Diary of a Sugar Baby

These are the secrets, confessions, and thoughts of a modern day paramour.

To Escort or Not to Escort, That is the Question May 25, 2008

Filed under: Musings,SugarDaddies — AllieSugarBaby @ 7:16 am
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In the brief time that I’ve had a profile on a couple of online sugardaddy dating sites, I’ve gotten a number of very interesting emails.  Some have been very forward – essentially seeing me as nothing more than a prostitute who should be willing to give a man sex in exchange for money.  Others have been more subtle, but the intent was still clear – sex for money.

However, I got an email this morning – don’t ask why I’m up so early, I’ll talk about that later – that has me really thinking about whether or not a side job as a very high class escort would really be so bad.  The email wasn’t from one of the usual men, this was actually from a business telling me that they often have very wealthy clients who want upscale, attractive young women for companionship when they are in town.  No mention of sex, stripping, dancing, or anything like that.  Just companionship in exchange for as much as $2,000 for an evening.

I have to admit, this email made me stop and think…  Could this be a potential way to meet my favorite type of sugardaddy?  My favorite type of sugar daddy is the wealthy businessman that travels and wants a “Barbie Doll” to accompany him on trips and whenever he’s in town.  It’s clear that these men wouldn’t be local, so they have to be traveling to my area…

I’m thinking about it, but will I do it?  I emailed them back to ask for more information and to set up a meeting to discuss in more detail.

What do you think?


Where to Meet a Sugardaddy: Hotel Bar May 21, 2008

Filed under: Places to Meet,SugarDaddies — AllieSugarBaby @ 7:56 pm
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So, Ladies, you want to meet a Sugar Daddy of your own?  Not sure where to meet him?  I’m going to do a series of posts talking a little about some of my favorite places to meet potential Sugar Daddies.

What sort of places are you likely to find those successful, mature men that want an attractive, young lady to spend time with?

One of my favorites is the hotel bar.  No, I’m not talking about the bar at your local Hilton or Marriott.  Sure, you’re going to find some male business travelers at these places, but they’re usually going to be traveling salesmen, junior executives, or just a businessman in town for some sort of training.

What you want is the hotel bar at the best hotels in your city…  Where do the wealthiest people stay when they visit?  Where does a CEO stay when he’s in town for a conference or meeting?  That’s the spot you want.  What you’re looking for at a hotel bar is the highly successful traveling businessman who wants a companion when he’s in town.  Make yourself very clear that you are not an escort – make him earn it before he finds out what you have on (or not) under your dress.  However, since the gentlemen you’ll meet in this environment are not going to be the men you’ll see every week or even every month, so you want to get the gifts coming quickly and you need to get him thinking about you quickly.  The wonderful thing about this type of sugar daddy is that you know he travels – the type that may want to give you a first class ticket to meet him for a long weekend after a business trip or who will jet in and lavish you with gifts and money for a few days before leaving you plenty of time for one or two other sugar daddies.

So, put on your cute little black dress, grab a girlfriend, and head out to the local Ritz or W for cocktails.


Second Date With T May 20, 2008

Filed under: Dates,SugarDaddies — AllieSugarBaby @ 5:50 pm
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After waiting for two days, T finally called me this afternoon and wants to take me to dinner tomorrow night.  He wouldn’t tell me where he is taking me, but said I should dress to impress…  him.

I have to admit that I’m already starting to have visions of romantic trips to exotic places and wonderful evenings together.  T really could be the type of sugardaddy that I only need one of – attractive, romantic, and very generous.

On another note, I had a complete blast from the past moment today, as well.  Stephen, my New York attorney, called me this morning wanting to talk to me about “us”, as he put it.  It turns out that business will be bringing him to the area in the next few weeks and he wanted to know if I’d be interested in picking up where we left off 2 years ago.  After some protest and explaining that I had moved on from our relationship, I finally agreed to meet him for drinks next week.  Of course, I will listen to what he has to say and if he sincerely wants to try again, I may give it a shot – of course, a second date this time around may cost him a pair of Prada shoes 😉


Sugar Baby Wonders If She’s Asking for Too Much May 19, 2008

Filed under: Musings,SugarDaddies — AllieSugarBaby @ 8:43 pm
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I was reading this post on the SeekingArrangement blog tonight (Sugar Baby Wonders If She’s Asking for Too Much) and started wondering what some people really think a Sugarbaby arrangement is really all about.

I’m not going to sit here and lie and say that a Sugarbaby arrangement does not have the expectation of generosity in terms of gifts and money.  However, I have never even considered discussing any sort of monthly allowance with the men I’ve dated – it is up to them to decide what sort of gifts or allowance is appropriate, not me.  What is up to me is the decision of whether or not the gifts are enough to keep my attention.

In my experience, when I have found the right Sugardaddy the gifts or allowance will work itself out and will be enough to make both of us happy.  My former Attorney Sugardaddy from New York ptobably never gave me less than $4,000 a month in gifts of money, jewelry, clothes, etc and sometimes when we were together for a long weekend or trip that amount went even higher.  In exchange, he knew that I would be ready for him any time he needed to get away for a weekend or just wanted an exciting night on the town.


An Email I Received Today

Filed under: Musings — AllieSugarBaby @ 7:51 pm
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I posted yesterday about the great date I had with T. Well, I got an amazing first impression from him and the whole idea of finding my perfect sugar daddy online. Today, I received a few emails and one in particular stood out that made me realize that there are a lot of men who really just want a high class escort and are afraid to come out and say it:

I’m a young doctor visiting until Tues May 20 – I’m seeking an intimate encounter in my luxurious hotel. I’m an honest guy and I’ll tell you what I’m looking for – I’ll gladly give you money/gifts for sex – can’t get any more honest than that! Maybe something develops, maybe it doesn’t. I only visit a few times a year, but I’ll take care of you all year, so you’d have your freedom. Does that relationship sound like a possibility to you? I promise to treat you well, spend money on you, and show you a good time… write me back

Well, Mr. Young Doctor, I’m not that type of girl. The relationships that I have are not about sex for money. They really aren’t, despite any ideas you may have about a girl who is a “sugar baby”. The only difference from a typical dating situation is that I date men who want a very attractive, younger woman and are willing to be generous with gifts, trips, and sometimes money. A good sugardaddy/sugarbaby relationship to me is more than just the occasional gift and a roll in the hay – there has to be an emotional connection, even if it is a connection based on the fantasy of being with a “Barbie Doll” or beautiful and intelligent younger woman.

Comparing Mr. Young Doctor to Jim (not his real name), my former boyfriend from Las Vegas, is night and day. The first thing Mr. Young Doctor mentions is sex. Jim never once in the 6 months we were involved mentioned sex – all the times we did, it was me who took the lead. Most of our time together was spent out on the town – dinners, dancing, shopping, and shows.

I won’t let this discourage me, but I think that I’m going to find more men online that are like this than are like my fabulous T.


Meeting T May 18, 2008

Filed under: Dates,SugarDaddies — AllieSugarBaby @ 5:32 pm
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I just got home from a fantastic date. For the sake of privacy, I’ll just call him T on this blog. T is actually the first potential sugar daddy I’ve ever met online and so far, so good. I know most probably won’t go this well, but he definitely made me re-think my opinion of online dating.

He suggested we meet for drinks at the bar at a very nice hotel, so I wanted to make sure to be extra cute and really show off for him. The new dress I bought this morning really looked great and I could tell how much he appreciated the view he got of my legs – the dress is barely past mid thigh on me. He was in jeans and a jacket, but I could easily recognize his watch. One of the first things I look at is a man’s watch and shoes – some things can be faked, but a gold Patek Phillipe can’t.

We settled into a booth together and he ordered champagne for both of us. We sat for about 45 minutes and talked about his business, travels, and the typical things you talk about on a first date. After our drinks, we got up to take a short walk and talked some more – planning a second date, what sort of arrangement would work for both of us.

I normally don’t sleep with a man on the first date and today was no exception. However, the real reason we didn’t is because he had to get home to his wife for dinner. Seriously, he completely swept me off my feet from the moment we started talking to the moment we parted with a soft, lingering kiss.

I’ll meet him for dinnner and shopping later this week. If all goes well, we’ll set something regular up. Either way, I’m always going to have a backup plan.



Getting Ready for My Date

Filed under: Dates,SugarDaddies — AllieSugarBaby @ 1:23 pm
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I’m sure there are a lot of people who think that the life of a sugarbaby is nothing but dining, diamonds, and luxury. In a way, you’re right… Of course, that doesn’t take into account the amount of time and effort getting ready to dazzle a potential new sugar daddy or to keep the attention of an existing sugar daddy.

I spent the entire morning getting a manicure, pedicure, and shopping. I found the perfect dress (a very sexy green bubble dress that will really show off my legs) for an afternoon cocktail date, but couldn’t find any shoes… Fortunately, I have a pair of gold strappy sandals that will work. Will my date be dazzled or will I not live up to his expectations? These are the things that I worry about when meeting a new sugar daddy for the first time.

All in all, I’ll spend probably 5 hours getting ready for a 1 or 2 hour date… Being a wealthy man’s Barbie doll is hard work.