Over the last year, I’ve gotten myself into a somewhat submissive relationship with a 58-year-old woman who lives in the apartment next to mine. I’m on the 4th floor of a loft-style apartment building. In the back on the outside is a long narrow walkway for the fire escape. I have 2 uncovered extra large windows and a glass door with a view of the Delaware River.
I’m 28, have a good job, fairly intelligent yet I let Jessica manipulate me.
It actually began back in late 2017 when one night I noticed Jessica out on the walkway peeking into my apartment. The back of the building is sort of desolate with no roads and just a stretch of ground before the river bank. After work, I stayed naked most of the time and thought it was funny the first time I knew she was looking in my window.
I was living here 5 months at that time and don’t know if she had been doing it before that. I couldn’t imagine at the time a woman her age being a peeping tom so I just continued being naked and never have put shades on my windows.
I spoke to her a few times a week and last year without me ever mentioning that I knew she was watching me at night, she told me she was doing it and said she liked seeing me naked. A few nights after that she was out there again and knocked on my door. I was naked and when I went over to the door she asked if she could come in. I have to say she is not attractive but for some reason having her see me nude was arousing for me.
We sat down and that’s when she began telling me how often she has seen me naked and about how many times she watched me masturbate. Over the next few months, she began coming in a couple of nights a week and persuaded me to masturbate for her. About 7 months ago was the first time she jerked me off and now I not only let her spank me sometimes but I have let her take control of me.
Never had I been anally penetrated before but Jessica uses her vibrator and a small dildo to stimulate me. She puts KY on it and slides it into me as she is jerking me off. I can’t believe how good it feels never thinking about anything like it before. She never gets undressed and always wears these ugly housecoats that remind me of the stuff my grandma used to wear.
Jessica is really a strange woman yet I let her dictate me and I know she likes spanking me. She doesn’t sneak out on the walkway anymore and just calls me and says when she is coming over and tells me to be naked. It goes on twice or more every week and I just do whatever she says. What’s crazy too be that she calls me a child lots of times and wants to control when I ejaculate.
I never resist her and let her have her way so that proves it’s my fault. She even makes me tell her when I am ready to cum and has me ask if it’s ok with her. That is what submissive is and she is very good at it.