"Sugarbabies" / "Arrangements" Amateurs or Not?

[QUOTE=LoVecchio;3381010]I have been in the bowl for the last three years and have been amazed by the new vistas it opens up. I am in my mid-60's and have to confess that I've been having the best sex of my life with women 1/3 to 1/2 my age. Because I am married, I am limited to discreet meetings in hotels and have never tried to meet a baby when I'm traveling. A few weeks from now, I'm going to be going to a far-away city where I won't be so constrained and was thinking that it would be nice to meet up with an SB with the idea (well, my idea, anyway) of taking her to a very nice restaurant and then hoping to take her back to my hotel.

I'm at a bit of a loss in figuring out how to approach girls and also which ones to approach. I can't offer more than a one-time thing, because although I occasionally go to that city, I'm generally with my wife when I do so. I assume that it would be easier if I could dangle recurrent visits, but I can't really do that in good faith. So, I have to make clear that this is a one-time thing (or at least be careful not to seem like I'm promising more than that), which makes it hard to approach someone without offending her and making it seem like I am treating her as an escort. On the other hand, I don't want her to think that I JUST want a dinner companion. So, I'm having trouble figuring out how to approach a woman.

I'm also having trouble figuring out which women to approach. The choice seems to boil down to: 1) approaching the same women I would approach if I were trying to set up a long-term arrangement. These would be women who are educated or on their way to being educated and are people I think would be interesting dinner companions but perhaps far less than sure things to take back to the FC; or 2) approaching women who might be less educated, perhaps single mothers, who even if nice people might be less than enchanting dinner companions (and perhaps out of their element at a nice restaurant) but perhaps more of a sure thing to get to the FC because they may be more highly motivated by the money.

That leads me to the next thing, which is how to make it clear (or at least clear enough) that I am offering more than just a free meal if the night goes well.

Anyway, it seems that finding a Road Baby presents some different challenges from finding one close to home. If anyone has any advice, I would love to hear it.[/QUOTE]What I do is mention that I visit frequently (if you do, if you don't just leave it out), and that I'm just looking for a nice dinner, great conversation, and perhaps an amazing dessert.

I'm heading to a city I visit a few times a year later this week, and I have three women lined up for two nights. One is a definite freebee. The other two are TBD.

Be polite, but have an edge. You'll do fine.

[QUOTE=BaldEagle;3382838]I have had a few years experience on S. A. And I have found it to be a win, win situation for me and my S. B. s. I practice a few ground rules that have worked so far for me. 1 Under no circumstances do I tell them my real name. 2. I use a throw away walmart refillable phone I never use my regular phone. 3- Under no circumstances do I tell them my real name. I try to think with the big head as much as possible when I'm with a S. B. 4 - I don't wine and dine them ever. Many of them don't want to be seen in public, could create a lot of questions if a friend or family member see them. Maybe a coffee shop for the first meeting, after that its a private location or onto another potential S. B. There was mention of a girl named Summer in an earlier post, she attempted to blackmail one of us. I saw her about 3 months ago she was a normal pro. If they don't get personal info on you they can't blackmail you. , These S. B. s are smarter than we think sometimes, it is about the money. There are more and more pros, getting on S. A. , they do stand out, too quick to meet and they usually are available day or evening. Good hunting. One side note for anyone who has a significant other who is suspicious of your activities. Verizon has a new device called hum, it attaches to the computer port under the dash of your car and you can download an app on your phone to follow that car. I just found about it yesterday this could be old news to some, it was new to me. Beware.[/QUOTE]I've not heard of hum. Thanks! Lots of places have been selling GPS trackers with magnets in waterproof cases (put under the hood or wheel well) for a while now.

The long and short of it is if your SO wants to catch you. She probably will. It's all risk v. Reward.

I had the oddest conversation the other day with a young lady.

I usually avoid discussing allowance. The one exception is if the SB says she's had a SD previously. I usually ask what were the terms of the arrangement just to get an idea of her expectations (yes I know they most probably lie about the amount). This young lady gave me the amount and said that they usually stayed indoors for discretion. The amount she indicated was super high, and I said I can't do nearly that amount as I need to get a hotel room etc. Etc. Her reply was "I'm not a prostitute".

After I stopped laughing, I told her I didn't say she was and that I presumed she met her last SD in a hotel unless he was single since they stayed indoors. She replied that he was married, but they'd meet at his house when the wife was at work. I told her that won't work for me, and I wished her luck.

I have to say it was the oddest conversation I've had on SA, and that's saying something!

I don't know how many of you have followed the cheerleader / SA story in the news, but here is one media story that is probably good for the lifestyle, in contrast to all the recent negative press.

Good move by Brandon Wade.

"The operators of a dating website reportedly used by members of Coastal Carolina University's cheer-leading squad will be reaching out to the cheerleaders' attorney to offer to pay for legal fees following the team being suspended indefinitely. ".

[URL]http://www.wmcactionnews5.com/story/35098582/operators-of-dating-website-offer-to-pay-legal-fees-for-ccu-cheerleaders[/URL]

[URL]http://www.teenvogue.com/story/college-suspended-cheerleaders-for-allegedly-being-escorts[/URL]

I have been texting with this girl and she wants to meet. She looks familiar but I can't place her. Anyone?

[QUOTE=BikeRider;3383446]I had the oddest conversation the other day with a young lady.

I usually avoid discussing allowance. The one exception is if the SB says she's had a SD previously. I usually ask what were the terms of the arrangement just to get an idea of her expectations (yes I know they most probably lie about the amount). This young lady gave me the amount and said that they usually stayed indoors for discretion. The amount she indicated was super high, and I said I can't do nearly that amount as I need to get a hotel room etc. Etc. Her reply was "I'm not a prostitute".

After I stopped laughing, I told her I didn't say she was and that I presumed she met her last SD in a hotel unless he was single since they stayed indoors. She replied that he was married, but they'd meet at his house when the wife was at work. I told her that won't work for me, and I wished her luck.

I have to say it was the oddest conversation I've had on SA, and that's saying something![/QUOTE]You absolutely did the right thing by wishing her luck. I know you said you usually don't discuss allowance but I would encourage everyone to "never discuss allowance." In this instance you may have lost a good POT by going down the road of discussing (negotiating) the allowance up front. Believe me I know how this goes bc my first year in the bowl I used to do the same exact thing. However, I have learned to simply stick with JL's approach on the discussion of allowance. Frankly at the end of the day it does not matter if they had a SD previously. Asking her about the previous arrangements only gives her an opportunity to embellish (lie) so her answer is moot. Doesn't matter bc it is no doubt bs anyway and worse, starts her down the road of lying from the get go. Moreover taking her high dollar fib and then putting the hotel factor into the convo continues to make it a negotiation. You don't want that. What you want to do is strictly side step the $ topic and never give a definitive ($) answer. If you give her an answer to the $ topic then guess who is in control. It ain't you. Just sayin. They either go the hotel room or they don't. If they do then a few minutes before she leaves put an an envelope with a nice card (I purchase very appropriate cards at a boutique card shop) into her purse. If the SB is worth repeating I put in 200 (a ben franklin and a 100 visa gift card). If she isn't worth repeating or is in a very rural area then a Grant and a 100 visa card. If she ghosts me after that then so be it. But she is a fool if she does bc I always make sure they have a good time. BTW as far as her story about meeting at the guy's house, she is either lying or IMHO the SD is a damn fool.

[QUOTE=StormyTuesday;3386410]You absolutely did the right thing by wishing her luck. I know you said you usually don't discuss allowance but I would encourage everyone to "never discuss allowance." =* * * * I have learned to simply stick with JL's approach on the discussion of allowance. * * * * What you want to do is strictly side step the $ topic and never give a definitive ($) answer. If you give her an answer to the $ topic then guess who is in control. It ain't you. Just sayin. They either go the hotel room or they don't. If they do then a few minutes before she leaves put an an envelope with a nice card (I purchase very appropriate cards at a boutique card shop) into her purse. * * * * [/QUOTE]This is an area in which I have a hard time adhering to what I acknowledge is sound advice. So, if she raises the issue at the M&G, I usually give a number. I figure that if I don't, there are two possibilities: 1) she declines to go forward in the absence of a commitment about the amount; or 2) she goes forward but then has to be worrying the whole time during the date if she is going to get stiffed (the wrong way). I actually worry more about number 2 than about number 1. There are enough sketchy guys on the site that a woman has to be wondering what the ultimate outcome is going to be. I think I give off pretty trustworthy vibes, but a wise SB is going to know that the most successful con men (not to mention people like Ted Bundy) do also.

[QUOTE=StormyTuesday;3386410]You absolutely did the right thing by wishing her luck. I know you said you usually don't discuss allowance but I would encourage everyone to "never discuss allowance." In this instance you may have lost a good POT by going down the road of discussing (negotiating) the allowance up front. Believe me I know how this goes bc my first year in the bowl I used to do the same exact thing. However, I have learned to simply stick with JL's approach on the discussion of allowance. Frankly at the end of the day it does not matter if they had a SD previously. Asking her about the previous arrangements only gives her an opportunity to embellish (lie) so her answer is moot. Doesn't matter bc it is no doubt bs anyway and worse, starts her down the road of lying from the get go. Moreover taking her high dollar fib and then putting the hotel factor into the convo continues to make it a negotiation. You don't want that. What you want to do is strictly side step the $ topic and never give a definitive ($) answer. If you give her an answer to the $ topic then guess who is in control. It ain't you. Just sayin. They either go the hotel room or they don't. If they do then a few minutes before she leaves put an an envelope with a nice card (I purchase very appropriate cards at a boutique card shop) into her purse. If the SB is worth repeating I put in 200 (a ben franklin and a 100 visa gift card). If she isn't worth repeating or is in a very rural area then a Grant and a 100 visa card. If she ghosts me after that then so be it. But she is a fool if she does bc I always make sure they have a good time. BTW as far as her story about meeting at the guy's house, she is either lying or IMHO the SD is a damn fool.[/QUOTE]I do sometimes ask (usually in an indirect way) about their previous experiences in the bowl, partially because I'd just like to see what she says. I don't expect honest answers, most females are elusive and downplay all past sexual experiences anyway (she might for instance say she was in a platonic arrangement when it was really much more than that). When I do this, its usually only because I want to lay the groundwork to talk about my own expectations (again nothing involving numbers). The expectations I want to let her know about often relate to my travel schedule, to make sure she understands that both of our time is valuable, and to be sure she won't engage in flaky behavior and then not show up after we have a date.

Sometimes they do take this as some sort of request for prior gift amounts and use it as an opportunity to tell me what their previous SD gave them or did for them, which in most cases I automatically assume is exaggerated, but above all I do not respond to the number aspect of what she says. Sometimes they push to ask about that, sometimes they don't. The ones that push about gift amount (either what I give them or how much I've gifted in the past) are not invited to a M&G with me, so the problem corrects itself soon enough.

As an example of how my question about past SDs can head down the number road yet still be fully workable, I once met a very nice, early 30's MILF with a good job and strong sex drive. When I asked her about prior SDs, she said her prior SD was a married guy that she spent about one weekend a month with and he would give her $500 on the last morning of the visit. I was thinking to myself that was very reasonable considering getting full use of her body for a whole weekend! But I didn't react to the amount or even acknowledge it, and it wasn't long after throwing the $500 number out there that she basically clarified that this was just what he liked to do, and that she wasn't saying she necessarily expected same amount or arrangement from me because she wasn't just in it solely for the money. So it can work both ways.

I just use whatever conversational tactics make sense for the particular situation to determine if she's going to be a PITA or GPS girl, or the type that will make daddy happy.

[QUOTE=LoVecchio;3387027]This is an area in which I have a hard time adhering to what I acknowledge is sound advice. So, if she raises the issue at the M&G, I usually give a number. I figure that if I don't, there are two possibilities: 1) she declines to go forward in the absence of a commitment about the amount; or 2) she goes forward but then has to be worrying the whole time during the date if she is going to get stiffed (the wrong way). I actually worry more about number 2 than about number 1. There are enough sketchy guys on the site that a woman has to be wondering what the ultimate outcome is going to be. I think I give off pretty trustworthy vibes, but a wise SB is going to know that the most successful con men (not to mention people like Ted Bundy) do also.[/QUOTE]Your pretty well on point with this. At the end of the m / g if we both want to go further then we discuss the arrangement. Every person has self worth and if they feel that they had a say in the process then that's one less thing to be worried about and makes for a much more enjoyable time for both. This giving what the guy deems she is worth at the end of the fc usually turns out to leave a bad experience for the sb. Lots of predators play these girls giving them nothing to robbing them and moving on to the next without seeing them. Girls who have never done this before are easy prey thinking that they are going to be mutually benifited at the end of the fc and receive little or nothing. At the end of the m / g if their expectations are to much I just simply reply that I will consider it. Then the ball is in her court, she can try to negotiate or hold firm. At the end however it goes she had a say in the process and is a happy camper and so am I. If one is trying to do better than escorts why short change a girl. No escort allows you to decide afterwards what she is worth so this tactic is just taking advantage of a girl IMHO.

Anyone have an intel on this SB in Richmond?

[URL]https://www.seekingarrangement.com/member/60c75684-83c6-4d1a-b964-1a429e4bad81[/URL]

I am looking at a huge # of POTs these days because I am on a hall pass, and I think I am beginning to develop a sense about which are submissive from their looks. Does anyone else have a sense about this? Here is a profile that I think has 'the look'.

[URL]https://www.seekingarrangement.com/member/c0fea8e6-e101-4e28-bdb0-7a644ae627e8[/URL]

Some are bold about saying it in their profiles, but many aren't. How about those who say they are shy?

When I can't get a response out of a girl initially, I have followup messages I use, and the one that most often gets a reply is about how they are naughty and asking if they want to be directed. Truly it is my go-to strategy to get a specific girl. I did this w / a girl today who really showed no hint in the profile of being submissive, but came right back saying that she was but she wasn't able to find a man on SA who would be dominant. Obviously, she didn't try very hard.

I am debating w / myself about what to do w / a girl I stumbled upon. She's 20, a fat asian. Her profile is all about being taught, and in messaging she has admitted she is a virgin, in fact never kissed anyone. I pretty much believe this. I am debating w / myself whether I want to go to the trouble. She would be had for little to no sugar, but her skills are questionable, and no visual benefits.

I couldn't do it. Enthusiasm and attitude are important, but looks and skills are deal breakers. I don't judge, so report back and let us know how it goes.

[QUOTE=FarFarAway;3389808]I am debating w / myself about what to do w / a girl I stumbled upon. She's 20, a fat asian. Her profile is all about being taught, and in messaging she has admitted she is a virgin, in fact never kissed anyone. I pretty much believe this. I am debating w / myself whether I want to go to the trouble. She would be had for little to no sugar, but her skills are questionable, and no visual benefits.[/QUOTE]

I also like submissive women. Some straight out express an interest in being submissive, dominant men, bdsm or ddlg. Other clues are saying they are shy and want to be taught or expressing an interest a confident man who likes to be in control. I've also found a high percentage of women that wear chokers in their pics are also submissive.

I say I am naturally dominant in my profile and I get women ask about that when they message me. LOL.

I'm curious what others have noticed.

[QUOTE=FarFarAway;3388741]I am looking at a huge # of POTs these days because I am on a hall pass, and I think I am beginning to develop a sense about which are submissive from their looks. Does anyone else have a sense about this? Here is a profile that I think has 'the look'.

[URL]https://www.seekingarrangement.com/member/c0fea8e6-e101-4e28-bdb0-7a644ae627e8[/URL]

Some are bold about saying it in their profiles, but many aren't. How about those who say they are shy?

When I can't get a response out of a girl initially, I have followup messages I use, and the one that most often gets a reply is about how they are naughty and asking if they want to be directed. Truly it is my go-to strategy to get a specific girl. I did this w / a girl today who really showed no hint in the profile of being submissive, but came right back saying that she was but she wasn't able to find a man on SA who would be dominant. Obviously, she didn't try very hard.[/QUOTE]

[QUOTE=Madaboutmax;3390893]I also like submissive women. Some straight out express an interest in being submissive, dominant men, bdsm or ddlg. Other clues are saying they are shy and want to be taught or expressing an interest a confident man who likes to be in control. I've also found a high percentage of women that wear chokers in their pics are also submissive.

I say I am naturally dominant in my profile and I get women ask about that when they message me. LOL.

I'm curious what others have noticed.[/QUOTE]Well, I didn't say I liked them, particularly, but after a year I've found I can't play in the bowl without being aware of this particular kink. Someone listed 'little girl' as her occupation, and when I asked her at the M&G if she was submissive, she said she wasn't getting many contacts, and her GF offered to 'fix' her profile so she'd get some more. And that's where it came from.

Of course, those discussing 'teaching', etc., are candidates. I hadn't keyed into the choker thing. Certainly I've seen some pix that include leather chokers and I figured they were kinky, but there are quite a few profiles where the girls have these chokers that look like they are a necklace or ribbon or something similar. Do you include that in your evaluation?