Okay, I'll start things off. Since we don't have a name for our advice columnist yet I'll start it Dear X, but it could be Dear Abby, Dear Anne, etc.
I never thought I'd write a letter like this. I though I had my life together and on course, but damn it I need advice and I don't want to ask anyone face to face because they might think I'm sick or something.
This is something I've never ever told anyone. I have these dreams of being hauled over a boy's lap and spanked and spanked. Sometimes the dreams end with us screwing but most times it's just the spanking. And it's not a random boy and I know where the dreams come from.
Back when I was growing up I had a friend, I'll call her "Sally", and I was over at Sally's house a lot. More, much more, than any of her other friends. Some of her friends couldn't ever go over her to house at all. You see Sally had a brother who was five years older and he was always being be pressed into babysitting her and he had permission to spank her if she needed it. Of course he didn't have a blank cheque. If he used an instrument (his belt, her hairbrush, a wooden spoon, or anything thing else) he'd have to explain why when his folks got home or get the same instrument used on his butt. If he bared her butt then he'd have to explain that too, especially when she was getting older, so he didn't usually do that. But if he grabbed his sister, haul her over his knee, and gave her five or six hand spanks over her clothes, that was okay. Sally couldn't complain about that, not without getting more from her parents when they got home.
So that's what happen. He was always doing that. When I was there I had better than 50/50 chance of seeing him spank her - I know because at one point I made careful records when he did and didn't spank her. And while he couldn't bare her butt she used to wear skirts and dresses a lot and "it just happened" that her panties were at least partly exposed a lot of the time.
And after it happened he'd sometimes look at me (or any other friend she had there) and wonder out loud if I'd earn a spanking too. A couple of times when I was young he even wrestled me over his lap and put me into the spanking position, but then said that he'd let me off "this time".
In short, he was a petty tyrant who didn't want to babysit and worked out his frustrations on his sister's backside.
When was a kid I used to have nightmares about him. But as I grew older, some of those dreams stopped being nightmares, not that I understood why back then. Then, before Sally or I were teenagers, the family moved away to another state and we lost touch.
Well I spent a lot of my teen years dreaming about being over his lap and those dreams never really died, even though I never had the courage to tell any of my lovers about them. Then, recently, I connected with Sally on facebook and discovered that I'm now living in the same city as her brother! I've friended him as well, but he doesn't seem to remember me much.
I'm in my early 20s, he's in his later 20s, so the age difference isn't really much anymore.
Now for why I need advice:
Should I go after him? Should I try to date him and then maybe bring up all those times he spanked his sister and drop hints that I'm a naughty girl too? Should I try to make those dreams a reality?
Confused Former Friend of My Dream Spanker's Little Sister
There. That's a nice confusing situation doesn't have a single easy answer. Maybe the answer should be one word (Yes, No), maybe it should be something about communicating sexual desires to her lovers, maybe it should come out against her trying to start something there, maybe it should tell her to move on with life.
I'm inviting any and all to write answers. If you want to give more than one then that's great. And ignore (or don't ignore, your choice) any answers someone else gives. In a couple of days I'll put on the "Dear Anne" hat again and come up with an answer (I'm not sure what it will be, but other than it will lead to spanking), but until then let's see if this experiment works.