Jeffrey

*Ring* *Ring*

After just having lunch with Pencil Boy (which I bought myself), I figured it must be him calling to relay the sweet nothings he couldn't get off his mind.

"Yes darling?" I answered.
"Well hello there, aren't you in a happy mood" a raspy, over-confident voice responded.
"Ah, hello Jeffrey, I'm always happy to hear from you, how are you?"
"I'll be much better once I see you, what are your plans for Friday?"
It was Monday, he was calling a full 5 days in advance to be sure I would be his on Friday night. This was over-zealous behavior for Jeffrey. Appearing effortless was his game.

"Nothing so far, what did you have in mind darling?"
"Well.. partying like rock stars, what else?"
I laughed, "I'll see you Friday then" and hung up.

While I am interested in seeing him and slightly amused by his eagerness, binging the night away doesn't sound like the greatest time. I'll have to coax him into taking it easy. This much is certain though, whatever we do, it'll be a night to remember. Game on.

Things I Miss

Hope you all enjoy the new trimmings, felt like I needed a bit of a face lift plus my archives work now :)

Earlier this year I decided to put the sugar lifestyle behind me. Feeling completely jaded after dating the Asshole of the Century (from now on referred to as AC). Peter, as in Peter Pan was my next foray into exclusivity. What a mistake that was.

For all the talk of abandoning the sugar lifestyle I really do miss it. I miss the all expenses paid vacations to exotic five star resorts. I miss the tuna tartar, jewelry for no reason and his visa with my name on it. Beer and fried food is not my idea of a good date.

Is it not possible to be a go-getter career woman and still be embraced by Chanel? My problem last time was garnering the motivation to achieve career success when all my material needs and wants were pacified. I think now my maturity and personal drive has solved that problem.

Towards the conclusion of my last hunt, I fine tuned a strategy for catching sugar daddies. It wasn't intricate, on the contrary, it reigned simplicity. I call it Über-fishing; throwing out as many hooks as possible and seeing what bites. I had an ad on all the Sugar Daddy sites, I was listed in multiple personals (local&national) and I attended as many upscale events as humanly possible. Draining but ultimately, it was craigslist that bit back. Go figure.

Now that I'm re-considering, I took a look at the popular Sugar Daddy sites once more. The mere thought of exchanging countless emails with misrepresented fakes, low ballers and ungracefully aging men gives me chills. Based on my previous experiences, I think much success (and peace of mind) is to be had by freestyling. This way you can completely eliminate the email tag and gauge his sugar-providing ability once his business card is in hand. You've just got to know where to look and show up in all your fab-ness.

I have a gift that benefits me quite well, I've mastered the art of active listening. During initial conversations I listen most carefully. This enables me to pick up hints as to what he desires most. Based on his history with other women and his own admissions I can become exactly what he wants. I can also read his non verbal cues and cater my every word and action to elicit a favorable response from him. This I do automatically now, with all men.

It's proven to be an invaluable skill. On the other hand, I'm unsure of the long term implications of this sort of manipulative behavior in the context of a healthy relationship. Wouldn't it mean I'm molding myself to another's image of the perfect lover rather than being myself? That I put my own needs second to his in order to get him to open his heart and his wallet? Food for thought I suppose... I think what I've missed most is sharing my thoughts with you all.

Cat and Mouse

So, friends... it has been a while. A little over a year to be exact and everything has changed.
I will be sure to play catch up but at this moment I have something to share. A new infatuation and possibly a new love. He's reckless, unpredictable, and so bad for me. We come from similar privileged backgrounds but my parents would never approve. Which is just as well because I've decided not to even think about children and marriage until after the age of 30. Ha! A far cry from the Tiff who just wanted to "get married or live comfortably with my rich boyfriend."

Though he is rich with a trust fund and full access to the family jet, much of that is irrelevant to me. There's a je ne sais quoi quality to him, we connect. He has a wild free spirit I can wholeheartedly relate to but I'm hesitant to get involved with him. I feel that "wild, reckless" phase of my life has long past. The phase during which I slept with strangers, partied all night and slept all day was fun but I'm not so much into that lifestyle now. This time in my life is about structure and developing the necessary skills to ensure my future success, such as discipline and punctuality. A part of me feels like he would only pull me back into unproductive habits that have taken years to overcome.

Jeffrey is 35 years of age, 6 feet tall and slight in stature. He is disarming (arrogant when inebriated) with a boyish smile, blond hair and hazel eyes. He has been bestowed with the tacky moniker of "Hugh Hefner junior," but... his attitude and presence is like a fucking magnet, I can't help being attracted. Is this wise? He has no idea I feel this way about him. I've gone out of my way to be that unattainable woman. Giving him shit everytime he leaves himself open and using my wit to taunt him. I've become such a challenge that I've unknowingly initiated an intense chase. It's cat and mouse, he wants what he wants. A man accustomed to everything falling into his lap always wants what is most unattainable. When we last spoke, he asked me "What are you looking for in a man?" To which I responded "What makes you think I'm looking?"

A truthful answer, which has provoked his curiosity, quickened his pace and leaves me in the involuntary position of the pursued... Shall I run or shall I succumb to him? If I'm to be his conquest perhaps he should be mine, wouldn't it be interesting if he fell in love with me along the way? After all, I can never turn down a good chase.

Q & A - The Subject of Money

ANON SUGARBABY:
I found your blog and it's really amusing even exciting reading.
I recently joined a seeking arrangement site but being next to this type of arrangement I have no idea how to start talking /discussing the financial help you might expect.
I always think it makes you seem like a gold digger or so which I am not cause I have my own business and take care of myself now.
but you can always use some more right?!
it seems that once men start talking to you, you end up chatting and they want to meet you but there is no word about making any agreement.....
I met a wealthy men last weekend who I liked and he likes me but spending the night he pushed himself to much on me en we ended up having sex which was totally not what I wanted to do, I could relate to your story with the geisha lady.anyway there was no talk about an agreement
I was all messed up.I don't know...

I you might have some advice for me that would be great.


TIFF:
That's a very good question. There's no perfect/easy way to bring up the topic of money, but if that's what you need then you must state that.

First off, try to get a feel for how generous he will be by the places he takes you to and how well he tips. Next make sure you're into him and he's into you, take your time here, go on a few dates if you need to. Finally when you feel the time is right (basically you both click and he wants you sexually) bring up the topic by saying he's wonderful and you like him a lot but you have certain needs as well. When he asks the you about your needs, let him know you don't want to come off a certain way (gold digger, etc) but you could use some financial help.

If he's not experienced with being a sugar daddy ask him for help with big ticket items like rent, tuition, etc. Then see what he says and go from there. You never know, he might have had an arrangement in the past and might even suggest it. If he's not interested then move on, if he is you've got your daddy. Do NOT ever get drunk and become unable to control yourself. A lot of these older gentlemen are very well versed in the art of seduction and you will be seduced if you let it happen. Meet in public, do not go to his place after dinner even if he has some fabulous antique he wants you to see, that is bait. You can kiss and fool around, but NO sex (oral included) until he begins to help you. Capice?

Hope this helps,
Tiff

PS: You haven't really messed up with your guy unless he's some player on the prowl. You were drunk and he took advantage of that but don't let it happen again, still inform him of your needs during a romantic dinner and see what he says. Even if he says he will help, do not go back to his place unless he has handed you some "help" during dinner. It's all about action not words.


ANON SUGARBABY:
thanks for this information it is a good guideline on how to phrase your needs.
I met also another man who lives in my country, busy businessmen blalbla and I have the view that because they have met you on such a dating site that it seems to be ok to just sleep with you at once instead of going into the normal dating routine but of course they wouldn't want to date a prostitute.
Luckily this man immediately was open for an arrangement and I walked out with a nice envelop....will see him again also.

For the other man, I think we are slowly getting there, he is very sexual so most of the conversations on the phone are about sex but I made it clear that I don't want to be the one just giving the best of me and not getting anything in return so that leaded to the big arrangement question.
then he asked me if I had a budget in mind???how to say that??I could say a certain amount while he had more in his mind or less, so I could lose out some extra cash....
I was planning to say when he asks again what do you think I am worth to you? Is that a good idea?
pfff this dating is difficult but I think when you have a few established relationships it can be great!!


TIFF:
Don't say "what am I worth to you," you need to tell him what you think you're worth. In my opinion, you should ask for an amount that covers all your monthly bills, including rent and leaves you with enough cash for two spa trips. If he can't afford it he will let you know that and you can go from there.

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Fast Forward

If someone would have told me this sugar baby saga would last more than 4 years, I would have shrieked and called them a liar. But here we are, almost half a decade since my first post and the quest for a wealthy man is still a theme in my life.
At this point in time I've been with my current lover/sugar daddy/boyfriend for almost two years. We've discussed all the particulars that any two people in a serious relationship would discuss; babies, marriage, the future. We are quite comfortable. He has taken very good care of me financially with a monthly allowance, expensive gifts, trips and shopping. Until recently...
I will not delve deeply into this subject but as of late, he has not had the means to pacify me. This puts me in an awkward position.

I know I need help, particularly because of a new venture I have decided to undertake. I feel I must seek intellectual, financial and even perhaps emotional support elsewhere. The hunt has once more beckoned me. The sweet thrill of the chase, the uncertainty and even the shady individuals. I suppose one could say I actually miss it, the sugar daddy hunt.
There have been many a time in the last two years I encountered a fellow with the means to be my "patron," but I would throw away their business card or give them the wrong number because love always prevails. Right?

I'm not so sure at the moment. I think love is fickle, it comes and goes as it pleases. When I'm in his arms, in the throes of passion I surrender completely. I let his love seep to the core of me where it coats my insides and I am at peace.
Because we don't see each other regularly this love starts to dissipate, I forget what he looks like, begin to miss him and then resent him for making me miss him. It is madness.
In recent days I've yearned to experience independence such as I felt while with MM. Support without love involved. Perhaps all this love is exhausting and I just want to breathe and be me again without being tied to him.

Or perhaps it's just stress and this restless feeling too will fade with time. I hope that is the case because life without him would be washed out and boring. But in order to entertain myself, I shall keep my eyes open and reintroduce myself to the more formal ways of finding a sugar daddy.

Freestyling: Going to upscale establishments (gyms, restaurants, coffee shops) and events (fundraisers, art shows, sporting events) in order to meet a successful gentleman.

Online dating: Creating personal profiles online that include flattering pictures and detail what you're looking for.

Traditional personals: Creating newspaper/online based text ads that briefly describe you and the type of relationship you're looking for.

Stay tuned.

J

Upon receiving (and publishing) an abundance of... interesting comments, I've decided to dust off a few unpublished posts. The following was written early last summer. Enjoy :)

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A man whom I am not at all into is on his way over.
He's well traveled, polite and generous but other traits of his turn me off. We've known each other for quite some time but only recently has he been honest about his "true feelings." He told me he's fancied me, for as long as we've known one another.

After dating another man whose success I admired but personality I tolerated, I refuse to do it again. Though he is accomplished, I don't feel a thing for him sexually. Thank god for the 20th century. In another era I may have been persuaded to consider him as a potential spouse!

Under normal circumstances I would take his profession of lust-love as a delusion and laugh it off. But it's different this time. He's my sister's ex boyfriend. One she has dated casually but nevertheless an ex. Is this off-limits territory, or am I allowed to indulge regardless of his close relationship with my sibling?
It makes me uncomfortable.
I cant help thinking of her lips on him when I kiss him, and he's a skilled kisser.
Can you imagine the distraction?
I think since my attraction to him is quite minimal and taking the discretions listed above into account, I shall move on. But first inform him of the reasons for my dismissal so as to avoid hurt feeling and burning bridges in the process.

Oh my

It has been over six months since I last blogged. What was once so comforting seems strange and unfamiliar now, even the blogger layout has changed!
I will try to catch up, starting from the oldest memories to the newest :)

I'm happy to be back.