I’ve had a couple of stinker ONS episodes over the years and one AP who I had awesome chemistry and banter with but the moment we ended up in a situation where our clothes got discarded it just went south.

The absolute worst episode though was with an AP that I’d met through a service. There used to be an executive dating service in my city where they would “match” you with like minded married people for “discrete” encounters. I’d read about it in an article, I was between APs, so I contacted them.

I met a couple of women socially through them that were “matched” with me, but despite being attractive, there wasn’t really much chemistry - sometimes me, sometimes them.

I met one woman who I saw for about six months but then her husband’s deployment (he was in his countries ambassadorial corp) ended and she went back home.

I then was matched with this other lady, we’ll call her Elizabeth. She was utterly stunning. I’m not going to lie, I’m a 6 or a 7 on a good day, but Elizabeth was an 11. We’re talking model good looks and a body that was head turning.

I met her for drinks and immediately thought, “No shot, Bucko. She’s so far out of your league, you’ve got no chance. Pay for her wine, thank her for meeting you, and wish her luck.”

Anyway, one wine turned into two and we spent the whole afternoon laughing. When she contacted me the next day to say she’d love to catch up again for something more intimate, I’d felt like I’d charmed her pants off more than anything else.

Her husband was a Diamond importer. She didn’t say blood diamonds, but that’s probably what was going on. As a result, I was a bit uneasy because shagging the wife of someone in a business like that can be quite messy.

Anyway, she assured me it was all good, he was a fair bit older than her and she said that their sex life was non-existent because he was bisexual and leaned more towards younger men.

Fair enough.

We met up, got to the fun part of the meeting and her body was terrific… but sexually, it was absolutely horrible. LOL.

She was VERY restrained, laid there, didn’t move a lot or make any sound at all. I put in a serious effort to get her over the line once or twice to try and loosen her up and her orgasm sounded like she had the sniffles. Hahaha.

I then moved on and she told me that she was not on birth control and so she requested me to double bag myself. Sex consisted of missionary and her closing her eyes, turning her head, and seemingly holding her breath.

Amongst this, I managed to finish. LOL.

She asked me if I was “good” and when I said, “Yeah” she hopped up and went to have a shower.

It was terrible sex. Hahaha.

So of course, when she contacted me a couple weeks later to catch up, I said, “Sounds awesome!”

Same routine again. Probably worse because I could see what was coming.

Third time’s a charm? Nope.

That third time, I literally faked an orgasm to end it. That was a first.

When she contacted me again a few weeks later, I told her that it wasn’t working for me. She asked to meet for a drink to talk and so I figured I owed her that much. I have a rule about “if my penis was inside you, I owe you certain courtesies”.

She asked what had changed and I said that I just felt that it was great fun but that I didn’t think the chemistry was there. She seemed surprised and told me how much she’d physically enjoyed herself.

It was such an awkward conversation but despite her trying a few more times, I refused to relent because I knew it was never going to improve.

Easily, easily, the worst affair sex I’ve ever had outside of a bad singular outing here and there - it was just consistently not great!