Upon having this idea, I came to find myself in a bit of a pickle: in the stories, the characters are all lifelong friends who trusted each other completely; I had no such friends, nor would it be beneficial to start hanging out with someone just for this. So after dinner, I did the riskiest thing on this earth: I made myself a new email and put an ad on Craigslist saying I was looking for help pulling a prank on a friend, specifying that there was some sexual components to what I had in mind. Once the ad was live, I forced myself to do some actual school work and wait for the morning before doing anything else with this crazy idea.
It wasn’t until about a week and a half later that I finally got a hit from the ad. I’d feared that nobody used the site anymore, but the guy said he wanted the details of the plan as he was intrigued by a sexual prank war. Having had ten days to truly think this over, I’d come up with an idea as to what I’d tell people that were interested in helping (obviously I couldn’t tell the truth of my wanting to fuck my mom and sis), so I told him that my buddy was a virgin but he and his girlfriend were too uptight about this sort of thing, so I was trying to be a bro by giving him a helping hand so to speak. I wanted the guy to ‘break-in’ and force the two to have sex. Not only would this get them over the hump, but if my ‘friend’ acted the goody-two-shoes that he was and tried to protect his girlfriend, it also makes him seem like a hero to her and not at fault. I said I’d eventually reveal this to them, just not right away as I hoped my actions would be undetected and they’d allow themselves to enjoy the gift of sex. I stressed, bolded and underlined, that this was solely for my buddy and his girlfriend to get theirs, and the guy wasn’t allowed to participate in any way, shape or form. No photos/filming of any kind, and that just to be safe he was to show that he was turning his phone off; my buddy and I would undoubtedly talk about this and I didn’t want to have to track down any loose ends.
Surprisingly, the guy was onboard for all of this, including the not getting involved part (hurray for asexuals with dubious morals) and said that this was such a weird but touching thing that he wasn’t going to charge his normal rate of $5000, but give me a discount of $2000 so I’d only have to pay 3K. It was a bit more than I wanted but, his no questions asked, the discount and general discretion were hard to pass up. Thankfully, I’d had money saved up from birthdays and Christmases and doing some odd jobs for the neighbours every so often. All together I had about four grand in my bank account. I told the guy that it was a deal and that I’d get back to him with a date, time and place, as well as where I’d leave some supplies; he was responsible for concealing his identity. And with that settled, I awaited the Christmas holidays.
During that agonizingly long month wait, I continued to try and improve my grades (which I started to make some progress on), as well as continue to try and spy both Mom and Rheta during times in which they thought they were alone. There was another night where I got to overhear Mom’s filthy mouth, again I came in my shorts just from hearing her words (but this time I had the foresight to bring my phone and so I got to record the whole thing, and that file is saved deep in my computer). But the best thing to happen was when I came downstairs late one night and, sitting on the couch with her hand frantically rubbing her pussy, was Rheta. On the tv was a picture of me from this summer, in my bathing suit, posing like some Greek statue of a muscleman (reverse dab and pointing to the sky) and looking like a dork. “Oh, BIG brother! You rub my pussy so good! Please Henry, stick it in, I need to feel your cock in me. Pound my virgin cunt, brother! Spew your cum on my face and titties so it dries on my face and then pound me again until I’m overflowing with your cum and I can’t walk anymore! OHHHHH!”
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