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Toyboy Warehouse - Why I'll Never Date a Younger Woman Again

Why I’ll Never Date Younger Women Again


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It was my first date with an older woman and I was bricking it. I could feel beads of sweat forming at my temples as I waited at our table and I looked around the restaurant nervously trying to see if I could recognise her coming in.

My thoughts got really loud: What if she’d been in already, seen me and left? What if she wasn’t the same woman in her photos? My stomach was a mess so I couldn’t even imagine ordering food, how was this date going to go down? This might seem normal for a sensitive, quiet kind of guy, but usually I’m quite confident so this unfamiliar feeling threw me even more.

“George?” I looked up and she was looking down at me. Pamela’s 48, 20 years older than the last woman I dated, and my breath caught in my chest when I looked at her. 5”9 with all the right curves and legs that go on forever, she was the type of woman all my mates would have admired in the pub but never dared speak to.

“Pam – hi,” I got up and went to kiss her on the cheek, but missed slightly planting my lips near her ear.

She chuckled a little and then sat in the chair I held out for her.

“So, urh, the weather is pretty shit isn’t it? I’ve been walking my mate’s dog today and he wasn’t liking it one bit.” Oh man, what was I saying? I was being boring and my mate doesn’t even have a dog.

Smiling, she reached out and touched my hand, “George, you look a bit nervous, don’t be.”

This is perhaps the least manly thing I’ve ever said but I’m sure my heart fluttered when she touched me. But I seemed to relax after that. Conversation flowed so much more easily, we seemed to talk really naturally but not about anything in particular.

The night flew by, I didn’t even notice but before I knew it we were finishing pudding and leaving to go to a bar. She ordered a long island ice tea, her fourth alcoholic drink this evening but she didn’t seem to lose her composure at all. I remembered a time my ex had had three cocktails and then fallen off her chair at the bar, not sexy.

A little later we stepped outside for a cigarette. She was making lots of eye contact with me, teasing me, batting her long eyelashes and shaking her hair in this really sexy way. Suddenly my confidence came back and I leaned in and kissed her. She kissed me back but just for a second – the look in her eyes told me that was all I was getting for now.

Soon I was putting her into a taxi and I couldn’t believe the night was over already. When would I see her again? Did she like me as much as I liked her? Just as she was about to close the door, she grabbed me by the tie and pulled me into the taxi with her. She planted a kiss directly on my lips and told the driver where to take us.

After twenty minutes the taxi arrived outside a set of very expensive looking apartments. I followed her up the stairs, unable to believe I was getting this far with her. Before we went inside, she pushed me up against the door and kissed me in a way no younger woman ever had. It was hot, the kind of hot my mates and I would share tales about, but this was different because I knew talking about this moment wouldn’t be as good as it felt right now.

She made me wait outside for five minutes and I started to feel a little confused. What was she doing in there? Should I go in yet? After five minutes I entered and could see a trail of her clothes leading the way into the bedroom. I heard her call my name from the direction they were leading and I strode in to see what was waiting for me. She looked so sexy, not wearing anything, lying on her bed. I couldn’t believe my luck.

What happened that night? A gentleman never tells. But I won’t be dating girls my own age anymore.

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