Talk about pressure…
As if it’s not sometimes intimidating enough being a young guy attracted to (and always trying to impress) older women, Valentine’s Day can really ramp up the expectations.
If I want to get anywhere with her, I’m gonna have to pull out some big guns, the likes of which are often off limits to a young’un like moi: Valentine’s will be Visa ’n’ Vibrator night.
Pick Up. I’ll need new (re: expensive new) clothes for the restaurant I plan on taking her to. She’ll find me waiting outside her condo in the luxury car I’ve rented for the evening. I will have made the reservation on my own, as a surprise, but it’s for her fave restaurant, so already the bingos are adding up. We’ll look good and eat good food. She loves a well-planned date.
Dinner. By this point I’ve obviously abandoned all rational thought of paying off my credit card by Xmas, so after the amuse bouche we’ll be going balls-to-the-wall and getting right to the oysters. If she suggests a chateaubriand for two, who am I to refuse? When the waiter suggests the perfect red pairing, I’ll defer to her whims. Fuck, I’ll even stick around for the coffee.
Bedtime. And here I will control myself like never before, and indulge her in a way that requires not money but surrender. She loves to play with a vibrator when I’m not around (in fact, I get a little out of sorts when she “jokingly” refers to it as her BFF.) I’ll have her teach me how to use this toy on her, patiently, in all the ways that get her off. I’ll learn them, and repeat them throughout the night — without worrying about satisfying my own needs (which, I trust, deep down, she’ll decide to get to on her own if she has any Valentine’s heart at all.)
February 15th. After I’ve slipped away, post-morning toast ’n’ coffee in bed, I’ll call her, throughout the day, ask her how she’s feeling. Has she “recovered?” “How on earth can we top such an awesome night?” kinda thing. She’ll love it. And I’ll feel like I’ve actually done something for her for a change, instead of the other way around.
Then I’ll have to find a second job and wank like a monkey for a week.
How to Impress a Cougar to Get Laid
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