I'd be interested in your experience. Do you offer more allowance, or does she ask for more, for overnight vs. just an evening together?

 
I hadn't really thought about it until today. Usually I suggest overnight and, with regulars, they stay or have a convincing reason why it's not convenient. I'd say my regulars stay overnight 2/3 of the time and the rest are just under 50/50. (Midday meetups excepted, of course.)

 
The pros of overnight usually outweigh the cons. Mainly, overnight means I get both evening pussy and morning pussy. Often middle-of-the-night pussy, too. The main con is feeling like ... "well, you do realize it's time for you to leave, right?" sometime in the morning.  I don't mind (and I rather enjoy) taking a girl out to breakfast, but often I have a call, a meeting, or a plane to catch. My day starts early. Nearly 100 percent of my meetups are at hotels. (And no, I'm not leaving her in my room after I leave.)

 
Today a chick asked for $100 more for overnight this Monday. I readily agreed since she proved herself awesome on our first date. I thought she was a little underpriced anyway. But ... this was the first time any chick has come right out and asked for more for overnight vs. an evening date. And I just can't remember any sugar baby ever asking for anything extra to spend the night. Either they can, or they can't.  

What's your experience?

 
Rockford

I live an hour drive away from the University town where my SBs live.  So either I'm driving to see them or vice versa, and one or both of us has to get home before dark for various other obligations.   I have had few overnights.  In most cases there was no mention of more $.  But in another she clearly wanted more, expected more, asked for more.  If you have established a routine date lasting a few hours, then she might well expect more for an overnight. Currently, just one of my SBs has the freedom to theoretically spend the night with me.  But although she's hot AF and loves sex, she's not much of a conversationalist.  I don't think I'd know what to do with her all evening, let alone all night.

I'd be okay with more $ for longer times.  But it really depends on what you are paying initially.  
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Also I routinely let the SB stay in the hotel room after I leave.   Haven't had an issue yet.  

Interesting. I've assumed leaving a girl in control of the room would open the door to all sorts of trouble. She could likely figure out my legal name, run up a big tab, invite friends to party, trash the place, etc. But now that I think about it, the girls I invite to spend the night seem unlikely to do such things. Perhaps I'm acting paranoid.  

 
And good for you! I know your girls appreciate being able to laze away in the room while you're off being an important and very busy Daddy.  I'm sure that pays dividends for you!

 
Rockford

There is always a risk.  I generally consider it a low risk.  But a risk none the less.

There's a big difference between OVERNIGHTS &  EVENING DATES.  

EVENING DATES:  Evening Dates are just 1 to 4 hours out of 24 hours.  

OVERNIGHTS:  Overnights are more then just 1 to 4 hours out of 24 hours.
                           Overnights are up to 24 hours.

I hope this helps explain everything. That's why females charge more.

... as a general guideline, the gents who post in this forum and who spend considerable amount of their time and resources in Sugar Bowl see a nuanced, but important difference between dating within sugar arrangement and booking a hooker to fuck.  

 
Sugar dates are real DATES, and they are rarely defined by "time multiplied by hourly rate." Quite the opposite.  The Sugar Daddy provides an allowance to his Sugar Baby in exchange for a comprehensive date experience which could last several hours, to overnight, to a weekend, to (at least for me) a month-long international vacation.  

 
Now I still book hookers from time to time, between Sugar Dates. And when I do, I fully respect her transparent pricing for her time, and enjoy the (hopefully) off the wall sex we have.  Nothing wrong with that at all.  But I don't look to a hooker for an emotional connection, nor the companionship, nor the mentoring and satisfaction I get from helping a young, inexperienced lady grow and mature as a young adult that I get when dating an 18-38 year-old Sugar Baby.  

 
So overnights, at least for me, are rarely about offering/negotiating additional compensation for additional "service." To be sure, some SB's might ask for more allowance to offset the earnings they may miss from work, or (I must admit) another Sugar Daddy.  When that happens, we can certainly negotiate what makes sense for each of us. But it's more typical for my SB's to like the idea of staying overnight if they can and want to so they can enjoy the additional companionship, affection, attention, and, if this 60-year old guy can manage it, enthusiastic morning sex.  

 
I hope this explains everything. That's why Sugar Babys are not hookers (unless they are - which happens).  

 
Life is good

 
The Cat