As long as I can remember, I've been attracted to older women. So, on a recent trip to Florida, I had the fortune of visiting a hotel lounge, right on the beach, which had a live band. (They were all in their 70's with bad toupees and rumpled tuxedos.)
My friend Larry, who I was staying with, had plans for the night, and the lounge was within walking distance of his place, so no worries about driving. He said the place was nice, though an older crowd for us, both being 40, which was right up my alley.
I strolled in around 10pm, the band was trying to play something current, botching up the words and rhythm, and the square bar along the back window looked out on the ocean. I ordered a beer and took in the view, then scanned the bar, seeing a good sized crowd of men and women, ranging from my age into their 70's, laughing, flirting, generally acting like all horny people of any age group.
Across the bar sat 2 women, a blond and a redhead, both women done to the nines, with their jewelry and hair perfect, both attractive and about 55 I guessed. They both looked away when I met their eyes, whispering to each other like school girls, caught gawking at a new teacher.
Even though they were 15 years older, it felt good to know I intrigued them, and I made a note of it as I looked over the rest of the place.
After a minute, I looked across and found my admirers were gone. I ordered another beer and turned to look at the moonlight on the ocean, and there, at the glass, were my lady friends, not 10 feet away, glancing at me, and out the window.
I'm not a smooth person, and tried to think of the right opening line. The blond smiled at me and said "Did you lose Grandpa again?"
"Huh?" They both chuckled. Red said, "Aren't you a little young for this crowd?"
"I don't know, are you gonna proof me?" I laughed.
We began chatting. Red's name was Liz and Blondie was Sue. On closer look, they were both closer to 60, and I'm sure both were knockouts in their younger days, and while Blondie was trimmer, Red had a set of tits that just begged to be sucked. Both stood about 5'7, but I'm not sure how much of that was real or heel.
People were dancing and a slow song came on, and Red asked me to dance. Why not? She moved into me, her soft breasts pressed into my chest, and she moaned, softly. "Mmmm, you remind me of someone I knew long ago."
"Is that good or bad?" I asked.
"Good, very good." Her arms tightened around my neck, and her perfume was not overpowering, but definitely strong! It reminded me of my youth, when older ladies always wore perfume, and I felt a stirring in my pants, and it felt good.
After the song ended, we held on a little longer, she looked up and said "Thank you".
"My pleasure," I said, wondering if I was a novelty or someone of interest to her. I felt other women her age, looking at us. Red was apparently a regular here.
I thought she was gonna kiss me, but she hesitated and the moment passed. Back at the bar, Sue was talking to another guy, their age. She introduced me. Liz knew him too and they kissed and exchanged pleasantries.
"Bob is heading up to Lauderdale to see Jim, wanna come?" Red looked at me, then back and said, "I don't think so, if Harry doesn't mind my company, I'd just as soon stay local"
I wasn't going anywhere, so we agreed. Sue said she'd leave her car for Liz to get home, and after a big hug and kiss on the cheek, they left us sipping drinks, me with a half a hard-on, smiling at each other.
They wound up being room-mates, sharing a condo on the beach half a mile away. From what I could gather, they both had no financial worries, traveling often, eating in fine restaurants. The night wore on and she asked if my friend Larry would be waiting up for me, which I laughed at, and she blushed a bit and said "Well, the moon looks fantastic from our balcony."
I smiled and said "I'd really like to see that"
"Would you? Good, fine, we can go back for a quick tour, and have you back in plenty of time." It was 2 hours to closing.
