Roman Holiday

Take her on a tour of The Vatican.

haha

Sounds nice on the surface – but when one breaks it down – it may not be worth the overhead (not necessarily financial overhead).

It would come down to how much you enjoy each other’s company and how she treats you – take her out on a dinner date and see how the chemistry is.

She may also want additional payment if she is going to be banging you while in Rome.

“… Take her on a tour of The Vatican …”

Too risky – strippers are too unpredictable and she may try to grind on the pope (or even ask him if he does VIP)

Not worth the potential trouble.

Jack, this can go many ways, both positive or negative. I say, let's look at this vacation like a trip to the strip club. The Roman Vacation is the VIP. You don't go straight to VIP without some test drive LD's.

Now, you've been with her already and that's good. How about some smaller trips or extended dinner dates to explore her personality and how well that you two get along over time.

If everything works out good, I say to give it a shot. If you decide to make a trip north to Turin, I have an Uncle Angelo who owns an old ass candy shop. I'll link y'all up.

Key question: are you going to have the chance to go back to Rome again in the future? If yes, then sure take her. There's a good chance she'll ruin the trip, and/or keep you from seeing what interests you there. But what the hell, if you can go back again some other time.

Just make sure she's not stupid/crazy enough to get your ass on the no fly list.

If you are unsure perhaps you could do a dry run and take her to Breakfast at Tiffany's.

Sure. Why not? I don't see any harm in that.

Who the fuck goes to Rome by themselves?

Who leaves the US these days?

After Rome, let us know about your trip to Odessa.

What id she is on the rag that week?

Shadowcat, that would be my first concern. Is she looking for a shopping spree in Rome? High fashion Italian clothes, shoes, handbags and accessories? Can you handle a week of her conversation, moods, laziness, drinking? Is she going to run up an international cell phone bill bragging to her girlfriends and expect you to "help" her pay it? Does she have a passport or will you have to pay for that too? Are you a fan of Italian opera? Would she enjoy that? If you're on business, can she entertain herself until you finish?

As to the Vatican, I read that Pope Francis worked as a bouncer in Buenos Aries before he entered seminary and the priesthood.

Jack, I say - Go For It!

I have had four different vacations with my Toronto sweetie. All have been very pleasant experiences for me; also horrifically expensive. The vacations have been at isolated resorts or in rural or gently urban areas, not big cities.

There are some caveats to my advice, Jack. I get the sense that you don't know this girl very well yet. I had a pretty good read on my sweetie before I broached the idea of vacation together. My Toronto sweetie is in her early 40s and possesses unexpected maturity (for a stripper). Your new girl? Toronto sweetie is educated and multi-lingual. Your new girl? SuperDude, ever the practical cynic, raises specific objections that might concern you.

Sweetie and I hashed out all the logistical details of the vacations before we left Canada. There were no tantrums or bad behaviour on her part. Believe it or not, the only tension between us was over the amount of sex. A major part of these vacations for me was just pure relaxation from the pressures of work. Naps and leisurely hours spent reading were part of what I wanted to do. Sweetie wanted to be more active than that (both in the sack and out). Sweetie claims we are a good fit sexually (and I don't disagree) but the damn woman is rapaciously insatiable! One of the reasons I see her only 2-3 times a year.

If you get all the details figured out to your satisfaction - DO IT. I have the impression that all this is easily affordable for you.

SD asks, "If you're on business, can she entertain herself until you finish?"

Another side to this, could you trust her in your living quarters alone with your stuff, or would you lock her out till you return?

Jack my man, don't do it unless you get to know her really well. When in Rome you don't want her to hook up with members of the mafia's kidney harvesting division.

You'll come back from business to find her waiting with a chloroform-soaked rag. The you'll wake up the next day in a bathtub full of ice missing an organ!

If there is any likelihood of that discretion should be the better part of valor.

Given that she hinted that she wanted to go, she may already be planning the kidney extraction. Beware!

On a serious note, art's comments seem spot on. You don't want to go abroad with somebody that's going to create problems, even if they are less extreme than stealing your kidney.

Let us know how much money she made hooking in Rome and stealing from your wallet. I don't get the whole travelling with strippers idea. Within 4 seconds of blowing a load I am on the road. I wouldn't even take my wife on vacation if she didn't ski, golf, play poker and like to smoke weed.

I love travelling with women. But it has to be the right woman! Maybe you should do a long weekend at a B&B first and see how that goes. And be aware she will want to go shopping in Rome. A lot. And you will have to pay for what she buys...your expenses will be far more than airfare and food. And does she want to be paid as well? If she sees this like she's an escort, she'll want $$$$.

My situation would make it damn near impossible for a stripper to travel with me, but I fantasize about that experience EVERY time I travel. Some of that is tied to my RIL status with my favorite girls. The fantasy of that kind of extended fun away from the club is intoxicating to me, and if I ever found myself single I would definitely make it happen. Sure, there are potential pitfalls that others have mentioned, most prominent to me being that you don't know her very well yet, but you're a smart guy Jack, I say GO FOR IT, and let the rest of us live vicariously through your exploits!

Italy's criminal system is getting more and more bizarre every year. Keep that in mind.

Not no, but fuck no.

I say try her on something smaller, like a trip to niagara falls. If she performs well inside and outside the bedroom, then have at her Italian style!

That being said Italy may not let her in based on previous crim, she may also attempt to bring a "personal supply" with her, which could land both of you in a jail with great pasta.

Either way, I hope the trip goes well.

I suggest when in Rome you tangle with a native woman. When in Detroit, take you new fav to Friendly's!

My vote is to go for it...

My vote is to go for it...

did it one time with stripper that I knew very well. trip to Hawaii for a week. worked out details in advance about the $$, down time and the sex. I paid for everything that involved us as a couple and gave her a daily stipend to spend any way she wanted to. fucked her at least 3 times a day and still had plenty of time for other activities.

I wouldn't do it. Not worth it.

But if you do, discuss EVERYTHING in detail before you go... money, sex, expectations. Etc.

It will save you a lot of headache if you discuss exactly what you expect and expect her to act on the trip, BEFORE you get to the hotel room.

Good luck.