Sweet Weekend With My Boy

I just had a lovely weekend with my sweet boy. Yes, there was kink and debauchery, but there was also a lot of binge watching of television shows. We’re watching Atlanta right now, in which I see elements of Louie and Girls. There was also a lot of soaking up the lovely late summer weather and reading. And talking politics and silliness.

As for the debauchery, right now we are very focused on orgasm control—-his. He basically keeps himself in chastity until we see each other, and then I stretch it out until he’s going insane. It’s fun, and I admit I feel a little sad when I finally let him come. He’s incredibly eager and totally focused on me when he’s desperate, which is adorable. And I love attention! But it does get to a point where he’s aching or soooo eager that any little thing will send him over the edge. And then I usually take pity. Sometimes I think he might not want me to, though. It’s something I have to think about. Would I see him and deny him the whole time? I think it’s something he would find both exciting and scary.

We also played with some crossdressing again, which is something we haven’t done in a very long time. It was initially a fantasy of his that I tried, but I was surprised that I liked it as much as I did. But we really haven’t done much with it over a year and a half. I think it was my latest story that put it back in my mind, so I dressed him up in one of my very tight vinyl skirts and a push up bra and a wig and lipstick and had my way with him.

From the front, he still looks mostly like a man. It would take more makeup and a better wig to make a dent in that. But from the back, he looks quite feminine, and I find it sexy. This is interesting to me, because I don’t think of myself as bisexual. Still, I KNOW he IS a man. It’s not really that I don’t find women beautiful. I find many more women attractive than men. It’s just that I don’t really know what to DO with women–how to hold them, tease them, seduce them. Men are very simple, and I have had a lifetime of practice with them. Women are all very different and complex.

I really like clutching him in my vinyl skirt. I hadn’t realized before just how good gripping that fabric and the flesh that lies under it feels.

I also like being called daddy. 😉 Who knew?

1 thought on “Sweet Weekend With My Boy

  1. It’s interesting to hear it from the woman’s perspective. I’m learning to be more comfortable with this side of me and I’ve always struggled to understand why everyone else doesn’t view it with a sense of humiliation and shame like I do. Insights like this are helpful in letting me break through some of those internal barriers.

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