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Every Thursday
I'm 66 years old, live alone and have been divorced for 12 years. I have a small two bedroom house and although I golf and bowl a couple days a week I am home most of the time. If I don't go out I don't bother getting dressed and spend most of the time naked. Despite my age I masturbate daily and at times watch porn. On Thursdays I have a cleaning lady straighten up and do my laundry. Her name is Sheila, about 45, semi-attractive, and has been cleaning my house for more than 2 years. It didn't happen often at all, but she had seen me naked occasionally. Funny thing is she didn't get offended by it and just laughed it off. One incident was the middle of last May when she saw me naked in my bedroom. She just stood there shaking her head and said "not again Harry". Instead of leaving my room she started telling me I needed a new washer on my kitchen sink. It never happened before when she saw me naked but all the sudden I got an erection. That's when she walked out telling me I better "whack that thing".
I have had several girlfriends since my divorce but for the last few years my sex life has been nil and I returned to masturbation. That day Sheila didn't let up on me and joked around about her seeing me naked. She even told me her husband has a bigger penis than I do. Then she asked me how often I jerk off. I don't think I was really serious when I said this but I blurted out and asked her how much she would want to give me a hand job. She laughed but then to my suprise said "at least 30 bucks". That is how it started and since then every Thursday Sheila jerks me off. She has gotten to where she teases me with it holding my balls and stopping and starting over. I asked her if she does it for her husband and she says hardly ever. I pay her $50 each week and Thursdays are my favorite day. Its worth every cent just the way she plays with my genitals and takes her time having me ejaculate.
I'm into ladies lingerie and I live in a motel so we have a maid that comes once a week to clean our rooms. I started leaving my silky brief panties draped over the shower curtain rod along with control panties, pantyhose or thigh high stockings, half slips and even bras. She would look at me sort of weird and then I met her at the door wearing my red tights under a pair of shorts and a nylon tee shirt that couldn't begin to hide the outline of my bra. She stared at me smiling, and then went to work. Then I asked her if it bothered her that I wore women's underwear in front of her. She told me if you like wearing them I don't mind. Finally I asked if she would like to see me dressed up in all my lingerie, and she said yes. I told her to come by when she was done working. She did as I requested and now several times a week she comes by so I can model women's underwear for her. She loves feeling all my silky things and gives me hand jobs thru my panties.
I love to wear panties . My wife let's me