Wannabe Sugarbaby

Monday, May 12, 2008

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 interesting comments, I've decided to dust off a few unpublished posts.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.

posted by Tiff @ 2:12 PM | 1 comments

Saturday, February 02, 2008

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.

posted by Tiff @ 4:45 PM | 7 comments

Friday, June 22, 2007

I Can't Believe it's June!

I'm such a procrastinator! I bought a self-help book on procrastination months ago and still haven't read it. Anyway, I've been meaning to write, I really have, mostly because I miss writing this blog dearly. A lot has happened...

I've learned so much about myself from these men who made appearances in my life. And I don't have any sad feelings or regrets when I think about them.

And I thank you too for being part of my journey. No one tells you what it's like to grow up.. the hurt and the pain, building a life independent of your parents. Finding friends, a family of your own choosing.

The affair with MM ended months before our actual conclusion.
I was ready to let go completely.
I found myself getting annoyed with little things that he did. Little things that I thought were adorable when we first met, I began to loathe. I never loved him, but as soon as the lust began to wear off, so did my enthusiasm.
Our last night together he touched my breast and I barked back "I'm not in the mood right now!" He made several more attempts to reignite what we once had.

MM was easy to let go of... because I never really loved him.
It was an "arrangement of convenience" in the purest terms of the phrase.
Along the way we both got lost.
I wanted security and marriage.
He wanted exclusivity and stability.
In fact I think he went as far as drawing up a prenuptial agreement with his legal council.
I loved the idea of him with me.
The sugardaddy and sugarbaby, legally bound and satisfied with each other.

But then what?
My ever beating heart lacked the passion that fueled it.
I would never be happy with MM. Only satisfied.
So I began to withdraw, his control issues and ED made it easy.
I began to see him as an old man with insecurities more severe and unchangeable than mine.
And it was sad.

He asked me if a was seeing someone else, as I was never in the mood to fuck him anymore.
Well, the answer was yes, I was seeing other people... but being fully conscious of his emotional attachment to me, I only confessed to one.
"I must admit" I replied reluctantly, "I am seeing someone else."

Then a hidden side of him to which I had not yet been exposed to revealed itself.
"WHAT??" he bellowed, "I've asked you this before and the answer was always no, how long has this been going on??"
"About two months" I replied, quickly adding "but we haven't had sex yet."
"I don't believe you, knowing how high your libido is, I find it hard to believe you've abstained from sex for the last two months."
And he was right, I couldn't go that long without sex. But after having incredible fuck sessions with a certain man, I realized how awful MM was in bed.

For most of our relationship, I rejected any propositions that came my way.
Feeling it was only fair to reserve my carnal desires for him and only him.
It worked well for a while. Though he was easily pacified, sex with him was like being fondled by a teenager in the backseat of a car.
As time went on, my allowance decreased. He seemed to take for granted my presence in his life. My intuitive response was to withdraw emotionally and physically.
So I bid adieu to MM soon to be DM (Divorced Man).

posted by Tiff @ 10:46 AM | 5 comments

Sunday, January 28, 2007

The Cynic

"The cynic knows the price of everything and the value of nothing." - Oscar Wilde

Napoleon.
He was short with blonde hair and blue eyes.
I made the mistake of assuming he was generous, because he bought me a ticket to a fundraiser without knowing my name.
Little did I know, he loves the thrill of meeting a stranger.
I met him on a popular sex site, from what I heard it was bursting with potential sugar daddies and I was itching to try it out.
He was my first date.
He didn't think I would show up.
I wore a flimsy demure top with no bra and little jewelry.
He wore a custom fitted suit, the price of which I knew before our first date.
The first indicator.

I wasn't attracted to him at first as I prefer tall men.
But as the evening prolonged he became more attractive by the second.
He was articulate, intelligent and yes attractive in the conventional sense.
We went for drinks at a swanky cigar bar after the fundraiser, during which I made no mention of my financial needs. I had decided before hand that tonight was about getting to know the man not his wallet. My need for financial aid was minimal at the time therefore chemistry was of the utmost importance.
During our conversations prior to meeting he had dropped varying prices. The cost of his suit, the price of his maid service and other items he had managed to attain at a steal.
Indicative of a cynic.
He seemed controlling but I'm not quick to judge, I wanted to give him a chance to prove me wrong though my instincts are usually dead on and I trust them completely. Besides, he was extremely sensual I wanted to see how good he was in bed.

The night ended and we parted ways with a kiss on the cheek to keep him wanting more.

Round two
We met at a popular restaurant.
Despite a reservation and it being a weekday we waited for a table.
Napoleon announced he would order for us "if I didn't mind" before cracking open the menu, no wonder he was single. Rarely have I met a man more controlling than this. Yet I indulged him, and observed even closer. I could sense he had the dying need to make all decisions, but held himself in check. Afterall, he needed to impress me to have any chance of getting in my pants that night.
So we had shared an appetizer he preferred and an entree as well. Luckily I wasn't particularly hungry and feigned enthusiasm upon tasting each dish (they certainly would not have been my choice). He offered to get me something else then made an excuse for why each dish I suggested was unacceptable.
Dinner was quick.
He then suggested a martini bar in my neck of the woods.
Always a step ahead, I knew he thought he might get lucky as I did meet him on a sex site.

Althought I felt we had different goals in mind, I consented to a drink or two at the martini bar.
We had fun, as I usually do once the infamous social lubricator is introduced to my system.

We laughed, we danced, we had some things in common.
It was now or never.
"Do you recall the title of my profile?" I asked.
Knowing full well it was "Sugarbaby of your dreams."
He said he did.
I asked "Have you ever had the sort of relationship I'm seeking?"
"Well.." He paused "What do you mean?"
He was playing dumb and I played right along.
"A sugarbaby is spoiled and pampered by her sugardaddy, it is a relationship of mutual benefications" I replied.
Quickly adding, my sugardaddies in the past have been extremely generous with "$XXX per month"
He looked away and the caressing stopped. I could tell he was uncomfortable and trying to think of something to say.
"I'm not particularly in need of that sort of arrangement" He replied with a pained expression. "I don't have to pay for women to be with me."
I wasn't surprised by his reaction and quickly came to my own defense "This is not a transaction of any kind, it's only that I do need some help of the financial persuasion in order to see you at leisure. Take as much time as you need to think about it and get back to me."
He said he would, but I was extremely doubtful.
We kissed deeply and parted ways once more.

I was not expecting his call, but I did receive a few texts from him.
His fantasy was for him and I to face a mirror and watch him enter me from behind. I replied with saucy texts for some time but eventually ignored the rest of his contrived enticements. It became clear to me that his idea of a "Sugarbaby" was a world apart from mine.

posted by Tiff @ 7:11 PM | 4 comments

Saturday, November 11, 2006

Current Events

He called me last weekend. Gino did.
My phone rang, and it was a number I thought I recognized.

"Hello"
"Hi... its Gino, I'm just calling to say hi."
Calling to say hi after two months? I thought.
I wondered if his call had anything to do with his friend Teddie who was helping me with a new start up business.
"Hello there, I wasn't expecting to ever hear from you..." I cautiously replied.
"Are you in one of your 'I hate Gino' moods" he asked in a teasing tone.
"I don't hate you I'm just kind of... indifferent towards you at this point." I had to put him in his place.
He was taken aback. "Wow, I was expecting you to be polite."
"I think I am being polite, just being honest."
I relented and had a polite conversation with Gino regarding his current events and mine.
Then he said he had to run off to watch the end of some game.
He concluded the same way he began, "I was just calling to say hi..."
"Hi back" I replied, and hung up.
I'm stumped as to why he could be calling me now, unless of course he misses me. How sweet.

Things with MM and I have hit a rough patch. He invited me and a friend to an event and the entire time he was trying to set her up with an acquaintance of his. I was under the impression that he wanted to get closer to me by meeting my friends. Instead, it seemed that was a ploy to round up fresh meat for his "good old buddy."
I felt uneasy and we left as soon as the event concluded.
After a day of ignoring his calls we finally spoke. It was a very typical fight, with me being passive aggressive and him refusing to apologize. He had to leave town shortly after and I won't be seeing him for a week or so.
I think we've had a good run and it's time for us both to move on. But right now would not be a good time to end things as I believe he is in need of my company. So, I'll plan on ending things early next year. In the meantime, I'll try to be more understanding and supportive to ensure things wrap up as neatly as possible.
The elusive virtue of patience has finally chosen me.

I called Michael because I missed him terribly and hated the way we ended. We'll be having coffee soon, I'm happy about that.

posted by Tiff @ 5:20 PM | 4 comments

Thursday, October 19, 2006

Three sometimes

It was one of those dubiously late afterparties.

I waltzed in with two friends, seeing some familiar faces I felt right at home with.

Suddenly an unfamiliar individual came to me with an unforeseen proposition.

"Hey, you're truly gorgeous, my girlfriend is bi-curious and she wants to meet you, are you interested?"

I could tell this was not the first time he made such an introduction.

His name was Dan. Short with sandy blonde hair, cocky and absolutely NOT my type.
But I was interested in meeting this girlfriend of his.
We maneuvered around the overcrowded venue and towards a private candlelit table for two.
There my eyes gazed upon a geisha.
She was Japanese and stunning. My desire for Asian women dates back to a prepubescent time in my life. Many hours spent in the library immersed in books and masturbating to them.
Don't be crass.
I can get my self off without touching myself remember?

She was inebriated at the moment we met. Chatting briefly about nonsensities I spied her checking me out and knew she was certainly interested. I exchanged numbers with her boy who expressed his intentions to ring me later.

Two days later.
Her boy does in fact ring me and we make plans to go to a strip club.
I make it known that I am not at all interested in him and I would like to be with her privately.

We meet for drinks at her apartment and departed to the club shortly thereafter.
Partially clothed women, drinks, cigars and conversation flowed unchecked. Her boy is either broke or cheap, so I pay for my share of the alcohol. We get a private lap dance from the most beautiful girl I have ever met and leave the establishment.

Back to her apartment utterly sopping with liquor. She says she wants to be a stripper. So I volunteer to be her partner, telling her we should dance together.
Perfect chance to get closer.
She smells like almonds everywhere.
I do mean everywhere.
I kiss her softly on the lips, and then her collar bone and then her neck and down her chest and the her belly button and then...
Her boy insists we move to the bedroom, my eyes are on her and I'll follow wherever she leads.
So to the bedroom where she quickly sheds her clothing and I take off her panties eager for a taste. I spy her boy getting undressed too and make a mental note of it.

Back to where we left off... To her nipples down her chest to the trail that ends at her slit.

I lick her from the bottom up, slightly parting her lips and teasing with my tongue.
The taste of almonds again, a bit stronger this time.
MMMMM. I dive in, tonguing her intensely, I watch her eyes roll into the back of her head.

"I bet lover boy never made you feel this good." I think to myself and tongue her clit again before thrusting her opening with my rigid tongue.

All the while her boy is at her other available openings, refusing to be ignored.
Then he is at mine. During this intensely sexual moment I am unable to say no but insist he put on a rubber. Which he does.

He is fucking me and I am fucking her with my tongue.

We all climax successively and suddenly the all too familiar uncomfortable knot forms in my stomach, I feel the sudden urge to leave.
Her boy reminds me that I'm drunk; this I acknowledge and end up sleeping on the couch.

The next day after a shower and a meal I realize what has happened. I was taken advantage of at a vulnerable moment.
Instead of abiding by the pre-discussed arrangement, her boy, being the opportunist that most men are jumped into our session when he should not.
Upon my epiphany I called the Japanese beauty and let her know the arrangement unabashedly.
"That was not supposed to happen" I explained, "I regret having sex with your boyfriend because I am not attracted to him, but I would like to see you again."

From my understanding, he's leaving the country soon anyway.

I've heard from her once but no more. I'm sure her boy keeps a tight leash on her knowing that once he is out of the picture, he will be replaced with ease. I'll keep my fingers crossed and look forward to my next rendezvous with the Japanese Princess.

posted by Tiff @ 10:47 PM | 3 comments

Friday, September 29, 2006

What the F**k

I've written 6 unpublished posts since I last posted, bear with me darlings.

MM invited me out to dinner the other night. He had mentioned a friend who was in town that he wanted me to meet. I tried to probe into the identity of this "friend" but he remained elusive.

When I arrived at the restaurant MM behaved as if it was a meeting by chance and introduced me as an acquaintance that he "used to help but does not help anymore," at this I struggled to suppress a look of surprise. As I wasn't briefed and had no idea what to expect, I went along with it.
He went on to suggest that his friend and I go clubbing together, without him, since he wasn't into big city nightlife. Huh??
Is this his attempt to pass me on to his friend as a sugarbaby? Or just some sort of test?
I agreed to give his friend directions to wherever he may like to go, and possibly show him if he needed additional help.

He will explain the purpose of this awkward evening tonight.
I feel as though something has changed. I can't quite put my finger on it, maybe he's acquired a new sugarbaby or has reconciled with his wife... Something is awry. My temporary solution is to show him the new sex toys I've bought, and play all night.

In the meantime, I have begun to look for another sugar daddy. In the midst of my search, I got an email from Tom who stood me up because I didn't give him a number. Shall have him take me to the most expensive restaurant in town to discuss our potential mutually rewarding relationship? That would be most appropriate.

posted by Tiff @ 3:24 PM | 1 comments

So You Wannabe a Sugarbaby?

My Quest to become a rich man's barbie doll.

Tiffany

24 years old
USA

I love: Shopping
I hate: Working