"Sugarbabies" / "Arrangements" Amateurs or Not?

[QUOTE=F Scott; 1375567]Gentlemen,

I hope you all remember the saga of me finding an old employee on SA, contacting her as my alter-ego, and indulging in sexy talk and ultimately getting some outstanding naked pictures from her. Well, yesterday I took it one step closer to the edge of the cliff, so to speak, and I'm kind of conflicted.

I contacted her and arranged a "meeting" in the city on the steps of the Art Institute. I told her that we could take a look around inside if she wanted, or go to a nearby Starbucks and talk. The weather here has been unseasonably warm, so I did not feel bad about asking her to stand outside to wait for me. The plan was to drive by until I saw that she was there, then take off and text later saying something had come up. My thinking here was to see if she still looked as hot in person as she did years ago, and maybe get a little thrill out of it in the bargain.

All went off as planned, and I got a visual confirmation that the hotness quotient is still as high as ever, contacted her later with my "excuse", and that was that. [B]except[/B]: I now feel really guilty that I jerked her chain and made her waste time waiting for me when I knew full well that I wasn't going to show up just to add to my personal fantasy script. I guess I am sharing this with the brotherhood with the intent of reminding us all, myself included, that many of these little babies are not masquerading pros, they are real people, with real lives and feelings, and we should do as Lit so wisely counseled,"do no harm" or something like that. I may try and figure out a way to send her a few grains of sugar to assuage my guilt. Or I could wait a few more days until it passes, which I know it will.

Scott[/QUOTE]Maybe a small gift card, if you can get it to her without any trail back to you. Have a random kid leave an envelope at the store with her name on it, then email her to go in.

Considering that she used to work for you, and knows your real name and business, I'd recommend not trying to take things any further.

[QUOTE=F Scott; 1375567]Gentlemen,

I hope you all remember the saga of me finding an old employee on SA, contacting her as my alter-ego, and indulging in sexy talk and ultimately getting some outstanding naked pictures from her. Well, yesterday I took it one step closer to the edge of the cliff, so to speak, and I'm kind of conflicted.

I contacted her and arranged a "meeting" in the city on the steps of the Art Institute. I told her that we could take a look around inside if she wanted, or go to a nearby Starbucks and talk. The weather here has been unseasonably warm, so I did not feel bad about asking her to stand outside to wait for me. The plan was to drive by until I saw that she was there, then take off and text later saying something had come up. My thinking here was to see if she still looked as hot in person as she did years ago, and maybe get a little thrill out of it in the bargain.

All went off as planned, and I got a visual confirmation that the hotness quotient is still as high as ever, contacted her later with my "excuse", and that was that. [B]except[/B]: I now feel really guilty that I jerked her chain and made her waste time waiting for me when I knew full well that I wasn't going to show up just to add to my personal fantasy script. I guess I am sharing this with the brotherhood with the intent of reminding us all, myself included, that many of these little babies are not masquerading pros, they are real people, with real lives and feelings, and we should do as Lit so wisely counseled,"do no harm" or something like that. I may try and figure out a way to send her a few grains of sugar to assuage my guilt. Or I could wait a few more days until it passes, which I know it will. Meanwhile, no more joy with my ATF. It may be over for good. I know I keep whining about this, and if I am becoming tediously similar to that guy in high school that we all tried to avoid because he was such a downer, please someone let me know.

Otherwise, keep up the good work. I have had several enjoyable exchanges via pm with a number of brothers, and I urge you all to dedicate yourselves to your pursuit of your little fish, and then let us know how it went.

Lastly, Lit, your post about the first touch under the panties and so on. Pure poetry. Would you be willing to call me and talk like that some time? (just kidding)

Scott[/QUOTE]I know I'm not the most senior poster here, but it seems to me like you're getting addicted to playing with fire. Question: if you were driving your own car (and you don't say you were in a taxi in your post) , what would have happened if she'd recognized it, and started putting the clues together? Maybe you should send her a little something for toying with her all this time, but it might also be a good idea if you let it go. As the old saying goes, there's pushing your luck, then there's doing something really stupid. Maybe it's time to start thinking about which one you're doing?

[QUOTE=Bunker Buster; 1375644]Maybe a small gift card, if you can get it to her without any trail back to you. Have a random kid leave an envelope at the store with her name on it, then email her to go in.

Considering that she used to work for you, and knows your real name and business, I'd recommend not trying to take things any further.[/QUOTE]That's good advice.

Scott, if you arrange a real meeting prepare for her to feel betrayed. She'll know you knew it was her all along. It could get messy and nasty very quickly!

Agree with you Spitfire. Too dangerous for me. Time to move on.

[QUOTE=Castlerae;1375725]Question: if you were driving your own car (and you don't say you were in a taxi in your post) , what would have happened if she'd recognized it, and started putting the clues together? Maybe you should send her a little something for toying with her all this time, but it might also be a good idea if you let it go. As the old saying goes, there's pushing your luck, then there's doing something really stupid. Maybe it's time to start thinking about which one you're doing?[/QUOTE]Castle,

I have a new car since the time she worked for me, so I wasn't worried about that. Pushing my luck is probably more the speed of things. I may put a gift card in an envelope with her name written on it and put it under the door where she works some evening after they're closed. I will write with my left hand, of course, so she can't recognize my writing, then send her a final email saying goodbye.

It's all fun and games until someone gets an eye poked out, and that could be me.

Go Patriots!

Scott

The post below was made on Jan 11th, predicting that you would be parting her flesh within 3 wks or so. So now we are about 3 wks from those comments below and you are making an date to meet, (or meat). Even though you backed away and certainly intended to without meeting her. But, I'm still not convinced that there will be NO parting of the flesh with this young lady before it is over with. Not a judgmental comment here, but I am not surprised that you set the meeting with her at this time, and it will be interesting to see if it is truly "over with" at this juncture. I'm guessing little Scotty is going to comment on this subject from time to time, and at some point Big Scotty is going to listen to varying degrees. I'm still not convinced that the parting of the flesh is off the table (or bed). Wish you luck on the turnout, however it ends.

[QUOTE=Varoom; 1357160]My original thought then when first reading about your plans to pursue and see if you couldn't entice her to send photos was, Oh boy. Scotty's will power will be under assault soon, and doubtful that once you get some encouragement from a half-begging naked Latino gal, that little Scotty is going to be able to refrain.

So I suppose I am saying that you will be parting her flesh within say, the next 3 weeks, or so. And then what? This will be another fine fix little Scotty has gotten ole Dad into.

Still time to block the email address or her acct on SD4M, before you end up taking the plunge. Think, use the BIG head sir. But, it sure would be fun to dive into, no doubt.

All the best to you on your decision, Vroom.[/QUOTE][QUOTE=F Scott; 1375567]I contacted her and arranged a "meeting" in the city on the steps of the Art Institute. I told her that we could take a look around inside if she wanted, or go to a nearby Starbucks and talk. The weather here has been unseasonably warm, so I did not feel bad about asking her to stand outside to wait for me. The plan was to drive by until I saw that she was there, then take off and text later saying something had come up. My thinking here was to see if she still looked as hot in person as she did years ago, and maybe get a little thrill out of it in the bargain.

All went off as planned, and I got a visual confirmation that the hotness quotient is still as high as ever, contacted her later with my "excuse", and that was that. [B]except[/B]: I now feel really guilty that I jerked her chain and made her waste time waiting for me when I knew full well that I wasn't going to show up just to add to my personal fantasy script.

[QUOTE]

[QUOTE=F Scott; 1376019]Castle,

I have a new car since the time she worked for me, so I wasn't worried about that. Pushing my luck is probably more the speed of things. I may put a gift card in an envelope with her name written on it and put it under the door where she works some evening after they're closed. I will write with my left hand, of course, so she can't recognize my writing, then send her a final email saying goodbye.

It's all fun and games until someone gets an eye poked out, and that could be me.

Go Patriots!

Scott[/QUOTE]Have you considered the "Criss-Cross" maneuver? Set up your drive by but select a wingman to follow you in his car. He doesn't have to know your real identity either. You signal him when you spot the girl. He then stops, jumps out, says he's you, takes her to the fucking chamber and fucks her for you. Require him to report back. Maybe take some more pictures. Then he owes you one and the girl gets her much needed semen deposit. You've done good deeds all around.

Scotty, As one horndog to the next.just fuck her for God's sake! I am sorry to hear your HCB has drifted away.I know how traumatic it is. These youngsters are pixie-like and here today gone tomorrow. Have you given her the ultimatum talk yet? It is good for closure if nothing else.

Several divorced older friends (my age) have opined on the different age groups that they have dated while looking for THE ONE. I will paraphrase best I can. And these categories apply mostly to college and professionally trained girls.not desperadas.

AGE : 18-26 interested in partying, staying out late, sleeping half the day away, hanging with their friends, getting drunk / high, multifucking for the sport of it.

26-30 settling down, still like going out, less wild, looking for a stable relationship, partying less intense.most desirable age range for an old dog *

31-36 calmer and settling down, hearing the tick tock of the biologic clock, often divorced already, young kids in the picture, an ex in the picture, a little desperate, ready to jump for a likely candidate

37 to 45 Good sport, all divorced, older kids in the picture, body still pretty well preserved, schedule difficult because of the kids and a difficult ex (all divorced men are bastards and all women are bitches)

46 to 55 All divorced, usually twice, kids grown and not as much issue, in touch with her freedom, but body is failing them

56 plus fugeddaboutit!

[QUOTE=F Scott; 1376019]It's all fun and games until someone gets an eye poked out, and that could be me.

Scott[/QUOTE]My point precisely. Good to hear that her I'd'ing the car wasn't an issue, but there are only so many chambers is life's gun. Maybe with her, it's time to stop worrying whether the next one is the loaded one.

Good luck and good hunting.

PS: has anyone run into problems staying logged in? Went to post this and the site told me I wasn't logged in, even though I'd gotten the usual 'welcome' message after entering my username / password. Not the first time either, so I was wondering if anyone else has been getting hit by this gremlin, or if it's just a problem with my account.

In my area these seem to be few and far between, but I did begin communications with one recently. She insisted in talking about the sugar immediately, which in my experience is never a good sign. She wouldn't even meet until she made the determination that "it would be worth her time" so I knew the odds were long on this one and I was correct. Once I told her my usual sugar amount, she told me it was good we didn't meet and waste both our times.

On the other hand, I do have a meet and greet set up with a HYB who insisted on meeting first. Obviously I'm going into it hopeful and with an open mind so wish me luck!

I've gotten a few other nibbles lately and will post of my successes and (failures).

Gentlemen,

I truly appreciate all your helpful thoughts, observations and warnings. They have caused me to do a lot of thinking, and I have come to the conclusion that I [I]am[/I] in fact, becoming addicted to dangerous behavior.

Recent events, i.e. the baby walking in on me having dinner with the family, this obsession I have with my former employee, and hitting on the Trader Joe's artist when in all likelihood she lives in my town, show a growing pattern that I feel I just can't ignore. It's almost like I'm trying to get caught, and that would not be good.

Compound this with the reality that my ATF is gone, and I feel I need to take a big step back and recalibrate what I consider to be "normal". Thus I have cancelled my SA profile, and will turn off my burner phone and hide it until I regain a healthy desire to avoid putting myself in risky situations. If I can't resist playing with fire right now, at least I can get rid of all the matches, right?

I will keep an eye on this thread, and still welcome any pm's from my brothers, but I probably will not have much to add, unless an earlier baby story becomes relevant. Thank you all for your help on this. I'm a little sad, but I know I did the right thing.

More than ever, keep up the good work, and don't forget to write!

Scott

[QUOTE=F Scott; 1376613]Gentlemen,

I truly appreciate all your helpful thoughts, observations and warnings. They have caused me to do a lot of thinking, and I have come to the conclusion that I [I]am[/I] In fact, becoming addicted to dangerous behavior.

Recent events, I. E. The baby walking in on me having dinner with the family, this obsession I have with my former employee, and hitting on the Trader Joe's artist when in all likelihood she lives in my town, show a growing pattern that I feel I just can't ignore. It's almost like I'm trying to get caught, and that would not be good.

Compound this with the reality that my ATF is gone, and I feel I need to take a big step back and recalibrate what I consider to be "normal". Thus I have cancelled my SA profile, and will turn off my burner phone and hide it until I regain a healthy desire to avoid putting myself in risky situations. If I can't resist playing with fire right now, at least I can get rid of all the matches, right?

I will keep an eye on this thread, and still welcome any pm's from my brothers, but I probably will not have much to add, unless an earlier baby story becomes relevant. Thank you all for your help on this. I'm a little sad, but I know I did the right thing.

More than ever, keep up the good work, and don't forget to write!

Scott[/QUOTE]I think this is an excellent idea and it proves that, even though you are physically attracted to other women, you are not going to play Russian Roulette with your families life! I must admit that I was getting concerned about how close things were getting to a potentially catastrophic event/confrontation. There will always be more opportunities once you regain your composure and control over your emotions and desires. I support you 100% and I have no doubt this is the right course for you!

LL

[QUOTE=LuckyLou; 1376623]There will always be more opportunities once you regain your composure and control over your emotions and desires.

LL[/QUOTE]Thanks Lucky

[QUOTE=F Scott;1376629]Thanks Lucky[/QUOTE]Scott, Your decision is understandable and maybe even wise.

Whatever you do next, you have already added immeasurably to the value of this thread. I hope you keep up the contributions.

For me, sb mongering is my way of rebelling against the unnatural restrictions of Sex Prison. I wish it weren't necessary to keep the activity secret. Men and women have different attitudes towards sex and we ought to be advanced enough to acknowledge it and work out live and let live rules for relationships between the sexes. As it now stands, the penalties for law abiding, established men of getting caught mongering are enormous and, in my view, unfair and unrealistic.

Maybe just chill your jets for a while.

Anyway, good luck.

F Scott:

It appears that you are taking a healthy step for you, at this time.

Best to be proactive when things go beyond the boundaries, and it seems that you are in that process.

Hopefully you can return in moderation. You and your reports will be missed in your absense.

All the best to you in the mean time brother.

Vroom