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I possibly have the chance to become a live in houseboy. Does anyone have any experience/advice?
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I am a nineteen-year-old submissive man who has been attending local BDSM community events for several months now. Over that time, I have started to get to know a very kind older woman. We first started just talking in groups at munches (most of the people in the local community are Male Dom and Female Sub, so those of us that are Fem Dom and Male Sub tend to gravitate together) before playing a few times at some parties. When we found out each other's ages, we were both surprised. She thought I was in my mid-twenties and I thought she was younger than she was (she's 55).

Recently, she invited me to move in with her as a live-in "houseboy". I would be expected to do all of the chores and housework, as well as to serve her sexually when she desired it. She works a full-time job, so during the day, as long as I get done whatever chores I need to, I can do whatever I want, as long as I'm available for her in the evenings. She has been clear about not wanting to push me into anything I don't want to do and has offered to help me pay for some of my college expenses. She wants us to try it out for 2-3 weeks to see how I like it before we start any major changes.

This seems like a great deal, as I would have the time to work on college full-time, without having to worry about housing or food. Plus, her willingness to help cover some of the cost would be great. She is also willing to be my full-time chastity key holder, which I've always wanted. She's also been clear that she's not interested in having any boyfriend/girlfriend type of relationship and that if I find a younger girl that I would like to get in a relationship with, she's perfectly fine with that, but she wants to be my sole keyholder during the time that I'm her houseoy.

This seems too good to be true, but she put me in contact with a guy who had been one of her previous houseboys. He told me that she is very kind and generous with her money (she bought him a car) and that while doing chores and pleasuring her sexually is all part of it, most of it is being there for her as a companionship. He thought she was a little bit lonely with few friends and no close family, so she liked just having someone to go out on hikes with or sit at home and watch TV with. Having this person be a younger, fitter man doing her chores half-naked around the house was just a bonus.

I'm seriously considering taking her up on her offer, but I'm also slightly nervous about it. While she's very nice and I'm positive she wouldn't take advantage of me or force me to do anything I don't want to, it's a big step. I'm also concerned about how my family would respond when they find out I'm living with a woman more than 10 years older than my Mom. Even though I would never tell them about the nature of our relationship, I'm very close to my family and I don't know if I would be able to keep where and who I'm living with a secret to them.

Does anyone have any experience with an arrangement like this? Any advice would be greatly appreciated.

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1 month ago