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Waifu Royale 2.0 winner #2 :: Triangles ::
🕑 Added 2025-10-23 14:49:53 +0000 UTCYou can read the story and see the illustration here for free.
Here's the winning prompt:
The apartment belongs to two friends, a man and a woman. They both have a crush on Sydney, so they're happy to take her in. They end up cuddling on the couch which turns into makeout heavy lovemaking.
I hope you enjoy this one! I had a lot of fun with their dynamic.
When they found Sydney sitting on their doorstep they knew that the night was about to get complicated.
"Heeeey... So my roommate brought a guy over and they're being waaaay too loud..." Sydney said, looking really tired.. " Can I crash here tonight?"
Tim and Pam looked at each other for no more than a second, but in that moment an understanding has been reached. They've both had a huge crush on the woman before them, and neither would ever turn her down.
But... Why did she come here? That had to mean something, right? Sydney had plenty of friends. Did she also like one of them?
If so, which one?
"Yes! Shit! Of course Sydney!" Pam said, as she hurried to open the apartment doors.
Not to be outdone, Tim knelt by the tired looking woman and asked. "Are you ok?"
"Yeah... I am now." Sydney said with a small smile.
Pam looked back into Tim's eyes. She saw her own feelings reflected in his. Whatever happened tonight, if one of them managed to get closer to Sydney...
Let there be no hard feelings.
---
Before too long the three found themselves settled on the pull out couch, swaddled in blankets. Some netflix show was playing quietly on the tv, but nobody paid it too much attention.
Sydney settled between the two, feeling equal parts comfortable and excited. To her right, Tim was trying very hard not to touch her too much. To her left Pam was pretending that she was not staring at Sydney's legs poking out from under the blankets.
"My, you two are warm!" Sydney sighed as she wiggled her butt towards Tim and threw one of her legs over Pam's lap. The two came from some small town in the south, and not for the first time Sydney wondered what they put in the water there. They were both so... Well shaped.
Both were thick and solid. Tim with his muscular build and Pam with shapely thighs and large breasts. Being squeezed between these two was exactly what she needed right now... Well, actually, she could think of a few ways this evening could improve- She shook her head. Listening to her roommate get fucked for like an hour really got her in the mood. Maybe it was a mistake coming here.
Being so close to these two was liable to say too much and ruin the night. "So! I always wondered... The two of you... Never... Did it?" Yeah, like this. That's exactly what she should not have asked.
"Never what?" Tim asked. Pam was still too distracted with the legs.
"You know..." Sydney murmured. "You two live together... Man and a woman... Never once?"
"Eh? No!" Pam laughed. "Noooo... I am not sleeping with that loser."
"Like you had a chance with me? Couch toenail clipper!"
"One time! ONE TIME!" Pam moaned.
They bickered for a while longer, making Sydney laugh. She relaxed into their banter. She managed not to reveal how horny she was feeling. Good! Now just... Relax and don't do anything.
"Wow... I wish I was this close with somebody..." She said and let her head fall to the side. Right into the crook of Pam's neck. Whoops.
Pam stiffened. She wanted to hold Sydney so badly, it almost hurt, but with Tim here- oh to hell with it! She put her arm over the other woman's shoulder and tried to ignore the way Tim looked away when Sydney nuzzled into her happily.
Sorry buddy!
"Wow, you're soft..." Sydney sighed, her chest filling with warmth. She reached out and twisted one of Pam's blonde curls around her finger. So soft.
"Ahem... You know what! It's getting late... I'll just..." Tim said, as he made motions to throw off his blanket. The way the two women cuddled right next to him- he did not need to see any more. Good for you Pam. Fuck!
"Yeah! I'll help Sydney set the bed-" Pam began, but Sydney cut her off. She reached out and grabbed the hem of Tim's shirt and pulled him back down.
"Don't go," She said, quietly in a way that made his heart beat ten times faster.
He laid back down, feeling rather confused. Sydney wiggled herself to her knees and leaned over him, her face awfully close now.
"Where do you think you're going?"
"Eeeeh..." Tim did not quite know what to say. Did he read it wrong?
He turned his body to look at Pam at the same exact moment when Sydney decided to pounce on him- intent on spreading the cuddles around evenly to maintain the peace. Instead of sinking into his neck, Sydney's face collided with his at just the right angle.
Her lips felt incredibly soft on his as he laid there stiffly, not quite sure if he should move or not. He wanted to grab her and show her exactly how much he liked her, but...
Sydney gasped. Not what she intended, but... Her hand landed on Tim's wide chest, enjoying the feel of his muscles. Gosh he felt strong...
"Whoops!" She laughed and licked her lips. "Bad aim!"
Tim laughed, but she saw something in his eyes. He wanted her. She knew it, of course, she was not blind. But... Sydney turned to Pam, who was not laughing. She laid there stiffly, trying very hard not to look hurt.
God damned love triangles. They never end well. She really should not have come here tonight.
Sydney leaned in and kissed her on the lips, before she could think herself out of it. The kiss was chaste, but there was something underneath. Sydney almost moaned when she saw the naked want in Pam's eyes.
Jeez, what was she supposed to do with these two?
"There... Now it's all fair!" She whispered, and settled back down between them and pretended to watch whatever the hell was on tv. Something about puppets trying to solve a murder case? Wait, that's actually cool.
Pam waited for the butterflies in her stomach to settle a bit, before she looked over to Tim. He was already looking at her, over Sydney's head. In his eyes she saw a mirror of her own thoughts. Something was happening here... And whatever this was, she was not going to ruin it by being jealous.
She nodded at Tim. He nodded back at her. Fuck, she loved that dork. If only he was a woman... Pam liked guys well enough, but had no interest in them romantically. And sleeping with Tim would just ruin what they had.
She relaxed and cuddled up against the side of Sydney's body. She let her hand rest on the woman's hip, then travel up to her stomach. She was rewarded with a cheeky smile, and Sydney's butt pressing back against her.
All three of them, at that moment, felt it. The shift in the air. The possibility.
Tim seized the moment first. He placed his hand under Sydney's chin, and turned her face towards him. Sydney's mouth parted slightly, but she said nothing.
"I think... You kissed her a bit longer than me... Unfair," he whispered.
Sydney licked her lips. "Oh... Sorry."
Their second kiss did not stay chaste for long. One of them, neither could tell who, pushed their tongue in, and then, they were off to the races. Sydney was happy to confirm something she always suspected- Tim was indeed a good kisser.
"Woah... My... Damn..." She said after breaking the kiss. "I think... I think we went a bit long there!"
Then, she turned to Pam- who looked like she was about to vibrate out of her skin with lust, and met her in a passionate kiss. She was so much softer than Tim, but no stubble! Damn, she could not decide which one was a better kisser.
Pam melted into Sydney. She wanted this woman from the first time she saw her band practice and her feelings have only grown since. Finally she could enjoy the taste of her- sweet and soft. She let her hands roam Sydney's body- slightly annoyed when she met Tim's hands grabbing Sydney's ass. She swatted him away and grabbed the butt herself.
Sydney felt dizzy from all the attention. She broke the kiss, desperate for breath. She fell back onto the pillows, a stupid grin on her face. "There! All- all even!"
She looked up to be met by two pairs of lust filled eyes. She could not quite believe her luck. This was certainly one solution to the love triangle problem!
"Hey..." She said, feeling inspired. The triangle was not quite filled out enough to her taste. "Could you two... Kiss for me?"
"Eeeeh-" Tim began. Yeah, Pam was hot as hell, but she wasn't really into him.
"Whatever loser! Come here!" Pam cut him off. She was of the school of thought that if a pretty lady asks you to do something in bed, you do it. She grabbed Tim by the hair and went for it.
The kiss was the oddest one, either one of them had ever experienced. It was awkward, at first, as both of them tried to work through their hesitation. Once they pushed through, they each found a willing, eager partner on the other end. Somewhere along the way, passion found them. Their tongues wrestled for dominance, neither willing to submit. Neither wanting to stop.
Sydney watched the kiss with the growing realization that this was possibly the horniest she ever felt in her life. Her pussy was already sopping wet and they hardly even did anything! Was Pam also this wet? Tim's blanket slipped off and she could very clearly see his rock hard cock bulging in his grey sweatpants. It looked impressive. God, she wanted to touch it so badly...
Then, she remembered that there was nothing stopping her anymore, so she reached out and grabbed Tim's bulge. It felt even larger in her hand... She felt her mouth watering. She should thank her roommate tomorrow!
"Hey there!" Tim said, after breaking the kiss. For a second he thought it was Pam grabbing his junk and the thought short circuited his brain. But it was just Sydney... Just Sydney rubbing her hand along his cock with a dreamy expression on her face.
"Wow... You're really hard..." She whispered. "Is this ok?"
He nodded stupidly and thrust out his hips to meet her hand. Sydney gasped and grabbed his shaft and stroked it through his sweatpants. It felt so good he could almost come- he stopped himself when he saw Pam's smirk over Sydney's shoulder.
If he came in his pants from this, he would hear about it for the next twenty years. "Hey Sydney... I think that Pam is feeling a bit left out."
Sydney let go of his aching cock and turned around to face Pam. "Aaaw..." She cooed. "Sorry... Do you want me to use my hands?"
Pam nodded with equal amount of dumbness as Tim had, which was all the permission that Sydney needed. She scrambled between Pam's spread legs and reached her hand into her shorts. God, she was so wet- Sydney's fingers slid so easily between her wet folds and inside her opening.
Pam moaned and threw her head back, her right hand grabbing for Sydney's neck, her left twisting into Tim's t-shirt. Sydney grinned and got to work. Her fingers slid in and out of Pam easily, dragging out moans and gasps each time.
"Tim... Could you- could you kiss her again?" Sydney whispered. "Pam? Is that ok?"
Pam moaned something that sounded like an affirmation, which was enough for Tim. None of the earlier hesitation remained- Pam's mouth was open and eager. It emboldened Tim to grab one of her large full breasts- something he'd always wanted to do. He was rewarded with a bite on his lip and a groan from Pam, but she pushed her chest out, eager to meet his hand.
Pam herself was rather surprised with how good Tim's hand felt on her breast- pinching and twisting her hard nipples- but at this precise moment she was too god damned horny to care. Sydney's fingers were working magic inside of her, and Tim's stupid mouth felt amazing on hers. Nothing could ever feel as good as all that.
Then, she felt Sydney's breath on her clit.
Somewhere along the way the woman must have taken off her shorts without Pam realising. Sneaky. Sydney was lying on her stomach, nestled between Pam's legs, her face so close to her pussy. Pam moaned hard into Tim's mouth as Sydney's wet tongue made contact with her clit.
The woman skipped all the pleasantries and moved straight onto sucking on Pam's clit- all the while her fingers continued pumping in and out of her, bending at just the right angle to drag along all her sensitive spots. It was all too much.
She screamed into Tim's mouth as she came. The dork actually tried to back up, so she grabbed the back of his head and kept him there. Their kiss turned sloppy and desperate, but she did not care. She was in heaven!
When her orgasm was over she pushed Tim away and grabbed Sydney by the shoulders and dragged her up, onto herself. The woman laughed happily and let herself be kissed. Pam found that Sydney's lips tasted even better when they were coated with her own juices. Who knew!
They melted into the kiss for a long time, or perhaps a couple of seconds. Neither really cared about that right now. Sydney broke the kiss when she smelled something- something- something really nice right next to her face.
Tim's cock.
"Rude..." Pam breathed out, looking at the appendage with a mixture of annoyance and interest. "This is borderline sub-human behaviour, Timmy boy."
"Oh stop it," Sydney laughed. "He's in need..."
"Yep. Big need right here," Tim said, stroking himself slowly. "Big big need."
Sydney laughed again, and without further comment leaned over and put her lips around the head of the cock. Tim moaned, seeing her like this, her big beautiful eyes looking up at him, makeup smeared all over, as she began bobbing her head up and down over his tip.
Beside her Pam huffed and shimmied herself up a bit, to get a better look. Meanwhile, Sydney swallowed more and more of his cock. Her hands replaced Tim's in stroking his thick shaft. It felt so good, his knees felt weak. Then- a tragedy- Sydney let him go before he could come and turned back to Pam. She smiled and leaned in for a kiss.
Pam tried to half-heartedly scramble away while mumbling "Wah! Dick mouth!" But she did not really mean it. She let herself be kissed, and in truth, she enjoyed the new flavour added to the mix.
"Hey..." Sydney whispered after a while. "I want to see you suck him off... If you want to."
She did want to... But she did not want Tim knowing that, so she sighed and rolled her eyes. "Whatever. Come here, pencil dick."
"Ok cow tits." Tim replied and poked Pam in the cheek with his tip in a fit of boldness.
His boldness left him when Pam grabbed him and bit the side of his shaft. It did not hurt too much, but the message was clear.
"Yes ma'am, thank you ma'am," He said quickly.
Sydney laughed and settled on the other side of his cock. The next few minutes of his life would forever be carved into his memory. Pam and Sydney took turns pleasing him. Pam would jerk him off hard as she licked all over his tip, before Sydney would stroke him gently as she took him in deeper. In between they would kiss each other passionately.
Heaven. It was heaven. The only thing that kept him from coming was the desperate desire to fuck Sydney... Or maybe Pam?
No, Sydney! Sydney!
Finally, it was Sydney who stopped it. Without a word she took off her shorts and underwear and she pushed Pam down on the couch. She laid on top of the other woman, her naked wet pussy up in the air inviting him in. "Tim... I want you..." Was all she said before she pressed her mouth to Pam's.
He did not need to be told twice. He took his t-shirt off and shuffled over while saying a quick prayer to the god of whatever was the opposite of premature ejaculation. His cock was so hard it was almost hurt as he pushed the tip in.
Sydney ached with arousal as she felt Tim work his way inside her. She was so focused on pleasuring them both, that her own lust grew to mind numbing levels. She grabbed the hem of Pam's top and yanked it up over her breasts. The woman laughed into her mouth, not breaking the kiss. The bra came next, leaving her large, heavy breasts free to enjoy.
Between Tim's cock driving deeper and deeper into her, Pam's eager mouth and the amazing softness of her breasts, Sydney was losing her mind. It was perfect- she was right where she needed to be, between her two favourite people.
Tim's back pressed against hers as he settled down on top of her, now fully inside. Sydney allowed herself to fully lay on top of Pam, enjoying the feeling of her strong stomach and soft breasts rubbing against her. She melted into both of them, not sure where their bodies began and hers ended. Tim's cock, Pam's mouth, her hands exploring all over Sydney's body- all of it felt amazing.
Her first orgasm came quickly. She stiffened, her whole body thrumming with ecstasy. She wanted to scream- to kick and thrash around but the press of their bodies held her in place, forcing her to feel all of it.
She came two more times, before she felt Tim's breathing quicken, his thrusts grow more frantic.
"I'm- fuck- I'm gonna come-" He groaned in her ear right before it happened.
Sydney held onto Pam with all she had in her, as she felt Tim empty himself inside her. She felt the other woman whimper and try to grind her crotch into Sydney but it was impossible- the angles just did not work out.
So, she held and kissed her until Tim spent himself. He laid on top of the two of them, heaving for breath, his semen leaking out of Sydney. It felt so good she wanted to stay like this forever, but Pam's desperate whimpers were getting to her.
"Hey... Tim. Can you..." She whispered and wiggled herself from under still woozy Tim, letting him settle on top of Pam.
She was about to try to reach between them to somehow get Pam off, when the woman grabbed Tim's softening cock and aimed it between her legs. "Do it." She ground out into his ear. "Please..."
Tim just nodded and pushed his half hard dick into her. Sydney sat back and watched, somewhat awed at his stamina. He started out soft, but he quickly hardened again, pumping away at Pam. Who, in turn, wrapped her thick legs around his waist and hugged him tightly.
For the next couple of minutes the room filled with their grunts and moans, as Tim fucked Pam with all he had left in him. Finally, she whimpered, bit his shoulder and came hard. He grunted and somehow found the strength to thrust into her even harder. Sydney felt herself grow aroused again as she saw Tim come again in such a short time.
What the hell did they feed their kids in that little town?!
Tim rolled off of Pam, feeling utterly drained. He was already mostly out of it after his orgasm, but then... Well... The lady asked so nicely. He sat back and looked down on Pam. She looked gorgeous- all sweaty and messed up. He felt a stirring of regret- did they just ruin their friendship?
Pam looked up at him and flipped him off. Yeah, they're going to be fine.
"Need a break?" Sydney sat next to him, shoulder to shoulder. "I can take over from here," she said with a wink.
He nodded and settled back against the couch to watch Sydney get to work. Boy, this woman really seemed to love eating pussy. He caught Pam's eye as she arched her back, enjoying Sydney's tongue.
They looked at each other for a bit, neither sure what to make of this evening. In the end, they shrugged and decided not to think about it too much.
---
"Hey dipshit..." Pam whispered, with a grin.
"Big words from somebody who slobbered on my knob like corn on the cob last night," Tim replied, feeling pretty good about himself right now.
"I like doing charity. I am a charitable person."
Tim hummed agreement, as he drank his morning coffee. Pam sat beside him, in her usual spot, and reached for the cup he made for her, as was their routine. Both of them being naked was rather unusual, but he decided not to make it a big deal.
"Fucking hell she's too cute..." Pam sighed.
"Yeah. Sleeping angel."
Sydney was laying on the couch in front of them, looking incredibly cute in the morning light. After a few more rounds of lovemaking they all pretty much passed out, tangled up together in the bedsheets.
Now, in the light of day, there were some decisions to be made.
"As you know..." Pam began "I would rather stick a chunk of uranium in my ass than date you..."
"Of course. Same here," Tim agreed.
"However..."
"However...?"
"You know..."
"Do I know?"
"Stop staring at my tits and focus!"
"No."
"Tim, I want to date Sydney."
Tim nodded. He did as well.
"But... I don't want to lose you..." Pam said.
Tim went silent for a while. Then, he said "So... Fifty-fifty?"
"Fifty-fifty..." Pam agreed.
Satisfied with their heart to heart, they sat and drank their coffees in silence. Within the warm tangle of blankets, wide awake Sydney grinned to herself.
She really needed to buy her roommate flowers or something.
Comments
Meadow
Waifu with small boobs: †Sex position that almost completely hides the small boobs: đ
Jon
This is what makes Alfie special. That not only are you good at art, but you are an excellent story-teller as well. Thanks again!
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