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saiyanprincessswanie · 12 days ago

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The Ultimate Risk - Part 2

Pairing: Bucky Barnes x Female Reader

Word Count: 5020

Series Summary: Reader is a full-time college student at 30 years old who is starting over in life. When she loses her full-time job as a waitress, CEO James “Bucky” Barnes steps in with a proposition. Can he sell you on a way to help you by offering a Sugar Daddy relationship? In time who will get feelings first?

Series Warnings: Sugar Daddy au, Reader is 30 & Bucky is in his 40s, trust issues, angst, eventually falling in love, smut, oral (m & f).

A/N: @avengers-assemble-bingo for James Buchanan Barnes - 108th Birthday Bingo

Square: Sugar Daddy (card #4B 024)

A/N 2: Thanks to my beta readers @gremlin-girly & @lfnr-blog-blog-blog Thank you to @nekoannie-chan for reading this. Thank you to @late-to-the-party-81 for my amazing moodboard.

Please Read, Reblog, & Comment. It lets me know you like my work. 😊💜

I do NOT consent to translating or reposting my work on any social media platform, app, or third-party site or run through AI. If you see my work anywhere besides my personal Tumblr & AO3 accounts, it has been stolen.

For three days now you have been contemplating Bucky’s offer. You had researched what a sugar daddy relationship was and it explained to you further what you were getting into. You could be a companion to him, attend his work functions and, in return, he would take care of you financially. There were no strings attached, or so he said, to this deal. You looked at your pro vs con list for the millionth time.

Pro: well-mannered, benevolent, charming, intelligent, protective, caring and handsome. Rent and bills paid. Student loans paid off. Get to work full-time on college classes. Financially stable. Less stress.

Cons: could or should you trust him? What if wants his money back if you break off your sugar daddy relationship? Short-tempered. Can/will resort to violence. Look at what happened with John. What if he wants more than companionship?

Okay, so your pros were definitely longer than the cons. Plus, you knew Bucky from all the times you waited on him in the restaurant. But was that enough? You were still wary about your decision. He seemed like all the attributes that you listed in the pro section just from your interactions with him over the last 6 months at Cecily’s restaurant, he seemed genuine. However, you'd thought the same about John. But Bucky seemed entirely different. The things you'd listed in your pros list had been observational and not always directed at you.

UGH

It all came down to trust. John had ruined that for you when he up and left you without a reason. Maybe it was because you were finally putting yourself first and John wanted to be the center of attention. You sigh again.

“Fuck John.”

This wasn’t about your ex, it was about you getting what you want out of life and starting over. You look at your phone and decide to text Bucky - mind made up.

You: “Hey Bucky I think I made up my mind. When can we talk?”

Bucky: “Hey sweetheart I was planning on leaving soon. We can meet at a coffee shop not far from your place. I heard they’re good.”

You knew the place he was talking about. You liked to go there sometimes in the mornings because the coffee was great but their muffins were even better. It was a five-minute walk and was nice outside.

You: “That sounds great. I will meet you there in a little while.”

Bucky: I can’t wait. See you soon.

You couldn’t help the smile that formed on your face. Someone is looking forward to your company and that just made your day better. You got off your bed and headed to your small closet, looking inside for an outfit your eyes fell on a pretty light green sundress with white flowers on it. You pulled it out of the closet and quickly changed into it. Giving yourself a once over in the mirror you notice how nice the dress looked on you. You put on light makeup and styled your hair. You slip on your white sandals to finish the outfit. Then you grab your phone, keys, and purse as you leave your apartment.

The sun was shining brightly as you walked down the sidewalk. Your stomach was in knots as you got closer to the coffee shop. How would he react to your answer and could you handle what came next? You thought you were going to beat Bucky to the shop when you rounded the corner and saw his Cadillac Escalade at the curb. Walking up to the door of the coffee shop you were greeted by Bucky who came outside and held the door open for you. He was still in a suit, but no tie, and the top two buttons on his shirt were undone.

“Hi sweetheart, so glad that you made it. I just got here a couple of minutes ago. I got us a table in the corner so we could have some privacy.”

“Hi, Bucky, nice to see you too.”

You start to fidget with your hands and look down at your feet for a second. Then, taking a breath you look up into his blue eyes and smile at him. You were trying to ground yourself; anxiety taking hold in your bones. It wasn't working. However, the moment he took your hand and smiled at you there was a sense of relief that washed over you. Like everything was going to be okay.

Bucky leads the way to the table and releases your hand so he can pull your chair out for you to sit in. Once you sit, Bucky takes a seat across from you and smiles. A waitress comes over to bring two cups of coffee with a side of milk and sugar. As she walks away, you make your coffee as you like it.

“Do you need any sugar or milk? I can share.”

He shakes his head no. “I’m fine sweetheart. I like my coffee black no sugar or milk for me.”

You take a sip of your coffee and hum in appreciation. The coffee was always good here. Putting the cup down you looked at Bucky who was smirking at you. It was like he already knew the answer you were going to give him.

“So, I bet you want to know my answer to your sugar daddy offer.” You give him a shy smile as you fidget with your cup.

“Whatever it is sweetheart, I will respect your decision. I won’t be mad if that’s what you’re worried about.” Bucky eyed your fidgeting hands and, sensing your nervousness, reached across the table to lightly but soothingly rub the back of your hand.

Taking a deep breath you decide to give him your answer. “I’ve decided I would like to try out this arrangement.

Bucky breaks into an involuntary smile, quickly scuppered when you narrow your eyes slightly and continue.

"But if - and only IF - you agree to put it in writing."

"That's fair." Bucky nods solemnly. "I planned on doing exactly that but if I can ask... why don't you also tell me what you're worried about? Communication is an important aspect to all of my contracts and I expect you to be able to tell me if there's anything you're unhappy with."

“I’m worried about the violent side you had with John. Is that something I have to worry about with you? I wouldn’t be able to stay with you if you could potentially harm me. Plus I have trust issues thanks to John as well so I’m a little anxious about fully trusting you. I’m also worried about being pressured into a sexual relationship. I’m not sure I’m ready for that.”

His eyebrows rose at your concerns as he tried to take it in. Bucky knew you had anxiety and trust issues so he would have to learn how to show you he wasn’t a bad guy.

“I will do everything in my power to show you that you can trust me. I will earn that from you eventually and hopefully, you will see I’m genuine. As for the money, if for whatever reason we don’t work out I don’t want anything back from you. It will be in the contract stating so.”

Bucky’s blue eyes maintain eye contact with you the entire time he speaks. Bucky looks at you with reassuring eyes as his hand gives you a comforting squeeze and he offers a genuine smile.

“As for my behavior with John I promise you that was a rare occasion. I’m not a violent man and my mother raised me to never hurt a woman. I assure you, I have standards. Lastly, we touched base on this before. We don’t have to do anything you aren’t comfortable with. Right now I’m looking for friendship and companionship only. I hope this sets your mind at ease.”

You grin back at him. This was exactly what you needed to hear. “Thank you, Bucky for going over my concerns. I feel comfortable knowing this will all be highlighted in a contract. Trust for me must be earned and if you ever break it I will not be able to trust you again.”

Bucky grinned at you. “I don’t plan on breaking your trust. I will do whatever I can to build it between us instead. Are there any other concerns or questions you have?”

“No, I think we covered it all. Thank you, Bucky for hearing my concerns and not judging me.” You took another drink of your coffee.

“Any time sweetheart. So, do you have any plans for tomorrow? ‘Cause I was thinking we could go shopping for some formal dresses and clothes? My treat.” Bucky watches as your face lights up in excitement. He hopes to always bring that response out of you.

“Oh my gosh really? That sounds wonderful. I’m free tomorrow.”

You couldn’t contain your excitement and Bucky could only smile back at you. He knew he made the right choice in choosing you to be by his side. This was the start of something special, he could feel it.

The two of you continued to talk about the agreement. He went over what was expected at events like being well-mannered and considerate. Which he already knew you would be. Bucky would keep you by his side at all events, outings, and travels until you felt comfortable enough to be on your own.

You asked questions about his lifestyle and he had answers for you. According to Bucky, he was a self-made billionaire who could happily retire tomorrow if he wanted to. It just depended on some personal things that he didn’t go into. But he did talk about lavish vacations and restaurants that he liked. He assured you that he would spoil you with them soon enough.

Bucky in return asked about your life. You skirted quickly over what happened with John and a wedding that never happened; that left you in financial ruin and with a whole lot of trust issues. You decided that you wanted to go back to college to get a degree in your dream job. How you wanted to eventually pay your bills without struggling or stressing out. By the time you were done talking, it was already dinner time.

“Wow, I’m so sorry I talked so much. I guess when I’m warmed up to someone it’s easier to talk about myself. So, I bet you have somewhere to be.” You bit your lower lip to stop yourself from fidgeting again.

“Sweetheart, I have nowhere to be and I’m enjoying your company.” Bucky winked at you as he smirked.

“Well, if you aren’t busy and are free you could come to my place to order food. It’s not the fanciest place but to me it’s cozy.”

What were you thinking no billionaire would want to come to your dump of an apartment? What a dumb idea…

“Sure, that sounds like fun sweetheart. Let me drive us over to your apartment and we can go from there. Whatever you want to eat I’m good with.”

Bucky got up and tossed some money on the table. He gestured for you to go first but when you reached the door he held it open for you again. Even when you got to his Escalade Bucky opened the door and once you were inside he shut it. You could get used to that. John never did anything like this with you.

Bucky got on the driver's side and drove the short distance to your apartment. Once parked, you both got out and you led him to your apartment building. Heading up the stairs you finally reach your door. Taking a breath you open your door and walk in followed by Bucky.

“It’s not much but I call it home.”

Bucky looked around your apartment and grinned. “I like it. This is a cute little place.” Looking at the paintings on the wall he had to admit they were beautiful.

“Did you paint these yourself?” He asked.

Kicking off your sandals you looked at him studying one of the colorful abstract ones. “Yeah, that’s all me. I used to paint all the time but once I moved here I didn’t have the space for it. It’s one of my favorite hobbies.”

“Remarkable. You are truly gifted. Have you ever thought about selling any of them? With this talent I’m sure you would have buyers, myself included.” He stood with his hands on his hips and head cocked to the side looking at each painting on the walls.

You chuckle a little as you watch him. “I’ve thought about it but again I don’t have the time, money, or space.”

Bucky turned around to look at you. “Consider it done. I will find you space to paint and with me, you’ll have money to invest in this. Plus, besides college, you will have free time to express yourself on canvas. What do you say?”

You couldn’t believe what you were hearing. Finally, you could have free time to do what you love. “I say let’s do it.” You start to giggle again and this time Bucky picks you up and spins you in a circle.

Bucky places you back on your feet and at that moment his stomach growls. “So how about dinner?”

“Is pizza okay? I know a great brick oven pizza place that delivers.”

“Sounds good to me, doll.” Bucky takes his jacket off and places it on the back of a chair. Rolling his sleeves up to his elbows he reveals tattoos on both his arms.

You swore your panties got wet from just the sight. No, you can’t feel this way about him. You were his friend and companion. Clearing your throat you grab your phone and place an order for a pepperoni pizza. When you hang up you call over to Bucky who is still staring at your paintings.

“Hey if it’s okay with you I’m going to change.”

“That’s fine, doll.”

You went to your room and changed into shorts and a T-shirt. As you come out you find Bucky taking a picture of one of your paintings.

“Whatcha doing Bucky?” You watch as he turns around with a grin on his face.

“I wanted to text this to an art dealer I know. He’s my best friend - Steve - who was with me a few nights ago at your restaurant. I wanted to see what he thought of your work.”

You were surprised at the interest he had in your work. Things like this just don’t happen to you. A sugar daddy does spoil his girl though.

"How did you start painting?" "What inspired you?" Bucky asked and that brought a smile to your face.

“I’ve been painting almost all my life. I didn’t take it seriously until I was a preteen. Then my parents enrolled me in art classes outside of school where I could hone my painting.”

You continued to take for another twenty minutes before you both heard a knock, knock! “Pizza is here.”

Bucky goes to answer it and it’s the delivery guy. Bucky pays him and gives him a nice tip before closing the door. He places the box on your counter as you grab plates. You each grab what you want and head to the couch to watch TV. With the TV on as background noise, you both continue to talk again.

You both talk for hours about anything and everything. Before you know it it’s eleven at night. You both are laughing on the couch over a story he told you.

Bucky looks at his watch and frowns. “I’m sorry I’ve kept you up late. I’ve had a wonderful time.”

You give a small yawn and nod. “I’ve had a great time with you tonight. We should do this again.”

Bucky stands and stretches. “We will definitely do this again. For now, I should let you sleep ‘cause tomorrow we are going shopping.”

You squeal a little in your excitement and stand up to hug him. “I can’t wait, Bucky. Thank you for today.”

Bucky was shocked that you hugged him but he smiled anyway. Walking to the chair he takes his jacket and grabs his keys out of the pocket. “You sleep well for me tonight.”

He kisses the crown of your head then turns around and leaves. You both wave at each other before you close and lock your door.

If this is how a sugar daddy relationship works you could get used to it. Putting up the leftover pizza in the refrigerator you head to your room and climb into bed. Tomorrow is a new day and you can’t wait to see where he takes you.

The alarm on your phone went off at nine in the morning. You finally had a good night's rest thanks to Bucky stopping by last night. It was nice to spend time with someone and talk so much. You let out a groan as you stretched in bed. Getting up, you headed to the bathroom to get ready for the day starting with a hot shower. When you were done in the shower and finally dressed for the day you texted Bucky.

You: I’m ready whenever you are.

Bucky: I’m on my way sweetheart.

Twenty minutes later there was knocking at your door. You opened the door to see Bucky standing there with a smile on his face. He was dressed in a red henley shirt, jeans, and boots. Thank goodness he was casually dressed since you were in a lilac shirt, capris, and sneakers.

“You look gorgeous,” Bucky commented.

You smile back at him. “You look handsome as well. I just need to grab my purse and we can leave.”

You place your phone into your purse and place it on your shoulder. Then you grab the keys and head out the door locking it behind you. You walked in front of Bucky as you made your way down the stairs and outside. It was a beautiful sunny spring day outside as you walked to his Escalade and got inside. Bucky got in and pulled away from the curb.

“So where are we off to first Bucky?” You asked excitedly.

Bucky chuckled at your excitement. “I have a few places in mind. Don’t worry about anything ‘cause today is going to be all about you.”

You both talked about the type of places you were going. Some were places that focused on dresses for every occasion. While others were everyday clothes. Not that he didn’t like what you wore. He knew you might want to update some of your clothes and shoes. You on the other hand were more worried about where all this new clothing was going to fit since your closet was so small. You told yourself to relax and that you would figure everything out. Bucky pulled up to the first store. Dresses lined the windows and you stared in shock at how beautiful some of them were.

Bucky watched you as you stared at the shop. You had the cutest expression on your face. “Are you ready to go inside, sweetheart?”

“Absolutely, yes!” You squealed out.

Bucky got out of the Escalade and made his way to your side where he opened the door for you. He offered you his hand as you hopped out. Holding hands felt natural to you as he led you into the store. As you entered you couldn’t believe your eyes; there were dresses EVERYWHERE. A saleswoman appeared out of nowhere and greeted Bucky.

“Ah, Mr. Barnes, we were expecting you. How may I help you?” She asked as she looked between the two of you.

Bucky introduced you to the saleswoman. “We need some dresses for her. We’re looking for both casual and formal wear. I want to be able to show her off at events in the most stunning dresses you have.”

“Of course Mr.Barnes. We will have her try only the best dresses on.” She looked at you now and offered a smile. “If you want to follow me, we will get you started.”

The saleswoman and you started walking towards the evening dresses. There were so many colors and designs; pinks and purples, ballgowns and halternecks. The saleswoman asked what your size was and she started grabbing dresses. She brought them to a changing room for you and you walked into the spacious room. Grabbing the first gown it was black with a slit up the side and was off the shoulder. Slipping your clothes off you pull the dress on and call the saleswoman for help to zip you up. Once zipped up you took a breath and stepped out of the dressing room. Walking out to where the mirrors were and Bucky sat, you bit your lip bashfully.

Bucky's mouth parted when his eyes fixed on you, taking in every inch of your beauty he could. The dress was stunning on you and his hands twitched; desperate to touch you as he watched you do a slow turn in front of the mirror, capturing all angles of yourself. Then when you looked at Bucky he could sense your nervousness so he got up from the chair to walk over to you. He was a foot away from you when he gave you a big smile.

“You look absolutely beautiful, sweetheart. I love this dress on you. The style suits you.” He complimented.

You offered a shy smile back. “Thank you, Bucky. I do like this one very much. But the price is high for it. I don’t think it would be fair to ask you to get this for me.”

Bucky gently grabbed your hands and kissed the back of each one. “The cost means nothing to me. What matters is if you like it.”

You look up into his blue eyes. “I do. I really do love it.”

“Then it is yours. Now, go model some more dresses for me.” He offered a reassuring smile and watched as you headed back to the dressing room.

The rest of the afternoon was pretty much the same. You would try on a new style and color then show Bucky how you looked in them. He was very supportive and vocal about how stunning you looked to him. By the time you were done, you had seven evening gowns for events and five new casual dresses. Where you would put them you had no idea but Bucky was very happy to pay for them all. From that shop, you bought some casual clothes that were nicer to wear if you had any place to be during the day. Then, you went shoe shopping to match all of your brand-new dresses. When Bucky insisted on you getting some Louis Vuitton shoes and a couple of handbags, you thought you were going to cry. You always wanted a pair of each; and here you were picking them out. Once shopping was over, Bucky had told you that you were heading to his place.

“I have the contract ready for you to sign at my place. I hope you don’t mind doll.”

You beamed back at him. “Not at all. I wonder what kind of fancy place you have.”

Bucky chuckled at your response. Hopefully, he wasn’t overstepping at this point as he continued to drive until he got to a luxury high-rise building. Your mouth dropped open in surprise at him pulling into the parking garage. Bucky pulled in and drove until he was in his own parking space. You both got out and he took your hand, leading the way to the elevators. You were silent as you took it all in once in the elevator. Bucky hit a button to the top level and he lightly squeezed your hand in reassurance. Once you were on the top floor you approached a single door in front of you. Bucky unlocked the door and led you inside.

The place was huge and screamed luxury penthouse. The kitchen was the size of your entire apartment. The entire floor was open-concept and had paintings on the walls. You passed by a wall with pictures and immediately recognized the two men from the restaurant, Sam and Steve, next to Bucky.

“These two are my best friends. We’ve known each other for many years. Especially Steve, I've known him since childhood.” Bucky explained as you took the pictures in.

“That must be nice having friends you’ve known for that long. I had friends before but…” you trail and clear your throat. "Anyway, it's just me right now."

“Well, you have me now so that’s gotta count. Right?” Bucky smirked at you.

You giggle a little. “You’re right. I’m so happy that I have your friendship. So you said you had a contract ready for me? Can I see it?”

“Of course.” Bucky led you through his place until you reached his office. You followed him inside and he motioned you to sit in front of his desk. Bucky took a seat in his chair behind the desk. He looked like a man of power sitting there. Grabbing a file on his desk he pushed it forward towards you.

“This is the contract that I had drawn up for you about our sugar daddy relationship. Everything that you asked for is in it. Plus, everything I told you about is also included. The allowance I plan to give you and the part where I will pay all your debts and monthly bills. Please take your time reading it.”

You took the file from Bucky and started to read it. Everything, he just said, was in it. The money, the bills being paid, and even a section about whether both decided on a relationship down the road. Then there was a section that mentioned new housing. How odd. You skim below that and read that he would be getting you a new car since yours wasn’t in good shape.”

“You do want to spoil me. A new car? A new place to live? Are these necessary?”

Bucky chuckled at your questions. “I want only the best for you. Your apartment, while quaint, has no space for all the new clothes, shoes, and purses I bought you. If you’ll allow me I found you a space of your own. It’s owned by my friend Steve. It’s big enough that you can paint in one of the rooms so we won’t have to rent a studio unless you want it. I will leave that up to you.”

You couldn’t believe what he was saying this was way beyond anything you could ever imagine. “I’m truly speechless. I-I never expected this much from you.”

“Like I said before sweetheart, I’m just looking for companionship and friendship. You deserve the world and so much more. If I can spoil you along the way that makes me happy to do so. Now, if everything looks fine why don’t we sign it together.”

You nodded your head in agreement and took the pen Bucky was holding out for you. You signed your name on the bottom of the contract and pushed the document towards him. Bucky grabbed the contract and signed his name at the bottom. Bucky figures he can send a copy of the contract tomorrow to his attorney and friend Sam.

Bucky gets up from his chair and walks to where you are sitting. “Now that’s out of the way, why don’t we get you home? We can discuss your new living arrangements tomorrow and get you a new car then.”

“That sounds like a plan to me. I really can’t wait but Bucky, who is going to help me move?”

“I’m hiring a moving company for you so you don’t have to worry about anything. Let’s keep your new things here until you move. Then when you have a closet big enough we can move it all in.”

“Wow. You've got this figured out already, huh?” You got out of your chair and followed Bucky out of the office.

He led you back out of his penthouse and back to the elevator. Once you reached the Escalade you got back in and Bucky drove you home. While driving you back in silence Bucky reached for your hand and held it while he drove. It was sweet; these little gestures that he made like holding your hand or a kiss on your hands or forehead. You have to admit they made your stomach knot up at times in the best way. But you had to remind yourself this was just a friendship, an agreement between two friends.

Bucky pulled up to your apartment and walked you to the door. Getting your keys, you go to open the door but before Bucky could kiss your forehead you move in kissing his cheek.

“Thank you for the day of shopping, Bucky. I appreciate being spoiled by you. I can’t wait to wear everything that you bought me at some point.”

“Speaking of wearing your dresses, I have a charity function in a few days. I hope it’s not too late for you to join me.” His hand caressed your cheek gently.

“That’s plenty of time for me to know. I can get my schoolwork done before then so I don’t have to worry about falling behind. Thank goodness I only have three weeks until finals. Then I’m all of yours for the summer.”

Bucky had to admit he liked the thought of that. Being able to take you on trips and not worrying about college.

“Alright, well I will see you tomorrow then. Sleep well, sweetheart. Text me in the morning.”

“I will. Good night Bucky.”

“Goodnight, doll.”

You walked into your apartment and closed the door. You sigh thinking of his cute nicknames for you and the way he’s spoiling you. Never have you been spoiled like this before. Glancing around your apartment you smiled. Guess it’s time to move on to a better place.

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