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This is a question Cougars and Sugar Daddies

Tell us your stories of age gap shags. No paedo gags please.

Inspired by The Resident Loon

(, Thu 4 Dec 2008, 13:55)
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This should have been
in last week's "cringe" QoTW as it makes me cringe now to think of it more than any of my responses to that question...

Anyway.

Getting married far too young - at my graduation I was the only one with baby buggy in tow - meant that post the inevitable quick separation, I tended to go for older women. Women in their early 20s and I had nothing in common, or so it seemed.

Several years after graduating, in my second job, I was unhappily living with someone around 8 years older than me. But the story isn't about her.

Two years into the job I had at the time, a new colleague came to join the small office I worked in. She was a good 20 years older than me, and she was Not A Looker. At all. She wasn't fat, but she was:

- short;
- a redhead, but not in the "flowing auburn locks" way but more like a Chuckle Brother or a Chuckie doll;
- wearing thick bottle-topped glasses;
- with copious lines on her face - it could have doubled as a contour map of a particularly steep hill;
- with a personality best described as "strange".

We worked together for a small charity. One year, we got a free stand at the Boat Show at Earls Court. We had a rota system for covering the stand between the handful of staff we could spare. Because of the distance between where we worked and London, we were put up in a hotel.

In my defence, I blame this on my boss. Both I and my female colleague - let's call her Andrea, for the sake of argument - were "covering" on the Sunday. So we were to stay at the hotel on the Saturday night.

Previously, my male boss and another employee, also male, had been sharing the same twin-bedded room. Somehow, this was meant to be acceptable for me (male) and Andrea to share.

Yes, you can guess what happened. Oh dear oh dear oh dear. My defence is / was not much sexual experience, alcohol, a brazen and successful attempt by Andrea to seduce me, and going through a bad patch (sleeping on a friend's sofa) with the on/off girlfriend at the time.

But that's not the cringe-worthy bit. Enough that I slept with one of the extras off Lord of the Rings, but worse was that I:

- repeated the performance sober at her house some days later;
- then got her to drive me the 50 miles or so to where my girlfriend lived so I could get back with her.

Lord, forgive me for this and please God don't let my current girlfriend, soon to be wife (this Saturday, dudes !) read this.

Funnily enough, whenever in the past I have added up my "shags", I always forget to add Andrea to the list.

The shame - the horror.
(, Thu 4 Dec 2008, 16:21, Reply)

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