"Sugarbabies" / "Arrangements" Amateurs or Not?

[QUOTE=Llhacara; 1763138]Recently I decided to check out the SD websites to see how it was, and so far I am enjoying it. I've yet to meet an SB.

I received some interest from the ladies, some I was interested in others not so much. I responded back to a few who sent me.

A message and I responded back letting them know that the interest was mutual. I included my contact number and suggested.

That we could chat via texting or phone. I want to know was it to quick and early to send my contact info or should I have sent.

Messages back and forth first?

Newbie here[/QUOTE]Despite having had more than 100 SBs I am a relatively new poster to this site. However, I will have to say that the contributors here offer some very wise and helpful advice on the subject of SBs. A compilation of the advice in this thread would make quite a useful publication for all SDs.

Gentlemen,

Well, given the law of averages, it had to happen sooner or later. I was browsing the recent babies in New Orleans on SA this morning in anticipation of a possible trip at the end of the month to visit my youngest daughter, and I ran across a profile of one of my older daughter's college roommates! Now this is a girl I have had a huge and entirely inappropriate thing for since I first met her almost 6 years ago when visiting my daughter at college for parent's weekend. I mean it was chemical, at least for me, to the point that I had to put a little distance between us if we hugged so she wouldn't feel Scottie at full attention. I spent many a happy afternoon fantasizing about fucking her, and I have to be honest in saying that this latest discovery does not help matters at all.

I know the answer to this in my rational brain, but what would you all do? She will see, if she looks at who viewed her profile, that I looked at hers, but I have no public pictures, thank you baby Jesus, and my details are off just enough that she probably won't put two and two together, but I am feeling a very pleasant buzz of adrenaline running through my veins, and wonder what I would do if she contacted me, thinking I was just some horny dude from Chicago.

Has anyone ever successfully navigated these treacherous shoals? How did it turn out? Anyone who is in NOLA or goes there, I might share the profile, but you have to promise to take pics and videos! She is not a "classic" beauty, think more of an ethereal beauty in a painting by Vermeer, but I have always found her irresistable, no more so than now, unfortunately.

On the side of rationality, there's no guarantee that if I did contact her and reveal myself, that she would be anything other than repelled at the thought of fucking her best friend's father, but oh, my brothers, how often have I imagined that wondrous day when I would be settled between her thighs, looking down on her as she pulled me close!

In other news, I am balls deep in babies at home, but a wondrous one, who I thought had moved on, has recently come on strong, and honestly has driven all thoughts, (with the exception of the above) out of my head. She is funny, smart as can be, quick-witted, sassy, naturally beautiful, and for some strange reason seems to be totally into me! Our time together so far has been effortless, and we are scheduled for some "quality time" on Monday, at her instigation. At our lunch date today, she insisted on paying! And she is a gorgeous 27 yo who had our waiter drooling shamefully. What a wonderful world we live in, no? So far we have only kissed discretely, but I think she is still getting used to the whole idea. She is an intoxicating mix of sexy and virginal.

I await your advice on the NOLA roommate.

Scott

[QUOTE=F Scott; 1763515]Gentlemen,

Well, given the law of averages, it had to happen sooner or later. I was browsing the recent babies in New Orleans on SA this morning in anticipation of a possible trip at the end of the month to visit my youngest daughter, and I ran across a profile of one of my older daughter's college roommates! Now this is a girl I have had a huge and entirely inappropriate thing for since I first met her almost 6 years ago when visiting my daughter at college for parent's weekend. I mean it was chemical, at least for me, to the point that I had to put a little distance between us if we hugged so she wouldn't feel Scottie at full attention. I spent many a happy afternoon fantasizing about fucking her, and I have to be honest in saying that this latest discovery does not help matters at all.

I know the answer to this in my rational brain, but what would you all do? She will see, if she looks at who viewed her profile, that I looked at hers, but I have no public pictures, thank you baby Jesus, and my details are off just enough that she probably won't put two and two together, but I am feeling a very pleasant buzz of adrenaline running through my veins, and wonder what I would do if she contacted me, thinking I was just some horny dude from Chicago.

Has anyone ever successfully navigated these treacherous shoals? How did it turn out? Anyone who is in NOLA or goes there, I might share the profile, but you have to promise to take pics and videos! She is not a "classic" beauty, think more of an ethereal beauty in a painting by Vermeer, but I have always found her irresistable, no more so than now, unfortunately.

On the side of rationality, there's no guarantee that if I did contact her and reveal myself, that she would be anything other than repelled at the thought of fucking her best friend's father, but oh, my brothers, how often have I imagined that wondrous day when I would be settled between her thighs, looking down on her as she pulled me close!

In other news, I am balls deep in babies at home, but a wondrous one, who I thought had moved on, has recently come on strong, and honestly has driven all thoughts, (with the exception of the above) out of my head. She is funny, smart as can be, quick-witted, sassy, naturally beautiful, and for some strange reason seems to be totally into me! Our time together so far has been effortless, and we are scheduled for some "quality time" on Monday, at her instigation. At our lunch date today, she insisted on paying! And she is a gorgeous 27 yo who had our waiter drooling shamefully. What a wonderful world we live in, no? So far we have only kissed discretely, but I think she is still getting used to the whole idea. She is an intoxicating mix of sexy and virginal.

I await your advice on the NOLA roommate.

Scott[/QUOTE]Why risk it? There are too many fish in the sea. Seriously, forget about it.

[QUOTE=HollywoodGuy;1763527]Why risk it? There are too many fish in the sea. Seriously, forget about it.[/QUOTE]I think you don't out yourself via SA but casually hit on her IRL and test the waters. If she responds take it from there. But use SA to dialog with her and find out her limits. Don't use your real pic of course.

[QUOTE=F Scott; 1763515]Gentlemen,

Well, given the law of averages, it had to happen sooner or later. I was browsing the recent babies in New Orleans on SA this morning in anticipation of a possible trip at the end of the month to visit my youngest daughter, and I ran across a profile of one of my older daughter's college roommates! Now this is a girl I have had a huge and entirely inappropriate thing for since I first met her almost 6 years ago when visiting my daughter at college for parent's weekend. I mean it was chemical, at least for me, to the point that I had to put a little distance between us if we hugged so she wouldn't feel Scottie at full attention. I spent many a happy afternoon fantasizing about fucking her, and I have to be honest in saying that this latest discovery does not help matters at all.

I know the answer to this in my rational brain, but what would you all do? She will see, if she looks at who viewed her profile, that I looked at hers, but I have no public pictures, thank you baby Jesus, and my details are off just enough that she probably won't put two and two together, but I am feeling a very pleasant buzz of adrenaline running through my veins, and wonder what I would do if she contacted me, thinking I was just some horny dude from Chicago.

Has anyone ever successfully navigated these treacherous shoals? How did it turn out? Anyone who is in NOLA or goes there, I might share the profile, but you have to promise to take pics and videos! She is not a "classic" beauty, think more of an ethereal beauty in a painting by Vermeer, but I have always found her irresistable, no more so than now, unfortunately.

On the side of rationality, there's no guarantee that if I did contact her and reveal myself, that she would be anything other than repelled at the thought of fucking her best friend's father, but oh, my brothers, how often have I imagined that wondrous day when I would be settled between her thighs, looking down on her as she pulled me close!

In other news, I am balls deep in babies at home, but a wondrous one, who I thought had moved on, has recently come on strong, and honestly has driven all thoughts, (with the exception of the above) out of my head. She is funny, smart as can be, quick-witted, sassy, naturally beautiful, and for some strange reason seems to be totally into me! Our time together so far has been effortless, and we are scheduled for some "quality time" on Monday, at her instigation. At our lunch date today, she insisted on paying! And she is a gorgeous 27 yo who had our waiter drooling shamefully. What a wonderful world we live in, no? So far we have only kissed discretely, but I think she is still getting used to the whole idea. She is an intoxicating mix of sexy and virginal.

I await your advice on the NOLA roommate.

Scott[/QUOTE]My suggestion is to stay away from your daughter's former roommate. There are plenty of chicks out in the world. Why create any possible friction. Can a 27 year old be trusted to keep her mouth shut? My fuck buddy introduces me as her boyfriend to her family and the people she works with at her strip club. I've asked her specifically not to do this, but no luck. Can a 27 year old be trusted?

Sometimes I entertain risks like that because "Hey, you only live once!". But I'd let this go. If you were getting divorced or separated in the very near future, then maybe go for it. But if you plan to still preserve your marriage, then banging your daughter's roommate is a no-no. You would have no "deep cover" and you would be completely exposed and have no leverage on her to keep her mouth shut. Now IF she was married, then you might have enough leverage to keep her discrete. Short of that, she would have you by the balls on day one. In fact, simply contacting her (and she rejects you) , she would have you by the balls.

Instead just find a SB who looks just like this roommate and live out your fantasies that way.

[QUOTE=John G Smith; 1763753]Sometimes I entertain risks like that because "Hey, you only live once!". But I'd let this go. If you were getting divorced or separated in the very near future, then maybe go for it. But if you plan to still preserve your marriage, then banging your daughter's roommate is a no-no. You would have no "deep cover" and you would be completely exposed and have no leverage on her to keep her mouth shut. Now IF she was married, then you might have enough leverage to keep her discrete. Short of that, she would have you by the balls on day one. In fact, simply contacting her (and she rejects you) , she would have you by the balls.

Instead just find a SB who looks just like this roommate and live out your fantasies that way.[/QUOTE]The upside? You get to live out a fantasy. The downsides? Potential to poison every important relationship in your life AND MAYBE WORSE! Let's suppose this girl even keeps her mouth shut about it while you are seeing her. And that is a big IF since we know that females love to blab about anything to anyone who will listen. She most certainly will talk about it after it is over, and, trust me, it will be over at some point. She is personally connected to you. It violates the very first rule of having a SB: to stay incognito as much as possible! This is just a time bomb waiting to go off. Dream about it, jerk off to the idea of it. But DON'T DO IT!

My horny married big-titted MILF. Not exactly a 10 by any stretch but good enough for regular stress relief. I used to throw her $ every now and then but now she just enjoys getting some on the side. She even pays for the hotel room, LOL. She loves to suck cock and ride cock and get called every manner of nasty name while she does it. Last time she sucked my dick for almost an hour while I called her a naughty fat **** and every other nasty thing I could think of. She loved it! Now she has a married gf she fools around with every now and then who wants to join us in a threesome. A nice change of pace and variety from my other regular SBs. Life IS good my brothers.

[QUOTE=F Scott; 1763515]Gentlemen,

I know the answer to this in my rational brain, but what would you all do? She will see, if she looks at who viewed her profile, that I looked at hers, but I have no public pictures, thank you baby Jesus, and my details are off just enough that she probably won't put two and two together, but I am feeling a very pleasant buzz of adrenaline running through my veins, and wonder what I would do if she contacted me, thinking I was just some horny dude from Chicago.[/QUOTE]Scott, no offense, but I will say this bluntly to be sure it sinks in: Don't be stupid!

[QUOTE=Flirting Guy;1763603]I think you don't out yourself via SA but casually hit on her IRL and test the waters. If she responds take it from there. But use SA to dialog with her and find out her limits. Don't use your real pic of course.[/QUOTE]I'd add if you're married and want to remain so then don't touch. I was suggesting under the premise that you are divorced and your daughter is ok w / you dating girls her age. Unlikely I guess. LOL

I thought I would provide an update on my progress in dipping into the bowl. This spring I was out of town for an extended period for work. I decided to try the Sugar world out for amusement while I was gone. I had minor success there, but was really to busy with work to devote much time to it. I had signed up for three months on SA, so it seemed like the only thing to do was to try and set up some potentials for when I returned home for the summer. I discovered that the attention span of many of these babies is not long. I thought that a month before I was back in town would be a reasonable period to email or chat and build a rapport, but that was way too long. Most of the girls I started out chatting up drifted off to other daddies or decided to give this up altogether. So, as time approached for me to get back home I started on a new wave. I am subscribing to the strength in numbers approach that HG and others have recommended. I have sent out about 60 opening salutations in the past couple of weeks. My response rate has been lower than I would like. I confess I didn't put a lot of effort into my profile when I signed up, so my next step is to overhaul it. I am also experimenting with different versions of my greeting letter. I have a private photo on SA that I allow access to when asked for a pic. It is not a very good one, taken myself, need to do something about that as well. I think I am also going to put together a simple spreadsheet to track my efforts and results (I've already found that it's hard to remember every SB's profile that I reached out to). Anyway, here are the results to date.

NavyBrat: 27 yo AA (7/5/9) She is a nursing student & single mom, had newly signed up on the recommendation of a friend of hers. I contacted her on her first day and she responded right away. We emailed back and forth a few times, then texted, and finally agreed to lunch the same day. Total time from first contact till panties on floor 6 hours. She had no clue as to what kind of arrangement she wanted. I ended up giving her $ when I dropped her off. She's a sweet girl with a pretty smile, but the body was post baby and a little heavier than I expected (I hate those deceptive pics!). She has already texted me about a repeat, but probably not a keeper.

Amazon: 21 yo redhead. 6' tall, voluptuous (8/7/7). I generally go for the tiny little spinners, so this is another one that's not right up my alley, but I am intrigued by the legs. We have a M&G set for this evening, and all indications are that we will go directly from drinks to BCD. She has been pretty up front that she is ready for that, and also has not mentioned dollars, other than to say that she likes presents from time to time. She is employed, lives at home, is close by. If things go well she may be in the rotation for a while.

MedStudent: 27 yo Latina (7/7/8) , very bright, was upfront about wanting a NSA relationship, too busy with school for much else. Thought she was locked in. Then got a text when I got home saying she had started to feel bad about having casual sex. Wasn't going to do it anymore.

Cali Blond: 23 yo white hardbody (8/9/6). Had a previous SD. Has agreed to a M&G. Probable serious case of GPS, but she is awfully hot. Not sure if I can get her in the budget, but hey, its worth a try.

I have 3-4 others that are in the exploratory stages, hope to firm something up this week. I appreciate all the great info on this thread, I think I have found the area of this sport that I need to be in.

[QUOTE=F Scott; 1763515]Gentlemen,

Well, given the law of averages, it had to happen sooner or later. I was browsing the recent babies in New Orleans on SA this morning in anticipation of a possible trip at the end of the month to visit my youngest daughter, and I ran across a profile of one of my older daughter's college roommates! Now this is a girl I have had a huge and entirely inappropriate thing for since I first met her almost 6 years ago when visiting my daughter at college for parent's weekend. I mean it was chemical, at least for me, to the point that I had to put a little distance between us if we hugged so she wouldn't feel Scottie at full attention. I spent many a happy afternoon fantasizing about fucking her, and I have to be honest in saying that this latest discovery does not help matters at all.

I await your advice on the NOLA roommate.

Scott[/QUOTE]The brothers have spoken. Suicide

My perspective is this. My daughter is the target age for most of us and she constantly harasses me about my "inappropriate attention I give her hot friends."

You would lose your daughter in a flash if this exploded.even forgetting the wife.

Gentlemen,

Well, there seems to be 100% consensus on the foolishness of contacting my daughter's ex-roommate, but I will keep thinking about her nonetheless, and it will be interesting to talk to her the next time she comes to town to visit, knowing in the back of my head that she is in The Bowl.

Thanks for the advice, even though it was not what I wanted to hear,

Scott

[QUOTE=F Scott; 1764156]Gentlemen,

Well, there seems to be 100% consensus on the foolishness of contacting my daughter's ex-roommate, but I will keep thinking about her nonetheless, and it will be interesting to talk to her the next time she comes to town to visit, knowing in the back of my head that she is in The Bowl.

Thanks for the advice, even though it was not what I wanted to hear,

Scott[/QUOTE]My 30 year old daughter who lives with me has to see a parade of girls (much younger than her) streaming through the house, no problem.

One of her guy friends once banged one of my x SB's, no problem.

What you are / were considering. Thats a problem.

Something about shitting where you eat? Whatever the quote is

I have read many a tale on this site of guys saying "OMG that was best sex, BBBJ, whatever". My question is, was it the best for her?

I will never put an SB on allowance unless I am convinced she needs my dick more than the money. Of course it is the total package. But if you can't control her with dick, hands and tongue no amount of money is going to keep her in line. I have learned this the hard way (so to speak) more than once.

Anything less than this will keep them on a pay per date arrangement.