When His Sister Cums Ch. 01

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Friend wants his roommate to entertain his sister.
3.8k words
4.32
51.8k
71

Part 1 of the 3 part series

Updated 06/09/2023
Created 03/13/2019
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"Hey, Shannon and her roommate are coming down this weekend, and I need a wingman. I want to fuck Amber, and I can't do that with my sister around. You need to keep her busy," Scott told his roommate Jason. The last weekend in April on campus was epic, known across the country for its party weekend.

"Maybe I want Amber, and you can have Shannon. You guys are twins, so you can go fuck yourself," Jason replied.

"C'mon, dude, you can fuck her if that helps. I won't stop you this time. She's always liked you anyway and maybe she'll give it up THIS time. "

"Why wouldn't she let me fuck her on graduation night, then? All I got was sticky fingers and blue balls."

Scott hated it when Jason brought up how he caught Jason fingering his twin sister Shannon on their graduation night nearly 4 years before. The fact is, Shannon did like Jason. The dirty little secret was that Jason really liked Shannon, too.

"Okay, stop. I should have let you try to fuck her. Then she would have slammed her legs together and then you would have moved on," Scott said. Maybe he knew a little more than Jason thought he did. Maybe it wasn't such a secret.

"If I fuck her in the ass, can I have a crack at yours, too, to compare? You are twins, y'know."

"Shut up you sick fucker. Just keep her busy. If you magically score, just keep it down. If I sleep with Amber, I will owe you", he said.

Roommates in college and best friends since Kindergarten, they always talked to each other this way. If the roles were reversed, Scott would do whatever to help Jason score. And if Jason did nail his sister...who knows? He could do a lot worse for a brother-in-law.

When Friday rolled around, Scott noticed Jason's room was picked up and neat. He had also shaved and looked presentable. He seemed to be real excited, but tried not to look desperate.

When the women showed up, they talked about plans, where they would go out and drink, and had an air mattress and blankets out. Both guys hoped it would not be necessary to set up the air mattress though.

"Alpha Delta Lambda is having a big kegger, but Fuzzy's is having a band. $10 cover, but the band is good," Jason said.

"Whatever," Shannon said. "Where's the best place to find guys?"

"Right here", Scott replied. Amber giggled, and Shannon rolled her eyes.

"Let's go to the kegger, and then we can see the band later. A few other parties have bands, too, just none as good as Strung Up. Their guitarists are excellent," Jason offered.

"Shall we?" Scott said as Amber took his offered arm. Jason then looked at Shannon and offered his hand, but she quickly looked away, pretending not to see it.

Jason thought to himself, "Great. Cockblocked. That fucker owes me."

They made it into the kegger. It was crowded, hot, and even though the beer was free, it was Milwaukee's Best. There were supposed to be laws against false advertising, yet The Beast had never had to change its name.

Scott and Amber disappeared, leaving Jason and Shannon alone, surrounded by 200 people. Jason got them each a beer, and they stayed off to the side, just observing drunk dancers while choking down crappy beer. It didn't take long before fish started biting.

"Hey, baby. I see the stars in your eyes and me in your pants..." some drunk guy said.

"Wow, really? I see you in my pants, too," Shannon replied.

"Really?!" Drunk Guy seemed surprised that worked.

"Yeah, every time I shit them! Beat it, Asshole!" She said, crushing his dreams.

He turned to Jason, "Maybe you should tell that bitch to be polite."

Jason replied in a low tone, leaning into the drunk's personal space, "Maybe you should be a little more polite yourself. Next time, she may kick you in the balls. Yes, her aim is THAT good."

About two more bad pickup lines and they decided to check out the band.

"Do we need to tell Scott and Amber?" Shannon asked. She was torn between the safety of her brother as a chaperone, and the freedom of him not being there. And remembering the excitement of graduation 4 years before.

"Honestly, he wants me to keep you away from the two of them. If he has his way..."

"You will be the wingman, allowing him to defile my roommate. And what do you get out of the deal?" she asked.

"He said something about fucking him in the ass," Jason joked.

"You guys are so sick. And juvenile." But she laughed. "Maybe we can find something better. So, where is that band playing?"

They played it wrong. The bar was packed and sold out. They should have gone to the bar first. Or maybe, this would work out to their benefit...

They walked around for a little bit, but not stopping at any other parties. They held hands, and late April evenings in the Midwest could be cold, warm, or somewhere in between. It had been 75 degrees at 4pm, now was passing 60 on the downward slide. Jason pulled Shannon closer to him to keep her warm. They talked about nothing, and everything.

"We have beer and other stuff at the apartment. Wanna go back?" Jason asked.

"Sure. If that's what you want. I mean, I hate to have you miss the big party weekend though. It's not fair that you miss the party so my brother can get lucky."

"Who says he's the lucky one," Jason replied. He stopped, turned to face Shannon, and took a deep breath...

And went for it. Neither one was drunk, so they couldn't blame that later. Jason pulled Shannon in, planting a kiss on her. Then he pulled back.

And she pulled him back in. And gave him tongue.

"Take me back. Lock them out so he can't stop us this time. Finish what you started 4 years ago," she told him.

"I have wanted you since then," he told her in reply.

"Then have me. I'm all yours"

They raced back to the apartment and locked the deadbolt. As soon as they had that locked, they started ripping each other's clothes off. He found firm, C-cup breasts and a neatly trimmed pussy. She found a thick cock that was at least 8 inches long.

"Holy shit! How are you going to get that in me?!" She gasped in excitement, a little fear, and plenty of desire.

"Lay down and I will get you ready," he told her. He gently put one, then two fingers inside her.

"Mmmm, makes me think about graduation night," she said.

"But I didn't get to do this," he said, and dove in her wet pussy with his tongue.

"OOH GOD!" She screamed, as her entire body went rigid. He lapped at her puffy lips as she soaked his face. "Aaaghhhh! Oh god, oh god, don't stop!"

She came, her body convulsed, and her knee smacked Jason. "Okay, okay, stop! Too sensitive!" She got the words out between panting breaths.

He came up for air, hard as a rock, and she said, "My turn to please you. Lay on your back."

Jason lay down on his back and placed his hands behind his head in anticipation of what was to come. Shannon got up on all fours, head facing his feet so her pussy was pointed toward his head, off to the left side. She ran her fingers through his pubic hair, stroked his cock, then balls, then gripped his cock again, flipped her long brown hair off to the side, and went down on his cock with her mouth, then started bobbing her head, slurping on his thick manhood. She almost came from the excitement.

After a couple minutes of enjoying the sensation, Jason reached out and cupped Shannon's ass and stuck his thumb in her pussy and started thrusting. It made a squishing sound and her cum from his eating her out moments ago and now his penetrating her tunnel was running down his hand.

He switched and rubbed her pussy with his index finger, making it wet, and then switched back. With his thumb back in her pussy, he poked his wet index finger in her brown star, making her moan. "Oh, I want to swallow your cum, but I need to be fucked by this huge dick! Will you do that, Jason?"

"You would rather have my cock than my thumb?" Jason teased.

"God yes! But be gentle, I've never had anything this big in me before," she said, still panting while enjoying his hand penetrating her two most sensitive and private spots.

"How do you want me?" He asked.

"Sit in the chair and I will sit down on you so I can control how fast and deep," she said. "Then we will go from there."

"Want me to put a rubber on?" Jason asked.

"Oh hell no, I want skin on skin and to be full of your cum when we finish," she said, almost a beg.

Jason sat in the chair and held his long dick up for Shannon's pleasure. She was facing away from him, hands on his knees, took his meat and placed the head of it at her lips, and tried to sit down.

It was too big.

She turned around and put her mouth on it, leaving plenty of saliva behind, and repeated the process, going slow. Inch by inch her tunnel opened, taking more and more.

If only Jason could have seen her lovely face. Her eyes got huge, her mouth was wide open until she said, "Oh boy! Oh my, it feels so huge!"

Before long she had taken his entire length and started the return trip, sliding up his length almost as slow as she slid down. As she approached the top of his cock, he could feel her wetness left behind on him, and it was hot and cool at the same time. Then she sank down again, faster this time, the slid up. Each movement went faster and became easier for Shannon.

During this process, the blood seemed to leave Jason's face, racing towards his member currently buried in his best friend's sister and his own secret crush. Each stroke felt better and better and left her cream behind on his piston. He grabbed her hips and she leaned back against his chest, spreading her legs wider, taking her weight off her legs just in time.

"Oh Jason, I'm gonna cum! Oh god Jason!"

Then the door handle wiggled and someone banged on the door, "Hey, we're coming in," Scott said from the hallway on the other side of the door.

"NOOOOOO!" Shannon cried out, mostly for herself but for Jason's benefit too. "Keep...keep pumping...aaaahhhh. ooohhh god!" Her body shook and convulsed violently.

Jason scooped her up and hurried off to his bedroom just as they heard keys in the door. Shannon was still riding the wave of an exciting but partially interrupted orgasm. In their haste, they left their pants and underwear on the living room floor next to the chair.

"Oh, Jason, I don't know how we moved so fast. Thanks. I don't care if Scott knows we're fucking, but I don't want him to see us."

Jason, meanwhile, hadn't cum yet, and his aching balls and cock needed release. Shannon noticed he was coated with her cum, but she didn't have his inside her yet. "Oh, you didn't cum yet." She laid down, spread her legs, and welcomed him to her with open arms. "Come here, Lover," she beckoned.

He climbed on top but didn't immediately enter her. He kissed her face, and she ground her hips against his and his cock easily entered her stretched out tunnel. "Oh, that's SO good," he said.

"Ugh, god, that fills me up so good! Now, cum in me. Please give me your load!"

"Faster, Jason, fuck me faster! Hard, hard, ugh god, pound my pussy Jason!" Shannon cried out.

All of a sudden in one quick, fluid motion, he pulled out, was up on his knees, flipped her over with her ass in the air and face buried in a pillow. He found her wet and gaping entrance, and at about 75 percent force and length he slid home.

"OOOOHHHH! GOD that feels..."

Then he quickly picked up his pace and went full depth. As he pounded her, he would bottom out and momentarily stop his balls would jump up and hit her clit.

"Feels...SO...good. Oh god, I'm gonna..." and her words trailed off into a moan and then an animalistic scream. And when Jason felt Shannon's pussy involuntarily contract and spasm around him he cut loose with spurt after spurt of the biggest load of cum in his life.

Shannon laid there, panting hard with her head in the pillow at a weird angle, and Jason swayed back and forth on is knees. He held on to her hips for stability, actually a little unsure of where he was. He knew he was inside Shannon, but it took him about 45 seconds to realize it was his bed in his room.

Then he collapsed. Shannon collapsed next to him and draped her right leg over his waist and leg. They looked at each other, and at the same time it dawned on them what had happened. Jason was unaware of the consequences, but Shannon knew.

It was too early to be pregnant- no test was that quick. But she knew at that moment that millions of his sperm were racing through her cervix, looking for an egg. If one was there, as much as he pumped into her, the odds were she was knocked up. She hadn't taken her BC pill in months. But even if she wasn't pregnant, she was determined to marry this man.

They both looked at each other, and as a smile spread across their faces at the same time, they both said, "Wow."

Then they both yelled, "JINX!" And then laughed.

Eventually, Shannon said, "Jason, I should tell you, I've never had a man inside me before. Sure, I've used toys- hell, I brought a couple along this weekend. And yes, I've fooled around a little with girls. All told, I've had about a dozen fingers and tongues in my pussy. I hope you are okay with that. But I have never had a real dick inside my pussy. Mouth, yes, twice. But never inside me like that. And I never want to have another in inside me. Since about 10th grade I have never really thought about being with anyone else other than you."

Jason pondered that monologue for a moment, and then he spoke from the heart. "I've been with 2 or 3 women, but I have always had a soft spot for you. You don't have to pledge undying loyalty to me yet. We are not at the same university and in a few months we will both graduate and look for jobs. I know it's naive to say we will always be together and will do whatever to make it work, but I'd like to try."

As she listened to him, she could feel at least 2 things. One, she was getting excited, and two, so was he.

She rolled over onto her back, opened her legs, and said, "Make me yours again, Lover. See if you can break the bed. But you will never break me."

This time was more about love and less about lust. They held onto each other. They felt each other out. They came together. And Shannon's canal was flooded once again. The poor bedsheets would never be the same.

After that time, Shannon slept while Jason stroked her hair. He wasn't sure what he was feeling. Eventually he surrendered to sleep also.

About 3 in the morning Shannon and Jason were woken up by Amber screaming, "Oh god, Scott, give it to me! Fuck me hard! Cum in my ass!"

The light was still on next to the bed and Jason looked at Shannon who flatly said, "Oh hell no. That thing will never fit in my ass. Don't even think about it."

They laughed together and she said, "But it fits in my mouth and pussy just fine. "

"I gotta go to the restroom first," Jason said. He looked for some clothes, then said, "Oh, shit! I think your panties are still out in the living room."

"I think Scott and everyone else knows what we did already. But my bag is out there. Will you grab it for me, please?" Then she got up, and raced out the bedroom door and said, "Race ya to the bathroom!"

She won the race, so he picked up he panties and overnight bag, brought them back to his room and took his turn in the bathroom. From Scott's bedroom he could hear panting, giggling, and Amber describing the feel of Scott's cum in her hair.

"At least I came in Shannon's pussy- twice," he mumbled to himself.

"Hand me my bag, please Lover," Shannon said when Jason brought it in and shut the door. "Give me about 15 minutes and then join me in the shower, and then we will start round 3. And 4," she promised.

Jason still has to pee and after about 10 minutes he had had enough and went pee and then joined her in the shower. They quickly got clean and snuck back down the hall to Jason's bedroom.

"Lay down, Jason, I want to swallow your load now."

He laid down and she stuck her freshly trimmed pussy right over his face. He liked the view but hoped the shower had taken care of both his loads he left there. Then he noticed her pussy smelled like berries. Along with shaving she douched while alone in the shower.

She rubbed his cock and balls, and then started sucking. Meanwhile, he spread her checks, opening up her pussy, and started licking. Neither one had great technique, but neither complained either. It only took a few minutes until they both came. Jason's face got soaked and Shannon nearly gagged on the force and amount, but she handled it all.

"Two huge loads earlier and that one nearly drowned me it was so big. But I loved it!" She said.

"You taste wonderful, too. Who knows how my life would have turned out had I got that taste 4 years ago," he said. "I feel like a crack addict."

"Mmm, you can be addicted to my crack," she said.

One more round of penetrative fucking, one more load of cum in her womb, and some noise in the kitchen, they decided they needed breakfast, too. They threw t-shirts and shorts on, but neither bothered with underwear. They headed down the hall and realized no one could make eye contact with each other.

Jason couldn't look at Scott for what he had done to his lovely sister, and even though Scott told Jason he could fuck her, he still couldn't look at him. Not out of anger, but embarrassment maybe? Scott and Shannon couldn't make eye contact because they both slept with their twin's roommate. Amber briefly looked at Jason, who gave her a big, open mouthed, exaggerated wink, which embarrassed her. Finally the silence was too much and Jason said, "Okay, we all had sex. Big deal. Scott, I've liked Shannon for several years and we had sex. Maybe we will get married. Who knows. And you slept with Amber. Good for you two. Enough pretending nothing happened, and enough being awkward."

Amber, not wanting to appear to give in to her promiscuity said, "How do you know we actually did anything."

"Umm, because I heard you." He pretended to wipe something out of his hair, and continued, "I don't care. No one cares. Embrace it, and let's move forward. Today is Saturday, and I intend to make love to Shannon about 10 more times before she leaves tomorrow-"

"Maybe more," Shannon interrupted.

"And hopefully every weekend after that, and all summer long," Jason continued. "I'm not going to pretend that nothing happened. Now, Shannon and I are going to have breakfast, then more sex. Then look for lunch, a band, and more sex. Maybe sex in public. Who knows. Shannon, dear, anything to add?"

"I want bacon and toast, then more sausage," she said.

They only made it 8 more times that weekend. Scott and Amber had a lot of fun also. By Sunday night the four of them made an arrangement as to who would go where next weekend. Amber was going to come back down, and Jason would head up to Shannon's college.

On Friday night, Jason was escorted into Shannon's dorm hall and met a few of her friends. They all eyed him like a piece of meat and all groaned when Shannon announced she booked a hotel room for just the two of them.

The dorm wasn't going to be very conducive on Friday for rampant sex, so they got a cheap hotel room that also bragged of a pool and sauna and hot tub. The pool was small and cold, the hot tub was broken, but the sauna worked.

"I brought a box of condoms along, just in case," Jason said.

"We don't need them," she said. It wouldn't have mattered anyway. They wouldn't know for sure for several weeks, but nature had already taken its course.

They had sex in the sauna and almost got caught. They retreated to their room after that. Shannon brought some toys along to play with. She still wouldn't let his dick in her ass, but they tried all sorts of other things.

The next week Shannon came down and Scott went up. Then it was finals week, and Shannon headed home for a few days. Jason and Scott both stayed in their place. Jason was working the summer and taking a summer class so he could graduate in August. Little did Jason know Shannon was too, at his university, and needed a place to stay. Her parents thought she was safe staying with her big brother. Things were looking up for Shannon and Jason. Well, grades weren't up, but that wasn't a big consideration right then.

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