The Sex Files: ‘I Had Sex With An Older Guy’

Warning: NSFW content!

Every month, an anonymous STELLAR reader divulges their memories of the best (and sometimes worst) ride of their lives.

“Ray* and I had been together since we were teenagers. I was besotted with him but as we grew up we started drifting further apart.

After college it became blatantly obvious to me that we were on completely different wavelengths: Ray was still so immature; he loved the sesh and had no real ambition to make anything of himself and it infuriated me. The more childish he acted the more we’d bicker and eventually I decided we should call it a day.

Even though I was the one to break it off, I was heartbroken. I started going on wild nights
out, drinking a little too much and hooking up with guys around my age who proved to be just like my ex. I longed for someone a bit more mature, someone who had drive and ambition and could take the lead.

That person showed up in the most unlikely of places. It was summer and my parents were throwing a BBQ for some friends, family and neighbours so I trekked home from Dublin to Clare to be there. One of the first people to show up was John, a neighbour who had lived down the road from us for some time. I’d known John since childhood but hadn’t known too much about him other than the fact he’d made a fortune in property investments.

I’d never noticed how handsome he was before. He was in his late 40s but still had this boyish charm about him. His once dark hair now had streaks of grey through it, and he was dressed in a crisp white shirt and dark jeans.

As the night wore on I found myself gravitating towards John more and more, our conversations got more intimate, and eventually it was just the two of us sitting out on the couch on the patio, after everyone else had left and my parents had gone to bed. We had inched closer to each other on the couch and the sexual tension was palpable – so fuelled by six or seven glasses of Prosecco, I decided to just go for it.

I pulled John towards me and cupped his face in my hands, kissing him ever so so softly at first. I felt him kiss me back, running his hands through my hair and then we just kind of sunk into it. He pulled the dress I was wearing up, skillfully unhooked my bra and let his lips roam all over my body, planting kisses along my face, neck and boobs, and letting his fingers explore my clit. He knew exactly what he was doing

Next, John pulled me on top of him, so that my legs were straddling his waist, and then he was inside me. He placed both hands on my hips, and with a gentle but firm pressure controlled the motion of our bodies until we both worked our way to a climax. It was so passionate and intense, and there was just something so sexy about knowing he was so experienced.

John and I agreed that the sex would be just a one time thing. It would prove too messy given that he knows my parents, and I know that long term I want to be with someone closer to my own age, but I’ve no regrets. I think it’s important to have different sexual experiences with all different kinds of people, and that night with John is one that I’m in no hurry to forget.”

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