How it should have happened

This is neither entirely fact nor entirely fiction. It’s more a re-imagining of a real event as it would have gone if circumstances had been a bit different.

One day I found myself in a rich part of Sydney with my friend and his younger sister doing some shopping for a special occasion that evening. It was still kind of cold so I was wearing jeans and a pair of boots, but I had driven in from out of town and when I go on long drives I always prefer to wear a loose singlet which shows off a bit of my body but still leaves something to the imagination. We entered the supermarket and I immediately found my eyes drawn to a woman who appeared to be in her early forties. She was a bit shorter than me despite the heels she was wearing along with a pair of tight jeans and a tight white long-sleeve top. The outfit flattered her perfectly and brought out an ass that looked like it belonged on an eighteen year-old and a pair of tits that even from the rearward angle made me suspect that she knew a few good plastic surgeons. Not that I was complaining. I’ve never been one for subtlety and my gaze lingered a bit longer than it should have, such that when she turned around from the shelf I found myself caught in a bit of a stare with her. I flashed the usual cocky smile I have for getting me out of such situations and carried on with the shopping, moving to another aisle. As I picked up a few items and moved into the next aisle, I found myself once again walking towards her while trying to make conversation with my friend. I kept my gaze separate this time, and only briefly flicked my eyes towards her as we were about to pass one another. She had been staring at me the whole way down the aisle and now flashed me a cheeky smile of her own. My friend and I started to have a bit of a laugh as I had a reputation for unintentionally drawing in older women, but we went about our business. The pattern repeated itself another four times: seemingly innocently passing one another with a few quick flashes of acknowledgement that somehow got me thinking dirty thoughts. We reached the end of the shopping and I realised I needed to pick up a bottle of wine for the function that night, but I stopped in my tracks when I realised she was checking out the wine as well. With a brief, nervous glance at my friend, I strode over and started looking. I hate when women are presumptuous about their looks, and I was over there with completely innocent intentions, so at first I made a conscious effort to completely ignore her, even though she seemed to clear her throat a couple of times. Not being particularly strong at choosing wine, I caved in with the best of intentions.
“Excuse me? Sorry, but you look like you have a much better idea what you’re doing here than I do.” I said with a slight chuckle at the awkwardness of the situation.
“How’s that?” She replied coyly, turning slightly to face me as she held a bottle in one hand.
“I’m clueless when it comes to wine, as much as I do enjoy it. Any chance you can help me pick something out to impress my mate’s parents tonight?”
“Hmm” she exaggerated the noise slightly and leaned in close to me, looking up as she drew another bottle out from the shelf. “Right under your nose. This’ll go down a treat and you can hold me personally responsible if it doesn’t.” She was facing me frontally now, standing with a playful posture and holding the two bottles up so I could clearly see her knuckles: no wedding ring. I let out another slightly nervous laugh and took the bottle she was offering me, returning her piercing gaze.
“Maybe you’d better share a bottle with me first, just to make sure it’s ok” I took a break to check out the label, her stare was doing some funny things to me.
“That sounds like a great idea”.

This is how things actually went:
“Thanks. Sorry but I really need to get going” I remarked and walked away to rejoin my friend.

This is how it would have gone if I’d felt up to it:
“Tell me where to be and when.” We exchanged phone numbers and addresses and I went back to my friend. We both went through different checkouts at the same time, and I could see her staring at me. The stare had gotten dirtier each time we’d passed each other, but now she knew that she almost had me. I turned to my friend.
“I need to call in a favour. I’ll be late and possibly mauled.” He laughed, took the shopping from me and offered to walk home with his sister since it was close. “I love you, man.” I laughed and shook my head as I walked out of the supermarket to drive to her place.

I pulled up at her house as a young guy dressed in footy gear got into his car and sped off, probably to training. I knocked on the door and she answered, grinning and holding up a bottle of the wine she had recommended.
“Did I scare someone off?” I asked, innocently hiding the dig for information.
“Just my son, he’ll be gone all night” Her response had me high-fiving myself on the inside. She led me through into a richly appointed living room, sat me down on a sofa and walked off to open the bottle, her heels clacking on the tiled floor. She returned with two huge glasses of red, and I could see from the increased depth of her cleavage that she had tried to pull her shirt tighter since I had first seen her. We made small-talk for the next couple of hours and found our way through the bottle leading to a pleasant buzz. She had shifted herself closer and closer to me on the couch when she became more impressed by certain truths I would reveal to her. It turned out that she was in fact the ex-wife of a plastic surgeon, although she was trying to convince me that her tits were real.
“Really, go on and touch them!” She giggled, placing her glass on the coffee table and turning towards me with her hands on her lap in a way that pushed her tits tighter together. I let out a bit of a laugh but thought about it: they were very inviting.
“Oh come on, I’m too much of a gentleman to go straight to second base without –“ She grabbed my head and pulled me in for a long kiss, balling up a fistful of my hair as she did so. It was the most amazing kiss: our breathing stepping up in rhythm and her tongue lashing around just right, with the sort of enthusiasm of one who wanted to be a teenager again. I realised that I’d placed a hand up around her neck, matching her passion. When we broke, she guided one of my hands down to her tits. Through the shirt and what was obviously a nice lacy bra, I could feel the perfect mix of ripe firmness and natural softness as she stared into my eyes, her forehead against mine, and bit her lip.
“I’ll show you mine if you show me yours” she teased, lifting my singlet over my head and running a hand down my toned chest. I kissed her again as she continued to fondle me, and started to pay a bit of attention to her neck. First a peck, then a longer kiss, then a gentle bite which saw her let out a sigh and glide a hand down over my crotch.
“Not yet” I decided to tease her back, lifting the hand off my bulging pants. She leaned back, pouting, and lifted her top off, showing a stomach miraculously toned for a woman her age. I shook my head and smiled, amazed.
“Now?” She asked, leaning back, swaying her chest seductively and staring into my eyes.
“Hmm nope, not quite” my eyes darted back to her breasts. The bra wasn’t even a push-up, they were just amazing. She brought her knees up onto the couch and put her head against mine again, pressing her chest into my side. I wrapped an arm around her, enjoying the heat of our flesh pressing together, sharply rolling her down onto my lap and leaned in for another kiss as she started to giggle. She drank it in for a few moments, each kiss as amazing as the last, before she playfully pushed my head up. She rolled back up onto her knees, tracing a hand down my abs while I reached behind her and unclasped the bra. It came loose and she let it fall to the couch, revealing the most perfect nipples I had ever seen, but no scars.
“Ta-daaa” she sang as she returned her hands to my body and kissed me again. “How about now?” I playfully seemed to consider it for a moment, before she started unzipping my jeans. “Fuck it, this toyboy’s going to learn his place.”