"Sugarbabies" / "Arrangements" Amateurs or Not?

[GeorgeRichmond]

Don't know if anyone posted this. Interesting video.

http://www.cnn.com/video/data/2.0/vi...html?hpt=hp_c3

[JZLizard]

Well I'm knocking on wood right now and state this humbly, but I had a full on mistress for four years, in the same town, who lived eight miles away from me and my then SO. Neither knew of the other and never found out. I also had two affairs that were 3-4 months long each and did not get caught with the first, but got ball busted on the second and that ultimately cost me my marriage. My point is, it can be done, but in looking back on it, it was NOT worth it. I lived in constant anxiety and probably aged myself at double the normal rate. The stress was so enormous, some days I wanted to get caught so I could just get it out in the open and end it. I lived a total double life and went to lengths to cover my tracks any CIA agent would envy. It was pure insanity and the mistress was NOT worth it. I spent two years taking care of her, thinking this would keep her content and from digging deeper into my life. I lied, made up stories, covered tracks all day and night long, all while wishing it would end. It was not worth after the initial 6 months of fun we had.

Yeah I should clarify -- it can take many years before karma comes around, so it is possible to maintain affairs for extended periods of time without getting caught directly. I was married for a decade and for a period of several years, I was going out to clubs banging a never-ending stream of side pussy, on the order of 4-5 nights a week (this was in the days before Internet dating took off and bars and clubs were all people had for this sort of thing). While the SO knew I was going out, she never once had direct proof of me cheating -- I was too careful for that. But it still ultimately took it's toll and all of it came back to haunt me years after I stopped doing it, the marriage still ended for reasons that were far more vague than infidelity, but make no mistake my years of playing around were the direct cause. This is what I meant by the odds are stacked against "successfully" maintaining an SB and a wife in this day and age. As your story points out, even when you get lucky and get away with it once and break clean from the mistress, it only fuels you to do it again with a new mistress, it's almost impossible to stop until you get caught (and do it long enough and you will). This is what I meant by it's not a matter of IF you will get caught its a matter of WHEN. Even when you think you're successful, the marriage is taking collateral damage (and as you pointed out, so will the cheating husband simply due to the stress involved). As you pointed out, the stress of lying seems to literally shorten your life before your eyes, it's just not worth it.

I do however think that some occasional hit-and-run play can be successfully pulled off -- the key is to not get too involved with the girl. It still comes with risks. At the end of my last SB season, I met a girl who rocked my world so badly that when my GF returned from travel, it took me a full month of going dark and avoiding contact from all SBs to clear my head and fully remind myself why I was in my relationship with my SO in the first place.

I had no discipline when I was younger and sexual addiction controlled me. Now I'm older, wiser, and stronger -- I turned it around and I now control it.

[Dandy Don]

Ok, my SO was out of town for a full week so I am thinking to myself, this is going to be a fun week. My SB which I have sort of mix feelings on (nice girl, good and adventurous sex, youthful, but not my body type and so-so chemistry, and she is more business than I would prefer). So, I have a whole week, thinking a lot of action. We set something for Sunday, which wasn't the best day for me but I went along. Backs out. Nothing for Monday. Then says coming Tues. Then backs out. I am little pissed because I would have tried a to set something up with a FWBs that I have hooked up in the past.

Long story short, went the whole week, no SB, whiffed on last second FWB action, and settled for a couple of sensual massages that were nice but overpriced.

So I earnestly start looking for a new SB, not making much progress. Then I connect with an 18 year old who I had seen on SA but didn't contact before because she is about 40 miles away. But she is cute and about 97% my type, so I contact her. Hit it off very well, she brought up the topic of sex first, although it wasn't discussed in any detail, but put me at ease to know she knows the end game of this. We continue to text, she volunteers some sexy pics which were very nice. She seems TGTBT, quite frankly. Her name that was given to me is a common name, so at first I assumed it was fake and at first I didn't find any social media presence, which made me skeptical. I identified someone that I thought might be her, that matched the 18 year old age but still no pic to cross-reference. Eventually, I did find her FB page and she is indeed a very real girl.

Here is my worry, I won't be able to meet for about 3 weeks due to family, vacation, Summertime and kids not in school. Just simply no alone time. And she has joined like every SD site / dating site imaginable. So my fear is, she is going to find a regular before I can even make the magic happen. I did do a daring thing and wire her a small amount of cash. I figure this was in lieu of a M&G, I have had a lot of fun talking to her, and she has really been very open about herself. She seemed genuinely thankful, so I hope this buys me some traction and she won't discard me even she has other callers.

Anyway, to tie this into other discussions. First, some SBs act like pros (like my original) while this current one, I get much more of a "let's have a date" vibe, no mention of money or expectations. She seems to know there will be a payoff. Secondly, as for as longterm or one-timers, well I think it just depends on the girl. My original SB wants something steady, but doesn't really want a relationship. If I am going to see you over and over again, I actually want more than just sex. The new pot seems perfectly cool with anything. She understands the distance and availability issues and my gut tells me and she seems fine with having one very long date and making that as fun as possible for both of us. I prefer the second scenario. Because if I really do enjoy it, I will pay more and seek it out again. I guess what I am saying it's quality vs quantity. And it works both ways.

[DirtyDeeds38]

Yes, I understand and I agree completely. What I look for are "true SB"s (in terms of what type of girl they are), but I am not in a position to offer to be a true ongoing SD to them. My SB season is something like maybe one month out of the year, so I prefer to get as much variety as I can during that time frame.

Is it fair-play? Sure, I think so. One-night stands are a fact of life in any sort of dating situation. A girl might take you home with her and tell you you're the cats meow and then not return your phone calls the next day. I'm actually much more straight-forward than that with the girls and I don't over-promise anything. I tell them that there are no guarantees how often I will even travel to their town or area, and for that reason I'm not looking for a pre-arranged monthly arrangement. The downside to all of this is every now and then you meet an SB you'd really like to see regularly, and sometimes you want to be with them instead of going back to reality and life with the SO. So far I haven't hurt anyone's feelings that I'm aware of -- after a night of drinking and sex they haven't exactly gotten attached to me so for them when I tell them that's the last date they take it stride. I doubt most women that sport-fuck or serial-date have a straight-forward and honest approach to what they do.

If I didn't have a serious GF I would probably have one or two ongoing arrangements, but that was kind of my point to the poster asking about juggling an ongoing SB and a wife. I think it's EXTREMELY risky, and even though I'm as slippery as Ed Snowden when it comes to covering my tracks, I know women, and I know that if you have a wife or live-in, and try to maintain an ongoing fling of any sort, it's only a matter of time before karma comes around. So, doing the one-night stand thing is my only hope of dabbling in the bowl on occasion and keeping my relationship in tact.

Well I'm knocking on wood right now and state this humbly, but I had a full on mistress for four years, in the same town, who lived eight miles away from me and my then SO. Neither knew of the other and never found out. I also had two affairs that were 3-4 months long each and did not get caught with the first, but got ball busted on the second and that ultimately cost me my marriage. My point is, it can be done, but in looking back on it, it was NOT worth it. I lived in constant anxiety and probably aged myself at double the normal rate. The stress was so enormous, some days I wanted to get caught so I could just get it out in the open and end it. I lived a total double life and went to lengths to cover my tracks any CIA agent would envy. It was pure insanity and the mistress was NOT worth it. I spent two years taking care of her, thinking this would keep her content and from digging deeper into my life. I lied, made up stories, covered tracks all day and night long, all while wishing it would end. It was not worth after the initial 6 months of fun we had.

I say this for those thinking a true long term relationship with a SB is on your agenda with a SO. You will periodically meet a loving, sweet SB and begin having feelings. Those feelings will tempt you in and make you lose touch with reality and next thing you know, you're in a fucking unbelievable mess you wish never happened. Think with you big head brothers, this game will bite you hard if you do not!

[FredMoore]

The answer to Sugaring successfully long term is never get an SO. Period. For you single guys out there stay single. EVERY relationship long term gets stale. It is written in stone and inevitable. Men are born to be wild and spread seed far and wide. My SO did not buy that biology truism unfortunately. Do not try that one at home. The fear we old guys can have, is that we will die old and alone once the money runs out. So a loyal SO is a foil against loniless when sex is no longer on our mind (dead?).

Women are so easily accessible because of the internet. As long as you have enough money you can and will get in the game. Young women now view sex so casually. To them it is a pleasant exercise. As long as a guy is a little proficient in orgasm induction, they want their nutt just like we do.

[JZLizard]

To be honest, then that's not really a true SB / SD relationship or arrangement. You're basically setting up just one-night stands.

Yes, I understand and I agree completely. What I look for are "true SB"s (in terms of what type of girl they are), but I am not in a position to offer to be a true ongoing SD to them. My SB season is something like maybe one month out of the year, so I prefer to get as much variety as I can during that time frame.

Is it fair-play? Sure, I think so. One-night stands are a fact of life in any sort of dating situation. A girl might take you home with her and tell you you're the cats meow and then not return your phone calls the next day. I'm actually much more straight-forward than that with the girls and I don't over-promise anything. I tell them that there are no guarantees how often I will even travel to their town or area, and for that reason I'm not looking for a pre-arranged monthly arrangement. The downside to all of this is every now and then you meet an SB you'd really like to see regularly, and sometimes you want to be with them instead of going back to reality and life with the SO. So far I haven't hurt anyone's feelings that I'm aware of -- after a night of drinking and sex they haven't exactly gotten attached to me so for them when I tell them that's the last date they take it stride. I doubt most women that sport-fuck or serial-date have a straight-forward and honest approach to what they do.

If I didn't have a serious GF I would probably have one or two ongoing arrangements, but that was kind of my point to the poster asking about juggling an ongoing SB and a wife. I think it's EXTREMELY risky, and even though I'm as slippery as Ed Snowden when it comes to covering my tracks, I know women, and I know that if you have a wife or live-in, and try to maintain an ongoing fling of any sort, it's only a matter of time before karma comes around. So, doing the one-night stand thing is my only hope of dabbling in the bowl on occasion and keeping my relationship in tact.

[Latex]

The worst thing you can do is be in denial that you are the one guy on the planet that can get away with this without the wife knowing something is up. Women have a radar for this kind of thing that is incredible and outside the scope of male thought patterns -- their minds are just wired differently. We cannot even begin to fathom their detection mechanisms. Just like it seems that men are genetically designed to drive a car with skill most women will never understand, women are genetically designed to monitor their husband's marital fidelity in ways most men will never even be able to relate to. Even if she does not have direct proof, she will know something is up and there will be consequences of that to contend with. Do it long enough and she will have proof, and the consequences may get worse.

Basically be like Heisenberg.

And tracks are very difficult to cover these days, does your phone sync to the cloud? And sync back to the ipad in your family room?

Does yahoo or google decide to keep you logged in? Does your GPS remember where you have been?

Does your bank send alert when balance changes? Your SO asks if that was a different ring tone, she heard in your pocket?

Do you have condoms in your pocket? Did you wife's friend see you picking something for SB at the store? Did you lie and say you were with a friend and did not collaborate earlier? Do you have Life 360 installed on your phone? How do you pay for a burner phone?

If you are married you are basically screwed, your SO will find out one day.

It is impossible to cover everything, maybe that's part of the thrill.

[Va Ga]

To be honest, then that's not really a true SB / SD relationship or arrangement. You're basically setting up just one-night stands.

Yes, setting up the initial date takes a lot of time and effort. But the real challenge is juggling a SB / Mistress / Girlfriend for any length of time. It's usually the on-going contact and multitude of dates / FC romps that eventually get most guys caught. After all that's what separates from just seeing a bunch of random escorts.

In fact for me at least, if there's no potential or desire whatsoever to see a SB a second time, then I usually don't go through all the effort just to see her once. With a real SB, quite a bit of groundwork has to be laid between email / text exchanges, aligning schedules, gaining her confidence, measuring her expectations and etc, that I like to see a SB at least 2-3 times to feel like I actually broke even in terms of time and effort. Most of my one and done's tend to be because there was a lack of chemistry or she was out of my league.

Cultivating on-going arrangements / relationships is IMO one of the fun parts of the Sugar Bowl, which separates it from the Escort hobbies. It always puts a smile on my face receiving flirty texts from hot young 20 year-old girls or when they text me out of the blue wanting to meet up. I'm at the point now where I don't have to do any fishing, where the fish will come to me. I actually just recently did a test, I didn't do any CL ads, no SD sites, nor did I initiate any contact. And I wanted to see how long it would take for a girl to contact me. Within a day, one girl contacted me wanting to me, and then the next day another. By the end of the week, I had 3 dates setup from me not even lifting a finger. I was just living off the residuals of the groundwork I put in over the last couple of years. And these residuals were hotter than 95% of the girls on backpage and the sex romps magnitudes better.

Of course the challenge is juggling on-going SBs and BCs (Booty Calls). JeezLizard made a good point, that's not a matter of IF, it's WHEN. You will get caught or slip up in some way at some point. The odds are never in your favor and honestly you shouldn't fully play in the Sugar Bowl if exposure would destroy your world. And even if it wouldn't, you should always have multiple bomb shelters at the ready regardless.

I could give a laundry list of do's and do not do's for juggling a SB and SO. But I recommend just searching online for things like "How to cheat on your wife" or "How to maintain a mistress". There's good advice out there but some things you may do differently depending on your situation.

I will say, start off small. I know it's extremely tempting, but don't try to meet 4-5 pots and SBs right off the bat. If you haven't learned how to cover your tracks, your sugar career will have ended before it even started trying to juggle that many. So have a small list of pots and narrow it down to one or two legit SBs and focus on just meeting that person while you get the hang of concealing your sugar activities. There isn't a one-size fits all, so you may have to do some things slightly different than others here.

I ended up doing this over seas. Most if not all of what is said is true. Laying the ground work takes time and patience. I also agree that it is not about IF but when you slip. I have been fortunate enough to get to those bomb shelters but it is not something you wish for. It can also be quite addictive. I had at most 6 on rotation. I wised up and have cut that to 2 and some booty calls (all this based over seas). I am trying to figure out the lay of the land right now before building a line-up and tech makes thins more complicated for me at least. I am think that Cali might be more of my scene but I have only just got back into Richmond so it is too soon to tell.

[John G Smith]

3. I only see an SB once, then I break it off. Don't let attachment develop.

To be honest, then that's not really a true SB / SD relationship or arrangement. You're basically setting up just one-night stands.

Yes, setting up the initial date takes a lot of time and effort. But the real challenge is juggling a SB / Mistress / Girlfriend for any length of time. It's usually the on-going contact and multitude of dates / FC romps that eventually get most guys caught. After all that's what separates from just seeing a bunch of random escorts.

In fact for me at least, if there's no potential or desire whatsoever to see a SB a second time, then I usually don't go through all the effort just to see her once. With a real SB, quite a bit of groundwork has to be laid between email / text exchanges, aligning schedules, gaining her confidence, measuring her expectations and etc, that I like to see a SB at least 2-3 times to feel like I actually broke even in terms of time and effort. Most of my one and done's tend to be because there was a lack of chemistry or she was out of my league.

Cultivating on-going arrangements / relationships is IMO one of the fun parts of the Sugar Bowl, which separates it from the Escort hobbies. It always puts a smile on my face receiving flirty texts from hot young 20 year-old girls or when they text me out of the blue wanting to meet up. I'm at the point now where I don't have to do any fishing, where the fish will come to me. I actually just recently did a test, I didn't do any CL ads, no SD sites, nor did I initiate any contact. And I wanted to see how long it would take for a girl to contact me. Within a day, one girl contacted me wanting to me, and then the next day another. By the end of the week, I had 3 dates setup from me not even lifting a finger. I was just living off the residuals of the groundwork I put in over the last couple of years. And these residuals were hotter than 95% of the girls on backpage and the sex romps magnitudes better.

Of course the challenge is juggling on-going SBs and BCs (Booty Calls). JeezLizard made a good point, that's not a matter of IF, it's WHEN. You will get caught or slip up in some way at some point. The odds are never in your favor and honestly you shouldn't fully play in the Sugar Bowl if exposure would destroy your world. And even if it wouldn't, you should always have multiple bomb shelters at the ready regardless.

I could give a laundry list of do's and do not do's for juggling a SB and SO. But I recommend just searching online for things like "How to cheat on your wife" or "How to maintain a mistress". There's good advice out there but some things you may do differently depending on your situation.

I will say, start off small. I know it's extremely tempting, but don't try to meet 4-5 pots and SBs right off the bat. If you haven't learned how to cover your tracks, your sugar career will have ended before it even started trying to juggle that many. So have a small list of pots and narrow it down to one or two legit SBs and focus on just meeting that person while you get the hang of concealing your sugar activities. There isn't a one-size fits all, so you may have to do some things slightly different than others here.

[DirtyDeeds38]

Last night I met a heavier set 21 year old I had been txting with for a few days because she said she was super submissive and she had a pretty face. I picked her up and went straight to a room. She said she was a good girl and that she just wanted to make daddy happy. She said to just do anything I wanted to her. After about 30 minutes of heavy pounding she said she was tired so I face fucked her for almost an hour after that. I have rarely had a spinner go balls deep for more than a minute here and there. This girl just sucked and sucked, repeatedly DT-ing, gagging and drooling. Going all the way down most of the time.

So when it was time to leave I told her I needed to stop at the ATM to get her the $ I promised for our time together. She said she wasn't comfortable with that so we settled on half of that. After the ATM I handed her the cash and she said she didn't really want any money and that she just had a daddy fetish and gave me back the cash, except for 10 dollars. I'll probably see her again. I would say she was a 7/6/10/9. Even though she was big she was proportionately curvy with flawless tanned skin and a shaved kitty that was smooth as silk.

Since I still had the room I called my MILF as she lived nearby and I did another hour with her. So I got to double dip on the room. After working for 8 hours and then 6 more hours of dating I stopped for a burger and chocolate shake at my favorite drive through. Appropriately enough called "In and Out". Finally got home and passed out cold.

Hollywood, anyone ever told you here we envy you? JHC what I'd do for a day at the park like you had! With all due respect, and you deserve all there is to dish out around here, sometimes, some of us mongers here just hate you! Haha. But you didn't sit back, smile for a bit and have an ice cold beer before you passed out? I need a day like this and I need it soon!

[John G Smith]

That's the hard part.

So true. So true.

Some guys are lucky that their SO still look and perform decent in bed, so it's easier for them to keep up appearances. But for those of us with SO's who've let themselves go or have almost no sex drive, then it's a real challenge.

[Graham111]

Figure the less BB she is doing with others the less the likelihood of a "gift" from another SD.

Learning the ropes here. I get you had a big V so I guess you are trying to get her to trust you more?

[JZLizard]

What is the best way to juggle a SB and a wife? I need some helpful advice.

First and foremost, you MUST accept up front that odds are not in your favor. Having an ongoing SB is more like having a GF on the side, it comes with risks that wouldn't be there if you were just visiting massage parlors or escorts. You've got other risk factors like ongoing contact, potentially the SB's emotions flying out of hand, and other things that create a whole new dynamic. So, you have to treat having an SB as if it were any other type of mistress -- and we all know how those inevitably turn out. Do it long enough and getting caught is not a matter of IF, it's a matter of WHEN. You should have your strategy for dealing with the consequences already thought out and well-planned, whether that is financially planning for divorce, hiding money, or whatever you need to do.

The worst thing you can do is be in denial that you are the one guy on the planet that can get away with this without the wife knowing something is up. Women have a radar for this kind of thing that is incredible and outside the scope of male thought patterns -- their minds are just wired differently. We cannot even begin to fathom their detection mechanisms. Just like it seems that men are genetically designed to drive a car with skill most women will never understand, women are genetically designed to monitor their husband's marital fidelity in ways most men will never even be able to relate to. Even if she does not have direct proof, she will know something is up and there will be consequences of that to contend with. Do it long enough and she will have proof, and the consequences may get worse.

So, you have to accept all of this right up front. Any level of denial will only result in getting caught faster (because the denial prevents you from being as careful as you should be) and the consequences hitting harder (denial prevents us from preparing properly for when the shit hits the fan).

That being said, if you've weighed the risk / reward and decided it's still for you, do lots of research on how to cheat without getting caught (do not limit your understanding to dealing with SBs, because if you can learn to manage a full-on girlfriend on the side, you will actually be in a better position to manage most SB arrangements).

I can tell you my basic strategy, but it may not apply to your situation:

1. I only do it when my SO is out of town for extended periods of time.

2. I never contact a POT that lives within a 100 mile radius.

3. I only see an SB once, then I break it off. Don't let attachment develop.

4. Never reveal real name, or use primary phone for text / call.

5. I research each SB as early as possible and as much as possible, to understand all aspects of the risk that might be involved, and remain committed to not letting myself think with my dick.

I will talk a little bit about #5 here because its important. This is basically just about cutting loose any SB that could remotely come back to haunt you, and to know this you have to basically be like a detective / research scientist to find out things about the girl. For example, once I found a HCB that was perfect SB material -- but in talking to her, I found out that she had family that she stays with when she's not in school that was inside my danger zone radius. Think about what that means? It means that after college if she doesn't get a job right away, she might move in with her family and live / work near me. My dick and balls was saying "ah don't be paranoid, tap that sweet pussy", but my brain was saying "how will you feel if the SB situation goes south and you run into this girl at a restaurant with your SO a year later?

In the above example, the brain might seem overly paranoid, but the thing is I was married for a long time and have a high number of "been there done that" stories to tell. It's a small world. Your best bet is if you're a traveling type and can keep all your SBs very far away physically.

[Golfcart]

. . . don't let the SB change the way you do things-the wife will notice and wonder.

That's the hard part.

[Craps7]

I have had no SB insist after the second date (if they made it that far) but I have a vasectomy so no risk. I prefer the SB is not on birth control as if she is I assume she is BB for every Tom, Dick and Harry. But maybe I am just nave. But for the third hole I always use one. That could get me busted at home!

Learning the ropes here. I get you had a big V so I guess you are trying to get her to trust you more?