"Sugarbabies" / "Arrangements" Amateurs or Not?

[LoriTruck]

I would have to ask you..."Does she have any of your personal information?" Your real name...cell number? Did you cover your tracks at all? Use a burner email? Phone? That's what I do...and connect to the internet for your hunting and connecting via a private anonymous VPN?

I would venture to say that you probably did not cover all of your bases and if push came to shove she could get the courts to subpoena IP information, cell records etc.

Tough position I would never want to be in..makes me regret the few times that I too went bareback with a SB.

I basically screwed my self on this one. She has my real name (first & last,) cell (not the bootleg # and the city & state that I call home. I pulled out each time but that didn't do any good. I have sent her countless pictures, texts, & had endless conversations when we first met. You know how when you first meet and get the digits? You send a face pic, chest pic, shower pic etc... She has everything she needs to tarnish my clean slate that I had going. 30 years old, steady job, no kids you name it. Now I'm at her mercy.

[JZLizard]

Sooooooooo I got a delicate situation at hand. 3 months ago a SB sends me a text saying she lost it. I'm thinking she lost her mind or lost her house. She goes around in circles and finally tells me she lost the baby. Hmmm? I had no idea she was pregnant and 3 months into the pregnancy for that matter. I'm saddened and relieved but still, why wait 3 months to inform me? Fast forward to now. She admits to lying about the miscarriage so now she is 7 months and every now and then, she sends a picture of the tummy. Well, (Gulp) let's see. She is pretty independent, she says she doesn't need me, she says she can handle this on her own and she lives 1500 miles away. Am I on a clear path to home plate or will there be problems up ahead? In other words, can she say she has no clue as to who the father is or how will all this play out?

Delicate situation indeed, the lying and the game playing so far would give me great concern. I would start slowly building a story of my own that would help to separate me from the situation. Some sort of job or health related tragedy that unfolds slowly over time but basically sends a message to her that you will probably be bankrupt or disabled going forward (I.e. Not a good extortion target).

How much does she know about you (real name, etc)?

[WoodSlinger]

Sooooooooo I got a delicate situation at hand. 3 months ago a SB sends me a text saying she lost it. I'm thinking she lost her mind or lost her house. She goes around in circles and finally tells me she lost the baby. Hmmm? I had no idea she was pregnant and 3 months into the pregnancy for that matter. I'm saddened and relieved but still, why wait 3 months to inform me? Fast forward to now. She admits to lying about the miscarriage so now she is 7 months and every now and then, she sends a picture of the tummy. Well, (Gulp) let's see. She is pretty independent, she says she doesn't need me, she says she can handle this on her own and she lives 1500 miles away. Am I on a clear path to home plate or will there be problems up ahead? In other words, can she say she has no clue as to who the father is or how will all this play out?

I would have to ask you..."Does she have any of your personal information?" Your real name...cell number? Did you cover your tracks at all? Use a burner email? Phone? That's what I do...and connect to the internet for your hunting and connecting via a private anonymous VPN?

I would venture to say that you probably did not cover all of your bases and if push came to shove she could get the courts to subpoena IP information, cell records etc.

Tough position I would never want to be in..makes me regret the few times that I too went bareback with a SB.

[LoriTruck]

Sooooooooo I got a delicate situation at hand. 3 months ago a SB sends me a text saying she lost it. I'm thinking she lost her mind or lost her house. She goes around in circles and finally tells me she lost the baby. Hmmm? I had no idea she was pregnant and 3 months into the pregnancy for that matter. I'm saddened and relieved but still, why wait 3 months to inform me? Fast forward to now. She admits to lying about the miscarriage so now she is 7 months and every now and then, she sends a picture of the tummy. Well, (Gulp) let's see. She is pretty independent, she says she doesn't need me, she says she can handle this on her own and she lives 1500 miles away. Am I on a clear path to home plate or will there be problems up ahead? In other words, can she say she has no clue as to who the father is or how will all this play out?

[Happy Lover]

The optimal circumstance for an SD is an out of town travel schedule. Playing at home is hard to do since it is hard to explain hours off the grid or sightings in public by friends of the "family" Once you are busted it becomes necessary to account for your movements if your SO calls / texts and expects an answer. That dreaded "where are / were you? " turns my blood cold.

Ashley Madison is well covered here, so check out the history JL. Briefly, I have had zero luck as have most of the brothers. You have to be younger and "date " worthy for a cougar. There are some young hotties but they are pickier due to the huge male / female discrepancy and motivation is less since they generally are not looking for money. There are exceptions like in everything. Some singles are SBs in disguise.

One of the things that I've had to do is set the expectation of communication in the wake of last years discovery. Ignore her call and get back to her a couple of hours later when you have an ironclad alibi (out with mutual friends, etc). Do this from time to time. Blame it on the ringer, cell service, ambient noise, whatever. It becomes more of the norm and lessons her anxiety when you don't pick up or get back to her right away. After a month or two, you'll feel comfortable enough for play time and she won't go ballistic when you don't pick up.

[ChiGuy606]

Many of us want to stay married for a variety of reasons, and have to work through barrels of well earned shit. This is my situation. I still dabble and keep an occasional FB but can no longer pursue a full on SB search. The antennae are up and suspicion is high and every move is monitored. What a life -eh?

This pretty much explains my situation right now exactly.

I have 2 leftovers from when I was fully in the bowl, and they are both wonderful women to be able to let me see them on a very occasional basis. Other than that, I can no longer afford the time to be fully invested in the bowl like I was last year.

Even if I never return, I will take with me memories that will last me my whole life. It truly was one hell of a ride while it lasted!

[FredMoore]

The optimal circumstance for an SD is an out of town travel schedule. Playing at home is hard to do since it is hard to explain hours off the grid or sightings in public by friends of the "family" Once you are busted it becomes necessary to account for your movements if your SO calls / texts and expects an answer. That dreaded "where are / were you? " turns my blood cold.

Ashley Madison is well covered here, so check out the history JL. Briefly, I have had zero luck as have most of the brothers. You have to be younger and "date " worthy for a cougar. There are some young hotties but they are pickier due to the huge male / female discrepancy and motivation is less since they generally are not looking for money. There are exceptions like in everything. Some singles are SBs in disguise.

[JZLizard]

I echo that sentiment. I do not know Scott's situation at all but I do know that the Sugar lifestyle is relatively short lived for a married SD. Eventually the sneaking around is discovered and unless divorce is an immediate result the SD is off the shelf struggling to repair the damage done. Many of us want to stay married for a variety of reasons, and have to work through barrels of well earned shit. This is my situation. I still dabble and keep an occasional FB but can no longer pursue a full on SB search. The antennae are up and suspicion is high and every move is monitored. What a life -eh?

So this is why I encourage guys dabbling in the bowl to be absolutely sure that they want to take that 1st step down a road that will inevitably end up in a world of hurt. Now the single guys have it made although some, like JL, have GFs who will bolt if any hint of sugar participation comes out.

So guys who have quit did so IMHO because 1) they were busted by the SO 2) they are trying to repair a broken relationship 3) not enough $$ to play anymore 4) they aged out ad are just not attractive enough or able to pursue young Babies 5) can't sexually perform anymore due to health issues.

Great points, and I've been thinking a lot about this lately, as my GF is back, the memories of my SBs are now almost 2 weeks old (1-2 weeks is my typical 'return to reality' recovery time) and even my relationship with her is starting to feel back to normal. This morning when we woke up, I looked at how my GF looks when she rolls out of bed with no makeup on and I remember one of the reasons I fell for her in the first place.

I think for the sake of our own happiness, we have to ask ourselves realistically where we want to be during the final years of our life, alone, as an ATM machine for a young hooker, or with a partner that actually gives a shit about us. It doesn't mean a little bit of fun can't take place in the interim, but we have to remember it's an extremely addictive hobby to fuck young / hot ladies -- however is it sustainable and can it really be the end game? For me, it cannot be either. I make a decent living but I could never afford to live every month like one of my typical "Daddy Vacation Months". I would have enough disposable income, at least for now during my high-earning years, to have lots of fun but I also have the issue to deal with of my financial sensibilities working against my libido, and I do have long-term financial goals to meet. Historically when I find myself having too much fun, my id balances out my ego and reminds me that all things come at a cost and that I need to remain aware of the true risks / rewards involved.

If I lived alone I could do things like share space in my house in exchange for sex, etc. But I know this would not be as fulfilling as my annual daddy vacation, because unless the lady is someone I can generally be buddies with, watch movies / TV etc (which is one important role my GF fulfills), sex alone is not enough motivation for me to let someone be around me every day. For that reason, even when I was single, I typically focused on finding a meaningful partner and someone who would CONTRIBUTE to the total financial picture rather than just place a drain on it. I once even had a friend-with-benefits who was every bit as hot as the SBs I date now, Asian nurse with a smoking body, sex drive that would not quit and a good career... She started a new job near me and was having a tough job finding a room and wanted to pay me $600/ mo to be my roommate, plus of course easy access to the benefits I was already enjoying. Problem was I was just starting another relationship at the time, I really didn't need the money, and while I liked this girl a lot as a friend, I didn't view her personality as GF material (she would drive me nuts) and I saw letting her live with me as getting locked into something that I didn't want in my life (it would only make it hard to date others).

I have already thought a lot about how things might pan out if I got busted. I don't think my GF would leave me because on the overall meter of who-owes-who, you could say she owes me a big one because of some forgiveness about a situation that took place many years ago. But, I also know it would be years before I fully heard the end of it, and for that reason I might end up sending her packing just so that I don't have to deal with the collateral damage and aftermath. It is absolutely a situation I want to avoid at all costs. Just in the last few weeks, I found no less than three POTs that I really wanted to fuck, and that assured me the highest level of discretion, but they had ties to family or friends that were very close to my home, so for that reason I told them it is too small of a world and that I would not meet them because I don't want any awkward moments down the road. Even when they promised me they were experienced at being a paramour, I know from past experience that the emotions of a young lady are something nobody can predict (and taking her at her word that you can trust her secrecy is foolish). Also remember that once she knows that discretion is not something you want, but something you desperately need, she is in a position to use that as leverage against you to get what she wants at some point (if she is that type of person. Some SBs have a heart of gold but you cannot count on it).

I have seriously considered joining Ashley Madison and looking for someone married who has more to lose than I do, just for the occasional discrete hookup. I have not yet been able to motivate myself to do this, but maybe some of you have tried or considered this route. My problem with it is that I have this vision in my mind of horny cougar housewives who are not in the same hotness league as the younger SBs I've been having fun with, but I don't doubt there are some real gems out there to be mined. Its like any other game, takes practice and determination I'm sure.

[Happy Lover]

I echo that sentiment. I do not know Scott's situation at all but I do know that the Sugar lifestyle is relatively short lived for a married SD. Eventually the sneaking around is discovered and unless divorce is an immediate result the SD is off the shelf struggling to repair the damage done. Many of us want to stay married for a variety of reasons, and have to work through barrels of well earned shit. This is my situation. I still dabble and keep an occasional FB but can no longer pursue a full on SB search. The antennae are up and suspicion is high and every move is monitored. What a life -eh?

So this is why I encourage guys dabbling in the bowl to be absolutely sure that they want to take that 1st step down a road that will inevitably end up in a world of hurt. Now the single guys have it made although some, like JL, have GFs who will bolt if any hint of sugar participation comes out.

So guys who have quit did so IMHO because 1) they were busted by the SO 2) they are trying to repair a broken relationship 3) not enough $$ to play anymore 4) they aged out ad are just not attractive enough or able to pursue young Babies 5) can't sexually perform anymore due to health issues.

Even though I was busted last fall, it seems as though my barrel of shit may not be as deep as yours. Combine that with a flexible business hours work schedule and that is what allows for my playtime. Mind you, that is much more limited than most here on the board. Nights out or sleep overs are usually only possible on a very limited bases, maybe a couple of times per month. Unfortunately, I don't travel for work which leaves my activity area close enough to home for a daytime get together. That is part of what was so painful about Baby1's timing of ending it. She had been pushing for a sleep over, actually getting upset that I always need to wrap things up at the end of the work day. With my SO's "antennae up" that opportunity hadn't been possible until literally the day after Baby1 ended it. They say in life, timing is everything, and that sucked.

With Baby1 out of the picture, I upgraded my sd4 m account and started sending out a personalized form letter. I've gotten a decent response. So far, additional pics that I've received killed it for a few, 1 smoking hot new pot who went dark the day before the m&g, and a couple more who were only available nights and weekends. I'm thinking of contacting pots that are outside of my area or interest and working it a bit just to get my SD legs under me as the number of acceptable pots in my area are limited.

There has been some talk about how different the SB scene is in different locations. I applied my search criteria to a zip code on Hollywood Blvd for comparison purposes. All I can say is WOW! What a difference. I'm in a fairly large market, but I netted 5 times the matches in Hollywood. What was even more striking was the quality of those matches, at face value at least. So far I've been interested in contacting 38% of the matches in my area based upon looks alone. Just taking a stab at a number, but it looks closer to 80% there. Lot's of young beautiful women looking for fame and fortune. So as the bum said in Pretty Woman, "Hollywood, Hollywood, what's your dream?" Apparently it's to be a SB.

[FredMoore]

Good wishes to Scottie in whatever he may getting himself into these days. I think about him a lot & hope all is well.

Good wishes to all my other brothers here in the bowl as well. I've had my own reasons to avoid this lifestyle lately but still hope you are all scoring huge and spreading the love far and wide.

Peace,

Chi.

I echo that sentiment. I do not know Scott's situation at all but I do know that the Sugar lifestyle is relatively short lived for a married SD. Eventually the sneaking around is discovered and unless divorce is an immediate result the SD is off the shelf struggling to repair the damage done. Many of us want to stay married for a variety of reasons, and have to work through barrels of well earned shit. This is my situation. I still dabble and keep an occasional FB but can no longer pursue a full on SB search. The antennae are up and suspicion is high and every move is monitored. What a life -eh?

So this is why I encourage guys dabbling in the bowl to be absolutely sure that they want to take that 1st step down a road that will inevitably end up in a world of hurt. Now the single guys have it made although some, like JL, have GFs who will bolt if any hint of sugar participation comes out.

So guys who have quit did so IMHO because 1) they were busted by the SO 2) they are trying to repair a broken relationship 3) not enough $$ to play anymore 4) they aged out ad are just not attractive enough or able to pursue young Babies 5) can't sexually perform anymore due to health issues.

[ChiGuy606]

What happened to the man? I wanted to catch up on his escapades and discovered he has posted since Dec '13. Anyone know what's up? I miss his writing style and success stories.

Good wishes to Scottie in whatever he may getting himself into these days. I think about him a lot & hope all is well.

Good wishes to all my other brothers here in the bowl as well. I've had my own reasons to avoid this lifestyle lately but still hope you are all scoring huge and spreading the love far and wide.

Peace,

Chi.

[WoodSlinger]

What happened to the man? I wanted to catch up on his escapades and discovered he has posted since Dec '13. Anyone know what's up? I miss his writing style and success stories.

[JZLizard]

Keep doing what you are doing. It isn't always this successful. But you seem to have a knack for it. So my take on it would be for you to give advice more than ask for it. Or just keep reporting.

On the marriage SO side. I have a few opinions on that.

1. Yes I think this hobby can affect your SO relationship. But not necessarily. It all depends on what you are doing what your current relationship is and how you are handling it. If you feel guilty and hate your SO and feel resentment toward her for not giving you what you think you deserve. Then yes. Anything like this will affect it. Most likely you are subconsciously looking for a way out.

2. If you are just out there playing a little and just want some variety then you could probably do this without creating much of a stir in your SO. And are conscious of yourself and not feeling guilt or judging yourself.

But let me offer some other advice. You have been married before and you are headed there again. Now I know nothing about your relationship. But I would urge you to think carefully about your next steps. If you are already doing this hobby and you have not even got married yet. It will not get any better. If you want to spend some money just go ahead and buy your girlfriend a house now. And dispense with the pain of a divorce. LOL.

You have already been married why would you do this to yourself again? If I was in your position. I would use your excellent skills to date and meet as many hot and cool women as I can find until I came across someone. Who could be happy in a LT relationship...possibly even accept a little playing on the side occasionally.

They are out there. But please think carefully. If I was in your position. Even with my ok skills. I would not be in the sugar bowl. I would be out there playing with the civvies. And looking for someone of like mind. And they do exist. I have only had two ATFs my current little Italian Princess and my previous ATF of last year. And both of them would have been perfect for me in a real LT relationship with a lot of sexual openness, both absolutely beautiful, both were fun and interesting. But hey I am already married. And I have kids.

So I continue to play in the bowl. Good luck brother.

Revvo.

I might have given the impression that the current SO is something that will one day lead to marriage when I referred to my "first wife" (as if there might be a second. But, I actually have no intention of ever getting married again. When I first went through a divorce it was a weird adjustment period, and I realized that I had been preprogrammed to believe that being married was one of those things everyone needed to do in order to be happy. I've been in my current relationship close to a decade now (with a couple of separations where I was back on the dating scene) and we do not even discuss the idea of marriage any more. When I bought my current house, I didn't even take the GF with me to look at potential properties. Many years ago I talked to her about the option of buying a house jointly (in retrospect I'm glad I didn't), but at the time that was more because I was trying to test her commitment level. She didn't want to be a part of financing the purchase, so she is not a part of the purchase decision nor is she ever going to get her name anywhere near the property title.

A couple of years ago when we were split up, I was doing just as you said -- civvy dating and looking for something long-term and sustainable. I really don't want a SB-turned girlfriend, they are too accustomed to getting top dollar for their youthful pussies and although maybe I'm just naïve due to lack of experience, I don't see too many of them making a proper adjustment to a situation where they are actually contributing to the household finances rather than simply draining them. The 10 I spoke of before, I can kind of see her doing that with some lucky guy because she was extremely mature for her age, and when I spoke to her about her actual motivation for sugarbabying, I think it was way more about her enjoyment of being an older man's fantasy experience than it was the direct financial help, so I didn't get the impression she is the typical spoiled material girl. I can see her growing out of the SB scene in a few years and wanting to start a family (in fact she told me that's her plan). But most of them, I see them keeping it going until they get to their late 30's or 40's and are no longer taken seriously as sugarbabies, and then I don't know what comes next for them, either they become aging escorts or discount backpage tugjob artists or similar.

Thankfully my current girlfriend does contribute (begrudgingly sometimes, but even that is better than nothing) to the overall household finances (paying a little bit of rent, occasionally buying groceries, etc). She always jokes that she wants me to be her sugar daddy and my response to that is if I wanted to be someone's sugar daddy I'd go find some barely legal girl that I could see once a week and not have to listen to her the rest of the time. Little does she know that's what I actually do when she travels and leaves me here alone.

[Revvo]

Revvo, I call myself a newbie because really I am in the sense of the true Sugarbowl. What I do currently is really just dating and is an extension of what I've been doing most of my life, with the added twist of the fact the girls are disproportionately young for me and that there is some help with bills to be had at the end of the fuck session.

My game got developed early -- even as a small child I was such a horny little fuck, I can remember sitting there in bed at age 7 or 8 with a little boner going, fantasizing about fucking my sisters friends, my moms friends, my teacher, etc. Literally that's all I thought about every night when I went to sleep, and I spent a lot of time plotting how I could satisfy my urges when I got old enough to act on them. Became sexually active at 13 with my girlfriend at the time, but also got a lesson in how manipulative / conniving / deceitful / vindictive / controlling a female (even a teenage one) can be if you allow them to feel like they've taken charge for even a moment. I took the pain from that experience and turned it into a learning experience and developed my craft as I got older. There are lots of areas of handling women that are still quite under-developed for me. My first marriage failed and I still find long-term relationships extremely challenging... It's so much easier for me to serial date than it is to actually live with someone. I have friends that have much better luck in long-term relationships than me and I sometimes wish my skills were more balanced in that regard. But, the portion of my game that is well-developed is the part that pays off big-time in terms of procuring sex during not only SB hunting but just online dating in general.

So the success that I've revealed here is really only part of the equation, I guess, as it only speaks to my ability to quickly take things from the M&G stage to the FC for an epic romp. Beyond that, there is only one SB (and this was a stripper I met in a strip club) that I've even had more than one date with. I think a truly successful SB would have a harem of ongoing, low-cost high quality-pussy, maybe juggling half a dozen or so at a time and making sure when one cycles out that the vacancy is filled with equal or better. Right now my relationship with my girlfriend doesn't allow me to even attempt that. I'm actually envious of HollywoodGuy sometimes, living in a place like L.A. Where there is a constant supply of girls nearby. Maybe if things don't work out with my GF I should move to L.A. .

Keep doing what you are doing. It isn't always this successful. But you seem to have a knack for it. So my take on it would be for you to give advice more than ask for it. Or just keep reporting.

On the marriage SO side. I have a few opinions on that.

1. Yes I think this hobby can affect your SO relationship. But not necessarily. It all depends on what you are doing what your current relationship is and how you are handling it. If you feel guilty and hate your SO and feel resentment toward her for not giving you what you think you deserve. Then yes. Anything like this will affect it. Most likely you are subconsciously looking for a way out.

2. If you are just out there playing a little and just want some variety then you could probably do this without creating much of a stir in your SO. And are conscious of yourself and not feeling guilt or judging yourself.

But let me offer some other advice. You have been married before and you are headed there again. Now I know nothing about your relationship. But I would urge you to think carefully about your next steps. If you are already doing this hobby and you have not even got married yet. It will not get any better. If you want to spend some money just go ahead and buy your girlfriend a house now. And dispense with the pain of a divorce. LOL.

You have already been married why would you do this to yourself again? If I was in your position. I would use your excellent skills to date and meet as many hot and cool women as I can find until I came across someone. Who could be happy in a LT relationship...possibly even accept a little playing on the side occasionally.

They are out there. But please think carefully. If I was in your position. Even with my ok skills. I would not be in the sugar bowl. I would be out there playing with the civvies. And looking for someone of like mind. And they do exist. I have only had two ATFs my current little Italian Princess and my previous ATF of last year. And both of them would have been perfect for me in a real LT relationship with a lot of sexual openness, both absolutely beautiful, both were fun and interesting. But hey I am already married. And I have kids.

So I continue to play in the bowl. Good luck brother.

Revvo.

[HollywoodGuy]

JL, I am just like you. I hate being alone and I like variety. Its a dilemma for sure. I used to serial date or marry, always living with someone. Most girls are not interested in living with someone in an open relationship. Quite by chance I ended up where I am now. With a roommate that takes care of me when I need it and who is not my SO or GF in any way. More of a best friend. And she keeps all the girls that would like to move in on me away.

When I am living alone, I am weak and girls sense this and try to take advantage. So for now this is my solution. It's like an insurance policy, because it does cost me. But I am sure far less than if I had a GF living here. My roommate currently has a new and very generous SD and a hot young BF, so there is no emotional drama between her and I. I just make sure she looks good, has a safe place to chill and is well fed. I don't really have an answer to your situation, I can only share mine.

Just an added note to the lurker who reports all my posts to her. She has free rent, my protection, a generous SD that is spending money like water on her and a super stud BF that you can never compete with. So why don't you just admit you don't have a chance with her and go away already. Aren't you tired of being some lame stalker dude? You obviously know how to read, so why not just take some tips from this site or cruise hollywood blvd for some desperate homeless girl to take advantage of?