Tuesday, November 23, 2010

Sex, Money, and Sugar - Part 4

Part 4 - Trust, Allowance, and Intimacy

One of the most often mentioned conundrums in the sugar world is which comes first, the allowance or the intimacy??  While that's an easy question to ask, there is a wide variety of opinions and there is no one size fits all approach.  We all do what we’re comfortable with based on our experiences and risk tolerance. While one contemplates the issue of allowance and intimacy, the most important factor to consider is "trust".  It's important to remember that trust is earned and built over time, it shouldn't be assumed or given haphazardly.

Let's look at various approaches to allowance and intimacy from the SD's point of view and see the implications.

1.  "There is no way in the world I will give someone a half month up front or anywhere close to that early."

This is a more risk averse approach for the SD's.  But the trade off is that some pot SB’s may not be open to this approach by taking on more risk on their end.

2.  "I’ve always agreed with those who say half the allowance up front, before intimacy, is a reasonable compromise. That way if the thing quickly fizzles out due to poofing or otherwise, it is not a complete loss for either."

There is more risk taking on the part of the SD and he is willing to take on the potential loss. Poofing or non-performance by the SB (or SD) is always annoying, but perhaps it’s less annoying when only half of the allowance is at risk.

3.  I pay it forward, it really builds trust very quickly. Having the financial discussion is difficult for some people, by paying it forward it makes both of you feel comfortable and get the discussion out of the way quickly and simply. 

The SD is taking on most of the risk in this case by paying the allowance in advance and trusting the pot SB to do her part.  But how does one know for sure if the pot SB will actually do what she said she'll do, and what if she doesn't?

The allowance-intimacy issue comes down to whatever the two people involved can agree on, much like any arrangement.  The best result from any relationship is where both parties invest in the relationship, and to a certain extent, take chances. This way there is an element of commitment from both parties by investing their time, money, and effort.  The word “mutual” in mutually beneficial also applies to how both parties are willing to invest and take chances to build trust in the relationship.

We all want to be treated with the same respect and trust we’ve shown to others. However, in the sugar world, common sense and common courtesy may not be so common after all.  In the risk-reward equation, there are people on either side of the spectrum ranging from risk averse to taking unnecessary risks. I can’t imagine there could be much success on either side of the spectrum, so what usually works is somewhere in the middle in terms of taking risks in a prudent manner by both sides. And as I said in the beginning, there is no one size fits all approach and we all do what we’re comfortable with based on our experiences and risk tolerance.

Coming up - Part 5, First Meet and Beyond

Tuesday, November 9, 2010

Sex, Money, and Sugar - Part 3

Part 3 - Escorts vs SB's

This is another popular topic in the sugar world.  When sex and money are involved some people take a black and white view, while others understand there can be many shades of grays. 

What constitutes an escort

Many years ago when I dealt with escorts on a regular basis it was pretty clear to me what constitutes an escort.  They advertise their services with clearly defined rates and there is no screening other than for safety.  It was easy to arrange an appointment and there was no need to consider mutual attraction, compatibility and chemistry so just about anyone who can pay the advertised rate can do it.  To really get what I want in terms of looks and services it took some work to research escort reviews to make sure my money was well spent.

In general there are three factors that characterize escorts.

- Volume. Escorts tend to have sex with a larger number of men.
- Availability. Escorts will usually have sex with just about anyone who can pay their asking rate.
- Service. Escort's service level (ie what she is willing to do) is usually well documented through reviews.  I understand YMMV, but most of the time it's fairly consistent and replicable. 

So, just because sex and money are involved in a particular situation, does that automatically make the woman an escort?  Apply the criteria I described above and see where she fits.

Pro vs non Pro attitude

Instead of escort vs SB, I prefer to look at it as pro vs non pro. It's more about the attitude or mentality of the woman and less about what the arrangement is or what she does for a living.

A pro attitude means that she values money as the most important criteria. There are other factors she'll consider but it still comes down to money. For example, a typical stripper or VIP hostess type who is not an escort can still have a pro mentality. They think in terms of how much they can make a night working without having sex with anyone, then argue why should they take the same or less money to have sex with someone. With this type of attitude they will typically look for the highest bidder and there is usually a clear linkage between money and performance.

A non pro attitude means that while money is an important factor, it's not the most important one. She will take other factors into consideration such as chemistry, attraction, compatibility, etc. She usually thinks about money in terms of what she needs and not what the perceived "market rate" is. If the money offered suites her needs and she likes who she's spending time with, then that's good enough for her. They don't go to the highest bidder because they don't necessarily think of putting a price on what they do. There is less direct linkage between money and performance.

Also, their attitude may not be related to their experience level or what they do for a living. There are newbie SB's who will approach it with a pro attitude thinking if they're going to do it at all then they want to get the most money possible, while other newbies have no clue what they want and what they're willing to do.  There are some escorts on SD sites who will approach it with a non pro attitude as well.

The Escort Fallacy

It's not unusual to see some SBs compare themselves to escort rates for their allowance expectations.  Their thinking is if an escort can get $X / Hour or $Y / Day, then surely they're worth a lot more. While that thinking may appear to be reasonable and logical, from a SD’s perspective it’s really counter productive. Being a SD means that we’re not looking to pay by the hour or by the day for an one time trasnaction. That’s what escorts are for. We’re looking for someone we enjoy being with and care about to build an on-going relationship. And on top of that we're willing to provide the financial assistance she needs to make her life easier and reach her goals.

If a SB wants to be paid the equivalent of an hourly or daily rate, then that could really turn some SD's off so I’d suggest they don’t get into the “escort fallacy”. A better way is to think about what your needs and goals are and explain that clearly to the SD and let him know your expectations. If a SD’s offer does not meet your expectation, then simply thank him for his time, decline his offer and move on.  There is no need to justify a SB's "worth" by comparing herself to escorts.  I'm not saying SB's doesn't "deserve" more than escorts, I'm just saying there are better ways to convince a SD of your "worth" than comparing yourself to escorts.

Coming up, Part 4 - Trust, Allowance, and Intimacy

Tuesday, November 2, 2010

Sex, Money, and Sugar - Part 2

Part 2 - Allowance in Real Dollar Terms

Allowance is one of the most popular topics in the sugar world and there is no shortage of opinion about it.  Instead of passing judgment on what's fair and reasonable for what's offered or expected, I'd like to examine what it means to have an allowance in real dollar terms.  This will take into account real world factors such as taxes and discretionary income and compare that to established benchmarks.

For example, according to the US Census Bureau, annual median household income in the US is $49k, top 5% starts at $157k, and top 1.5% starts at $250k. Keep these numbers in mind as we look at allowance expectations in real dollars terms by taking into account taxes and SD's discretionary income.

On seekingarrangement.com a SB can indicate the amount of expected allowance in her profile. Let's look at what it means to have $1k, $3k, $5k, and $10k per month. And for illustration purpose let's assume a tax rate of 35% since SD's should be high income individuals.

$1k/month - $12k per year after tax or the equivalent of about $17k before tax.

$3k/month - $36k per year after tax or the equivalent of about $51k before tax. Note this is already higher than the median household income.

$5k/month - $60k per year after tax or the equivalent of about $86k before tax. Note this is more than one and a half times of the median, or more than half the amount of what the top 5% makes.

$10k/month - $120k per year after tax or the equivalent of about $171k before tax. Note this will put you in the top 5% of all US households.

Now that we have put those numbers in perspective, let's realistically think about what are the chances of finding SD's who can provide that kind of allowance as part of their discretionary income. For illustration purpose, let's assume a SD has 20% of his gross income available to spend on a SB. This means the SD should have an income of five times the amount he provides to the SB. Keep in mind this is his total spending on a SB, for which the allowance may only be a part of. This percentage may vary based on each SD's situation such as whether he's single or married.

$1k/month - The SD would need to have a gross income of $85k per year, this is already way above the median income.

$3k/month - The SD would need to have a gross income of $255k per year, this is already in the top 1.5%.

$5k/month - The SD would need to have a gross income of $430k per year.

$10k/month - The SD would need to have a gross income of $855k per year.

The analysis shown was for illustration purpose only.  One can use different assumptions about tax rates and discretionary income to come up with different figures.  But realistically, how many wealthy men can we expect from the top 1% to sign up on one of these web sites and are serious about being a SD and part with their money?? Think about what kind of work or business the SD should be in to make that kind of money, where they're located, their age and marital status, and what kind of SB they'd be looking for. Will the top 1% of SD's look for an "average" SB, or would they look for the top 1% in SB's as well? What kind of a "real" job would a SB have to get in order to make the equivalent of the allowance she is seeking?

I'm not passing judgment on what people are looking for or what they expect, and I know there are success stories across the spectrum. I'm just applying a straight forward analysis to help those in the sugar world to have a realistic view.

Coming up - Part 3, Escorts vs SB's

Tuesday, October 26, 2010

Sex, Money, and Sugar - Part 1

I'll take a break from telling stories to start a multi-part series titled "Sex, Money, and Sugar" to discuss the intricate nature between sex and money in a sugar relationship.

Part 1 - SD's income/wealth/budget vs SB's expected allowance

On sa.com a SD's profile includes information about his income, net worth, and budget for an arrangement, and a SB's profile includes her expected allowance. But like everything else on the internet, keep in mind anyone can create a profile and put whatever they want in it.  Therefore it's probably not a good idea to take everything you see at face value and assume the information is accurate.

I usually look at whatever is listed for expected allowance in SB profiles with a grain of salt. There are SB’s who consider the amount of allowance as their most important criteria and therefore will not be flexible. And there are SB’s who will consider the amount of allowance along with other factors and are willing to be flexible. Then there are SB’s who purposely put a large amount to weed out the undesirables but are willing to consider less from the right SD. You won’t know which type you’re dealing with until you have a dialog with them. Once you figure out what you’re dealing with then you can proceed accordingly.

Here's one of the most counter intuitive lessons for SD’s to learn. That is, the amount of allowance may not be directly related to the quality of relationship and experience. A higher allowance can usually get you younger and hotter arm candy, but there is no guarantee for a better experience. For example, would you have better chemistry with a SB because she is asking for a higher allowance? Or, would a SB asking for a higher allowance be more reliable?

Likewise, I’d suggest SB’s to look at a SD’s listed income/net worth with a grain of salt. Some SD’s purposely under state it because they don’t want pot SB’s to have unrealistic expectations. Some SD’s purposely over state it to attract SB’s that they otherwise wouldn’t be able to attract.

Here's one of the most counter intuitive lessons for SB’s to learn. That is, a SD’s wealth, income, and lifestyle may not directly relate to how generous and how willing he is to provide an allowance. He has to be able and willing to do so. Some wealthy men are willing to spend lots of money on fine dining, travel, and gifts because they think sharing a piece of their lifestyle is good enough to be a SD. But when it comes to providing an allowance they think there is a stigma associated with it as if they’re too good to be “paying” for a SB. Therefore, for SB's who are looking for an allowance, these wealthy men will just end up wasting their time.

Coming up - Part 2, Allowance in Real Dollar Terms

Friday, October 22, 2010

The Sugar Triangle - Part 5

Part 5 - The Happy Ending?

I thought after Bob sent Alice packing that was the end of it but then two weeks later she sent me this email: 

Just thought I'd update you with the latest in the saga.  I'm not trying to start an argument, pass judgment, nor seeking advice.  Just a friendly, "Have you heard" kinda exchange.

I typically don't put much stock in rumors, however the information comes from what I consider to be a reliable source (at least as reliable as the information you presented which was close enough).  The two that have provided this information are fairly close to her and are evidently part of the wedding party.

She had her day in court and is now officially divorced form her husband.  The SD and SB are now planning a fall wedding with all the trimmings complete with a honeymoon in the Caribbean.  They are in the process of closing on a multi-million dollar estate in a gated community near her.

Their profiles are removed from the SD site so they evidently are not looking or wanting contact from others looking.  (Unless they have changed their IDs and are there under another name).  When I called him to say hello, the answering machine message now includes a "we" as part of the message.

I guess their feelings were real and they both were looking for an exclusive relationship after all.  Time will tell if they do in fact go through with things and last.  Have you heard anything?  Are you still seeing her?  Just thought I'd drop this one on you and see what else you knew.

Hope things are well with you!

Apparently there were people who were more in the know than I was.  I found the rumor hard to believe, but if it's true then good luck to them!!

However, more than a year later I found out Crystal was back on the SD site and flew out to meet with a SD friend of mine.  It's a very small world indeed!  So I guess the happy ending for Bob and Crystal, if there was one, was short lived. There was no word on what happened to Alice.

The end.

Wednesday, October 20, 2010

The Sugar Triangle - Part 4

Part 4 - Sugar Triangle No More

Several days after my conversation with Alice, she posted this on the sugar forum: 

Bob is the most kind and considerate man I had ever known and generous sugardaddie I almost had. He was genuinely concerned and offered advice, guidance, or occasional financial assistance when the times were right. He was most respectful toward me and other women in general.

I knew he had a sugarbabie and that she did not have as much time to spend with him as he desired allegedly due to her normal job and her child. I knew he cared for her very much and yet I tried to come between them.

In discussions with others from the SD website I obtained information that perhaps all her time she could not spend with him was not with her child or her job. That she had other sugardaddies for additional fun.  I visited him and gave him what I believed to be true evidence of her seeing others. I knew this would upset him and I don't know if I was truly trying to keep from hurting him more in the long run or if I was greedy and wanted more for me.

As it turned out, he truly was upset. He and she had some heated discussions over the phone. Some of the times that had been given to me when she was allegedly seeing others was actually traveling with him, or visiting his home.

The bottom line is that I was cordially asked by him to fly back to my home that evening and not call, write, or come back ever again. He and she are a stronger couple now than they were before and both their profiles have been changed on the website to indicate they have found their one.

I was cautioned not to do anything stupid by some on the board. I was told not to interfere and just be the best I could when he was with me. I allowed myself the delusion that I knew better and that he would end up being devoted to me. Evidently I still have a long way to go toward maturity.

What did I learn? No matter how good your intentions or motives do not try to get between an established couple. Be sure of your facts, and find a sly way to make them know when the time is right. Also do some real soul searching to find out what your intentions truly are.

Some day I hope to find someone as nice as he was, is, and will continue to be!

I specifically advised her not to confront him when she went to visit him but she did anyway.  I don't know who else she talked to about her situation, but everything I told her was based on my own experience which I knew to be accurate.  Somebody else may have given her bad information or passed on gossips and rumors.  What a tangled web we weave!!

Coming up - the happy ending?

Monday, October 18, 2010

The Sugar Triangle - Part 3

Part 3 - The Sugar Triangle, Plus One

Let's recap the situation so far.  Bob appeared to be in a "serious" sugar relationship with Crystal, who I met three times, and he was also seeing Alice as a SB, who was aware of his relationship with Crystal.

After seeing Alice's post I felt like I'm in the middle of a soap opera watching the plot unfold, while playing a bit part with peripheral ties to the main characters.  But that's about to change as I decided to reach out to Alice by email.  She was young and new to the sugar world, and it appeared that she's stepping on some sensitive toes and she could get hurt if she's not careful.  Here's what I wrote to her:

Seems like you have a good thing going with your SD. I think what he does or doesn't do with his other SB is his business and you shouldn't worry about it too much. Whether the other SB is taking care of his needs or not, you just need to do what you're comfortable with and take care of him. Then  whatever happens, happens. As long as you are not doing anything deliberately with malicious intent to hurt someone then I think it's all fair.  I think I know the people involved here but that's really none of my business anyway. Good luck! Let me know if you have any questions.

Obviously my email got Alice's attention and she replied right away: 

I replied to your email a few moments ago along with a few others that I received.  I have come back and read yours again a little slower and see things I did not previously notice. You KNOW us?  Am I some sick game to him/them?  what do you know of the situation and the people?  This is disturbing to me, especially since you wrote me personally.  I do not like to be made a fool of at any time!

Another reason I was asking these questions and getting opinions is that he has asked me to go look at an estate with him.  He wants my opinion on legal matters and on some of the details and such.  I also know it is a ploy to spend time with me, and frankly I do want to see a multi-million dollar estate.  If he is serious, this estate places him closer to me than he is currently.  I do not know for sure, but I think she is in the same area, and therefore would also put him closer to her than he is now. 

I guess all things considered I never realized I might be sharing someone and I don't think I am comfortable with that. I do appreciate your comments but if you know or suspect more please tell me! Thank you.

I gave her one more email reply and suggested we talk on the phone:

Yes I know the people involved but it's really none of my business so I didn't want to say too much.  I don't want to get involved in other people's personal lives especially if it doesn't concern me. However, I think it would be important for you to get a better understanding of the full picture, whether it's good, bad, or ugly, so you can make your own choices.  Especially because you seem to care for your SD a lot and it might develop into something serious.  Let's talk on the phone to discuss further.

During the phone call I told her what she wanted to know.  I also advised her not to act irrationally or emotionally because that will only make things worse.  Being in a sugar triangle sucks and it rarely ends well for anyone.  Despite my advice, I got the sense that she was about to do something she might regret.

Coming up - Sugar Triangle No More

Saturday, October 16, 2010

The Sugar Triangle - Part 2

Part 2 - The Plot Thickens!

While Bob's name was being mentioned in one sugar forum, Crystal's name came up in another forum!!  A SD was inquiring about her and wanting to know if any of the SD's have come in contact with her.  Shortly after, he posted that he was supposed to meet her but she flaked out due to some family emergency, but she gave him mine and Bob's handle as references to show that she's for real!!

By now I'm thinking.... WTF!!  I've only met her three times and I'm supposed to be her reference??  And what's Bob got to do with this??  Sure enough, shortly after that post I got an email from Bob: 

I have questions about her and your meetings.  She is leading me to beileve that she wants an exclusive relationship.... I take it from you that I am being misled.  Can you give me the lowdown? Thanks.

I replied to him with what little I knew about Crystal and confirmed that we did meet three times.  He thanked me for the information and I didn't hear from him again.

A few weeks later Alice posted again on the sugar forum.  Apparently by this time a lot has happened between her and Bob.  She wrote:  

I am new to the sd/sb arrangements and do not know what is considered proper or acceptable and I need some advice.

I have been in contact with a very generous gentleman that has helped me in some times of need. We have met and he is truly a gentleman in his actions and has asked nothing from me in return for his help. (I even visited him in his recent hospital stay of which he reimbursed my travel expenses.) The topic of sex has not come up although I can tell he is very interested in me physically.

The dilemma: He has a sugarbaby that he cares for very deeply. I know he is providing much more assistance for her although her schedule and his do not allow them to see each other as often as he wants. I do believe that if she was more available to him he would marry her in an instance. Because she is not available enough for him, I have had the opportunity to get to know him better. He is a very likeable and generous guy that I could spend even more time with if he wanted.

I don't wish to overstep bounds and knock another sb out of a good thing; but at the same time if she isn't taking care of business then she should lose out. Is all fair in love and money? Should I not give her another thought?  Waiting for your opinions and advice.

Obviously the SB in question is Crystal, and things seemed to have gotten pretty serious between her and Bob in a short period of time.  But why is Alice still involved, and what is Bob trying to accomplish with her?? One of the replies to Alice's post pretty much summed up my sentiment:

This is a perfect example of a very screwed up dysfunctional relationship. If I were the man in this tryst, I would be incredibly embarrassed. These types of friendships are usually very discrete, and no one wants to have their dirty laundry aired in public. If this man had no money and wasn't so willing to part with it, I'm sure both women would be looking elsewhere.

Coming up - The Sugar Triangle, Plus One

Thursday, October 14, 2010

The Sugar Triangle - Part 1

Part 1 - It's a small world

Everyone loves a soap opera, right?  Here's a convoluted situation I got myself into, please note the usual disclaimers apply.

During my early days in the sugar world I had several experiences that were one and done or fizzled out after a few meetings.  One such case was with Crystal (not her real name), she was in her early 30's and a single mom trying to make ends meet.  I stopped seeing her after three meetings because even though we enjoyed each other's company, I just didn't think we were that compatible and had much of a connection.  I didn't think much of it at the time and moved on and so did she.

Not long after, in an online forum for sugar relationships (this was before the days of Facebook and blogs) I noticed a post from a newbie SB named Alice inquiring about a pot SD named Bob (not their real names).  She wrote:

He seems like a very nice guy named Bob from [removed]. We have written some emails and talked on messenger only when I initiate the emails or conversation. He did give me a phone number that works and sounds nice on the phone, too. He helped out when my car broke down recently but seems hesitant about actually meeting. He has been polite and has not wanted any naughty pictures, webcams, or asked anything in return. Is he just a benevolent gentleman? Anyone else know anything about him? Should he be avoided?

She got several replies giving her advice.  One of the replies she got was from Crystal and that got my attention! Crystal wrote:

First of all I would like to say I know Bob pretty well. He is a very sweet and genuine person. I have met him on several occasions and we get along great. Secondly, He isn't just a flirt or penpal type guy. He is a true gentleman. Last thing, Alice as far as advise for you...Just ask if he is still interested in seeing you? He is the kind of guy that will say yes or no pretty easily. I am a person that believes if you want to know something about someone ask them first, If you don't get what you want then move on to other avenues like this. If you feel he is putting you to the side or not giving you enough attention that you need then why do you want him as your sugardaddy? Just my thoughts.

Hmmmm... so Crystal knew Bob very well who was also interested in Alice.  Did Crystal meet Bob before, after, or during the time she was seeing me??  Since I wasn't seeing Crystal anymore it really didn't matter, but I suspected there was a lot more than meets the eye and I was intrigued by the situation.

Coming up - the plot thickens!

Tuesday, October 12, 2010

"All SD's To Me Are Just Walking ATM's!"

I almost fell out of my chair when I read that! After the initial introductory email, here's the email exchange I had a few years ago with a pot SB about meeting for dinner to get to know each other first.  I'm not making this up!! 

Me:
For our first meeting I think meeting for a nice dinner would be a good start. It's important to see that there is mutual attraction and chemistry and see how well we get along together. Then we can take it from there. What kind of food do you like and what are your favorite restaurants? 

Her:
well...i hate to be blunt...but that's not really been my thing...i mean dinner's a little too intimate for me...i'll go to dinner though...but i expect to be compensated for my time....as this approach is somewhat new to me...chemistry has never been a problem....i mean, if i went to dinner with everyone that wanted to....i'd never find a real sugar daddy who understands my needs....and it's not just a free meal...so think about it...and u've seen my pics...so i think attraction is not a problem...but i'm definitely here for a sugar daddy....restaurant choice should u choose to partake is (name of a five star steakhouse). 

[So she thinks attraction won't be a problem... but what if she doesn't look like her pics?  And how does she know chemistry won't be a problem when we haven't even met in person?]

Me:
I understand where you're coming from. Of course you don't want to go to dinner with anyone who asks, you want to be selective. On the other hand, I don't want to pay someone just to have dinner with me. We both invest our time to see if there is a good match. And if money is the only thing you care about then obviously we're not a good match. 

Her:
it is a sugar daddy site....but i've had it fulfilled before so i know it's not an impossible request...but i thank you anyway....i mean, if u dont think i'm here to get financial compensation...then i'm sorry if there was a misunderstanding....if u dont need to pay someone for anything....maybe this isnt the site for u....i just have a different approach when it comes to these things...well...have a blast here ....if u change your mind and realize what's money anyway....then u can email me and we'll meet.... 

[There's that old trick... "what's money anyway", implying that if you're a real SD then surely you don't mind throwing some money away.  Ummm.. I don't think so!]

Me:
Perhaps you mis-understood what I was trying to say. Yes, we all know this is a SD site and we're here for a reason. I don't have any problem providing for my SB financially once we determine that we're a good match and have an arrangement. But if every potential SB I meet ask for money just to have lunch/dinner with me, how do I know which one is sincere and not just looking at me as a walking ATM?

I think it's fair that both men and women invest their time initially to find out whether the other person is right for them. You seem to assume that you're the right one already and are asking for compensation just to go to dinner. Think about how that comes across to a potential SD. Of course it's only money.... but if I want to throw it away I could do it at the casino!  We do have different approaches and that's ok. Like I said we're probably not a good match anyway. Good luck! 

Her:
yep...u'll be surprised how many have given me so much just to have dinner with me or grace them with my presence...all SD's to me are just walking ATM's....check my profile...i said it...nothing wrong with that....a walking ATM that gets to be with a goddess like me.... 

[Whoa, now she's showing her true color! Are you fucking kidding me??]

Wednesday, October 6, 2010

The Girl Who Pissed in the Alley - Part 1

After an emotional story like "The Last Hurrah", I'll switch gears and tell a different kind of story. Please note the usual disclaimers apply.

During a business trip to Chicago I arranged to meet a pot SB for dinner.  She was in her mid 20's, a cute slim blond who worked as a waitress and bartender.  I asked her to pick a place to meet and she picked a nice restaurant in the Wicker Park area which she said is the SoHo of Chicago.  Unfortunately I was tied up at work that evening and was going to be late for the dinner planned at 8:30pm.  Sure enough, as I headed out I looked at my phone and saw several messages from her saying she's already there and where the hell was I. 

I replied to let her know I'm running late but I'm on my way and she can go ahead and order whatever she wants. By the time I got there the place was empty and she was sitting at the bar chatting up a storm with the bartender.  Apparently she's already had dinner and downed a bottle of wine, so I just ordered dessert and had a glass of dessert wine to go with it. Obviously after a bottle of wine in her slim body she's pretty lively and friendly and was ready to party.  The bartender said after they close they usually hang out at Empire which is a cool bar and lounge.  So we agreed to meet the bartender and her friends there later and then we walked down the block to a pub and had a beer and two shots.  Then we walked across the street to Empire. The place was pretty dead but the music was good.  We had two cocktails and two more shots and this is when I decided to stop drinking.

She seemed pretty smashed but had no problem with making out in the quiet corner of the lounge as we were tongue kissing and caressing each other's body.   Then she was dancing by herself and chatting up anyone and everyone in the lounge and I tried to keep up with her to make sure she doesn't get into trouble.  After a while the bartender and her friends showed up and I bought two rounds for them and of course she participated too.  The bartender noticed that my date was looking shit faced and took her to the ladies room to try to sober her up, but I think she was beyond drunk and it didn't do much good.  Then we left to go to another bar with live music to hang out and dance for a while without drinking.  We were approached by another couple who invited us to go "party" at someone's house.  I didn't get a good vibe from them so I passed.  By now it's about 2am and I thought we should be heading out so I tried to get her to move along and she refused and wanted to party and drink some more.

Of course you can't really argue with a drunk and get her to do what she doesn't want to do.  So I struggled for a while and finally got her out the door, then as we walked past the pub we were at earlier she insisted that she wanted to go in.  I gave the bouncer a knowing look and he refused to let her in and she threw a fit.  Then she went into the alley and tried to go in the side door. When that didn't work she got very upset and pulled downed her pants, squatted down, and started peeing in the middle of the alley!!

At this point, what should I have done?

A. Cut my losses and leave her in the alley.  I don't need to make a bad night any worse.

B. Bring her to the pub and let her drink some more, since that's what she wanted anyway.

C. Take her to party with the other couple at someone's house. Who knows, it could be fun!

D. Take her back to her place and tuck her in. That's what a gentleman would do.

E. Something else?

To be continued....

Monday, October 4, 2010

The Last Hurrah - Epilogue

We broke up for good after the big fight that ended in a train wreck. We stayed in touch occasionally to wish each other happy birthday and happy new year, but not much more.  We had both moved on and it was for the best, because somehow we brought out the worst in each other.  When it was good it was beyond great, but when it was bad it was down right explosive.  I told her she reminded me so much of my college girlfriend, but who needs all that drama in a sugar relationship?

Fast forward a year and a half later, or about two years after we first met.  I was back in her town for business and on a whim I thought I'd look her up.  She was happy to hear from me and agreed to meet and catch up.  I asked her where she'd like to meet, and instead of picking some fancy place she wanted to meet at a hole in the wall ice cream stand.  Then I remembered that's where she took me to during one of our first dates when things couldn't be better between us and we couldn't get enough of each other!!

I was a bit apprehensive going into the meeting as if I was meeting her for the first time all over again.  I wondered which Laine will show up.  The manipulative conniving drama queen, or the easy going pretty girl next door?  She showed up as planned and greeted me with a big smile and a big hug.  She was just as I remembered when I first met her, very pretty in a girl next door kind of way, dressed casually with a tube top, jeans, and flip flops, witty and funny. And she knew exactly how to keep me on my toes and made fun of me every chance she got.

It was a beautiful afternoon and we spent about an hour talking nicely and enjoying the ice cream in the sun.  She said after we broke up, her mom somehow found out about her escort activities and demanded that she go home and stay with her to keep her out of trouble (thank god for mom!).  Then she returned to help out with decorating and managing her family's rental properties in the area.  Sounds like she had put her wild days behind her and was back to "normal" again.

I can't help but wonder if I met her for the first time then, what would have happened?  But there was too much water under the bridge and that ship had sailed.  I knew behind that sweet face a darker past just lurks around the corner and who knows what else lies beneath the surface.  But on that day, with the sun shining and a light breeze, we were able to enjoy the simple pleasure of eating ice cream and having an interesting conversation like two normal people. 

We have seen each other at our worst, but it was nice to know that she can still be the girl I remembered when we first met.  We hugged each other goodbye as the heart in the sand flashed before my eyes and "Goodbye My Lover" echoed in my head.  That was the last time I saw her.

About a year ago she wrote on her Facebook that she was getting married.

The end.  (really!!)

Friday, October 1, 2010

The Last Hurrah - Part 10

Part 10 - The Train Wreck

We made it to dinner and the staff was very efficient so it went by very fast. Considering it's a fine dining establishment I almost felt like we were being rushed out the door, which was just fine by her because she said she has a "hot date" with her ex afterward. We talked about why she picked "Goodbye My Lover" as our song. Didn't she know the lyrics and how emotional the song was? She claimed that she only knew the chorus when she picked it, but agreed that the words were very appropriate to our situation.  She said she will go get the photo CD and drop it off at my hotel later but who knows if she will actually do it or not. Soon it was time to drop me off at the hotel and I thought it would be nice to spend more time together so I invited her to come up and chat. But she would have none of it and actually got out of the car to take my luggage out of the trunk. Then I noticed that she left her cell phone on the driver's seat so I grabbed it and got out of the car and told her goodbye. I figured this was a good way to return the favor for stealing my camera.

Not long after I got to my room she called from the pink cell phone I gave her (it was a gift from our third meeting) to ask me if I've seen her other cell phone. I played dumb for a while and she got impatient and said  she will go back to the restaurant to look for it and hang up on me. I sent her text messages to let her know that I have the phone and she should come get it but I guess she didn't check her messages. Then about an hour later she called again and this time I told her to come see me because I "found" her phone. I said she dropped it and I picked it up, and I was going to give it back to her but since she was in such a hurry to ditch me after dinner so that's why I didn't give it back to her. Of course she wasn't too pleased and I told her to bring the photo CD and negatives in exchange for her phone.

Soon she showed up and looked very agitated. She demanded for her phone and started to look all over the room for it. She figured out quickly that I had it locked in the closet safe and demanded that I open it. I told her to calm down and talk for a bit but then she started to go through my stuff and grabbed my wallet out of my brief case. Of course I can't let her take my wallet so I grabbed her arm to take it back.  This is the second time we got into a bit of "rough play", and the first time was when we broke up after three months. By now I can see that she is extremely sensitive to it for whatever reason.

After I took my wallet back from her she basically lost it and screamed and shouted non stop for her phone. Finally I opened the safe to give her the phone, and she threw the CD and negatives on the floor and left in a huff. I asked her, "what's the matter, can't take a little joke?" Obviously she is much better at dishing it out than taking it. I also told her "it was nice knowing you" as she slammed the door on her way out. After that fracas she actually called me twice the next few days and we exchanged a few text messages. It turned out that she really wasn't moving and she expanded her weekend job to 3-4 days a week with 12 hour shifts. She was still active on sugardaddie.com but I noticed that her profile on seekingarrangement was not searchable anymore. I'm sure her "escorting" on the side continues, but who cares.

So despite my best intentions to breakup amicably during the Caribbean trip, we still end up having a big fight that resulted in a train wreck.  It was similar to how we broke up the first time after three months. Will this ever end?

Coming up... The Epilogue

Wednesday, September 29, 2010

The Last Hurrah - Part 9

Part 9 - The Stolen Camera

After the Caribbean trip I thought that would be the final chapter on Laine. But noooo... there would be a little more to it and why wasn't I surprised.

After I discovered that she stole my disposable camera I was pretty upset. But I decided not to do anything about it at the time and see what would happen. A week after our trip she sent me an email asking me to send her the pics, as if I still had the camera. I wrote back saying that she must be joking because she is the one that should send pics to me. We exchanged a few more emails and she finally admitted that she did steal the camera and offered to get the pictures developed then send the photo CD and negatives to me by mail.

I told her I'll be in town for business and we can meet for dinner and she can give it to me in person. She wasn't sure if she wanted to meet but finally agreed. Then we talked on the phone for the first time since the trip and we talked for almost two hours. As usual I don't know if I can believe everything she says. She said she is done with escorting on the side and will "retire". She has used the money she made to buy a new house and that's her investment. I reminded her that she still has the brokerage account I opened for her but she hasn't used it yet. She told me to go ahead and move some money from her bank account to the brokerage account to get a better return and I did that for her. It was an interesting conversation and it showed that we were still "connected" at some level and there was still some trust.

When I arrived to see her she came to pick me up at the airport like she has always done before.  But I noticed that she was wearing a brand new outfit with a red Bebe top, designer jeans rolled up at the ankle, and a pair of red stiletto pumps to match her top. I guess all this must be from the shopping spree at Bebe that she mentioned her new SD took her to last time. In the car we talked some more and continued our conversation. She made no mention of any of the new guys and told me that she will be moving to start a new job next month. Whatever. It's just her normal randomness and for all I know she could be making it all up.

Then we talked about her outfit and she said facetiously that she wanted to look unattractive for me, and I said she is doing a very good job. I actually meant it, because even though her top looked sexy, her jeans and the rolled up look was not flattering on her.  And the shoes… it's the first time I've seen her wearing four inch heels and she looked uncomfortable walking in them. Of course I didn't tell her all that, but she didn't like my reply and retorted by telling me that she has a hot date with her ex after we have dinner and she wanted to spend as little time with me as possible. What a nice way to rub it in my face! And on top of that she said she forgot to bring the photo CD which made me wonder what kind of games she is playing now.

Coming up... The Train Wreck

Monday, September 27, 2010

Evolution of a Sugardaddy - Part 7

Part 7 - Where I am today

I'll take a break from writing "The Last Hurrah" and resume the "Evolution of a Sugardaddy" series.

After looking back to see how my approach has evolved, where does that leave me today?  As I have mentioned before, during the first three years in the sugar world I got emotionally involved 3 times and 2 of those relationships lasted six months which I considered as "long term" at the time.  The first one ended in blackmail (which I'll write more about in a future story titled "Seeking Long Term), the second one broke my heart in "Mixing Love and Sugar", and the third one ended in a train wreck in "The Last Hurrah".

After "The Last Hurrah" I was determined not to get emotionally involved again.  I have been much happier ever since and my sugar relationships started to last a lot longer.  Since then I had 3 sugar relationships that lasted 6 months which were long distance, and 3 more that lasted for more than a year that were local.  In between there were several cases of one and done's or the arrangement fizzled out after a few meetings.  I don't consider anything less than 3 months as a "relationship", it's more like an experiment that didn't work out. All of the arrangements were financially based instead of gifts/travel. I think I have finally found the key to success in the sugar world for my situation!

Currently I'm happy with the sugars I have and I'm not actively looking for more.  Whenever my current sugar relationships come to an end (they all end eventually), I'll probably decide to take a break for a while.  I appreciate those who have inquired about my current status and I'm flattered by those who have expressed interest to meet in person.  For now I'd prefer to keep my privacy and keep a low profile, and share my experiences and learn from others through my blog and the SeekingArrangement blog

In the next part I'll summarize the key lessons learned during my years of sugar experience.  I can say I have finally put those lessons to good use and that's where I am today.  I'm sure there are still new lessons to be learned and my approach will continue to evolve over time. 

Coming up - lessons learned in the sugar world.

Thursday, September 23, 2010

The Last Hurrah - Part 8

Part 8 - "Goodbye My Lover"

After the waves washed away the heart in the sand, we went back to our room and started packing. She wanted to go back to town and buy some knock off name brand handbags for her friends and family. So we made a stop on the way to the airport for her to browse the street vendors one more time. It took a while for her to finally pick out what she wanted to get. She was especially happy with a black Chanel handbag and wallet she got for her mom, saying that she will put $1k cash in it and give it to her for Christmas. Only if her mom knew where the money came from! she also got a few tropical clothing items and got her hair braided.

By now we're cutting it close so we headed to the airport. While at the airport I told her there are a few shots left in the disposable camera and I'd like to take some shots before we get on the plane. It's a small airport and there is no jet bridge, so we actually have to go on the tarmac and take a stair to get on the plane. While we were out on the tarmac I took a picture of her in front of the plane with the mountains in the background. And then I asked another passenger to take a picture of us together. When he gave the camera back to me she tried to grab it but I took it from her and put it in my briefcase.

During the flight to Miami she slept for a bit, and when she woke up she asked me to send the pics to her when I get them developed. I told her I'll think about it. I also told her that I made a slideshow using the pics I took of her previously and I also have pics of some of the women I've been with. So naturally she wanted to see them. While looking through the pics she didn't say much other than that they are very pretty. Then I showed her the slide show made of her pics with captions of things she said to me in the past, set to the music of "And Then We Kiss" by Britney Spears which is one of her favorite songs. The slide show posed the question "Who is the real Laine?" and it went through a series of pics and captions that showed her as a "Sweet, caring, hard working girl next door", "Selfish, game playing, drama queen", and "Greedy, demanding, high priced escort." As she watched the slideshow I reminded her of the sweet things she used to say to me and the way things were in the beginning. She didn't show much reaction but I'm sure I got my point across.

After we got to Miami we hang out in the airline lounge to wait for our next flight. This is when she told me that she has picked "Goodbye My Lover" by James Blunt to be "our song". And she sang a couple of lines from the chorus "Goodbye my lover, goodbye my friend". I didn't know the song so I didn't know what it was about, but thought it strange that she would pick a song with that title.  She also said that it was good to have "closure" between us, which took me by surprise she would say things like that. Who needs "closure" when it's all about money? When it's time for me to board my flight, she walked me to the gate and we hugged and she kissed me on both cheeks and said goodbye, then walked away. And just like that she was out of my life. Or was she?

Well, she still gets the last laugh. After I got home I found two surprises. The first one is that she stole the disposable camera from my brief case. I'm not sure if she thought it was a harmless prank or there was something more sinister to it. That's why I have no pictures from the trip and I know I took some pretty good ones. The second surprise was the lyrics from the song which I have copied below. Why drew the heart in the sand and share such an emotional song with me on our last day?

She was playing games until the very end. That's just how she is, that's the real Laine.

The end?
-------------------------

"Goodbye My Lover" by James Blunt


Did I disappoint you or let you down?
Should I be feeling guilty or let the judges frown?
'Cause I saw the end before we'd begun,
Yes I saw you were blinded and I knew I had won.


So I took what's mine by eternal right.
Took your soul out into the night.
It may be over but it won't stop there,
I am here for you if you'd only care.
 

You touched my heart you touched my soul.
You changed my life and all my goals.
And love is blind and that I knew when,
My heart was blinded by you.


I've kissed your lips and held your head.
Shared your dreams and shared your bed.
I know you well, I know your smell.
I've been addicted to you.

Goodbye my lover.

Goodbye my friend.
You have been the one.
You have been the one for me.

I am a dreamer but when I wake,

You can't break my spirit - it's my dreams you take.
And as you move on, remember me,
Remember us and all we used to be


I've seen you cry, I've seen you smile.
I've watched you sleeping for a while.
I'd be the father of your child.
I'd spend a lifetime with you.


I know your fears and you know mine.
We've had our doubts but now we're fine,
And I love you, I swear that's true.
I cannot live without you.

Goodbye my lover.

Goodbye my friend.
You have been the one.
You have been the one for me.

And I still hold your hand in mine.

In mine when I'm asleep.
And I will bear my soul in time,
When I'm kneeling at your feet.

Goodbye my lover.

Goodbye my friend.
You have been the one.
You have been the one for me.
I'm so hollow, baby, I'm so hollow.
I'm so, I'm so, I'm so hollow. 


I still get goose bumps and think of her every time I hear this song.

Tuesday, September 21, 2010

The Last Hurrah - Part 7

Part 7 - The Heart in the Sand

As we continued "the talk", she explained that when I first met her I was at the right place at the right time. She just broke up with her long term SD/BF and started to work 6 days a week. She didn't have a lot of free time and I was willing to go visit her and work around her schedule. She didn't have that many people to talk to so that's why we spent all those hours on the phone. And I'd admit that in a way I did take advantage of the situation and I'm surprised at how long it lasted. But over time she became frustrated because she wasn't getting as much as what her escort friends were getting and she knew she could get more by dabbling as an escort. That blew up after three months when we broke up over a big fight because she thought by being so mean to me we'd both move on.

But to her surprise I came back to her, and she thought if she could continue to be mean to me and still get money from me, then why not. I knew going back to her like that was a mistake, and that's why she told me earlier that she treated me that way because I let her. So in a way it's my own doing and I have no one to blame but myself. I asked her if it was all a game from the beginning, and she said it didn't start out that way but things changed over time. Yeah, things changed, but I didn't.

After that long talk it seems that we were both relieved to get it off our chest. So I started my pussy eating routine again and... By now it was really late and we cuddled and slept in each other's arms knowing that it was our last night together.

On our final day things almost felt like it was back to the good old days. We both got things off our chest and laid it out in the open. Although I'm sure she hasn't told me everything and I didn't like what she had to say, I have heard enough to be content. After our morning routine of a romp in the sack followed by breakfast, we went to the beach one last time. As usual she was frolicking in the water and having a great time while I played along.

We almost got it on again but she wouldn't let me do it this time because there were too many people at the beach. After a while we both lied on the beach just letting the waves crashing into us and playing with the sand. This is when she drew a heart in the sand with our initials in it. I looked into her eyes and asked her why she did that, and before she could answer a wave came and washed it away. And just like that the "moment" was gone....

Coming up - "Goodbye my lover"

Sunday, September 19, 2010

The Last Hurrah - Part 6

Part 6 - The Talk

We spent the rest of the afternoon at the beach and I'd say that was the highlight of the trip. On the way back we had dinner at a restaurant by the dock and we talked some more before taking the ferry back. I can never be sure whether to take 100% of what she says seriously, but the conversations we had the rest of the day was probably a good indication of what type of person she had become. She asked me several times why I hate her so much, and I told her that after everything she had done to me it should be pretty obvious so she should stop asking. Then she said is it because she is a conniving bitch and I said that's pretty close.

She talked about her new approach to sugar relationship which is more like a stripper/escort approach. That is, to get the most out of a guy and then move on to the next one. Obviously she has gotten what she wanted out of me and she has moved on. She also talked about how to make the new guys fall for her so she can have them in the palm of her hands. I told her she is a "player" and you don't play with a player. And she is playing with fire so sooner or later she will get burned. She mentioned that she has to act "normal" around her new guys. I told her that she is not normal and she only "acts" normal, and that's one thing she is going to miss about me because she can be herself around me.

Prior to the trip she had talked about wanting to "re-negotiate" our arrangement so I asked what that was about. She said her goal is to get $2k a day from the guys that she sees because that's what her escort friends are getting. So surely she should be able get the same or more. I asked her if she has gotten that from anyone yet and she said no. She then said if her new guys can't pony up $2k a day for her then she will just move on. OK, keep digging for the gold! I told her that's another reason why I'm done seeing her, because to me a sugar relationship should be more than just how much money she gets by the hour or day.

By the time we got back to the hotel we were both exhausted so we cleaned up and took a nap until late in the evening. Once we woke up we started our "talk" again. I told her to be careful with what she is doing and who she is doing it with. I'm a nice guy and I'll get over what she did to me, but the next guy may not be so forgiving. I also mentioned some of the women I've been with recently to let her know that I'm moving on as well. And I gave her tips on where her new guys should be taking her, telling her about my past trips to various fun places. I think that opened her eyes a bit and let her know that I'm not as dumb and gullible to her games as it seemed.

I also told her that I kept a journal of our meetings and it certainly got her curiosity going. So I read to her what I wrote about her from the first few meetings. As I read it to her, I reminded her of how things used to be and how she came across to me which is nothing like she is now. She went from a sweet, caring, hard working girl-next-door, to a greedy, demanding, high priced escort and drama queen. She got a bit defensive and gave me her version of what happened in the early days.

Coming up - The Heart in the Sand

Friday, September 17, 2010

The Last Hurrah - Part 5

Part 5 - Sex on the Beach

After three rounds of sex on the second day, I figured I'm finally getting what I want out of her so the trip wasn't a total loss after all. But quite frankly the sexual dynamics have changed. What used to feel like girlfriend sex, whether real or imagined, now feels more like escort sex. The difference is very subtle and the sex is still good, but it's not great and will never be again. Having said that, I woke up next morning horny as hell so I went under the sheets and started to kiss and lick her bottom and legs again and slowly worked my tongue towards her pussy. Since this is the one thing she said she likes about me, I figured I'll just keep at it for as long as I can. Soon she was fully awake dripping wet and ready to go...

After that we got dressed and went down stairs for a leisurely breakfast and talked about what we wanted to do for the day. She mentioned that she wanted to go para sailing, ride a wave runner, or snorkeling. I told her jokingly as long as she picks up the tab she can do whatever she wants and I'll go with her. She gave me a dirty look and then said she just wanted to do one of the three things so she is not that demanding. Then I said fine, we'll go snorkeling at a nearby island since it's the cheapest! LOL... Actually she had told her "munchkin" about the trip and he suggested that she should go snorkeling there because it's one of the most beautiful beaches in the world. I told her that's true since I've been there before, I also told her it's the third time I've been here. Then she was asking repeatedly who I was there with before, and I just gave her a knowing smile without saying anything.

We got dressed and took a taxi to the ferry around noon. It was a short 15-20 minute boat ride and we were enjoying the views along the way. When we got there I asked her if it was the most beautiful beach she's ever seen or what... pure white soft sandy beach, warm turquoise water, and a rock formation in the distance that is teeming with sea life. We got our snorkeling gears and spent a couple of hours swimming around the rock formation. We saw schools of bright fluorescent blue and yellow fishes and came upon thousands of silvery minnows gleaming in the water. It's quite a sight to see these little things swarm around you and suddenly change directions as a group. After all that time in the water I was tired and went back on the beach to rest. She seems to really enjoy being in the water and she stayed in it to play by herself for quite a while after snorkeling. Then I thought I'd join her so I grabbed the disposable camera and asked her to pose in various positions in the water and on the beach and took several shots. She looked very hot and she posed like she knew it!

After taking pictures I was carrying her in the shallow water walking from one end of the beach to another. As we got to the end of the beach there was a secluded area behind some rocks and we lied there and talked for a while and then got in the water again to play. One thing led to the other and she can feel my hard on pressing against her pelvis as she put her arms around my neck and wrapped her legs around my waist. Just as we were about to get it on she noticed the life guard walking towards us so we played it cool until he went away. I guess he just wanted to make sure that we weren't doing anything we were not supposed to do. Anyway, she wrapped her legs around me again and.... Doing it in salt waster wasn't the most comfortable nor the most pleasant, but it sure was thrilling and got our adrenaline going. Carrying her in the water and fucking her at the same time took some coordination on my part, but soon we got into a rhythm and we were both enjoying this little escapade in paradise... and then we both lied down on the beach to catch our breath.

Coming up - The Talk.

Wednesday, September 15, 2010

The Last Hurrah - Part 4

Part 4 - The Munchkin

One thing that pissed her off about the munchkin was that he was taking her to dinner to meet some friends, and he was going to buy the same exact dress for her to wear as for another girl he took to dinner to meet the same friends the week before. I just laughed and told her to get used to being one of many. I also said that's one of the reasons why I'm done seeing her because I don't want to be one of many. Some guys might be ok with that, but I'm not. She said she started to drink because of him, he likes to order lots of expensive wine and drinks every time they go out so she might as well take advantage of it. I told her she is turning into a lush! LOL...

Then I asked her why she calls him "munchkin" and she didn't really want to say, but finally blurted out that he is much older than her and short and round like a munchkin. I told her nobody will ever mistaken them for boyfriends and girlfriends like when I'm with her, and she is clearly a "paid companion" when she is with him. Ok... so her love of money is stronger than I expected but why am I not surprised.

After listening to her complaining about the munchkin we decided to go back to the room to clean up and get ready to go into town. We took a shower together and I told her we hadn't done that in months, and other than sex it was the most sensual thing we did together during the trip. After the shower I got her on the bed, spread her legs and started to eat her pussy and suck her clit. It's been a while since I made her cum with oral and I was determined to do it again since she told me I was the only one that could.

She was clearly enjoying what I was doing and started to moan softly and held my hands tight. After a while I quickened the pace and put my fingers in her to rub the g-spot and she started to gyrate her hips up and down and from side to side. I kept pace with her gyration and I can feel her pussy start to tighten around my fingers and it didn't take long for her to shudder uncontrollably, squeezed her legs tight around my head and begged me to stop. Then she said this is the one thing that she is going to miss about me. I guess I'll take that as a compliment! After that she returnd the favor and took good care of me and made sure my needs were met.

After we rested for a while we took a hotel boat into town. The town is famous for its duty free shopping, but as we walked around she wasn't all that interested in the fancy jewelry and designer clothing shops. She was actually more interested in the street vendors under the tents selling knock off name brand handbags. She took a lot of time going through each stand and figuring out what she wants to get for her family and friends. After a couple hours of browsing she didn't end up buying anything so we went back to the hotel and took a nap.  After the nap we went down stairs to have dinner at the restaurant by the pool. She did her hair and make up and looked stunning even though she wasn't dressed up.

During dinner we talked about her exploits again and this time I was trying to explain why I thought what she did when she came to see me was so evil. After some back and forth I think she was able to see my point of view but she didn't apologize. Anyway, we had a nice dinner and then took a walk along the beach under the stars holding hands and dipping our toes in the water. As we held each other tight and looking up at the stars I thought this is supposed to be the stuff dreams are made of, but now I know it's just an illusion.

Back in the room I undressed her and got her in a 69 position with her on top. This went on for a while and I was able to bring her close several times but she couldn't quite get to the big "O". So she told me to fuck her and I proceeded to do it in multiple positions. After that I sensed she was not quite done yet, so I started to eat her pussy again and this time was able to bring her to the big "O" quickly and it was much more intense than earlier. After we cleaned up we crashed on the bed in each other's arms. So consider how the first night ended, the second day went much better. The sex was good but not as great as it used to be, and it will ever be the same again.

Coming up - sex on the beach!

Monday, September 13, 2010

The Last Hurrah - Part 3

Part 3 - A New Day

I wasn't expecting much on the second day after we ended up sleeping separately the night before. Even though I was tired I didn't sleep very well. She was all covered up and didn't move much and was quiet through the night sleeping on the lounge chair. I got up before sunrise and went out on the balcony to enjoy the view. Our room overlooks the Caribbean and the harbor where cruise ships dock. As the sun came up the view was spectacular and I enjoyed my moment of solitude in paradise.

Then I thought, despite what happened so far I'm going to make the best of it and get what I can out of her. So I went back in the room to wake her up by removing her cover and squeezing myself on the lounge chair with her. She slept in the nude but told me to go away, so I just started to kiss and lick her bottom and legs. After a while I got her warmed up pretty good and ready to go. But then she said we're not having sex because we're enemies. To which I replied "it's just business, don't take it personal." That's a line she used on me before so I'm just returning the favor. Finally she relented and I took out a bottle of lube to get started. She took a look at it and said this thing is already opened and what did I use it for. I just gave her a knowing wink and left it at that. Anyway, the sex was very satisfying and I can see why she had no problem getting top dollars doing her "escorting" on the side.

After that we got dressed and got ready to have breakfast on the terrace that overlooks the harbor. But as we went through our luggage we discovered that the Chanel sunglasses I got her was stolen, and my digital camera was missing. I guess the luggage screeners swiped the most expensive things from our luggage! Undaunted, we went down to the gift shop to get her new sunglasses and I got a disposable camera to take pictures (more about the camera later).

When we got to breakfast two cruise ships have arrived and it was quite a sight in the harbor. We enjoyed the food and the view leisurely and then headed to the beach. She was very playful in the water, pretending to be a mermaid and singing songs from the movie Little Mermaid. I think she really enjoys the water and the sand and was having a great time. On the beach she told me to dig a hole for her and cover her up in the sand with only her head sticking out. I did that and then used the sand to make two huge boobs to put on top of her and left her there. It was hilarious to look at and people walking by were doing double takes, and of course I took a few pictures.

By now the sun was getting very strong so we decided to retreat to the pool and hang out under the shade. She wanted something to drink so I got her a daiquiri from the bar and asked her when did she start drinking because she rarely drank when she was with me. This is when she told me a lot more about her "new guy" who she nicknamed the "munchkin". They first met when he was in her town for business and spent an overnight together. The second time was a week before our Caribbean trip when he flew her out to LA for 2 nights.

From what she said this guy is clearly loaded. He stayed at the most expensive hotels and the hotel bathrobe had his monogram on it. He sends her a car service to take her to/from the airport. In addition to the cash she also got gifts and went shopping. He flew her first class and in LA they stayed at the villas in the Peninsula which is not too shabby. But clearly she is just one of many girls he sees but it doesn't bother her as long as the money was right. He even showed her pics of other girls he was seeing and asked her about being exclusive. So she was trying to figure out a good number to ask for to be exclusive. I told her it won't matter what she comes up with because she is not going to be exclusive with anyone for any price. That's just not in her.

Coming up, more about the munchkin.

Friday, September 10, 2010

The Last Hurrah - Part 2

Part 2 - Being Evil

When we finally got to our destination we were both exhausted. We stayed at a posh resort on a cliff that overlooks the Caribbean and I got a suite on the top floor with a balcony. We couldn't see much at night but I knew the views would be breathtaking during the day. She wasted no time getting into her bikinis wanting to go check out the beach in the dark. So off we went and played in the water late at night when no one else was around. We were really enjoying ourselves on the secluded beach and floating in the warm water looking up at the stars above. It was very romantic and we held hands and held each other tight. After a while we decided to go to the pool and eventually ended up at the hot tub. This is where we picked up our conversation again about her exploits and things took a turn for the worse.

We talked about the guy she met in the same city as me and she came clean about what happened. She came to visit me twice and both times she insisted on buying her own airline ticket. When she bought her own ticket I usually make up for it by shopping and gifts. After the first visit I was surprised that she wanted to come back again two weeks later. I even offered to visit her instead but she insisted that she will come see me. But this time right before the trip she asked me to send her money to help pay for the ticket. Actually it was more like a threat as in she won't come if I didn't send her the money even though she was the one that insisted to come see me in the first place. Anyway, I sent her the money because she said she bought the ticket last minute and it was going to cost more than normal.

When she arrived she said she packed in a hurry and just threw in a bunch a stuff in her luggage which was probably more than she needs. Hmmmm, ok. On the morning of her departure she spent quite some time putting on make up and doing her hair which I thought was odd for that early in the morning. When I took her to the airport she told me not to come in. But I insisted and walked her into the terminal, then she got very upset so I just left. I'm sure you know where I'm going with this. On that trip she met another guy for money after I dropped her off at the airport! He didn't want to pay for her ticket so she tricked me into paying for it. How low was that?

But that's not the worst part. The worst part was that she didn't see nothing wrong with what she did. She said if I paid for the ticket for her to come out, what difference does it make that she ended up staying an extra day with another guy for money (as if, what's the big deal if I wasn't the one getting sloppy seconds?). At this point I've had enough and told her to fuck off and called her "evil". Then I got out of the hot tub to walk back to the room. Not wanting to be locked out, she followed me closely back to the room. I took a shower and when I came out she had a made a bed out of the lounge chair and covered herself up under a blanket. Without saying a word I went to sleep on the bed thinking what the fuck am I doing here. What a way to start the trip!!

Coming up, Part 3 - A New Day

Wednesday, September 8, 2010

The Last Hurrah - Part 1

Part 1 - An Ominous Beginning

I called the Caribbean trip our grand finale, "Laine" (not her real name) called it our Last Hurrah. Whatever it's called, it was a trip to be remembered.

Prior to the trip she had never missed a flight or a meeting in six months, but I guess there is a first time for everything. I talked to her the night of her departure for about an hour while she was packing and we hung up about two hours before her redeye flight to meet me. At around 2am she called to tell me that she is cutting it too close, she just parked her car and waiting for the shuttle to the terminal. About 15 minutes later I got the bad news, the check-in counter was officially closed and they wouldn't let her on the flight.

She offered to give me a "refund" and not go on the trip, but I had put too much money and effort into it to just give up. I told her to go home and I'll call her back with our options. After spending some time with the airline on the phone, I was able to rebook her for a morning flight to Miami and I changed my flights to meet her there. We'll still get to the destination on the same day but 7 hours later than planned at 10pm instead of 3pm. Needless to say I didn't get any sleep at all because I had my flight to catch early in the morning and I had to wait four hours for her to arrive in Miami.

By the time she arrived in Miami I wasn't in the best of mood for many reasons. We talked but she can sense that I was kind of cold and distant. But once we got on the flight to San Juan she was being her usual self, playful and funny, and we had some enjoyable moments. But as always we went from enjoying each other's company to being at each other's throat in no time. By the time we got to San Juan and waiting for the next flight we weren't talking again.

My original plan was to play dumb for a few days and then confront her on the last day with all the games she played on me in the past. But it didn't quite work out that way. Prior to the trip we had talked only twice on the phone in two weeks which was far less often than how things used to be. She mentioned the week before the trip she was going to be busy because there were several guys wanting to see her. To make a long story short, on our way there she told me about several more guys that she was seeing for money, including someone in the same city as me and her "new guy" which is her new SD that appeared to be loaded (more about both of them later).

Basically the extent of her "escorting" on the side was far greater than I could have imagined. She had gone from a hard working person who worked six days a week, to quitting her day job to spend more time on "escorting". Clearly she wasn't the same person I met six months ago. I originally found her on sugardaddie.com, but now she has a profile on a site called "SeekingArrangement" and that's where she met her new SD. Apparently her escort friends told her about it and they're all having a lot of luck with that site. I had already found her profile there so it wasn't a big surprise to me.

Coming up, being evil...

Tuesday, September 7, 2010

The Last Hurrah - Prolog

When you read "The Last Hurrah" it will feel like watching the end of a soap opera without knowing how it started and what had happened over time.  The story is about how I broke up with a former SB during a trip to the Caribbean after a drama filled six month relationship.

Did I know it was going to be "The Last Hurrah" before the trip? Yes we knew and we mutually agreed to end it this way. I prefer to go out on top instead of breaking up after a big fight, but it still ended in a train wreck anyway. The truth is, prior to the trip I found out more about her games through old fashioned sleuth work. And I totally underestimated the lies and deception that went on. I can't say that I was shocked because there were plenty of clues and in some ways it merely re-enforced what I suspected and what I already knew.

But I was in denial until the very end.

In this particular case, my former SB used "sex" to play many mind games with me to her advantage. Leaving out the sexual content in the context of the story would be like telling only half the story.  So this is a story of sex, lies, deception, and betrayal. Stop reading now if you are offended by tmi, sexual content, adult situation, and strong language.  Keep in mind the usual disclaimers apply.  I will do my best to keep things in good taste but I know it will not please everyone. 

Maybe someday I'll go back and fill in the blanks and make this a complete story from beginning to end. But for now I hope you'll enjoy reading "The Last Hurrah".

Friday, September 3, 2010

Evolution of a Sugardaddy - Part 6

Part 6 - Getting emotionally involved for the last time

The story of "Mixing Love and Sugar" set me back emotionally for quite a while but eventually I got over it and moved on.  But it still didn't prepare me for what happened a year later.  My second "long term" SB was in her mid twenty's at the time and it was a long distance relationship.  We met about twice a month for six months. During the first three months it was a combination of allowance and gifts, but after that she became more interested in having a steady allowance so for the next three months I went to an allowance only arrangement. It was the first time that I provided an on-going allowance and it marked a turning point in my thinking as I gradually went away from the gift/travel aspect and focused more on allowance only.

After a great start where she behaved more like a caring and loving girlfriend who was genuinely interested in me as a person, the relationship became full of drama and spiraled out of control and I had to end it during a trip to the Caribbean. She turned out to be a conniving, manipulative drama queen and an escort wannabe who was looking for the highest bidder.  Why I didn't see the train wreck coming was beyond me, and I should have heeded the advice of others and ended it sooner.  I'll write about the story of our breakup titled "The Last Hurrah" next.

Another turning point in my thinking was that I completely gave up on the "emotional involvement" aspect of being a SD.  I was not very good at making things last long term at the time (ie more than 6 months) nor being able to handle the emotional attachment when it develops.  So why make it harder on myself and be miserable when I should just focus on having fun and enjoy the NSA aspect of a sugar relationship.

At about this time sugar dating started to become part of popular culture with plenty of exposure in the main stream media. And the popularity of sugardaddy dating sites increased dramatically with a huge number of new members signing up every day.  As a result, I stopped searching all over the country and fly in potential SB's for a first meeting because of the costs and risks involved as I have explained previously.  Instead, I focused on searching locally and at the places I travel to regularly for business. With an abundance of new pot SB's available I had to narrow my demographic criteria to make the search more manageable.  Then as sugardaddie.com evolved into more of a regular dating site, I transitioned to seekingarrangement.com when it came on the scene and it would eventually become my primary source to search for pot SB's.

Coming up - Where I am today

Wednesday, September 1, 2010

Mixing Love and Sugar - Part 9

Part 9 - Life Goes On

"You shall know the truth, and the truth shall set you free." That's how I felt when I finally pieced together all the information I had and got to the bottom of the rabbit hole. Although I felt liberated and motivated to move on, I can't help but think about how the experience has affected me as a person and the way I approached my next sugar relationship.

I appreciated all the support, opinion, and advice I received from several SD/SB "friends". Of course they all told me to put her out of my mind and move on. But it wasn't that simple. She, or more accurately the idea of her, was still on my mind subconsciously. I found myself comparing every pot SB I met to her since I still had a picture of her as the prefect SB in my mind.  

This of course was unfair to the pot SB's I met and unfair to myself because the person I thought I knew never really existed.

One of my SD friends asked me some probing questions. "Had you known she was doing this, would you have felt the same way about her?" Well, of course not. Had I known that it was all a game to her, I would have played along and never fell for her. "If you had found out what's really going on, would that have changed the outcome?" Probably not, because the outcome wasn't really in my control.

She was playing her game and I was just a piece of the puzzle or a bump on the road to her.

Then he had some words of wisdom for me. He said that I needed to change my opinion of her because the perfect image that I created in my mind never existed. I need to see her as who she really was, a ruthless "player" who used and manipulated men for her own goals. She was seeing three SD's at the same time and made each one believe that he was the only one for her and made them fall for her. She was a habitual liar and concocted an elaborate alternate reality for those around her. She was incapable of telling the truth to deal with reality.

She had some real issues that she needed to deal with herself.

Until I truly get over her, I will not find what I was looking for because I was focused on the shortcomings of the pot SB's I met and comparing them to someone who doesn't exist. Instead, I should focus on the strengths and weaknesses of the pot SBs and evaluate them on their own merit.  Those words of wisdom may sound like common sense, but it was a revelation for me at the time. Even though I thought I had moved on by finding out the truth, the fact is that I hadn't. I still had happy memories of my time together with her and the sweet things she said to me.

I finally had to find a way to look deep within myself and admit those memories don't really exist.

In the mean time, life goes on.

The end.

Sunday, August 29, 2010

Mixing Love and Sugar - Part 8

Part 8 - Going down the rabbit hole

What she told me about her work, trips, and the situation with her husband were not true. She was not new to the site and it was not the first time she has done this. I was still not clear of her motives, but she seems to enjoy making men fall for her and then move on, while having the security of a husband to go back to.

Well, her "work", as it turned out, was with a local SD who was in the financial field. It started at the beginning of that year when she used a different profile. The trips to NY and LA were with him and apparently he fell for her as well. When she contacted me her relationship with him was coming to an end unbeknown to him.

After our trip to Seattle she got in contact with another SD, and the Vegas trip was with him. After our trip to Chicago she made up the story about her husband finding out to get rid of me and moved on to the new SD. In the mean time her husband was probably still in the dark and having an affair of his own. Actually I kind of felt sorry for her poor husband if there really was one. Whoever she moved on with was in for a big surprise if the pattern continues.

I had found out a lot of this on my own, but the break through came when I met a pot SB and told her briefly about my heartbreaking story.  To my surprise, she said she had met a pot SD who told her a very similar story!!  It didn't take long before I put the pieces together and got in touch with the first SD, and we both decided to compare notes and went down the rabbit hole to see where it leads.  Her first SD was a lot older than her, and apparently he was a lot more generous to her financially.  Was she only with him for his money?  Did I happen to be her Mr Big?  Why did she ditch both of us and moved on to the third SD?

She played me like a fool and I didn't even know it at the time.  Falling for her was clearly not a smart thing to do, but she seemed to enjoy the game of making men fall for her and then move on. Now that she has done this more than once, she knows with her beauty and charm she can seek out any man she wants and make him give her whatever she wants, emotionally and financially. And lots of men will gladly trip over each other to be with her without knowing what's coming.

The truth has set me free. Or has it? How will the experience affect me as a person and as a SD? How will it affect the way I approach my next sugar relationship?

Coming up, the conclusion... life goes on.

Thursday, August 26, 2010

Mixing Love and Sugar - Part 7

Part 7 - What Really Happened?

The last email from her caught me completely off guard. I can't believe how someone so close to me just a few weeks ago could become so cold and heartless so quickly. I had more questions than answers. But instead of moving on, I was determined to go down the rabbit hole to find the pieces and figure out what might have really happened.

As I mentioned before, there were things she told me about herself and her work that didn't seem quite right. But I chose to ignore them and enjoyed our time together instead. Now I need to retrace the steps and see what warning signs I might have missed.

When I asked her about her work in the beginning, this was her response:

"I am looking for someone who is successful and can potentially travel with me. I do part-time consulting for an organization that holds seminars and conferences around the nation. For this reason I usually end up traveling at least once or twice a month. This aspect would make it easy for me to get away without my husband thinking twice about my reasons for being gone."

When I talked to her more about her work, she said the conferences are in the financial field and she works for an older couple that owns the business but mainly with the lady. She described her work as administrative and like a personal assistant to the older lady. She found this job at the beginning of the year and she traveled to NY and LA for work before she met me. When I asked about her travels she said she flies first class and stays at five star hotels. Sounds like a pretty good job! When I asked her if I can join her during one of her business trips, she said it's not a good idea because she spends a lot time with her boss at dinners and social functions. This is contrary to what she said about looking for someone who can travel with her. She continued to use her "work" as an excuse with her husband when she was meeting with me.

She also told me about a trip she took to Vegas a couple of weeks before we went to Chicago. It was supposed to be a fun trip with her girlfriends. She mentioned that she had won a jackpot and bought herself a very expensive watch with it. Lucky her! She showed me the watch and it was very nice.

When she first wrote to me I was surprised that she was very savvy about meeting people from the internet even though she said she was new to it. In fact she wrote to me the same day she created her profile. And yet she seemed to already know there are many scammers, flakes, and time wasters to sort through on that site.

After weeks of reflection, putting together the pieces, talking to other SD/SB's, and some old fashioned sleuth work, I think I have finally figured out what really happened. It actually feels liberating to finally know the truth, it's a way for me to find closure on my own and move on.

Coming up - Going down the rabbit hole

Tuesday, August 24, 2010

Mixing Love and Sugar - Part 6

Part 6 - What's wrong with this picture?

I read her letter many times and reflected on the great times we had. It was a thoughtful letter with lots of details and she clearly wanted to end things on good terms. I wrote back to her to express my disappointment and sadness, and to let her know that I respected her decision. But I didn't get a response from her which is not unexpected, even though she said she wants to hear back from me and stay in touch.

I should have taken everything at face value and moved on because it's for the best, right?

But then I noticed that she was back on the site for several days in a row. Why would she do that if she is really trying to make things work with her husband? Also, I'd have expected that her husband would have closed her email account and changed her number, but they seem to work fine. Sensing there might be something wrong with this picture, I emailed and called her several times to seek an explanation so I can have some closure, but they were all ignored. 

Then a few days later I got this little gem from her by email:

I have been careful to not share too much with you about my life, my job, etc. In a relationship such as we had, it is difficult to know where it will lead and what will happen. I have had a history with "stalker" type personalities and my mother has always taught me not to share too much information with someone you have not known for long.

My husband is well aware of you and your recent emails and calls to me. I have nothing to hide and my husband and I are very concerned with the behavior and persistence you have shown in your recent emails and phone calls. We do not want to have to pursue a restraining order if your emails and phone calls continue to be persistent and threatening in nature. I have informed you that I no longer care to see you and we really wish that you could accept that and move on peacefully with no further contact attempts.


My husband and I are in this together and anything you share with me from this point forward (emails and voicemails) will be viewed and shared with my husband. I hope that we can part on good terms and that you can be respectful of the situation and the conclusion of our "relationship".


OUCH!! Put that dagger through my heart!

I suppose my attempts to contact her could be perceived as threatening... but to pursue a restraining order?? And parting on good terms meant concluding our "relationship" with no further contact attempts?? I was completely shocked that someone so close to me just a few weeks ago could become so cold and heartless so quickly. I thought I have been around long enough but I was still completely blindsided by the turn of events.

Then I was thinking.... could she have made up the whole thing with her husband finding out just to get rid of me? Did she have an affair with me because she suspected that her husband was having one too, and I happen to be the one she came across? Why did she do this to me? Why say all the right things and then break my heart? Was any of it for real??????   

I had more questions than answers and I was completely at a loss as to what might have really happened.

Coming up, what really happened?

Friday, August 20, 2010

Mixing Love and Sugar - Part 5

Part 5 - The Dear John Letter

After I got back from Chicago I couldn't be any happier and I was really looking forward to our next trip to the Caribbean. Then she dropped a bomb on me three days after we said our goodbyes in Chicago.

She sent me a "Dear John" letter to let me know that her husband found out about the affair. Even though she said she is not in a happy marriage, they decided to reconcile and make it work. She won't be able to see me or contact me anymore because her husband will keep a close eye on her activities such as her email and cell phone calls. Keep in mind that she had told me this is the second affair she had in her marriage, and the first started shortly after she got married. She said she found out her husband was also having an affair when she was seeing me. I can't believe they would want to stay together and make the effort given the history of their infidelity.

For a few days my head was in a fog and I couldn't eat or sleep. I felt disappointed, sad, upset, angry, and hurt. I can't believe how something so wonderful could have ended so suddenly. But even though she broke my heart, I thought it might be for the best and I should respect her decision and support her effort to make her marriage work.

Here are excerpts from her "Dear John" letter:

To make a long story short....... hubby got home early while I was still out, jumped on the computer to check his e-mails AND found my email account. So you can imagine how horrible it was when I got home. Fortunately he did not have much time to read my emails from you..... but he now knows about Chicago, Seattle, and my next trip with you!!!!

So in a nut shell, last night was filled with tears, anger, sadness, yelling, arguing, and then finally some rational talk at the end. He admitted to me that he had begun seeing someone. Apparently, they have been sexually active and dating for the past 3.5 months! Not a complete shock to me, but definitely hard to take.

Once we were able to rationally speak to one another we actually had a good talk. We discussed separation, but to be honest with you, we both get very sad at the idea of parting ways. We determined that we would give this marriage a whole-hearted shot and try to work things out. This of course is sad for me, because I know that it means no longer speaking with you. This is very hard for me to do, but I know that my husband deserves one last perfect attempt at saving our marriage. I'm sure this is all coming as a shock to you, but I believe it is what I want to try to do. We are both a little crazy for trying to give this another shot, but I think it is worth a try."

I hope that you can understand my decision to give my marriage a devoted attempt. I cannot begin to tell you how much I have enjoyed our time together and the way you made me feel. If the circumstances were different, I would love to explore where our relationship would go. I hope this does not come as a complete shock to you, although I'm sure it is not the e-mail message you wanted to receive in your inbox. I changed my e-mail password, so hopefully I can at least communicate with you via e-mail and get your feedback."

I am nervous to hear back from you...... but I hope that you can respect the direction my situation is headed in. We plan on attending a couples retreat for marriage counseling. Thank you for all the joys you have given me. If this last attempt with my husband does not work out, you will be the first one to know.

Keep smiling and keep in touch, ok?

Love,


Coming up - What's wrong with this picture?