would just go topless or even naked in the pool with them around (I eventually made my sister and friend do it too if they were there). that's when my comfort level with nudity really started to grow, where I wouldn't hesitate to walk through a house full of people topless or naked.

Eventually after listening to my crazy-ass sister and friend it got more physical. Over time we started doing things sexually with them in the pool and with each other to tease them. Which more or less lead to naked or sex parties at my house with middle aged women and high school boys.

In most people's opinions, we probably crossed every line. I mean women being naked in front of their sons, or having sex in front of them, isn't a good thing to most people. But it was great for all of us. I know the boys weren't complaining…

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Eventually more women got involved. We didn't add many boys since we didn't want what was going on getting around. So the family/taboo lines started to come up when more moms came with their sons there. We had all been comfortable being naked together and doing sexual things in front of each other. I was actually the first one who really did anything with their sons once we got more comfortable and sex was more open. But it wasn't by choice...

My sister suggested playing what was basically sex roulette. All the women in one room, all the guys in another. One at a time we would go out with a blindfold on and whoever was in the room we met in (living room), we had fun with, where no one knew who they were with and the other people didn't know either since they stayed in the other rooms waiting.

Well I was “volun-told” to go first. So one of my friends lead me to the living room blindfolded, until I bumped into a guy, she said have fun and sounded like she walked off. Well we went straight to making out, touching/feeling, then I got down on my knees to give him head. I was really into it not knowing who it was and just blocked out everything else but the physical parts, well then all of the sudden he pulls out of my mouth and cums all over my face, chest, and tits. As soon as he did I hear cheers, whistles and yelling.

We were supposed to be alone, so I pull off my blindfold, and everyone is in there watching, I look up and my son is standing there (he was blindfolded too until the yelling). They had set it up to watch me and him do something. Turns out he knew it was me once it started (because of my tits) and played along. My sister, and one of the other women had the idea to do it.

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I wasn't happy about it at the time, but after thinking about it, it really, really turned me on due to the forbidden aspect of it. But that also opened the door for others to do similar things. As you can tell we weren't very well behaved at all. I regret part of it, since it really snowballed and got out of hand, but at the same time I don't regret it. It was very fun, eye opening, exciting, and mutually wanted (other than the blindfold night).

Other posts in this story

Q&A

Barry conducts a question and answer session with Cassandra to get more details about her taboo pool parties and some of the other things that happened afterwards.

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