My Crush Dates a Jerk

Brad hung out with us sometimes too, of course. But a lot of the time, he was busy with his classes or lacrosse or hanging out with his guy friends, so I got to spend a lot of time with Emily without him being around. I was grateful when he wasn't there, not just because I was so jealous of him, but because he was kind of a jerk to me, continuing to call me "pretty boy" and stuff like that. He clearly wasn't happy that Emily was friends with a guy, and I think he only tolerated it because he thought I was secretly gay.

But not only was he mean to me, he was also disrespectful to Emily a lot of the time. If Emily brought up something about poetry or art or things like that - the types of things I was happy to have a conversation with her about - Brad would quickly lose patience and change the subject to something else.

Sometimes it would get pretty insulting. Like one time, we were hanging out together with Madison and a couple of Brad's lacrosse friends, and Emily brought up that she wanted to be a famous writer one day.

"Pfft," Brad responded quickly. "Like that'll happen."

His lacrosse friends chuckled a little, but Emily looked hurt. "Well, it could," she said defensively.

"Yeah, I mean, you're a really talented writer," I said, trying to encourage her. She smiled sweetly at me, and I felt butterflies in my stomach.

"Come on," Brad said skeptically. "Don't you know how difficult it is to get a real, paying job as a writer? I'm just saying, the odds are stacked against you."

"Well, I mean, I know it's not easy," Emily said softly.

"Especially for a girl," Brad said. At this, Emily and Madison both gave him a glare. He just threw his hands up defensively and said, "Hey, I'm not saying it's a good thing, but that's the way the world is! Most successful women had to sleep their way to the top, it's just a fact."

The girls both rolled their eyes, and Emily said, "That's so sexist, Brad."

"Oh, okay, sorry, I guess I can't express my opinion," Brad said.

There was an awkward silence as Emily rolled her eyes again. "Well, I've read a lot of your writing for class, and I think you could really be successful at it," I said to her.

She smiled at me again, but Brad interjected. "Look, do what you want, Emily, I'm just saying, don't let the pretty boy here fill your head with a lot of pipe dreams. It's important to be practical and realistic in life."

"Thanks for the advice," she said to Brad sarcastically.

"Aww, she's so cute when she's mad, isn't she?" Brad said condescendingly, smirking at his lacrosse friends. "Don't worry, I know exactly how to make her feel better."

The other guys laughed. I expected Emily to tell him not to talk about her like that, but then she let him put his arm around her and a little smile crept across her face. I just looked away, disappointed she was letting him treat her like that.

***

The next day, I happened to run into Emily at a coffee shop and she invited me to sit with her.

"How's it going?" I asked her.

"Oh, it's good," Emily said. "I'm just kind of tired and have a lot of classwork to get done. I went over to Brad's yesterday and, well, he kept me up most of the night."

It was clear what she meant, and I couldn't help but remember the sound of her moans at the party. "Um...yeah," I said softly. "Well, I don't want to distract you or anything. Maybe I should get going."

"No, no, it's okay, stay, I could use a break," she said and smiled at me.

"Cool," I said, smiling back at her. "So have you been finding any time to do any of your writing?"

"Oh, um, yeah, a little," she said. "Thanks for being so encouraging yesterday when I brought that up."

"Oh, yeah, no problem. I was just being honest, you're really good," I said.

"Thanks," she said. "Although I guess I should just forget about it and be realistic and practical, huh?"

I waved my hand dismissively. "I know it's none of my business, but I really don't think he should talk to you like that. It's really disrespectful."

She sighed. "Yeah, I know. Brad can be a real jerk sometimes."

Hearing her say this sparked some hope in me. Maybe she was getting tired of what a dumb, arrogant jock he was and she'd dump him? "So, like, no offense, but...if he's such a jerk, why do you keep dating him?" I asked, hoping I wasn't being too obvious about wanting them to break up.

"Oh, ya know, he's got a lot of good qualities too," she said. "He likes to show off when his friends are around, but when it's just the two of us, he's a lot more fun."

"Oh," I said. "Yeah, I guess that makes sense."

"And, I mean, we just have...chemistry, ya know?" she said, then giggled a little. "Well, of course you know, you were at that party!"

I felt myself blushing. "Um, yeah," I said. "But, like, that makes up for him being such an asshole to you?"

She sighed again. "I know, it makes me sound totally superficial, doesn't it?"

"Oh, no, not at all," I said, not wanting to make her think I was insulting her.

"It's okay, I get it," she said. "I should probably dump him for all that bullshit he said yesterday, but he's just....I don't know. He's got a hold on me, ya know?"

"Oh," I said, disappointed. "Well, um, anyway..."

We changed the subject and had a great conversation, of course. Every time I made her laugh, I had to resist the urge to lean across the table and kiss her.

***

Emily and I started hanging out just the two of us more often, and our bond grew and deepened. But I continued to have to see her with Brad and watch how poorly he treated her. He was constantly disrespectful and dismissive toward her. He really didn't seem to value anything about her except her amazing body and cute face.

I could see Emily regularly getting annoyed or angry at him, and yet she continued to date him. Finally, I couldn't take it anymore. I decided that I needed to tell her how I felt about her, to let her know that she could be with a guy who respected and cared about her. So I invited her to have coffee with me, telling her I wanted to talk about something important.

"What is it?" she asked as we sat across from each other in a coffee shop.

"Well..." I began nervously. "I know you're with Brad, but I just wanted you to know...you can do a lot better than him."

"What do you mean?" she asked.

"Just...I...well..." I stammered, then finally blurted out, "I would treat you so much better than him."

"You?" Emily asked. "You mean you...?"

I felt myself turning red, but I knew I had to keep pushing forward. "Yes, Emily," I said. "I don't want to spoil our friendship or anything, but...I really like you. I...I want to be with you."

"Oh...wow," Emily said, then looked down.

I felt my heart sink, thinking I'd made a terrible mistake. "I...I'm sorry," I said, quickly backpedaling. "I shouldn't have said that."

"No, no, it's okay," Emily said quickly. "I'm glad you did. Actually, I...well, I have to admit, I kind of, um...I have feelings for you too."

My mouth fell open in shock. "You...you do?"

She smiled and nodded. "Yeah, I do. We get along so well, and you're really cute, and you do treat me a lot better than Brad."

"Wow," I said, unable to stop myself from grinning. "So...does that mean you're going to...?"

"Dump Brad?" she asked.

"Well...yeah," I said.

"I did have a serious talk with him recently," she said. "I kind of gave him an ultimatum. I said I wasn't going to put up with him treating me disrespectfully any more, and that if he didn't stop, we were through."

"Oh, wow," I said.

"Yeah," Emily said. "So, I mean, I'm sorry, but I'm not quite ready to break it off yet. I want to try to make it work with him if I can."

I nodded. "Sure, I can respect that," I said, feeling confident that there wasn't much chance of Brad changing.

"Um...thanks for being honest with me about your feelings," she said with a smile.

"Yeah...you too," I said, smiling back.

She got up to leave, and to my surprise, she leaned over and gave me a peck on the cheek.

***

That weekend, I went to another party with some friends, including Emily and Brad. Emily looked amazing in a tight, low-cut blue dress that stopped mid-thigh. Brad wasn't dressed up at all, wearing just a tank top and shorts, but that didn't stop Emily from clinging tightly to his muscular body the whole time. I felt a pang of jealousy, but I crossed my fingers, hoping that he'd say or do something obnoxious like he usually did, and Emily would dump him right there in front of everybody.

Sure enough, it didn't take long for Brad to start acting like an asshole. Emily was telling me and Jenny and Chloe that she had been writing a short story and was almost finished.

"Oh, that's great!" I said. "What's it about?"

"It's kind of a romance, I guess you'd call it," she said.

"Interesting," I said. "Well, I can't wait to read it."

"Yeah?" Emily said. "I'm a little nervous sharing it, but I would love some feedback."

Jenny and Chloe said they'd be happy to read it too and let her know what they thought. Emily thanked them, and then there was an awkward silence as she glanced over at Brad, clearly waiting for him to offer to read it as well.

Brad just kind of scoffed and said, "What, you want me to read it?" he said.

Emily smiled. "Well, I mean, yeah, you are my boyfriend. I'd love to know what you think."

"Uhhh," Brad said hesitantly. "I dunno, babe, I mean, romance isn't exactly my thing."

Emily narrowed her eyes. "Well, that's for sure."

"Aw, come on," Brad said. "I mean, I'm sure your girlfriends and the pretty boy will give you better advice than I could give anyway."

She sighed. "Still, it would be nice if you would read it. Can't you just do that, for me? It's not long or anything."

It couldn't have been more obvious that Emily was giving Brad a chance here to show he could change, but he just shrugged and said stubbornly, "Sorry, babe, it's just not my thing."

Emily looked a little stunned at this refusal, then slammed her drink down and said, "Fine." Then she stormed out, wiping tears away as she did.

We all stared at Brad as he stood there and watched Emily leave. He just rolled his eyes and said, "She'll get over it." Then he walked away to hang out with his lacrosse friends.

I felt bad for Emily, but at the same time, I was really excited that it looked like she was finally going to dump Brad. I stayed at the party for a while and hung out with friends, noticing that Brad left a little while later. Not long after that, a lot of my friends started heading home for the night, so I too headed back to my dorm.

When I got there, I texted Emily, asking if she was okay. She quickly texted back, telling me that she had had enough and that she was heading over to Brad's place right then to break up with him. I felt a little bad to be celebrating the failure of somebody else's relationship, but in all honesty, I was overjoyed.

I couldn't get to sleep, I was so excited. I kept waiting for a text from Emily confirming that she had dumped Brad, but a couple hours passed and I hadn't heard anything from her. It was almost 2 am by that point, but I couldn't resist texting her to ask how things had gone. A couple minutes passed with no response, but I could see that she had read the text, so I knew she wasn't sleeping. I told myself to just relax and talk to her the next day, but after tossing and turning for a few minutes, I couldn't hold back. I texted her again, saying I was sorry for texting so late but could she just let me know if she had gone through with it. Again, a couple minutes passed with no response, but again I could see that she had read the text. This was starting to get a little frustrating. I knew I should just put my phone away and go to sleep, but instead I texted again, saying that I could see she had read my texts and asking her to please just tell me what had happened.

A couple more minutes passed with no response, and I was just about to give up and try to go to sleep when my phone finally buzzed. It looked like it was from Emily, but it said "lol dude, stop texting, she's busy." My heart sank. Clearly this was Brad texting from her phone. But then it got even worse: he sent along a short video clip.

I let out a long sigh. I suspected I knew what was in the video, and a voice in my head urged me to not even watch it. But my thumb seemed to have a mind of its own and moved across my phone screen to press play. Emily immediately popped up, completely naked, lying on her back in Brad's bed and moaning in pleasure. Her round, firm, perky breasts were on full display, her perfect body glistening with sweat. Even though I was completely heartbroken, I also got an instant, rock-hard erection. Her body looked even better than I could have imagined. The camera then panned down a little, and I saw Brad's massive dick sliding into her. My jaw dropped. He was at least 8 inches and very thick, stretching out her tight, shaved, wet pussy.

"Yeah, that's it, that's what you fucking need, isn't it?" Brad said to her as he recorded himself slowly thrusting in and out of her.

"Oh god, yes, Brad! Please fuck me harder!" Emily moaned.

He laughed a little, then suddenly pulled out of her and held the tip of his cock at her opening. "Say you're sorry for walking out on me at the party," he demanded.

"Oh god, I'm sorry, Brad, I was being so stupid! Just please don't stop fucking me!" Emily begged.

"You're my little slut, aren't you?"

"Yes, Brad!"

"Say it."

She started squirming on the bed, desperately thrusting her hips toward his dick. "I'm your little slut, I'm addicted to your perfect fucking cock, please just put it back inside me and make me cum again!"

Brad laughed again and moved the phone so it was close up on his cock. He teased her opening a little with the tip, then swiftly slid inside her, making her cry out. The video quickly panned back up her body to show her face contorted in pleasure. She moaned louder as she approached an orgasm, then the video suddenly cut to black.

I felt completely ashamed and humiliated, but by the time the video stopped, my hand was already in my underwear and my fist was pumping up and down as I jerked off. I immediately pressed play to watch it again. "Oh my god, oh my god, oh fuck yeah, fuck her good with that big dick, such a fucking slut, oh fuuuuuuck," I groaned to myself as I watched, then shot a massive load all over my chest.

As I caught my breath, my head was spinning. The reality of the situation sank in. I could only lie there in bed and stare at the ceiling, shame and humiliation washing over me.

***

The next morning, I woke up with a raging erection. I looked over at my phone on the nightstand. Again, a voice in my head urged me not to, but my body was refusing to listen. I reached over and grabbed the phone, opening my texts and playing the clip Brad had sent me. I stroked myself and replayed the video three times until I shot another massive load.

Later that day, Emily texted me, saying she was so sorry that Brad had sent me that video. I felt so embarrassed. I told her not to feel bad, that it wasn't her fault. She asked if we could talk about what happened. I didn't really feel like dwelling on it, but I said okay, and we agreed to meet up on campus.

We sat at a table in a student lounge. Emily looked completely embarrassed and guilty. Even though I was hurt that she hadn't gone through with breaking up with Brad, I felt a little bad for her. "So...what happened?" I asked.

She sighed. "I don't know," she said. "I just...I went over to his place, and I was completely determined to dump him as soon as I saw him. But...when he answered the door, he was, like, shirtless, and just in his boxers, and..."

She looked at me, and I felt myself blushing, not really wanting to hear this.

"I'm so sorry," she said. "I just...I couldn't resist. I mean...did you, like...watch the video?

I sighed. "Um...yeah," I said softly.

"So you saw how much I...like him," she said guiltily.

"Uh...yeah," I said. "I get it. No further explanation needed."

"I'm sorry," she said. "I really can't believe he sent that to you. He's such a jerk. It must have been so upsetting to see that."

Of course I wasn't about to tell her I had jerked off to the video twice already. I forced a smile and said, "Uh...maybe let's just pretend like it never happened, ok?"

She smiled back at me. "Yeah, okay...hey, on the bright side, you got to see me naked!" She paused, then laughed a little. "Sorry, bad joke, huh?"

"Very," I said, but I laughed too.

"So...we can, like, stay friends, right?" she asked.

"Of course, Emily," I said. I was devastated, but I wasn't about to give up my friendship with her.

"Thanks, Lucas," she said. "You're the best."

***

I suffered through a couple more weeks of seeing Emily and Brad stick together, despite his continued disrespectful treatment of her. I couldn't believe it. I understood that she was obviously very physically attracted to him, but how good could the sex be for her to put up with such a jerk?

At the same time, I'm embarrassed to admit, I saved the video Brad had sent me and continued to watch and jerk off to it in my weaker moments, which were unfortunately pretty frequent. I always felt ashamed afterward, but it was such a turn-on to see Emily naked and moaning in such intense pleasure and begging so desperately to get fucked by Brad's big dick.

Finally, Brad really and truly crossed the line. One night, while I was in my dorm studying by myself, there was suddenly a knock on my door. When I opened it, I saw Emily, tears streaming down her face.

"Emily! What happened? Are you okay?" I asked, worried and ushering her inside.

"He...he...he cheated on me!" Emily cried.

"What?" I asked.

"Brad!" she said. "I walked in on him with another girl!"

"Oh, wow," I said. "I'm so sorry. What did you do?"

"I dumped him, of course!" she said. "This was the last straw, we're finally through!"

I felt terrible that Brad had hurt her so badly like this, but at the same time, my heart was leaping for joy. Finally, Emily was single!

I sat her down on the futon in my dorm and gave her a hug, allowing her to cry into my shoulder. "Hey, hey, it's okay," I said softly. "I know it hurts, but you're better off without him. You deserve way better."

Slowly, her crying subsided, and she pulled her head away from my shoulder. We looked each other deeply in the eyes, and her hand slid up to the side of my neck. My hand moved to her waist, and I gently pulled her closer to me. Our eyes closed, our lips met, and we kissed each other deeply. I couldn't believe this was finally happening!

We began making out, and eventually our hands started roaming over each other's bodies. I slid my hand under her shirt. She wasn't wearing a bra, and she let out a soft moan as I grasped her breast. Her hand slid down to my crotch and rubbed my 5-inch erection through my jeans. I was actually about to have sex with this incredibly hot girl I'd had a crush on for months!

We parted lips and smiled at each other. Emily pulled her shirt over her head. I could only stare in awe at her topless body. She giggled at my reaction, then pulled my shirt off. I leaned into her and began making out with her again as I lay her back on the futon. We each shuffled out of our pants and underwear until we were lying naked together. I kissed my way down her neck and chest, sucking eagerly on each of her amazing breasts, then kissed down her flat stomach and began eating her out.

I didn't really know what I was doing. I'd only had sex with a couple girls before. But Emily's moans encouraged me, and I was happy to see that she was getting wet as I licked her. "Oh god, Lucas," she moaned. "Please fuck me."

I didn't need to be told twice. I kissed my way back up her body, and she spread her legs for me. I lined my erection up against her opening and looked deeply into her eyes. She nodded at me, and I slid inside. It was the most amazing feeling in the world, so warm and tight and wet. I let out a groan and had to stay still for a few seconds to process the pleasure I was feeling. Then I began sliding in and out of her.