My Whole Life Pt 01

The usual stuff. Everyone having sex is over 18. No COVID, STD's or fathers with shotguns appear to dampen our day.

Warning: This story depicts graphic sex during a woman's period. Lots of bloody fun. I know this will not be everyone's cup of tea so get out now while you still can.

Matt was sitting at the kitchen counter enjoying a leisurely Sunday morning breakfast when he heard the door from the garage loudly open and then the inevitable crash as it was slammed shut. He wondered for the ten thousandth time why his sister was incapable of simply shutting a door. He supposed it went back to when she turned fourteen and the hormones had kicked in. Everything was about her and very dramatic, she hated her brother, her school, her friends and especially her horrible parents.

Well, she didn't have to worry about their parents anymore. They were on a business trip when the small plane they were in crashed going from Cartegena to Bogota in Columbia. Their dad was a lawyer specializing in international business law, while their mom was his secretary. That was how they met; he was a summer intern at the law firm where she had just started as a paralegal. Love at first sight, they got married two months later and were, as his sister jeeringly pointed out, disgustingly happy. He could never quite figure out why being happy was disgusting but that was his little sister.

When they went to the family lawyer, Dan Wilson a friend of their dad since law school, for the reading of the will, they both got a huge surprise. They had assumed an even split with a court appointed guardian until they were eighteen. It didn't matter to Matt; he was an eighteen year old senior in high school. Kylie was fifteen and certainly needed someone to try to keep her on the straight and narrow.

The will was in the form of a video taken in the office they were sitting in now. The date flashing in the corner indicated that this had been made just over a year ago. Dad was never one to beat around the bush and he didn't do so now.

"Hi kids, if you are watching this yadda yadda yadda. This is the fifth one of these we have done. We intend to make one every two years to keep current with your ages and our financial situation. Here's how we want this to work. Matt gets all the money and control over all assets of your mother and me. Kylie gets a trust fund with an initial 2 million in it. It will be administered by First National bank. She will not have access to it until she is twenty five or she has been married for three years. Yes Kylie, we mean to the same guy. Three years of waiting should discourage any gold diggers trying to fuck you in more ways than one."

"Robert that was unkind and uncalled for," she said gently slapping his arm. She turned back to the camera saying, "But your dad is right no matter how crudely he put it. There will be a lot of guys trying to separate you from both your virginity and your money. I suggest you never let anyone know about your financial situation. IE, it would make a nice wedding present to your husband if that was the first he heard about it."

"With that in mind we suggest selling that monstrosity of a house and buying a more modest one.

"Now, if your sister has come down off the ceiling after learning she has only 2 million dollars to rub together, we will explain why."

Mom took over at this point and said, "Kylie dear you spend money like a drunken sailor on leave. We have discovered that the only way to rein you in is by controlling the amount of money we give you. Matt, you need to do the same. She needs a car when the time comes, not necessarily a new one, phone, clothes, food and a home. She does not need trips in or out of the country with her so called friends. I know she is only fourteen now, but boys will be entering her life soon. Kylie do not pay for expensive things for a boy. Sure, the occasional movie or meal but that's it."

Back to dad now, "Matt, I know you are only seventeen now and I pray that you never see this video, or the next ten after it, but shit happens. We want you to finish high school then put off college until your sister graduates and goes to college. She needs someone strong that knows her like you do to keep her on track. It will be difficult, what am I saying, nearly impossible to keep her out of trouble entirely but that is what big brothers are for. Think of it as good training for when you have kids."

"There is more than enough money that you wouldn't need to work but the idle rich draw attention to themselves. Get a decent paying job when you finish school. Something you have an interest in, I would suggest that as much as you like getting your hands dirty a construction job would suit you. It will give you some place to go during the day, an income and a relief from the gossips."

"When I say there is money, I am talking about 15 million bucks right now. It is invested, hopefully wisely, with various institutions and should earn a yearly income of nearly a million dollars. Dan has the details for you Matt," dad told them.

"Well, that's about it, we love you and hope for nothing but the best for you both," mom said.

"Same here guys," dad said looking sad.

"Kylie, if you ever become more than your brother can handle he can, and will, pass guardianship over to Aunt Bella. As you know she lives on a ranch in Wyoming over 70 miles from the nearest town. School is online with no sports programs. So, unless you want your running companions to be rattlesnakes try to take it easy on your brother. This is all new to him also," mom concluded.

"One more thing Kylie. Don't even think you can contest this will. Any lawyer you can find worth his salt will tell you that a will drawn up by Dan Wilson is not breakable."

Kylie squirmed in her chair clearly put out that her dad had seen through her intentions from beyond the grave. Matt just sat there thinking things through.

Dan Wilson reached over and clicked the video off. "I'm sorry kids, I hope you know this is not just business for me. I genuinely cared about your folks, I will do whatever I can to help guide you through this."

"Ah, it's a lot to think about," Matt said numbly. "I need, we need, to talk things over before making any decisions."

The drive home was quiet, both thinking. Matt about his new responsibilities and Kylie about finding a shyster lawyer to help her get her share of the loot.

After thinking it over for a month or so Matt told Kylie they were selling the big house and moving. He had found what he thought was the perfect place on the edge of town. She threw a fit because that would be in a different school district, she declared she wasn't going to move her junior year. He smoothed things over by letting her get her license the day she turned sixteen. It took her three tries to pass but when she did, he bought her a Porsche Cayenne SUV. It was only two years old but when she complained bitterly about having to drive an old piece of shit, he used the spare key to take it from the school parking lot straight back to the dealer. She called in a panic after school saying her car had been stolen. He explained what he had done and hung up. Instead of being in a rage when she finally got home, she apologized and asked if maybe they could go get her car back. It wasn't much but it felt like a huge victory for Matt.

Matt wanted to take his dad's advice so after graduation he stopped at a large construction site to see about a laborer's job. As he was walking across the site he heard a horn, turning to look he saw a high school friend jumping off a backhoe and coming toward him.

"Jesus," Jimbo said, "what the fuck are you doing here?"

Matt explained and Jimbo said. "Fuck that, tell them you are a backhoe operator, this is a nonunion job, so they don't check with the union hall. Being a laborer sucks man."

"That sounds good, the only problem is that I have never been on a backhoe in my life."

"No sweat man, we will go in and talk to the foreman and get you hired. Tell him you can start next Monday then come here at 5pm and we will start lessons, I have keys for everything and by Sunday night you will have about 30 hours of practice under your belt," Jimbo explained.

"Shit man 30 hours is nothing, I can't be a good operator on that little time."

"No, you're right but I have an easy job for you. In fact, we will only spend a few hours on the backhoe. What I need you for is to carry sand and other material to the back side of the building in the skid steer, you know, a Bobcat. The access is too narrow for anything else. I know I can teach you how to operate a skid steer by Monday. Unless you are a total retard," he said playfully punching Matt's arm.

So that had been Matt's life for the last three years. He was now known as one of the best small machine operators in the city. It was satisfying work, he was thinking of doing this the rest of his life. College just didn't appeal to him at all anymore.

His life with his sister was ok, it had its ups and downs along with huge shouting matches and slamming doors, but she was finally eighteen and would graduate in a month. In only four months she would be off to Stanford on a volleyball scholarship.

They had talked about selling the house now that it was going to be only Matt, but Kylie had fallen in love with the house and had decorated it to suit her lifestyle. She said she would like to know she had a home even from California. There was plenty of money. They were able to live on Matt's salary and just a small amount of help from the investments.

Matt didn't have a girlfriend, he had never had a long term one. He picked up a girl from the bar they hung out at after work now and then, but it was never serious. Working hard outdoors had given his 6' 2" 190 lb. frame some nice muscles and an envious tan. The girls seemed to like him, but he never let them get close.

He never really thought about why until he had a fight with his sister about him bringing home 'a fucking bar bimbo' on Friday night and not taking her home until Sunday afternoon. His sister sounded like she was jealous and trying to make him feel bad. Like she was one to talk. Since she had started dating at sixteen, she had never had a guy stick around for more than two months. He had never figured out why, at 5'8" and a thin runner's build, she didn't have a steady boyfriend but that never happened. He just chalked it up to her obnoxious personality.

Since that blowup he would go to the girl's place or get a motel. It didn't really help as his sister would grill him about where he had been when he got back to their house.

Then life changed when he started a job on a new building in the center of the city. Like most downtown sites there was very little room. Matt was given his usual job of getting supplies and material into the tightest places.

Suzy was a tomboy looking girl that swore like a trooper. She was the foreman on the labor crew that was doing the filling and tamping along the back wall. She called Matt every name in the book for the entire week but then asked him if he wanted to grab a beer on Friday night.

"Why, so you can heap more abuse on me? No thanks dude," Matt said shaking his head.

"C'mon man, I yelled at you like I do my crew. They don't take it personally and neither should you. It's partly my personality and partly because I am not a dude, I handle things by insulting everyone," she explained quickly. "You did notice that I'm not a dude, right?" she shyly smiled at him.

Still thinking he was being set up somehow, he told her, "One beer, at my bar, agreed?"

"Sure, whatever you say man, name the place," she agreed quickly.

"You know The Spot on Westminster?"

"Sure, it's on my way home. I'll meet you there in like twenty?" she asked.

"Sounds good, see you there."

All the way to the bar he looked for angles and reasons she would suddenly change her whole demeanor. Finally, he shrugged thinking he would know soon enough. He parked and came through the back door spotting Jimbo first thing and going over to say hello. They talked a minute before Jimbo waved his pitcher at him. Matt declined saying he was meeting someone and would be back over later.

He sat at an empty booth and waved at the waitress. She smiled at him and in a minute brought over a pitcher of beer and a tray of mugs. He was about to tell her two mugs when Suzy set a pitcher and two frosty mugs on the table.

"Great minds think alike apparently," Suzy said with a smile. "Looks like we might have more than one drink."

They drank the two pitchers then ordered another with some wings and fries. When the food was gone Matt divided the last of the beer between their glasses.

"Ok, now that we have had a meal and a few beers it's time for you to get to the point of this little soiree."

"I wanted to ask you out the first day I saw you. But mixing work and pleasure is not usually a good idea," she said.

"That is very true, so why are you doing it now?" he asked.

"Because today was my last day on this job. My boss needs me to ramrod another site that is way behind schedule so today was my last opportunity."

"That's it? No hidden agenda?" he asked carefully watching her face. "Wait, there is isn't there? An old boyfriend in the back lot? A jealous husband?" He started to slide out of the booth.

She frantically grabbed his hand quickly saying, "No, no nothing like that. Please let me explain," she begged him.

He sat back warily and nodded for her to go on.

"No boyfriend, no husband, no one at all really. I seem to chase away every guy I ever meet," she said with a catch in her voice.

"So, what do you want from me?" he asked.

"I have a few, I guess you would call them fetishes, that excite the hell out of me but absolutely turn guys off," she said with her head down.

"And you thought I would be the one guy that got into your kink? What is this bizarre behavior you like to indulge in?"

"I love to have sex when I am, ah, when I, shit, when I am on the rag," she blurted out.

"Wow, what made you think I would be into something like that?" he asked with a frown.

"I don't know, maybe because you seem like a rugged guy who could handle a little blood. Or would be willing to at least try to help a girl out."

"So, what does this involve? You want to be fingered, fucked, maybe even eaten while bleeding?"

"Yes, oh yes, all of that," she said closing her eyes and tilting her head back. One of her hands slid off the table onto her lap and just seconds later she started to convulse in orgasm. She slowly recovered and opened her eyes. She had a sheepish grin on her face and let out a long sigh.

"Fuck, I have never seen anything like that," Matt said astonished at her behavior. "So you are having your period right now and you just had an orgasm in like ten seconds, is that right?"

"Yeah, I'm on the rag and I just rubbed one out and now blood and cunt juice are leaking from my pussy."

"Do you always get horny when it's that time of month" he asked.

She laughed saying, "I know, ironic right? The times I really want a cock in me is when I'm pouring blood."

"If you want me to help you out you are going to finger your cunt then show me your bloody fingers," Matt said sternly. He had no idea where this came from but both his demand and the thought of her showing him turned him on tremendously. He expected her to go to the restroom then come discreetly back to the booth.

Now it was her turn to look at him closely. Was he going to embarrass and humiliate her as payback for the way she had treated him all week? A little thrill went through her as she thought about all the construction workers, many of whom she had worked with, seeing her bloody hand. With a little moan she unzipped her jeans then scootched down in the booth to get a better angle. She had intended to just stick a couple of fingers inside her wet cunt but then realized it was not only blood causing the wetness. She kept two fingers inside her while using her thumb to rub her fat clit. It gave her almost instant relief and after nearly biting her lips off trying to keep quiet she carefully pulled her hand from her jeans and casually straightened up leaving her jeans open and pulled down her thighs a bit.

Nonchalantly she put her hand on the tabletop saying, "It's not as red as I would have liked. The blood got mixed with my cunt cream when I came, sorry about that," she said staring at him.

Matt couldn't take his eyes off her small, calloused hand lying there in the open with dark red and pinkish streaks covering nearly her whole hand. He shook his head in a daze then looked up. "Ok, now I am going to finish my beer. You are going to wash your hand in your remaining beer then we are going to my place and explore your kink and some of my fantasies."

Suzy smiled hugely then dipped her hand in her mug eagerly washing her hand. Matt finished his beer then started to exit the booth. Suzy pulled her hand from the mug then brought the pink concoction to her mouth and chugged it. She reached down pulled up her jeans and snapped them. With a grunt she slid out then stood up. She looked at Matt and burst out laughing at the priceless look on his face. Taking his arm she led him out to the parking lot.

"Ok, you said you wanted to go to your place but believe me it is better if we go to mine. I have rubber sheets and a bunch of towels I use just for this time of month. Did you want to swing by your place and pick up enough stuff to carry you through the weekend?"

Still somewhat dazed Matt said, "Yeah that might be a good idea. I can meet you at your house or we can follow each other to both places."

"I'll just meet you at my place. I'll text you the address. No need to change or shower. Trust me, we are going to take a lot of showers this weekend," she said with a wink.

Matt was a little preoccupied as he drove home. He had always wanted to have sex with a menstruating girl. It all went back to the first girl he ever fucked. They had fumbled around in the back seat until the parts lined up then he went for it, lasting about ten strokes. They had dressed then went to an ice cream shop to hang out. When the girl came back from the restroom, she insisted they leave immediately. In the car she told him she had started her period a day early, probably because he had taken her virginity. Since then he had associated sex and bleeding. He had never felt confident enough to ask a girl to have sex when she was menstruating, so he was really looking forward to being with Suzy.

Matt's sister's car was home when he got there but he didn't see her downstairs. She sometimes dropped her car at home before jumping into a friend's or boyfriend's car. He went to his room and threw a few clothes and his shaving kit in a backpack then headed out. He stopped in the kitchen to leave a note telling Kylie he wouldn't be back until late Sunday. He put it on the refrigerator with a magnet then turned to go. From this angle he could see his sister sunning herself by the pool, so he went out through the sliding door to tell her in person.

"Hey Kylie, I wanted to let you know I would be gone all weekend," he said cheerfully.

"Let me guess, you picked up a drunk skag at the bar after work?" she said bitchily.

"Actually, I had a few drinks with a female coworker, she invited me to her place for the weekend," he said evenly.

"Shit that's even worse," she said angrily, "a slut you fuck for a few days then you have to pretend to like her at work, god you are disgusting," she said getting up from the lounger.

"I don't know what your problem is but knock it off right now. I have the right to go out with whoever I want, it certainly doesn't concern you," he told her hotly.

"Right, like you would stick around if I needed you," she said pushing past him.