This is mild and short by my standards, but enough people have asked for updates about my ongoing situation with the slutty SIL, I thought I’d share the preparations of what’s to come later this week!!
I left Cindy’s house with mixed feelings: On the one hand, I wanted to stay and use her more, but on the other, I felt she was already clingy enough and spending the night may send the wrong message. After all, fucking my brother’s wife for fun was completely different than having her fall for me. I may be an asshole, but I was not a complete dick.
In the car, I immediately thought about setting her up to fuck strangers. The idea was clearly a turn on for her and would be the ultimate in degradation, but I also thought about diseases and not wanting a bunch of random guys screwing her, condoms or not. Then, a plan started to form. I hit the phone button and went to favorites. Finding the number in question, I hit dial.
“Hey mate, how’s it going?” Jim asked upon answering.
“Jim, just had a fun night with the sister-in-law.” Jim and Lucy knew about my recent conquest of Cindy and liked to laugh, joke, and give me ideas regarding the whole situation. “Do tell” he responded. I proceeded to give him the cliff notes version, realizing partway through he had switched me to speaker, so I was guessing Lucy was listening in. Once I knew that, I got more specific, especially around the spanking. I paused before revealing the reason for the call, and Jim laughed “Wow Jake, you’ve gone and gotten Lucy all worked up. She’d she hi, but my dick is in her throat currently.”
I laughed and told him the rest. “Jim, best part is she told me at the end she was totally turned on thinking about me offering her to the neighbor if he bought her. So, it gave me an idea.” I went on to discuss my plan: Rent a hotel room Friday the before Memorial Day. Let Lucy know she was going to be tied down and fucked by random strangers, but the requirement was she wears a blindfold the entire time. I’d assure her I vetted the strangers and I’d be there to watch and make sure nothing went wrong. However, unknown to her, it would be Jim and Lucy having their fun with her and not complete strangers.
That way, it would be safe, but she would not know. Lucy stopped sucking Jim long enough to ask: “Can I bring my strap on too?” I confirmed that she would be able to do as she pleases, after all, they were paying for a fuck toy and should be allowed to play as they would like. Jim said they were totally in and then asked if the three of us were enough. We talked a bit more and decided I would invite one more of my friends, single, clean, and likely up for it, to add to the mix. The four of us would take turns using her and make it seem like we were all strangers. By the time I was home, the plan was set, Mike was on board, and likely Lucy had a mouth full of cum.
I texted Cindy “Friday night, next week. You are going to have a girl’s night in town. Do what you need to arrange it. I am going to list an ad online selling you and will pick the highest bidders. We can talk details later, but you are going to be used by several people and if they pay enough, I may let them cum inside you. For your part, you will be a good little slut and take them all, understood?”
It took a while for a response, but when it came, it was short: “Yes Jake.” I jumped online, found a hotel with decent rates, and booked two rooms: A small one bedroom suite for Cindy and the “fuck” room and a second standard room for Jim & Lucy. Mike was local, so I figured he could find his own room or just go home, depending on the time. Jim & Lucy would need to stay the night, as the trip was about an hour for them. Once confirming, I went to bed, fantasizing about the fun we would be having in just over a week. Ellie facetimed before I was asleep, so I explained the situation to her, and we masturbated together. All in all, a rather fun and eventful night.
Source: reddit.com/r/gonewildstories/comments/nk6j8u/my_little_fucktoy_preparations
Can’t fucking wait to read the follow up to this!!!