“Hey!” I said as I jumped in the passenger seat of my Dad’s truck.

“Hey! How ya been?” He asked as he pulled away from my apartment building and headed towards the bar.

“Oh, ya know, its summer so can’t be too bad!” I replied cheerfully.

“How’s summer school goin?”

“It’s fine. We went on a field trip to some old one room schoolhouse nearby yesterday and I had to chaperone; turned into a bit of a nightmare when two of the other chaperones didn’t show up. Otherwise it’s been pretty good though. I’ll probably do it again next year for the extra money.”

“Well that’s good. At least it keeps you busy during the down months.” My dad commented. He was always worried my summers off would be spent getting into trouble; even after I’d graduated and become a teacher. He never said it outright, but he was always concerned if I didn’t have enough to keep me busy. I had never been the problem child, I’d never gotten into trouble at school, always had good grades, and never gave my parents a reason to think I was going to get into trouble if I had some free time, and yet, they were parents, so they worried. My dad was especially protective, not wanting his little girl to get hurt or scarred by the real world.

“So who exactly is this band we’re seeing? Someone you work with?” I asked.

“The lead singer and two of the guys in the band work for a contractor that I do a lot of work for. I went and saw them when they did a gig for a cancer benefit and they were pretty good. I figured it was something fun to do on a Friday night.” When my parents had gotten divorced years ago, my dad and I had promised to at least have a night out once a month, just the two of us. Usually they consisted of dinner or drinks, but tonight he had asked if I wanted to go see a band that was playing to which I happily agreed to the change of pace.

“Sounds good! What kind of music do they play?”

“They kind of run the gamut. They play a fair amount of old rock but also have some country, blues, and new stuff that they play too.” He answered.

“Sounds right up your alley!” I commented, “Do these guys work for the guy you like or the other guy?”

“Haha, I don’t dislike ‘the other guy.’ They’re both nice guys. These guys just really know their stuff and do really nice work that’s hard to beat is all. They take a lot of stress out of it by avoiding problems a lot of the other guys run into.”

“Ah gotcha. Are they the ones with the computer images you showed me of the job before it’s done?”

“Yeah, the renderings. The contractor’s son does those. He’s also running some jobs now too so I’ve worked with him a decent amount lately. He’s about your age I think.”

“He’s 27 and he’s running full construction projects? On his own?”

“Seems like it. He’s the only one out on site and the only one that’s making phone calls and asking for bids so I’d say he’s running them mostly on his own.”

“Damn. Is he any good at it?”

“He’s learning, so he has moments where he misses stuff, but that’s to be expected. He’s better than most of the 50 year olds out there though and he’s pretty quick on his feet so when he does miss stuff he’s quick to admit he screwed up and offer a good solution. Honestly the fact that he admits to the screw up is more than 90% of the guys would do.”

“Well that’s nice. At least someone is showing some integrity these days.”

We sped along talking about work and various other things before finally getting to the bar. It was an older place that had been there forever but always had live music on the weekends. I had been there a few times before and it was a neat little spot. The walls were covered with knick knacks that had been collected over the years: old signs, license plates, trophies from teams they’d sponsored, even some kid’s artwork. It was a very homey sort of vibe and that’s probably why it had survived all of these years; well that, and they had decent food and cheap drinks.

We went inside and grabbed a table near the front as the band was finishing setting up. We took our seats and ordered drinks; my dad with his go to bud light draft order, and me with my standard gin and tonic. We sipped on our drinks and watched the band getting ready as we talked about what jobs my dad had been working on.

My dad was sort of a jack of all trades; he did framing, finish woodwork, some drywall every now and then, and on rare occasions he might do some electrical. He had tried to teach me some things growing up but I had never been keen to learn what I had deemed to be ‘boy stuff.’ At this point in my life I really wished I had picked up some of what my dad had been trying to teach me as it would have saved me from constantly calling him to come fix any number of things that were broken. Unfortunately I was pretty helpless when it came to home maintenance and it probably wasn’t going to get any better now.

Eventually the band got going with a song by a lesser known artist that I absolutely loved. They were actually very good and I soon found myself singing along and tapping my feet under the table. I was having a good time when I noticed coming through the door next to the stage, a very attractive guy about my age. I noticed him, sure, but I turned my attention back to the band almost immediately; I was here with my dad after all. I’m not the type to make a move on a guy in a bar anyway and can be pretty shy when it comes to the dating scene; probably why I’d been single for the past year and a half as my mother liked to remind me.

I didn’t even notice the guy walking towards us until he pulled out one of the chairs at our table and sat down.

“Hey! How’s it goin? Did they just get started?” He asked my dad as he shook his hand across the table.

“Yeah just a little bit ago. Maybe their third or fourth song. James, this is my daughter Amy. This is James, he’s the contractor I work for’s son.”

“Hi, nice to meet you! Oh! This is your monthly night out isn’t it? I’m sorry, I won’t take away from father daughter time.”

“It’s fine.” I reassured, “We knew there’d be plenty of people that he’d know here. I’m basically just here to check out the band.”

“Well who doesn’t love a good band?” James smiled.

Over the next hour I got to know a little more about James. He was the one that was running jobs by himself and I could see why he was good at it. He knew a lot of the people that were there to see the band and they all came to say hi to him, not the other way around. He was confident without being arrogant and seemed comfortable talking to everyone from their company’s banker in a nice oxford shirt and slacks all the way to the stone mason that was missing 3 teeth and had holes in every piece of clothing he was wearing. He had a great sense of humor that he changed and melded to whoever he was talking to; rough and curse heavy with the mason to witty and refined with the banker. He was intelligent but didn’t flaunt it or speak over anyone’s head, and, most of all, he seemed incredibly genuine and nice even when poking fun at others. Everyone loved him, that was easy to see, and I found myself listening more to the conversations he was having with people than to the band. He had a very laid back demeanor and even when a few people told him about problems they’d encountered on jobs earlier that day he never seemed stressed and was quickly able to put everyone’s mind at ease with solutions that even experienced workers seemed not to have thought of. I was impressed.

Eventually the flow of people stopped and he was able to sit and enjoy the music uninterrupted. Of course, shortly after he’d settled in the band ended their first set and took a break. I imagined he would go mingle with some of the people he knew but instead turned towards my dad and me.

“So, as a connoisseur of live music, your thoughts?”

“Well I wouldn’t say I’m a connoisseur, but they’re good! They sound great and they’ve got a good variety which is always nice.”

“I told them the only decade they’re missing is the 90s. They need to all bust out some synchronized dancing to a boy band song and then their set list would be complete.”

“Hahaha oh man that would be worth the cover alone!”

“Right?! I mean are you in the entertainment business or not?”

I was suddenly more aware of my attire for the evening and wished I had worn something a little cuter. It was just a night out with my dad so I had thrown on a pair of shorts, a plaid shirt over a white tank top, and grabbed my favorite baseball hat to try to hide my hair that I hadn’t washed that morning. I didn’t look bad, but I definitely didn’t look cute enough to feel confident talking to James.

The two of us bantered back and forth having a great time. He was so easy to talk to and he just made me feel so at ease about everything. If he didn’t keep bringing my dad into the fold I would have thought I had a chance with him rather than it being just a friendly conversation.

At the end of the night he said goodbye and headed off to his own car. I watched him go, kind of wishing I was going with him. He had to have a girlfriend I told myself, there was no way a guy like that was single, he was everything a girl could want and more; at least he seemed to be for the few hours I’d known him.

As we were quietly walking to the car my dad commented, “You could do a lot worse.”

“What?” I asked, shaking myself out of my daydream.

“James. You could do a lot worse.”

“Dad! I just met him! He’s nice and all but I don’t know him that well.” I said, hoping he didn’t actually see how infatuated I had become over the past few hours.

“Yeah, I know, I’m just…throwing it out there.”

“Well thanks for the vote of confidence but don’t hold your breath.”

That’s when he gave me the look, you know the look; that look that a parent can give their kid that says ‘I know you’re not telling me everything and that’s fine, but just know that I know.’

“Really?! Was I that obvious?!”

“Haha no, honey you were fine. I just know when you’re interested in someone. You have a tell.”

“A tell?! What tell?”

“Haha you never have your hair down unless you’re looking to impress a guy or it’s a formal event.”

I had been wearing a ponytail and a baseball hat when we got to the bar. I didn’t even remember doing it, but at some point I had let my hair down. When did that happen?

“Well that’s embarrassing. I doubt I’ll see him again though, there’s not a lot of cause for us to cross paths.”

“Well…do you want to see him again? He goes to all of their shows and they’re playing at the bar again in a few weeks for a fundraiser. You could come back.”

“Thanks but I think I’ll pass on the flirting in front of my dad option.”

“Who said I was coming? Just wander in.”

“Alone?! …Oh my god my dad is trying to set me up. Do you really like him that much?!”

“Haha no, he’s fine, but you seemed to hit it off so I was just trying to help.”

“I’ll think about it. Don’t tell Mom, she’ll badger me to go nonstop regardless of who it is.”

“Badger you?! You don’t think I’d get ten thousand questions about him since I know him? She’d be upset I didn’t know his social security number already.”

“Haha yeah but at least you aren’t the one that’s disappointing her by not being on track for grandkids anytime soon.”

“Eh, don’t worry about her. You do whatever makes you happy.”

I had said I would think about it but I already knew I was going. It had been a long time since I’d felt this giddy about a guy and regardless of whether he liked me back or not I just enjoyed being around him and wanted more.

It was a good thing it was the weekend because I couldn’t turn my brain off to fall asleep. I kept replaying the night in my head and getting butterflies in my stomach every time I thought about those beautiful blue eyes looking at me. He had shorter dark brown hair that seemed to naturally fall in a semi messed up but stylish fashion, a squared jaw line with a day or twos worth of stubble, 2 adorable dimples at the edges of his mouth every time he laughed, and a smile that made my heart flutter. Beyond his attractive face, he was in great shape. He stood about 6’3″ I guessed, and I could tell from his tight fitting shirt that he had a great chest and abs to go along with his toned arms. I had never noticed them on anyone else before, but his forearms were incredibly distracting; they weren’t huge or anything, they were just perfect the way the muscles flexed and rippled as he used his hands. I would have loved to just run my hands over his forearms as he moved about, feeling the muscle move beneath my fingers. All in all, he was hot, there was no getting around it, and yet that was just a bonus to everything else about him.

After lying in bed daydreaming for a while, I finally drifted to sleep. When I awoke the next morning I found myself incredibly horny; whatever I had been dreaming about clearly had me riled up. I slowly let my hand drift down my stomach and into my pajama bottoms while I slipped into a fantasy of James taking me home the night before. It wasn’t long before I rolled over and grabbed my vibrator from my nightstand and flicked it on. I kicked off my pajama bottoms and laid back with my legs spread, giving myself full access to my already wet pussy.

Over the past year and a half of being single, and not getting laid, I had begun experimenting more on my own. Up until now I had been pretty plain in bed and during our big breakup, my ex had called me boring and lifeless during sex which had really bothered me. I didn’t want to be one of those missionary only people, it just sort of always ended up that way. I had never felt super comfortable during sex as far as letting go and just ‘letting the freak fly.’ I had always been worried what people would think of the noises I made or judge me if I liked something they didn’t and, as a result, my boring sex life had become a product of being too safe. After the breakup I told myself I was going to try to change that and started by slowly experimenting with different things.

I had bought my first vibrator which quickly became a favorite of mine during my solo adventures. I had also tried masturbating in different positions, but never could get myself off as well as just laying on my back. Lately I had begun looking up other things I might be able to try. I thought I might enjoy bondage with my submissive personality, but that wasn’t really something I could try on my own, and the idea of asking someone about it still terrified me. Maybe I would enjoy rougher sex? I had never gotten so into sex that it became a sort of frenzied, lust filled fuck; I couldn’t get out of my own head enough for that. I tried watching porn but I always ended up with my eyes closed fantasizing and just using the noises from the porn to help with my fantasy.

Maybe I was just boring? What if I just didn’t like anything but boring sex? The thought terrified me. I didn’t want to be boring, I wanted to be the girl on top, slinging her hair around, moaning, talking dirty, exuding confidence and passion, and having a guy look at me with pure lust; but that was so far from how I felt that it might only live in my imagination.

After a few months of reverting back to my old boring ways and not experimenting for a while I decided I would try one last time to find something to get me out of my shell. I lived alone, but I had still had a feeling of anxiety like I might get caught when I had started browsing amazon for an anal toy. I was skeptical that I would enjoy it, but it was something I could do on my own and definitely fell under the ‘not boring’ category so I had to give it a shot. I settled on a thin dildo that had good reviews and said it was perfect for beginners. I made sure it came in a nondescript package and placed the order. It had arrived just 2 days ago and I’d quickly shoved it in my nightstand drawer as far into the back as possible, already having second thoughts and concerned that someone might find it and judge me.

As I fantasized about James taking me home and having his way with me, I let my vibrator slip up and down my pussy, purposely avoiding my clit, and just enjoying the sensations and feeling of being so turned on. As the tip dove down to my entrance my fingertips lost their grip on the end of the vibrator and it slipped from my grasp. As it fell I was able to catch it, trapping it against my pussy with the tip pressed gently against my ass. I gasped as a shiver ran through my body and my muscles clenched.

I was surprised how intense the sensation was. I decided this was my moment; if I was going to break out of boring, that shiver was the catalyst to get me there. I began slowly rubbing my clit with my hand as the other moved the tip of the vibrator in small circles around my ass. It felt amazing.

After a short time I pulled the box with the dildo from my nightstand and tore it open. I grabbed my small bottle of lube from my drawer and coated the dildo from top to bottom and rubbed the leftovers on myself. I tossed a few pillows under my hips to try to keep my sheets from getting too messy with the lube and laid back. I took a deep breath, closed my eyes, and tried to fall back into my fantasy. I brought my vibrator up to my clit while my other hand lined the dildo up with my tight hole. I tried to get out of my own head and not think about what I was about to do and eventually succeeded in focusing more on the vibrator than anything else. I started to push. Slowly I increased the pressure bit by bit until suddenly the pressure gave way and the dildo sank into my ass. It had only penetrated me an inch or two but already I knew I was going to like it.

As I sank each inch further into me I felt the pressure build inside of me. I couldn’t believe how big this thin dildo felt and soon I had the entire length up my ass. I left it there, unmoving for a minute, two minutes, three minutes, just taking in the feeling of having my ass filled with a foreign object. I realized in that moment that my pussy had become sopping wet. A smile spread across my face as I realized I had found it; I had found what would get me out of my boring routine and make me more exciting in bed: I enjoyed having my ass filled.

I could feel my orgasm building as the vibrator swirled around my clit. I reached down, grabbed the end of the dildo and slowly pulled it out inch by inch until very little was left inside me. The sensation was very odd, it felt like I was relieving myself, but all of my nerve endings were super sensitive so I felt every last inch in a far more erotic way than normal. As I pushed it back inside me a moan escaped my lips. I never made noise while masturbating, never, but something about having my ass penetrated deeper and deeper made me involuntarily squirm and moan.

Before I knew it I was writhing on my bed, my knees clenching and unclenching as I began fucking my ass for the first time. It didn’t take long for my orgasm to overtake me and my entire body to go rigid as the tremors swept over me. I had never cum like this before, my body shaking and out of my control, a long guttural moan escaping from inside me, and my mind completely lost in the waves of pleasure. Through it all I continued reaming my asshole and even once my orgasm subsided I didn’t stop. I loved it. The sensation, the dirtiness of it, the liberation of knowing I wasn’t boring, and then the thought of a dick pounding my ass, it was all overwhelmingly hot.

In the end I came three times; the final time from nothing but the dildo in my ass. I collapsed back onto my bed, the dildo still partially inside of me, and started to laugh as what I had just done swept over me. I laughed in relief, I laughed at how lost in the moment I had gotten, and I laughed at how I had just gone from the girl that was boring in bed to the girl that was going to be fucking herself in the ass on a regular basis from now on. It had been quite the morning.