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Posted

So I met this guy who in his dating profile said he liked to crossdress and be a sub. I just wanted to pick his brain and suddenly found myself loving doing and saying things he finds arousing. At first I was kinda faking it but I’m good at it! Problem is I know zero about this stuff. I want to do it right. I don’t even know the questions I have. I am open to advice anyone may have. Please don’t be mean. I really want to know more about this. I’ve never experienced it and didn’t think I’d like it but I do.

Posted
Based on the information you've given it's very difficult to comment - especially as it's not clear which half of the couple this is.
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Generically though you can only know by talking to this guy, finding out what he likes and what he expects. Spend some time thinking about your own likes and desires in this regard and seeing where you're aligned.
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Read as much as you can, forum posts, blogs etc and start to form your own ideas of what this may all mean to you and then figure out how to adapt that for him.
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Take things slowly and make sure you learn as much as you can about different aspects of what you are doing.
Posted
I would also add to the other comment ask questions that lead to what he ultimately is going for and if you find that something you enjoy as well. I usually ask what a recurring fantasy they have as a role play situation which then gives you an idea of what they think about or may already know they like and construct something from there.
Posted
That's really amazing!
What you want to do next is sit down and discuss with him on exactly what he wants. Mind you, every submissive crossdresser (or sissy) has a different taste and take on things. Ask him of his fantasies and desires and see if you can match up with them. Even if you are not experienced but want to have a go, read online on his fantasies, watch videos and most importantly research on the fantasy... It will give you a greater insight... Sooner than you know you shall discover much more to his fantasies than originally discovered...
Hope this helps!
Posted

I think the common advice as often is...

talk to him.  what is he liking what isn't he - what are you liking, what aren't you : if you get an idea what makes each of you tick that's a basis to build on 

Posted

What *they* said - discussion's the way forward.

One thing that might help is the BDSM checklist (if it's still floating around somewhere on the masturbation superhighway) Basically, it's an exhaustive list of kinks, which is a great conversation starter.

IndigoSigmaSwitch
Posted
Hmm I see a problem here. And that problem is...that guy should have been me. I think you were just really vibing and interpreting his responses which made you push it a little further. Come on girl.....admit it, it turned you on., coz, you are a natural domme. Maybe next time, just crank it up a little, let yourself get stern faced and in a more condescending tone humiliate him a little. Voila! If he starts to shiver and cower then he be liking it. And if that gives you an unfamiliar, but, pleasant tingle, then stand up and boss that little bitch around. Make him crawl to your feet, maybe lick your boots or something weird like that. And then look right at his crotch and say these words "Let me see that little cock of yours, is it gettin hard when I boss my little bitchboi around" "Take it out and show me" If he does....then I think you could do whatever you wanted to him.
  • 2 months later...
jessgirlyguy
Posted

it's nice that you've enjoyed it, talk to each other, work out what works for you both

Cristielynn
Posted
On 3/10/2022 at 4:45 PM, Shayaishere said:

That's really amazing!
What you want to do next is sit down and discuss with him on exactly what he wants. Mind you, every submissive crossdresser (or sissy) has a different taste and take on things. Ask him of his fantasies and desires and see if you can match up with them. Even if you are not experienced but want to have a go, read online on his fantasies, watch videos and most importantly research on the fantasy... It will give you a greater insight... Sooner than you know you shall discover much more to his fantasies than originally discovered...
Hope this helps!

You know what helps is to roleplay into the conversation that is how I got into my future wife's head and unlocked her kinky side and I discovered that she loves being in control and love to roleplay..like I get into bieng her slutty girlfriend..

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