Memoirs of a single girl seeking the sugar baby lifestyle… for the second time.

Tag Archives: decisions

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Today I was supposed to meet Cowboy, but after a long, drawn out explanation on how discreet he must be due to his ailing wife, and basically flaking on me a few hours before our lunch meeting, I realized that he seems more interested in finding a convenient toy immediately rather than an actual sugar baby, but should I care?  Luckily in the time it took me to cancel that reservation, Captain Carl responded back to me on SA asking me to confirm my availability for a slightly later time.  Despite initially thinking he might be a creep (after he took forever to reply to my texts and didn’t answer my call), we finally spoke on the phone and agreed to meet.  I’m learning to be more patient with these men who are prone to be less ‘text-savvy’.

After I almost approached the wrong man at the bar where Captain Carl said he was,  I was relieved to see that he looked completely different than what I imagined, but I liked his clean cut style and the fact that he didn’t emit that horny-toad, desperate, lonely guy vibe that some men do.

Unlike my previous dates since I started this blog and my sugar adventures (Mr. J that turned out to be more like Mr. ‘John’), and attorney #1, Barry, (who probably can’t handle me or any SB) I was completely unabashed in my disclosures to him when asked “what’s your perfect situation, what brought you to the site?”

I couldn’t help but rattle off about my life as it’s been thus far and the many hats I’ve worn professionally that have lead me to seek a mentor and dominant figure in my life who might help focus, guide and discipline me for a change.  He seemed so judgmental of me and actually said “Ok, now I’m starting not to believe you!”  I looked him square in the face and asked defensively why it was so hard to believe? I explained that not everyone believes their life should be wasted in cubicle, how I could verify my work history and have absolutely no reason to lie to him about such things he retorts saying, “I’m just teasing you”.

Finally he concedes to say, ‘Well, this might be a turn off for you… but I also don’t know what I want to be when I “grow up.” Then goes on to list a handful of various businesses he’s owned, invested in and wants to sell… tells me how he thinks I’d be a “perfect” personal assistant for him since his previous lasted six years and was now a mommy, so he wants someone new to keep his affairs (and privates) in order.  He asked me to tell him what my salary requirements are, and said he doesn’t like to discuss money, so once we agree on something it will come “like clockwork” and we never have to speak of it again.

I wanted to call him a mother fucker, but instead I felt an energy shift which boosted my confidence back up.  I never should’ve doubted he wanted me in the first place.

I’ve got to stop thinking these men have any control over me because they truly don’t.

“The major difference here is that I don’t have a bank roll to support my various interests or major professional accomplishments under my belt yet!” I snapped in retaliation.

His desire for a ‘personal assistant’ is actually a major turn-on for me because, as mentioned, I don’t just want to waste my time getting to know someone who just wants me solely as an activity or intimacy partner. I can find a fuck buddy anywhere, or wait for Adam to come around and admit he wants to be my boyfriend, but waiting around is exactly what I’m not going to do anymore.

I want to learn while I date multiple daddies, and I’m wondering how many daddies I want at once…

Before I knew it I admitted to Carl that I am so fed up with passive men that I have seriously considered becoming a dominatrix.  (This is a topic I haven’t seen addressed yet in many sugar blogs, but personally I’m aware that being serious dom holds a certain allure and power that far supersedes anything many of us have ever fathomed or fantasized about in the sugar bowl).  But that’s definitely a topic for another day…

Now Carl is back in his home state, awaiting my “decision”, Cowboy is actively seeking a discreet sb, Barry is sweet but boring and Adam is the regular joe who I want to do very naughty things with… but will wait.

Sugar Babies: Do you think having a married SD is worth the trouble? And have you ever had a SD request you as a personal assistant with benefits? What would you do and what would be your salary requirements?

Ivy

XXXO

If you enjoy my posts please SHARE IT, COMMENT and FOLLOW.  

This blog was created as a memoir and in-depth account of my real encounters, experiences and research findings.  I hope that it may help shed light on the dating scene from an objective, (albiet “amateur” point of view) as it pertains to “sugar”.  I also hope to educate, entertain and inspire along the way. :)


FUCK ME! Those were the words I almost blurted just 4 and half hours into my first date with my first potential sugar daddy from seeking arrangement…. Luckily he really was “too nice” and although we had a fantastic time conversing about all sorts of topics at a fabulous restaurant in Atlanta, he made it to second (or third) base but that was it!

Literally, moments after my last post I found my teeth chattering, not just because it was 30* outside but because I was genuinely nervous, and exited to meet my first “prospect”.

Dr. J asked me to meet him at a nearby bar, I got there just minutes before he did, made a quick stop in the ladies room to check my hair and then proceeded to the bar where I witnessed a myriad of couples and characters.  Some looked “normal”, one blonde could pass for the neighborhood watchman (if you know what I mean), I of course, felt like I stuck out like a sore thumb.

When I realized there was only one empty stool at the bar I texted Dr. J, then realized the man three feet to my right was Dr. J, although he looked a bit younger in his photo. “Oh my, you brought your friend!” I said, “No, this guy is the maître d’! I’ll find us a place, no worries”.  Immediately he noticed what the situation was, took control of it, and I was relieved.

He wore a dark velvet blazer, classic Levi’s and a pair loafers that came straight out of Michael Jackson’s shoe closet.  He was the epitome of what an “older man” looked like in my mind.

We sat at a nearby booth and the conversation flowed, thank goodness!  Him being from the NorthEast, I immediately recognized his accent and took comfort in it.  He yammered on and almost immediately started explaining how he gets so many ‘winks’ from SA that he hasn’t really encountered anyone worth meeting, so I was glad when I realized that he was truly grateful for what had across the table… me.

The conversation went way deeper than I ever thought, and in the back of my mind I thought what most women probably think of when they meet someone they ‘click’ with… “yeah, he might get some!” Whenever he made a witty joke or referenced something that I really related to I tried to hold back my devious smirk.  He really seems to understand me, I thought.  He was completely straight forward about his past experience with online “sugar dating” and the fact that he has been a bachelor his entire life, despite having wanting to get married several times.  I mentioned that I was seriously not in search of an “arrangement” because I hate labels!  I went on to state that I cannot pretend to like someone, I was not just on SA to find a man who would give me a “paycheck”, and wouldn’t pretend with him.  I did like him though and I was trying not to show it.

The last thing I expected was to go back to his place, and I should’ve known what it meant if I did.

After a few cocktails and some appetizers I accepted the invitation back to his house.  He was very vocal about the fact that he did feel lucky to be with me, and agreed that I was right for seeking an SD on SA, so that I might find more men who treated me like a Queen.  Since it was only a few minutes past 10pm, and everything was going so well, I figured it would be harmless to leave the restaurant with him and go with the flow.

We arrived at his house, not too far away from the city.  When I tell you the interior was pristine, I am speaking literally!  He had beautiful cars that I accurately guessed he loaned out for movie scenes, all sorts of interesting trinkets and the place was spotless.

I admitted to him earlier in the night that “My over-active imagination pictured you kidnapping me and stealing my kidneys or something!” so his P E R F E C T L Y organized home kind of freaked me out, but thanks to the whimsical additions of Asian art, random collections of books and shot glasses, I felt more at ease.  It wasn’t long before he gave me a tour of what could be “my room”, (with rent adjustments optional depending on how often I wandered my way into his room).  Yes, he was quite the smooth-talker.

Just as I anticipated it, he made a move and hugged me which lead to a whirl around and then onto his bed.  I giggled, said I needed to use the ladies room and he immediately backed-off.  When I returned he replayed the move and I had to say, “ok now, let’s calm down a bit and go back downstairs for the rest of my tour.”

I definitely realize that successful sugar dating has A LOT to do with being adaptable, and saying the right thing at the right time.  Even though you should keep in mind, at the beginning (and end) of the day, the only thing most men want to do is fuck.

I want sex too though, and I want this to be very clear.  I’m quite sure in fact that I want it a lot more than the average girl, and to my dismay, the average guy I’ve dated; so this is my disclaimer to you wannabe sugar babies out there, don’t ever feel obligated to have sex unless you really want to.

After Dr. J wrapped my tour of his home, the moment felt right and I let him kiss me.  He likes to stick his tongue out a lot, but I love to make out so I was happy to play with it for a while.  We made our way to his couch, composed ourselves and kept the conversation going about stupid TV shows and movies as while lit his fireplace.

I initiated the next kiss.  It has been too long since I was last intimate with my ignorant ex-boyfriend and I was really horny. I figured he wasn’t well-endowed because I couldn’t feel much when I straddled him, but he was passionate.  Before I realized it his tongue and lips moved away from mine- down to my nipples and it felt amazing.  In another swift movement he started rubbing my clit on the outside of my jeans, then slid his hand inside them.

Between my moaning and his sucking I was sure we would have sex, but in the back of my mind I said “NO! I have to stick  to what I’ve learned.  I cannot have sex with anyone, EVER again, on the first date!”

I truly believe that if I were a man, or even less in control of my sex drive, I’d be a porn star.

In any case, Dr. J was quick to toss me on my back, pull off my jeans and wiggle his tongue all over my lady parts.  After a few moments he unbuckled his pants, took of his jeans and tempted me to pleasure his member.  With all my might, I caressed it for a moment, held him close to my lips, but kept my composure and simply said “I’m sorry I can’t”.

His jeans were buckled up in record time, and I felt badly it had gotten that far.  He hurriedly took the drinks he had mixed for us to his kitchen sink, but proclaimed he was not upset when I asked if he was.  It was obvious he expected more from me when he finally admitted “Well, I mean I’m comfortable going down on you but you’re clearly not comfortable doing anything with me without a condom!”

He was right, the main reason I stopped him was because he didn’t have a condom, but I’m glad he didn’t because we would’ve had sex for five minutes and I would’ve hated myself afterward.

After we sat back down, he threw his legs over mine and relaxed a bit.  Then he explained (in so many words) that he only makes around $20k per month, so I needed to decide if I wanted an “arrangement” or a “relationship/arrangement” – which is what he felt I wanted.

The truth is, YES, I do want an allowance, but I also want to be spoiled and appreciated!  I want it all I suppose.

While he realized this from our previous conversation, he still admitted frankly that he was only able to “write a check” for $500 each time he was “with” someone.  He went on to say that may very well expect to see someone up to four times per month, but that was something he budgeted for.  The same way he allotted for charity, bills and everything else he kept so perfectly rationed in his life.

As much as I appreciate the amazing dinner and night cap we shared, part of me can’t help but feel like his explanation is too “black and white”.

Am I being irrational?  Isn’t this exactly how sugar dating is supposed to go?  Am I getting what I wished for?

I fear (and hope) that ‘Yes’ is the answer to all of the above, and while I’m excited (and aroused) by it, I wish I would stop doubting myself, or him for simply being honest.  Honesty is exactly what I need, and after all, a “guaranteed” $2k per month is nothing to scoff at, right?

For anyone who reads this, or any other sugar blogs and thinks- “SEE you’re just a wannabe PROSTITUTE!” Shut the hell up… because when you really think about it the way Dr. J has laid it out for me, I’ve learned so much in one night.  I’ve learned that the truth is that many of us spend our whole lives merely fighting for and exchanging ENERGY with one another.  Everything we do in a friendly, intimate or volatile relationship is a type of energy exchange.

What makes anyone feel they are RIGHT for deciding to have sex with  someone for “love” vs. trying to forget the faint memories of a one night stand?  None of us can ever know whether our (sexual) decisions might lead us to a lifelong relationship with someone else.  Being a proactive single person, pursuing a certain ‘type’ of partner seems like a more rational way to go about dating!

I think I just answered my own question, and I think I’ll just lay low and see if Dr. J invites me out to a few more dinner dates before we [eventually] do the “deed”, because the truth is we’ve already established that there’s undeniable chemistry between us and that’s far more than I ever expected, or have had with anyone in a long time!

As nervous as I am for what the future holds, I am equally excited and hopeful that he will be exactly what I need – for the foreseeable future.  That’s more than I could ask for from any man, and it’s about time I started telling myself to want more from any man I date, so I feel good about my decision!

Stay tuned sugars…

Ivy

XXXO

If you enjoy my posts please SHARE IT, COMMENT and FOLLOW.  

This blog was created as a memoir and in-depth account of my real encounters, experiences and research findings.  I hope that it may help shed light on the dating scene from an objective, (albiet “amateur” point of view) as it pertains to “sugar”.  I also hope to educate, entertain and inspire along the way. 🙂