When my parents divorced in high school, they both had remarried by the time I graduated. My new step mother came from a wealthy family in Northern California. She invited me and my sister to go stay with her and my dad at her mom’s (my new step grandma’s) house. I knew she was rich but I had no idea how rich. We arrived to a gated mansion with probably ten bedrooms and a half Olympic sized pool. This was gonna be a fun week.
She also had a maid that was there on week days. She was very pretty. Maybe 25. At 18 I was infatuated. So imagine my disappointment Saturday morning when the weekend maid showed up. She was Eastern European, mid 60s I’d assume, and fat. She had a thick accent. Not much to look at but she was quite nice. She made us lunch before we headed out to the pool for the day.
After I had had enough swimming I left my family at the pool and headed to a bathroom off the back of the house to shower. I exited wearing just my towel around my waist to find the elderly maid in the kitchen. She was carrying a hamper full of towels and spotted me. “I am cleaning towels, give me that towel”. I was a bit shocked. “I’m not wearing anything underneath”. She rolled her eyes. “Come now! I have seen penis before. Give!” I’m not sure why, but I became immediately aroused at the thought. I felt my cock stiffen a bit beneath the towel. So rather than refuse or hand it to her and cover up I unwrapped my body and let my cock hang in clear view. She glanced at my naked body and stared directly at my cock. She said “there now. That so embarrassing?” Before turning to head to the laundry room off the kitchen. As she exited she turned to me and opened the swinging door with her back and looked straight to my cock again. I was nearly fully erect. I retreated to the bedroom I had been assigned and promptly jerked off. I was so horny. I imagined her touching it. Helping me out.
It’s stuck with me as a massive fantasy. I spent all day Sunday trying to figure out how to recreate the event but there just wasn’t a way. I was in my rinks around her, my package bulging from the thoughts of the day before and she looked my way a few times but nothing happened of course.
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