Olivia And Jake Go To Prom

--------- Part 5 ---------

Olivia and Jake go to Prom

--------- Part 5 ---------

On a Friday, Jake walked home from school next to Olivia and felt the knots in his stomach. He knew it was time to say something, but his nerves were getting the best of him. It had been, what felt like ages, since Olivia had told him about what happened between her and Andrew and Ryan. She still didn't know that they had tricked her so they could fuck her, but she knew things had gone further than she should have allowed and she promised to make it up to him. But that was a while ago now and he couldn't help but wonder if she had forgotten.

Several weeks ago Jake had sex with Olivia's sister Jenny, and Olivia had intentionally set them up, so she had definitely paid Jake back partially. But she said that was making up for her earlier mishap with Andrew. They both knew she owed him more, after she let both Ryan and Andrew fuck her.

They were nearing the end of their time in high school and Jake had a feeling, if anything was going to happen it would need to happen soon. They still weren't sure what would happen once they graduated and went off to college. He was pretty confident they'd stay together, but they weren't going to the same University and he knew a lot of change was coming.

While they were admittedly in love with each other, Jake also knew Olivia's naivety and her good looks were not likely to be a good combination in college. He worried about what kind of trouble she might get herself into with college guys, and didn't know for certain if their relationship could survive it. So as far as he was concerned, it felt like now or never.

"So... Olivia." Jake said.

"Yeah?"

"I wanted to ask you something that's a little awkward."

"What's that?" she asked.

"Well, remember how you said you wanted to make it up to me for what happened with you and Andrew and Ryan?"

"Yeah." She said hesitantly.

"Well, we never really talked more about that and I was just wondering about it. Were you serious about that?"

"Of course!" she replied, a little defensively.

"Ok." He paused. "Well, I was just wondering, did you have any thoughts about it?"

"Kinda. I've been thinking about it, and I haven't come up with anything much yet. But I thought" she hesitated before continuing, "maybe I could talk another girl into having a threesome with us. But I don't know who, and I was a bit nervous about how to actually go about asking someone.

"I thought again about Melissa Ault, but I don't really know her, so it would be awkward to be like, 'Hi, you don't know me, but I know you have a crush on my boyfriend, do you want to have a threesome with us?'"

"Yeah... fair enough." he said, disappointed. He really hoped something could happen with Melissa, but had no idea how to approach it either.

"I know another girl who I could maybe ask. Her name is Crysta. I don't think you know her though. She's about my height, but with short black hair. She's really spunky and I have a feeling she might be up for it. But I don't actually know if you'd even like her."

Jake felt a jolt of excitement in his stomach. He didn't know her, but the idea of a threesome definitely got him worked up. He hoped she was hot.

"No. I don't think I know her."

"So, would you be open to that?" she asked.

"Yeah! But, I can understand how difficult that'd be, actually asking her. It's not exactly something that could easily come up naturally."

They continued to walk for a minute or so in silence as neither of them really knew what to say.

"Can I be completely honest with you about something?" he asked her.

"Of course!"

"Well, I would definitely be interested in something like that, but I also wouldn't be opposed to... um... like, sharing you with another guy. But, not like last time with Andrew and Ryan. Things don't need to go that far.

"I know we've talked about this before, but for some reason, part of me does enjoy the idea of showing you off, a little. I want to be involved though, not just hearing about it later. I guess the point is, it doesn't necessarily have to be with a girl, as long as I'm involved."

"I might be OK with that, but I have a few questions.

"Do you have anyone in mind? How far would you want me to go with him? Like, fuck him? And last, well it's not so much of a question, but I think if it's a guy, I think you'd have to be the one to approach him."

"As far as how far you go... that's up to you. I mean I didn't expect you to fuck someone or anything like that. I guess it would mostly be a tease, showing off a little, maybe a little more, but we could play it by ear, then have amazing sex afterwards. But I definitely don't want you doing anything you don't want to do.

"As far as who, well, I might have one idea. But, I'm not sure how you'd feel about it. I'll explain the idea to you, and if you don't like it, it's totally fine.

"Ya remember how you keep catching Zach checking you out? Well, what about him? He's pretty shy, but he's nice, and I think if it's gonna be a guy, I think I'd prefer it to be someone like that. Someone that we can both feel confident and safe with. Pretty much the complete opposite of Andrew. I want us to be in full control of whatever we decide to do. Also, I would guess he's pretty inexperienced, and he wants you so bad, it would be fun to see his reactions as you tease him."

"Yeah, he's a little dorky, but kinda sweet. He's definitely not bad looking, just a little too shy. But yeah, he's clearly into me so that could work."

"I think the issue with that idea is" Jake continued, "I don't think he'd just willingly walk into something like that no matter how I approach him with it. I think he might think it's a trick or something."

"So, how would we do it?"

"I don't know."

They walked on in silence as they continued to think about things.

"Prom is coming up. Maybe we could work that into it somehow?" Olivia suggested.

"Hmm, that could work."

"There are only a couple of weeks of school between prom and graduation too so the timing would be perfect. It sounds like pretty much no one will be in school those last couple of weeks, so we might not have to see him again after Prom and it won't be awkward afterwards."

"True. But I don't know if he's going. I could ask him though. I have a class with him tomorrow. I would guess he doesn't have a date and I don't know if he'd go alone. But... maybe I could nudge him into it. Maybe I could mention I just got my license and ask if he's got a ride? I bet if I told him I'm going with you, and offered to drive him, he might go just to see you all dressed up. Especially if I play up how hot you're gonna look.

"But here's the other thing. I think he's too shy to do anything. We'd have to initiate it, and put him in a situation that he would never turn down.

"What if you tease him at prom a bit... get him a bit worked up, we invite him back to your place afterwards - wait... can we even go there? Will your Mom or sister be home that night?"

"My Mom will be out of town for work. My sister will help me get ready, but I can probably convince her to go to a friend's house to give us the place for the night."

"Awesome! So then maybe when we get there we play some cards or something, then we act like we're both pretty drunk and we put him in a situation where he thinks I'm not around, or maybe he thinks I'm passed out drunk, you can tease him some more and we just see what happens?"

"But you said you want to be involved -- how would that work?"

"Yeah, I do, but I think with him we'd probably have to start off slow, so maybe, I'll watch from upstairs at the beginning, to keep an eye on things. I can see downstairs from the hallway loft in your place and he won't know I'm watching. Otherwise, I don't know if it'd work. I think we'll have to kind of play it by ear. If I happened to walk in on you two, he might be freaked out. I'll have to make it clear that it's cool somehow, hopefully then we can just play it out and see where things go. What do you think?"

"I'm OK with it, but are you sure this is what you want?"

"My stomach is already in knots with excitement." Jake said with a smile.

---------

The day of Prom rolled around, Olivia was a little nervous, but Jake could barely contain his excitement.

The conversation with Zach worked perfectly. Jake was right that Zach had no date and that he wasn't planning on going at all. However, Zach started re-thinking his decision after his conversation with Jake about it.

Jake mentioned that he was going with Olivia. Zach didn't know they were dating but his attention was piqued when Jake mentioned he was going with her.

Jake told him how excited he was to see Olivia in her dress. He said it was so low cut that her boobs will be practically falling out of it. Zach knew he had to see it!

Jake had also mentioned he was driving so he could bring Zach, if he needed a ride. That really started changing Zach's plans.

The next day after their conversation Zach found Jake and told him he decided he's going stag and asked Jake if he could take him up on his offer for a ride.

Things fell into place perfectly.

--------

The day of the prom Jake picked up Olivia at her place and thought she looked stunning. She had agreed to wear a strapless dress that really showed off her cleavage and the dress she wore definitely lived up to that.

"Wow, Olivia you look incredible!" Jake said as he greeted her.

"Thanks." She blushed. "You don't think it's too much?"

"No way! You look amazing! Really!"

Olivia had never worn anything like it before and felt a little self conscious. She had definitely been dressing more provocatively than last year, but this was different.

"I feel like I'm just putting my boobs on display, like 'hey everyone, look at my boobs!' Oh and also, since this is strapless I was supposed to be wearing nipple covers, but they didn't fit me - my areolas are too big so they were pointless. I hope my boobs don't fall out of this dress because I have nothing else under it!"

"Don't worry... you look sexy as hell, and besides, a little slip might help with our plan for tonight." he said with a grin.

"I don't wanna flash anyone at the prom though!" She replied a bit embarrassed, but she at least felt better after Jake's compliment.

"So your sister is gone for the night, right?"

"Not yet. She helped me get ready, but she's leaving soon. She knows we want some alone time tonight, but of course she doesn't know anything more than that."

"Great." Jake could barely contain his excitement. "Ok let's go pick up Zach."

They pulled up to Zach's house and both got out of the car. Jake climbed the steps to Zach's front door while Olivia waited by the car.

"Hey Jake. Thanks for the ride." he said as he answered the door, but he barely glanced at Jake as he looked past him trying to get his first glimpse of Olivia in her dress.

He was barely able to hide his excitement at seeing Olivia.

"Hi Olivia! You look great!" he said, and did a poor job at hiding the attention he paid Olivia's cleavage. He quickly noticed that her tits looked like they could fall out of the top of her dress at any moment. He definitely didn't want to miss it, if that actually happened.

"Thanks Zach. You look nice too." Olivia replied as she pretended not to notice his eyes trying to steal glances of her tits.

Jake drove them to the venue and as the 3 of them walked into the main ballroom Jake invited Zach to join their table. Zach accepted the invite but Olivia and Jake quickly dropped off their stuff at the table before they left to walk around and say hello to some friends, leaving Zach behind.

Before long people started making their way to the dance floor and Jake and Olivia intended to do the same. However, they wanted to have a drink first. They brought a couple of flasks of rum to liven and loosen things up a bit, and to hopefully help with their plan for the night. Olivia kept both of them in her clutch so no one would notice. They headed to a dark corner and discreetly took a few sips.

"What do you think?" Olivia asked. "Do you think this is gonna work?"

"So far so good. You look fantastic and he's definitely noticed. In fact, Zach isn't the only one who has been drooling over you since we arrived. I've seen a few jaws hit the floor as you walked by. Not to mention my own."

Olivia just smiled and blushed in response.

They headed out to the dance floor and after a few minutes, Jake started getting a little concerned about their plan.

"He's mostly been just sitting at the table. We'll have to see if we can get him out to the dance floor, get him to loosen up a bit."

Jake caught Zach's eye and waved him over to join them. Zach declined though. Jake suspected he either wasn't good at dancing, or didn't want to be a 3rd wheel. Maybe both.

"He won't come over," Jake leaned in and said to Olivia. "Maybe you should go ask him. I bet he'll come over if you ask."

"Ok, I'll be right back."

"Wait, wait. Before you go over, what if you slide your top down just a tiny bit and expose the top of one of your areolas, just a little?"

"Jake! I'm not doing that!"

"Just a tiny bit! Just to tease him. I bet that would get him to come over!"

"Jake! This dress is already showing off half of my boobs. I know we are planning on taking it a bit further tonight, but other people might see."

"I thought you wanted to make it up to me?"

"I do, but..." She exhaled, exasperated, and paused. "Fine."

She casually slid down her top, exposing the top inch of her large right areola, but self consciously keeping a hand over her exposed nipple. "I can't believe I'm doing this."

Jake started getting excited watching her, and at the thought of this tease, and needed to shift his dick to avoid making a scene. He knew Zach was gonna love this!

"And maybe just lean over a little when you ask him. We've gotta get him excited and interested for the next part to work."

Her face said she wasn't comfortable with the idea, but she responded "I'll try, if it's not too obvious."

Olivia walked over feeling self conscious and trying to casually act like she was scratching her shoulder to cover her slightly exposed areola so others didn't see.

Zach was sitting down at a nearby table. As she approached him she leaned down and turned her head to the side to speak more directly into his ear, but it was providing him an opportunity to get a good look at her tits.

"Hey Zach," she said as she leaned down in front of him, "Why don't you come out and dance with us?"

Zach couldn't believe he could actually see part of her areola! He couldn't pry his eyes away - he just focused on her cleavage and exposed areola, his eyes wide.

"What?" He asked. "The music is too loud, I can barely hear you!" Zach said with his seat

fairly close to one of the speakers.

Olivia got closer to Zach, giving him an even better view. Olivia didn't realize it, but her dress slid down a bit as she leaned down, showing more than she intended. Her dress was now coming down to just above her nipple, exposing almost half of her areola. Zach's heart was racing.

"Why don't you come dance with us? We have flasks we can share if you want a drink." she said.

"Really? You have alcohol?" he said, finally prying his eyes up from her breasts. "That sounds great."

Olivia casually fixed her top as they walked across the dance floor towards Jake.

"Let's go over to the corner so no one sees the flask, then we'll come back out to the dance floor." she told him.

"Hey man, good to see you're joining us." Jake said as he greeted Zach.

"Yeah, well Olivia mentioned something about a flask."

"Here, you can have some of mine," Jake said, offering his flask to Zach. "I've got to drive back later anyway so I can't have it all."

"Thanks!" Zach said.

As the 3 of them stood in the corner and took turns sipping from the flasks, Zach took every chance he could to stare at Olivia's cleavage while he thought no one would notice. He was disappointed to see she fixed her nip slip, but was excited at least he got to see it.

"I'll be back." Jake said. "I've gotta find a bathroom."

A few minutes later Jake returned, but only Zach remained in their corner.

"Where's Olivia?" He asked Zach, but got no answer. He saw Zach in a daze starting out on the dance floor with his mouth slightly open.

Jake turned to see what Zach was looking at and felt his stomach flip, as if he missed a step walking down the stairs. Olivia was dancing on the dance floor with a guy Jake didn't know. While she was dancing with him, another guy, clearly his friend, was taking pictures of them dancing.

She seemed to be having fun, but he immediately noticed her boobs were spilling out of her dress and her right areola was clearly slipping out again, but this time she obviously wasn't aware. The guy she was dancing with, and his friend taking pictures, definitely did.

Jake felt the jealousy rise up inside, but was also somewhat turned on by the sight before him.

He knew their plan was for her to show off later tonight, and even more than she was currently, but something about watching it happen, and her not knowing about it, was turning him on.

For about a minute or so he went back and forth between watching Olivia, and watching Zach, and watching these two guys as they were all ogling his girlfriend. Then, as Olivia continued to dance, he noticed the continued jostling from the dancing caused one of her nipples to fully free itself.

The excitement grew from all of the guys watching her, Jake included. While it turned him on to see her unintentionally exposed, he didn't really like that he didn't have any control of the situation. After a moment, he decided they had seen enough and walked over.

"Hey Jake! She said as she stopped dancing and stepped aside to chat with him.

"Hope ya don't mind, I'm just having a quick dance." She leaned in closer to Jake to speak more privately to him, "Sorry, I don't really know him but he asked me for a dance. He said his date got sick so he came alone. I felt bad so I said yes."

"It's fine, but, uh..." Jake looked down at her chest "your nipple is out."

"Oh shit!" She said as she quickly pulled it up, embarrassed. "Do you think anyone noticed?"

"I don't know. Probably not." Jake lied as he saw Olivia blushing. He was certain the guy she was dancing with and the friend taking pictures were well aware, and he knew Zach noticed too. He didn't want her to be self conscious about it though, so he didn't tell her.

"Ok good! Well, I'm just gonna finish dancing this song and I'll be back over in a minute. I'll be more careful with my dress this time!"

Jake returned to Zach, and decided it was a good time to see if he could move things forward with their plan. With Zach getting a little peek of Olivia's nipple, he thought the timing was perfect.

"So what's your plan for later tonight?" Jake asked Zach.

"Nothing really."

"Well if you want, we're going to Olivia's house afterwards for some more drinks and maybe play some cards or something. It'll be low key, but you're welcome to join us if you want."

At that moment Olivia returned from the dance floor.

"Yeah, I don't really have any plans. I wasn't even sure if I'd come to prom at all, so some cards and drinks sound good.

"Your parent's don't care if you drink?" he asked Olivia.

"I only live with my Mom and my sister. My Mom is out of town and my sister is staying at a friend's house tonight, so we have the place to ourselves."

"Oh awesome! Sure, I guess I could join you. Oh... but I don't have any alcohol" he indicated to the flask.

"It's fine." She said, "I have plenty at my house."

"Ok great, thanks for the invite!"