"Sugarbabies" / "Arrangements" Amateurs or Not?

**CantWinLosin** · 11-15-12 23:08

Nando, I'm probably a little more sensitive about the seen-in-public thing because I have a public presence in my community. People that I don't know, know me, much less the people I do know. And this is small-town southern livin', and Mrs. Grundy is always ready to spread the gossip around, so I'm kinda paranoid about it. I know a couple of other SDs in real life here that have that same sort of concerns, and thanks to their need to travel quit a bit, are able to restrict their play to out-of-town. I don't have that option, unfortunately.

But the good news is that I met a really amazing new SB last night, and she's old enough that we can be seen perfectly safely. Late-30's (she doesn't look a day over 30 in the face but does dress and act her age, very classy) and absolutely smokin' hot in every respect, and a walkin' talkin' ball of sex. We clicked thoroughly, to the point that she jumped me in the car in the parking lot after dinner. First really exceptional meet I've had from SA in a year or more.

**Hernando** · 11-15-12 16:10

I have been totally paranoid as a married man in keeping sub rosa. It is very hard to start a solid relationship with a sb which will stand the test of time without revealing most of the truth about yourself. It is good to know you can trust that she is sane and not out to hurt you. Now that I am separated I am more forthcoming about myself. As a single guy I would not think that there would be much blowback from public disclosure that you are dating younger women unless you are a pediatrician at 60 dating an 18 yr old. It might get your patients moms talking.

Re: honesty in advertising. Once I develop a relationship I am emotionally involved in I do care about monogamy. While there is no way to monitor this there has to be some trust between the two of you about expectations. I do not want my SB who I am caring for out there banging other guys as well. If they are for money then that smacks of prostitution. I have nothing against that age old profession but if I wanted a working girl I would go there. As it stands if I have a relationship I want exclusivity.

**HappyKampr75** · 11-15-12 10:04

Originally Posted by BigTigger [View Original Post]

My Advice.

It it obvious she cannot handle the realities of the situation. I understand your sense of honesty, but in this case, you don't gain anything by being honest. There isn't a reason to bring these items up. Enjoy the moment and enjoy the time with her. It's important that she believe the dream and is able to fully get herself into the fantasy that comes with this type of relationship. So either avoid talking about certain topics or lie about them.

You are not trying to marry her and who wants to know the exact end date of relationship. Even if you know, you will have much more fun the happier she is and the more blissfully ignorant you keep her. I'd rather have months or years of great awesome sex with a young hottie and just deal with the fall-out of a sudden break-up. If you are smart, it doesn't even have to be sudden, once she graduates, she may drop you. But always consider the words and the positives and negatives that come with them. In this case a happy blissfully ignorant SB will keep you happier longer.

On the first part, why the hell do you care what other people think? Dude get over it. Especially since the age difference is so small. I'd rather people that don't know me think I'm up to something as opposed to the negatives that come with giving a SB my credit card. I'm guessing that also means you are not using a pseudo either. So, now she has your information, credit card info, real name, etc. You are no longer in a position of control and that's not a good place to be with certain SBs. My money and my private life are much more important to me than what some people I don't know think about me. And even if they were right, that's cool too!

Ditto HollyWood!

BigTigg. Out!

You are right, I haven't been as secretive as I could be. Mostly because I'm single. I do not have a wife or family to worry about. I do however have a career I care about. For this reason I am going to start increasing security measures. I will watch other posts for a few days, seems like good advice gets passed around on the subject. Maybe use a nick name with future SB's.

As for credit cards, I was thinking of getting a prepaid card from my bank. Thus limiting her spending to as much or little as I am comfortable. I still feel embarrassed in public, bit that is an issue I will face when I am a little more experienced.

As for honesty, I think she should disclose any male companions, . Or am I too controlling here in this area? I have tried to be fair and forth coming with her. I see the wisdom and agree in not sharing the relationship has an expiration.

Thanks for the advice.

**Graham111** · 11-14-12 23:45

SB1 and I went shopping for a new pair of Jeans. Hers. At an upscale fashion boutique. I went into the dressing room with her and as soon as she slipped off her currents, and the thong visual set in. She backed up to me for a rubbing session which became a FS session. I was too paranoid for major fun but the staff must have known and just stayed away. Next week we tried the Hilton hottub. Again too paranoid for me but she seemed to have a really good. Alas we flamed out and after 6 months subsequent rendezvous to get back the connection proved no good (for me). You move on. It's complicated."You know nothing John Snow"

**EuroInCincy** · 11-13-12 17:35

Originally Posted by John G Smith [View Original Post]

Interesting conversation.

BTW, has anyone ever got it on in a dressing room? I saw some porn with some couples getting it on in a dressing room (mostly Europeans) and I was wondering if any members here have attempted it with their SB in a department store? I wonder if that fantasy is feasible or if I should just let it die.

Why a fantasy. I have gone to an erotic shop, buying a corset for her, and since it had to be laced up I just stepped in. If there were looks, I must have been blind.

Did the same at a Macey's some dresses. The 'attendant' gave me a jealous look when I came out, he did whipered loud enough that I could hear it "lucky dog" so I turned around and said nah no luck just know how to play your cards.

**CantWinLosin** · 11-13-12 15:58

Originally Posted by WoodSlinger [View Original Post]

Check out WhatsYourPrice. Com. Interesting concept.

I've checked it out, but haven't engaged anyone from there. The first couple of women that approached me there are well known higher-priced escorts (one of which I visited a couple times about a decade ago) , and the others are women I've seen on PlentyOfFish and other traditional dating sites that don't seem to have any clue what a sugar relationship is. I also really don't want to encourage the "I can get money just for showing up" mentality from the girls. And maybe I missed it, but they don't seem to offer any way for you to talk to a girl without at least making some dollar-amount offer to her for a date. What if I want to negotiate first?

There are a lot of women from my area on there, but almost none with recent logons, which tells me that the men have not been biting on this concept. I'm betting this will fail pretty quickly, but I could be wrong. Have you had success there?

**WoodSlinger** · 11-13-12 15:16

Check out WhatsYourPrice. Com. Interesting concept. You offer attractive females cash to go out on a date with you. I have zero experience in connecting with anyone on there, have only setup a profile with private pics. Wondering how well it might work. I recognized some of the girls I have talked with on SA by their profile pictures.

Anyone here using this for baiting in the SB's? They also have a variety of types of encounters you might be looking for. Married but looking, Open relationship. Etc.

**Hernando** · 11-13-12 14:17

As many of you know from my previous postings my ex-SB of 1+ years lived 2 hours away and we each drove 1 hour to meet in the middle. I felt very secure with this arrangement because of the safety factor. You never know who you will meet in the oddest places but distance is a good thing. The down side is the hotel rental. I always hated giving the $1000s of sugar for the room. There were multiple decades difference in our ages and most people did not stare, but one homely 50 yr old wife did a 180 in Starbucks and started slugging her husband in the arm. It was hysterical. I did a little bend me down kiss just to give her something to tut tut about. Poor husband was probably wondering how he can get in on the program.

I now have a lovely new SB and so far everything is going well. The only worrisome part is that she is local and we go to out of the way but local places to eat and drink. Even though I am separated I still have to be discrete. So I worry about discovery. I need to find some places that are a little out of town so that I can relax a little more. I never have any concerns about people disapproving of my GF, s age. Too bad for them. The ladies feel threatened and the guys are envious.

**Gigabyte40** · 11-13-12 09:39

Originally Posted by John G Smith [View Original Post]

Interesting conversation.

I'm in my 30s and I can still pass for late 20s on a good day, so it doesn't look too out of place when I'm in public with a young 20 something SB.

However, since I'm married I do have to be careful about being out in public with a young women too close to home. You guys heard me complaining a month or so ago about wanting a SB in my local area. But now I appreciate having a SB that's over a hour away in a city I have no ties to. It means I can take her out without having to stress about being spotted by someone I know.

Hell I know a guy that's a little over 50 and he takes his 19 and 20 yr old SB's shopping and out to eat. He doesn't worry what other people are thinking because they can easily pass as his daughters, niece, or even GRANDDAUGHTERS! But he does prefer to go out of town where nobody will recognize him.

**John G Smith** · 11-13-12 09:31

It's been awhile since I've posted an update on my own SB activities. I've been heavily involved with my 6/6 SB (yeah I upgraded her). She managed to be a keeper. We've met several times and keep in almost daily contact. She's hot, has a great personality, and very sexual. I decided that I'm pretty much going to devote 80-90% of my sugar resources toward her. I definitely could see the possibility of getting e-involved with her at some point but I'm still just enjoying things now. She's also bi, so although she hasn't brought it up, I'm sure there's a possibility of some additional fun down the line. I'm looking forward to seeing this last a while. She's not only great in bed, but we have excellent conversations on long car rides and such. So it's easy to be around her.

Even though I've been mostly focused on my 6/6 SB, I still had some outstanding business to take care of. I had a local "hookup" SB who was still on my payroll. We would basically meet late at night for car dates once a week. However the past month, she kept calling me to setup late-night meets, but she kept falling asleep at the last minute. My work days are already long, so after 3 consecutive failed / delayed meets because she fell asleep, I finally told her the next time I see her I wouldn't be giving her an allowance as penalty for wasting my time too many times. I told her she would just have to meet me once "on the house" and then things would go back to normal if she could not fall asleep anymore. But she balked at this, so I gave her her walking papers. She was a 19 year-old I had been seeing since the summer, but it was time to end it. I was only seeing her out of obligation mostly lately. She had zero passion in our romps. She's at school and lives at home, but in a couple of years if things don't go well for her, I could easily see her on BP. She already has the mechanical mindset needed.

So I'm down to one SB and I think that's how want it to be for now. I don't have any active accounts on any sugar daddy sites either. Let's see how long this lasts.

**John G Smith** · 11-13-12 08:59

Interesting conversation.

I'm in my 30s and I can still pass for late 20s on a good day, so it doesn't look too out of place when I'm in public with a young 20 something SB.

However, since I'm married I do have to be careful about being out in public with a young women too close to home. You guys heard me complaining a month or so ago about wanting a SB in my local area. But now I appreciate having a SB that's over a hour away in a city I have no ties to. It means I can take her out without having to stress about being spotted by someone I know.

All the other advice given by the members here is sound. But don't worry, I made some similar mistakes with my first SB. I also gave my real identity to my first SB. I got lucky that she was a girl who was from a rich family and she just wanted to be pampered and go shopping since her parents reduced her allowance. She had no interest in blackmailing me since it was a good chance her parents made more than me. LOL.

But yes, clothing shopping can be a bit awkward at times. Especially if the store is cramped and there's no place to sit. Then you're just following her around as a moving clothing rack. It's always a lot more fun when you can pick out the outfits for her, but most girls will still want to buy a couple of outfits that match their own taste.

BTW, has anyone ever got it on in a dressing room? I saw some porn with some couples getting it on in a dressing room (mostly Europeans) and I was wondering if any members here have attempted it with their SB in a department store? I wonder if that fantasy is feasible or if I should just let it die.

**Zomby** · 11-12-12 21:01

Originally Posted by BigTigger [View Original Post]

It it obvious she cannot handle the realities of the situation. I understand your sense of honesty, but in this case, you don't gain anything by being honest. There isn't a reason to bring these items up. Enjoy the moment and enjoy the time with her. It's important that she believe the dream and is able to fully get herself into the fantasy that comes with this type of relationship. So either avoid talking about certain topics or lie about them.

Well, I can certain sympathize with not raising the subject, I'm not convinced actively lying about something like that is going to be productive. I personally have a preference for as much honesty as possible. I'll withhold information and proclaim "none of your business", but I don't see any reason to lie to her.

As for an expiration date, I might not have been as blunt as the OP on the subject, but neither would I have made any secret of it, especially if it was important to me, which I can't honestly say it would be. My experience has no doubt left me biased, but I'd want to maintain a worthwhile relationship for as long as possible, and not place any bounds on it. As I've told my SB on multiple occasions, one or the other of us will know when it's over, so don't be afraid to address it when it happens.

Again, I've had a total of one sugar baby in my entire life, and it's lasted longer than many others' here apparently have, so mine might not be the most strategically correct opinion on this subject.

Originally Posted by BigTigger [View Original Post]

On the first part, why the hell do you care what other people think? Dude get over it.

As a married man, I think I can probably answer that one. I don't want to be noticed, and to be frank, she doesn't really want to be seen with me in public, either. One of the reasons neither of us complains about the long drive we have to meet is because it's less likely that we'll meet someone who knows us. Not impossible, but less likely.

/z

**CantWinLosin** · 11-12-12 20:39

Originally Posted by HollywoodGuy [View Original Post]

Dude I am 58 and date on average 22 year olds. You think I give a shit about people staring.

I can certainly respect the guys who feel this way and live where they can carry it off. But this ain't Hollywood; many of us live in small-town-bible-belt style America and have public lives. I'm noticing that it's becoming pretty rare that I go anywhere around here without running into someone I have social / civic connections to. Doing that with a girl half my age (that isn't one of my daughters) could be a real problem for me, and I'm not married. The married brothers here have even less freedom in that way than I do.

A lot of these younger babies simply don't grasp that. The media has pushed this titillating image of sugar relationships being all about a rich guy showering some sexy young girl with gifts and taking her to expensive places and fancy events on his arm, and more and more of this latest generation of younger SBs have swallowed that myth hook, line and sinker. When you explain to them how this really works, they get offended, not only because they don't want to feel like a hooker but because they feel lied to, either by you or by Dr. Phil.

I've pretty much given up on anything younger than 30. They may not always have that tight young body, but they know how the world actually turns and are far more realistic. They also tend to be less demanding financially, and they appreciate it more.

**BigTigger** · 11-12-12 20:04

I'm not sure if it came out the right way. I meant to say "Ditto what Hollywood said!"

Originally Posted by HollywoodGuy [View Original Post]

I am obviously so girl addicted I couldn't lie if I wanted to. LOL.

**HollywoodGuy** · 11-12-12 19:20

Originally Posted by BigTigger [View Original Post]

My Advice.

It it obvious she cannot handle the realities of the situation. I understand your sense of honesty, but in this case, you don't gain anything by being honest. There isn't a reason to bring these items up. Enjoy the moment and enjoy the time with her. It's important that she believe the dream and is able to fully get herself into the fantasy that comes with this type of relationship. So either avoid talking about certain topics or lie about them.

You are not trying to marry her and who wants to know the exact end date of relationship. Even if you know, you will have much more fun the happier she is and the more blissfully ignorant you keep her. I'd rather have months or years of great awesome sex with a young hottie and just deal with the fall-out of a sudden break-up. If you are smart, it doesn't even have to be sudden, once she graduates, she may drop you. But always consider the words and the positives and negatives that come with them. In this case a happy blissfully ignorant SB will keep you happier longer.

On the first part, why the hell do you care what other people think? Dude get over it. Especially since the age difference is so small. I'd rather people that don't know me think I'm up to something as opposed to the negatives that come with giving a SB my credit card. I'm guessing that also means you are not using a pseudo either. So, now she has your information, credit card info, real name, etc. You are no longer in a position of control and that's not a good place to be with certain SBs. My money and my private life are much more important to me than what some people I don't know think about me. And even if they were right, that's cool too!

Ditto HollyWood!

BigTigg. Out!

I am obviously so girl addicted I couldn't lie if I wanted to. LOL.