I was always pretty fond of older women. When I was 13, my “girlfriend” was 15. At 16 I lost my virginity to a 19-year-old. I always found the allure of someone more experienced in life to be exciting. Maybe I had some kind of complex that necessitated a dual role of lover/mother in my partners. In my later teen years, things moved beyond that to the outer realm of normality.

My grandparents had an apartment just south of Tampa. It was on a beach strip with nothing but condos and the occasional hotel, and the demographic was decidedly gray and withered. Aside from the occasional youngish retiree who patrolled the beach and grew red and lobstery, the rest of the population was chiefly concerned with playing bridge and getting the early bird special at the moderately swanky restaurant nearby.

The women in my grandparent’s building had always doted on me, ever since I was in diapers. I think they were starved for any kind of youth, so if you walked by a group of them sitting in the shade beside the pool, they’d collectively squeal with delight. The male to female ratio in elderly Florida would make a Jersey Orangino’s valhalla pale in comparison.

By the time my 17th birthday rolled around, my cherry was popped and my teenage libido was in maximum overdrive. My parents sent me down to visit my grandparents during spring break. Much to my initial dismay, spring break where they lived had little to do with keg stands and wet t-shirt contests. The tension of my teen loins was considerable, perhaps my excess energy was noticeable to others.

I dunno if she noticed me first, or if I noticed her first. I do remember the first time I saw her though. She was sitting in the lobby of my grandparents’ building, sipping a Long Island iced tea. Immediately my teen lust eyes were drawn to the cleavage she was sporting. Her skin looked smooth for an older woman, a couple veins showing, but nice. She looked to be about 70, a young 70. Her face had a considerable amount of makeup, but it was sorta tasteful, like Blanche from the Golden Girls.

I’d stopped dead in my tracks, she confidently locked eyes with me after looking me up and down. I nervously looked away and started for the door, but she called after me, “Hello, boy!” I walked over to where she was sitting, legs crossed, deep green eyes fixed on me as I tried to seem casual. “Say boy, I wanted to ask you a great favor.” She cooed more than she spoke, there was a hint of upper class New York in her speech. As I stood close to her, the wrinkles on her face were evident, but her personality shone through. She held up her empty glass and rattled the ice cubes at the bottom. “Do be a dear and fetch me another drink from the barman. Tell him Phyllis sent you.” Standing over her, my eyes darted to her full bosoms proudly displayed. I immediately regretted it as she noticed me noticing.

I dutifully brought her the drink. “For your troubles”, she said as she slipped a 20 dollar bill into my pocket. “Say, I’d like to take you out for dinner tonight, young man.” I stuttered and mumbled about how my grandparents might not approve. “Oh, surely they wouldn’t object to you giving a poor little lonely old lady like me a bit of company? Tell you what, which apartment are your folks in?” “803”. “Well, I’ll send up an invitation to 803 cordially inviting the young man who so graciously helped an elderly woman with her groceries to dinner.” I didn’t know what to say. She said in a voice that was almost comically sultry, “Meet me here at 8”.

She was waiting for me when I came out of the elevator. As I approached, she tossed e her keys and said, “You drive”. I had my learner’s permit, but I was a bit hesitant to sit behind the wheel of a Rolls Royce. The restaurant she took me to was overly lavish. I felt like a fish out of water trying to pronounce “coq au vin”. During dinner, Phyllis periodically and ever so slightly rubbed her foot along the inside of my leg underneath the table. She inquired about my life, dodging any questions I had about hers. The gap between our ages was vast, no question, but she seemed reasonably aware of what people my age were into.

After dinner, we walked to the car, her arm wrapped around mine. I think she noticed me stagger a bit from all the champagne at dinner since she didn’t offer me the keys this time. She drove fast. Not home to my grandparent’s building, but down a dark cul de sac surrounded by marshland. She turned off the ignition. Without hesitation, she turned to me and began unbuttoning my shirt. I let her. I sat motionless as she undressed me. Only the back of her head was visible in my lap. She didn’t take off her dress, just her panties and then deftly climbed onto me. My face was buried in her chest, I didn’t last long. Without ceremony, she dismounted and sat back in the drivers seat. I felt weird. She let out a deep sigh and started the car as I clamored to get my clothes back on. Not a word was spoken during the drive home and she let me out in front of the building with just a “Goodbye”.

I’m older now, married to a woman just three years my senior. I’ve never told her about Phyllis. I’ve been back to my grandparents’ place in Florida a few times since then, but I never saw her again after that night. The thought that she is either dead or in a nursing home somewhere is somewhat unnerving. I’d often wondered about what she had to gain from a romp with a jittery teenager, how many times she’d done it. Perhaps she was trying to relive her first time, the fountain of youth or some such nonsense. Wherever she is, I can’t help but feel that she is terribly, terribly alone.