When His Sister Cums... It's Messy

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First the sister, then her friends. Now what?
6k words
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93.7k
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Part 3 of the 3 part series

Updated 06/09/2023
Created 03/13/2019
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When Shannon caught her friend Claudia riding her boyfriend, she wasn't as upset about that- THAT was all part of "The Plan"- as she was about them discussing possible deeper feelings for each other. So she kicked into damage control mode.

"I'm pregnant, and here's the test to prove it," she announced.

In her hand was a box, a box that contained a new pregnancy test kit. So far the results were mixed- one was positive and the other was negative. How would this one break the tie?

Jason's head started spinning again, he dislodged semi-erect babymaker from Claudia and tried to make it to the kitchen sink- if only he could get a drink of water...

Too late. Shorts around his ankles, he caught the edge of the sink with his hands, held on for dear life, in a cold sweat, and started retching.

This couldn't be happening! What seemed like every guy's dream nearly 30 hours ago was now his living nightmare! 3 beautiful women at his taking, having sex with them all, and when he was with one, the other two were with each other, in a beautiful lake setting. What guy wouldn't love that idea? Now, he was the sperm donor pawn in some horrible sex chess game they were playing, while he wasn't even playing sex checkers anymore. He had one, maybe two or even all three of them pregnant now, and to top it all off, he had a huge gash above his eye and probably had a bad concussion.

At least the concussion clouded his thinking so he couldn't fully comprehend how he had been so thoroughly played, and what a disgusting whore he had become.

Kimberly responded first, "Quick! Get his clothes off! He needs a shower and then I need to get him to a doctor. If he's vomiting he has a severe concussion and he could die!"

Kimberly took her clothes off also and grabbed Jason while Shannon started the shower. Kimberly bear hugged him, letting the water run all over both of them, and the floor. She proceeded to clean him up. And of course, this got Jason excited.

"Easy, Big Fella, you have enough going on now," Kimberly sternly warned him. But then pulled him closer and whispered in his ear, but I did like it, and I'm not saying 'never again'", which made him smile.

After he was showered, Kimberly helped him get clean clothes on, and she dressed, and then ordered, "Shannon, you and Claudia do whatever you have to do to clean up, then head home. I will take Jason to the hospital and see how severe this is. Keep your phones on, and I will keep you posted. Shannon, can you drive Jason's car, or is that your car?

"His, and yes, I can drive it."

"Good. Claudia, go with Shannon and wait for me at Jason's place. What's the address in case he can't tell me?"

Shannon told him.

"Okay, good. Any questions?"

"Wouldn't it be easier if Intooknhim, since I live with him, and you take Claudia with you?"

"Shannon, shut the fuck up!" Jason exploded. "I think you 'plans' have caused enough damage, don't you?"

She had nothing to say. Really, this was largely her fault. Sure, Jason should have used condoms- lots of them- but he had TRUSTED Shannon, and look where that had gotten him.

"While we are gone, I need you two to talk and figure this mess out. This is not what we had planned," Kimberly said, then left with Jason.

Jason didn't say anything on the 15 minute ride to the nearest hospital. He got checked out- his eye would be okay, and he got orders for how to handle his concussion which was a good one, but one he would fully recover from. But he was ordered to give up boxing and also to give up head butting solid objects. But he felt a little better after whatever he was given at the hospital kicked in.

So Jason and Kimberly talked.

"How in the hell did I get here? My life is fucked, Kim!"

"No, it's not. How do you feel about them? About all three of us? You are here. Because someone you maybe loved, or had feelings for and trusted anyway, got us involved and we manipulated you for our selfish desires. Jason, I am sorry. I really am."

"What should I do if all of you are pregnant? I could marry just one, but ALL THREE?"

"Jason. It will be okay. One, I doubt I am pregnant. The timing is wrong. Two, Shannon had a negative test as well as a positive one, so, maybe she's not, either. And who knows about Claudia yet. Lots of things have to come together."

Yeah, like multiple loads of cum and her eggs. The details are foggy, but I think you each got several loads over the course of the last 2 days."

That may work in your favor, Jason. The average male needs 36 hours between ejaculations for his semen to fully recharge with a full compliment of spermatozoa. And you didn't wait 36 hours."

Jason just looked at her blankly, then finally said, "Who the hell are you? Pardon me, but I'm beyond the point of wanting to tolerate bullshit, somehow in the hell does lesbian know that?"

"I teach psychology. My specialty is sexual development. That's how I know both Shannon and Claudia. I am their academic advisor and also the faculty advisor for their dorm floor."

"So, Misses Sex Professor, do all wmwomeniving in the dorms have lesbian sex, or did you happen to find two hotties that were roommates or whatever that you groomed and manipulated?"

The question stung hard, mostly because it was true. Kimberly had probably manipulated these two women- and others over the years- just like Shannon had manipulated Jason. She wasn't just a cougar, she was a predator. And that shame she had repressed for all these years came to the surface. And she had nothing to say.

"I guess that's my answer. Sorry, Kim."

"No, you are right. You are upset with Shannon- and rightfully so, but she learned it from me. You, and to a lesser extent Claudia are the victims here."

"Tell me about Claudia. Why is she here, in the midwest at some podunk college, and not out east, or back in Europe, if her dad is so rich?"

"Her dad is rich, and you might even know the name. But her mom is not his wife. She is his mistress. His wife knows about Claudia and her mom. I actually knew her mom years ago. She was a model and professional volleyball player and we were friendly towards each other. You would probably know her name, too. Anyway, she became his mistress and became pregnant, which is a huge no-no for a European mistress. Anyway, Dad pays them off with a monthly stipend and pays her tuition, but she will never be his heir. She has hopes to make it on her own, and he will be proud, and someday they can have a meaningful relationship and maybe she will take over some of his business interests. But I don't think it will happen that way, and neither does Claudia's mother. So she sent her here, away, hoping for a fresh start."

"Tell me about Kimberly," Jason said.

She let out a sigh, wondering where to begin, and what to share. "I grew up with brothers on a farm and never had girls to play with. I loved sports, played tough thanks to my brothers, and school was easy. As I said yesterday, I had a boyfriend in college that I slept with, and later a fiance I slept with. Sex with those two men left me unfulfilled, but I really appreciated the women's locker room. I never felt 'gay' until a teammate groomed or manipulated me," then she paused, her voice caught in her throat, then continued, "much like I manipulated Shannon, Claudia and a few others."

She took a drink of water, then continued, "I was in college, left, went to the Olympics 14 years ago, won bronze, also won a world championship. Then wrecked my shoulder. So I went back to college, studied education and psychology, and stayed in academia."

Then she concluded, "I met Shannon and Claudia. Facebook kept me in basic contact with Claudia's mom who reached out to me and sent Claudia to school here. And I took advantage of her."

"Tell me about the Shannon you know," Jason said.

"Shannon LOVED psychology. Loved to study and direct behavior just to see if she could. And is good at it, obviously. She manipulated her freshman roommate, Claudia, for sex, which I saw as permission to go after both of them myself, since I had already been with Shannon. "

"Shannon would talk about 'The One' she wanted to marry- some boy she did something with once. She showed no interest in other men at college, 'saving herself for The One', but would have lesbian experiences occasionally. She is interesting- not typical lesbian or bisexual, more narcissistic than anything. But I couldn't help it and fell into her orbit. She can be an angel. Lovely. And I love her, but she can also be..."

"PULL OVER! PULL THE CAR OVER NOW!" Jason yelled. As soon as the car hit the shoulder he rolled out of the car and threw up. After several minutes he was ready to go again.

"That head injury must be real bad," Kimberly said, concerned.

"I feel a little motion sick, but your description of Shannon's manipulation just made me spin, and I lost it. I'm really sorry you had to see that, again. And I never said 'thank you' for helping me earlier. So thank you, Kimberly."

"Don't worry about it. I feel bad that it escalated so fast. I wanted to help Claudia and I am afraid I hurt her." But Kimberly added, "I am not upset about our part together, Jason. I did enjoy it. I hope it works out well. Hopefully we can salvage it."

"Do you know Amber, the other roommate that's fucking Shannon's brother?"

"She was only interested in men. As far as I know, she never experimented with the other girls, at least from what they said. Wants to be penetrated by men to show her worth, and can't do it with women. Penetration initiated by a female isn't the same. That's the short version. May be more there, and it's really not a big deal. Also probably thinks it's recreational." Then Kimberly turned to Jason, "Have you slept with her?"

"No."

"I'm surprised."

"Why, because I have the morals of an alley cat," he said a little defensively.

"No, but the more men she racks up, the more her worth. So beware."

They rode on for a while, talking about how to make this potentially bad situation a little better. Then they got to Jason's house. Kimberly got out and went around to help Jason out of the car and up the steps of the small house. When Jason walked, Scott said, "Hey, Dude. Whoa, what happened to your eye?" Then he saw Kimberly and not Shannon. "Where's Shannon?"

Jason walked unsteadily over and tried to take a swing at Scott. It was off balance and weakly hit his shoulder.

"What the fuck, Dude! What's that for?"

"Fuck you, Scott! This is your fault. 'Be my fucking wingman, fuck my sister so I can fuck her roommate.' Fuck you, asshole!"

Amber came out of the other room yelling, "What the hell, Jason?" Then saw Kimberly. "Miss Burns?" Not seeing Shannon, asked, "Where's Shannon? What's going on?"

"It's a long story..."

*****************

Things were a little strained between the four "roommates" for a few days. Jason knew it wasn't Scott's fault he was in his predicament- not entirely, anyway, but he was not ready to apologize yet. With a week and a half left of his summer class but still feeling the effects of his concussion, he had about all he could do to sit through two hours of class every day, so he took time off from his job. In 10 days he would be done with college, but wouldn't graduate until August and already had a career lined up for September.

He started to notice Amber. He noticed she didn't have any intention of going back to her home, he noticed she and Shannon were a little strained, an finally, he noticed she was all woman.

The Morals of An Alley Cat.

It was Thursday afternoon, the week before class was over, 6 more days left of school. He just needed to get through those six days. Middle of the day, Shanon and Scott both at their respective jobs, and he was alone with Amber.

"So, are you and Shannon headed back home anytime soon?"

"In August. Scott said I could stay, and Shannon is here now, so...Scott said it was fine."

"Hmmph."

"So, if you don't mind me asking-"

"I do mind-"

"What is up with you and Shannon? And the others?"

Now was the time to play it careful. He didn't want to reveal too much. "I'm upset she manipulated me. I've liked her since 10th grade, when I noticed her as a woman, but I am upset. I will probably get over it, but we need to really talk, and until I get back to normal, I don't feel like I can." Then he turned the tables and focused the discussion on her, "So why haven't you lezzed out with the others?"

"Never been interested. I like dick too much. I like the feel," she said as casually as if she were discussing the laundry or dishes.

"Aren't they all the same? Dicks, I mean. Don't you ever wonder what licking a pussy is like? Don't you want to taste one?"

"Do you wanna suck cock?"

"Fair enough. I like pussy and some other guy doesn't interest me."

"Don't get me wrong, Jason, I have tasted myself on other guys. I love the taste of commingled cum, but I don't want to go down on a woman." Then she stuck her hand inside her waistband and pulled her finger out and sucked it, staring right at Jason, "Besides, I have it right here."

No shame. What had Kimberly said? Amber gets her worth by collecting men? Okay. He was still pissed at The Twins, so this seemed like a good idea...

For an Alley Cat.

Jason stood up, stretching in an over exaggerated manner, emphasizing his crotch. Amber took the bait, looking right at it, then he sat back down.

"So, how mad are you at Shannon, Jason?"

"Pretty mad. I had faith in her and she used me."

"You know WHY I ended up with Scott?"

"Coz you liked him?"

"No, coz Shannon didn't want to fuck her twin, so I got Scott by default. If Claudia had come down with us, who would you have chosen, Jason?"

Then, probably Shannon. Now, definitely Claudia between the three. But he didn't tell her that. Right now, she's the only one here, and if she will fuck Jason now, he's doing Scott a favor finding out now then after he marries her.

"I guess I would have wanted the one that seemed to want me. Who would you have chosen if you had your chance, Amber?"

"Oh, definitely you, Jason," as she crawled up next to him on the couch. "Let me see what turned Kim Burns straight and has Claudia and Shannon fighting."

She reached over, he relaxed his posture so she could access his waistband, and she pulled out his semi-erect cock.

"Hmm, it's not THAT big." She continued to stroke it and it grew. "I'm not sure what all the fuss is."

"Maybe you need to take a closer look at it, then."

She got closer, and lightly licked the head. It twitched and jumped in her hand. Then she licked it harder. Then put as much of it in her mouth as she could and sucked hard.

"Oh, I can see why this is worth fighting over."

She repositioned herself, opening up her crotch so he could reach under her and touch her. The position was still uncomfortable, so she said, "Let's lay on the floor."

They both stood up, took off their clothes, and Jason laid down so Amber could straddle him in a 69. They both knew thay had at least 4 hours till the other two got home.

Amber had a light, but not pale complexion. She was a reddish blonde. Jason never knew what to call the color, but her landing strip public hair matched her head. She had a few light freckles on her nice sized tits and her button nose.

But he was looking right up her love hole, licking her pink inner lips and trying to tease her clit at the same time. Amber was staring at Jason's strong thighs while taking in as much of him as she could without gagging. She wanted to taste his cum, but thought maybe she would settle for the secondary, commingled cum if he would paint her insides.

"I've gotta have this. Jason, fuck me."

"Let me get a rubber."

"I want to feel you fill me up though."

"After all the trouble I'm in? Condom, or nothing."

"Fine. But hurry!" She diddled herself while he went into his room, found his box of condoms, and came back. She sat up and he stood, in Greek godlike form, hard dick in her face, and she rolled the rubber down his shaft, trapping air in the reservoir end. Then she laid back down, opened her legs wide, knees up, and invited him inside her. He got down on top of her, and she wrapped her legs around his hips, making sure to trap him there.

He pushed-not rough, but not gentle either, as her eyes rolled back in her head. She let out a sound like, "Nngghhhaahh," as he filled her void like no man or no toy before had. She thought he would split her in half, which was saying something because her path was well traveled. When he buried his whole shaft inside her and she felt his balls against her ass, she finally remembered to breathe.

"Oh. My. God. It feels...so...SO..."

Then he slid back, and thrust it in fast and hard.

"Oh God, Jason! Give it to me! I NEEEEEED IT SO BAD!"

Jason pumped her like she never could have imagined. Unbeknownst to her, Amber was Jason's seventh lover- far fewer than the number Amber had, but Jason's education, stamina, and experience really ramped up in the last month or so, which made him her best.

And Amber had never experienced something so pleasurable in her life. She hoped it wouldn't be the last time he did this to her. She now knew why the others were addicted to him.

Luckily Jason was able to vaguely remember something Kimberly said about semen needing 36 hours to be fully sperm potent. It had been more than 36 hours since he had discharged last and when he felt a snap on his dick, he rightly suspected the condom broke. He didn't need a fourth baby mama, so he quickly pulled out and...

"What are you doing?"

"The condom broke."

"Quick, cum on my chest!"

He stroked a couple times and covered her tits. She tasted his seed that way. At that moment, though, she gladly would have taken him full blast in her womb and made him a baby, too.

Yes, she definitely was going to need more.

They rested there for about 10 minutes, and she started to play with him, getting him hard again. "We have about 3 hours, please can I have it one more time before they get home? Then we will figure out where to go from there."

"We can never be together, you know that, right Amber?"

"Not anytime soon, anyway. But never say 'never'".

This time she sat on his lap, facing him. She wiped his cum off, but her tits were still sticky. But they were nice, and he sucked her huge, pink nipples while she slowly rode him. She came twice, and he filled a condom but not her with a comparably small load. Her womb didn't get his cum, much to her immediate disappointment, but to his relief.

Later that night, the four tried to get along. The Twins seemed to have no idea that their partners had slept together. Amber got out of having sex with Scott. She was too stretched out so she faked an upset stomach from supper. As she lay in bed next to Scott she had to listen to Jason fuck Shannon and wish it was her, because she seemed to be really enjoying it.

Jason and Shannon still slept in his bed together and they had sex two of the five nights his last week of school. He wanted to keep everyone from becoming suspicious. After class on Friday he packed a few clothes and said he was going home- alone. Shannon wanted to go along, so she could go to her house, she said, but he refused. But instead of going home, he met up with Claudia.

It had really killed him to only text or briefly facetime her. She was living with Kimberly so they checked into a hotel so they could be alone. She was the shy, submissive young woman he met just a few short weeks ago.

When they hit the room, locked the door, she was all over him. "Come here and fuck me, my lover!"

She had the same flowered sundress on when he first met her, but this time she had string bikini panties on that were in the way and he ripped them off, and threw her on the bed.

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