OK, this is probably my third or fourth last stupid question, so count on many more. When do present the gift to your SB?  Typically in the non-sugar world, one places an envelope with the gift enclosed in plain sight upon meeting the provider. When and how do you present the gift to your SB?  At the beginning of the date, at the conclusion of the date, or at some other opportune moment?  Also, do you put it in a card, just an envelope, some other method?  

The SB (my first) and I are going to lunch on Wednesday. I brought up going bcd after lunch, and she said she might be able to do that, but she’s dog-sitting, so she might not have time for bcd time. I’m hearing bells seeing warning lights. I don’t think I want to present the gift at the beginning of the date as I’m pretty sure that would guarantee no bcd time because of the “dog.”  But if I wait until there is some bcd time, then it feels a little like just a transaction.  

Please advise, my Brothers!

Please try to do some mind-shift here. You are going on a date, not scheduling a fuck session with a hooker.  

 
Treat it and her like a date. Meet for lunch, engage in some conversation and bonding, then invite her to join you for more intimate fun.  Keep it light and be the confident older, mature guy that you are.  

 
If she likes you and consents to shag, then hand her a gift when you part. I never hand cash to a SB, especially in public.  Too hooker-ish.  On a first date, I typically put cash into colored envelope with a blank note card.  On subsequent dates I will either ask her if she has and is comfortable with Zelle, CashApp or similar. If she (or you) are not, hand her a plain white envelope as she is slipping out the door, then give her a hug and let her know you can't wait to see her again soon.  

 
If her dog issues (that's really just her graceful exit option) prevent her from the next steps, wish her well and let her know you will contact her soon to set up another date. She can text you later with her intent to bail or continue. You can do so as well.  

 
Keep it light - this is a casual date with a cool babe. You can be happy to spend time with her, and if it doesn't go further, no worries. There will other opportunities soon.  

 
Life is good

 
The Cat

I haven't done cash in what, a decade?  The newer babes understand electronic transfers LOL

Tell her to bring the puppy - however, they due tend to bark alot while you're banging her, so that's a negative.

My #1 SB also supplements her income with house sitting and pet sitting.  It's a real thing.  Her last clients came home a few days early, and she immediately rescheduled our next date a few days earlier as well.  I always give my SBs a gift of cash, as they are leaving.  We make a fun game of it, where I'm supposedly trying to find a pocket on her clothing to discreetly slip the $ into as we're having a goodbye hug.  But since she has no pockets, I have to roam  my hands all over her body trying to find one.  Last time, she lifted her shirt so I could slip the $ into her bra.  Fun!  Other times, if we're sitting across from each other having coffee and conversation after our bedroom activities.  I'll just take the $ out of my pocket and casually slide it over to her, or slip it under her purse, something obvious where she'll see it.

One more thought about paying upfront.  If you get a newbie SB she may have gotten bad advice from any number of sources.  She may ask for, and expect, payment in advance.  If necessary, I will say, look, I know you don't think of yourself as a sex worker, or escort.  And I don't want to treat you like one.  Paying upfront is escort protocol, not sugar dating protocol.  I'll never actually pay you!  But I'll always give you a cash gift when we say our goodbyes.

I always give the gift in a nice envelope and card discreetly tucked under her purse after intimacy before she leaves. I never hand money to her or in any way make it seem like a hooker-john meet. Everything that Herb said is right on the money, so to speak, with the exception of the electronic transfers for future dates.  

 
For me, I keep it cash even for long term arrangements. If you set up a payment option electronically it's more convenient, but then she will inevitably at some point find herself in desperate straits needing you to pay her late rent or her about-to-be-repossessed car... or her poodle needs an emergency tail transplant... or... [fill in 'emergency' here]  

 
Having a convenient electronic means to bail her out of whatever mess she's created for herself [fictional or non-fictional] will only facilitate you and your hard earned money to be prematurely parted. [And no pussy to show for it]

 
Keep it cash is my advice and never give it up front, not ever.    

 
I'd also avoid the dog scenario as much as possible, it is indeed a convenient exit strategy for her. She needs to be as focused on meeting your needs as you are on hers without the added distraction of a jealous doggie. Pets are wonderful but not in the bedroom.        

-- Modified on 7/12/2025 12:40:36 PM

Great advice, guys, as always. Early on in our messaging, she went dark on me for a few days and told me her periods are Hell and told me Uber Eats would be nice. I told her my alcoholic wife watches the credit cards and electronic transfers like a hawk, so I would need to keep it cash only. We talked about it again during our M&G, so she knows it will only be cash. She understood. I think Herb nailed it with making sure to stay far away from the escort/john vibe. You all reinforced that and gave some great tips, too. I’ll let you all know how it goes.

So…she sent me a message last night to let me know she might need to postpone the date due to stomach issues from drinking whole milk and being lactose intolerant.

First question:  Who drinks whole milk when they are lactose I tolerant?

This morning she messaged that she wasn’t 100%, she felt better and would still like to go to lunch as planned. I asked about bcd time, and she said probably not. I gave her the benefit of the doubt and agreed to lunch.  

I licked her up and we talked a little before I started toward the restaurant. I told her I didn’t know what to do about her gift. She said she did t expect me to give her a lot of money today. With that in mind, we headed toward the restaurant. It wasn’t a really nice place. She had chosen it earlier. Lunch cost me $55.  At the end of lunch, she asked me if I might be willing to buy her a cheap dress for a foam party she has coming up. I said I would. I ended up buying her two dresses that totaled up to $85. We went to one more store and I bought her a few accessories for about $25. So, I was out a total of $165 - about half of our agreed-upon ppm rate of $350.  

We had a lot of fun and got to know each other better. I actually like her a lot, and having her model dresses she was trying on was quite sexy - felt a little like Pretty Woman. We did kiss when I dropped her off and agreed to meet again.  

Remember her previous concerns about leaving the dog she was watching alone for too long?  Never came up.  

Question 2:  Am I a freaking idiot?  

Question 3:  Would you go on another date with her?

Not what I had in mind for my first sugar date.  

All opinions and advice welcome - as always.

You're being very generous with her, considering you haven't had any BCD time.  Mot of us here have learned the hard way that girls who expect or take that kind of generosity upfront, never give you what you're seeking.  So we never pay for more than lunch upfront.  But she might be appreciative and show you so in the best way.  Could happen, right?  So are you a freaking idiot? No, just a normal idiot horny male thinking with his little head.  And should you go on another date with her?  As long as you give her nothing more before she gives you some pussy, why not?  Might have a happy ending.

My allowance is cash only, and always in an envelope. I like to use envelopes that reinforce my image.  

 
I travel all the time, mostly to nice places, including sometimes overseas. I make sure to acquire a small stack of hotel envelopes at each place and I use those envelopes for allowances. So when I tell my baby I stay at nice places in fun cities, my envelope underscores that message. Most recent reaction: "You didn't tell me you went to Warsaw, too!"

 
And regarding the dog ... I just don't. In fact, I cut if off with one chick who kept a large dog nearby during our rendezvouses at her place. The dog was no trouble, and I didn't mind him "watching," but she made a point to repeat that the dog is "for her protection." That didn't sit quite right with me. I would be no match for the dog if it decided I was a threat. I got to thinking it was like a girl telling me she'd fuck me but only with a loaded gun on her nightstand "for her protection." Not the vibe I have in mind.  

 
Rockford

Good call to bail.  Having the dog there wasn't her real issue. Telling you repeatedly that she needs protection means she has significant trust issues, especially with men. Those issues may very well be valid if she's been abused in the past. But it's not your place to provide therapy for her issues.  

 
Arrangements/relationships are built on a foundation of trust and consent, within the boundaries of your mutual agreements. Her trust issue would eventually erode the quality of your relationship with her and lead to very unpleasant endings.  

 
Disclaimer: I have two cats and it's not unusual for at least one of them to be in the room for my BCD times.  But they aren't there for my protection. They are there because my SB's think they're cute.  

 
Life is good

 
The Cat

Run.  Fast.  Don't buy her shit till you get what you want as well.  She used you for free food and clothes.  And she's probably trying the same thing on 50 other guys at the same time.

"Most of us here have learned the hard way that girls who expect or take that kind of generosity upfront, never give you what you're seeking."

This is called a shit test.  Can she get you to spend on her without sugar?  

 
In this case, it was not very much money. And that is part of the test.  Lunch-$55, no problem. But the dresses were her bait to see if you would bend and simp out for a totally useless ask.  Foam party? She's going to ruin two brand new dresses at a party? She doesn't have ANY dresses in her closet now that she can use? You funded a "want" not a "need." And now she has seen that you can be manipulated to spend on her for no return (a goodbye kiss in the car doesn't count).  BTW: Which guy(s) at that foam party will she be banging once she's flaunting her skin-tight wet new dress and drunk? Now she can fuck anyone she wants, of course. But do you want to pay for her wardrobe when she does it?  

 
Lesson: It's ok to say "no."  When she's asking you to do something beyond your rules, be the adult and tell her no. Don't be mean or rude. Just explain something like: "Sounds like a fun party, but it's too soon for me to be buying gifts for you. We just met today and still need to make sure we are a good match. I'm sure once we go on our next date you will get enough allowance to cover new clothes. And I look forward to seeing you model them for me."  

 
That is flipping the shit test back on her:
1. It reinforces that you mean what you say.
2. It shows you want to continue to a formal arrangement.
3. It demands respect for your time and attention.  
4. It also reminds her "mutual benefit" means you get the benefits as well as her.  

 
If she reacts poorly (gets mad, accuses you of being cheap, try's to guilt you, etc.), then it's time to bail, with $85 still in your pocket.  

 
If she reacts well (says she understands, apologies, etc.), you have passed the shit test and asserted your role as the Daddy (versus the simp).  

 
The worst outcome that can occur from saying no is that she will move on. And if she does, moving on is actually the best outcome for you from a problematic POT.  

 
The best outcome is that she will respect you as you move forward and can then be truly grateful when you spontaneously (in other words when YOU decide to) buy her gifts in the future. And if she does, you both get the best outcome over time.  

 
Life is good

 
The Cat

I concur with this, Herb. I've applied this in my own situation recently with a difficult POT. A 'no' from Daddy is often more powerful than a 'yes' to her testing demands. Additionally, your 'no' to her can often act as a powerful aphrodisiac on her when applied with confident firmness and the willingness to walk away. While I don't agree in general with red pill psychology as I  think it does more hard than good, calling out her unrealistic demands in the right situation and being willing to say no and walk away usually yields the best outcome.

Thank you for all of your valuable advice!  I'm going to insist on the sugar first on our next date.  If she objects, then it's off.  If she accepts, then it's game on!

Yes, that is my formula. I don't meet with anyone who doesn't say she is down for BCD at first meet. If she demurs, then there is no first meet. I do that because I am only in her town for a limited time and I don't have time for some mythical, magical, magisterial "three-date rule," or whatever.

Soooo, the latest.  I had to delay a second meeting with my SB due to family issues.  They have cleared now, so I asked her to get together this week.  She was on her period Sunday and Monday of this week, so I figured things would be "cleared up" by today.  She said she could get together today.

I asked her if we could start with play time (since the last time we met up, she came up with "stomach" issues that she said would prevent her from feeling comfortable getting physical).  She responded by saying that she was on her period, but even so she never enjoys just going right into sexual acts.

I feel like I should break it off - she's not ever intending to get physical with me and just wants to see how much $$ she can get from me before she just disappears.

Am I right?

I do everything in cash! lol

This is a post that all sugar daddies should read multiple times. Herb and I are in the same geographic area and the number of POTs is simply astounding. I mean off-the-charts abundance. So this means that the SD should always "maintain his frame" and realize that the numbers are on his side. Be generous (however you define it), be fun, present and strong. But also be that wall that she may try to push up against but doesn't move. She'll either respect you more or move on to someone who is a simp. Either way, you win!

Remember, In vanilla dating pretty women are the scarce resource and dictate the market. In the sugar bowl, men with means (and balls) are the scarce resource and dictate the market.

There is little doubt that she is playing you for a desperate, sexless, simp. And she's just using the simp playbook to keep you interested without adding anything to the relationship.  

 
Never burn bridges, unless they are already on fire.
Rather than breaking it off completely, you can just put the ball back in her court (pun intended).  

 
Here's what I would do:  
Express empathy for her "condition" and her hesitation about "just going into sexual acts."  After all, you are a nice, caring and respectful guy.  You would never ask her to do anything that makes her feel uncomfortable.  

 
But it's time for her to make a decision, so let her the next move. Tell her to reach out when she's ready to have a full date; without allowance if she's not ready to commit to a full arrangement and wants to make sure she's comfortable with you (Note: don't agree to more than 2 of these additional dates), or with allowance if she is.  

 
Then - and this is CRITICAL - shut the fuck up.  

 
Do not send any follow ups, check-ins, "how ya doing", etc. messages. Total radio silence.  It doesn't matter if it's been a day, week, month or longer. No more messages. If she replies and tries to reset it back to "give me free stuff" mode, go back to your last statement: I am waiting for you to decide if you want to take the next step. Have you made a decision?  Then wash, rinse, repeat one (and only one) more time. After that, on her 3rd attempt, just tell her thanks but you have moved on to a new opportunity.  

 
If she replies that she wants full date with or without BCD, make your plans accordingly.  

 
If she doesn't reply, she's realized she has squeezed as much out of as she can and has moved on.  

 
Meanwhile, do not wait for her reply. Continue to look for and talk to new POT's. Use your time for your needs, not hers.  

 
Life is good

 
The Cat

Did you give her an allowance even though there was no sex?  If you did, she fucked you over.  Never pay her anything unless it's a full date.  If she isn't cool with that kick her to the curb immediately.

I'm on a PPM agreement with her.  On our first, an only, date, I paid for lunch and some clothes for her that came up to being around $180.  Our agreed amount for a full date, including BCD time, is $350, so I paid her about half.  I thought that was very generous.  I got a peck on the lips for it.

I just put the ball in her court as advised.  We'll see what happens, but I'm guessing I'll never hear from her again.  I'm OK with that.

You guys are awesome!!!

Man, they're hookers. The fact they don't think they are changes nothing. Hand them the cash when they're done with the hooker part.

I suppose if you want to be all classy about it you could put it in their purse when they're getting ready to leave. lol

You guys have seriously created an entire imaginary world for yourselves.