Breaking Out of Boring

I eventually pulled the dildo from my ass and went to take a shower. I was a dirty girl now after all, if my ex could only see me now; I smiled at the thought.

The next month went by without anything of note (other than my new anal regiment that occurred a few times a week) and I was happy to be wrapping up summer school and have a few weeks of freedom before the regular school year began. The Saturday after my final day of summer school was when the band was scheduled to play again. I had tried to get some other teachers to celebrate by going to the bar with me but they had all planned on taking their vacations that weekend. I called some other friends to see if they'd want to go out with me but they also had previous plans. That's what happens when you're one of the few single people left in your friend group, you get left to fend for yourself on a lot of weekends.

The Saturday rolled around and I spent a large portion of my day trying to figure out how I would explain being there by myself and not look like a loser. Not to mention would he remember me? Would he want to hang out with me or had he only talked to me because of my dad? I decided my course of action would be to act like my friends were coming and just say they cancelled on me last minute.

The band started at 8 but I started getting ready at 6. I wanted to look my best without it looking like I wanted to look my best; you know, that casually cute look.

I hopped in the shower and took my time shaving. With no prospects of getting laid over the past year things had become a bit...unkempt. I shaved my legs, all of them, not just what might be seen, hit my underarms, made sure there weren't any stray hairs anywhere on my lip or between my eyebrows, and then turned to my pubic hair. I usually kept a nice little strip of hair but tonight I felt more daring than I'd felt in a while and, for whatever reason, shaving myself bare felt more in line with that notion.

I stepped out of the shower and started sorting through my closet for what to wear. It was hot out so maybe a dress? No, it wasn't really a dress kind of bar. Jeans? Maybe the dark blue wash that makes my ass look good. Shorts? No I don't have any that look good enough. Then I spotted it. I hadn't worn it in a while but I always got compliments when I did. I grabbed the blue skirt off the hanger and tossed it on my bed. It had a slightly ruffled edge that landed a few inches above my knee. Not too short, but enough to show off a little leg so I hadn't shaved my legs for nothing.

Now for a top, not that there was much of a question there; I had always been fond of a white scoop neck t-shirt that I'd had for years. It made my chest look fantastic without showing a ton of cleavage. It was my go to first date shirt, not that this was a date, I reminded myself.

I grabbed my brown ankle boots with a slight heel and set them by the bed. I surveyed the outfit and was happy with my final selection. Or was I trying too hard? Maybe not the skirt. Maybe just jeans. Go a little more casual. Would he like casual more? He's in construction so maybe he's a more laid back, less formal guy, or, maybe he gets that all day every day and loves a girl that's dressed up? Dammit, I was overthinking it. The skirt, Go with your first instinct.

Ok, the outfit was settled, now came the big question: if tonight goes really well, like really really well, and we end up back here or at his place, am I sleeping with him or not? That determines what I wear under the outfit. No, no I'm not sleeping with him, he'd think I'm easy if I put out that quick. Junky underwear it is. But...what if it goes perfect? I mean, I wouldn't say absolutely no. It has been a while after all. Ok, so don't wear your worst but don't wear your best. Who the fuck am I kidding if the opportunity is there I'm going to take it, I shaved my pussy for a guy that might not even remember me. If he shows interest, he's getting some. Good stuff for sure.

I pulled open my drawer and grabbed my best white bra; a push-up with a white satin edging that I'd only worn once before to rave reviews from my ex. Then the real search began, with my white top I'd had one option, with the skirt I could wear anything. I began tossing anything I thought could be an option on the bed. Once everything was out I tossed my towel aside, threw on the bra and started trying on bottoms in the mirror.

Black thong, blue cheekies, white lace boyshorts, red g-string, I wasn't wanting for options as underwear was a bit of a shopping weakness of mine. Unfortunately I didn't like how I looked in any of them tonight. I wanted 'wow' but all I was finding was 'not bad.' I went through my drawers again, hoping I'd missed the perfect pair, but to no avail. After a while of staring at all my options again I reluctantly resigned to a lacey yellow thong that I hadn't worn in a while.

I glanced at the clock and realized I had been messing around with my underwear selection for almost 20 minutes and now I was running late. I threw on my clothes, curled my hair slightly, and bustled out the door around 7:45.

I pulled in at the bar after a car ride of second guessing my outfit, second guessing my whole decision to come, and second guessing whether James was the guy I remembered or if I had just built him up in my mind. In the end, I hadn't turned around and I was here. I took a deep breath and got out of my car.

As I walked up to the doors I could hear the base drum thumping and the faint sound of the band playing already. I opened the door and walked inside, scanning the room for James. I didn't see him. Shit. He hadn't come. I hadn't even considered that option. Now I felt like a complete idiot for all the effort I'd put into this.

Oh well, I'll at least have a drink or two and listen to the band for a bit before heading home; it was a charity benefit after all so I could at least help out with that. I walked to the bar and waited patiently for the bartender to see me. I ordered my gin and tonic and watched the bartender scurry around trying to find a lime to garnish it with.

"$6.50 please," the bartender shouted over the music as she handed me my drink.

"You can put that on my tab. And also a jack and coke please." A voice from behind me called to the bartender.

I turned around and found myself face to face with James; well, more like face to chest, he was quite a bit taller than me after all. He was so close it caught me by surprise and I took a quick breath; he smelled amazing. He smelled faintly of cedar and what I could only describe as the smell of a man. It made me swoon and my stomach twist into a knot of anxiety.

"Oh hi, you scared me! You don't have to do that!" I responded.

"Don't worry about it. I was supposed to buy a round of drinks for some friends that were coming but they bailed so you can be the beneficiary of their poor choices." He smiled.

"Well tell your friends thanks for being dumb. My friends actually just bailed on me too. I was just going to grab a drink or two then head out since I don't know anyone."

"Well why don't you stick around for a while and we can save each other from an evening of drinking alone?"

"Sounds like fun. Don't you know basically everyone here though? I wouldn't say you're alone."

"Ehhh...know them yes, want to sit and end up talking work with them all night, no. They're nice and everything but it's the weekend, clock out for God sake!"

"I'll drink to that!" I said, holding my glass up.

"Wanna grab a table?" He asked.

"Sure! Lead the way."

I followed him through the tables towards a spot on the far side of the bar against the wall. I wallowed in his scent as it drifted back to me and enjoyed watching his body twist and turn between the tables. He grabbed the back of a chair and swung it easily out of the way and I couldn't help but notice his forearm ripple as he did. I was done for. I knew it. This was either going to end with me in his arms or going home woefully disappointed and wishing for so much more.

As we got to the table he pulled my chair out then sat down at his as I took a seat. For a moment he didn't say anything, he just looked at me. It totally unnerved me and I felt myself blushing.

"What?" I asked sheepishly.

"Oh! Sorry, that probably looked like I was staring at you like a creeper. There's a TV behind you with the game on, I was just looking for the score."

"Oh, haha yeah I thought you were staring at me." I replied. Well that was disappointing. I thought he might actually be looking at me with that kind of intensity. Typical guy though, always has to find the TV in the bar.

"Not that you aren't worth staring at." He said with a smile that pulled me right back into fawning over him. "You look beautiful by the way."

I blushed harder, "Thanks. You're not so bad yourself."

"Thanks!" he said cheerfully, "So you're a teacher if I remember right? And you were doing summer school last time; is that still going?"

"It just finished yesterday so I'm officially free actually."

"Well congrats on being free, that's worth drinking to." He said raising his glass to mine.

"I already know all about what you do for work, so what kinds of stuff do you do for fun when you aren't working?" I asked.

"Fun stuff...I dunno...I guess I'm boring. I don't want to be boring, my days just kind of end up that way. I go to work, come home, take the dog for a walk, then crash on the couch for some Netflix."

"What kind of dog do you have? And what are you watching on Netflix then?"

"He's a big fat Beagle. Fat because I give him too much food from my plate every night but I can't help it, he's my buddy and it makes him happy."

"Haha awww that's cute."

"Netflix...I'm all over the map lately. I've been watching Sherlock, Shameless, Archer, and then I'm always up for a good documentary. I watched that one about schools called 'Waiting for Superman' the other day. Have you seen it?"

"I'm a teacher, of course I've seen it. It's super depressing but a really good documentary."

"Right?! We have enough dumb people in the world, I'll pay whatever the schools need to get me a few more intelligent conversations each day."

"Hahaha who says you're one of the smart ones?"

"Ouch! Damn! If you can feel your brain cells dying over there I apologize, I'll move to another table. I wouldn't want to contribute to the general decline of humanity. What about you, what do you do for fun?"

"Ummm...ya know, I don't know. I used to do all sorts of stuff but since I graduated and started working it seems like fun is few and far between. I guess I do this; come out for a band and drinks. That's about the extent of it I suppose."

"So, what kinds of music do you like since you like seeing live bands?" He asked.

"I like most stuff as long as it's good. I mean, most genres. There's good country stuff, bluegrass, blues, pop...ya know, just depends on my mood I guess."

"That's cool, too many people get stuck in one genre and never really give other stuff a chance. So what mood are you in now and what genre are ya feelin?"

"I'm...relaxed...and happy. I could go for something sort of like smooth jazz or sort of bluesy I guess. Something kind of slow but happy."

"Like...hmm...ever heard of Marc Broussard? Something like Lonely Night in Georgia?"

"Oh my god I love that song! Yes! I actually listened to that song while I was getting ready to leave tonight!"

"Haha he's awesome isn't he? I love all his stuff."

"Not many people know his stuff, I can't believe you picked that of all songs. Ok umm...let's see...depressed. Let's see if you can name what I'd listen to depressed"

"Haha depressed? Wow nice job bringing the mood down...hmmmm, ok well answer me this, are you a lyrics girl or a general feel to the song person?"

"Mostly general feel. Lyrics only when I'm looking to jam and sing along."

"Ok then I've gotta go with...damn depressing is hard, I don't listen to a lot of depressing stuff. Ok, shot in the dark cuz I doubt you've ever heard it, 'Eet' by Regina Spektor."

"You try to spend half of your liiiiiife, trying to fall behind. You're using your headphooooones to drown out your mind. You've gotta be kidding, how do you know that song?" I asked as I pulled up a playlist on my phone titled "Sad" with Eet as the 3rd song. "Look at that. That's insane!"

"Hahaha ok c'mon keep going, let's see how long we can do this. This is fun."

I proceeded to list off another 5 emotions and all 5 times he listed songs that I loved. They weren't always my go to songs or anything, but they were all songs I knew and really enjoyed.

"Ok, one more. Something hard. Give me a tough one."

"A tough one...ok, ummm..." what I wanted to ask immediately popped to mind but I wasn't sure that I was brave enough to ask it. I thought of others before finally telling myself I had to get out of my comfort zone at some point. I looked him dead in the eye with all the confidence I could muster and said, "Horny. What do I want to listen to during sex?"

I immediately regretted it. Oh god that was too much. Change your mind, say something else.

His eyes locked onto mine and a wry smile spread across his face. "Ooo, took that 'hard one' literally did we? Ok...hmm...well let's really figure you out shall we? You're beautiful, so you probably have plenty of guys after you." Wrong. "But you might be too intimidating to talk to, so you might not see that they like you." Uh oh. "You're too shy to make the move yourself so you've probably been single awhile." Yeah so? "So you're probably a little self-conscious because guys don't actually say anything to you so you think they aren't interested and there's something wrong with you." How the hell. "So when you do get a guy into bed I'd bet you're concerned what they might think for fear of losing them." Ok I'm panicking now, how does he know this? "So...you aren't putting any music on during sex. You'd be too worried they'd judge your choice."

"How...how could you possibly have figured that all out."

"Sorry, that may have been a bit much. But yeah, most people don't play music during sex and you just seem a little too shy to make the suggestion, so I just took a stab at it."

"I'm going to need to drink more if you're going to verbally undress me to my core like that again."

"Haha sorry, I won't do it again. Honestly it was a guess; the rest was just some suspected observations that might support the guess somehow. But really if I was right, you shouldn't feel self-conscious about anything. You're beautiful, smart, and have a good sense of humor. What's not to like?"

"My ex found plenty I guess." I responded drearily.

"Well don't worry about him. From what I've heard he's an idiot."

"Wait, how do you know about my ex?"

"Haha, I don't, all I've heard is he's your ex, ipso facto: Idiot."

"Oh...thanks!" I said smiling. Damn he was smooth. Disarmingly smooth. "Well what about you. Why don't you have a girlfriend? There doesn't seem to be anything wrong with you and you certainly know how to make a girl feel special."

"Ohhhh...that's a long story. The short version is I dated a girl for 4 years from college and after graduation; looked like we were going to get married and the whole shebang, but then she had some big epiphany that she wanted to be a travel writer. She got a job that had her traveling for 7-8 months out of the year and that's not what I would consider to be a balanced relationship so I left. It ended pretty ugly and wasn't quite as clean of a breakup as that sounds, but it was for the best. Since then I've just been avoiding online dating until stray cats start wandering up to my door because they're attracted to the lonely smell coming from my house. I never make a move or hit on women because I always feel like a creep trying to start up a conversation out of the blue with someone I don't even know. So, here I am, just me and my fat beagle eating our way through the days!"

"Hahaha aww, well I'm sorry it didn't work out with your ex."

"It's fine, really. The further away it gets the more I realize I probably should have broken it off sooner. Just got stuck in something familiar and didn't see all the stuff that would have eventually ended us anyway. But enough of this ex nonsense."

The rest of the night was a blur. We talked about everything from an article he had read about scientists being able to pull drinkable water directly out of the air to recalling our favorite parts of the movie Liar Liar which had been on TV recently. It was the most fun I'd had since, well, the last time I'd been with James. Before we knew it the band was finished for the night and it was almost time for the bar to close.

I stood up to go to the restroom when I suddenly realized how intoxicated I'd become. I wasn't drunk, but I definitely wasn't sober. I was going to have to uber home, shit. I didn't live that close and that was going to be an expensive uber this time of night with all the bars closing. When I got back to the table I pulled out my phone and opened the app to see how much it was going to set me back. Sure enough, it was looking to be a $50+ ride home. I hadn't even realized how many drinks I'd had, I'd been too engaged in our conversation.

"Everything ok?" James asked, clearly seeing the disappointed look on my face.

"Yeah, it's fine. I'm just going to have to Uber home and it's going to cost me like 50 bucks."

"Oh you have your car here?"

"Yeah, wasn't planning on getting quite so tipsy tonight. I'm blaming you and your free drinks by the way." I teased.

"Haha well if it's my fault, then it's my job to fix it." He replied. "You have to uber back to get your car tomorrow or do you have someone to drop you off?"

"I don't know, haven't gotten that far ahead yet. It's fine, really, not a big deal."

"Well...if you don't want to pay the $50, there's always another option, I live literally 5 blocks from here. I have a spare room with a big cushy queen bed just waiting for someone to get too drunk to drive home and spend the night."

"Are you sure? If you really don't mind that would be awesome. I promise I'll be gone first thing in the morning so I don't bother you."

"Nonsense! I'll make breakfast in the morning and everything if you don't have anywhere to be. Copper loves sausage so he'll be pretty pumped about it."

"I mean...that sounds amazing." I smiled.

"Ready to go then?" He said holding his hand out.

I took his hand and we headed towards his place. I don't have the biggest, neither do I have the smallest hands in the world, but James's hand engulfed mine. His hand was warm and slightly callused from work. It made me feel so tiny next to him, but it also made me feel safe, like I could trust him to take care of me. It was a feeling I hadn't felt in a long time.

As we walked to his place I staggered in my drunkenness a few times which ended in him wrapping his arm around my shoulders to steady me. It wasn't cold out, but the wind was a little chilly and being hugged to his warm body felt nice. We flirted and talked the whole way back to his place.

Once arriving and getting inside, he introduced me to Copper, his beagle, who barely got off the couch to greet us in his sleepy state. James pet him for a moment before telling him to go back to bed to which he promptly jumped back on the couch and curled up in a tight ball.

He showed me to my room just down the hall from his and told me if I needed anything to just let him know. I gave him a hug, thanking him for letting me stay there. The hug probably lasted longer than it normally would have given my state of sobriety, but I loved being buried in his chest.