Simon/Joy: The Bet.

I was really looking forward to my date with Teddy. Neither of us were calling it a "date" but I was definitely treating it as such. I haven't even really been out on many "dates" since I've been here. A few pre-arranged outings, but even when I was seeing Stretch we often just went for drinks after work so I didn't change my outfit or do my make-up differently or anything. The only time I put a lot of work in is if the girls and I were going to a club or I was going solo hoping to hook up. If I had a booty call, I usually would just wear something comfortable and seductive, knowing I wasn't going to be wearing it for long.


For Teddy, though... I wanted to wow him. I didn't want to dress like a realtor going for after work drinks. I wanted to dress like a hot chick on the prowl, someone commanded his attention. The mild weather trend hasn't worked for my advantage but I still wore a nice light dress that shows off my figure, lots of leg and chest - I don't really have cleavage so wearing low cut means I can go pretty extreme. I wore my tallest pair of stilettoes, and even went to Shayla to do my hair and makeup. I can do it myself but not if I want to look all-caps HOT.


Underneath was my laciest, skimpiest thong and no bra. And the chill in the air meant the girls were perky.


It was worth it, though, at least at first, because I could tell he was impressed. I've never seen him at a loss for words but he stumbled to say, "You look -- really good!" I blushed, "Who, me?" I could tell he was trying to play it cool but I examined his trousers for signs of attraction.


I have to admit, there are parts of being a chick I really get off on. It's nice to have people treat you like you're this small, precious thing they need to protect and care for. I like having chairs pulled out for me and doors being opened for me and being looked at with that fawning gaze. I like how he takes any opportunity to touch my lower back to guide me, or take my lightly by the arm on the way into the restaurant.


I also relish being a chick who isn't a chick. All those things that I hated about my old girlfriends, the way they would nag me and get pissy if they thought I wasn't paying attention to whatever I was saying. Who really cares? We both know what we're really here for. Any guy who might end up dating me is hella lucky since it would basically just be like dating a bro with tits, and let's face it, what guy doesn't basically just want that?


I tried to avoid work conversation and asked him about his personal life. We got into the subject of how he was a workaholic in his 20's and 30's and now he was paying the price, because he never settled down. That was getting a bit serious, but I used to opportunity to reach out and touch his hand and say things would be okay, it wasn't too late.


He gave me a weak smile, cleared his throat, and asked about Stretch.


"Oh, uh, I guess that was an open secret, huh? What did he tell you?"


"Nothing," he said, "He was pretty secretive about it, but we could all tell something was going on."


"Yeah, uh," I felt my voice creak into an even higher register, shifting in my seat, "It didn't work out. I think he was into me, but the reality wasn't quite what he imagined. He thought I was some pretty, innocent little princess."


He smirked, "Oh, and you're... not that?"


"No," I smiled wickedly. "I'm a dirty girl."


Holy shit, I was getting myself hot.


He looked away. "Good to know," was all he could say. I was a little irritated. Why was he backing off. Didn't he want this? Am I somehow not good enough for him?


Finally I broke down - because after all, I would've loved a chick to be this straightforward with me - and said, "Hey, what's going on here, man? Are you into me or not? You can't tell me you're not feeling it a little."


He hemmed and hawed. "I... you see... it's complicated."


"What, because of Stretch?" I scoffed, "Aren't we past that? Aren't we all grown-ups? There was nothing there and if he's not over it, that's his problem."


"It's more than that," he said, hinting at, well, something big. "You... really don't know, do you?"


"Know what?" I was truly baffled. "Are you, like, gay or something?"


"No, no, I'm not..." he said. "God, I can't believe I'm about to say this but I can't let it go on."


"Say what? Dude, you're scaring me." I searched my mind. I wondered if it had to do with the Inn or someone knowing my secret or... someone having a secret of their own? But I was way off base.


"Joy," he said with a severe look on his face, "There's a bet."


I raised an eyebrow. "A bet?"


He sighed. "There's a bet around the office over who could hook up with you first."


I just stared. I'm not even sure I blinked. "Uh... what?"


"Sully and the Big Guy were talking one day, about how flirty you were with everyone and how it seemed likely that someone was going to, well..."


"Hit that?" I completed his thought for him.


"I guess so."


"And Stretch was part of the bet?" I felt my heart sink a bit.


"Yeah," Teddy nodded.


I took a pause before my next question. "And you?"


He bit his lip. "Only indirectly."


"What the hell does that mean?"


"Well, they figured that if I somehow 'won' that would be it for them, so they made me put some money in the pool."


"How much?" I said, too stunned to raise my voice beyond a whisper.


"$500 apiece," he shrugged. I had to restrain my reaction - disgusting, perhaps, but it's hard not to be flattered by being worth that much money.


Before I could say anything, Teddy piped up, "Joy, you've gotta know... I wasn't really in it. I had no plans to try to win, if anything it made me want to keep you at arm's length."


I sniffed, "Well, that didn't work."


"I'm sorry I didn't tell you sooner," he sighed, "Things between you and Stretch seemed pretty legit and I didn't want to wreck that."


"Yeah, that would have killed it if it wasn't already dead," I sighed.


"If there's anything I can do to make things up to you, just let me know."


"Let's just forget about it," I sighed, "And try to enjoy our meal."


"Okay," he said.


"And hey, Teddy... don't tell anyone I know about the bet, okay? It sucks but I'd rather not deal with it."


"Whatever you like," he nodded.


I was obviously a bit distracted for the rest of the night. I'm seeing a few downsides to embracing the whole "sex object" thing. I'm more than just a pair of tits and ass - as fabulous as the assets I got from the original Joy are (well, she could use a boob job maybe but I'll leave that for the next Joy.) I'm good at my job, I'm a decent person, I'm good company. I'm a lot of things. And I happen to enjoy getting laid, same as I did as a man.


It makes me miss the thrill of the chase. Yes, sex is easier to come by and I can take my pick of partners, but man was it exciting to have to work for it. I miss the game.


Then after the weekend, I realized... I'm still playing the game. Just by different rules.


So I got my phone out and texted Teddy - we hadn't talked since Friday and I was feeling bad about that.


"Hey... thanks for telling me all that stuff on Friday. I really needed to hear it."


"No problem, I'm sorry again," he said back.


"So... want to win a bet? ;)"


To be continued...

Simon/Joy: Stretch, Sully, the Big Guy and Teddy

I had sex again last night, big deal. Only this time I went over to the guy's place, because I didn't want Treena to judge (until she reads this.) It was kinda messy and smelled like a locker room... and is it weird that that turned me on a little? It was far from home, and I thought I could maybe spend the night, but I felt too awkward so I Uber'd home at 3 AM. Exhausting.

I could probably just keep hooking up with random dudes as long as I like - there's no shortage of bro's at the bar lining up to buy me a drink - but it's starting to wear me down. It's getting repetitive I'm not patient enough to set up a really good screening process so I usually just pick the first dude who gets to me, which is probably a recipe for disaster. I've thought about online dating, but I also don't like all the buildup and I'm seriously not looking to date, and all the guys who only want something casual on there are kinda... gross, tbh. But I have one last option. Work.

Some people are not into the idea of mixing business with pleasure, but those people are missing out on lots of fun. Seriously, you have a group of people you have to see day-in-day-out for years and you never even consider bumping uglies with any of them? Waste of time. Some say it causes workplace hostility, but only if you do it wrong. Plus there's something sexy about sneaking around, having a secret (lol, tell me about it!) and generally being naughty.

In fact, many years ago I had it hot and heavy with this girl from accounting. She dressed real conservative but she was a total freak. Loved anal and wanted me to tie her up once. Not that I'm up for any of that, but, you never know. She dumped me cold and I never fond out why.

So you might recall I spent the holidays with my co-worker Stretch. I honestly thought he was gonna make a move on me but if he wanted to he didn't try very hard and I wasn't up for it yet. Now that I am - and honestly I think I've been strutting around the office like a cat in heat for weeks trying to get some attention - and nothing. He seems shy, intimidated by me. Yawn.

I'd consider it if he would just man-up and make a move. He's tall and thin and clean-cut... kind of a Ryan Gosling look to him. I could go for that.

But he's not my only option around the workplace. In fact, there's three other guys I have a good relationship with: we flirt, we tease, we have long chats about the weekend. There's the Big Guy, who is so-called because he weighs about 300-lbs, and I know what you're thinking... sounds gross. But I think he's actually more athletic than any of the other guys because he hits the gym constantly. Good square jaw, looks like he used to play football in college. He just sweats a lot. He's vulgar and brash, and probably loves the fact that I can execute a perfect "That's what she said" joke.

Only, I think I saw him wearing a wedding band when we first met months ago... and now it's mysteriously disappeared. Not that I've ever asked...

Then there's Sully, kind of a cross between the two. A bit older than Stretch, and chubby but not "fat." We've teamed up on a few sales, and he is a smooth talker. He keeps telling me that one night, when he's free, we're gonna hit the club together. I have no idea what he needs to be "free" from... he does, however, have a face that looks like a potato and I don't think I could live with myself if anyone knew I had "hit that."

Lastly, there's Teddy. Honestly, besides the fact that Teddy is over 40 and looks it, he'd be the guy. Like, he's kind of who I see myself being in 10 years, and who doesn't want to screw themselves? Aloof, soft-spoken, but smart as hell and surprisingly funny. The man has been my idol, a bit, since I got here, and I'd be lying if I said he didn't occasionally pop into my head when I was "with myself." (Or with another guy.) But that aloofness means he can play hard to get... and I don't know if I have the patience to unwrap all those layers. I'm only here for a few more months so if I want something consistent, I need to act now.

In case you were wondering, Joey is dating some Filipino chick. Good for him, Asians are hot, but I'm not gonna deny that I'm annoyed that now that I'm ready he's off the menu.