"Sugarbabies" / "Arrangements" Amateurs or Not?

**Spitfire** · 05-16-13 07:46

Originally Posted by F Scott [View Original Post]

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.

Scott, no offense, but I will say this bluntly to be sure it sinks in: Don't be stupid!

**PartyTimeGuy** · 05-16-13 07:31

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.

**PartyTimeGuy** · 05-16-13 07:09

Originally Posted by John G Smith [View Original Post]

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.

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!

**John G Smith** · 05-15-13 23:11

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.

**Joesouncool** · 05-15-13 22:08

Originally Posted by F Scott [View Original Post]

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

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?

**Flirting Guy** · 05-15-13 20:26

Originally Posted by HollywoodGuy [View Original Post]

Why risk it? There are too many fish in the sea. Seriously, forget about it.

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.

**HollywoodGuy** · 05-15-13 19:12

Originally Posted by F Scott [View Original Post]

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

Why risk it? There are too many fish in the sea. Seriously, forget about it.

**F Scott** · 05-15-13 18:57

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

**PartyTimeGuy** · 05-15-13 18:09

Originally Posted by Llhacara [View Original Post]

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

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.

**Llhacara** · 05-15-13 11:49

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

**FredMoore** · 05-15-13 10:24

Originally Posted by HollywoodGuy [View Original Post]

I don't know your age. But as far as I can tell at 59 I am attracting more girls than ever. And its not the dollars, because I got less of them than before. Way less. Confidence is a huge factor. I lost 20 lbs, started working out and got a better haircut. It works

HW, I am 60, look 48 to 52 according to females, tall, slim and muscular, attractive, personality very good in a one on one, educated, blah, blah, blah.

Negatives :

Separated but still hiding from public disclosure.

60 (to a 20 yr old 60 might as well be 80)

No picture on SA, fake pic on SDFM.

Very picky.

Budget limited by separation scrutiny.

Probably uninspiring profile.

**Flirting Guy** · 05-15-13 09:47

I have a cute 18yo that I am done with from SA. PM for details and line up for an exchange.

**Flirting Guy** · 05-15-13 09:19

Originally Posted by PartyTimeGuy [View Original Post]

Your experience parallels mine. It's funny how that in life the harder you work the luckier you get.

This is exactly what we do in sales. We're just converting leads into sales and then you have to keep the customer happy with ongoing support. More leads = more sales. I've hit the 400 mark for ladies I've contacted at SA in the last 2. 5 weeks since I've joined.

**PartyTimeGuy** · 05-15-13 08:15

Originally Posted by HollywoodGuy [View Original Post]

I don't know your age. But as far as I can tell at 59 I am attracting more girls than ever. And its not the dollars, because I got less of them than before. Way less. Confidence is a huge factor. I lost 20 lbs, started working out and got a better haircut. It works

Both are important but I couldn't agree with you more that personality trumps looks with most females. I am in my 40s and average looking. No 6 pack. Have love handles. It is my confidence and charm that is the most attractive bait as far as I can tell. Not that losing some weight, dressing sharper and getting a new haircut wouldn't help. Maybe even a better cologne. I have no SO to be suspicious about such improvements.

**PartyTimeGuy** · 05-15-13 08:06

Originally Posted by HollywoodGuy [View Original Post]

I just checked my stats on SD4me and I messaged 592 girls in the last 6 months. I got one new regular for my efforts. That works out to about 3 messages a day. And damn is she worth it. And I did do maybe 20+ face to face interviews. Rejection doesn't mean shit. Every no just puts you one step closer to a yes.

Your experience parallels mine. It's funny how that in life the harder you work the luckier you get.