Having threesome with my then girlfriend and her older sister. In theory, there probably was a tiny chance of this could've been happening back then, so it wasn't super impossible by any means, but we never really got to talking about it because I was too scared to bring it up first.
They were very very close to each other and seemed like they 200% trust each other. Because of how close they were, the three of us often hung out together and naturally I became close-ish to the sister too. One day we went to their family's holiday house for a long weekend. My girlfriend and I overslept on the first morning there and the sister came into the room to wake us up. Both my girlfriend and I slept naked, and I had morning wood. The sister saw it and said that it was nice to finally see the cock to match to the story. I didn't quite understand it at the time, I found out later on the day that my girlfriend told everything to her sister including about my dick and our sex life.
Then on the last day, we spent a lot of time in the pool and for some reason my girlfriend was very playful and flirty with the constant tease. Flashing her boobs, mooning me when her sister wasn't looking, grabbing my dick under the water, and so on. The constant tease made me very horny. We made up an excuse to get out of the pool first, and we immediately went to our room to have sex. Once done, I pulled out and cum all over her. I then laid down on the bed and stared at the ceiling in the after-sex bliss, until I heard her sister jokingly saying "Damn, I got to see the cock the other day and now I get to watch the show too?" My first reaction was more "oh shit" but she just calmly grabbed my girlfriend to the bathroom to get her cleaned up.
I never quite know what the deal with the sister is. She was too nonchalant about the whole thing. Not against seeing my dick and me having sex with my girlfriend and cumming all over her. But never showing any sign of interest in anything more. The closest thing was when we said our final goodbye at the airport as their whole family moved out of the country (my girlfriend and I tried long-distance relationship for 6 months after that before we decided to break up) where she gave me a supposedly innocent kiss on my cheek, but I felt like the kiss lingered a little too long and she kind of inhaled hard as if to smell me. I remember being really turned on by that, but I never got to know what she was thinking.
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