A few years ago one of my best friends was dating a gorgeous blonde. 5’3, C cups, incredible ass. She was totally out of his league I still don’t know how he managed to get her but they had been going out for around 6 months at that point. I joked around with him on how he must have paid her or something, but he was very cocky and confident saying she was the one that got lucky lol. One day the same conversation came up again after some drinks, and he was super confident she was the lucky one and she was way too loyal too. I questioned that a bit and his competitive side kicked in to where he proposed a bet. He dared me to slide into her dms and see how far I could get here to go with me. He was sure she would cut me off right away. The bet was as follows. If she cut me off right away, I would have to not only pay him, but also tell her how lucky she was to have such a stud, but if I could get here to agree to go for a coffee with me or something along those lines, I would get paid, and get free drinks from him for a month. Oh, and nothing was off the table in terms of her. Of course this was a dumb bet but overall a win win situation for me I decide the best bet to slowly talk to her is to comment on a couple of her pics on ig. I comment on a specific picture I took of her one day we all hung out saying what an amazing job the photographer did. Right away she messages me saying indeed I was a great photographer and that she actually needs a few more pics taken for her profile. She asks when I’m free so we can all hang out and take some cool pics, etc. From there I knew I had it. More innocent conversation goes on here and there and then I bring up the topic of the photo shoot…but I tell her we can leave my friend out. At first she is hesitant and does not think it’s a good idea. I just mention it would be fun and we might be able to get better pics without the pressure of her bf being there, she politely declined the offer and I don’t insist. Two weeks go by and we don’t talk, when suddenly out of the blue I get a message from her. “Let’s do the photo shoot. The bf will be out of town for a couple days. I reaaally need new pics.” I initially thought I had lost the bet, so by that time I had paid my friend already, but things were about to take an unexpected turn……