Olivia's School Project - Pt. 02

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Olivia finds a substitute model

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This is part 2 of the Olivia series. You might want to start with part 1 for context.

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The next few weeks were amazing between Olivia and I. We already had spent a lot of time together before we started dating, but lately it seems we've barely been apart, outside of school.

While some things are pretty much the same as they were before we started dating, some things have changed that I was not really expecting.

What surprised me the most was that I started to notice subtle changes in Olivia's appearance. She stopped wearing some of the baggy clothes she normally wore. The pants she started wearing were lower cut on her hips, and tighter around her legs and butt. She wore a few low-cut shirts that were tighter and hugged her breasts and revealed some of her midriff that had always been covered before.

I assumed she must have started going through her sister's closet a bit because I didn't know her to own these types of clothes.

Maybe she was trying to look good for my sake, maybe she was being more competitive with Jenny, who Olivia said she thought had a crush on me. Or perhaps it was something else entirely, but for whatever the reason, she looked stunning.

I must admit I loved it. She looked hotter than ever. I'm not sure how much of this was due to her new clothing choices, or how much of it was simply that I was looking at her differently now, but either way, I couldn't believe how attractive I found her.

Whenever we hung out I felt like I was constantly distracted with thoughts of her body and fantasies of touching her and her touching me and taking things further than last time.

We had a couple of make out sessions over the weekend but things didn't go too far. There was plenty of kissing and touching but I think I got a little self-conscious and was a little hesitant to push things too quickly and risk pushing her away.

I know we had already gone further before, but then we had the pretense of the painting to help get the clothing off. I was looking forward to having another session so we would once again have that excuse to get naked and see where things went.

Another change I noticed lately is in myself. I started experiencing feelings of jealousy that I hadn't before.

One day during my lunch period, Olivia walked by. She had lunch at a different time than I do so she wasn't stopping to chat or anything, and I don't even think she saw me, but a couple of the guys sitting at my table saw her and were remarking how hot she was.

They didn't know we were dating, and probably didn't know I overheard them either, but there were a few comments about how gorgeous she looked, how amazing her tits were, and how badly they wanted to fuck her. Clearly I wasn't the only one that noticed how attractive she was looking lately.

Listening to the guys talk about Olivia was an odd experience for me. I felt a little protective and annoyed that they were checking her out with so much lust, and probably a little self conscious knowing that she could probably have her pick of anyone.

Yet somehow, I also kind of liked it. I felt confident in our relationship and I felt a little proud that someone they wanted so badly was with me and not them. Part of me felt like, they could look and lust over her all they wanted, but she was with me.

However, no matter how I thought about it, the protective and jealous side was certainly still significant. Olivia was always a bit too naive and gullible and it worried me before, but even more so now that we were dating.

I've played a hundred tricks on Olivia, just for fun, taking advantage of her gullibility. Usually it was innocent things like, once I convinced her that they officially renamed New York into Gotham City. Another time I convinced her that she should make me a sandwich because it was National Sandwich Day. Once I even convinced her, on April fool's day too, that I was moving with my family to Mongolia, and we were going to raise sheep in the mountains. It seemed like there was little she wouldn't believe.

It was all in good fun and we often laughed about it, but it worried me how easy it was. I was concerned that she was definitely susceptible to more nefarious intentions.

In fact, I recently overheard someone telling someone else about an incident with a girl in their lunch period. Apparently a few guys had noticed they could see pretty far down a girl's top so they kept convincing her to do things that would cause her to bend over, like they would repeatedly drop something near her and ask her to get it for them so they could get a better look down her shirt.

It was stupid, but it apparently worked. She just thought they were being goofy and wasn't aware they were taking good looks down her shirt at her tits every time she bent over.

From what I overheard, they all got quite an amazing view.

I don't know for sure who the story was about, but I know Olivia had lunch during that period, and it definitely sounds like something that she would have done. And based on the description of the girl and what I know Olivia was wearing that day, my assumption is that it was her.

And Olivia herself told me about another incident where she was lost in thought and accidentally walked into the guys locker room. She said didn't realize it until she saw several guys in various stages of undress, several of them completely naked.

She said one of the guys casually approached her, while fully nude, and said she looked lost and asked her if she needed any help. She explained that she meant to go into the girls locker room. She laughed about her mistake, but then she ended up chatting with him for a minute about how she's done similar things before, but just never into a locker room. Then she said she looked down and noticed his dick got hard while they were chatting. She said he apologized for it and told her it had a mind of its own sometimes, and then they both laughed about it.

She didn't really seem to think it was a big deal, which kind of surprised me. She said she was just embarrassed about being in the wrong locker room, and he was just embarrassed that his dick got hard 'for no reason'. But ultimately she thought the whole thing was just a funny accident.

Anyway the point is, some things have changed and while part of me loved that she was loosening up and was wearing more flattering and revealing clothes, I know others enjoyed the view too and I was a little concerned, warranted or not, that others might start trying to make a move on her.

But I would have to cross that bridge when I came to it. For now, I was just really enjoying things with Olivia.

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One Wednesday afternoon I got a text from Olivia asking me if I could come over to her place after school so we could finish her painting project. I had really been looking forward to it, but I had completely forgotten she had a deadline approaching.

"Shit, I don't think I can today. I'm feeling like crap. I have a killer headache and I think I need to go home and try to sleep." I explained to her, disappointed.

"Oh, ok." Was all she replied.

"Is that a problem? Can't we just do it tomorrow?"

"Well... it's due tomorrow."

Fuck! I was really looking forward to having another 'painting session' with her, but I really was in no shape for it. I occasionally got migraine headaches and they weren't something I could just ignore and push through.

"Shit, it's due tomorrow? I wish you had mentioned it sooner. Do you think you finish it on your own?"

"I don't know. I don't think so but I'm not sure. If we had made more progress I probably could. I've been a bit distracted lately and I just forgot about it. But don't worry about it, I'll figure something out."

"I'm really sorry." I said.

"That's ok. I hope you feel better!"

I was so pissed... I had so much fun the last two times and I really was looking forward to doing it again. But there was, unfortunately, nothing I could do about it.

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Friday rolled around and I decided to go over to Olivia's house after school. I didn't have any classes with her that day so I didn't see her at all during the school day.

When I got to my house after school, I dropped off my stuff and immediately headed to her house.

Jenny let me in when I arrived and she had a slight mischievous smile when she greeted me. I wasn't entirely sure how to react to it, so I just smiled back.

"Is Olivia home?"

"Yup, she's upstairs. You can go on up." she said, still smiling.

This was the first time I had seen her since she walked in on Olivia's and I and she saw my dick. It seemed a little awkward, at least to me - she seemed to be enjoying it, but I just ignored it and went directly up to Olivia's room.

"Hey Olivia." I said as I walked up and kissed her hello. That was one of the new changes I really liked. I now often kiss her hello.

"Can you believe it, Jenny just asked me out on a date!" I lied jokingly to her, "I guess you were right and she does have a crush on me!"

"She did what?!"

"She asked me out, tomorrow night. I felt bad for her, so I said yes. You don't mind, do you?"

"But I told her we're dating now! What the hell? Wait, you said yes!?"

"Yeah, I mean, how could I say no?"

"But..."

"Olivia, I'm screwing with you. Shit, you'll believe anything."

"You dick!"

"Actually, it felt a little awkward when she answered the door. I haven't seen her face to face since she walked in on us and saw my dick."

"It was awkward?"

"Yeah, well I dunno. She smiled at me like... I don't know. Like she knows what my dick looks like now, I guess."

"Don't worry about it. Besides, you saw her in that swimsuit at the pool so you know what her boobs look like too. I guess you're even."

"True, I won't argue with that."

"Wait, you won't argue with my point? Or with seeing her boobs."

"Both!" I said with a smile.

"You're such a dick!" She said laughing.

"You know I'm just teasing you. Oh but, speaking of dicks," I said with a chuckle, "how'd it go with your assignment?" I asked, curious how it turned out.

"Oh, it went fine."

"Really? Great! See, I knew you could finish it on your own. I wouldn't have minded helping you again though."

"Well, I mean, I did need more help. I tried, but I couldn't finish it on my own."

"Really? What do you mean? Who helped?" I asked, not really considering what was coming next.

"I called Andrew."

"Wait, what? What do you mean, for what?" I asked, panicking somewhat. I was worried I already knew the answer.

Andrew was a friend of ours, but I think it was largely because he lived so close to both of us. We hung out sometimes, but were never nearly as close to him as we were to each other.

He was a little bit of a player when it came to women. He wasn't too over the top or anything, but I didn't really trust him with Olivia. Not in a situation like this.

I knew Andrew was attracted to Olivia because he's told me on several occasions, but I think they also hooked up once before too.

"Well, I didn't know what else to do." she said looking a bit confused. "I couldn't finish it without help. I needed to turn it in yesterday and I didn't know who else to ask."

"Wait, did he pose nude for you?" I asked her, not knowing why. I already knew the obvious answer. But I was dreading her confirmation.

"Well... I mean, yeah. I... I didn't know who else to ask." she said slightly defensively. "He didn't really want to help. It seemed like it was a hassle for him, but eventually he agreed to help me out."

"What...?" I said, still a bit confused and stunned. "What happened? How did...?" I trailed off, not really even knowing what to say. My stomach was starting to knot up.

"I texted him on Wednesday after you said you couldn't help and I asked him if he'd do me a huge favor and pose for me for my project. At first he said he was busy and said no, but I went up to him after school to ask him again, in person. I kind of begged him. I had no idea who else to ask.

"I explained what happened with our earlier sessions. Well, I didn't mention the part about what happened with us, but I told him how I started the painting, with you as my model, but that you couldn't finish it. I told him I really needed someone else to pose for me and that was due the next day.

"I also explained that it involved nudity, and I didn't know who else to ask so he was my last hope.

"Once I explained that part, he changed his mind and said he'd help. I'm sure because he realized how hard it would be for me to get anyone else, especially with it being so last minute.

"I waited until after he said yes to explain the part about how you were hard during our sessions, and that I'd need him to be the same way so that I could finish the painting.

"I could see he was shocked when he realized what I was asking him to do. Since he was already hesitant I was sure he'd definitely say no after I told him that part, but he didn't! He immediately said it was no problem. I think he understood with the added issue of needing to be hard while he was posing, it was going to be even more difficult for me to find anyone else.

"It was really nice of him and I told him I'd owe him a huge favor. I was so relieved he said ok because I really had no idea what I was going to do if he said no.

"So he came over to my house after school, both my Mom and Jenny were fortunately not home. I brought him up to my bedroom, showed him where to sit and asked him to take his pants off. He definitely wasn't shy about it. He just pulled his pants down and his thing just fell out.

"I was kind of surprised when I noticed the size of it."

My face must have given away my discomfort because she quickly added:

"I mean, it wasn't like it was huge, but it was a little bigger than average and it was just thick.

"I felt a little self-conscious because I realized, when he took his pants off, at first I couldn't tear my eyes away from it. But I think I played it off pretty well though. I just acted like I was evaluating it for the painting.

"I reminded him that I'd need him to get hard. I explained again that I didn't have time to start from scratch because it took so much time just to get as far as I did, so I asked him if he could try to get it up."

As Olivia continued, I couldn't believe what I was hearing. My stomach was in knots, but I just tried to keep my cool and listen.

"Ok, so then what happened?"

"Well, at first he started rubbing his dick a bit, but it didn't help too much. It got a little thicker, but it didn't really get hard. He was staring at my boobs while he was touching himself, which I thought would help to get him hard, but it didn't.

"But then he told me it would probably help him to get hard faster if I took off my shirt. I wasn't initially a little hesitant, but I had already told him what happened when I painted you, and I accidentally mentioned how I had my top off then, so he knew I did it before. I thought it would be rude to say no this time, and I really needed him to be hard to finish the painting, so I agreed to take my shirt off."

"Jesus." I mumbled. I was torn about my feelings about this. It made me incredibly jealous, but I was also getting a little turned on hearing about it and I wasn't sure why.

"So I took my shirt off, and I was standing there in my bra. It felt a little awkward at first because he was still playing with his dick and looking at my boobs. Also, I realized after I took off my shirt that my bra was kind of see-through, so he could see my nipples a bit too.

"I hoped that would be enough to get him hard, but it wasn't. He told me he always thought my boobs were amazing, but that it probably wouldn't be enough to get him hard with my bra on, and said I might have to take it off if I wanted him to get hard.

"I didn't know if I should, but I looked down at my boobs and I noticed that, in addition to my bra being a bit sheer, it slid down a bit and the top of my nipples were already showing a little.

"Also, I know that he's been with a lot of girls so it made sense that he'd need to see more than boobs in a bra to get hard, so I decided to just take my bra off.

"I unclasped my bra and slid it off. I instinctively covered myself at first, but I realized it would defeat the purpose so I slowly dropped my arms, revealing my boobs. I felt really self conscious, but at least he was naked too.

"He really seemed to like my boobs. When I took my bra off, he told me how incredible they were and asked if maybe he could touch them a little."

"He tried touching you?!"

"Well, yeah. I mean, he asked. He said it would help him to get hard, so I let him."

"Of course he did." I grumbled under my breath.

"So he started caressing my breasts with both hands, and rubbed his fingers around my nipples. It felt so good my nipples started getting a little hard. I was a bit embarrassed because he was the one who was supposed to get turned on, but it was kind of obvious that I was the one getting aroused.

"He kept saying stuff like how amazing my tits are and how he loves my big areolas. With all of his compliments and with him continuing to play with my boobs, it definitely turned me on even more.

"I looked down at his dick and saw that it started to get more firm, but it still wasn't really getting hard. I told him I didn't think it was hard enough to paint because it needed to be fully hard so it matched yours.

"Then he asked me if he could try licking my tits a little because he said it might help. I was worried that you might not want another guy licking my boobs, but I didn't really know what to do. I really needed to finish my assignment and he was doing me a favor just being there, so I decided to let him do it a little. I figured, if it helped me finish my project then it would be worth it.

"He cupped my boobs in his hands then leaned down and ran his tongue around my areolas and my nipples. It felt incredible and my nipples started getting harder almost immediately. Then he started massaging my boobs while he was sucking on my nipples and then he lightly nibbled on them. It hurt a tiny bit, but it kind of turned me on too.

"But even after a few minutes of him licking them, he still wasn't fully erect. I mean, it was hard, but not like yours was. Yours was standing almost straight up. His looked mostly hard, but the angle wasn't the same, it was more at a downward angle, so I figured it needed to be harder to match yours.

"But at this point, I had no idea what to do. It seemed like he was enjoying it, but I was getting a little self conscious that I wasn't attractive enough to get him as hard as you were. And there was no way I would be able to finish my painting if he wasn't.

"Then he suggested maybe I should try touching his dick a little. I remembered that it helped to get you hard when I was painting you, plus, he had already been touching me, so I figured it wouldn't be a big deal if I touched him a little to see if it would help.

"I reached out and wrapped my hand around his dick. It was so thick that it turned me on even more. I've never touched one that thick before. I rubbed it a bit - it wasn't like I was jerking him off or anything though, I was just kind of slowly stroking it. It was so hot and smooth and..." she trailed off and didn't finish her sentence.

Jake noticed that as Olivia recounted the story, she seemed to forget he was even in the room. Her mind was clearly reliving the scene and she was getting turned on again as she recalled all of the details of their interaction.

"Rubbing his cock seemed to be helping so I kept going and started doing it harder and faster, and I even tried massaging his balls with my other hand to see if that would help.