Hello all.  I am about to move to Chicago due to a recent promotion and I am looking to celebrate.  I want one insanely crazy night that I will never forget.  I would love some suggestions.  A threesome will not cut it.

-Guys, if you could create one unforgettable evening, what would it be?

-Ladies, it is important to me that you truly enjoy yourself as well.  If you could create one amazing date, what would it be?

So you're looking for one hell of an experience hmm?
I am a veteran of the companion-orgy (4+ people) I have been so lucky to have been part of several!
My current fantasy is a moresome with all these luscious ladies:

Myself (Chicago)
Marla Lyons (Boston)
Adahlia (San Fran)
Nathalie Rose (Toronto)
Anzah Rose (San Fran)
Natasha Lee (Tuscon

would be pretty awesome as well as something I can offer!  Too bad our Orgy party is over or that might have provided you what you might have been looking for, though we are all willing to come out and play with you!

Wow..sounds like fun, but I think three ladies would probably be my limit.  Looking for something a little more passionate and intimate.  Maybe some elaborate role play, quick road trip or flight,...I have a few ideas, but will wait to see if others have any suggestions.

Thanks

Thanks,  the thought of seeing, hearing, and smelling a bunch of old, hairy guys screwing is not very appealing to me.  Wine and a nice night in sound good, but looking for a little more.

Okay keep in mind that I'm an ambitious motherfucker so my ideas are probably bigger than what's realistic for a single evening. That said...

1. Camping. My favorite. And none of that pussy campground RV shit. I'm talking deep in the middle of nowhere. Think Deliverance minus the anal rape. Bonus points if I can bring my guitars so we can jam out with Dueling Banjos. Obviously this would include a romantic under-the-stars setting with lots of woodland boning.  

2. Some sort of cheesy daytime date like pottery class, cake decorating or tango lessons. Then back to the hotel for some afternoon delight before getting ready for an evening at multiple strip clubs, live music venues, karaoke joints and gay bars. I'd try to keep my glitterbombing to a minimum, but I make no promises. Late night drunk banging is highly likely.  

3. Tandem spa day with massages (no not that kind, you dirty devils), facials (also not that kind), and seaweed wraps. Return to the hotel for some tantric sex, followed by a romantic candlelit dinner at a quiet rooftop restaurant. After dinner, maybe go for a walk through a park or perhaps see a play or something. We'd both be looking fresh to death in our fancy garb, so all of it would end up on the floor the second we end up back at the hotel. Maybe top it all off with some champagne while we're naked in front of the fireplace?

I know, I know. I have sweet ideas.  

If you're looking for a night of absolute debauchery then it has to involve Bebedoll. Just send her a quick note stating what you have in mind and then let her go wild in setting something up.  

You will definitely remember it. I've had the pleasure of Bebe's company many times over the years and can just about remember each encounter in vivid detail

I like two and three.  You know me though and could have probably guessed that.  I mean, who doesn't love gay bar music and glitter.

At least 5 girls laid out next to each other, legs overlapping, furiously pleasuring each other while they wait their turns.  I'm reasonably sure I wouldn't forget that...in fact I'm skeptical that Alzheimer's could even screw with that memory!

What's the donation for a summer long excursion on the Appalachian Trail?  Ideal date!

I am not sure what constitutes crazy either, just looking for something I may not normally do.   I know that is not very helpful insight.  To answer your other questions:

I enjoy working out, mud runs, art, tattoos, movies, golf, women
I would prefer a partial night out rather than staying in the entire time
I would not say I am kinky.  I can be more dominant, but would probably be described as laid back, sensual, and passionate.  If Tobi reads this she may be able to add to that.
Love trying all new foods

-- Modified on 12/19/2013 5:34:27 PM

It's a trip to NYC or New Orleans, hands down. NYC includes wonderful weirdness such as Sleep No More, with the troupe's unusual immersive approach to theater creating such an epic experience that they've extended their production run multiple times, and I think are now running a couple of years past their original anticipated end. NYC is a bit of hedonism refined. It's most fun if you have a bit of an idea on where you want to go, or what you want to do, with enough wiggle room to slide into something new if tempted in the right way. Fortunately, the sheer size of the city means just about any desire can be supported and sustained by enough people, leading to food, drink, and entertainment of everything you can imagine running all hours, so it takes very little of that of advance planning to have a truly wild or amazing experience.

New Orleans almost defies explanation. Still dark, still very corrupt, still edgy and a bit dangerous at times, and yet I've never met a people who drink down life as enthusiastically as these people do (with proper manners and napkin use, of course-they're still Southern! ). The city is like a deep stage with layers upon layers of curtains, and every trip another rope is dropped, and a velveteen curtain pulled aside. Moonshine tastings, carriage rides, the most amazing boozy frozen coffee in existence, card readings, brunch Bloody Marys and drinking in the streets (I swear the body processes booze differently in New Orleans), coffee in open air alleys with cobbled stones and flora so overgrown that you near expect the wild to close in any minute, my favorite strip club in the States, days upon days of music, happening upon the Night Market on Frenchman's street, chance meetings over and over again with a certain phenomenal storyteller and local artist, a Mardi Gras invite into closed restaurant followed by hours of wine and conversation by a happy chef who gave himself to the city years ago, and heeds her call of Serendipity... Sin, sustenance, drink, and joy are offered on every corner, and when you drop the planning and give yourself over to the city she'll take care of you. And, if she really likes you, then every so often she might show sign that she's followed you home.

Of course, if you prefer to stay local, then Chicago does have its fair share of wonderful times. Plays, burlesque shows, some of the most amazing artisan cocktail bars anywhere, architecture tours, museums upon museums, a veritable food Mecca with some of the best offerings in the country, kayaking and boat trips on the river and lake (though not this time of year!), some of the best blues and jazz outside of NOLA, festivals ranging from neighborhood summer events to the Chinese New Year celebrations in China Town...and the list goes on.

I wish you a lot of luck and happiness with your new move. I moved here several years ago, and the city holds sway over my heart like nothing else, even despite the cold snowy winters! There's a lot to do and see; have fun knocking everything off your list!

and possibly some of the great vices.

Thanks for the thoughtful response!

Rent a theater for one movie and pick one of your favorite movie to show, something that would have some eye candy for both sexes, private showing were you must attend in cosplay. You go to dinner after and all participants have to talk and act to each other in character. Then the most daring go back to a private place where you have to portray your character in sexual acts on each other. Bonus points for the person that brings multiple outfits and correctly changes personality to match the believed sexual nature of the character they are dressed to be.  

Setup a gaming system with fun party game like Wii bowling and have challenges were low scorer has to perform a (non standard) sexual position on another participant from a pre-approved list of positions.

Through out the night each attendee awards points/tokens to each other for staying in character or most creative, etc and after a certain amount of points you "level up". First person to a certain score becomes King or Queen and can dictate his or her subjects to perform acts on each other or on himself or herself for the rest of the time together.

That's if he can handle it ..... hehehehehe

wayyyy up skyscraper high and lowered lowered lowered to cock sucking position wayyyyy down below.  

It is true when a guy writes me and says " lets do something you have always wanted to do and never have".. my response is.. do you have access to a crane?  

BRING IT!

END OF MESSAGE

You continue to amuse and amaze!
Hope to see you during my Chicago trip in January.
xoClair