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twice-inamillion · 4 months

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The Company

Taeyeon and IU’s Plan

Smut and Story Building (Sex, Deep Penetration, Defloration, Creampie, Fingering, Blowjob)

Chapter 3

4,315 Words

(IU finds out that Taeyeon has been looking through her phone that filled with her sexual experiences with her boss. Taeyeon is convinced by IU to get a taste and comes up with a plan. Taeyeon gets more than what she can handle. OC gets a little surprised but is more than happy to accept it.)

A few weeks pass, and every time Taeyeon stays at IU’s apartment, she notices hints of your sexual relationship with IU. Anything like cum covered panties, cummed covered skirts and marks on IU’s thighs and chest.

She can’t hold on any longer; she needs to confront her friend about the type of relationship the two of you have. Taeyeon tries to find the looks for the best moment to talk to her about this.

“I’m going to ask her today; I can’t wait anymore. It’s awkward every time I see the two of them together.”

Taeyeon arrives earlier than usual and prepares dinner for the both of them, “Some pasta would be nice and easy to do. She changes into some comfortable clothes and gathers all the necessary items to make the meal.

“Taeyeon, I’m home.”

“Welcome back. I made dinner for us.”

“Aww, that’s nice of you. Let me change.”

“Okay, I’ll set the dinner table.”

Taeyeon sets the dinner table and waits for IU to take a seat before serving her. “What’s the special occasion?”

“Nothing much. I just got tired of ordering takeout and wanted to make something homemade.”

“Haha, you should do this more often.”

“I’ll try, only when I’m done early. Anyways, how was your day? Don’t think we have talked comfortably in the past few days.”

“Hmm… nothing much. Just the same old thing. You know, helping with ranking the trainees, setting up meetings, and doing my duties as the CEO’s assistant.”

“What kind of duties do you have?”

“Just busy stuff like going over his daily and weekly schedule, setting up his meetings, sometimes bringing him his meals or some do simple tasks.”

“Seems like he has you overworking yourself.”

“Ah, no, that’s not true. He also has Irene as the secondary assistant. We share the tasks here and there. It's not that bad, actually, once you get used to it. But there are times when it does get busy, and I come home tired.”

“Is he nice to you?”

“He can be a bit tough, but he treats me nice. He asks how I’m doing, buys me nice things like jewelry, and gives me spending money.”

“Seems like the two of you have more than a boss-and-employee relationship.”

IU smiles and tries to play it off, but Taeyeon teases her, “Omg, are you and your boss something?” IU can’t help but grin, causing Taeyeon to push deeper, “I kind of figured the two of you were a thing. Is it actually a thing or work sex?”

“Haha, why do you want to know? Are you perhaps interested?”

“No! I just wanted to ask since you have been acting a bit differently.”

“Hmm.. okay. I’ll tell you, but don’t tell anyone else, okay?”

Taeyon is now completely invested in finding out their relationship and eagerly nods, “Yeah, I won’t tell anyone.”

“Okay, remember how I told you that my family has financial issues?”

“Yeah, of course. You said that your family was struggling really back, especially your mom.”

“I wanted to help her somehow, so I contacted some people and became his personal assistant. This meant I had to service him at the workplace and him “personally.” I knew it was bound to happen and did it for my mother’s sake. So I had my first time with him. I thought I would hate him, but he’s really caring. He and I aren’t dating; it’s just a work relationship. I’ve been with him for a bit over a year and learned that it’s better to take the initiative and serve him than for him to act on it. If he has to ask for it when he might fuck you based on his mood, and trust me, that might be a bit dangerous. So I learned to read his mood and service him.”

“Oh wow. I didn’t know it was that serious.”

“The pay is really good, and the benefits are much better. This is one of the reasons why I have this apartment, and my mom is living in a nice house.”

Taeyeon hesitants but asks, “By the way, how far have you gone? Like, what do you do?”

“Well… the first few times, it was just regular sex, then it was a handjob and blow job. As time kept going, we would do more stuff, like me giving him head in his office or having sex in there too.”

“Have you two done anal?”

“Ahh, I haven’t, but he’s done it with someone else.”

“Who?”

“Irene, his other assistant.”

“He fucks her too?”

“Yeah, and let me tell you this. Their relationship is much different than mine. She didn’t want to service him and learned the hard way. Anyways, are you interested?”

“What do you mean?”

“Don’t try to hide it, Taeyeon. I know you looked through my panties in my hamper and went through my phone.”

Taeyeon panics and lies, “No, I didn’t do that.”

“Don’t lie, that phone is something that he gave me. It screen records every time someone tries to log in. So I know that you’ve been looking at my videos of him fucking me.”

Taeyeon panics, and it shows. IU reads Taeyeon like a book and teases her by asking, “Are you interested in him?”

“Ahh, no! I’m just interested.”

“Lies, I’ve heard your moaning during the night. I know that you’re sexually interested and frustrated.”

“No, you’re wrong.”

“I mean, if you are, and I know you are. It will make my job easier. There are so many things I have to do, and if he’s busy with you, then that means I have to spend less time servicing him. What do you think?”

“Umm… I don’t know.”

“I’ll even help you. I’ll tell you the best time and even get him a bit tipsy for you, haha.”

“You’ll help me?”

“Yeah, you’re my friend. It’s not like I have anything to lose. Look, I’ll even show you some pictures from today,” as IU pulls out her phone and shows Taeyeon a video of you getting your cock sucked and you cumming in her mouth and face. IU notices Taeyeon slide her hand between her legs and rubs herself under the table, “Don’t tell me you don’t see yourself being in my place. Just imagine his hot cum on your face and going down your throat.”

“Hmm… you said you’ll help me, right?”

“Yeah, I’ll take care of everything. You just got to follow my advice, and you’ll be good.”

“Okay, I’ll do it,” causing IU to smile.

————

“Is that the last schedule for the day?”

“Yes, sir. You’re done for the day. Are you planning on dining out?”

“No, I just want to go home and rest. This was a busy and long weekend; I wanted to have a drink and relax. I’ll probably go out tomorrow.”

“Would you still like me to service you later tonight?”

“Hmm… actually, how about we share a drink?”

“It would be my pleasure, sir.”

You gather all your belongings and head to your apartment with IU. The two of you wait for the elevator and can’t help but notice the large height difference between the both of you, almost a foot apart. The elevator door slides open, and the two of you enter and scan your keycard to the top floor.

Arriving at the top floor, you walk down a long hallway towards the single, large door on the floor and insert your code to enter, “Finally, back home.” The two of you take your shoes off, leave your items on the table by the hallway, and sit on the large couch.

“Would you like me to serve you the usual?”

“Yes, please.”

IU heads towards the kitchen and to the alcohol cabinet and grabs a bottle and two glass cups. She pours the both of you a drink and walks back. “Here you, sir.”

“Thank you.”

“You’re welcome.”

“I like your initiative, Ji-eun. You’ve become a reliable assistant.”

“No, thank you, sir. For the opportunity to serve you and the help to my family.”

“Ahh, yes. How’s your mother doing?”

“She’s doing well, thanks to your generosity.”

“No need to thank me; it’s all due to your hard work.”

IU grabs the bottle once more and pours another drink as you enjoy the view from the top floor of the building. Watching the sunset is one of your favorite things after coming home from a long day.

“Would you like me to order you takeout, sir?”

“Sure, that’d be great.”

“What would you like?”

“You can choose.”

“Okay, I’ll place an order.”

You place your drink down and change into something more comfortable while waiting for the food to arrive. IU sets the table, cleans a bit of the living room, and places your items where they belong. “Would you like another drink?”

“Yeah, I could go for another one.”

She serves you another drink, and you take small sips as you continue to enjoy the view from your living room couch. You and IU have a small conversation about some of the schedule for next week and about the process of the trainees when IU’s phone pings. “Sorry, sir. It’s the delivery person; I’m going to go down to the lobby and meet them. I’ll be right back.”

“Okay, sounds good.”

You walk to the kitchen, open the fridge door, and grab a couple of beers for the meal. You wait for IU to arrive and check your messages. When you hear the door ring go off, signaling that IU was coming inside.

“Sir, I’m back.”

“Nice, I grabbed a couple of beers for the two of us.”

“Sir, I met Taeyeon in the lobby and asked her to join us. Would that be okay with you, sir?”

“Yeah, that’s fine.”

“She’ll be coming up in a few. She just went to get changed.”

“Okay, let's get the table ready for three.”

After a few minutes, the doorbell rings, and IU opens the door for Taeyeon. “Hello, sir. Thank you for allowing me into your house.”

“It’s no problem; you’re welcome anytime; come take a seat.”

Taeyeon sits on the couch across from you," Would you like a beer?”

“Yes, I’ll take one.” he grabs a beer and opens it. She crosses her legs, and you catch a glimpse of her not wearing any panties. You try not to look at it, but you can’t help but admire her thighs.

“The pizza is ready.”

“Thanks; actually, do you think it would be better to eat here in the living room since it’s pizza?”

“We could do that,” says IU.

“I’ll help you, Ji-eun,” standing up and helping bring the plates to the living room table.

With everyone sitting down, you all grab a slice of pizza and a beer and start to eat. You ask Taeyeon about her week and if she’s comfortable as the vocal coach.

“I like it here; the place is beautiful, the staff is nice, and the trainees are very hardworking.”

“That’s good to hear. Better than SM, huh.”

“Haha, yeah, it is,” she laughs.

IU mentions that she’s been hearing positive feedback from the trainees ever since she started and congratulated her on a good job. Taeyeon smiles and puts her feet on the couch, giving you a better view of her private area.

You try not to look, but you can’t help your curiosity and eye her every time she moves her legs. IU notices this and asks, " Taeyeon, would you mind passing me a napkin?”

“Sure,” and she reaches for the napkin, allowing you to get a glimpse of her cleavage under the oversized shirt. IU looks at you and smiles, knowing that the plan is working.

“Like what you, sir?”

You turn around to IU, “What do you mean?”

“I asked if you liked what you saw.”

You see IU’s smile and turn to Taeyeon and see her smile. “What’s going on?”

IU says, “What do you think, sir? She wants you.”

“Is that true?”

“What do you think? I wouldn’t give a show to just anyone,” says Taeyeon.

“Hmm… So the both of you planned this.”

“You catch on quick, sir.”

“Okay, I’ll play your game. Taeyeon, you must be aware of the type of relationship I have with Ji-eun, right?”

“Yes, I’m aware.”

“And you’re fine with that?”

“Yeah, I am.”

Calling her bluff, you stand up, walk towards her, and extend your hand. “Alight, since you want to play, we can go right now.”

“R…right now?” looking at IU, who only smiles.

Knowing what will happen, she takes your hand and follows your lead to one of the bedrooms. The both of you hear a small chuckle from IU, and her saying, “Have fun,” before you close the door.

“You want to play? Let's see if you’re game,” and sit on the one-seater coach in the room.

Taeyeon stands there, confused about what you mean. “Strip.”

Taeyeon is caught off guard by your command and hesitates. You repeat it once more, “Strip.” Understanding you’re serious; she stands before you crosses her arms, and removes her oversized shirt and then her loose, small shorts.

In front of you is a completely nude Taeyeon. She has small breasts and a clean, shaven cunt. Without saying a word, you scan her body, from her feet to her head. She turns around and gives you a view of her behind, “Amazing. I can’t believe a member from Girls Generation is standing in front of me, nude.”

You signal her to approach you and say, “Come over here.” You grab both her hands and her right in front of you. You lick your index and middle finger and rub her lower lips. She moans at the sudden touch of your warm fingers against her cold skin. Using your two fingers, you trace and swirl the outside of her lips until you feel her moist.

You remove your fingers, pull her towards you, and pick her up. She suddenly yelps from being picked up and notices you walking towards the bed. You toss her onto the bed and watch her reaction as you spread her legs wide open, giving you an embarrassed look. She tries to cover her pussy, to which you tease her and say, “I guess you’re all talk and no game,” giving her a smirk. She gets offended and removes her hands out of pride, responding, “I’m not all talk; I can back it up, too.”

“You’re sure about that?”

“Yeah, I am.”

“I’ll give you one last chance to back out.”

“Don’t need it, I can play along.”

“Alright. Let’s play.”

You remove your shirt and shorts and toss it to the couch. Taeyeon’s heart begins to race as she’s focused on your boxers and sees you pull them down, revealing your semi-hard cock. You pull her towards you and her folds once you say, “You have a really nice pussy right here.”

“You think so?”

“Yeah. I can’t wait to fuck you,” grabbing your cock and pressing it against her lower lips. She pushes your cock away and says, “Wait, you’re not going to wear a condom?”

You stop and are surprised by the most ridiculous question and reply, “What do you mean a condom? I only fuck, raw. Why? You don’t want to?”

No, I was just wondering. I heard that it’s important to wear a condom.”

“I check myself regularly, so I’m good. Are you?”

“No, I’m good.”

“Okay, then we’re all good to continue, right?”

“Yeah,” turning her head around and thinking of all the possibilities of fucking without a condom.

You grab your cock with your right hand and give it a few pumps and press it against her lower lips. You look at Taeyeon and see her face of anticipation, waiting for your next move. With your hardened cock against her entrance, you smack it against her folds right before inserting yourself inside of her.

Taeyeon groans from the pain of your cock making its way through her tight walls. “Fuck… you’re so tight!” as you shove more of your cock inside her. Due to the pain, Taeyeon grabs onto the bedsheets with all her might.

Suddenly, Taeyeon screams when you shove your whole length inside of her in one go. “Wait…Wait… pull out, pull out, you’re breaking me!”

Seeing her in pain, you pull out your cock, and caress her cheek, “Are you okay?” Taeyeon replies, “You’re too big; I thought it was going to die. Give me some time to get myself together.”

‘Wait… don’t tell me” as you look down and look at the tip of your cock covered in a thin layer of red.

She nods her head in tears and says, “Yeah, it’s my first time.” You’re surprised by her comment and would have never known that this would be her first time, but the idea of being her first man makes you hard again.

You grab a tissue, get yourself cleaned, and reassure Taeyeon that you’ll make it pleasurable. She nods and wipes the tears off her face before you move on to insert yourself once more.

With your cock at the entrance of her, slowly insert your length; Taeyeon groans from the slight pain in her walls and begins to stretch to their limits, “Ow… you’re still too big.” You get on the bed, get on top of her, and begin to kiss her neck and play with her breast as you move inside of her.

Taeyeon slowly forgets about the pain and focuses on the pleasure of your kissing and her tits, “Hmm, yeah… that feels good, don’t stop.” You move towards her breast and take her nipple into your mouth as you play with the other. She continues to moan and let free of her nipple and continue to thrust your cock.

Taeyeon wraps her arms around your neck now that she’s comfortable with your length. You increase the pace of your thrusting, causing her to moan and even laugh, “I can’t describe the feeling, but it feels so good!”

“Just wait, it's going to feel better,” as you place her into a mating press. With her legs pushed back, you do a strong thrust, each other’s pelvis smacking against each other. “How do you like that? Can you feel it deep inside you?”

“Ahh.. yeah, I can feel the difference. My womb is taking the shape of your cock!” Her hands move towards her breast, pinching and twisting her nipples as she feels her orgasm coming.

Seeing her pleasuring herself, you can’t help but tease her as you focus your focus on her clit. Taeyeon yelps, asking you to stop because she can feel an overwhelming feeling approaching.

Instead, you place it between your thumb and your index finger and give it a nice pinch. This causes Taeyeon to instantly cum, as you feel a rush of fluid covering your cock. You pull out and enjoy the scene of her orgasm as her body violently shakes. You watch as she rides her orgasm and decide to tease her, so you insert your middle finger and begin to thrust inside her cunt. “Don’t… don’t do that, you’re going to make me come! Stop!” It didn’t take her long for her to reach her second orgasm. “Ahh, fuck! I’m cumming!” as a gush of fluid sprays and her body spasms.

“Wow, I didn’t have to do much. Seems like you don’t relieve yourself often, but that won’t be a problem now that I’m here. You’re going to be a good fucking with me, but now that you had your fun, it’s my turn.”

“Wait, what are you doing?”

“I need to get my fill too, you know.”

“Please… wait,” not letting her finish her sentence as you insert your cock inside. She throws her head back and screams, “Oh fuck! You’re going to mess me up inside!” Her walls tighten around your cock, not used to having your massive length inside of it.

“Your walls want to squeeze my cock, fuck you feel so tight.” You start to pump your cock inside her slippery walls, feeling all the grooves and crevices of her meaty flesh.

You listen to the beautiful sound of Taeyeon’s moaning as you thrust inside of her for what feels like ten minutes. Taeyeon is a complete mess; her hair is ruined, and her body is all sweaty. The tipsy sensation has disappeared, and let her know that you’re about to reach your peak, “Fuck, I’m about to cum.”

“Wait… what did you say?”

“I said I’m about to cum. Where do you want it?”

Puzzled, she tries to come up with an answer, and it is taking longer than what you’re used to. Not wanting to hold it in any longer, you decide where you want to bust your load. Feeling the weird feeling of your cock throbbing your cock she says, “Outside, do it outside,” but it's too late.

The amount of time she wastes on deciding, you end up making the choice for her. You pull your cock out and do one last thrust when you hear her say she wants you to cum outside. Instead, all she hears is, “Fuck! I’m cumming!” Her eyes widen when she hears your comment, and she is bombarded with a large wave of cum flooding her womb.

She cries, “So hot! Pull out!” That only makes you want to shove your cock in deep and paint her womb white.

After finishing your orgasm, you notice Taeyeon looking at her bulging belly, filled with your load. You pull out and watch as she presses her fingers on her stomach, causing a large amount of cum to ooze out. “I told you to do it outside.”

“You took too long, so I made a choice. Plus, I normally cum inside of my girls, so there shouldn’t be an issue, right?”

“But I’m not one of your girls. I’m not IU or Irene.”

“Yeah, you’re right. You are not them, but since you took my hand, you’re mine now.”

“You don’t own me.”

“Haha, says the person with the cum of their boss inside of her.”

She sees your smirk and realizes that you’re right; she does have her belly full of your cum right now. “Don’t smirk.”

“You know, I’m right. How about another round?”

“Another round?”

“Yeah, I mean, if you’re up for it.”

Taeyeon’s pride doesn’t let her back down; she wants to wipe that grin off your face, even if it means going another round. She looks down at you and notices your hardened cock. “Alright, I can do another round.”

“Haha, alright. Let's change the scenery,” as you extend your hand. She takes your hand, and you walk her to the balcony. She looked down and saw the campus and trainees walking in groups back to their dorms after a long Friday night.

You kiss her nape, which causes her to shiver, and her nipples harden. “Put your hands against the railing.”

“Why?”

“Don’t worry. Just let me lead, and enjoy.”

“Okay.”

You raise her right leg up in the air, and with your left hand, you position your cock to her entrance. “What are you do… ahhh” as she feels your cock penetrating her cunt once more. The both of you spend the whole night fucking throughout the penthouse, the balcony, living room, kitchen, and shower. Every time you move locations, you make sure to make the two of you get to orgasm.

————-

Taeyeon wakes up on the bed, looks around, and notices you are gone. She gets up and looks at the many stains throughout the bed, which makes her remember the night she had. She takes a cold shower to wash the stains of fluid on her body, “Ugh… I feel so full.” She presses her stomach and notices a white cream liquid oozing out of her. Pressing her belly harder, a gush of cum squirts out, covering the shower floor cum, “Fuck…that’s too much.”

After her shower, she changed into her clothes and walked out to see you in the living room, reading a newspaper. She walks towards you, “Good morning,” to which you reply, Good Morning, Taeyeon.”

As she walks towards the kitchen, she turns around to ask if she could grab something to eat when she sees IU on her knees. “Ji-eun! What are you doing?”

IU turns around with a smile on her face and replies, “Good Morning, Unnie. I made breakfast, by the way.”

“Why are you going down on him?”

“Oh, I’m having breakfast too. Want some?” as she holds your cock in her hand.

“No!”

“Come on, it's good.”

“No.”

“Are you sure?”

She looks at her friend’s satisfied face and remembers the videos she has masturbated to before. She looks at you and back at her, giving her a reply.

You woke up this Saturday morning full of energy. After going on a run early in the morning, you return and enjoy the breakfast your assistant, IU, made for you. You give her a treat as a reward for a job well done.

You turn, you’re done reading your newspaper, set it on the table, and enjoy the sight in front of you. “It’s nice to see two friends sharing a meal together,” you say with a slight grin.

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