I'll start by saying this has nothing to do with my mom, so if you're looking for something more Oedipus-sy, I wish you the best of luck. This is a quick story about my experience with an older woman.
My mom and Jenna met each other in the hospital while they were giving birth; mom was having my little sister and Jenna was having her first of three children. Despite the age difference - mom was in her early 30s and Jenna was barely 20 - they quickly became good friends, eventually becoming great friends. Jenna and her husband, Rick, became part of our family. Like an aunt and uncle, without any of the blood relations.
We lived in a small town and tended to do things together. Movie nights, BBQs, camping, and even holidays. One of my earliest sexy memories of Jenna was while we were in Mexico at one of those all-inclusive resorts. She'd had a couple of years to get her pre-baby figure back, and she looked amazing. The two of us were at the pool because the rest of our families had taken the ferry to Cozumel. I used to get terrible sea-sickness and Jenna wanted to lay by the pool and soak up the sun, so she suggested the two of us hang out while the rest of the family explored the little island. I had my books and she had a few margaritas. It was looking like it was going to be a very good day.
Being that I was a late bloomer, I'd seen a few of my dad's stroke books and had a basic idea about sex, but I wasn't particularly sexually aware. I was 18, but the hormones hadn't quite kicked in yet.
I guess a bit about Jenna would be appropriate here - back then, she was an Italian goddess. Olive skin, hair so dark brown it was almost black, and a dedication to exercise combined with a superb metabolism had resulted in a near-perfect body. This was in the era of jazzercise and aerobics, so she didn't have rock-hard abs and buns of steel, rather, soft curves and a toned body. The white bikini she wore showed off her supple skin and fantastic figure. I'm in my 50s now, and still can't recall a body that amazing.
Jenna and I had been in and out of the pool for most of the afternoon, horsing around. We'd been playing water-basketball and there were a few times where I accidentally bumped her while trying to block a shot, or she'd do the same to me. Nothing major, but a young guy isn't going to forget the first time a strange boob brushes against his arm - hell, any contact with the opposite sex was memorable. Eventually we got out and after a quick bite decided to sit and enjoy the sun for a while. My mom was paranoid about skin cancer, so I was well trained at making sure I was slathered in sunscreen regularly. I covered my arms, neck, chest, and legs before awkwardly trying to cover my back. That's when Jenna took the bottle from me and rubbed it into my skin. It was amazing. The touch of her hands on my skin...exquisite. And then to make matters worse, she proceeded to squeeze out more lotion to ensure she was adequately covered.
She poured the lotion into her hands and began applying it to her long, luscious legs. She bent over to reach her shins and calves, giving me an incredible view of her more-than-ample cleavage as it strained against the flimsy material of her bikini top. As she moved up her legs, she gave me a polite smile as she caught me staring at her. I blushed and looked away, only to see that pretty much every guy on the pool deck was straining to watch her put on the sunscreen. Some of them were trying to be discreet, watching out of the corner of their eye to avoid confrontation with their wives, while others were openly ogling her. I laughed and tried hard not to look at her again, but apparently my hormones had finally kicked in and I soon found myself watching as her hands crossed her tight tummy and made their way to the land of underboob. She had her eyes closed as she applied the lotion, covering her body with the invisible sun barrier. Her hands moved with the natural motions that come from doing a task numerous times, and before long she was rubbing the last of the lotion into her face, smiling at me while she did it. With a bit of lotion on her finger, she tapped me on the nose to break me out of my trance.
"Would you mind putting some on my back for me?"
I knew she asked me, but it was funny to see four of the guys closest to us to jump out of their seats. Apparently everyone is a gentleman.
Jenna moved the lounge chair into the reclined position, and then turned over to give me access to her back. She jumped a bit when I squirted the cool lotion directly onto her back, but soon relaxed and let me caress her skin with my inexperienced hands. As I moved up to the strap of her bikini, she reached behind and undid the bow.
"I'll just undo this so I don't get any tan lines,' she said.
I certainly wasn't going to argue, so I continued to apply the sunscreen, enjoying my first experience of touching an actual woman. By the time I was done, I had a major tent pole situation and no clue what to do with it or how to hide it. I grabbed my book and smashed it against my swim trunks, painfully subduing the growing monster in my shorts, then excused myself to go back to my room. Jenna lazily nodded to me before drifting off to sleep in the hot sun. And that was the day I learned about the joy of masturbation, and to this day I will occasionally dip into that memory for inspiration.
It must have been a great trip for Jenna and Rick as well, as about nine months later their daughter was born.
