Balancing Act

So I thought the difficult part of being an SB would be finding a good SD that would want to keep me around (thank you, poor self-esteem). However, I'm currently balancing 5, and have talked to a few more. That would typically be fine, but they all seem to expect monogamy from me, and some form of commitment. Currently there's -

  • Buff Boy - he's the exception. He's really just looking for the occasional hookup. That's fine, although I do wish he paid a bit more.
  • The Investment Banker - texted me last night asking if I could take off work next week because he wanted to take me on an overnight trip. Um no, I can't really just leave my law firm (with no vacation days accrued) and one week's notice. And we've only met three times. RED FLAG.
  • West Point - definitely wants monogamy, seems like the kind of guy that expects this to grow into something more than just an SB/SD relationship. More about him later.
  • The Nerd - we met for dinner on Sunday of this week and he's already invited me to come visit him over a weekend in the pacific northwest while he's up there for work. AND offered me a job in August working as PT pr/advertising for his entrepreneurial startup. Hi, moving too fast much?
  • Asian Attorney or AA - young, married, wants monogamy but is not willing to pay for it (as in his monthly price is on the lowest side of the Sugar Scale).
As you can see, things are starting to get tricky. Especially with West Point. We met for dinner last night at a well-known restaurant near my work, and he was just as tall, dark and handsome as I remember him being from our lunch meeting. Maybe even more so. I found out he had unexpectedly had to attend a funeral today so he was feeling down, and admitted he had almost cancelled but thought seeing me might cheer him up. Which is especially sweet, since he knew there wasn't a 100% possibility I'd be going anywhere with him afterward. We talked about everything, from politics to books to losing loved ones...he says he loves my intelligence, and that I know what I want from life and am pursuing it wholeheartedly. He told me he's very "mentally attracted" to me (didn't mention physically...hmmm) and is so glad we met. Swoon. However, that's when he threw out the "looking for one girl who is looking for one guy" card. Of course I nodded emphatically and agreed, touting monogamous Sugar relationships as the only rational course of action. It's frightening how good at lying I can be, truly. We still didn't discuss "the arrangement" itself which worries me, because I like him, but I don't want to give it to him for free or close to it. That's not why I'm Sugar. Otherwise I'd just be a goldigging slut. (The differences between the two are subtle and nuanced, I realize).

On top of all the SDs, I'm also balancing the Boy, who thinks we're monogamous/possibly dating, and all the randoms in my life that are trying to hook up with me (for free). Ever since E and I broke up, they've been coming out of the wood work. One of them I actually might like (Shaggy), but how to hang out with him without the Boy finding out? Hmm...very carefully.

xo summer


Ladies and Gentlemen....she's back!

Well well well, hasn't it been quite awhile since I've seen the inside of this blogspot textbox. Let's just say a few serious "real life" relationships took me out of the game for awhile, but I'm back and ready to play.

Three weeks ago I had my first sexual encounter with an SD (shocking, I know). We'll call him Buff Boy. I drove the 3 miles to his house (awkward), downed a crown and coke, and got it on in his four-post bed. The sex was....mediocre. Afterward, he ended up taking me to one of my favorite hole-in-the-wall Greek restaurants. Hopefully, the waitress didn't recognize me. Turns out he knew a lot of the people that graduated from my high school a few years ahead of me that had siblings close to my age - can I just say that the Southern city I reside in, despite being one of the largest in its state, feels like the smallest at times? Sigh. He disappeared on some trip and texted me again this Saturday, so we'll see what I decide about that. He just dropped some bills in my purse before I left since we hadn't discussed an arrangement, and it was a few too short for my liking.

The same week I met up with a sweet investment banker from Oklahoma who seemed like a doll. The following week we decided to consummate our new arrangement and met up at a very nice, well-known hotel downtown. We had a couple of drinks, some dinner, and headed up to his room. The kissing. Oh the kissing. Ever since dating E (my last boyfriend), no one else's kisses seem to compare. The Investment Banker's included. It was a rough 20 or so minutes until finally I just stood up and unzipped my dress. Worked like a charm. The sex was alright - nothing to write home about, and a bit sweaty and prolonged....he never did get off (too many gin and tonics, he claimed), but several hundreds in my purse when I walked out seemed alright with me for my time. I saw him again last week and it was a bit sweatier and even more prolonged...but he is so sweet and the money is excellent. He's traveling this week, but I'll most likely see him soon.

Tonight, I'm having dinner with another investment banker/consultant - West Point (since he went there). Tall, dark, handsome, intelligent, a bit too military-minded for my tastes, but seems gentle and kind. We didn't discuss in advance whether we would be "hanging out" post-dinner, but I'm thinking not since he would have had to have booked a hotel room. I hope not at least - it's been a long day and I didn't shave my legs this morning. Maybe I'll fake the roommate emergency phone call if it comes down to it.

So there's a bit of an update about moi - hope you all are fabulous!

xo summer


and so it begins...again

So my illustrious career went on hiatus before it even really started. That's alright, because I'm back in the game. 

I met a potential SD on Friday - let's just call him Cute Dad, since he is, after all, a father (and husband, which takes me into the dangerous, uncharted waters of what some call the "affair"). I won't talk about how it's slightly awkward that he shares the same name as my own dad. =\

I was a nervous wreck when I walked into the Starbucks, remembering at the last minute to order my drink with my pseduonym and not my real name in case he was already there - which he was. He was much more attractive than his picture - he had the tall, dorky thing going on - which I absolutely love. I was shocked by how easy it was to talk to him. We ended up sitting and chatting for a little over 2 hours, and I'm supposed to meet him for lunch on Tuesday after my class. We both admitted that this is our "first time" at the SD/SB thing, and we'll hash out details in our next meeting. I'm still really nervous about the sexual aspect, but luckily there's physical attraction, so it should come easily. 

I was supposed to meet another potential - let's call him T - tomorrow, but he drunk-emailed me last night saying how excited he was to meet me today (Sunday) and then sent another e-mail saying he'd missed me at Starbucks, when I had clearly said Monday. His stupidity makes me want to ignore him, but I might as well see what he has to offer. He's single, which makes me think something is wrong with him. Is it wrong that the married guys seem more legitimate to me? If you're single and have enough money for a sugar baby, then why can't you meet girls in real life, you know? Who am I to judge though...they might be socially awkward and ugly, but I'm a whore. 


Sex with Mini-Me

While sitting through a rather monotonous afternoon class today, I get an IM from Athena asking if I'd be interested in a job with her that involves watching this guy jack off. Thinking of my dangerously low gas tank, I enthusiastically tell her I'd love to. 

Side note: the thought that I was having this conversation with her over IM while sitting in class taking notes on my laptop with 2 people on either side of me was rather thrilling, I must say. End side note. 

Seeing as this was my first real "job" in my newfound field of industry, I was a little bit nervous so of course I was beyond thrilled that I wasn't going to be alone. I meet up with Athena and we go to his apartment complex to lay by the pool until he arrives, discussing everything from religion to greek life while we wait, thinking all the while that I really couldn't be happier to have stumbled upon this amazing girl who has so much in common with me. 

Fast-forward: We follow him up to his nicely furnished, if somewhat metrosexual apartment to roleplay that we're looking for a new place to live. For whatever reason, he says that Mini-me once lived here and we all analyzed the logistics behind midget sex. Yes, seriously. 

He offers us Blow Pops to suck on while he whips his semi-hard dick out and starts to stroke it. I didn't know whether or not to look him in the eyes (he has gorgeous eyes by the way) or to stare at his dick so I just awkwardly switched off, all the while sucking on my lollipop praying my tongue wasn't turning a putrid shade of green (which it was). 

Like Athena said in one of her last posts, his hand job was bordering on violent, but surprisingly was extremely hot, and he got some excellent height when he busted his load. To be fair, he was pretty good-looking in an overly tan, ex-football player, "I'm not gay but I shave off more of my body hair than a stripper" kind of way. 

In summary, the easiest $75 I've ever made, with a free Blow Pop to boot. With the added bonus, of course, that I can tell I most definitely have a kindred spirit in my new friend Athena. Stay on the lookout for our planned trip to the lesbian bar this week (my first time!).


A New Adventure

First posts are always so mundane and cliché, so I'll try to keep this short. I'm Summer, just another average sorority girl at a prestigious school in Texas trying to graduate debt-free and happy. To achieve this aim, I've followed in my newfound friend Athena's footsteps, and have decided to try my hand in the world of...companionship dating, if you will. My clients will be mostly older, oftentimes married, and always wealthy with a penchant for spoiling young girls like myself. I am not a prostitute, an escort, or a whore - although I do think of myself as a sort of modern-day courtesan. I promise to always be truthful and share even the ugliest of truths about my new life. I'm looking forward to sharing my adventures!