Im having my lucky day this Saturday with a civi girl I used to see for awhile.

Anyways, we will be inside a hotel room for almost 24 hours, being an "indoor" date. She is rather shy and inexperienced, but you know I like to try new things, especially VERY kinky ones.

Just spent an hour looking online about ice cube, typical back door, etc, but nothing really stands out from the crowd.

I guess Im asking about it based on any experience you might have had. Any recommendation for what I can do to open up rather a shy girl? Let's see what you got!

..to a shy person might just send them running in the opposite direction. How about starting with the more obvious stuff and see how she responds to that?

How did you get a civvie girl to join you for a 24 hour in-room hotel date? I would never commit to that in my real life lol.

Being rather shy and inexperienced I'd suggest not freaking her out with your kink right off the bat, she may not want to come back! Try suggesting a blind fold... light spanking/hair pulling... tickle her with feathers.... but don't expect her to be all in when you introduce a butt plug or bondage equipment! Also I wouldn't jump straight into the name-calling, some ladies don't enjoy being degraded. If you're REALLY into it, get a golden shower from her while wearing her panties!




Good luck...

Sex is no problem of course. It's just the wall that I need to go over when I want to make transition from a typical sex to more exploring and playing around. In a sense, being more comfortable. I figured if I knew what to do specifically, kinky idea, I would know how to make this transition.

But the problem is I fall asleep REALLY easily when I'm drunk.

I will NOT be happy if I fall asleep at like 8pm and wake up at 11am the next day. LOL

a two way street. If she is not receptive, all your transition work is for nothing. You can suggest something and see by her reaction if she is even the least bit receptive to your ideas. And please for Gods sake, don't get her drunk or drugged...that is so low and could cause you some serious issues. If she is not willing sober, then just be a gentleman and leave it at that.

Is it true that based on personal preference some people will never be into kinky stuff?

And no i wont get her drunk, mainly because also I am really not good with alcohol myself. LOL

Have fun though young man!!

Wonder if his shy girl would go for that?   That would liven things up!   LMAO

Is that prepkid?
Looks like that kid needs a bump!
Hey Saturn! I'm just kidding!
I would never drug my girlfriend, or any girl for that matter.

I dare ya!

Rehearsals are dreadfully boring .

Bring vibrator with  fresh batteries   , preferably a rabbit .


Once her motors are revving , go with your imagination , or follow her lead .  
 

If she is shy, the last thing you want to go is slam her in the face with your kink.  And I agree with the light stuff....blindfold and teasing.  Maybe blindfold and a little food....maybe some chocolate sauce on your unit or strawberry covered with her juices.  Feathers are a great idea.  Seriously, anything to get her to kind of expand her mind as to what makes her feel good.  If you get comfortable, maybe she would let you tie her up (maybe at least her hands).  Maybe you ask her to tie you up so she can explore what she likes to do to someone else.  

But if you try to "transition" a shy girl into full scale kink in 24 hours, you will be very disappointed if you ask me.  If you hit her over the head with it, it's just going to reinforce her feelings of apprehension.

you could tie her up loosely, blindfold her, and tease the living hell out of her. Tease and Denial is oh so hot!

What the heck did I do now to warrant that?

and find some porn that pretty much describes what you want to propose, then make some comment to her about it and see if she smiles or scrunches up her nose at it.

She'll figure you out, but at least you're being as discreet as possible.

But he ain't no kid.... Is kid rock a kid? LOL..

He could be 80 for all I know. I was just playing off his board name...no harm, no foul...

I second London's suggestion. This can be very hot and sexy and if she trusts you it's a good start for someone like ur girl who is a bit inexperienced. Who knows, maybe she will get inspired to tie YOU up and get crazy

... that guys should take up whether it be a civilian or provider situation.

Serpius

Offer your prude date the Dirty Sanchez!

That's the one!  You are truly a fucking pig! LMAO!

Your post is beyond unclear.

Just kinky. It's hard to spent hours on cow girl position, etc.

Trying to find out what would make it really fun.

If you are looking for different positions, then pick up a copy of the Kama Sutra, and you have a lot to work with there.

Beyond that, you can blindfold her, tie her up, get tied up yourself, introduce handcuffs, hot wax and candles, etc.

Everyone defines kinky differently, and the sky's the limit as to how weird you wanna get.  If you want to see how disgustingly kinky you can get in session (well beyond the point of what I would consider anything even remotely a turn-on), then read the reviews of Gina Rollins.  Of course, she's got some really disgusting, nasty-ass clients, as some of her sessions involve eating shit.

So...you might wanna narrow down what it is that you're looking for.  "Kinky" doesn't mean anything specific.  You just might be thinking different positions.  But someone else might be thinking this involves bodily fluids.

http://www.urbandictionary.com

Blumpkin for example!