Great story and I'd love to read more.
I have a few that I'll write up when I get a chance. One involves a lady that was probably 15 years older than me (me being 18, at the time). She worked at a big retailer and was friends with a mutual group that I occasionally hung out with. She slipped me her phone number while we were at a group gathering (she was with a date), and we had quite a bit of fun together. One very interesting time was getting a hand job under a crocheted blanket while her teen daughter (she had her driver's license, so she was 16 or 17) sat across the living room from us. The mother slowly jacked me like nothing was going on, but the daughter had to know what was going on. I'll type up a more complete story later, but things ended when the mother wanted to get really serious...which was completely ridiculous and I'm glad I didn't go along with that.
Another was a lady (20+ years older than me) that worked at the same company my father did. I worked there during the summers (the company would temporarily hire employee's college-age kids), and I somehow learned about a lady that was having an affair with a permanent employee. For some crazy reason (ok... I was a horny kid), I started flirting with the lady, and she eventually came by my apartment to help me decorate or something like that. I ended up fingering and going down on her that visit, and that started a few times a week visit from her that lasted 6 months. She was a shift worker and would come by my apartment before going home. At that point in my life, I could last a long time, and I would do my best to wear her out :-). There was 0% chance that she would become pregnant, and I completely enjoyed every minute of my time with her. I'm putting this here so that I remember to write about it (if anyone is interested)... My mother was mad at me for something and came to my apartment to give me grief. My mother had a key and walked in on me balls deep in my friend (closer to my mom's age than me). It was a one-bedroom apartment, and I lived by myself, so the bedroom door was wide open. My friend was semi-out of her mind from fucking, and I was just climaxing as my mom spoke up. I half came in my friend and half on her spread eagle pussy as I was pulling out (with no idea who was behind me). My mom gave no ground and got to see her baby boy's cum covered cock and some lady's cum covered pussy spread eagle on the bed. It seemed like it took my friend 30 seconds to realize I had stopped and drop her legs. My mom never said a word about it, and my friend was afraid to leave my room (LOL).
For some reason, neither lady enjoyed giving a blow job, and they were both reluctant for me to go down on them initially. Maybe it was their age (this all took place in the early 90s) or some type of stigma they had, but they were both fit and nothing that they should have been concerned about. They both could come multiple times when I went down on them, so they certainly enjoyed it as part of our normal routine.
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