"Sugarbabies" / "Arrangements" Amateurs or Not?

[Walruscl]

The eternal quest for perfection, however you define that. The ideal here seems to be very attractive, able to make a personal connection. Low-risk / overhead / drama (I.e., no Nando-1's), and inexpensive (the gold standard being $ or so). I believe that I have hit the 20/80 mark for my quest in perfection. Could I find something better? Probably. Do I have the time? Do I want to take on additional risk? Answer to both is "no". I've probably hit 80% of perfection with 20% of the effort. The rest is an asymptotic curve, at least based on my experience and from reading the board.

In my relatively short search, I ran into flakes, GPS, UTRs, girls who would have struck a deal but I didn't have a connection with, a couple of POTs that had sudden cold feet, and one situation where I blew it but probably turned out for the best. It was long, time-consuming, and emotionally exhausting. For all her shortcomings, nothing "clicked" like my current SB.

One of the early POTs was a HCB (at least from the pics) and we exchanged quite a few emails. We had incompatible schedules and she was a bit too far away. But bright, interesting, a normally-straight-and-narrow girl looking to explore her wild side while she still could. Unfortunately between the barrage of creepsters on SDFM and suddenly faced with the decision to actually move ahead with a face-to-face, she panicked. To her credit, she was very up-front about it and didn't just flake on me. Allegedly she found me too attractive (at least based on my writing style) and claimed to be afraid that she would fall for me. Normally I would call BS on something like that, but the emails were pretty deep and sincere. It was my first experience with getting too invested too early-really hard to let it go even though I knew it was the right thing to do.

My "close-call" was a HYM in her late 20's. Stable job, two kids, attractive if a bit lacking in chemistry. Things were going really well over text, we had a MTG that went well, but she sensed my hesitation and insisted that I really go into this "ready", whatever that means. In the meantime, she had car trouble which postponed another MTG. The way she presented the whole car thing set off scam-alerts and got me paranoid. Too paranoid, and when I confronted her about it (over texts-stupid of me), I'm sure I came across as a creeper and she bailed. Still thoroughly paranoid, I rooted out her Facebook page and a lot of things didn't align with her story. The biggest being her relationship with her ex, which she played down as more or less out of the picture. Well, the Facebook pages told a different story (lots of recent "happy family" pics). Not only that, this guy was an Army vet with lots of pics of large biceps, fatigues, and guns. God only knows what I could have been in for if things proceeded but then went sour. (shudder).

So my SB is not a conventional beauty (until she shows that spinner body), has some drama issues, and performance could be better. It's pretty clear that she's probably getting the better end of the deal sex-wise. I see that as a work-in-progress, and I get a lot of pleasure from seeing her all but worship me as a sex god. That sounds over the top, and if you told me that five years ago I would have laughed. But it's not much of an exaggeration. And from the board it's clear that many of us have had that mind-blowing, game-changing experience.

So... Checking in. Had another five hour romp in the FC. With the sudden warm weather she surprised me by wearing a dress but nothing underneath. Soooo hot to have her on top but still clothed. I had a concall scheduled midday which we decided we would work around. Well, that consisted of her blowing me during the entire call, and became a battle of sensory overload vs concentration. I'm happy (I think) to report that the latter won out. Once the call was over, we spontaneously proceeded to act out a fantasy that we apparently both had-she mounted me on the chair and went to town.

By the time it was over she could neither walk straight nor think straight. Even though I only popped once, it was friggin amazing to be able to fuck someone silly.

Ah, finally getting the sex life I never had...

[Revvo]

Well I guess this comes under the category of careful what you wish for...you just may get it! So for a very long stretch of time late October through early February I was either having no luck with the babies or going through total duds or just spinning my wheels and wasting time, or taking a break out of frustration. And then all of s sudden in mid Feb. Things started to look up. They really started to look up. I mean the pussy was coming at me from all directions. They were mostly contacting me. Then I met my current favorite that is heading straight into ATF territory. You can read all about her below my little Italian Princess. Things are getting better and better. I did her on Monday and it was one of those magical days. Where when we were done there was some real afterglow. And that is saying something because she is not particularly expressive emotionally. I was happy and she was happy and she said so. So the dilemma:

About a week ago I was contacted by a really nice divorced MILF 37 YO white also bright blue eyes and gorgeous, probably 5'7" and a size 8, and also I believe Italian descent. Did not think nothing of it. I responded politely but did not really intend to meet with her. But we got into some nice conversations and found out she just moved into the area was educated had her own house a son and her own job and nice car. She also talked about how she was not looking for a lot and was not into this to see how much money she could get out of me. She talked about a lot of the same things I was looking for and swears she has never done this before, she was convinced by her friend. Remember women live their lives on plausible deniability. So I was a little skeptical. But I am committed to my current beautiful sexy fun baby. But hey what would it hurt. Like some of the brothers said maybe she could be a fallback if things go bad in the next few weeks.

So I casually entertained her interest and mine grew. She was sweet, a bit frazzled from her move, seemed honest and very very sweet and she seemed to genuinely like me. So we talked some more and met today. She is absolutely beautiful, stunning, and a little thick, great titties, and firm body. Very affectionate and passionate. We talked and laughed and the chemistry was very very intense. I can tell you since I have been doing this I have rarely felt this good of a connection. She could not say enough sweet things about me and to me. I had a hard on already. We could not keep our hands off of each other. And it was so easy and natural. But the sexual tension was high. I give her a 10/7/9/? . She tells me she won a major pageant several years ago and I tell ya brothers she is not skinny but she is not fat either, and if she lost 15 lbs that 7 rating would go to a 9.

I was absolutely not expecting this. I am very happy and committed to my current beautiful baby. She is pushing all of my buttons very well. But this baby is a cut above on the passion affection front and she is not asking for much money and has her own place to meet and wants to accommodate me. I walked her to her car and we crashed into each others arms, we were at a private spot in the parking lot so no one could see us. The making out was hot and heavy and man we almost were not able to stop. We were standing up and no parts of our bodies were left untouched at least once. I almost thought I could get her in the car and fuck her there but she started to back off as were were really getting into it. But she had a plumber going to her house. She is ready to meet soon and do some serious fucking.

What should I do? Its not fair that she has to come along now and upset the apple cart. I honestly did not think any baby could turn my head. But I must say it is officially turned. She was adamant that she wants one man, and only one and she has had very few men her entire life. I could do her once but that would not be good form. I can tell her I do not want to proceed but that would not be good for me and my sexual craving for her. I have the whole rest of the week free to try her out since my baby is busy the next two nights with a photo shoot for a promotion she is doing. So I will not even see her until next week. Or I could take her on for a month do both of them spend lots of money and then make my decision. What should I do?

This is not fair. Or is it?

Revvo.

[HollywoodGuy]

Jeez, you are making it happen. Way to go brotha. I am impressed by the same day FCs. This is all about being bold without being a douche. Women not only admire that they are turned on by it. Which is what you found with your baby with the nasty attitude. Once you stepped in the drivers seat and took charge she really got turned on and then she really had some good orgasms.

This goes for most women. And what you said about her not even knowing how to take charge, so damn true. And when the man does not lead they try to lead and it comes out just like she did, mean and clueless.

Great info keep it coming. There is gold In here brothers. Brother Jeez is on the fast track to tons of quality pussy.

Revvo.

Same day FC's are actually easier than planning ahead. Many times girls agree to my $ and the first thing they want to know is can I see them today. At that moment they are in a state of financial desperation that could end in a day or 2 and many times does. Being in a state of constantly being overbooked and overworked its not easy for me to follow through on such short notice. I have even had 9+ quality girls agree to this. And even if I do rush over or have them come over. They many times decline a repeat visit. Being able to be as spontaneous as possible definitely increases your closing rate.

[Revvo]

Boy that last line really rings home with me right now. I recently had a college girl who turned into an all-nighter, thus multiple sessions and pops. But in-between sessions things started to go sideways, and I was able to defuse and recover despite her increasing bitchiness and anger. One of the reasons it started to go bad is I guess the alcohol was putting her in the mood to test the boundaries of her dominance, and it took me a while to figure out what it would take to get things back on track, as I was having a good night physically and wanted still more sex. So a bit of tact and charm to defuse the situation, then once the anger was gone I showed a more dominant attitude than she had seen before, literally instructing her on what she was going to do to please me. Bingo... That firm side of my personality struck all the right nerves with her, this final session was the best, she was the most orgasmic during this final and more epic session than the prior ones.

Moral of the story -- always be the boss. Don't for one second let her feel she is in charge of the situation, because whether she realizes it or not, she doesn't really want to be. She also is not qualified to be.

Also some have mentioned how great it is to be their first. Only happened to me once and yes it was the best. I think I have an opportunity to do same this weekend I'm looking forward to, although I'm stopping myself from assuming the date will end in sex. So far, I've had 100% success rate with that banging them within a few hours of initial M&G but I know I'm still new at this and have not seen everything.

Jeez, you are making it happen. Way to go brotha. I am impressed by the same day FCs. This is all about being bold without being a douche. Women not only admire that they are turned on by it. Which is what you found with your baby with the nasty attitude. Once you stepped in the drivers seat and took charge she really got turned on and then she really had some good orgasms.

This goes for most women. And what you said about her not even knowing how to take charge, so damn true. And when the man does not lead they try to lead and it comes out just like she did, mean and clueless.

Great info keep it coming. There is gold In here brothers. Brother Jeez is on the fast track to tons of quality pussy.

Revvo.

[JZLizard]

Great comments. Every once in a while I need to be reminded of this point. That it is better to ask for what I want or just do it. And I have found that women like that even if they don't want to do what you are asking they will admire your leadership and willingness to push the envelope a little.

Boy that last line really rings home with me right now. I recently had a college girl who turned into an all-nighter, thus multiple sessions and pops. But in-between sessions things started to go sideways, and I was able to defuse and recover despite her increasing bitchiness and anger. One of the reasons it started to go bad is I guess the alcohol was putting her in the mood to test the boundaries of her dominance, and it took me a while to figure out what it would take to get things back on track, as I was having a good night physically and wanted still more sex. So a bit of tact and charm to defuse the situation, then once the anger was gone I showed a more dominant attitude than she had seen before, literally instructing her on what she was going to do to please me. Bingo... That firm side of my personality struck all the right nerves with her, this final session was the best, she was the most orgasmic during this final and more epic session than the prior ones.

Moral of the story -- always be the boss. Don't for one second let her feel she is in charge of the situation, because whether she realizes it or not, she doesn't really want to be. She also is not qualified to be.

Also some have mentioned how great it is to be their first. Only happened to me once and yes it was the best. I think I have an opportunity to do same this weekend I'm looking forward to, although I'm stopping myself from assuming the date will end in sex. So far, I've had 100% success rate with that banging them within a few hours of initial M&G but I know I'm still new at this and have not seen everything.

[Revvo]

I grew up reading playboy. And I always used to think that HH was such a lucky guy. Not because he had so many girls, but because he has stated in many interviews that when it comes to sex he is strictly a plain vanilla type of guy. Just stick a pair of D's and some blond hair on an admittedly hot body and the guy is home free. And I was just gonna have to suffer because that just wasn't gonna do it for me. Even something as common today as inter racial dating was unthinkable in high school. A major factor in my moving to los angeles, where it's basically anything goes.

My tastes are far more eclectic. At 18 to about 25 I was happy to just get whatever girl fell into my lap. Even after I met my 2nd wife who was a whole lot better in bed than most of the girls I had known I still had to put away some of my fantasies and desires. At 55 I decided I was just going to get what I wanted one way or another. Now. OMG. Either the girls of today are way more experimental, freaky and what they like to call sex positive or my ability to bring it out of them has increased to the point of where I really am going to get just about anything I want out there.

And if money wasn't a factor, I would get anything and everything, anytime I wanted.

Never be afraid to ask or just go for it (as many submissive and very young girls can be shy). If one won't do it the next one will. I find a major factor in younger girls (or any girl) dating an older guy is to get freaky. They are ho hum bored with most younger guys. I,m sure I wasn't all that exciting myself back then. When they call me an animal, a perv, a sex addict or a freak, its always with a smile on their face.

And of course the real joy is knowing you are the first guy they ever did it with.

Great comments. Every once in a while I need to be reminded of this point. That it is better to ask for what I want or just do it. And I have found that women like that even if they don't want to do what you are asking they will admire your leadership and willingness to push the envelope a little.

And of course being their first is always a treat too.

Agreed.

Revvo.

[HollywoodGuy]

I grew up reading playboy. And I always used to think that HH was such a lucky guy. Not because he had so many girls, but because he has stated in many interviews that when it comes to sex he is strictly a plain vanilla type of guy. Just stick a pair of D's and some blond hair on an admittedly hot body and the guy is home free. And I was just gonna have to suffer because that just wasn't gonna do it for me. Even something as common today as inter racial dating was unthinkable in high school. A major factor in my moving to los angeles, where it's basically anything goes.

My tastes are far more eclectic. At 18 to about 25 I was happy to just get whatever girl fell into my lap. Even after I met my 2nd wife who was a whole lot better in bed than most of the girls I had known I still had to put away some of my fantasies and desires. At 55 I decided I was just going to get what I wanted one way or another. Now. OMG. Either the girls of today are way more experimental, freaky and what they like to call sex positive or my ability to bring it out of them has increased to the point of where I really am going to get just about anything I want out there.

And if money wasn't a factor, I would get anything and everything, anytime I wanted.

Never be afraid to ask or just go for it (as many submissive and very young girls can be shy). If one won't do it the next one will. I find a major factor in younger girls (or any girl) dating an older guy is to get freaky. They are ho hum bored with most younger guys. I,m sure I wasn't all that exciting myself back then. When they call me an animal, a perv, a sex addict or a freak, its always with a smile on their face.

And of course the real joy is knowing you are the first guy they ever did it with.

[HollywoodGuy]

My experience with jail birds, and I've had a few, is that they are always Nando 1 s. Living in hotels is another tip off and frequently they were incarcerated for prostitution or drugs. These girls are desperately poor, in great life trouble, and you would be best off avoiding them. It's easy to feel sorry for them and want to be the white knight. BTW, These residential hotels in my area charge $250 / week and do not require credit checks. Paying these girls $250 + is over the top. They will suck you dry and spit you out.

One of these I was enamored of, and put her up rent free in a rental house I have. It took me 6 mos to get her and her druggie BF out and still worried about Black Mail.

One of the reasons I have a roommate (aside from loving her. LOL) is to keep the desperate ones from thinking they are moving in. And even with her here they still try. And I will never move one into a place where my name is attached to the lease. Been there, done that, gotten burned.

[FredMoore]

My experience with jail birds, and I've had a few, is that they are always Nando 1 s. Living in hotels is another tip off and frequently they were incarcerated for prostitution or drugs. These girls are desperately poor, in great life trouble, and you would be best off avoiding them. It's easy to feel sorry for them and want to be the white knight. BTW, These residential hotels in my area charge $250 / week and do not require credit checks. Paying these girls $250 + is over the top. They will suck you dry and spit you out.

One of these I was enamored of, and put her up rent free in a rental house I have. It took me 6 mos to get her and her druggie BF out and still worried about Black Mail.

I offered 240 but she asked for 260. But I really need to work on getting my CPO down. In retrospect, my initial offer should have been much less. I'm trying to learn from the senior members here.

Back to the Craiglist ad, most replies are going to be losers or bots. But there is an occasional gem out there. I am single and it is mentioned in my ad so that helps some too I guess. I still have dreams about the college co-ed that almost agreed to meet last summer. Not necessarily a knock-out but the cute girl next door type. I'm pretty sure that she had never had a SD and may never, but she came close. You never know.

[HollywoodGuy]

I offered 240 but she asked for 260. But I really need to work on getting my CPO down. In retrospect, my initial offer should have been much less. I'm trying to learn from the senior members here.

Back to the Craiglist ad, most replies are going to be losers or bots. But there is an occasional gem out there. I am single and it is mentioned in my ad so that helps some too I guess. I still have dreams about the college co-ed that almost agreed to meet last summer. Not necessarily a knock-out but the cute girl next door type. I'm pretty sure that she had never had a SD and may never, but she came close. You never know.

Cast a wide net. Make tons of offers at $. Get tons of rejections. But then when they agree at least you feel like you got some value.

[ChipandPutt]

Chipandputt. I am thinking of trying the Craig's list thing again. The last time I tried it just got a bunch of losers.

What was the damage for strawberry girl?

I offered 240 but she asked for 260. But I really need to work on getting my CPO down. In retrospect, my initial offer should have been much less. I'm trying to learn from the senior members here.

Back to the Craiglist ad, most replies are going to be losers or bots. But there is an occasional gem out there. I am single and it is mentioned in my ad so that helps some too I guess. I still have dreams about the college co-ed that almost agreed to meet last summer. Not necessarily a knock-out but the cute girl next door type. I'm pretty sure that she had never had a SD and may never, but she came close. You never know.

[HollywoodGuy]

They don't all work out. Claims she (first pic) found a more generous SD. Probably true. My date tonite (second pic) turned down triple the $ I paid her from another guy, cuz she likes me. So never get too hung up on one girl. There is always a better one out there.

Break up girl - 7/8/7/7

Date tonite girl - 8/8/9/8

[HollywoodGuy]

I am primarily on SA, and occasionally I get the random wink or email from a girl who is not even close to me. Demographics tend to AA, but not always. I've gotten a couple from ABQ (I live in PHX) which is close on the map but not in real time, including one today from a stunner. I generally send a polite reply, 'cause who knows?; but don't really take it seriously. I assume GPS or someone phishing for a sucker. My question is, anyone ever scooped an out of state girl at random that wasn't prohibitively expensive? If so, how did you mange the logistics?

For me I never do this. But I see many members have jobs that require travel. Girls that like to travel or a need for some anonymity that can only be achieved through a little distance... I,m sure many past posts touch on this subject.

[Dsprdo]

I am primarily on SA, and occasionally I get the random wink or email from a girl who is not even close to me. Demographics tend to AA, but not always. I've gotten a couple from ABQ (I live in PHX) which is close on the map but not in real time, including one today from a stunner. I generally send a polite reply, 'cause who knows?; but don't really take it seriously. I assume GPS or someone phishing for a sucker. My question is, anyone ever scooped an out of state girl at random that wasn't prohibitively expensive? If so, how did you mange the logistics?

[HollywoodGuy]

After a couple more emails. This girl pointed out to me that she is not emotionally needy in any way. For me, this is why I go the SB route. I need the emotional connection to get what I am looking for. Some good sport fucking with a random girl is all good and well, but for an ongoing relationship there has to be a real connection, even if it is more one sided. But without it I am going to lose interest eventually (usually in under 10 dates), and especially if there are any items missing from the menu.