"Sugarbabies" / "Arrangements" Amateurs or Not?

**Literal2** · 03-10-11 16:32

I've been emailing SB9 for more than a month, first through the sb website and then by our own emails. One meeting was put off because of her period. When I first asked her to meet me in a hotel she said,"I don't even know you!" So we set up a get acquainted meeting to which she was so late I could only spend five minutes with her. She was sorry and said she'd be on time next time, so I set another date for a hotel. This time she said,"I've never done this before but its the only place we can meet I guess." She says she's 27 and looks like it, nice body from what I could see, very cheerful, pretty. I've been waiting to fuck her for a long while and I think it's finally going to happen Saturday. She is definitely a non-pro. She could be a keeper if I can manage the relationship correctly. I've told her it will be a couple times a month and has to be discreet and she's ok with that. Meanwhile on Sunday I have a three-peat scheduled with SB4. That girl is so hot but she is also so hard for me to get to. Plus now she wants more money. I'll have to see how things go Sunday. This may be my last time with SB4. But I want to have a harem of hot 20-something girls to fuck when I feel like it and I can't do it if I don't hold on to the ones I like the best.

**Coolhand2** · 03-09-11 01:10

Originally Posted by Literal2 [View Original Post]

Sounds like a good time, Cool. Congratulations. I've never had a non-pro get a hotel room. Very unusual, especially for a first date. Who paid for the room and if she did, did you increase the amount of her gift? Just curious.

I find different girls have different sexual skills too. Sometimes oral skills are lacking in the hottest girls. Maybe they just feel they don't have to work so hard because they're cute. On the other hand, some girls just seem obsessed with getting their mouth on your dick. It would be great to find some way to predict this, just like it would be great to be able to predict what a girl's pussy looks like from her external appearance. What I like is a pussy that starts out neat and tidy and then gets messed up as you go along.

Are you planning to loop back and do csb1 again? Or will she be backup while you go for the next two potentials?

As for me, I haven't worked the sd website (contacts and emails to new girls) at all for about two weeks. I have my atf sb4 coming up again this weekend, and supposedly sb9 who I met with briefly in a bar over a week ago. SB9 is a student / artist and very curvy and flirty and has been out of town for a week on vacation. Before she left she said she was eager to move on to penetration but we shall see. It would be my luck for her to run into some dudes on vacation who have been fucking her brains out to her total satisfaction. I hope not. She has the potential to become another fave and it would be just great to have her as well as sb4 whenever I want. Meanwhile other possibles keep replying to my sd website emails from weeks ago and one or more of these may develop into something, especially if sb9 doesn't come through for me.

Her getting the hotel room was the reason I placed her in the amateur / semi-pro category. I wasn't quite sure what to make of it. She did pay for the room so being the gentleman that I am, I did increase the amount of her gift. In retrospect that could be a problem since she doesn't know that's what I did and made create an expectation that I won't meet. I haven't decided yet if there will be another meeting with her (CSB2) so it may not matter. It may depend on how things go with the two new potentials I mentioned. There's still the five that say they are ready to meet so I have to decide something there.

If you're able to figure out a way to predict what a girls sexual skill sets are sign me up quick. That's why I would not see a provider who did not have reviews that gave me some idea of what I was paying for. With the Sugar Babies it's a total crap shoot. I may have been spoiled by the great skills that CSB1 has. Which is why, in answer to your question, I'm trying to set up a meeting with her next week. I figure why I try to sort out what I'm going to do about the other SB's I shouldn't let such talent go to waste. (Men are such dogs!)

Good luck with SB9. Even if there were some dudes fucking her brains out, vacation is over and it's time to come back to reality. I bet that what ever her financial issues were that brought her to the SD site in the first place are still there and still need to be addressed. Besides, a sore pussy will get better, unpaid bills won't!

**Literal2** · 03-08-11 12:54

Sounds like a good time, Cool. Congratulations. I've never had a non-pro get a hotel room. Very unusual, especially for a first date. Who paid for the room and if she did, did you increase the amount of her gift? Just curious.

I find different girls have different sexual skills too. Sometimes oral skills are lacking in the hottest girls. Maybe they just feel they don't have to work so hard because they're cute. On the other hand, some girls just seem obsessed with getting their mouth on your dick. It would be great to find some way to predict this, just like it would be great to be able to predict what a girl's pussy looks like from her external appearance. What I like is a pussy that starts out neat and tidy and then gets messed up as you go along.

Are you planning to loop back and do csb1 again? Or will she be backup while you go for the next two potentials?

As for me, I haven't worked the sd website (contacts and emails to new girls) at all for about two weeks. I have my atf sb4 coming up again this weekend, and supposedly sb9 who I met with briefly in a bar over a week ago. SB9 is a student / artist and very curvy and flirty and has been out of town for a week on vacation. Before she left she said she was eager to move on to penetration but we shall see. It would be my luck for her to run into some dudes on vacation who have been fucking her brains out to her total satisfaction. I hope not. She has the potential to become another fave and it would be just great to have her as well as sb4 whenever I want. Meanwhile other possibles keep replying to my sd website emails from weeks ago and one or more of these may develop into something, especially if sb9 doesn't come through for me.

**Coolhand2** · 03-07-11 23:54

Had my meeting today with CSB2. First of all she wanted me to arrange a meeting place but I told her since she knew the town better that I would leave that up to her. I wanted to see where she would pick since I thought it would give me some indication on where her head was. I called her when my business was finished and she texted me an address as to where to meet her. It was only when I got there that I found out it was a motel with a bar. I thought this was good sign. Met her in the bar and had a drink. She was in her early thirties, kind of cute with a decent rack. She seem determined to have the "first date" kind of conversation that I really wasn't into. Not having tons of time (the warden keeps a good eye on the clock) I pressed to move things along. The "allowance" issue did not come up at all. As it turned out she had already got a room (an even better sign) so we proceeded on up. Didn't take long to get her out of her clothes and as it turned out her body was nicer then CSB1. We then spent a nice couple of hours between the sheets. She was attentive, passionate and very willing. She got wet easily and came several times with out to much effort. (At my age that's important) Here's the thing; even with all her effort and willingness, she did not have the skills of my CSB1 housewife! CSB1 really knows what to do with a dick in her mouth and provides a trip to the islands. Just because of what she did with the hotel room I'm placing her between the amateur and the semi-pro category. I put the allowance in her purse as I was leaving so I don't know her reaction yet. I'm currently in communication with two more potentials, both single moms. Another home run makes it a good day.

**Coolhand2** · 03-06-11 02:00

Originally Posted by Literal2 [View Original Post]

I hope Cool lets us know what happens Monday, one way or the other.

For sure. Still havn't heard from CSB2 since my answer on the allowance.

**Literal2** · 03-05-11 11:39

I think the arrangements site asks "How much allowance are you willing to pay per month?" or something like that, which makes the relationship sound more long term. One of the earlier comments here (Thud maybe) said he tells them $1k per month based on multiple visits.

In my case I don't usually have any amount agreed to but I do hope that if we like each other it won't just be a one time thing. I try to leave them happy both by a gift and sexually so I don't have a problem telling them in advance I don't want to talk specifics but I expect they will be happy. I've cut off several possibilities after progressing to the date setting discussion because the girl became too demanding. I want the initial meet to be highly anticipated and exciting for both of us. When distrust creeps in at this early stage of a relationship it can turn everything sour.

As we've said I don't think chasing sb's or amateurs is for everybody. When you want a sure thing you sometimes really have to get it or you will feel ill and unable to think of anything else. But for me, chasing sb's is a lot like hunting or fishing. Sure you can go into the grocery store and buy whatever you want to eat off the shelf. But it just doesn't taste as good as something you've stalked for hours and landed all by yourself.

There are always more females out there if one doesn't come through.

I hope Cool lets us know what happens Monday, one way or the other.

**Literal2** · 03-05-11 07:29

I think they use allowance because it seems different from what prostitutes or escorts get. The seeking arrangements site (to which I don't belong) has a question for the sugardad's profile: "How much allowance can you pay?" or something like that. Their idea I think is that the relationship is not a one time meeting in which sex is exchanged for cash. I try to avoid discussing cash in advance but reassure the girl that I think she'll be happy. I had one experience (SB3 I think) who strung me along for weeks and to whom I gave several small sums of money as gifts. But she would never be alone with me. A couple of times, I've given a girl some sugar and then walked out without completion for various reasons. But now I always wait until I'm alone with the girl before I give her anything. Well, maybe I'll buy her a drink. And I wait until the end of our date. Good luck guys.

**Coolhand2** · 03-05-11 03:26

Originally Posted by Cantwinlosin [View Original Post]

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.

I consider the term allowance a euphemism to disguise the financial arrangement for what it is: pay to play. Key word there is play. Unlike an escort where upfront payment is expected I would not be so inclined in the SB / SD relationship. As I said with my one success (CSB1) I leave the amount as I leave. I intend to follow the same practice on Monday. Worst case is I've wasted one of my passes from the Warden (which would piss me off) but no financial lost. I haven't heard from CSB2 since my ambiguous response to her inquiry about would she be happy with her allowance. We'll see what happens. I've got CSB1 on standby just in case.

Coolhand

**CantWinLosin** · 03-05-11 00:07

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** · 03-04-11 17:54

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** · 03-01-11 12:53

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** · 02-28-11 14:20

Originally Posted by Literal2 [View Original Post]

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** · 02-28-11 13:27

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** · 02-28-11 02:32

Originally Posted by Literal2 [View Original Post]

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** · 02-27-11 06:16

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.