I'll be traveling a lot soon, (conventions and such), and both family, (brother, sister0, and some other business associates will be around and most certainly in the same hotel. But still would like to play. Any ideas on how to successfully do this without calling to much attention to myself??
but I've used "going for a run" as cover. Not long ago I arranged an early morning appointment near where we were vacationing, ran to it, had fun, and ran back. Had to cheat on the miles but I still got plenty of aerobic exercise. When using this method you'll want to make sure a shower is available! 
Contact a provider with an incall that is near where you are staying. Tell the family that you are going to take a walk to decompress and head her way. Remember to shower before you leave her place to get rid of any fragrance you may pick up. When I play on vacation its always when the wife goes shopping because its an all day thing for her and I never go with her.
Have fun and stay safe.
I haven't done this yet, but on recent business trips have thought a lot about it.
I think you would never have the provider come to you at your hotel, too risky. Uber might be your friend here if taking the rental car to an incall would be too conspicuous. In my experience, there's usually an hour just after dinner where we all retire to our hotel rooms. Since I'm never travelling with friends, only coworkers, we don't hang out like friends would til 2 am. So after that hour, I'm free to roam away if I want to.
Travelling with siblings could be tough though. Hard to break away. You could always throw in the excuse that you have an old high school friend in that town, and you're going to visit him/her. I did that in LA last year, but then I actually did have family that I visited in LA. But that got me away from my boss for the evening and excused form any corporate dinners or vendor parties that night.
Hope this helps.
-- Modified on 7/31/2015 11:13:15 AM
When in a strange city, I'd rather have the lady come to me then try to find my way around town. The convenience is so worth it, and when the meeting is over you can go right to sleep! A good provider will know how to blend in at the hotel and will look out for clear hallways upon entering and exiting your room.
What a nice thrill it would be to have them walk in in the middle of your session.
And even if they don't, women can sense when another woman has been in her lair
You've been around here plenty long enough to know that almost EVERYTHING here needs to be spelled out as if talking to a five year old.
Do you REALLY believe that there isn't some dumbfuck reading this that thinks it's perfectly fine to fuck a hooker in the same bed that he plans on sleeping in with his wife that same night? Don't you remember the thread just a few days ago about the pros and cons of having an outcall to your own house when married?
It would serve one of these dumbshits right to have a squirter over to their room and then have to explain to his wife later that same day why the bed is soaked with pussy juice. lmao
Or, if everyone is at the convention, fake an illness and retire to your bedroom at the appointed time. I hobby on during business travel and business associates are easy to avoid. I wouldn't do it with family around, though - they're more likely to drop in and "surprise" you.
When I travel in circustances you described, I do not play. Way too much of a risk to take for little pussy, not worth it for me. Your reputation is everything for a professional.
Once lost, you are pretty much fuckec.
my professional reputation would be enhanced....
consorting with prostitutes has always been part and parcel of being in mining...
that's why I have a hard time with people's negative connotation applies to whore, hooker, or prostitute; those are terms of endearment to the people I know.
not so much in my personal life though 
But I'm single so it's not unusual that I would bail on coworkers for an evening, and family members who might travel with me don't have a seriously vested interest in meeting my friends.
Hotels normally will separate coworkers by several rooms especially upon request at check-in, but what about a coworker from another part of the world? They might be from a different company name that's still under your umbrella company, and end up next door - do you want to explain that at breakfast?
Conferences are tough, but you could always play hooky one afternoon and claim you felt ill. Pick an arrival/departure time for an outcall where the conference has a session underway and it would limit the possibility of someone seeing who enters/leaves your room.
I am VERY happily divorced and I am not a bit ashamed about seeing hookers.
Of course I am in the oil business and people expect me to be a whoremongering pig, others I suppose have the "morality bar" set at different levels.
Me neither. If I were single I would still be discreet, but I certainly wouldn't be embarrassed. If it's something that you enjoy then fuck what others think.
Same thing I hear from guys being embarrassed about being seen entering a stripclub. Really? I don't get that at all. I proudly walk in with my head held high like I own the place. I guess a lifetime of "fuck you's" has given me a certain hardness and non-concern about societal expectations.
Of course I am in the oil business and people expect me to be a whoremongering pig, others I suppose have the "morality bar" set at different levels.
In the US there's a stigma that's just not worth the morality drama that will ensue - especially with MY family. And coworkers? The less they have to gossip about the better. I've hooked up with colleagues from other countries yet still hear snippets from people whose lives must be so boring they have to examine other people.
In the EU it's not something I worry about, and have had a driver drop me off for a date knowing it's an escort. Been to brothels, and have been asked to provide similar entertainment for others
And unless you're standing in the hall with your wallet out, handing bills to a disheveled lady in lingerie and clear heels, then what's unusual about a "friend" visiting your room?
and head to her incall.
That way as far as the family is concerned, you're slaving away listening to boring speakers while they are off spending your money.
I've done this several times.
Don't use your hotel room. I did that and my wife immediately sensed that another woman had been in the room. I told her the maid had come and did some straightening up, and was wearing some perfume, but I don't think she bought it
Never, ever give a business associate your room number. If they need to call you, they can call your cell or call the front desk and ask for you by name. Then, if a lady is knocking on a door, she's knocking on a door and not your door. It is difficult at times to break away, I know this very well what with meeting for cocktails and business dinners. And if you get stuck with clingy business associates as I have in the past, they think because you are traveling on business together that you should spend every waking moment together. That is an unfortunate and difficult situation to deal with, sometimes you need to feign a "oh I'm going to meet my Aunt and Uncle, that live in this city, for dinner since I'm here" so you can make hobby appointments ahead of time. Very few ladies are available last minute.
I don't have siblings but I've traveled with other family and same thing, there is no need for them to know my room number, none, period.
Just say: Oh, it's almost time for my spa treatment, got to run.
No one dare tries to hold on to you after that line
I make it quite clear that "What I am doing" and "What we are doing" are two VERY different things when traveling with friends and or business associates. Of course, since I have no reason to lie, no one is a bit surprised when I tell them that I will not be able to have dinner with them at 7 because I have a hooker coming over. They can either put dinner off until 8:30 or so, or they can eat without me. lol
Just one more reason to do this shit out in the open.
I honestly can't imagine having to make excuses to people for my desire to get my dick wet. It really must suck for most of you to have to lie all the time.
Unless you are alone, having her visit you will be risky...family and business associates will probably be aware of your presence at any hotel you stay at, so it's best to sneak away when they will not be bothering you, such as after you've retired for the night.
Arrive at the destination a day early. On my own then hang with my friends the rest of the trip. Or if friends are already there I'll tell them I'm going to meet a friend with their kids. My friends don't want to go so I'm able to sneak away.
When I am on the road with business associates, I ALWAYS ask the hotel to put me as far away from them on another floor as is possible. (I just tell them that I'm the boss and do not want knocks on my door at 8 am.) And then I don't tell my associates my room number... or even my floor if I can avoid it. (And I have been known to quietly change rooms the day after check-in after learning that an employee was directly across the hall.)
If you have a rental car and plan to drive it a ladies location, be sure to park some place not too memorable, and preferably a bit away from the door (to avoid door dings on the rental, after all)... just in case the same spot is not available when you return late at night..