There’s No Gentlemanly Way To Ask…

Asking for something I’m curious about is pretty much impossible for me. Asking for something I already enjoy is equally difficult.

It comes down to a few things.

-It’s hard to not sound like a do-me sub if I were to ask for something.   

-If a guy asks a woman then it’s creepy. If a woman asks a guy, then it’s hot.

-I genuinely don’t want a woman to do something just for my benefit, I’d much rather she do it because it’s what she wants.

-There’s no gentlemanly way to ask someone to fist you.

I’m using fisting as an example just because I recorded a podcast with someone who talked about it and then had another conversation with a friend yesterday and wondering how I’d experience that popped in my brain.

You can use any number of other things to replace fisting. CBT, sounds, mummification, strap-on play, teasing, or just a good old fashioned beating.

How do you ask someone to do something dirty to you like a gentleman? How do you do it without sounding like you’re just being greedy and not interested in only getting your desires met?

I mentioned this on Twitter and had a few interesting replies. I’ll take their names out since I didn’t get their permission to repost. (yeah..I’m a badass mofo)

“Terribly sorry, old bean, but could you be a chum and just give my prostate a little squeeze? There’s a love.”

“Pardon me, don’t mean to be a bother, but could I perhaps have a hand? In my ass, that is.”

“Do be a dear and shove your fist up my ass. It would be greatly appreciated if you could at your earliest convenience.”

“My darling, what lovely fingers you have there. If it pleases you, feel free to massage my prostate with them”

But it’s not just kinky sex. I remember having a conversation years ago with a vanilla woman I was sleeping with. She asked why I never asked her to go down on me.

Her: “Why don’t you ever ask me to suck your cock?”

Me: “Well, I figure you’d do it if you wanted to.”

Her:”But I think it’s hot to hear a guy ask me to suck his cock”

Me: “Will you please suck my cock?”

Her:”No, not now.”

There’s another side having desires.

While playing, I really don’t think about anything other than what’s happening. I get lost in the moment and forget what it was I wanted in the first place. Or maybe I get into some submissive headspace where what she desires becomes what I desire and what I was curious about doesn’t matter anymore. It’s like my sexual desires become whatever is happening, whatever she’s doing to me or having me do to her in the moment is exactly what I crave.

True, if I”m being teased or something, then I’ll really want to fuck or to go down on her, but I don’t crave any other kind of play.

Maybe that’s a good thing. I’m lucky that I’m never wishing for something else while someone is playing with me.

So is there a way to ask someone to play with you without sounding creepy? Or to ask for something specific without sounding like you’re a do-me sub?

Reader Email: Advice Not Needed

Another email from a reader. I gave her advice that wasn’t necessary after all:

“I came across your blog while reading about BDSM and thought you might be a good person to talk to. I am a dominant woman that seems to be making a lot of mistakes in seduction of submissive men. Well, that is, I’m having trouble identifying them. The other day I kind of ruined a friendship by taking a compliment as permission to, well, do things that he didn’t appreciate as much as I thought he would. I have trouble controlling my dominant feelings, I suppose.

I don’t really know what I want you to say or how I was expecting you to respond, but I feel very alone about this much of the time. My (more than) best friend is a submissive man and we relate to each other very well, but he’s not the extreme kind of submissive that I think about in the early hours of the morning. Don’t get me wrong, I do have my fun with him and I care about him very much, but I want to try something more and I don’t even know how to tell him. I guess, even being as dominant as I am (and I find myself getting more dominant everyday), I’m embarrassed by how dominant I long to become.

Thank you for writing a blog about your experiences and lifestyle. It’s incredibly validating to see men like you around, even if you’re 3,000 miles away in New York. I should really move to New York. Maybe for Law School…. Okay, so I’m flirting with you a little bit. That wasn’t my original intention. Promise. =)

Thanks for listening”

I gave her what I thought was some sound advice. I suggested that she make her desires known, that she may want to start off slow and slowly introduce him to the more extreme things she wanted from him. I went on and on and moments later she replied.

“Ironically, the evening I sent this message, he and I had a long talk about all that I told you about. It turns out, he was afraid of scaring me off with how much he wants to submit to me. He sent me a link to a chastity belt (okay, so I was too chicken to have the conversation in person and made him get on AIM) and I almost bursted with relief, satisfaction, and about a million other feelings. I’ve been wanting to lock him up for months.

To put it simply, I want complete control over his body. I want to instruct him on how to please me and beat the hell out of him when he makes mistakes. He once told me that he wasn’t into pain. At the time, I didn’t think I was into inflicting pain. He proved me wrong. I do want to inflict pain. I want him to take the pain for me… He told me that he’s been dying to get a whip in my hand for ages. That I’m the only one he ever wants to physically harm him (which is, of course, very flattering and sexy). We’ve also talked about pegging and are going to go shopping for a strap-on very soon. I want to try everything with him: spanking, torture, mummification… I even told him about “service-oriented submission” which I read about from you and he’s all for it.

The sexiest part of the conversation from my perspective: He said: “I don’t want you to want to do things to me anymore. I want you to do what you want to do to me. You know me very well and we’re best friends. I’d submit to you. If you ever went to put a chastity belt on me, and didnt talk to me about it first, id let you put it on and lock it because you wanted it there… if you slapped me i’d be on my knees.”

Mmm, very sexy. I would probably have denied myself and him if I hadn’t started reading blogs like yours. So thank you!”


After reading this I did my happy dance and felt that all was right in the world. I can certainly understand where her sub is coming from. It’s a scary thing to want to give yourself to someone, even if it’s for only a short time. It’s even scarier if you care about that person and are afraid of them rejecting you.

I wonder how many seemingly vanilla relationships are out there that are comprised of one person who wants to be owned and another who wants to control, yet neither of them talk about it?
I’m betting it’s quite a few.

What The Hell Is Slave Training

I’ve had the imagine of being trained by someone stuck in my head for a while now. As someone who wouldn’t mind (understatement) being owned by a woman someday, you’d think I’d know what that means, but I don’t.

Oh I’ve been asked how I’ve been trained. My only answer is that I haven’t.

I’d imagine it depends on the goals right? The goal would be…….too…serve..the dominant…better?

Obviously it has something do to with something. I know it’s not nothing.

There are websites that deal with slave training, most talk about getting deeper submission out of the submissive and reaching a point of “total slavery”.

Total slavery? I have no idea what that means. Sign me up though!

A simple google search brought up Best Slave Training. I just breezed through it. Part of me didn’t want to read any of it since it might spoil it for a future woman that want’s to train me. It would be like learning how a movie ends before you go and see it.

In my mind’s eye I imagine it’s about just learning all of the small things that make her happy.

I’ll occasionally daydream about it both sexually and non-sexually. Since I can’t focus on one specific person that means that random women on the street will be the subject of my slave training daydreams.

I’ll see a woman on the subway and think:

-How does she like her breakfast?
-What body part turns her on the most when she’s kissed?
-How does she like her coffee?
-Maybe she’d like it if I met her at the door every day to take her coat.
-Does she prefer her clit sucked gently or hard?
-Holy shit what if she’s submissive??? I’m daydreaming for no reason! Oh who am I kidding she probably has a boyfriend. Crap she’s getting off on the next stop!

Ok maybe everything I think of as training, others think of as just learning to be a good boyfriend. Hey, I’m working on a blank slate here.

By the way, I think I may have hit a new low when my service/sexual fantasies revolve around women I have little chance of speaking to much less seeing again. I’ll admit I sometimes hope I’ll see their profiles later on one of the many BDSM dating sites I’m on.