My Whole Life Pt. 02

The usual disclaimers. Anyone having sex is over 18. No STD's or pregnancies happen in my happy little world.

Reading part 1 is a good idea. Otherwise, this will seem even more disjointed than my usual offerings.

Matt had come home from his wild weekend with his coworker Suzy and headed straight for bed. He slept most of the afternoon before getting up to get his weekly laundry together. He had carried it all down to the laundry room to throw it in the machine when he noticed blood stains on the jeans he had worn to Suzy's place. He smiled at the memory of fucking the super horny woman while she was on the rag. He put the jeans in the laundry tub with cold water to let them soak.

He went up to fix himself a sandwich then carried it, a bag of chips and two sodas down to the family room. He had just finished his food when he heard the door from the garage open then slam shut.

Kylie had been for a run and was going to take off her running clothes, throw them in the washer then slip into the downstairs bathroom for a shower. She did this often enough that she kept a couple of pairs of shorts and tops in that bathroom. She had taken off her shoes and socks when she noticed a pair of her brother's jeans soaking in the laundry tub. She saw what appeared to be blood on them and went looking for him to ask what had happened.

She found him in the family room playing a game.

"Why is there blood on your jeans? Did you have an accident or get in a fight?" she asked.

"No fight, no accident. Well," he gave a short laugh "maybe a little accident. Nothing to worry about," he assured her.

"What do you mean nothing to worry about. C'mon tell me," she whined.

"No, it's none of your business Kylie," he said firmly.

"I knew it, you got in a fight over some slut," she said viciously, "I hope she was worth it."

"Oh for god's sake drop it. I repeat, I was not in a fight," Matt said loudly.

"So what happened to you then?" she persisted.

"Nothing, and I repeat, it's none of your business."

"I'm going to start calling all your friends until I get the story," she threatened.

"Call anyone you like. If you really cared you would know I don't see my old friends since I started working construction so that's a dead end," he said heatedly.

"It's not my fault mom and dad died and you have to take care of me and not go to college like your friends," she screamed.

"That's not what I meant at all. I just meant I have new friends now is all," he said softly.

"Jesus, are you gay? Are you sleeping with some guy from work?"

"Screw you, why would you even think that?" he said hotly.

"I don't really, it's just that you spend every night at some bar before you come home to me. I know you sometimes have a hookup with a bar slut but I...oh I don't know," she trailed off giving him a dirty look.

"You are not going to let this just drop, are you? Ok, the story is a girl from work, yes, a girl, asked me to have a drink with her Friday night. After a few drinks she confessed that she had a fetish she was hoping I could help her with. Turns out her kink is having sex while menstruating. She was having her period and really wanted to have sex. We got kind of carried away and I got some of her menstrual blood on my jeans. That is the truth but I'm thinking you didn't really want to hear it did you?"

"My god you are a disgusting pig. How could you make her fuck you at that time of the month, you are so selfish Matt," she said with contempt.

"First of all, I don't need to force a girl to do anything. In case you haven't noticed, I'm a pretty good looking guy. Second, she is the one that wanted to fuck, it's the reason she asked me over. Third, I did do her pussy and even ate it after I came in it. Fourth, that last part may sound a bit disgusting, but I certainly enjoyed it, and so did she."

Kylie stood there stunned by her brother's revelation. Finally she spluttered, "You had sex with a bleeding woman?"

"Yes, she said she gets very horny at that time of month then proved it. Out of curiosity, do you get horny at that time also?

"That is a gross thing to ask. Why do you want to know?"

"Like I said, just curious. So, is that a yes or no?" he asked smiling.

His smile and good looks suddenly got to her and before thinking she said, "Why, do you want to take advantage of your little sister and fuck her while she's on the rag? Is that how you get your kicks? By being a pervert and doing perverted sick things to your sister?" she yelled.

Matt sat there stunned. When he could find his voice he asked, "Where in the hell did that come from?"

I don't know," she said looking nearly as stunned as her brother. "You have never looked at me as a girl, a woman, you always look at me like I'm a nothing, just something you are responsible for, like a pet goldfish or something."

"Kylie, you're my sister, not only am I your brother but I am also responsible for you. I have never thought of you in a sexual way," he explained.

"Why not? Aren't I skanky enough, don't I dress slutty enough for you? Am I too skinny, are you into fat chicks or just sick twisted ones?" she was so worked up she was spraying spittle as she yelled.

"Where is this coming from? What's gotten into you? You have been acting even stranger than normal since you turned eighteen."

"So, strange but not perverted, is that why you don't look at me that way?" she asked.

"Look at you? What way? How am I supposed to look at you?" Matt asked very confused.

"Shit Matt are you that dense? I want you to look at me like I was someone you would want to take to bed," she declared.

"But I don't, I can't see you that way. Is this because you broke up with your boyfriend?"

"Oh, the hell with my boyfriend. He was just another in a long line or greedy, needy little boys," she said.

"It sounds to me like you need to get another boyfriend or at the least find someone and get laid."

"Jesus, why do you think I go through so many boyfriends?"

"Because you have a nice body but the personality of a pit viper?" he said honestly.

"Up yours Matt," she said giving him the finger. "The reason I can't keep a boyfriend is because I won't put out. You have always thought that I fucked them and threw them out, but I am a virgin."

"Wow, I never thought that you would still be a virgin," he said disbelievingly, then insanely added, "are you sure?"

"What do you mean am I sure? Of course I'm sure, what kind of a stupid question is that?" she said frowning.

"You have never had sex?" Matt asked just to be sure.

"I have kissed a lot of guys, I have let two of them feel me up but the only person, other than me, to ever touch my vagina is Dr. Jane Moore," she confirmed.

"So, why are you holding out? Don't you get horny? Are you into girls?" he asked her.

"Of course I get horny, I have a nice collection of toys that I use nearly every night. I have kissed a couple of girls, but they didn't do anything for me," she said honestly.

"So what, are you waiting for Mr. Perfect, a knight in shining armor or something."

"Yeah I guess you could say that," she said a little sadly. "But he looks at me like I am a pet goldfish."

Having said that, she ran for the stairs. He could hear her beginning to sob as she pounded up the stairs. A few seconds later was the inevitable crash of her door slamming.

Matt sat there stunned, he wasn't quite sure he had understood his sister. She wanted him to be her first, to take her virginity? She wanted her brother, that she just barely acknowledged and tolerated, to take her to bed? Is that why she was always so upset when he hooked up with a woman?

Other than being upset by any female he was ever with; she had never given any indication that she cared much about him. The only times she ever really interacted with him was when she was trying to weasel more money from him. Mom and dad had warned him about giving in to her in the video will they had left. He had not wanted to be the executor for the estate but there it was. He had pretty much learned to ignore her pleas for money, putting her off until she came up with another reason she simply had to have more money. They were more like roommates that tolerated each other than siblings.

He tried to get back into his video game, but it was no use. He was just stalling, putting off talking to his sister. With a sigh he shut the system down then gathered up his dirty dishes before taking them up to the kitchen. He cleaned up his mess then took a package of pork chops from the freezer to thaw. Quit stalling Matty you wimp, he said to himself.

The soft knock on Kylie's door was returned with a, "Go fuck yourself Matt, I never want to see your face again."

Matt sighed, "Ok, sweet dreams Kylie. I am making pork chops with applesauce and mashed potatoes for dinner, it'll be ready about 8:00."

That got no response so he headed down the hall to his room. As he reached his door he thought, fuck this, I'm going for a beer.

Jimbo and two other construction buddies were playing pool when he entered his favorite hangout, The Spot. "Shit, don't you guys have anything better to do on a Sunday evening?" he asked.

Jimbo, leaning on a cue stick, looked around exaggeratedly then shook his head, "No, no not really. And you?"

"Screw you, rack 'em up, Louie," he told one of the other men standing there.

An hour later, as he bent over to take a shot, he felt a slap on his ass. He thought it was one of the guys trying to ruin his shot, so he never looked to see who had done it. He missed his shot when the hand came back and firmly squeezed his right ass cheek. He turned to find a grinning Suzy holding out a mug to him, "I thought that might get your attention."

Matt brought her in for a hug saying, "What brings you here on a Sunday afternoon? It's not time for us to get together surely?"

"Nope, twenty-five days yet," she said. "I'm actually on a mission of mercy. You want to sit for a minute?"

Without waiting for an answer, she headed for a booth. She gave him another hug before sitting down. Matt slid in opposite her before asking, "Since when did you become an angel?"

See the girl in the booth behind me? The cute blond who is probably staring at you?" she asked.

"Yes, I do. She is staring and smiling at me, what's up?"

"Well, she's been my best friend forever, since preschool in fact. She just got divorced, the ink isn't even dry yet. The main reason they split after only two years was his lack of a sex drive. I take that back, not a lack of desire, a lack of being willing to have any type of sex other than missionary. Megan, that's her name, had just started to experiment with sex when she met him. They went out for two years then got married. End of experimenting and trying to get her ex to loosen up. Now that she is single, she wants someone to show her stuff. I thought of you right away," finally slowing down she said, "So, are you interested in helping her out?"

"That was a lot to take in, give me a second. Megan wants someone to show her sex stuff. Like positions, oral, anal, BDSM, what?" he asked.

"Yes," answered Suzy.

"Yes what?" he said frowning.

"Yes, all of the above, Matt," she nodded.

"Wow. In one session or a series of tutorials?" he said grinning.

"If you guys hit it off, a series for sure. She knows what she wants in this first lesson," Suzy said smiling.

"And what might that be?" he said, returning her smile.

"She wants to have anal sex," Suzy said.

"Holy cow, from straight missionary to anal with no stops in between? Isn't that kind of rushing things?" he scoffed.

"No, her thinking is that if you can be patient, give her a good experience with anal, then you would be an excellent teacher for the simpler stuff."

"So how did you know I would be here today?" he asked.

"I didn't, we were on the way to my place when I saw your truck in the parking lot," she said. "So, what do you think Matt?"

Matt sat silently for a few minutes before saying, "I suppose I should introduce myself to your friend."

Suzy smiled then taking his hand slid out of the booth. She guided Matt so he had no choice but to sit next to the nervously smiling blond woman.

He held out his hand saying, "As you have guessed by now, I am Matt."

Suzy started laughing then snorted when she tried to stop. "What the hell is wrong with you?" Megan asked.

"The way he said, 'I am Matt' reminded me of the Guardians of the Galaxy movies. 'I am Groot.'"

"Jesus, Suzy you have the strangest sense of humor, knock it off, this is serious," she scolded her friend.

"I thought it was a good ice breaker," Matt said smiling. "Suzy tells me you want to try anal, correct?"

"Yes, I do."

"I would love to be your teacher," he told her. "When were you thinking of having this lesson?"

"I gave myself an enema this morning, kind of trying out how it felt and how it worked so I am ready that way. I have a tube of lube in my vehicle. So I guess..." she trailed off.

"I like a girl that thinks ahead. Next question where would you like to do this? Your place, my place, a motel?" he asked.

"Ah, I was, well, geez, how about in the parking lot in my van?" she finally blurted out.

"You drive a minivan? How many kids do you have?" he said frowning.

Suzy hit his arm saying, "It's not like that. No kids, it's her work van, not a minivan. She has kind of been living in it since the divorce. He got the house; they were underwater on it, so she figured she would let it ruin his credit rating. She has an apartment as of the first of the month but until then her boss let's her crash in her delivery van."

"Well, the back lot is secluded so with Suzy as lookout we should be ok," he said.

"Lookout? Are you nuts? I want to watch this up close and personal. Next time we get together I want you to do my ass. I want to know what to look forward to," Suzy declared.

"I don't mind, what about you Megan?" he asked the blond.

"She was there when I sucked my first cock and in the next tent for my first fuck so what the hell, why not?" she said as she gathered up her things to leave.

"How about you two head out now. I want to check on my buddies then I'll be right out," he told them.

He walked up to the trio still playing pool and said, "If you don't go home right now, you are going to switch to hard liquor and try to drink the joint dry."

"And that would be a bad thing because..." Jimbo asked a little drunkenly.

"Because tomorrow is Monday, dude," Matt said. "How are you going to get home tonight?"

"I gave the bartender my keys when I came in. She will Uber me home when it's time to go," he informed Matt.

"You're going to be shit at work tomorrow, I'm glad we're not on the same site," he said laughing.

"They are pouring massive amounts of concrete tomorrow. My services are not needed until Tuesday," he explained.

"Well, good luck being sober enough to climb into a machine even by Tuesday," he said as he headed out the door to meet the girls.

A white cargo van was parked in the far row against the fence. The side door opened as he approached so he climbed in. The interior was a large space with no seats or dividers. It held what looked like four or five sleeping bags and a bunch of pillows. Two cardboard boxes looked to have clothes in them.

"The rest of my stuff is in storage until the first," Megan explained.

"It's very cozy, almost intimate," he grinned.

Suzy said, "Yup, just the right size for a butt fuck."

"If that's the way you're going to act get the hell out right now," Megan said hotly.

"Sorry," she said contritely. "No really, I mean it Megs, not another word, promise."

"Ok then," Matt said clapping his hands together, "First thing is to get our clothes off. I have been imagining what you look like naked, I'm done waiting."

He was naked before Megan had slowly pulled her sweater off. She turned her back to him before taking off her bra. She hesitated before unzipping her jeans then wiggling her butt got them over her hips.

Suzy said, "Oh for god's sake Megs, get your duds off and show him the goods."

Matt looked over at Suzy, somewhat surprised to find she was also naked.

Megan turned toward them before peeling her boy shorts down her legs. The girls were short enough to stand upright while Matt was awkwardly bent over.

He went to his knees saying, "Why don't you lie down, I'll take your shoes off."

He got her shoes and socks off then struggled a bit to get her skinny jeans off. The panties were much easier to remove. He went to his stomach between her legs saying, "As long as I'm right here I might as well do some exploring."

She had very small pussy lips that didn't stick out at all. When he parted them with a finger, he found them to be a pretty pink color. When he coaxed her clit to come out and play it too was the same color. Curious now, he tilted her hips back to reveal that her sphincter made it a trifecta. It was the absolute cutest thing he had ever seen. He dove in with tongue and fingers, not relenting until she had cum twice.

He came up for air leaving her a panting quivering mess.

Suzy chuckled, "I take it Matty here might be an adequate teacher?"

"Fuck, fuck, fuck, I have never cum that hard in my life. I think it was only the third time I ever had two O's in one day," she said dreamily.

"I think you can safely say that you're going to break that record today, probably in the next ten minutes," Suzy laughed.

"I want to return the favor, but I am kind of in a zone. Would you take my butt cherry while I am still so relaxed?" she nearly begged.

"Of course, where's the lube?" he asked.

She pointed to one of the cardboard boxes. Suzy nearly dove headfirst into it in her haste to retrieve it. She triumphantly held it up before taking the cap off then crooking her finger at Matt.

"Let's get that bad boy greased up there, big guy," she told him.

"Do you have any ideas about what position you want to try first Megan?" he asked.

"Yes, I want to be on my back with my heels behind my head. I can watch your face, your cock and my ass in that position," she said firmly. "I am double jointed plus I was a gymnast for many years." She demonstrated her flexibility by assuming the position she had described.

"Fuck me," Matt moaned, "I have died and gone to heaven."

"The only way to improve on this would be if you had a bloody cunt to munch on," Suzy said grinning.

"Enough of that kind of talk, I'll be cumming in your hand in a minute," he told her. "You want to get her butt ready, or you want me to do it?"

"No, you do it. As close as we are Megan and I have never fooled around, I'm sure both of us want it to remain that way," she explained.

"I think we better take it a little slower than that if you don't want it to hurt," Matt said reasonably.

"Fuck that, I have been using dildos up my ass since college, I like it when it hurts a little," she told him.

Matt shrugged then inserted the nozzle of the tube in her ass, before giving it a little squeeze. He put more on the head of his hard cock then handed the lube to Suzy. He knee walked into position then pressed his cock against her sphincter. It opened with very little pressure allowing his cock to ease into her ass. He was looking down at her as he sank into her tight ass. He thought about stopping to let her adjust but a small shake of her head dissuaded him. In one stroke he buried himself to the hilt. He paused then flexed his cock in her.

Letting out a moan she pushed her hips off the floor, "Fuck me now, fuck me hard."

Matt took her at her word long stroking her tight ass. Suzy had her head within inches of them avidly watching.

"How does it look Suze, do I look good with a real cock in my ass?" she asked her friend.

"This is so hot, I can't wait for him to sodomize my eager little butt," she groaned out while fingering her pussy.