It's Complicated Ch. 00: Prologue

Ashlyn Masters

"Yo Theo, where the hell are you going this early in the morning? Doesn't work ever let you sleep?" I ask my brother, who is always is just in a nice flashy suit with a silk red tie I got him last Christmas. He gives me a small smile, ruffling my hair like used to do when we were kids.

He may have been three years older than me, but that didn't mean he's mature. He still acted like a vibrant sixteen year old boy he once was in highschool. He actually looked better than he did in highschool, to be fair in highschool my brother was mostly the dorky one. He skipped grades, read in the library during lunch, was always in those braniac things the school had, and the worst of all the way he dressed and had these braces. Not only that his hair was way shorter— it didn't suite him at all.

"Stop it," I whine trying to get away from him. He lets me go even though we both know he could've easily kept me contain. "I plan on going out later to get a dress for the mask ball tonight. The one your works hosting? You better make sure you get to dance with me. That is if you can tell which dress I'm in," I say winking to him. He wouldn't know what dress I'm wearing since I didn't even know what dress I'm wearing.

"Oh, you plan on going to that?" He asks me scrunching his nose up. "I don't know if I'm going to it or not. They mask ball seems kind of cliche and overused, don't you think? They need to come up with something original."

"Maybe you won't go Theo, but I don't pass up an opportunity to meet the perfect guy. Tall, dark, and of course handsome," I tell him in a dreamy voice. I've always had the masked ball at his work planted in my head as arriving as Cinderella and finding my Prince Charming.

Jumping up to sit on the wide counters, due to the fact my brother loves to cook, I reach over into our fruit bowl of fruit. The almost completely bowl is limited to an apple or a banana. I chose the apple since I've had a banana the past few days.

"Maybe I'll go tonight. I'll surprise you. I have a few extra suits at my work in case I need to stay an over nighter. Anyways I gotta go now sis. Duty calls," he tells me, giving a small wave as he heads out the door.

"Yeah, more like over night with that office slut you guys have over there. I know what goes on, Tony ends up giving me all of the details whether I want to know or not!" I yell out the door to him, he's already in his car pulling out in reverse. He stuck his tongue out at me before he heads off to the direction of work.

With Theodore gone I think what sort of dress I'm getting. Most people have but they're going to wear in and out for weeks ahead. I am obviously not one of those people. Grabbing my keys to my car that my brother gave me for my twenty first birthday a few months ago I head on over to some of the smaller thrift stores in town. Just because my brother had money didn't mean I found the need to go to the most expensive stores and spoil myself. Pretty much all of my clothes are all from the thrift store. My brother always complain that I needed to go and get myself something nice every once in a while. Unlike myself my brother didn't mind flaunting around his wealth— especially when it attracts a bunch of gold diggers. Romantic dates that are expensive, the promises of the things he'll get her, he brings her to a motel or her apartment, and the next day he's done with her. He makes sure he tells them upfront how horrible they are to sleep with him thinking that it'd advance in a relationship. Overrall my brother's a really attractive guy now, he just can't seem to find the right kind of girl.

Almost driving right past the thrift shop I take a sharp turn to the left which emerged multiple honks and people swearing at me as I turn into the small parking lot. I just shrug my shoulders. Sure I almost drove past the place, but the green light indicated that it was my turn to go.

Smiling at the beautiful day outside, despite the morning chill of the October weather I skip inside to the thrift store. I went to these places almost every other week buying a new piece of clothing, which ultimately meant I got rid of some clothes as well. With the approaching winter weather and the deadly chill I often found myself giving the clothes to the homeless folks who could use them during the winter. Tearing them apart and making a blanket or a coat. It felt good to do something for them. Sometimes Theodore and I would bring a bunch of leftover food to where they live in the downtown area. Often you could spot one laying in the alleyways. After all that's where most of them live in cardboard boxes, all of them held their own story. Some people were out there just because they love to travel and see the adventures the world would bring them.

During the harsh cold winter months my brother would often throw a charity event in honor of the homeless where we raised money, invite the homeless, we provide them with food, and for the whole month my brother pays for them to live in the hotel and get whatever they want - he'd pay. None of them ever took advantage of his kindness.

Being one of the richest and youngest guys in the world it also makes him a bachelor. Young, handsome, successful, and of course very caring in the community. We only ever bought organic food, eliminating most of the times all of the chemical food. My brother has even started a greenhouse and a compost as well where we're going to try having a garden in next year. My brother is very busy, but the evenings unless there's an event our always scheduled for him and I.

Walking into the thrift shop I felt a small rush of excitement. I practically knew everyone in the store, how could I not? I memorized their names and we even talk when it's not too busy. Being the early morning and just waking up, most people probably wouldn't be out of bed. If they were they probably were working.

"Hey Lissa," I tell her as she sits behind the cash register, a new romance book in her hand always, the look of awe in her eyes as she reads it. She takes a few more minutes looking at her book before she sets it down on the counter.

"Ah, Ashlyn how wonderful it is to see you again. How are you and is there anything I can help you look for today?" she asks me and I give her a devilish look. Though everything in this store is categorized and put in different sections I still needed help finding everything in here. I just seem to forget where every section is during the week.

"Of course I need you help Lissa. I don't know what I would do if I didn't know any of you guys. I need help looking for a beautiful dress and a mask for tonight. I'm going to a mascarade ball at my brother's business. He's in charge of the whole thing yet he pays people to come up with an idea. One he finds over used. All I know is I hope to meet my Prince Charming tonight. I need a dress and a mask that make me different from everyone else," I tell her in a dreamy state excited for tonight.

I haven't had a boyfriend in a few years, after my best friend was killed in a car crash I started distancing myself from him and then eventually broke it off completely. He understood and told me that he couldn't wait for me, I accept that. We're both still friends and send emails to each other throughout the day spontaneously. He has a steady girlfriend right now and they're both going to the same college for culinary and business. They both talked about opening a restaurant together once they both finish college. Both of them come from wealthy families.

"I think I may have the perfect dress for you. You'll absolutely love it. Just stay here and let me get it. It hasn't been put out for sale yet. I'm glad I haven't now that you're here. It even has the perfect mask. It's a glittery gold mask that covers half of the face. I even have some make up I could do for you as well if you want," Lissa offers me and I give her a smile.

"That'd be wonderful. Can I put all of this on hold? I plan to get my hair trimmed, layered, and curled then I'll arrive back. Will you still be here in about an hour?" I ask her and she nods her head. Screeching excitedly I give her a tight hug darting off.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Later that night I arrive to the event taking a cab since I plan to have more than a few drinks. Stepping out of the cab I feel wonderful with my gold attire. My dress came down a few inches below my golden heels dragging on the ground, the corset holding it tightly together in the back. My chest seems perky and my breasts were pushed together making my cleavage look better. No bra is worn and I totally went commando tonight. I gathered quite some glances as I walk up the steps into the event. Everyone wore a mask, it sent a small thrill to me. I couldn't believe I'm actually here, I wonder if my brother would show up tonight. Considering he hates going to his own events probably not.

Lots of attention from males I gathered, some of them bold enough to address me and ask me to dance. None of them stuck out to me though. I decline each of them properly and I could see the look of disappointment on their face. They go back to their waiting date... who's not very impressed. Smiling at everyone I make my way over to the three tables that is loaded with all sorts of food near the wall. I take a glass of champagne and accidentally run into someone who's holding a glass. The champagne tips out of the glass falling out onto the floor. None of it making contact with my dress or his suite. My eyes meet vibrant brown ones that have a small sparkle to it. The guy let's out a chuckle.

"Does someone as beautiful make it a habit of running into people? I mean I certainly don't mind, I spotted you all the way from across the room," his deep voice says with a slight slur, but he didn't seem overall drunk. "Then again for the looks of it I think of a lot of people noticed you. After all you're the most beautiful girl here tonight without a doubt."

"You look quite handsome too. Would you like to dance? I mean it's the least I could do since I almost spilled my drink all over you. No harm is done," I tell him smiling and he smiles carefully taking my hand, a slow song approaches and we dance for a while. One of my favorite songs, Give Me Love by Ed Sheeran.

The night seems to fade away, but there's an unknown chemistry between me and this mystery guy. We could've been dancing for minutes or hours, I couldn't tell the difference. All I know is he began drinking some more and I joined him. We both talked a little about ourselves and I enjoy myself for the first time. I've never had this much fun with anyone. Every glance he gave me made feel special, like I'm the only person for him. Knowing it wouldn't turn into a relationship I decide to try to go for a fling. Eventually as the party seems to disperse I give him a smile and look at him.

"Would you like to hit a motel and have some fun?" I ask him and he shakes his head yes grabbing my hand eagerly. Both of us have been waiting for this. The songs went from slow and sensual to plain out sexual. The sexual tension between to grow as we both we kissing and groping on the dance floor. Cabs were showing up to grab the drunken people and he hijacks one of them pulling me into it, I fall on his lap and begin kissing his neck. I didn't care if the taxi driver saw or not. He looks at us with little interest. He talks to the driver letting out a low moan as I nip at his neck.

"Motel please," he says and the cab driver nods his head taking to the closest one which is around the corner.

Stumbling towards the front desk we paid for the night and headed towards the room. He slams me against the wall kissing my neck, my dress being scrunched upwards as his hand eagerly goes towards my sopping wet pussy, rubbing the outside of my lips. I moan eagerly, grinding against his hand. We both only separate long enough so we can unlock the door to the room, he picks me up and pushes me on to the bed, I watch as he unbuttons his shirt, the only light provided from the small night lights that are in the room. Suddenly I speak up as he's about to take his mask off.

"No, only for tonight are we allowed to keep the masks on. Tomorrow morning we can both take them off," I tell him and he nods his head speaking in a hoarse voice. If he's still here in the morning.

"Yes ma'am, now get up and turn around so I can take that lovely dress off of you," he says and I nod my head turning around. He slowly unties the corset and slips the gown off of my shoulder, it collapses on to the ground. "Mmm, no underwear or bra... what a naughty little girl. Get on your knees and pull my slacks and underwear down. We're going to have quite a long night Kitten. I don't plan to let you rest at all."

I go straight to my knees slowly undoing his belt pulling it down with his underwear all down in one swoop. His cock pops out nice and hard, quite thick and maybe two or three inches less then a ruler. I've had my fair share of cocks throughout the few years I've had sporadic boyfriends. All of theirs has been gross looking. His looks nice with a perfect pink mushroom head and a vein trailing up from the bottom of his shaft. He seems to trim as the hair isn't wildly long, but it's not completely gone either. I didn't shave, instead every once in a while when the hair is out of control I trim it.

With small droplets of pre cum leaking out the tip of his cock I smile licking it, causing a small moan from the back of his throat. Spitting a little on his cock I begin to stroke him, holding my grasp loosely, but firm. Stroking half of his cock I take the head of his cock with no problem. I wasn't sure if I'd be able to get all the way down on him. He puts his hand on the back of my throat pushing me a little further down on his cock. I gag, but eventually get accustomed to it. Once his cock is well lubricated he pulls me off of it and I pout wanting to make him cum.

"What a good girl... mmm come over here and get on top. I want to watch your beautiful breasts bounce as you're on top of me. Not only that, I believe someone is going to get a spanking," he whispers playfully in my ear and I stand up pushing him on to the bed. Crawling on stop of him and straddling I take his cock firmly in my hands and rub it on the entrance or my pussy which at this point is drenched and more then ready for his cock to slide in. Teasing it deliberately he growls slapping my hand away and lines up his cock in my entrance. Pushing up I moan as he slides the first few inches in me. Working his way in slowly we both let out a moan as his cock is completely engulfed by my pussy. Pulling up so only the tip of his cock is in my pussy I slam down moaning loudly.

"Fuck... Kitten go faster mm... fuck... oh I fucking love your tight pussy. My fucking big cock fits in there so nicely, your pussy is so wet and warm... fuck baby keep going..."

Then we both reached the highest peak of our life. I cum, he cums at the same exact time. A strong spurt and then a few smaller spurts. I collapse on him tiredly, closing my eyes when he leans over in my ear.

"That's just round one baby... we still have all night too."