"Sugarbabies" / "Arrangements" Amateurs or Not?

[CantWinLosin]

I know the ladies like that "allowance" thing, but in my experience it is nothing but an invitation to get ripped off. Once they have the money in advance, they find all sorts of excuses why they can't keep their scheduled meetings. Both of my last two SBs - one 29, one 27 - did this.

Now, I tell them right at the beginning: no up-front allowance, and I tell them why (plus my work / life schedule can be difficult, so when I make time with my SB, if she backs out it's a major inconvenience.) Me buying them something or paying a bill after the fact keeps them interested and willing to keep scheduled meetings. I've had a couple say no thanks, and that tells me that they might well have done the same thing. But most are agreeable.

[Coolhand2]

Well CSB2 has ask me to make arrangements for a place where she can show me her "goodies" for our meeting on Monday. I'm viewing this as a request for a hotel room where I can sample the goodies. She also asked if she would be happy with her allowance. Not quite sure how to answer that since this is the first time the subject has come up. I sure want to keep her hopes up to increase her level of commitment and enthusiasm. One thing for sure; no goodies, no "allowance". Does viewing the money exchange as an allowance help them keep their amateur status? Wish me luck.

[Literal2]

It does take work and I think its like growing something, you have to keep tending to it. But the work can be fun too, sometimes. Let me see, who do I have on deck now? I think it's four. One is sb4, I'm hoping for at least a three-peat of my two wonderful fucks with her before she realizes she can get somebody with a lot more money and a lot better looking than me. I have to be ready for this. Another is a 34-year old artist-student type SB9 just saw her briefly in a bar once (she was way late) but she is very hot. I have a private date set with her, she may even be able to borrow a friend's place so she clearly expects to open her pussy for me and it looks promising but a week is a long time and that's not coming up until end of next week. Third would be another so called artist SB10, age 39, just divorced and broke, very needy, who wants to meet privately with penetration but insists on a multiple date commitment first. I think I will pass. Finally, there's the skinny blond smoker SB5 who is pretty, sort of, but a complete mess. She emailed me after pussy entry to completion to say she wants to meet more often. I'm not going back to her unless I get really horny. Plus there are several extra sb's kicking around, the best SB11 says she is 21, and just got back to me after we misconnected on a date out of town last week. She's very hot in her pix, a student, and she says she wants to know when I'll be back. So I will stay in touch with her, but I'm learning the odds and I doubt there will be pussy entry anytime soon. So it doesn't look like there's any SB pussy for Lit2 this week, but next week looks promising.

[Coolhand2]

Thanks for the data, Cool. Can I ask you is your housewife still married and living with the husband? Mine have all been divorced or single moms. Also, for the five that are ready to meet, have you discussed money yet? How do you handle it? Finally, are the meetings get acquainted meetings in public or are they meetings where you will be alone? Just curious.

She told me from the beginning that she is still married but that the husband was cool with everything. We set date, time, and amount of help over email outside of the SB site. Both meetings have been at her house; once in the evening and once in the afternoon. I know there is at least one child because she needs a couple of days notice to arrange work schedule and babysitting. Plus I see kids stuff around. There was no "get acquainted" meeting and she was dressed and ready for action when I got there. She has never mentioned money outside of the email which said what her expectations were. I put it in a visible but inconspicuous place before I leave. I do have to say one thing; I'm not sure there is a husband. I can't see a man's presence in the bedroom we use (although I don't get a lot of time to check it out) so it might be a cover story to make her feel safe.

Of the five that are ready to meet, time and place have not been set but I don't think there married. Two have said how much money their looking for and the others have not said anything about it. I do try to make sure they know that the SB site is not about the traditional relationship and that my expectation is for a discrete SB / SD experience.

I think you were absolutely right about the three types of women on that site. The housewife (CSB1) is in the first category of amateurs who needs financial assistance. I'm not sure yet which category the one (CSB2) I'm meeting next week falls into. I'll let you know the type of meeting it turns out to be when it's set. The two that have said the dollar amount (not yet worthy of designation) I think fall into the second category of semi-pro.

This whole SB thing takes a lot of work.

Coolhand

[Literal2]

Thanks for the data, Cool. Can I ask you is your housewife still married and living with the husband? Mine have all been divorced or single moms. Also, for the five that are ready to meet, have you discussed money yet? How do you handle it? Finally, are the meetings get acquainted meetings in public or are they meetings where you will be alone?

Just curious.

[Coolhand2]

I agree that if you want a sure thing you are better off with well-reviewed escorts. For me the excitement of the chase enhances the sex, but that's just me.

I understand the chase enhancing the sex. That was the main reasons I started on the SB site. According to their stats, I've emailed a hundred, received messages from 85, (somewhere between a third to half of those are unsolicited messages from out of state) and hit my home run on the one meeting that was actually set. I've seen her twice. Early thirties, not bad looking housewife type who is totally into the sex. I leave her $$ and she has always been very grateful. I'll probably see her at least once more but I'm ready for something new. I have five who say they're ready to meet and one I'm set to meet a week from tomorrow. Since my visits to the city are limited, I reserve one visit a month for an escort visit because that gives me both variety and certainty. If this meeting next week works out I'm going to substitute her for the escort visit, drop the housewife, and focus on expanding my circle of SB's. To this point funds have not been an issue but there is a limit for these type of activities. Thanks again for the info. Keep the updates coming and stay safe.

Coolhand

[Literal2]

I decided to take SB5 at her word and accept her offer to come over and fuck her which I did yesterday. Skinny but nice and tight and good oral skills. Smokes like a fiend and her place stinks of smoke. I can tell she's going to be clingy so I must execute exit strategy.

Later I met up with SB9 an artist / student type who I've been emailing for nearly a month. Bad news is she was late to our meeting at a bar and I was out of time so I just paid for her drinks and left. Good news is she is gorgeous. She has told me that if we agree to an arrangement she can use her friend's apartment to host. I'm hoping this one works out because that would give me two really fine girls to fuck, SB4 being the other one.

It was an active week for me with four SB's opening their pussies for my inspection and pleasure.

I was trying to figure out how long it took from initial contact to penetration in each case. Two girls spread their legs within a day or two of our first contact, but those were the heavy ones. Of the other two, SB4 was a repeat. Although by far the best so far, my first contact with her a few weeks ago was followed quickly by penetration within a few days. On the other hand, SB5 didn't respond to my emails on the site for many days and when she did she wanted to meet right away but she spent the first session talking about her restrictions so I walked out. So from first contact to penetration in SB5's case took at least three weeks and two visits.

I agree that if you want a sure thing you are better off with well-reviewed escorts. For me the excitement of the chase enhances the sex, but that's just me.

[Coolhand2]

Let me think. I started with the site in November. I search for 18-45 and recently began restricting by body type. I have probably contacted 60 to 70 girls by this point and received replies from 20 or so. I've seen 7 and been stood up twice when the girl was a no show at the meeting place and at least twice more when the girl made a date but failed to make the last confirmation but I didn't have to go to the meeting place. Of the girls I've met, I've fucked 4, two of them more than once, and I've walked away from 2 (one too heavy though with a pretty cootch, see the previous pix, and another too restrictive, she's the one who now wants to meet again) and one wouldn't meet me alone after a get acquainted session.

I've got two now who say they want to meet and I need to figure out how and when. One should be a sure fuck if I want it since she's already had my dick in her mouth but I walked out when she got restrictive about access to her pussy. She's mid-twenties and a single mother. The other is an artsy student type in early thirties, she says.

Of the 4, two are mid-thirties and two are late twenties. Two of them are single mothers. Girls over 23 commonly misstate their ages on the site. So do I. I look younger than way past 60 which is what I am. A lot of girls say they are looking for 30 to 75 or 18 to 90, but many others state they are looking for guys no older than 45 or 50. Several girls agreed to see me even though my stated age didn't meet their stated age requirement. I don't bother with a girl who wants someone close to her own age, because they aren't looking for a sugardaddy or a customer, they're looking for a husband. Two girls who state they are 19 but looking for older men acted like teenagers by making dates with me and then failing to confirm at the last minute, so they probably are teenagers. Anyway that's what I think.

I second the thanks for the info about your methods. Part of my problem is I choose not to use the city where I live but use Richmond since I get a pass from the warden to go there two to three times a month on business. This restricts the amount of time I can spend in pursuit so I'm looking for a home-run right off the bat. I'm debating if it would be a better use of time to focus on escorts with good reviews. The allure of SB was to hook up with amatures but they sure take a time investment. I'm going to give it another month or so. Keep us posted on how your search is going and I will do the same.

Coolhand

[Literal2]

One of the sb's was into unsafe sex before I could stop it. I checked out http://www.tstd.org/ And got anonymous std screening for about $$.5.

[Literal2]

It's possible to find near-perfection in an sb, sometimes for some of us anyway. I met SB4 for the second time yesterday. If anything it was even better than the first time. This woman is gorgeous inmo. Perfect figure, lovely face, lovely long thick dark hair, white teeth, plus she's smart as hell. A butt to die for. Pussy so clean you could eat all your meals off it. She's had a boob job which took her up to double D's. I'd prefer she had stayed natural and she didn't want to get that big but right now they are very pretty to look at. Like some body art and piercings that she has, she will regret these things with time, but for now they just make her look exotic and they are well done and I love them! She's very affectionate, calling me sweet names in our emails, very sexual and cums easily, but I can tell from her vagina wetness factor and failure to ask for my dick in her mouth that she is putting up with me rather than going nuts over me (like the squirter I talked about did). She's late twenties. She's had a couple of long term sugardaddy relationships with guys about my age in the past and I'm not sure how long I can hold on to her but I have limits in terms of what I will spend and how often. So far her allowance needs have been reasonable but I took some risk seeing her yesterday. I have to drive for hours to get to her. On the way back I had a goddam flat tire! I was out in the boonies at night with a rented car and curfew looming back at the prison. I am cursing and sweating and trying to change the friggin tire with a local beer drinking dude asking nosy questions and one eye on the time. It took me about 30 minutes, which was my cushion. I made it back to my cell with about two minutes to spare before the warden would have gotten suspicious. Whew.

[Literal2]

There are a few different SB sites out there. The two biggest seem to be SeekingArrangement and SugarDaddyForMe. The former has more women, but I've had better success on the latter. Which are you guys using?

For what it's worth, my best success used to be posting on the women-seeking-men section of Craigslist. But now that they're policing the posts much more thoroughly, it's become alot more difficult to make a post that gets across what you're really looking for without getting deleted, and posting on the casual-encounters section is a complete waste of time.

Thanks for the info about your methods. I love usasg. I learn something new about how to search for pussy every day. The site I'm using is the second site you refer to.

[Literal2]

I have been on SB site since mid-December last year. I have had one success which I have seen every couple of weeks since beginning of the year. I have been searching for something fresh but have not come up with anything. Question for you is; how old are the women you've been seeing and what is the age limit their looking for? Thanks in advance for your help.

Coolhand

Let me think. I started with the site in November. I search for 18-45 and recently began restricting by body type. I have probably contacted 60 to 70 girls by this point and received replies from 20 or so. I've seen 7 and been stood up twice when the girl was a no show at the meeting place and at least twice more when the girl made a date but failed to make the last confirmation but I didn't have to go to the meeting place. Of the girls I've met, I've fucked 4, two of them more than once, and I've walked away from 2 (one too heavy though with a pretty cootch, see the previous pix, and another too restrictive, she's the one who now wants to meet again) and one wouldn't meet me alone after a get acquainted session.

I've got two now who say they want to meet and I need to figure out how and when. One should be a sure fuck if I want it since she's already had my dick in her mouth but I walked out when she got restrictive about access to her pussy. She's mid-twenties and a single mother. The other is an artsy student type in early thirties, she says.

Of the 4, two are mid-thirties and two are late twenties. Two of them are single mothers. Girls over 23 commonly misstate their ages on the site. So do I. I look younger than way past 60 which is what I am. A lot of girls say they are looking for 30 to 75 or 18 to 90, but many others state they are looking for guys no older than 45 or 50. Several girls agreed to see me even though my stated age didn't meet their stated age requirement. I don't bother with a girl who wants someone close to her own age, because they aren't looking for a sugardaddy or a customer, they're looking for a husband. Two girls who state they are 19 but looking for older men acted like teenagers by making dates with me and then failing to confirm at the last minute, so they probably are teenagers. Anyway that's what I think.

[Coolhand2]

There are a few different SB sites out there. The two biggest seem to be SeekingArrangement and SugarDaddyForMe. The former has more women, but I've had better success on the latter. Which are you guys using?

I'm using SugarDaddy.

[CantWinLosin]

There are a few different SB sites out there. The two biggest seem to be SeekingArrangement and SugarDaddyForMe. The former has more women, but I've had better success on the latter. Which are you guys using?

For what it's worth, my best success used to be posting on the women-seeking-men section of Craigslist. But now that they're policing the posts much more thoroughly, it's become alot more difficult to make a post that gets across what you're really looking for without getting deleted, and posting on the casual-encounters section is a complete waste of time.

[Coolhand2]

I think the sb website has three types of girls. 1. Real amateurs who want some money but would never think of themselves as escorts. 2. Girls who are escorts or part time escorts. 3. Girls too unattractive to be escorts. I don't partake of the SW scene so I don't know how they compare. I assume the SW's are also at the low end of the looks department, but I don't really know.

I have been on SB site since mid-December last year. I have had one success which I have seen every couple of weeks since beginning of the year. I have been searching for something fresh but have not come up with anything. Question for you is; how old are the women you've been seeing and what is the age limit their looking for? Thanks in advance for your help.

Coolhand