A Riding Crop On The First Date

The subject of how you tell that new person in your life that you’d like to spank them keeps coming up. Getting the timing right and doing it smoothly are not easy. Here’s another how-not-to-do-it anecdote for you. Talking about your toys on the first date, out of the blue? Efficient perhaps, but neither suave nor debonair. From Falafel Sex:

As we drive I find myself learning all about his riding crop that his previous “ladyfriend” had given him.

Me: Riding crop? Do you own a horse?

The Date: Grin… “No.”

Ohhhh kay.

Dude, what where you thinking?

  1. spankmewithaspoon commented on March 10th, 2005:

    I guess here in the city, where we are so terminaly fashionable, we do handle everything in a New York minute. Here is a pickup conversation which took place at 8;30 AM, dog walking. I ran into a guy I had met previously in a bar, but he hadn’t phoned. Months later …….
    Him: Sorry I never called. I’ve been so busy with school. In May, I get my Masters Degree.
    Me: Oh! So then you’ll be a master ? Do you want a slave?
    Him: Sure!
    Me: Are you into spanking?
    Him: Yessssss…. And I’ve got a flat screen and Teevo
    Me: Great! I’ve got a camcorder
    Truly, I think he’s taken. But I offer this as an example of how a simple conversation can go harmlessly spanko, with a little practice.

  2. Ken commented on March 10th, 2005:

    True. It’s much better to spend weeks trying to get to know someone and keeping all your desires a secret only to find out after 6 months that the two of you had no chance of entering the kind of sexual relationship you were looking for in the first place.

    I’m so glad my wife read the porn stories I wrote before we began dating. It saved so much time.

  3. SpankBoss commented on March 10th, 2005:

    Uh, waiting for six month might be going too far in the other direction….

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