My first time with a man, when I was over 50

My sex with a man – the first time.


It had been a long week of sales calls, it was Thursday night and one more day to go before heading home.

I had taken a hotel in the middle of the city, most central to my customers, on a quiet side street.

For years, when travelling alone, I’ve had a little private ceremony, celebrating myself. Tonight I needed a pick up before venturing out for dinner.

My trusty dildo was in the bag. I rinsed my rear with my water bulb, lubed myself and proceeded to have anal sex, all on my own.

This little procedure had, with time, almost become a routine. I was a married man and never sought sex with any other women for my entire married life. But wanking off with a dildo inside me felt good and seemed totally harmless.

Eating in the hotel was not on my agenda. Unfortunately, many hotel dining rooms are either outrageously expensive, or serve awfully mediocre food, or sometimes both.

“Where is the nearest restaurant?”

“One half block down the street.”

That sounded convenient and off I went. Sure enough there it was. The menu displayed outside seemed varied and reasonably priced. I stepped in.

There was an armed guard standing just inside the door. Oops, this must be a really dangerous area of town. I feel safe to be here, not that I have ever thought about dining under the eyes of a man with a gun before.

The place was near full. I was offered to sit with two ladies.

“Sure, come sit with us.”

We had an amicable discussion about this and that and then we moved on to relationships.