My wife and I have used a house cleaning service for about 5 years. After a while, we started getting the same girl (Madison) cleaning our house every time. She was a sweet, cute college kid who did a really great job, so we always requested her. I work from home and my wife occasionally has to go into the office. Madison usually cleans for us 2x a month of Fridays, so my wife only sees her about half the time.
So…I use sites like Seeking Arrangement to find sugar babies and fuck them. One time, I was on there just browsing around when I happened to see Madison’s profile. I immediately freaked out and quickly blocked her so she wouldn’t see that I’d seen her page, but I couldn’t shake the thought. I’d always wanted to have her, but never assumed she’d be up for anything like that.
The next time she was over, I purposely made a casual joke about her needing to win the lottery or get a sugar daddy so she didn’t have to clean houses anymore. She laughed and said something like, “I’d take either!” That was my opening. I just straight up offered her an arrangement on the spot. She accepted.