Author's note: First I start by saying I welcome all comments and criticisms if they're relevant to the story and reasonable. Some people have been commenting that they don't think Pepper would be this insecure and yes I know that, but anyone can be insecure at any time. This story is about Pepper's past slowly coming out and she has things from her past that will come to the surface that she forced out of her mind for a reason and these are things that she doesn't want to remember and they don't make her feel good about herself and the high school reunion was the start of things for her. I thought people would understand that through the writing but obviously I failed so I'm explaining why I made her that way since it wasn't obvious in the writing. If that's too out of character for you and you choose not to keep reading then be my guest. Or if you like the story then maybe stick around to see it play out and you'll see why she is insecure. Happy Reading.
It was just after noon and Tony sat in the chair picking at the room service spread he ordered while he watched Pepper sleep. He had the tv on mute and the curtains just gently opened. He already showered and dressed. Watching Pepper was the most interesting part of his day. He watched the way her body spread out over the bed and her one long limb was exposed. He watched the gentle rise and fall of her chest and back. He was admiring her from a distance when she woke suddenly and lifted her eye mask.
"Tony," she said with a hint surprise in her tone.
"Expecting someone else?" he teased as he kept eating his various pieces of fruit.
"No I just didn't expect you to be awake and dressed," she said sitting up.
"There's tylenol and water on your nightstand and plenty of food here. I didn't know what you wanted so I ordered everything," he said motioning to the impressive breakfast spread in front of them.
Pepper grabbed for the tylenol and water and she downed the pill quickly. She got up and went into the bathroom where she took her birth control and relieved her bladder. When she came out she took a seat on the other chair and looked over the breakfast spread. There was eggs, bacon, toast, french toast, lots of fruit and various spreads and jellies. Pepper grabbed a plate and put some eggs and fruit on it. She pinched a piece of fruit and put it in her mouth.
"So are we going to talk about yesterday? How do you think it went?" he asked.
"You're definitely selling it," she said.
"Well it's true and it's making lover boy jealous. What did you like about that guy anyway?"
"He was the coolest guy in school. He was always so confident and he was funny. In a very corny way but he always made me laugh,"
"Personally he seems like a real dud to me," Tony said.
"Well he's changed. Twenty years is a long time. But it doesn't matter he's married anyway," she said.
"Do you regret never trying with him? Tony asked.
"I don't know. My life would be totally different. I couldn't work for you if I had a husband," she said.
"Why is that?" he asked, looking at her inquisitively.
"Well I mean I could. I just don't know if it necessarily would have worked out. I mean how much time would I really be able to spend with him?" she said.
"Is that something you wish for? a husband?" Tony asked, making sure to look her in the eye.
" Well I don't necessarily think I need to get married but I don't want to die alone," she said.
"You won't be alone. You'll have me. You know I'll be alone," he said quietly and it made her sad.
"I don't regret not trying. He had all of high school to shoot his shot and he didn't. Right?" she said trying to be optimistic but Tony could see she was still upset.
"If we went to high school together I would have asked you to every dance. I would have asked you out every chance I got. The red hair it's a weakness,"
"What changed you?" Pepper asked.
"Changed me?" Tony questioned. He wasn't sure what she meant.
"How did you go from dates to one night stands?"
Tony locked eyes with Pepper and he could feel himself squirm.
"I don't really know. I guess I just kind of got busy and work is more important than anything. But I'm a man and I have needs and maybe it's not right but there were girls willing to sleep with me and I took advantage of the situation," he said looking away.
"I guess I understand that. I keep things casual too. It's hard to really date and get into a relationship with this kind of job. We're kind of in the same boat. Don't you ever get lonely?"
"I'm never alone. I have JARVIS and DUM-E and the others," he said avoiding her gaze.
"Pepper, do you want to be CEO? Because I feel like you're not happy and you're living with some kind of regret. I wish you would have told me what you told me last night before I made you CEO," he said.
"No that's ultimately what I've been working for since I started at S.I. Why do you regret your decision?" she asked.
"Not at all. You deserve it,"
"I'm so grateful to have it," Pepper reassured him.
"Do you remember what you told me last night?" he asked.
"You mean about Amanda?" she said looking down at her plate.
"Yes," he said.
"I'm not gay if that's what you're asking," she said.
Tony breathed out a sigh of relief, not that he wouldn't accept her if she was gay but gay meant he was out of the running.
"Bi?"
"I identify as straight. Amanda is gay and I'm the only person she ever told. Now you know so keep quiet,"
"Of course,"
"I've known since high school. We kissed once during a game of seven minutes in heaven,"
"What does one have to do to get seven minutes in heaven with you?" Tony teased.
"Tony I'm trying to confide in you. Are you going to be mature about this?" Pepper said.
"Yes of course, but I'm a guy you know I'm going to think about it you can cut me a little slack" he said.
"Anyway I had a whole bottle of wine and I confided in her that I've been feeling you know…. frustrated lately and we were talking about high school and I told her how much I always admired her and I had sort of a girl crush on her and she kissed me and offered to take care of me and I didn't stop her. It was a nice experience but I don't think I would do it again,"
"What did you guys do? I'm on the edge of my seat here. I need details to fully understand what happened," Tony said, starting to get a semi.
"You're a pig,"
"Ok ok I'm sorry. Look I'm sorry you've been frustrated. But I'm glad you've taken care of it. And your secret is safe with me," he said.
"I can't believe you haven't tried to pick anyone up? There's lots of beautiful women here," Pepper said as she got up from the table and she was taking out an outfit for the day.
"Why would I pick anyone up when I'm here with you?" he asked.
"I don't know. It doesn't take much for you to catch the eye of an attractive woman,"
"But not the red heads that I love so much," he said, making a sad face.
"Maybe you're just not meant for redheads," she teased.
"Don't say that. I feel like I'm being stabbed in the heart," he said dramatically.
Pepper rolled her eyes at him playfully.
"Look I'm going to get dressed and go for a run on the grounds since there are so many acres here. Feel free to do whatever you want. We don't have to be at the dinner until seven," she stated.
"Can I join you?" he asked.
"You want to run?" she asked with surprise.
Tony stood up and almost had a standoff with her.
"I do. In fact I think I'm going to wipe the floor with you. And I think we should bet on it'" Tony challenged.
Pepper smiled at him.
"And what is it that you'd like to bet?"she asked.
"Go on a real date with me,"
"You can't be serious," she said.
"Why can't I be?" he challenged, stepping closer to her.
"Because that would be totally unprofessional and you're not the relationship type of guy,"
"I'm not your boss anymore. And I'm not really the one night stand guy anymore so there really isn't much else for me to do. There's no reason I can't take you out for a nice dinner,"
" I know your game Mr. Stark. You want to get laid and if you don't do the one night stand thing anymore then you have to go on actual dates and actually make an effort to get laid. So is that why you volunteered to be my date? Did you think you were going to get lucky?"she asked, getting even closer to him.
"No Pepper I'd never think for a million years I could ever get lucky enough to be with you like that. I just thought it would be nice. If you don't want to bet then we can just go for a run," he said, going through his clothes to find something to run in.
"No you know what I will take that bet. Once we get a feel of the grounds and decide where we're going to start I will race you and if you win you can take me on a real date. I'm sorry for what I said but you don't have the best track record with women," she said quietly.
"It's ok. It's to be expected. What do you want if you win?" he asked.
"Since I'm the CEO you have to be my PA for a whole day," Pepper said.
Tony had a look of terror wash over his face but he needed that date with Pepper. Pepper was smiling at him waiting for his response.
"Or we can cancel the bet if you don't like my terms," she suggested.
"No you're on," he said without hesitation.
He knew Pepper was fast but he would win that date with Pepper. There was no other option.
The two of them changed quickly and stopped at the hotel store for some electrolyte water and the front desk to get a map of the property. They walked out front and scanned the map until they found the path that led to the large lake.
"Well we can race first and then do our laps or we can do our laps and then run at the end," Pepper suggested.
"Let's do our laps first," Tony said slyly, hoping to tire Pepper out.
What he didn't know was that she did track & field in high school and she completed several triathlons and was skilled in long and short distance running and she's been endurance training for years. The truth was she was going to wipe the floor with him.
"Ok judging by the size of the lake I say 3 laps around should be 1 mile and I usually run about 3 miles," she said.
"Ok and what about the race?"
"We start at this tree here and go around the lake and whoever passes the tree first wins," she said.
"Ok let's go," he said as he started jogging backward.
Pepper was a few paces behind watching Tony show off. Her ear buds were playing lots of great tunes from the eighties most of it being hair metal. Since rediscovering her past she has been more into the music of her youth than her current playlist. She was nearing the one mile mark when she dusted Tony and now she set the pace. She knew he was suffering but he insisted on going with her.
Tony was a few paces behind and he was entranced by Pepper's long legs and gazelle like movements. He decided to slow down and save his energy for the race since getting a date with Pepper was the most important thing he had to do today.
They finished their 3 miles in a little under half an hour and they were taking a rest and taking small sips of electrolyte water.
"I just need two more minutes and I'm good to go," she said as she stretched her hamstrings.
"I'm ready now," Tony said cockily.
They took their places at the tree and they agreed to go on the count of three. They took off and Tony was running as fast as he could and he left Pepper in the dust. Pepper was pacing herself and increasing her speed every so many paces and finally she was on track with Tony who was losing steam with only a quarter of the way left. They rounded the last curve of the lake and the tree was in insight. Pepper continued her pace slowly increasing while Tony was struggling to keep up. Tony forced himself to go at full speed and he took the lead over Pepper again with only a few feet left when Pepper suddenly started to take the lead and Tony snapped into action and tackled her to the ground. Pepper hit the grass and she was going to kill Tony. She tried to get up and he was on top of her.
"I finally got you under me," he teased and then when he saw Pepper's eyes he regretted it instantly.
"I'm going to kill you," she said as she tried sitting up.
"What?"he said.
"You tackled me and you're lucky I didn't get hurt," she said angrily.
"You're just mad it was a no win,"
"Oh I won," she said.
"We can't be sure because I tripped and I took you out by accident," he said nervously.
"Oh really I'm pretty sure you tackled me because you were about to lose," she said.
"I had to do something. I was going to lose my date," he blurted out not meaning for the date part to be said out loud.
"Tony I won fair and square,"
"You're right. You did. I'm sorry," he said as he got up and helped her up too.
She bent over for a minute to catch her breath and slowly sip some water. This race was so tough she had some side stitches despite all her training. Tony was an even bigger mess. He was hunched over and he nearly vomited. He was really upset and he didn't know how he was going to get a date with Pepper now. Pepper watched him as he kicked the ground like a kid who struck out in baseball.
"Tony I-
"Congrats you got yourself a new assistant for a whole day when we get back," he said as he started stalking away.
He was angry at himself. He should have won. He needed to win.
"Tony wait," Pepper said as she caught up to him.
"Are you mad?"
"Just at myself, but it was a fair race so nothing to be mad at," Tony said with a tone that made his disappointment more apparent.
"I promise I won't be too hard on you," she teased.
"I will do whatever you need me to do," he said silently, cursing himself for losing this bet and trying to figure out how he can get another date with Pepper.
"Well let's not worry about that yet. Let's get lunch and get ready for the dinner party tonight," she said as she went into a light jog towards the lobby.
….
Back in the room things were awkward as they were getting ready with one bathroom. Tony let Pepper shower first and she dressed when he got out of the shower but they both needed the mirror to finish getting ready. Tony needed to shave and Pepper needed to start her makeup. She wrapped on the door lightly.
"Are you decent? I need to start my makeup" she said.
Tony opened the door and he was in his towel.
"I asked if you were decent" she said as she pushed past him to the other sink.
"You know I've never been decent," he teased.
Pepper tried to ignore the fact that Tony was only a few inches away from her with only a towel to cover him. She started her makeup and focused on each task so that she wouldn't be distracted by Tony. He went out to put on some boxer briefs and he re-entered to do his hair.
"Is that better?"he asked.
"That's no more decent than the towel," she said with a laugh.
"Pepper you've seen me naked plenty of times in the last ten years," he pointed out.
"Yes and my eyesight is still recovering," she teased knowing he would be really annoyed.
"I've never had any complaints from any women before. In fact when I google myself there's a website kind of like metal sludge only it's ranked by the lovers of famous businessmen such as myself, Elon Musk, zuckerberg, and many others. They rank our appearance, performance, endurance, hygiene and package. You should give it a read. You might be surprised by what you find," he said with that smug look Pepper absolutely detested.
"The fact that you google yourself is just another example of your ego exploding. And whatever it says on there doesn't matter because if any of these hoes you've slept with actually spent any time with you before 11 pm they would see what a complete tool you are," she said as she threw her eye pencil back in her makeup bag and went into the closet for her dress.
"You're only lying to yourself. If you really thought I was that big of a tool why did you stay all these years?"he shot back.
"To become CEO,"
Tony for once had no words.
"I'm going to be getting dressed so please don't just barge back into the room. Give me a warning please,"
"Always," Tony said as he finished shaving and now began to trim his goatee lightly.
He was thinking about the sleeping arrangements and if she was going to say anything about the fact that there was only one bed. He was so excited he had to keep thinking about Rhodey and other things to turn him off. He didn't want Pepper to think he was just trying to sleep with her. He splashed on some Hugo Boss cologne and opened the door a sliver.
"Is it ok to come out?"he asked.
"Yeah I think I need help with my dress.
Tony was still in his underwear when he came out to help Pepper with her dress.
"What do you need?" he asked, coming up behind her.
"The straps are all twisted," she said, putting her head down and her hair over her shoulder to allow him access.
Tony grabbed the straps gently and she could feel the heat coming off of his skin. When his fingers brushed against her skin they both felt a shock to their skin. Tony untangled the straps gently and his fingers grazed her again and he was in awe of how soft her skin is. And her perfume was wafting straight into his brain.
"Pepper that perfume is beyond amazing. Is that new? That's not what you normally wear" Tony said, noticing an unfamiliar smell.
"You're very observant. It is different. This one is Givenchy Very Irresistible" she said.
"Well they made the perfect fragrance for you because you are irresistible," he said.
Pepper hit him playfully.
"You don't have to play up the compliments and flattery, it's just you and me," she said.
"Who says I'm playing it up?"
"Tony get dressed," Pepper said dismissively.
Tony was all dressed except for his tie being crooked. She watched him in the mirror struggling with it and she just waited to see if he was going to ask for help. He undid his tie with frustration and started again and that's when Pepper stepped in and she grabbed his hands and again they felt a shock and they locked eyes for a moment.
"I got it," Pepper said as she fixed his tie occasionally catching his eye while his eyes remained locked on hers the entire time.
"Who's going to tie my tie now that you're CEO?"he asked.
"I'll have to teach you,"
"I had it just a little bit crooked," he said as he took her hand and they headed to dinner.
"You look beautiful by the way," he said.
"You tell me all the time,"
"Does it make you uncomfortable? Should I stop? You know I know you're smart and funny too. And honest and trustworthy. And I've had a lot of PA's before you and they weren't very good. And imagine they quit on me,"
"I can't imagine why. Could it be that you slept with them? Or maybe completely ignoring your schedule or showing up late all the time or wrecking your suit, four minutes before a board meeting? And that's just a few examples,"
"Here we are. It's showtime," he said leading Pepper into the dining room.
Tony was trying to pretend he wasn't hurt by Pepper's constant reminders of his past. He was trying to be a changed man for Pepper and show he could be responsible and mature.
They found their table and place settings and took a seat. Pepper was seated next to Brad Stevens and Tony was on the other side of her. She was pretty sure that Lisa also did that on purpose so she would have to see Brad with Marisol. But lucky for Pepper Tony was the best date ever.
"So Brad what is it that you do for work?" Tony asked.
"I'm a physical therapist," he said.
"Helping people is a good career. But saving the planet from certain death is pretty good too," Tony said with a smug look in his face.
"No one here can compete with that," Brad said.
"Let's decide on what to eat," Pepper said nervously.
"I'll have the steak medium rare," Brad said as he flipped his menu closed.
"Steak sounds great. Make mine rare please," Tony said.
Pepper looked at him as if he had three heads. She has never seen Tony order a rare steak in all the years she's worked for him.
A waitress put a few small plates on the table and Tony stopped her.
"Can you please tell me what that dip is?" he asked as he looked at the plate which had crackers and a mystery dip.
"That's cranberry jalapeno cheese spread," she said.
"That looks great thank you," Brad said as he shoveled a rather large amount onto his cracker.
"Brad can totally handle the heat. He won a contest once for eating the fire wings at this place called Hot Hot Tamale. They had his picture on the wall until they closed. No one else could ever finish the challenge. It was twelve fire wings," Pepper said smiling.
"I can't believe you remember that. I still have the t-shirt," he said.
Tony scooped the same amount that Brad did and ate a cracker and he was instantly hit with the fire feeling on his lips and tongue but he refused to be shown up by Pepper's old crush.
"Tony what are you doing? The wedding is tomorrow morning. Do you really want to suffer all night?"
"Pepper I'll be fine. I can handle hot pepper's just fine. I'm dating you after all," he said and got a laugh from everyone in the room.
"She is a firecracker," Brad said as he smiled at her.
Pepper blushed and Tony was not happy.
"Please excuse me, I need to use the mensroom," Tony said, getting up from the table.
Tony went into the mens room but decided to use the stall for privacy so he could check updates from JARVIS on the house and the business. He walked passed two guys by the sinks that didn't bother to glance his way. When a very interesting conversation was taking place that caught his ear.
" Brad tell you his plan?" said a man's voice.
"No," said another male voice.
"He didn't bring his wife and told everyone she was sick, so he could try and sleep with Ginny Potts. He wasn't expecting her to have a date since she was single when he saw her at the reunion a few weeks ago. He was gonna tell Ginny that he and Marisol separated, sleep with her and then tell her he got back together with his wife," the first male voice said.
"Dude she's dating Iron Man there's no way she wants to sleep with Brad," the second voice said.
"Tony Stark is the coolest guy ever. He went 12 for 12 with the Maxim cover girls and now he's banging one of the hottest girls from our school," said the first voice again.
"Damn," the second voice said and they left.
Tony returned to the dining room and he saw Brad on his way back to the table and he was seeing red. The fact that this Brad guy thought he could disrespect both Pepper and his wife just did not sit well with him.
"I heard about your plan," Tony said coming up behind him.
"I'm not sure what you're referring to," Brad said playing dumb.
"The part about you telling Pepper you and your wife separated to try and sleep with her," Tony said, forming an angry line with his lips.
"Oh you're judging me? How many women have you slept with?" Brad asked.
"What you think of me is irrelevant. I'm going to tell Pepper and that's a promise," Tony said as he walked away
"You want to make a little wager Stark?" Brad asked.
"On what?" Tony asked eyeing Brad suspiciously.
"You eat twelve sweet and spicy bacon wrapped jalapenos without taking anything to drink until you're finished?" Brad challenged.
"And if I can't?" Tony asked.
"I get to dance with Pepper at the wedding," Brad said.
Tony was seeing red again. He really wanted to punch this guy.
"And if I can do it you will disappear and leave Pepper alone for good," Tony threatened him.
"You're on," he said and they shook on it.
The two of them returned to the table and Pepper felt the tension.
"Is everything ok?" she asked Tony.
"Everything is fine honey. We just made a friendly wager," Tony said.
"What is it?"she asked.
"It's between men," Brad answered.
Tony ordered the sweet and spicy bacon wrapped jalapenos.
"Tony you can't handle spicy food. You don't even eat Pepper's," she urged.
"Well there's one Pepper I like to eat," he said with a wink at her and everyone at the table laughed.
"Seriously Tony, why are you doing this?" Pepper said.
"I never back down from a bet," Tony said, pressing his lips to hers gently.
"We're doing this," Brad said.
The waitress put their food down and Tony began to eat his rare steak and he was not very happy. He was almost finished when the jalapenos came out.
"Ok Stark let's see what you've got," Brad said as he slid the jalapenos in front of Tony.
Tony closed his eyes for a moment and picked up the first pepper and put it in his mouth. The heat hit him instantly. He chewed it quickly and swallowed. He wanted to get this over with as fast as possible. This was about Pepper's honor. He was four down and dying to have a drink but he had to finish. He wiped at his forehead that was sweating profusely.
"Tony this is silly. You're killing yourself for what? Some male betting ," Pepper said as she rubbed his back.
"Pepper you'll understand when I finish," Tony said, forcing himself to take two more putting himself at the halfway
Tony took down another one and he was really suffering. His whole mouth and throat were on fire.
He grabbed another two and his eyes started to water. He was in desperate need of water.
"Tony stop this," Pepper said.
"Pepper just let me do this," Tony said, getting agitated.
Tony ripped the stems off the last four and just ate them as quickly as he could and he was severely regretting it but it was over finally. Tony's nose and eyes were dripping and his lips were starting to swell.
"Pepper I don't feel so good," Tony said and he was sweating and shaking.
"I need to get him out of here," Pepper said as she got to her feet.
They got back to the room and Tony hit the bathroom immediately. Pepper rubbed his back supportively while he was waving her away.
"Please go. I don't want you to see this," he said waving her away.
Pepper respected his wishes and went down to the hotel store. She grabbed some electrolyte water and anti nausea and anti-diarrhea medicine. She was shaking her head the whole time. She couldn't believe Tony would do something so stupid out of jealousy. His ego and betting were getting out of control. She paid for the items and hurried back to the room. Tony was curled up on the bed in his underwear and his eyes were bloodshot and he was still sweating.
"I got you some meds and some electrolyte water," she said as she sat on the edge of the bed and brushed his hair back.
"That guys a dick," Tony moaned as he held his stomach.
"You sound jealous to me," Pepper said.
"Pepper I overheard some guys in the bathroom talking about Brad ok, so will you listen for a minute," he yelled.
"I'm sorry," she said.
Tony pulled himself up to face her.
"Brad told some guys that he wasn't expecting you to have a date since you were single at the reunion so he told the truth that his wife is sick, but if you showed up alone he was going to say that him and his wife separated and try and sleep with you and then after the wedding the next time you guys talked he was going to say they got back together," he said.
"After hearing that there was no way I was letting him win the bet. And for the record he challenged me" Tony said, rubbing her arm gently.
Pepper couldn't control the tears as they spilled out of her eyes.
"So he never wanted to date me, he just wanted to sleep with me. This is so humiliating. Who knows how many people know," she said as more tears continued to fall.
"Hey don't cry. The joke is on him because he never got you. You're here with me. I'm a complete ass and I got you to agree to let me accompany you so how lame does that make him look?," he said as he reached up and brushed away her tears with his thumb.
Pepper managed a smile.
"You're not a complete ass,"
Tony smiled.
"Look, my makeup is running. I just need a minute to clean myself up," she said as she went into the bathroom.
Tony pulled the blanket back for her on her side and he was going to sleep on top of the comforter.
Pepper came out in her pajamas and a cool rag for Tony's face.
"Come here," she said as she placed the cool rag on his forehead to wash away the sweat.
"That feels really nice. But I should be taking care of you," he said.
"You can do that when you're my assistant for a day," she teased him.
"Oh believe me I will be taking care of your every need," he said with a wink.
"You're so fresh,"
"At least I'm consistent," he teased.
"So I figured you could sleep under the covers and I could sleep on top, unless you want me to sleep on the chair I will, it wasn't that bad," Tony said motioning to her side of the bed.
"You don't have to sleep in the chair and you don't have to sleep on top of the blankets," Pepper said.
"Are you saying you want to sleep with me? Because it's not going to be that easy. At least buy me dinner first," he teased.
Pepper elbowed him playfully.
"Hey I'm fragile right now," he said holding his stomach.
"I'm sorry but in all seriousness Tony I can't believe you did this to yourself. You can't handle spicy food at all. All of that to one up Brad,"
"I didn't do that to one up Brad. I did it for your honor," he said pointing at her.
"I swear I could kiss you," she said.
Tony perked up suddenly.
Pepper grabbed his face and pressed her lips to his firmly and pulled them away quickly.
"Oh wow you're hot," she said reaching over him for the water bottle.
"Finally you admit it," he said, enjoying Pepper being on top of him while she guzzled water.
"Is that what you want to hear? You want me to tell you you're hot," she teased.
"Well I only ate 12 jalapenos for you, it would be nice," he said, taking the cool rag to his forehead again to play it up again.
"Your lips are very hot Mr. Stark," Pepper said with a smirk.
Tony just smirked at her. He decided when they got back from the wedding that he was going to confess to her how he felt.
"We should get some sleep. You need to feel better for tomorrow. Goodnight Tony," she said kissing his forehead and shutting off her bedside lamp.
"Goodnight Miss Potts," Tony said as he did the same.