I’d have to say the most taboo, for want of a better word, sexual experience I’ve had happened when I was 29. It was part of a double header (quite literally) one summer weekend in 2010.

I use the word taboo because the first part of this double header involves a woman that was not only 26 years older than me, but we were also related. In a way.

To be clear, she was not a blood relative or anything. Nothing that took place was i****tuous or i*****l. But it was definitely irregular and I’m pretty sure that if anyone in my family had found out, it would not have gone down well! Unlike her…

Her name was Helen and she was 55. And I’m using the past tense because, sadly, Helen is no longer with us. How we were related is complicated and involves second marriages and separate connections to both of my parents. I’m not even sure exactly what relation she was because it was quite a unique and obscure situation, but the relationship was always a kind of auntie / nephew one – even though that isn’t strictly accurate.

She liked the atmosphere and people in my local pub and used to come over every couple of months for a night out, and would often spend the night at my place. Nothing remotely intimate had ever happened before, and the thought of it had never crossed my mind. Why would it? She was my (not) auntie!

Then one night that all changed. We were back at my place after closing time, having a few nightcaps, and for the first time ever I also asked her if she wanted to join me in a smoke. I knew she was a bit of a hippy back in the 70’s and would probably be up for it. Which she was. I suppose Helen was quite attractive and looked good for her age. She was quite fashionable, looked after herself, and had long blonde hair and decent looking figure, although she was probably a bit too thin if anything.

It must have been the combination of alcohol and weed that turned the conversation sexual, and she was quizzing me about why I didn’t have a serious girlfriend and wasn’t I fed up of ‘playing the field’. “Doesn’t a nice looking young man like you want to settle down” etc. etc. Then she got a bit more full on and starting asking me about how many women I’d been with and what sort of experiences I had had. I told her about a few of them, including the one almost 2 years before with Tracey over the road, who was 17 years older than me (see ‘The Older Women Experience’ story for further details!).

This one in particular seemed to pique her interest and she asked me if I had a thing for older women, and if a 17 year gap wasn’t an issue for me, how much more of a gap would be too much? I now had the feeling this was going somewhere a bit weird, but that alcohol and weed combination was blocking any normal impulse to resist. And when she put her arm around me and pulled me in to kiss me, I didn’t pull away.