"Sugarbabies" / "Arrangements" Amateurs or Not?

**Dr.Monger** · 05-18-11 00:56

Gentlemen,

What a great thread. I have gone back and read almost all the posts, and it has certainly been fun to read. I myself have dabbled in the SB world, but mostly without success. A few years ago I nailed a few girls based on ads placed on CL. In fact. I was 3 for three in nailing women I actually met. Two were one offs (although I would have seen one of the two again. She opted out) , and the third was an absolutely gorgeous girl who I thought was actually developing into a real relationship, but in the end boiled down to the cash (duh) not being enough, despite specific amounts never having been discussed. But she was smoking hot, and oh so worth it. It was a number of years ago, but I think she did three overnights, including one spectacular morning fuck that still lives in my memory because we woke up spooning, I penetrated her from behind after getting her wet, and slow fucked for about a half hour until I could not take it anymore, rolled on top and pounded into her until I popped. Just amazing. Found a picture of us the other day and it made me smile. Sadly, CL users tend to flag SD posts, even in casual encounters. Just a bunch of haters on there now.

More recently, I have been using an internet site, but with little to no success. I do not have a picture up, and invariably the first thing they do is ask for a picture. The communication then ceases, or they say "you're cute but not my type". And I am writing to almost every woman in my area, although admittedly the particular site on which I am active does seem to be very limited in terms of the number of women near me who fit my preferences. I have expanded my search to within a 5 hour drive, but the results have been about the same. A couple have emailed back and forth repeatedly, but after a while it became clear they were never going to meet me. Also, it appears that girls in DC which is nearby seem to think their cootch is worth more than ordinary women.

I have looked at SeekingA and SD4Me which seem to have more prospects, but I am concerned about the same kind of non-responses I am currently getting, and to be blunt, throwing good money after bad. I am not outrageously ugly, in fact one fairly hot SB from a free SB site is relentlessly pursuing me for a real relationship, but her baggage is to much for me to accept. And the local girls seem to be looking for young guys (which I find odd). Many post "no one over 40" etc. How many under 40's guys are looking for, or can afford a SB? I think a lot of these girls are dreamers.

I did wind up nailing one very hot chick from the site I am active on, but that did not work out well, and although she was hot, she was a smoker, and always had bad breath, plus again tons of issues (which seems to be a recurring theme with these ladies). But like I said, most of the others I met have been duds, and even getting a response after sending a pic is challenging.

Would it be fair to say SA and SD4Me have more, shall we say,"motivated" ladies? Any suggestions as to a good site would be appreciated.

As a side note, I noticed a lady on SA who is actually a FB friend of mine! I don't know her in person, but we have many mutual friends. I am sure she want way more than I am willing to part with, since she is a part time "model". I also had extended contact with a SB from a different site who it turns out is a porn star. She never told me, but some detective work revealed who she was. Sadly, she was in the "you're cute but not my type category".

Lastly, while on the subject of Facebook, has anyone else noticed the complete and utter lack of identity security that most of these ladies seem to have? Many use their regular email accounts with their names attached. And others use accounts linked to their Facebook pages. If you do not have a FB account, you are usually prohibited from seeing profiles, but if you make one, even if in visible, you can plug in e-mail addresses and find the person's profile, which usually has a full name and sometimes photos. And sometimes it can reveal if the lady in question is in a relationship, etc. Of course it is also how I discovered that a girl I was dating was cheating on me. So it's very useful. Even a first name and a city can work to find these girls. Many use their profile photos from FB on their SD pages.

Dr. Monger.

P. S. Has anyone here paid by money order, etc. To avoid a credit card charge? Also, SD4Me claims a 3 day free trial, but you need to give a credit card. It that legit?

**Coolhand2** · 05-17-11 22:53

Originally Posted by Spitfire [View Original Post]

Good luck with her! Any chance you could stay another day or two to pick up the others as well?

I wish. The Warden does not issue overnight passes. I only get 2-4 day-trips a month, with a 2-3 hour window to get into mischief. It adds a degree of difficulty when dealing with SB's.

**Coolhand2** · 05-17-11 22:41

Originally Posted by Literal2 [View Original Post]

Thanks for your reports, which I enjoy because I usually learn something.

Au contraire, it is I who has learned from the Master.

**Spitfire** · 05-17-11 17:29

Originally Posted by Literal2 [View Original Post]

I couldn't believe the sb who showed up at my door: just like her photos, a real college student, slim, fresh, smart. The firmest little body. The pinkest little giner. She did everything I wanted. She's way up there on my list of atfs. I had no idea I could fuck such quality pussy at this stage of my life. I'm going to savor this one for a while. Damn.

Sounds like you found a winner! Careful or you'll end up like me. Only wanting 1 good one.

**Spitfire** · 05-17-11 17:28

Originally Posted by Coolhand2 [View Original Post]

I think I'm going to go with CSB6. I talked to her today and she still seems full of gratitude. She said that now that she knows she can trust me she can let down her guard and just enjoy our time together.

Good luck with her! Any chance you could stay another day or two to pick up the others as well?

**Literal2** · 05-17-11 17:26

Originally Posted by Coolhand2 [View Original Post]

I think I'm going to go with CSB6. I talked to her today and she still seems full of gratitude. She said that now that she knows she can trust me she can let down her guard and just enjoy our time together. I'm just afraid that time will allow that feeling to dissipate. If I don't see her Thursday (two days from now) my next opportunity is at least a week away. Besides, I can't get the vision of that body out of my mind. I'm hoping I can get at least one of the two that I had scheduled for Thursday to hang in there til next week. I had put in a lot of time and effort (gentler effort) getting them to the point of meeting with an expectation of giving up the pussy. I sure would hate to see that effort go to waste. I just don't have the freedom of movement (or skill) that Lit seems to have to line SB's up for a landing (pounding) like an air traffic controller at Dulles.

Good luck Cool. Something that's changed for me in my approach and works for me is to focus on getting the girl alone, rather than all the other details. I didn't say anything about sugar at all to sb18. It was all implied. I just focused on getting her into the fucking chamber alone. With the "cool" style, you have to be laid back about it and willing to walk away. It helps having a few babes lined up as alternatives as you seem to be doing. Thanks for your reports, which I enjoy because I usually learn something.

**Coolhand2** · 05-17-11 16:58

Originally Posted by Varoom [View Original Post]

Wow CH2, you must have mellowed in your SD old age; fronting gals sugar with no guarantee of penetration. This doesn't usually work but maybe you have found the one in 10, 000 that will actually deliver. I for one have had NO luck with advancing sugar even with gals that there has been a long standing track record of seeing them. Once they seem to be ahead of the game on you there is rarely ever a catch up provision issued. Hoping your situation with this SB is different. I guess a little bit of sugar isn't going to break you if it doesn't pan out. Good luck on it.

I agree with you that as a matter of principal, it's a bad idea. It was the amount that was key. The old Coolhand would have stood on principal regardless of the amount. The new mellowed Coolhand decided that I would have spent more on a hotel room so take a chance. I can't declare victory yet because my johnson is still dry, but the indicators point to a dive into the deep end of the pool. I'll know in a few days.

**Coolhand2** · 05-17-11 16:45

Originally Posted by Literal2 [View Original Post]

Let us know how you sort this out. It's a nice problem to have if you like pussy.

I think I'm going to go with CSB6. I talked to her today and she still seems full of gratitude. She said that now that she knows she can trust me she can let down her guard and just enjoy our time together. I'm just afraid that time will allow that feeling to dissipate. If I don't see her Thursday (two days from now) my next opportunity is at least a week away. Besides, I can't get the vision of that body out of my mind. I'm hoping I can get at least one of the two that I had scheduled for Thursday to hang in there til next week. I had put in a lot of time and effort (gentler effort) getting them to the point of meeting with an expectation of giving up the pussy. I sure would hate to see that effort go to waste. I just don't have the freedom of movement (or skill) that Lit seems to have to line SB's up for a landing (pounding) like an air traffic controller at Dulles.

**Literal2** · 05-17-11 16:36

I couldn't believe the sb who showed up at my door: just like her photos, a real college student, slim, fresh, smart. The firmest little body. The pinkest little giner. She did everything I wanted. She's way up there on my list of atfs. I had no idea I could fuck such quality pussy at this stage of my life. I'm going to savor this one for a while. Damn.

**Literal2** · 05-17-11 16:30

Originally Posted by Literal2 [View Original Post]

SMs pm me for contact info of Va Beach sbs I'm thru with.

I've given contact info for one sb to an active contributor to this forum. I'll give out another in a few days.

**Varoom** · 05-17-11 11:46

Originally Posted by Coolhand2 [View Original Post]

The old Coolhand would not have considered such a thing. (No pussy, no sugar) The new kindlier gentler Coolhand figured that a small amount of sugar might reap future benefits. But remember I had never actually seen her. I told her I would give her what she needed and we agreed to meet this afternoon.

When I got home there was a message that said that she now knew she could trust me and she wanted to make me happy. She said that if I come Thursday to just get a room because she was going to make sure that I would "fall head over heels.

The moral of this story is that there maybe something to this kindlier, gentler shit.

(edit delete)

Wow CH2, you must have mellowed in your SD old age; fronting gals sugar with no guarantee of penetration. This doesn't usually work but maybe you have found the one in 10, 000 that will actually deliver. I for one have had NO luck with advancing sugar even with gals that there has been a long standing track record of seeing them. Once they seem to be ahead of the game on you there is rarely ever a catch up provision issued. Hoping your situation with this SB is different. I guess a little bit of sugar isn't going to break you if it doesn't pan out. Good luck on it.

**Literal2** · 05-17-11 06:53

Originally Posted by Coolhand2 [View Original Post]

CSB6, is a 5'7, 23 year old Hispanic SB that I had been communicating with a few months back. She had emailed me some pics and was very nice to look at. We were on the verge of meeting and sealing the deal when she got a job and kicked me to the curb. I noticed last week she was back on the site so I messaged her. She responded how glad she was to hear from me. To make a long story short she had lost her job and was on the verge of losing her car and would do anything I wanted if I would help her out. The amount she needed was less than a $ and after more back and forth I felt she was sincere. It so happened that I was going to be in her area today but no time for an extended visit. The old Coolhand would not have considered such a thing. (No pussy, no sugar) The new kindlier gentler Coolhand figured that a small amount of sugar might reap future benefits. But remember I had never actually seen her. I told her I would give her what she needed and we agreed to meet this afternoon.

She should destroy what ever camera took the pictures she sent because to say she looked better than the pictures is the understatement of the year. She was stunning. Tall, built like the proverbial brick house, with long black curly hair that went down her back. I gave her the sugar and said I might be able to get back for a few hours on Thursday. She told me that she would like that very much and no additional sugar would be necessary. When I got home there was a message that said that she now knew she could trust me and she wanted to make me happy. She said that if I come Thursday to just get a room because she was going to make sure that I would "fall head over heels." The thing is I had already lined up two SBs for Thursday that I was going to have to decide between. A 22 and a 34 year old who are basically 5'3/5'4 carbon copies of each other. The 22 year old just sent me a message about how much fun we're going to have. To top that off, I got a message yesterday from a 28 year old that now wants to meet.

The moral of this story is that there maybe something to this kindlier, gentler shit.

Ha ha.

Let us know how you sort this out. It's a nice problem to have if you like pussy.

**Coolhand2** · 05-17-11 02:30

CSB6, is a 5'7, 23 year old Hispanic SB that I had been communicating with a few months back. She had emailed me some pics and was very nice to look at. We were on the verge of meeting and sealing the deal when she got a job and kicked me to the curb. I noticed last week she was back on the site so I messaged her. She responded how glad she was to hear from me. To make a long story short she had lost her job and was on the verge of losing her car and would do anything I wanted if I would help her out. The amount she needed was less than a $ and after more back and forth I felt she was sincere. It so happened that I was going to be in her area today but no time for an extended visit. The old Coolhand would not have considered such a thing. (No pussy, no sugar) The new kindlier gentler Coolhand figured that a small amount of sugar might reap future benefits. But remember I had never actually seen her. I told her I would give her what she needed and we agreed to meet this afternoon.

She should destroy what ever camera took the pictures she sent because to say she looked better than the pictures is the understatement of the year. She was stunning. Tall, built like the proverbial brick house, with long black curly hair that went down her back. I gave her the sugar and said I might be able to get back for a few hours on Thursday. She told me that she would like that very much and no additional sugar would be necessary. When I got home there was a message that said that she now knew she could trust me and she wanted to make me happy. She said that if I come Thursday to just get a room because she was going to make sure that I would "fall head over heels." The thing is I had already lined up two SBs for Thursday that I was going to have to decide between. A 22 and a 34 year old who are basically 5'3/5'4 carbon copies of each other. The 22 year old just sent me a message about how much fun we're going to have. To top that off, I got a message yesterday from a 28 year old that now wants to meet.

The moral of this story is that there maybe something to this kindlier, gentler shit.

**Literal2** · 05-16-11 18:58

SMs pm me for contact info of Va Beach sbs I'm thru with.

**Literal2** · 05-15-11 21:46

After many months waiting, today Mr Johnson finally had his way with sb3. She's put on weight since the pix, but she is another squirter. Satisfying but too demanding sexually.

SB17 and I had lunch, she's older than her pix. Nice woman and now she is clearly ready to be fucked. Unfortunately for her, I'm no longer interested. She should have agreed to meeting at the hotel where she could have appealed directly to Mr Johnson.

SB18 confirmed by cell today she will come to my hotel in short pump tomorrow. Can she really be so easy with her gorgeous 23 year old body and cute face. She says she is a college student. We will see. I still don't believe it. It would be great if she does though.