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

Category Archives: Sugar Baby

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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. :)



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If you’re new to my blog I’d like to preface this entry by stating, I’m not just hungry for the “sugar” in an arrangement, I actually seek to build a symbiotic relationship with a man.  He will have the chance to get know me and share with me more than perhaps either of us have ever thought possible, because we are meeting from such a pure place.  Deciding to put myself out there on various websites, matchmaking applications and even this blog were not decisions I’ve made lightly.

Quite frankly, in my opinion any woman who claims they have been given or offered lavish cash and/or gifts (without any mention or promise of sexual intimacy) is full of shit.

I may not be some buxom blonde with fake boobs (which seems to be the typical fantasy for some men), but I do know that I’m considered extremely attractive, I’m young, exotic and able to express myself very well, so I’ve experienced enough conversation (via e-mail) and going on several “POT SD” dates now to know that men are not desperate or dumb enough to give up their goods without coming to some mutual terms with a lady first.  I welcome any arguments or testimonies that may refute my sentiments, so please bring it on because I’m sure we’d all love to hear it (just don’t leave out any pertinent details would ya?)

Now back to my recent weeks, which have been quite eventful!

I’m literally just getting home after my third official date (all men from SA) and the lunch meeting I just had started out a bit wonky, but ended up much better than the dinner date I had last night.

Are you still with me?

Let’s hope my fourth date (tonight), with another gent from SA whom I semi-stood up (but politely rescheduled with) from last week turns out even better! Especially since I’ve accepted a temp-contract out of town and won’t be back for several weeks, I’m hoping this “down-time” reveals which, if any, of these men truly have the potential to be my first SD!

It’s exciting to finally have some real prospects for a change!

In my attempts to establish a sort of storyline that my existing readers might be inclined to comment on and follow, I will start naming my pots in alphabetical order, kind of like the way weathermen name hurricanes.

Last week I had several interesting events and realizations occur.  First, a really hot guy I actually first met in 2013 as a potential client, somehow recently found me on a “regular” dating site without realizing who I was.  (Yes, I am on regular dating sites too, see!)

I’ll refer to him as ‘Adam’.

After a brief chat session, Adam wasted little time inviting me out for a drink and I was happy to oblige, partly because I already knew how hot he was, but mostly because he was man enough to ask me without much thought (you’d be surprised how seldom men actually behave manly, and do something as simple as set a date and time to meet a girl!)  We met at a nearby restaurant, where I spent the first 20 minutes listening to him rant with his arms crossed, about how he’s sort-of-adopted his sister’s dating technique; meet people until you’re blue in the face, (or actually get married to one, which apparently she was ‘lucky’ enough to do).

As much as I instinctively wanted to yell ‘check, please!’ we hadn’t even ordered any food or drinks yet, I decided to give him the benefit of the doubt, being a single dad and divorcee must be hard enough I guess, so I stayed.

Sure enough after some liquid courage and a few hours had passed,  I noticed that our knees had knitted together and he didn’t seem as jaded as I first thought, just extremely insecure about his current situation.  We talked a lot about his child, the stress of his work load and obvious stress of his break-up; a small part of me wished he was a potential SD because I already felt so comfortable and willing to explore intimacy with him (as most women can attest to after first meeting a man, when there’s a strong physical or “emotional” attraction), but I’m glad he’s not seeking an arrangement, although he seems like he’d be fun to “manage”.  (I’ll explain later).

At the end of our date we shared a passionate kiss, although I didn’t hear much from him afterwards we finally reconnected again this week and decided to try a second date (which is allegedly uncommon for him).  Once again after warming up with a few drinks and catching up on the current events of each other’s lives the conversation some how turned to sex, porn and personal fantasies.  After some sheepish avoidance of certain topics we both finally admitted what have wanted, for me it’s a particular orgy scene, but he craves domination.

No doubt because of this new level of openness we just shared, and despite a lonely bartender and a nearby couple, Adam went in for a kiss but this time his hands we all over me.

Because I haven’t enjoyed PDA in so long, I forgot how fucking exciting it can be, and coupled with the fireplace alongside our comfy chairs, I’d be lying if I didn’t say I would’ve let him have me right there if I thought we could get away with it.

Thanks to his stubble and my increasingly sore and red face we both looked at each other, took a deep breath, and hesitantly said in agreement “it’s too soon” before making our way towards the exit.

Of course when we got outside to our cars we shared a last minute kiss that included me being turned around, picked up, pressed against my door, legs spread, and smothered his erection pressed against my inner thighs… not to mention he also grabbed my wrists and held them tightly behind my back, put one hand around my throat and pushed himself against me on the hood of his car while we kissed some more… but that was it.  I’m such a horn dog sometimes I surprise myself, but damn it was so hot!

I went home and tried not to day dream too much about letting him really put me in my place, but maybe one day.

I realize that turned into a bit of a soft porn excerpt but this story has a point.  It was after my first date with Adam that I understood what I really need to do if I intend to be successful in the sugar bowl; GO ON A LOT MORE DATES!

Like most things, success is a numbers game. Simple.

In between those two steamy encounters with Adam I met Barry, a nice-enough attorney, but way too lackluster for me to seriously consider as a SD.  He admitted he’s not sure if an arrangement would work for him, and seems more confident in flirting and chit-chat via text message than in person.  I just don’t see the chance that sparks might fly later on, so I’m sure we’ll both be better for not pursuing anything.

Sugar Babies: What would you do with Adam and Barry?

Well, I’m off to meet Mr. M now (sorry, I don’t think the hurricane style naming system is working but I think you get the point).  I’ll report back later.

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. :)