"Sugarbabies" / "Arrangements" Amateurs or Not?

**Castlerae** · 05-09-12 22:21

Everyone's updating their status, listing their newest conquests (or potential ones) , so I thought I'd bring in my own experiences. After multiple casts with no nibbles, one took the hook in her mouth enough to reply. After a few back-and-forth messages, she asked me what I wanted in a relationship. I was honest and told her I'd like to meet her, get to know her, find out how we 'got on', then move to a more physical relationship if things worked out. Now she's talking about not wanting a 'serious' relationship, so I'm guessing sex isn't in her plans. Might see her anyway, as her pic is pretty decent looking (and in hopes of changing her mind, of course!). About the same time, I got an approach from a woman living nearby. Not sure she's my cup of tea, as her self-description says "average", but the weight she gives and the size of certain other parts of her anatomy make me think she's going to be another "BBW". Guess I can set up a short meet of some sort to find out.

So that's the story from the sugar gulag. Enjoy your good fortunes, my fellow fishermen.

**BigTigger** · 05-09-12 20:49

I see Alias has stumbled upon the FFG phenomenon. It's always good to have one on speed dial. .

Originally Posted by AliasSM [View Original Post]

I met last week with one of my BBWs from a few months ago. She has stayed in touch and seems to really appreciate the sex, more so than most SBs in this game. Sure she appreciates the money also, but the sexual gratification is extremely high for her. I like that! She is not my body type and would not consider seeing her again if not for the fact that she is genuinely good in bed and totally into the act when we are together.

**BigTigger** · 05-09-12 20:47

Greetings All.

I'm not exactly back, but I wasn't exactly gone. I've been trying to keep up with the forum and it's great to see the board so active. I've bounced around between a few SBs who've been keeping me busy. Had a couple that took up more time than others but those have all moved on for one reason or another. Now I'm back to spreading my suga around until I settle on 1 or 2 consistent favs. Right now locally, one Korean. 3 African Americans, one Caucasian with Red Hair-blue eyes and bountiful booty, still have the NJ SB (seeing once a month). Oh and I replaced my anytime bootycall FFG (Freaky Fat Girl) with another FFG (both are Caucasian) , this one has her own place and fewer mental issues. LOL.

As you can see, I am still working in my niche area (SBs who are ok with most of the funds being spent on activities together as opposed to allowance). All in all, the market is still great. I'm hoping soon I can join the party here again participating and being more informative. But keep up the good work, I'm enjoying the read. And last but not least, welcome Mandy!

Thanks for asking about me Scott, I appreciate that. I startled me back into the reality of being a contributing member as opposed to a voyeuristic freeloader.

BigTigg

**F Scott** · 05-09-12 18:30

Originally Posted by Hernando [View Original Post]

I have never had bad sex with anyone, some are just better than others.

Nando,

Yet again, you strike to the heart of the matter. Sometimes I wish I weren't Irish, and so could be a little more pithy. I also agree with your statement that entering into any new relationship is a combination of anticipation and anxiety. We just don't know how things will turn out until they turn out. Hope for the best, and give the baby a chance, or maybe two. What did Joe say a while back, something about it being just like real life, only we both know it's pure fantasy? To me, that encapsulates the reality that it is both ours and the baby's responsibility to preserve and contribute to the relationship / illusion. My ATF calls our time together "vacations". I like that.

Scott

**Hernando** · 05-09-12 17:46

Drummer, you bring up a topic near and dear to my heart.

I have never had bad sex with anyone, some experiences are just better than others.

So, a new relationship is full of anticipation but also anxiety. I anticipate a great time but am not turned off by anything except utter disconnection. For a SB who is courting you as a pot SD, she should put some energy and emotion into it as should you. So I would give the relationship time to grow and for feelings to develop. There is a point at which you might just not feel any connection and call it a day even though you are getting laid. To me a SB is a long term committment and I approach selecting her as I would an IRL GF.

I would trade E connection for experience and skill any time. Also extreme sexual skill and comfort with sex suggest a high degree of experience and I am personally more interested in a partner I can mold as a SB rather than a pro who has been around the block many times.

**F Scott** · 05-09-12 17:07

Originally Posted by Atldrummer [View Original Post]

After thinking looking at my last post I started thinking about sex and the SB / SD relationship. So, here's a few questions for the group:

Do you expect the sex to be fantastic the first time with your SB?

Do you judge the future of the relationship on the quality of the first-time sex experience?

Do you have patience to let it grow with time?

Interested to hear your opinions,

Drummer

Drummer,

Sounds like you are having fun in the Bowl. I was interested to read about one of your babies that you just hang out with, no sex. I am thinking I might suggest that to my Irish Cherokee. I think I would enjoy her company, and she certainly is easy to look at. My question to you: do you have in the back (or further forward) of your mind that things might / should progress towards a more physical relationship? In other words, is that the long-term goal here, or are you really content with things as they are?

Now, on to your questions:

Yes, I do expect the sex to be fabulous the first time, but I do put some effort into things, and try to make it as fantastic for her as well. With one or two exceptions, it has in fact been pretty darn excellent. Would I stop seeing someone if it were less than great? It depends. If I felt there was the possibility of something more substantial growing between us intellectually or emotionally, I would definitely give it some time. You have to think that the babies can be nervous or off their games from time to time just like us.

A case in point is my naughty Brit. The first time with her was awkward to say the least. She was shy, and a little too reserved in my opinion, so I began to feel unsure as well, and instead of passion, it was more like duty. Top that off with one of her cats coming in to the bedroom and scratching me on the ass and you get a picture of a small train wreck, which would not be inaccurate. It actually was pretty funny in hindsight, but still. Our next meeting was just for breakfast, where we had a fantastic time talking and laughing, and the rest, as they say, is history.

Having said this, I don't know if I would have pursued anything further if we had not had that nice breakfast. What made me agree to that I can't really say. A hunch maybe, or just an addiction to her accent. Probably the latter. If our next time in the chamber had paralleled the first, however, that would have been the end. Fortunately for me, this was when the classic "fuck me harder, I'm your sl*t" was coined. Good Lord!

Keep up the good work, you all!

Scott

**TravelinSD** · 05-09-12 10:46

After thinking looking at my last post I started thinking about sex and the SB / SD relationship. So, here's a few questions for the group:

Do you expect the sex to be fantastic the first time with your SB?

Do you judge the future of the relationship on the quality of the first-time sex experience?

Do you have patience to let it grow with time?

Interested to hear your opinions,

Drummer

**TravelinSD** · 05-09-12 10:40

Hi Everyone, I've been traveling for business the last couple of weeks so haven't had time to look in here. I figured I'd give a quick update and put my 2 cents in on some of the threads.

To Mandy's NSA Impossible thread, I totally agree. Harking back to the features of an SB relationship having a social / emotional component and longevity, you can't have that type of relationship without strings becoming attached. If it's just sex for money what you really have is an escort.

Related topic of monogamy in the SB relationship. I don't think it should be expected. Especially if you're playing the the 18-25 or so arena. It's just not fair to expect that from a HYCB type gal. If it happens at the SB request, great, but I'd be realistic and not expect that to last. Experience has taught me that. And also that it is hard to keep jealousy out of the equation. It's something that I know was part of my last SB relationship demise and that I need to keep working on. I look at Mandy as my mentor and goal in this journey.

On sharing, since my divorce, I've pretty much been an open book on M&Gs. Even before that I was pretty open with my former SB from the get-go, mostly because she was open with me. You can't have a long-term relationship without getting into the details of the other person's life. That's what forms the connection. Even in my escort days I found a lot of openness in both directions on many occasions.

As far as my recent SB experiences they are definitely getting interesting and also a bit confusing. Here's the recap:

Spent a great evening a couple of Saturdays ago with a 23 yo cutie. Couple episodes of Homeland at my place then some nice playtime. This was our 2nd meeting. The playtime was pretty good, but still not spectacular. It may get better with time. She is a little flaky, frustrating for me, but I've found it just comes with the 20-something territory.

I have developed another relationship with one of my former escort contacts. She's no longer "working". The social contact is good, she's a super sweet person and we have a pretty good friendship going. She also happens to be the hottest, most beautiful woman I've personally had contact with. I mean a 10! The sugar comes in the form of a variety of situations she finds herself in and needs assistance. So far the assistance / sex ratio is pretty much in line. The only problem is the sex is really mediocre at best. Beautiful to look at, the sex is at times fairly hot, but kind of distant. Not sure what to do with this one.

I do have one other relationship that's about three months running. Nice girl and fun to go out with. No sex, but also no expectation or mention of an allowance or money. Of course I pay for dinner, drinks, entertainment, etc. It's turned into a great friendship and company, so I'm currently comfortable with it.

Another couple of M&Gs, but nothing of interest coming out of them so far.

Anyway, as most on this board, I'm having fun looking, but still would like to find "the special one (or two)"

Congrats to those that have found Nirvana, and good luck to those who are still looking,

Drummer

**AliasSM** · 05-09-12 05:31

Hello to all of my SD family. I just don't feel right calling you all brothers since Mandy has joined the family. Had a little time this morning so decided to share whats happening with this SD.

STill looking for that perfect match, but the search has definitely been fun lately. I have a third date with my AA coed this week and we plan to have a nice afternoon together before I leave town on business. She is OK in the FC but falls short of the GFE expectations that we all have in this exciting hobby. Still, she is 22, pretty as a picture, nice as can be, and I can't keep my mind off of her beautiful ass and young body. She will stay in the lineup until I find that LTR that can stop my little head from thinking about her.

I met last week with one of my BBWs from a few months ago. She has stayed in touch and seems to really appreciate the sex, more so than most SBs in this game. Sure she appreciates the money also, but the sexual gratification is extremely high for her. I like that! She is not my body type and would not consider seeing her again if not for the fact that she is genuinely good in bed and totally into the act when we are together.

I had 2 lunch dates this week. One with a very pretty young nurse that has recently come off of another SD type arrangement. She has long term potential but I have not yet sampled the wares in the FC. She is very cute though and we have already discussed the next date. She knows what I'm looking for and seems good with everything I have suggested. Mid-twenties, highly educated, looking for that older man in her life to provide some excitement (who would have thought we would ever hear that). I swear, I don't understand the attraction for them, but she seems to be real and not JUST into the money part of the relationship.

The second lunch date is scheduled for today with a 30 yr old MILF. She sounds nice, divorced with a couple of kids, and it will be the oldest SB I have been with to date (I think anyway). I am looking forward to checking her out as it sounds like she has the potential to host at her house and I'm getting a little tired of the hotel bills. Hopefully, she is not a Nando type 1. I don't have the time or risk-tolerance for that.

All of that, and my work life is taking me to the west coast next week with some free time in Tijuana! Life could be real good over the next 10 days if even half of these opportunities end up in the FC.

I am really grateful for all of your posts. Couldn't have succeeded in this hobby without all of your input.

Alias

**VAJimbo** · 05-08-12 19:29

My SB has just moved so I'm back fishing and thought I would share what I have found in the 1st few days of the hunt.

Talked to a nice looking 24yo who was pushing for more than lunch, when I finally said yes we could do more (I hate to commit before meeting them) she let me know she expected $800, I told her sorry and she got ugly quick.

Next up 22yo model, a bit hoodish (Tats and booth nips pierced) but good skills and hot looking as could be. Only issue she wanted to put the party hat on 20 secs after we were in bed. I think I'll see her again later this week to take another test drive, she is not long term.

Just started talking to another 24 yo, will need to see if it goes anywhere she seems nice and is good looking so maybe.

It's fun to sample the young lovelies but, in the end I would rather have that one special girl.

**F Scott** · 05-08-12 19:01

My brothers (Mandy included) ,

I got back into town last night after a lovely long weekend of RandR, and was delighted to read all the posts on the various exploits, considered opinions, and helpful advice from you all. This has got to be the Greatest Thread In The World, right?

Joe, by now you are on the other side of your overnight, and I am certain it was all you hoped for and most probably more. If you are like I was after my first, you are sitting quietly somewhere, staring out the window with a silly grin on your face. Please share when you are able to make coherent sentences!

George, welcome to the Bowl. It sounds like you may have had a little experience under your belt already, but as we all can attest, you never stop learning or polishing your game. Nando and the rest have commented eloquently on the issue of sugar, monogamy, personal revelations etc, so I will refrain from adding my two cents with one exception, which is to second the cautionary statement about revealing anything to a Nando 1. There is just no upside in it. It will not engender trust, closer feelings, greater intimacy or anything like that. The only thing it does is expose you to potentially catastrophic trouble. Someone mentioned the difficulty in maintaining their alter-ego, and while I agree to a point, it is also paramount to understand the level of baby you are playing with. If you can't stay under deep cover, don't mess with the 1's.

As for me, I had a lovely morning talking with a trusted friend, and am hoping that continues to be a constant as our schedules allow.

Brit and I are arranging a play date for next week, when the Mater will be safely back in Texas.

Polo is back in the on-deck circle, though no firm arrangement has been made, the week being almost over and me not being an eccentric millionaire but in reality someone who has to work from time to time. She has promised to bring some of her favorite toys to our next get-together, so that is something to look forward to. She also tells me that the recent sunshine we have had has upped her freckle count somewhat, so a thorough examination is clearly in order.

As predicted, Cherokee princess has dived down her burrow again, and is refusing all my entreaties to come out and play. I am going to proceed here as if it were an impossibility, and just something that is amusing to pursue as time and inclination allows. If she comes to the net, all to the good. If not, I will not sweat it.

My ATF and I have plans to get together on Friday for lunch and, if all goes well, a little hide-and-seek at the new apartment. I did not want to burden you all with my insecurities, but I had really thought she was gone for good this time, but apparently she was just overwhelmed with the move, work, end of school and so forth. I'm so relieved.

Keep up the excellent work, my friends. I look forward to hearing of your escapades!

Scott

**Castlerae** · 05-07-12 20:09

Originally Posted by JoesParty [View Original Post]

My first overnight with my recent favorite is tonight. I've been eating my Wheaties and doing my stretches (as Scott is won't to say) , and so far, the day at work seems to be speeding by. The sexy talk has ramped up significantly the last few days, and she has been sending photo evidence that she has acquired the appropriate accoutrements for the evening. My only concern is with the amount of sugar, given that we've not done a sleep over before. After significant thought, I've decided to be generous and give what I consider my best and final offer. I'm not big on negotiating, and if she's not happy with it, I have at least two other fish on my lines. If she is happy with it, I think it will engender significant goodwill going forward. I really like this girl.

Wish me luck, brothers and Mandy.

Regards,

Joe

Hope you hit one out of the park, Joe.

**Fixinit** · 05-07-12 17:35

I agree with Nando that you will set the bar with tonight's overnight donation. I give the same for an overnight as I do for a normal visit. The only difference on an overnight is there is usually dinner involved which is not a big deal.

Have fun tonight and report back.

Fix

**JoesParty** · 05-07-12 14:26

Originally Posted by Hernando [View Original Post]

Keep in mind that whatever you give her tonight will set the bar for the future. If it works out and becomes a regular thing it will be very hard to take back what you have already given. Nando

Very true, and thanks for the reality check. I'm repeating the mantra "Never negotiate against yourself."

**Hernando** · 05-07-12 13:47

Keep in mind that whatever you give her tonight will set the bar for the future. If it works out and becomes a regular thing it will be very hard to take back what you have already given. Nando