"Sugarbabies" / "Arrangements" Amateurs or Not?

Not a bad idea to share a few "blind alleys" as Scott says. I have a few stories which are not spectacular in any way but nevertheless, we all fail at certain times. We tend to report our successes which gives the members-particularly the new ones. The idea that this is easy.

I prospected AM for a while and had exactly 0 (yes zero) success. Now, keep in my I am a legend in my own mind.good looking, smart, successful, studly, with a package of unopened treasures to share with the lucky Pot (SA parlance=potential sexual conquest ). You can see my words dripping with sarcasm I hope.yet, most of us think we are a good catch for a variety of reasons, each unique to us Right? I made a date with a hot looking MILF.actually bordering on GILF (grandmother I'd Like.) This chick was very well preserved indeed and I was willing to give her a chance in spite of her being 30 years older than my HCB. Well, we met at Bonefish Grill where she knew the bar staff and obviously had done this meet before. We chatted and I thrilled her with my best bon mots and she remained an ice princess-polite but not warming up to my charms WTF? She should be damn lucky that an accomplished SD like me would even waste my time with an old broad. Well Dang, whan it came time to rent a Notel she told me she just wan't feeling it and thanks for the dinner and drinks. What? How picky can a GILF be? I figured she just got guys to give her dinner and drinks.

A second AM meet was a 32 yr old HAMILF (hot almost mother I'd like.) She was smoking hot at 5'4 110 see cups and long brown hair. Again.we had a great drink together and while I was walking to the car was regretting that I had only brought a three pak of Trojan Magnums. Talk about counting my chicks before they hatch. She said call her tomorrow. I did, no answer for 3 days. Finally I got her to answer an email and she wasn't feeling it either. WTF? There are a lot of unfeeling girls here. I did figure that she probably thought I was too old. Dang! I was really looking to bget into those size 2's

Fling has a bunch of HYBs-seemingly mostly blue collar girls but the equipment still looked good. Interestingly I met and bedded a 40 yr old MILF from there, a little chubby but incredibly wild and needy in bed. But after 3 runs to the Notel she dumped me.saying that she wasn't feeling good about herself. She was too fat for me anyway.ungrateful wretch!

Anyway I could go on and on but this gives a sampler of a not infrequently occurring fail. We all have to go through this before hitting the scores. The problem with those two sites is there is usually no sugar involved. It is actually easier to pay them because he who has the gold.has the power. Nando

one of my more bizarre m&gs was with an sb whose profile heading was in french, whose pictures looked like high art shots, and whose text was well-written, flirtatious and intelligent. she says she's currently enrolled in a very well-respected university in chicago. she sounded perfect for me. (red flag, right? tgtbt!)

we make plans to meet at my favorite starbucks, the appointed day arrives and i settle in to a cozy table in the back with a view of the door and wait. right on time, a woman enters who bears a passing resemblance to the pictures on sa, but "fuzzier", like that movie that starred michael keaton, i think, who keeps cloning himself, but each time the copy is a little degraded. anyway, she sees me, smiles and heads over. after a slightly stiff greeting, (not the good kind of stiff) , i buy her a coffee and we settle in to the interview. i'm looking at her and thinking she's not going to be long-term, but all-in-all she's doable. i'll move this along quickly and set up an fd (fucking date) for a few days from then.

as we talk more, she tells me she is majoring in gender studies, and is in fact working on her senior thesis on, of all things, sex trafficking and **** prostitution in the us! as she is saying this, she is looking straight into my eyes, and i can hear her thinking "you pervert"! i gulp a little and wonder why it suddenly got warm in there, but sit back and listen quietly as she goes on and on about how all women are exploited by men, what scum we are, how just the act of sex enslaves a woman, the myth of the empowered stripper is just that, a myth, and so forth. i am thinking to myself,"how does she manage to keep talking without taking a breath?" and i amuse myself for a few minutes looking for gills. meanwhile, she is warming to her sermon, and her eyes are beginning to bug out and she is getting progressively louder and louder, to the point that people are looking at us. they can clearly hear her shouting "prostitutes, johns, pimps, slavery" and other such inflammatory words, and i am looking around for the emergency exit.

finally i make a huge show of looking at my watch, and pretend that i'm late for something, [i]anything[/i] actually. we stand to go, and startlingly she smiles, gives me a hug and says,"so, will i see you again?" "not if i see you first" is what i'm thinking, but of course i tell her i will call her when i get some time, but that my work is pretty hectic at the moment. she gets a look on her face that indicates that she's heard that one before (what a surprise) , and we go our separate ways, with me thankful that i did not get pepper sprayed, which i'm pretty sure was just around the corner if she had been allowed to continue her tirade.

so i'm wondering what was up with that? i still see her profile on sa, so she is still trying to set something up, i guess. or maybe she just gets off on luring unsuspecting sds to meet with her so she can snip their balls off verbally. it took me a full day to lure little scottie out of his hiding place, and i really don't blame him one bit. fortunately, i soldiered on in my pursuit of hybs, but that was enough to put me off my feed for a week or so. whoo, got the willies just thinking about it!
be careful,
scott

It looks like the pickin's down south are much better than the ones on the northern side of the Old Dominion. Good job, gents!

Guys. That's is outstanding advice and never to be forgotten. When SB1 called me. 2 hours late & lost on the route she has taken 3 times before, I played the ultimate gentleman. Where are you. I will come get you. No whining bitching or moaning. Now I have a friend for life as I am the only guy in the world who wouldn't denigrate her in that position. Earned me a free extra visit per week! The warden would put up with nothing less but there are scores of women out there who get treated like Sh$t. Stay on your game. It pays.

[QUOTE=F Scott; 1398354]So I'm wondering what was up with that? I still see her profile on SA, so she is still trying to set something up, I guess. Or maybe she just gets off on luring unsuspecting SDs to meet with her so she can snip their balls off verbally. It took me a full day to lure little Scottie out of his hiding place, and I really don't blame him one bit. Fortunately, I soldiered on in my pursuit of HYBs, but that was enough to put me off my feed for a week or so. Whoo, got the willies just thinking about it!

Be careful,

Scott[/QUOTE]Scott:

I think you have a duty to the boys here to go f*k this militant young gal and report back the sordid details. Oh, she could be a real molitoff cocktail to go off in the sheets; since she may not get too many takers with that warm-up act of hers. You can sure find them brother. J / k about takin this down low. As always, enjoyed the story or your meeting. V

Gentlemen,

Polo and I are set for tomorrow. In addition to her Sexy Self, she wants to bring a picnic and some wine as well, so that we can keep our strength up, I guess. I'm delirious with anticipation, and feel like I could easily get used to this. I have cancelled my early afternoon appointments to give us enough time to go back over her list from Monday.

The bad news is that for the next week or so I will need to have my nose firmly pressed against the grindstone, so no auburn pussy for me. I will have to make tomorrow count.

The flood of sex talk has diminished, but I don't really mind. I know she is someone who can walk the walk, not just talk the talk, though she did oblige me with a pussy-wetness update when we spoke. The heat index is high, apparently, so I am already doing my limbering-up exercises.

ATF and I have lunch plans for Friday, but it can't be more than that, at least on my schedule. Her birthday is Sunday, so I have a little gift for her that I know she will like. I can't wait to see her smile.

Best to you all,

Scott

[QUOTE=Varoom; 1398457]Scott:

I think you have a duty to the boys here to go f*k this militant young gal and report back the sordid details. Oh, she could be a real molitoff cocktail to go off in the sheets; since she may not get too many takers with that warm-up act of hers. You can sure find them brother. J / k about takin this down low. As always, enjoyed the story or your meeting. V[/QUOTE]Vroom,

I'm not sure about that. I'm picturing the final scene of "Looking for Mr. Goodbar", but with me in the role of Diane Keaton. No thanks, though I bet a taste of Scottie Steel would realign her priorities LOL!

" ATF and I have lunch plans for Friday, but it can't be more than that "

THere are two lessons we all can learn from Scotts journey.

1) We are ALL replaceable.ATF has essentially been replaced by Polo girl even when Scott was wildly in lust with her. And;

2) Stick with a good thing if you have it.ATF HCB screwed herself and her good deal with Scotty by playing games with another guy and with Scott's emotions

[QUOTE=Hernando; 1398493]" ATF and I have lunch plans for Friday, but it can't be more than that "

THere are two lessons we all can learn from Scotts journey.

1) We are ALL replaceable. ATF has essentially been replaced by Polo girl even when Scott was wildly in lust with her. And;

2) Stick with a good thing if you have it. ATF HCB screwed herself and her good deal with Scotty by playing games with another guy and with Scott's emotions[/QUOTE]Listen to this man. He speaks great wisdom.

[QUOTE=Hernando;1398327]I have a few stories which are not spectacular in any way but nevertheless, we all fail at certain times. We tend to report our successes which gives the members-particularly the new ones. The idea that this is easy.[/QUOTE]Again, listen!

[QUOTE=Varoom; 1398457]Scott:

I think you have a duty to the boys here to go f*k this militant young gal and report back the sordid details.[/QUOTE]F*ck that!"Militant" and "Sugarbaby" do not go together! Master Scott not only does not need this, he should do something medically to have it removed from his memory! No doubt that little scotty would set Ms. Wacko straight, but why ever go there? LOL.

Didn't happen to me, but, was related to me by a SB candidate. She meets some guy for a "meet-and-greet" and he is somewhat hesitant. When she inquires as to why, he tells her that the last time he was out with a possible SB, he and the MILF type lady met in a nice restaurant, start having a drink and dinner, and who walks in? Her husband! He walks up to the table and, wait for it, starts to beg her to come home and don't do this! To the point of getting on his knee's! Needless to say, Mr. Daddy was mortified till she left with hubby in tow and he could bail. Yikes! Talk about a bad day.

Stay safe.

Strict

[QUOTE=Hernando; 1398493]" ATF and I have lunch plans for Friday, but it can't be more than that "

THere are two lessons we all can learn from Scotts journey.

1) We are ALL replaceable. ATF has essentially been replaced by Polo girl even when Scott was wildly in lust with her. And;

2) Stick with a good thing if you have it. ATF HCB screwed herself and her good deal with Scotty by playing games with another guy and with Scott's emotions[/QUOTE]Nando,

You have rarely steered me wrong, my friend, but I think I am not [I]over[/I] ATF, just able to view the situation with a little greater clarity and perspective. In truth, I thrust ATF-dom upon her, in a sense. She never really asked for it, and perhaps like any old fool, I chose to think that I was [I]her[/I] ATF, when perhaps I am not. I will not stop seeing her, unless she does another vanishing act, nor will I stop fishing for new little babies either. I just can't be so obsessed with her anymore. Despite what she says, she may just not be as into me as I am to her.

As with so much in life, moderation in all things are the watchwords. Certainly my current infatuation with Polo mom has helped. Up til now, the babies have been curiously interchangeable in a way. Sure, they have all had their own identifying characteristics - boob size, favorite position, tats, accent, and so forth - but for me the main attraction has been the fucking. Polo may just prove to be the whole package for me, the way ATF is. I will need to have some actual conversation with her tomorrow to see. The Irish in me values verbal communication, sometimes the wordier the better, as long as it's rich and substantive.

For something that should be all about the kitty, there is a surprising amount of contemplation that goes into this hobby, isn't there? At least for me.

For those with nothing better to do, look for a post from me around 3 o'clock or so.

Peace, my brothers,

Scott

[QUOTE=Mr Strict; 1398524]Didn't happen to me, but, was related to me by a SB candidate. She meets some guy for a "meet-and-greet" and he is somewhat hesitant. When she inquires as to why, he tells her that the last time he was out with a possible SB, he and the MILF type lady met in a nice restaurant, start having a drink and dinner, and who walks in? Her husband! He walks up to the table and, wait for it, starts to beg her to come home and don't do this! To the point of getting on his knee's! Needless to say, Mr. Daddy was mortified till she left with hubby in tow and he could bail. Yikes! Talk about a bad day.

Strict[/QUOTE]Now that would take the snap out of your sails, wouldn't it? The only thing worse would be if the MILF did not leave, but stayed to see the deed to completion. Talk about a gorilla in the corner all night long!

Scott is correct in opining that a SB might have different feelings for her SD than we do. This is a very good point. My SB says all the right things to me and does all the right things when we are together but in the end, does she have the intensity of attraction that I do? It is always better in this game to keep a little bit of yourself back and not invest so much emotion. The ending would therfore be less traumatic when it inevitably comes.

My problem being married is that hunting is risky. So having found a perfect ten for me I am throwing all of my time and Sugar into this one Baby. If I wanted to hedge my bets then I would have to cut back on my beloved baby, see less of her, then prospect for a backup player. A result of that is my SB would sense a change like SCott did, sand pull back herself or start looking for my replacement. Sheeesh! It aint easy babe!

My solution to this conundrum is to put 100% into my SB and continue to ride this one out. Like Scott, if a back up occurs and the SB plays a rabbit, then move on forthwith and not spend time mooning around. Scotty got up off the ground and found a new Mare.

Gentlemen,

I wish that I could truthfully say that I have been bedded down in Polo's Pleasure Dome for the past nine hours, but alas, that was not the case. We did meet as planned, and it was mind-alteringly erotic, but I felt compelled to do some actual work this afternoon, and so am only now able to post up.

We met this morning, back at what we are now calling "our hideout", and rather than getting straight to it, I told her that I wanted to know a little more about her. She then proceeded to tell me she has a masters degree in psychology, has traveled extensively in Europe and North Africa, is from a family of three, all women (I'd like to meet the other two) , and really had planned to go on to get her PhD, but instead met Douche Bag, got pregnant, and that was that. She has a love of reading, is proud of her Irish heritage, is interested in architecture (which is what I do) , and loves all kinds of music, art, and is a great cook. I'm done for!

As we were talking, she was looking straight into my eyes, touching me softly here and there, but in a tender way, not like "let's fuck", and generally, it seemed to me, enjoying spending time with someone who was genuinely interested in who she was as a person. I need to digress here just a second, and admit that while Big Scottie was interested in her as a person, Little Scottie just wanted to dive head-first into her pussy. This went on for a good half hour or more, during which time we touched each other more frequently, and moved closer, until it just became obvious what was up next.

Let me just say, she was as hot as Monday. A pale pink cotton blouse, a short black skirt, and velvet slippers with the RL monogram on them. No tights this time, but no panties either! Scottie almost broke the zipper of my khakis trying to get out when we discovered this last fact. Honestly, she is my Catholic schoolgirl dream come true. Buttoned down on the outside, but crazed for fucking just under the surface. We didn't even make it to the bed before I was pounding into her from behind, gazing down at her pale skin and seeing if I could count all the freckles on her shoulders before we switched positions.

My brothers, I am feeling a little squeamish all of the sudden about sharing every detail, which is an indicator of sorts for me, but suffice it to say that she was well-rested, agile, and inventive. When we mutually agreed to a cease-fire, she opened the basket she had brought, and laid out an outstanding picnic lunch for us that was partly store-bought, and partly home made. It was wonderful, actually, and I had to marvel at her thoughtfulness and attention to detail. Her husband must be a real jag-off not to appreciate her, but who am I to complain?

After we finished, she told me she would like to just be held for a while, which I was also thinking, so we sat in bed for a bit, just enjoying each other, until things went where they normally do when I am naked at the same time I am also in close proximity to a naked woman, and we finished our time together with a less-frenzied but still satisfying aerobics session. I really think I could get hooked on her.

Now, if I were to be completely honest, I would have to confess that I am worried that she will start to see me as her next husband, which is something that I fervently want to avoid. On the one hand, I want to keep seeing her as often as our schedules allow, but on the other hand I don't want her to get to focused on me as the solution to all her problems, and, as I have said, her train out of Shitville. Luckily, my work schedule for the next two weeks does not afford me any playtime, so I am hoping that things will cool down sufficiently. I don't want to come home and find a boiling bunny on my stove, but I think we are far from that.

Birthday lunch with ATF tomorrow. Could you call me conflicted? "Yes" is the correct answer. We shall see.

In the meantime, keep up the good work.

Scott

[QUOTE=Hernando;1399108]It is always better in this game to keep a little bit of yourself back and not invest so much emotion. The ending would therefore be less traumatic when it inevitably comes.[/QUOTE]I will do my best to try and embrace the wisdom that Nando imparts here. Everything has an end - the drama comes when we are incapable of accepting that. Let us all enjoy our good fortune as it is given to us. Never in a million years did I suspect that I would be fucking babies who were born [I]after[/I] I turned 30. Life is good.

Scott

I don't have time for a full blown detailed review. But I just wanted to update my peeps on my unexpected double-dip day. I had a morning meeting setup with my Hottie in Richmond. She has turned out to be a absolute great find. We we had our 2nd Tiggabounce date scheduled for the morning at 8am. We met at the hotel that morning and had a blast. We ended our event right about 12pm with lunch at a local establishment.

Meanwhile the previous two nights I'd had two regular dates with MsBeautiful. I had told her I could get free that evening if she were available. We exchanged a few naughty texts during the day and before you know it, I'm showing up at her place with wine and condoms ready to roll! It was such a surprise and I was so excited. The perfect mix of trophy fuck and young tender all wrapped up in one. Although we had a good time, I sensed that the chemistry wasn't quite the best. I left fulfilled, she had her orgasm, but I'm not sure we'll link up again. I will say that unlike some others, she looked even better naked. Oh my my what a body.

Oh, as is the case with me, the sugar has went up as we date more.
MsRichmond $.6
MsBeautiful $.2 (She was a CL find, so I always keep them lower)

Moving forward, MsRichmond is definitely my #1. I have MsNJ coming up next week. I'm not sure about tasting the goodies on that one. But I will definitely try.

I have my young chubby one from MD that I expect to hit soon, she doesn't drive and has cancelled the last few. I'm not sure when I'm going to hit that as I'm still trying to link up with the white MILF in Richmond.

Right now, seems like I'll keep my focus on my new #1 and slide the others in when I have open windows of time.

BigTigg