An Upcoming Weekend

[Reluctant Daddy]

I had originally intended to step back for a while and refrain from hiring, but the recently discovered "BFE" put the brakes on that sabbatical. I'm afraid it could easily become addictive.

 

I'm in the process of setting up a weekend with an escort and the nerves I've experienced before are nothing compared to this. I've spent some time with this guy and have really enjoyed being with him, and I've enjoyed the attention and affection he's given me.

 

I want to make certain that this weekend is as perfect as I can make it, for both of us. First fumble was that the hotel he suggested wasn't available for the dates. I'm trying to find equivalent accommodations - should I make sure he's fine with them as well? I'm easy going as far as activities and food, and he's mentioned that he is as well. Should we play it by ear once there, or should I try to plan out things to do? This will be my first time visiting this city, so I'm pretty much unfamiliar with everything and don't want to fumble on this.

 

Any thoughts, suggestions, recommendations, warnings, etc. are welcome and appreciated.

[liubit]

Oh well, dear [uSER=12070]@NYClocker[/uSER], you certainly are the most gracious host, and I am positive that your date appreciates your preparations. I have one piece of advice, if I may: don't overthink things. This is primarily supposed to be fun, fun, fun, and not D-Day planning

 

I have spent many a weekend with different escorts. Some spontaneity is always liked, particularly if, as is often the case, your boy is younger than you are. Perhaps most importantly, some alone-time is absolutely required. Do not expect to spend every second of every minute of every hour of every day together: you will drive the escort and yourself absolutely crazy.

 

Lie down, relax, and enjoy your weekend!

[jjkrkwood]

The MOST important thing to remember is that this is a BFE, NOT a boyfriend. Keep your emotions in check and just enjoy your time, however you both agree to spend it.

[Reluctant Daddy]

I have one piece of advice, if I may: don't overthink things.

 

I'm really overthinking this, pepper with a lot of "what if's." He is younger, and some of the fear is what if he's bored to death with the activities?

 

The MOST important thing to remember is that this is a BFE, NOT a boyfriend.

 

I'm realistic enough to know that there's nothing more there than the illusion. That said, I'm very fond of this guy and would like to make this enjoyable enough for him so that he'd look forward to doing it again.

[jjkrkwood]

I'm really overthinking this, pepper with a lot of "what if's." He is younger, and some of the fear is what if he's bored to death with the activities?

 

 

 

I'm realistic enough to know that there's nothing more there than the illusion. That said, I'm very fond of this guy and would like to make this enjoyable enough for him so that he'd look forward to doing it again.

 

 

Well you sound like a guy that is smitten... I hope your sojourn meets all your expectations.... Cheers.

[Reluctant Daddy]

Well you sound like a guy that is smitten

 

Not smitten, but I feel comfortable with this guy. For me, it's easier and less stressful.

[MiamiLooker]

I had originally intended to step back for a while and refrain from hiring, but the recently discovered "BFE" put the brakes on that sabbatical. I'm afraid it could easily become addictive.

 

I'm in the process of setting up a weekend with an escort and the nerves I've experienced before are nothing compared to this. I've spent some time with this guy and have really enjoyed being with him, and I've enjoyed the attention and affection he's given me.

 

I want to make certain that this weekend is as perfect as I can make it, for both of us. First fumble was that the hotel he suggested wasn't available for the dates. I'm trying to find equivalent accommodations - should I make sure he's fine with them as well? I'm easy going as far as activities and food, and he's mentioned that he is as well. Should we play it by ear once there, or should I try to plan out things to do? This will be my first time visiting this city, so I'm pretty much unfamiliar with everything and don't want to fumble on this.

 

Any thoughts, suggestions, recommendations, warnings, etc. are welcome and appreciated.

Shouldn't you be discussing your concerns and expectations with the escort? He's the only one that can answer your questions.

[MikeBiDude]

I'm really overthinking this, pepper with a lot of "what if's." He is younger, and some of the fear is what if he's bored to death with the activities?

 

I used to worry about that a lot, especially whereas I like to go to sleep earlier than most younger guys do. First thing I found is often they prefer the early rest too!! Second thing I've found is the BFE overnight guys are amazingly adaptable.

 

Don't worry about it too much, relax. Be sure and offer him some alone time a couple/few times a day for himself. Ask what activities he might want. Movie? Meal at home?

 

Have fun...

[Reluctant Daddy]

Shouldn't you be discussing your concerns and expectations with the escort?

 

We've discussed the basics, but I'm not sure how much actually needs to be discussed since this is my first weekend appointment. I don't want to be that 500 emails guy.

 

Be sure and offer him some alone time a couple/few times a day for himself. Ask what activities he might want. Movie? Meal at home?

 

We've discussed alone time, workout time, etc. We'll most likely dine out or room service. Movies would work for me. Some sightseeing (although he's most likely done that).

[happyguy2]

We've discussed the basics, but I'm not sure how much actually needs to be discussed since this is my first weekend appointment. I don't want to be that 500 emails guy.

 

 

 

We've discussed alone time, workout time, etc. We'll most likely dine out or room service. Movies would work for me. Some sightseeing (although he's most likely done that).

More than once, when the escort has seen all the sights, he was very eager to show me around, telling me what he knew, having lots of discussions about things, finding new things etc. I have, in each of these cases, really enjoyed it, and it gave us all sorts of new insights into each other . Now I know, what works for one, doesn't always work for another, so .... just sayin.....

[jimboivyo]

Shouldn't you be discussing your concerns and expectations with the escort? He's the only one that can answer your questions.

 

this. it sounds as if you're not communicating near enough. ask this guy his opinion on things BEFORE you get into the deep end of the pool

[liubit]

Excellent advice from everyone, I think. One further little question, [uSER=12070]@NYClocker[/uSER]. You mention that it will be your "first time visiting this city". Is it the escort's place of residence, or is it going to be new for him too?

 

If it is the former, let him suggest activities. If it is the latter, well, it is a different story: enjoy discovering the place together. It can be lots of fun! Enjoy, enjoy, enjoy!

[nebula]

you are hiring him to show you a good time. he should be the one worry about all this not you. all you need to do is show up, enjoy yourself, and pay the amount you guys agreed on. leave the rest to him. if you are not having a good time and bored to death, time to find another escort.

[bigvalboy]

I had originally intended to step back for a while and refrain from hiring, but the recently discovered "BFE" put the brakes on that sabbatical. I'm afraid it could easily become addictive.

 

I'm in the process of setting up a weekend with an escort and the nerves I've experienced before are nothing compared to this. I've spent some time with this guy and have really enjoyed being with him, and I've enjoyed the attention and affection he's given me.

 

I want to make certain that this weekend is as perfect as I can make it, for both of us. First fumble was that the hotel he suggested wasn't available for the dates. I'm trying to find equivalent accommodations - should I make sure he's fine with them as well? I'm easy going as far as activities and food, and he's mentioned that he is as well. Should we play it by ear once there, or should I try to plan out things to do? This will be my first time visiting this city, so I'm pretty much unfamiliar with everything and don't want to fumble on this.

 

Any thoughts, suggestions, recommendations, warnings, etc. are welcome and appreciated.

 

Shouldn't you be discussing your concerns and expectations with the escort? He's the only one that can answer your questions.

 

Miami is correct. Communication is key to any successful hire, regardless how comfortable you are with him. Going to a new city, take sometime to do your homework and make yourself familiar with the city, and run some ideas by him. Lastly without getting preachy, give him some free time over the weekend for him to answer text messages, emails etc. and to take care of any personal business he might have. We all need a little alone time. Good luck...

[Reluctant Daddy]

Is it the escort's place of residence, or is it going to be new for him too?

 

I think he may have lived there at one point, but he'll be traveling to meet me.

 

you are hiring him to show you a good time. he should be the one worry about all this not you.

 

Am I wrong in wanting to make sure he has a good time as well? I'd like for him to be a regular hire so I'd like to think he would return if he had a good time too.

[slightly]

Am I wrong in wanting to make sure he has a good time as well? I'd like for him to be a regular hire so I'd like to think he would return if he had a good time too.

 

Not at all, you're both human beings, consideration for each other is the best way to improve a "business" relationship that you are fostering in the long term. All relationships are two way streets. As said before, communication is key.

[+ azdr0710]

yes, communication is the key......so we'll be expecting hourly updates at the board on how the weekend is going

 

you say you've hung out with him before, so that should certainly make it all - at least somewhat - more comfortable....do not overplan this thing!.....hang out somewhere for coffee or a beer, walk thru some farmers' market or similar, see a movie or play or comedy club, take a nap together, talk slowly, sit at the pool.......

 

hang out with him like he's a good buddy, not some escort hire

[+ Gar1eth]

I always wanted the escort I was with to have a good time too. But as these trips were the only time I would be able to act like a normal adult who was away for a weekend with a special someone, I wanted to be sure I had a good time too. That's why, and most of this occurred before texting became so popular, I wanted to actually TALK to a guy I was considering a weekend alone with to make sure our interests matched. Occasionally even with talking beforehand, it turned the weekend was a bust. But that usually occurred when the escort wasn't honest about what he liked.

 

I once set up a weekend with a younger escort who is still advertising. I told him I like plays, musicals, doing touristy things. He said yes that was all time. But once he arrived, he wasn't that interested. I actually had found a tourist-excursion steam railroad trip that included a wine tasting. Well he enjoyed the wine tasting but that was about it. The following day as we were about to take a tour of the city, he indicated he wasn't interested in going. I'm glad as it saved me money. But when we discussed things he 'accused' me of arranging events that only people of my age would enjoy and not a 24 year old like him. Well I disagreed as I would have enjoyed the things we did when I was 24. But the main reason we didn't 'click' was the escort lied to me beforehand on things that he would find interesting to do.

 

So my advice is if you think the two of you are compatible interest-wise, ask him in generalities what kinds of things he enjoys. Then if you enjoy the same type of activities, schedule a few of them. Don't over schedule (which was sometimes my problem) as you'll want some alone time with him.

 

But if it turns out that his interests and your interests don't intersect very well, then maybe this isn't the guy to take for a longer trip. Maybe he's more of a few hours to an overnight guy.

 

If you were to be scheduling things mainly for him though with not much thought for yourself , it seems to me that you have started on that slippery slope of thinking of the escort as a boyfriend instead of a boyfriend experience.

 

Gman

[dlee02]

Many excellent advice already posted. I would emphasize clear communication before hand, and as I said recently in another thread, during the actual weekend, just relax and enjoy your time together.

 

Do your homework and have a few plans on hand, but hold on to them loosely during your time together as things change or rarely work out perfectly.

 

Enjoy!

[Reluctant Daddy]

The upcoming weekend has passed and it was fantastic! We did some of the planned activities, a lot of unplanned activities, and spent a lot of time just walking, talking, relaxing and connecting over meals and coffees. It was fun, relaxing, invigorating, and it made me feel a little less old. I definitely would do this again!

[+ glennnn]

I don't know what your entertainment budget is, but arranging for massages would be an activity that a man of most any age would enjoy and could lead to a nice, cozy evening together after the masseurs leave. It would be a special, intimate treat for both of you.

 

Remember that you are the client, and be yourself. As much as you want to please him, you can't force guy to guy chemistry; it either happens or it doesn't. If you don't click for real, don't fake it or then future weekends will continue to be a strain.

 

You sound like a wonderful man; if he is also wonderful, he will recognize his good fortune and respond. Try to relax.

[madjim]

Currently in same boat of doing a weekend. I am in a different situation then you but overall did as most said on here. Had clear communications with him about where, when and activities to do. On one date we sat and check out the location and review what I got for us for the weekend. I told him to think of activities available he like to do and we just take it easy and have fun. It should be enjoyable for both of you and doesn't need to stress you out.

[+ friendofsheila]

Given that YoungMan is acting in a professional capacity during this whole trip, might it be good to leave a portion of the planning to him, perhaps when he arrives and he has "clocked in"?

[nate_sf]

The upcoming weekend has passed and it was fantastic! We did some of the planned activities, a lot of unplanned activities, and spent a lot of time just walking, talking, relaxing and connecting over meals and coffees. It was fun, relaxing, invigorating, and it made me feel a little less old. I definitely would do this again!

 

Really glad to hear it went well. As [uSER=12155]@Dominiking[/uSER] mentioned, you sound like the dream client in that you put thought and consideration into the planning but was not obsessive. A combination of planned activities and unplanned go-with-the-flow works best for these kinds of weekends I think. Chemistry is important of course, but so is compatibility and thoughtfulness. Well done!