So, as I sit here on my Super Friday before my vacation, I thought I’d type up my story to see if I can get the same quality of private messages from women that my last story instigated. This story is somewhat the opposite of my previous story where I told the sordid tale about having sex with my girlfriend’s mom. This is about the time I did NOT have sex with my girlfriend’s daughter.
Not too many years ago I was dating a woman who wasn’t named Cathy. She had three kids and her youngest, who wasn’t named Madison, was still living at home. Madison had a serious pot and alcohol problem. She was a year or two out of high school and dating these two guys, not at the same time, but going back and forth from one to the other. It was a whole, big, tangled thing. Both guys hated each other, wanted her like you wouldn’t believe, but treated her like crap to the point where she’d dump one and go back to the other. For some reason she just couldn’t get out of that loop.
Madison had lots of fights with Cathy when one of the guys would dump her off at home, wasted and reeking of weed and booze. Now Cathy is a whole big, hot mess herself and her story is a multi-post worthy saga in and of itself that I don’t want to get into. But as necessary background I’ll say that while she was going through a divorce with Madison’s father, he, in display of excellent parenting, showed their three kids a very detailed PowerPoint presentation of all the shit their mom had gotten up to all the way back to when they first started dating in college. Seriously, a PowerPoint presentation complete with pictures, video clips and theme music. As a result of this, whenever my girlfriend fought with Madison, her daughter had plenty of shit to throw back in her face.
One lovely Saturday, Cathy is having a yelling and screaming match with Madison who had stumbled down the stairs at 2 PM still hung over from the night before. I’m in the living room pretending to watch TV. Madison storms into the room yelling, “how about if I just had sex with your boyfriend then!” and takes off her shirt to come display herself in front of me in nothing but a pair of skimpy panties. I stopped pretending to watch TV.
Okay, lets back up a tiny bit. Cathy, her mother is still pretty hot in her early 40’s. She’s skinny and keeps herself in shape. She had her breast done after having the kids and has that overall look that suggests she is hiding some kinky secrets under a wholesome outward appearance. Her daughter is a younger, hotter, fitter version of that with natural breasts that were about the same size as her mother’s purchased pair.
There is a lot more yelling and screaming, attempts to drag me into it with comments like, “Oh, you know he wants me. I bet you a billion dollars he’s hard right now!”
Narrator: “He was quite hard.”
It ended with Madison storming back upstairs, but not before stopping to smack her ass for me, saying, “You know all this is much hotter than my mom.”
And such a lovely, ass it was. Cathy had an okay ass, but Madison had been into various athletics in high school and had one of those tiny, taunt asses that you could bounce a quarter off. An ass toned like an Olympic runner or volleyball player. I’d have eaten that ass for days.
Now Cathy and I had a great sex life. The rest of the relationship was crap, but the sex was fantastic. She knew exactly what my buttons were and was an expert on pushing them. Like me, she liked the idea of sex being tawdry and dirty. Blowjobs in parking lots, stripping naked and masturbating in the passenger seat while I was driving on the freeway, wearing skirts that are too short for decency standards and advertising that one of the great benefits of having fake tits is you can look great in a partly sheer blouse without a bra in a nice restaurant. Our dirty talk in bed went deep into things we’d done and our way over the line fantasies. We had even been to a sex club a few times where we once swapped partners with another couple.
That night she started talking about Madison, “You know you wanted to fuck her, admit it you were rock hard when she took off her shirt.”
We’d done the adversarial, but playful, dirty talk like that before and the strategy is not to let the other person get the upper hand. I responded with something like, “Are you kidding, I’ve been wanting to bang your daughter since the day I met her.”
Those two incidents started it off and for the next several years it became a running joke out in the open and one of the dirty talk subjects Cathy used to satisfy me in bed.
Madison would tease me about it, make jokes comparing her breasts to her moms, suggest blowjob competitions and the like. Cathy would pretend to argue with Madison about who’s turn it was for me that night, or which one of them I was taking on vacation, etc. On a couple of occasions Madison would allow me to get a quick peek of her tits or ass. She’d bend over in front of me suggestively or she’d brush up real close while talking to me. She liked to sit a little too close to me on the couch all the while touching my arm or my leg in the middle of a conversation. There was a lot of daring, both when we were alone and when her mother was present.
One time she called me out for staring at her ass when she bent over, and I countered that she was damn right I was looking.
She asked if I liked what I saw.
I told her to come sit on my lap and feel for herself!”
It was like we were both just dancing on that edge to see who would chicken out first. One time she came close to talking me into taking out my cock so she could judge how big I was.
Anyway, in bed with Cathy is where it got really dirty. Cathy like replaying these things back. “What would I have done if she did come sit on my lap?” “You should have shown it to her, let her see what a real man’s cock looks like.” And from there we’d start building these perverted scenarios while we fucked.
There were a couple of high points during sex that each escalated the paradigm. The first was when Cathy came out wearing her daughter’s old high school pep squad costume. It didn’t really fit, she had bigger hips than her daughter, but a partially unzipped skirt barely hanging on is still hot. That introduced the roleplay of me fucking her daughter THAT SHE TOLD HER DAUGHTER ABOUT!!! It might have even been her daughter’s idea, I’m not sure.
One night I said that I didn’t want to fuck her daughter, but rather that I wanted us to fuck her daughter. I wanted a good ‘ol fashioned mother-daughter threesome. Cathy already knew my big kink is having two girls in a threesome and that caused a complete tonal shift where the dirty talk shifted from me having sex with her daughter to the context of us having a threesome with her. Sick and perverted, you say? Oh, you have no idea.
The really big one was when her daughter left herself logged into her Google account on one of her mother’s many tablets. This led to Cathy accidently stumbled into her Google Drive where there were a couple of videos of her daughter having sex. Did we fuck while we watched her daughter’s porn videos? Yes. Yes, we did. Madison would also constantly be taking pictures or videos of herself to text to the guys that we could also see.
I don’t know for sure, and I honestly am not sure on the order of these events, but I think Madison either knew we were seeing her pictures and maybe even set it up with her mom. I say this because Madison would make suspicious comments all the time. I of course can’t think of any of the ones specific to that now, but one thing I do remember her saying that still turns me on is when she was complaining about her vibrator being so loud that she could barely hear us having sex.
This all happened over the period of about three years. I broke up with Cathy several times during that period, as I implied before, the sex was great, but the relationship wasn’t. Partly my fault, I’ve got my problems too. But like I also said, she was an expert on pushing my buttons and could get me back into bed with her with little effort even if was with somebody else. Madison got arrested at one point and agreed to a drug and alcohol program to get the charges reduced. She had to remain clean for her entire probation period, which she did. She cut alcohol out completely afterwards. She is still a pothead, but it was obviously the booze that was her problem. At the same time, she finally got free of the two jerks she was dating. I also finally broke up with Cathy for good and she thankfully moved back to Minnesota to live near her aging parents, well out of reach.
There is a lot I left out because of the extended explanations that it would require. But in conclusion: No, I don’t really think there was any chance that Cathy wanted to do anything with her daughter, I am sure that was just her playing along with a perverted fantasy because that’s the kind of thing that turned us both on. Would she have been upset if I did fuck her daughter? I’m not sure, but I think she was sure that I wouldn’t and that it was all just fantasy. I’m pretty sure that Madison really liked the idea of her mother’s boyfriend wanting her, I think she might have even got off to the idea, but I don’t think she had any real desire to be with me. Except when I’m masturbating and taking a trip down memory lane and then all bets are off. Though, I do wonder if Madison did the same kind of dirty talk about it with her boyfriends that her mother did with me. I also wonder if Cathy shared any of the videos and pictures of us with Madison?
And guys, not only do I not want to trade pics or videos, but I also don’t have any of either Cathy or Madison as she asked me to delete them. One of the key elements to getting women to allow you to take these types of pictures or videos of them, is the understanding that you aren’t going to share them with random people on the internet and that you’ll delete them when the relationship is over if they so desire.
Source: reddit.com/r/gonewildstories/comments/v59f1j/the_time_i_did_not_have_sex_with_my_girlfriends
Great story, i liked it