Olivia's School Project - Pt. 01

Olivia and I have been close friends for years. We are almost exactly the same age at 18, with just a month between us, and we attend the same school, which is just a short walk from where we live.

We were also both held back in school the same year we met. She was held back the year her parents went through a messy divorce and I was held back because I moved and had to transfer to a new school in the middle of the year. The new school was much further along, so I had to repeat the year. But I think going through that year together really helped us bond and grow closer.

Anyway, Olivia is great and our friendship is really solid. I think we both compliment each other well. She's exposed me to the world of art, and I exposed her to sports. We like a lot of the same shows and movies and we have a very similar sense of humor.

She can be a little naive and gullible sometimes, but she is fun, quick to laugh, and willing to do almost anything for her friends.

I will admit though, sometimes I worry about her gullibility getting her into trouble. I don't think she's a dummy, she does fine in school, but I've seen her believe the most ridiculous things that people tell her.

In fact, I often take advantage of her gullibility myself by joking and playing pranks on her - but that's just part of our friendship. However, I sometimes worry about others taking advantage of it in less playful ways.

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One day during our senior year of high school we were hanging out in Olivia's bedroom working on homework together when her Mom called her downstairs. "I'll be right back," she said. "I have to go see what she wants."

"No worries", I said.

After a few minutes, Olivia made her way back to the room. "Ugh, my Mom is making me pick up Jenny. I've only been driving for a month and she already has me running errands constantly. Sometimes I wish I didn't get my license." Olivia's Dad wasn't around anymore and she often did favors like this for her Mom.

"I shouldn't be long. Do you want to come with me or stay here?"

"I'll come with you, why not? Lets just hope you don't kill us with your terrible driving." I teased.

"I'm not that bad!" she argued, "I was good enough to get my license!"

"That's just because the guy giving the test thought you were hot."

"No it's not! Anyway, give me a few minutes, I've gotta change. We have to pick her up at an indoor pool and I don't want to stew in there waiting for her to finish swimming. It gets really hot and sweaty in there. Let me put on something more comfortable."

As she ducked into her walk-in closet and began undressing I couldn't help but notice that the door was left open - probably more than a foot or two.

As I glanced over, my immediate thought was 'Wow!' Olivia had taken off her clothes and was now standing there in her underwear, giving me an amazing peek at her ass.

I'd always thought she was attractive but I hadn't really looked at Olivia sexually, until then. After watching for a few moments, I couldn't help but wonder why I hadn't noticed how hot she is. She's got an amazing ass, toned legs, an incredible flat stomach, and her boobs are way bigger than I ever realized. It was especially surprising given her tiny frame.

Olivia often wears fairly loose-fitting tops because, she once told me, she used to be self conscious about being flat chested. But she was a late bloomer and I guess she just got used to wearing looser clothes because she never really changed the style as she got a little older.

I hadn't realized how big her boobs are until I caught a glimpse when she was undressing in the closet. I'm not an expert on bra sizes, but if I had to guess, it looks like she wears either a D or DD cup. Seeing them really surprised me - I couldn't believe I never noticed them before.

A pang of guilt and excitement coursed through me as I watched the scene play out, but I couldn't look away.

"Shit!" Olivia said, breaking Jake out of his trance.

"What's wrong?"

"I, uh...forgot the shirt I wanted to wear is still in there. Can you turn around for a few seconds? I'm already undressed." she said sheepishly.

"No problem," I said, looking down at my homework and pretending like I wasn't paying attention. "Go ahead."

Olivia opened the door and ran over to her dresser wearing nothing but a low-cut bra and a tiny pair of shorts that perfectly hugged her ass.

Little did she realize that there was a long mirror against the opposite wall, so even though I was facing away, I could still see her completely in the reflection. She dug through a drawer for her shirt without noticing the show she was giving me.

As I watched her, I felt a flutter in my stomach and couldn't take my eyes off her reflection in the mirror. I couldn't help but be amazed at how gorgeous she looked standing in front of the mirror, oblivious to my view. I could even somewhat make out her nipples through her bra.

She quickly returned to her closet and finished changing. When she returned she playfully chucked a pillow at my face and I couldn't help but laugh. "Let's go!" she said.

The drive there was a bit nerve-wracking. Although I had teased her earlier that she passed her driving test because her instructor thought she was hot, I actually meant it. She definitely needed more practice and probably shouldn't have been driving yet. I doubt I would have passed a driving test with her driving skills.

We arrived at the gym, got out of the car and entered the building to let Olivia's sister know we were there.

Jenny was only about ten months younger than us but the three of us had never really hung out much. Even though she was also 18, in my head she had always just been Olivia's little sister.

As we waited in the pool area for Jenny, I understood why Olivia changed out of her other outfit. It was muggy and hot in there and I wished I had worn something else too. I was about to tell Olivia that I would wait outside when Jenny swam up to the edge of the pool and got out.

I had never seen Jenny in anything so tight or revealing and I was stunned. She looked incredible.

"Holy shit!" I accidentally said under my breath, but still out loud, unable to avoid looking at her tits.

Olivia punched me in the arm "Watch it! That's my sister you're talking about! I know what you were looking at."

"Well it's kind of hard not to. How can she swim with those? I thought swimmers were usually supposed to be pretty flat chested?"

"Yeah, a lot of the really competitive swimmers are. She complains about them being too big for swimming, saying they're preventing her from winning in competitions. She might be right too. But still, at least she doesn't have to deal with mine - I could never competitively swim."

I took advantage of the conversation as an excuse to glance at her tits, something I'd never done in such a blatant manner before. "Hmm, I dunno, ya really think yours are bigger? I might have to disagree." I said jokingly, knowing full well that Olivia's were bigger.

"Are you kidding me? Mine are def..." she looked at my face and realized I was fucking around with her. She punched me in the shoulder again "Shut up. Oh and don't stare at my boobs!" She said playfully in mock protest.

That was probably the first time I ever made a comment about her boobs and it went smoother than I might have guessed. I was relieved that it didn't get weird or anything.

Jenny walked towards us with a towel wrapped around her shoulders. "Hey guys, how's it going? Thanks for coming to get me."

As she stood there, she took the towel off her shoulders and started to use it to dry herself off.

"Just give me about ten minutes. I just need to shower off and then I'll be right out," she said, but then she just stood there for a good 20-30 seconds while she dried herself off in front of us, making small talk.

I was mesmerized. Her tits were absolutely incredible - big, perfectly round, perky and straining against the thin material of her bathing suit. I could easily make out her nipples as they were poking through her suit, and I could even see her areolas a bit too. I stood there stunned, trying not to be caught staring.

As Jenny walked away, Olivia punched me in the arm again. "Enjoy the view?"

"I couldn't help it! I can't believe she's allowed to wear that here! You could practically see through it!"

"I know but they're standard school swimsuits." Olivia said. "But, if you ask me, I don't think she minds that they're thin. In fact, I bet she picked one that was too small so that it was stretched even thinner. She's definitely got a promiscuous side. She can't get away with that stuff at home, so she's more of a tease outside the house."

We waited for Jenny to get dressed and then we all drove home together. I received a couple of glances from Jenny that made me wonder if she had put on her little show on purpose.

On the way back, I noticed how late it was and told Olivia I would have to go home as soon as we reached her place. Gathering my belongings, I took off in a hurry. After that scene, I definitely wanted some time alone with my thoughts.

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A few days after our last hangout, I went back to Olivia's house. We were sitting in her room when she suddenly looked up at me and said, "Jake, I have a question but it's kind of embarrassing."

"What is it?" I asked, puzzled.

"Well, we're studying old Roman statues in my art class and we have a group project to do that's focused on the human body. We can't carve statues of course, but we're supposed to turn in some sort of artistic representation of different parts of the body. I got the penis."

"What? You got the penis?" I asked. "What does that mean?"

"We were all broken into groups, and everyone in each group was assigned a different body part. Mine is the penis. We decided our representation will be paintings, which I pushed for because I know how to paint. But now I have to paint a penis."

"Can't you just say dick instead of penis?" I asked. "Penis sounds so... medical."

"Fine," she sighed. "I need to paint a... dick."

"Ok, so what do you want from me?" I asked.

"Well, I mean... I was kind of hoping... I know what they look like and all, but not well enough to paint one," she replied, flustered.

"I need to see something to paint it. And I don't really want to look it up online. I doubt that searching for 'penis' will bring up anything other than porn, and my mom has access to my search history. I doubt she looks at it much, but I don't really know and I can't exactly ask her to find out. I really don't want to take a chance."

"Why don't you just tell her that it's for school?"

"Because she's never going to believe me, and even if she did, it's not a conversation I really want to have with her."

"Fine, so what do you want from me?"

"Well... do you think you could... pose for me?"

"Nude?!"

"Well, you don't have to be entirely nude. I just have to paint your... thing."

"You want to paint my dick?!"

"Um, yeah."

"Seriously?! Ugh... I don't know. Aren't there any other options?"

"Well, I thought if you said no, I could ask Andrew."

"Andrew?! Why the hell would you ask him?"

She looked down a bit embarrassed. "Well, I don't want to ask him, but he's clearly not shy and I didn't know who else I could ask if you said no."

Andrew was a friend of ours, but we weren't as nearly as close to him as we were to each other. He lived pretty close to us so we did wind up hanging out a fair bit and had a good enough time, but we weren't really close friends.

Andrew was always able to attract the ladies, which made me a bit jealous. I don't think he's better looking than I am, but he is taller and has a little more confidence in himself. Those two things definitely helped him with the girls.

I know Andrew is into Olivia, he's made comments to me about her looks plenty of times and I think they hooked up once. I never knew exactly what happened, but I heard some details from each of them separately.

It sounded like they were hanging out one evening and Andrew played up some kind of sob story about how a girl he was dating cheated on him. Apparently he talked Olivia into hooking up with him as a way of getting back at his girlfriend.

The whole girlfriend story was probably bullshit, I'm not sure, but it was not too surprising that he was able to talk her into something like that. Like I said, she'll do pretty much anything for her friends, and she's very gullible.

Based on what I heard from each of them, I don't think things went too far that evening, but I don't know for sure. I've always wondered how far he pushed things that day.

I doubt he would hesitate for a moment if she asked him to pose nude. I don't know why, but the idea bothered me.

"How long are we talking about here?" I asked her

"I don't really know? I've never painted a peni-"

"A dick." I interrupted.

"A dick. I've never painted a dick before."

Even though Olivia is attractive, I knew she hadn't really done too much with guys... neither had I with girls. We spent too much time together to not know.

But I really hated the idea of her seeing Andrew's dick. He was my friend, but I didn't really want her seeing him nude. I think part of me didn't really trust him with her - especially if nudity was involved.

The idea of showing her my dick made me a little nervous, but also kind of excited me. My mind was starting to wander and I was starting to think of how I could perhaps use this to my advantage. After a minute, an idea came to me.

"Fine, I'll help you, but I have one condition. If I'm going to be embarrassed and standing there nude in front of you, I'm not going to do it alone. If I'm taking off my pants, you have to take off your top while you paint me."

"What? Are you serious?!" She asked, looking shocked.

"Why should I be the only one embarrassed?"

She looked at me blankly for a moment with her mouth slightly open.

"Fine." She resigned. "You're right. It's only fair."

'Oh my god,' I thought. 'Was this conversation really happening? Did she just agree to show me her tits?' My stomach was going crazy with excitement.

"Okay, when do you want to do this?" I asked.

"Well, the assignment isn't due for a few weeks, but I don't really know if I'm going to be able to do this in one session or not, so I guess the sooner the better."

"This is going to be multiple sessions?!"

"I don't know Jake!"

"Fine, let's start now and just get on with it."

"Um... okay." She said shyly. "My Mom isn't home so I guess it's fine to start now. I'll go get my paint supplies."

I stood there waiting, nervous, and still in shock about what was going on. I hoped it didn't change things with our friendship, but I couldn't deny I was really excited.

Olivia returned a few minutes later with her easel and paints looking nervous.

"Okay, so what do I do? How do we get started?" I asked.

"Well, I guess we should find somewhere comfortable for you to sit. Since I don't know how long this is going to take, I don't want you standing up the whole time."

She grabbed a chair from her desk, placed it in the middle of the room, and returned to her easel.

I took my pants off, stood there in my boxers and a t-shirt and sat down.

"Okay, your turn." I said.

"Are you seriously going to make me do this?" she asked.

"I'm not making you do anything. This is a favor for you. But yeah, if I have to sit here embarrassed with my dick out, you should have to do something embarrassing too."

"Okay, fine," she said. "But you have to promise me that this stays between us. I don't want anyone else finding out about this."

"I promise," I said, relieved that she had agreed.

Olivia took a deep breath, she pulled her shirt over her head exposing her glorious round breasts with a thin bra. I couldn't quite see through it, but the cleavage alone was enough to start getting me excited.

I took off my boxers and I tried to cover myself a little. I felt a little embarrassed, but I was also getting excited with her standing there in her bra.

Olivia glanced down shyly at my semi hard dick, but only for a second. It was really starting to turn me on.

"Ok your turn." I said again as I sat down.

"My turn what?"

"Your bra!"

"My bra too?! I didn't agree to that! You said my top!"

"What? I'm sitting here completely exposed, and you thought it would be fair if you kept your bra on? Do I get to put my boxers back on?"

"Ugh! Fine!" She took another deep breath, turned around, then reached behind her back and unclasped her bra.

She wasn't facing me, but even seeing her bare breasts from the side was a huge turn on. I couldn't believe this was really happening!

She slowly turned back around and attempted to cover her breasts, but it wasn't much help. They were overflowing under her arm and were just too big to hide.

I was amazed by what I was seeing. She slowly dropped her arm, and her nipples and huge pink areolas came into view. I was dumbstruck. Her tits were so amazing. Despite having removed her bra, her boobs didn't drop at all. They were so perky. I just couldn't stop staring at them. My dick started to grow harder right away.

She tried to avoid making eye contact, shuffling things around, but once she was fully ready to paint, she looked over at my dick and blushed.

"Oh!" she said as she looked down at my dick. "It's.... hard."

"Yeah, sorry. To be honest, I'm not sure if I'm going to be able to do it any other way. Is it going to be an issue?"

"Well... I don't know. I don't think a hard penis, um, dick, is what they had in mind for this project."

"Uh... shit. I'm sorry. It's just, I'm not used to modeling, especially nude, and you look amazing, and..." I trailed off.

Olivia blushed and shyly looked down.

"Well, this is embarrassing," I said.

"No, it's not your fault, it's totally... normal, I guess. I just didn't think about it."

"I just... I'm not sure that there's any way to get it down," I explained. "Unless... well, I don't think that's an option."

"What?" she asked, her brow furrowed in confusion.

"Well, I mean, I don't think you're gonna like it."

"What?" she asked, her voice laced with concern.

"Well... I think, maybe it would go down if you, ya know, touched it a bit."

"What? Seriously?" she said, looking both flustered and surprised.

I worried that I had crossed a line and that she was mad. 'Shit, now she's just gonna end this and wind up getting Andrew to pose instead' I thought to myself.

She paused, clearly thinking about it. "Would that really help? Wouldn't that just make it worse?"

"Well, yeah at first, but then it should go down, if you make me cum."

She stared at my hard dick, clearly considering my suggestion.

"Well..." was all she said, but after a moment, she hesitantly started walking towards me, still staring at my dick.

With her eyes looking down as she was coming closer, I took the opportunity to get a better look at her boobs without her realizing I was staring. I wanted to touch them so badly. Holy shit, they were so amazing!

She stood about two feet away from me and stared at my erection. "Are you sure? This isn't gonna be weird?" she asked.

"I think we're way past that now," I replied, trying to keep my voice steady.

She stepped closer and reached out hesitantly, wrapping her soft hand around my achingly hard dick. Her touch was so soft and delicate.

Fuck, it felt incredible.

"Like this?" she asked, her voice shaking slightly.

"Yeah, but can you maybe stroke it a bit too?" I suggested.

She started to slowly stroke my dick and it felt so good I felt like I could cum almost right away. It took everything in me to hold it back - I really didn't want this to end so soon.