Emily – The Proposition

See: Emily – Pretend Sugarbaby

A lot’s changed in my life. After a couple of years with Cherie, that relationship is now ashes.

Rebecca’s back and I’ll have to see how that plays out. Kita has entered the arena of my exploits. Things are good. Things are changing, but it all seems for the best. I’m off on Sundays and Mondays now and I like that. Monday is always the opposite of what it once was in my former corporate life.

Sunday you started having thoughts of going back to the office Monday morning, and living through the meetings, the sales goals, the shitty managers, etc. Now I do what I want on Sunday, and sleep in on Monday. I go to Cavanaugh’s for the 1/2 off cheese steak and edit my blogs for the week. I like the food, the service, and the routine.

I don’t need much time off. So although I’ve got it all set up for Monday, I don’t know what to do with myself on Sundays now. I take myself out to breakfast, wander the city, run errands, and go to the movies.

Most of my young friends are married or live far away. Church is off in his own world working. Johnny is wrapped up in his life up in Mayfair, and my friend Rob is working in Zurich for two years with his wife and son.

I’m not ready to get into another relationship after sort of being in one with Cherie. It’s simply too challenging for me to be that attentive to what most (All) women want. I wish I had a young, attractive easy going girl I could spend a few hours with on a Sunday, maybe once or twice a month. That’s about all I could handle.

We hang out. Eat, drink, go to a museum or a movie and then she leaves and I get to enjoy my night in happy solitude.

Then it hit me.

Reach out to little Emily.

But not to catch up and have a drink. She’s 24 and I’m 57. We have nothing in common.

I’ve decided to set up a meeting. I’ll take her some place nice. Like Gran Caffe L’aquilla, she loved the calamari, cocktails and especially their award-winning gelato.

If she’s available she won’t turn down going there. She never goes to places like that because she can’t afford it.

When we get there, we’ll catch up and then after a few drinks I’ll ask her. I’ll gently explain what my situation and ask her if once or twice a month, if she’d like to hang out for a couple of hours on a Sunday, and I pay for everything.

I’ll tell her it’s strictly platonic and I just want the company of a young woman for a few hours on a Sunday.

I’m going to try this out on her because I have nothing to lose. But the more I thought about it, I realized I knew several women I could use this on.

I’m going to make a list and see if this honest approach works.

Wish me luck!

(Of course when all of this quarantine stuff is over!)


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Author: phicklephilly

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3 thoughts on “Emily – The Proposition”

  1. Good luck! You are charming enough to achieve whatever you want in this arena. Although, as you’ve discovered, the more you don’t push, the more women throw themselves at you. Maybe you’ll be going hot and heavy with Emily at Mac Mart, lol! I find it so funny if we are representative of middle age men and women. You’re cool with no sex, and that is my main goal, and I will add on a friendship if I have to, to get what I want. Ha ha! Lordy the men I’ve met like to talk! I find myself listening patiently and waiting until they feel heard enough that I can jump their bones! It’s all so fascinating.

    1. I’ve been kicking this idea for awhile. I appreciate your compliments, Sandy! I like that we almost have opposite approaches to relationships. Me, i love the thrust and parry of courtship, dating, and romance. I know eventually the physical aspects of the relationship will eventually present themselves to me because I’m patient and love dating and the company of women. I do the thing most men have no interest in. I’ve been fortunate. You, on the other hand, work it the other way… “When is this guy going to stop talking so we can get to the fun stuff?” I love it!

      Quick question… Should I continue to schedule the Rebecca and Kita stories or wait until all of this quarantine stuff blows over? My gut is telling me to keep the content rolling through this to keep the party going. Thoughts?

      As always, thanks so much for your support, love! – Charles

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