My Crush Dates a Jerk

"Mmm, yes, give it to me, Lucas," Emily said.

"Oh my god, Emily, you feel so good," I said.

"Keep going," she said encouragingly. "Um, try going a little faster."

"Oh, okay," I said. I started thrusting in and out of her more quickly.

"Mmm, mmhm, yeah, keep going," Emily said. She reached down to play with her clit a little as I fucked her.

"Yeah?" I said. "Does it feel good?"

"Mmhm," Emily said, nodding up at me and smiling. I saw her hand rubbing at her clit a little more insistently now.

I couldn't help it, but images flashed through my head of the look on Emily's face in the video Brad had sent me. She had been moaning and crying out like crazy as Brad fucked her, without touching herself at all. I could tell I wasn't provoking the same reaction in her now. At the same time, I felt my dick twitch a little as I thought about Brad's thick cock stretching Emily's tight pussy. I looked down at her perky tits as they bounced underneath me, then let out a groan. "Oh fuck, Emily...I'm close," I said.

"Oh," I heard Emily say in a little bit of a surprised, confused tone.

But it was too late. I couldn't hold back, and I thrust into her one last time and began shooting my load inside her. "Ohhhhhh," I groaned, then collapsed onto her body. After I caught my breath for a second, I realized I had cum inside her without a condom. "Shit, I'm sorry," I said.

She smiled at me sweetly and petted my sweaty hair. "It's okay, Lucas," she said. "I'm on birth control."

"Oh, okay," I said. "Um...was that okay?"

She smiled and nodded at me. "Yes, Lucas, it was really good. A little bit...quick. But I get it, it was our first time."

"Yeah...I'm sorry. I guess I got a little over-excited," I said, grinning sheepishly.

"Don't worry about it," she said. "We'll just have to keep practicing, huh?"

I smiled at her. "So, like...does that mean we're a couple?"

She smiled back. "Yes, dummy."

I laughed, then leaned down and kissed her. I had never been so happy.

***

After that, I was a little scared that Brad would kick my ass once he heard Emily and I had gotten together. But he kept his distance, even if he did occasionally text Emily crude things, like asking her if she was ready to hop back on his fat cock and stuff like that. She was always honest with me and showed me whenever he texted, saying she didn't want to feel like she was keeping his texts a secret...even the couple of times that he sent her pics of his massive hard-on. She always just ignored him, even if I did catch her biting her lower lip and staring longingly at the dick pics he sent.

Emily and I started spending almost all our time together. It was great. I got a little nervous when about a month into our relationship, I blurted out that I loved her. But she just smiled back at me, touched the side of my face gently with her hand, and immediately told me that she loved me too.

The one problem we had was that I felt a little inadequate sexually, especially having heard and seen exactly how much Emily loved the sex she had with Brad. My dick wasn't exactly small, but I knew it couldn't compare to Brad's, and I also knew I wasn't as big and strong and aggressive as he was.

Probably worse than that was that I definitely didn't last as long as Brad did. The weird thing about that was, this had never been a problem for me with the couple of other girls I'd had sex with before Emily. I'd always been able to last a pretty long time. But with Emily, it was different. Sure, she was hotter than any girl I'd been with before, but if I was being honest with myself, that wasn't the only factor. The bigger reason I couldn't last more than ten minutes is that I couldn't stop thinking about how good Brad had fucked her. Images from the video he had sent, or the sounds Emily had made when he fucked her at the party, or just my own imagined fantasies of the two of them together kept running through my mind when I had sex with her, and they inevitably made me cum too soon. Even when I was masturbating, I mostly re-watched the video Brad had sent.

I felt like something was really wrong with me, but Emily was always really comforting and didn't make a big deal out of it. I could tell she wasn't being satisfied in the same way she was with Brad, though, and I started to feel really guilty about it. I even started asking her what I could do better, but she didn't really know what to say.

One night, I decided to take a chance. We were having sex, and as I slid my hard-on inside her, I looked down at her and asked, "Um...how...how do you think Brad would be fucking you right now?"

She looked stunned at this question. "What?" she asked.

"It's okay," I said softly. "I know that he was...like...good at it. What would he be doing right now?"

"I...I don't know," she said.

I slid in and out of her slowly. "Would he be fucking you harder than this?" I asked, looking intensely into her eyes.

I saw her breathing get a little bit faster. "I...yes," she said.

"Yeah?" I asked, thrusting in and out of her a little faster. "He fucked you so hard, didn't he?"

"Oh..." Emily moaned a little. "...yes."

"What else?" I asked.

"Mmmm," she moaned again, getting more excited as she thought back on her sex with Brad. "You really want to know?" she asked.

"Yes," I said.

"He'd probably be calling me his desperate little slut," she said.

"Oh fuck," I said. "He was right, you were a desperate little slut for him, weren't you?"

"Ohhhh," Emily moaned, louder now. "Yes, I was such a good slut for him!"

"Yeah?" I asked. "You loved spreading your legs for him, didn't you?"

"Oh fuck yes," she moaned. "I loved feeling his big dick inside me!"

"Oh god," I groaned, struggling not to cum. "Close your eyes."

She did, and I knew she was immediately picturing Brad on top of her instead of me.

"That's it, it's okay," I said. "Think about how good Brad fucked you with his thick fucking cock."

"Oh god...oh my god," Emily moaned, and I could see she was getting close to an orgasm.

"Say his name," I said, fucking her harder now.

"Oh fuck yes...oh Brad! Oh my god, Brad! Fuck me hard with your perfect fucking cock, Brad!" she cried, then her body started trembling. "Ohhhhhhhhh yessssss!"

"Fuuuuuuuuuck," I groaned, and immediately began shooting my load inside her.

I rolled off of her and we both caught our breath. Then she looked over at me. She was blushing. "Um...what was that?" she asked.

I laughed a little. "I...I dunno," I said. "I just...thought it might help, I guess."

"Um...yeah...wow," she said. "That was pretty...intense."

"Yeah...definitely," I agreed.

"But you don't, like...feel bad?" she asked. "That I was thinking about my ex instead of you?"

"I mean, I guess I feel a little jealous," I said. "But, like...I also got off really hard."

She giggled. "Yeah, you definitely did. I don't think I've seen you cum that hard since the first time we had sex."

"Yeah," I said. "Does that, like...weird you out?"

"Um...no, it's okay," she said. "But...it would be weird to keep doing it like that...wouldn't it?"

"I...I guess so," I said. "I just want you to be happy, ya know?"

She smiled and leaned over to kiss me. "You're so sweet," she said. "I love you."

"I love you too," I said.

***

From that night on, we couldn't stop ourselves from bringing Brad up when we had sex. It felt a little messed up, but it turned both of us on so much. One night, I even pulled out her phone and showed her the dick pics that Brad had sent her.

"That's the dick you really want inside you, isn't it?" I asked her.

"Oh my god, yes, look at his amazing cock!" she cried out. "I wish I was riding that thing right now!"

"Yeah?" I asked. "You wanna bounce up and down on it like a good little slut?"

"Yes! Yes! Yessss!" she cried as she orgasmed.

Another night, I pulled out my own phone and played the video that Brad had sent me. "Oh my god, you saved this?" she asked, watching the video as I fucked her.

"Yes, baby," I admitted. "I...oh god...I jerked off to it as soon as he sent it to me."

"Oh fuck...you did?" she moaned, clearly turned on by this confession. "You sat at home and jerked yourself off watching Brad fuck my tight little pussy?"

"Oh god, yes," I said. "I still jerk off to it, baby, all the time."

"Oh my god, of course you do," she said, moaning and smiling at how helplessly turned on I was. "Look at him stretching me out, baby. Do you like that? I love his cock so fucking much, don't I? Do you like seeing me beg for it?"

"Oh god, yes, baby, you're so fucking desperate for it, you little slut," I groaned. She started cumming as I pumped my load into her.

***

Things continued like this for a few weeks. It was incredibly weird, but also super-intense. Sometimes I'd initiate sex with the firm intention of not bringing Brad up at all, but once we started getting into it, I would get too horny to resist, and Emily always responded strongly, getting so much more excited as soon as his name came up. This was kind of humiliating for me, and I think we both knew that the whole situation was a little unhealthy, but all of that was left unspoken. We both seemed to be enjoying it too much to say anything that might ruin it. And outside of the sex, our relationship just kept growing deeper and more loving. So we settled into a routine, and even though the sex was a little different, we both seemed really happy and satisfied in the relationship.

Then, one night, Emily and I were hanging out in my dorm room when we both got a text. Madison told us about a party she and Jenny and Chloe were going to and asked if we wanted to go.

"Oh, I dunno, Em," I said. "I've got a midterm on Monday I don't feel so great about. I was just planning on staying in and studying."

"Oh, okay," she said, clearly a little disappointed.

"But you should totally go," I said. "We've been spending so much time together, you haven't really had a girls night out in a while."

"That's true," she said. "You really don't mind?"

"Not at all," I said. "It'll probably help me to focus, honestly."

"Okay!" she said. "I'm gonna head back to my place to change and then meet up with the girls."

"Cool, have fun!" I said. We kissed goodbye, and she left.

I cracked open a textbook, settling in for a boring night of studying for my exam. About an hour later, I got a text from Emily. She sent a picture of her with her girlfriends. They were all smiling, holding red solo cups. Emily was wearing a black, strapless dress that looked incredible on her. With the picture, she messaged, "This party's so much fun! Wish you were here with me!"

I smiled and texted back, "Enjoy yourself! You look amazing!"

She texted back, "Yeah, I know...lots of guys have been hitting on me. But don't worry, I'm telling them all I'm taken!"

My dick stirred a little bit at this teasing. I texted back, "Good girl!"

I went back to studying. Then, about a half hour later, I got another text from Emily: "Omg baby, I have to tell you something, but don't freak out."

I immediately got worried, wondering what this could be about, so I quickly replied, "Ok, I won't...What happened?"

She replied: "It's really not a big deal, but I feel like I should tell you...Brad just showed up at this party."

I swallowed hard. She hadn't seen Brad since their break-up (other than the dick pics he'd sent). "Oh wow," I texted. "Has he talked to you?"

"No...but we made eye contact and he smiled at me," she replied.

I didn't know what to say. Finally, I just texted back, "Ok...thanks for letting me know." Then I paused for a few seconds before adding, "It's not a big deal if you want to say hi to him or whatever." After I hit send, I quickly put the phone down and tried to re-focus on my studying...but it was hard to ignore the hard-on that had sprung up in my pants.

A few minutes passed, and Emily texted again: "Ok so...I wasn't going to talk to him, but he came up to me to say hi...so we talked a little bit."

I felt my mouth go dry. "Ok...was it super weird?" I asked.

"Well...he asked if I was still with you," she said. "Obviously he had to be a jerk about it."

"No surprise there," I said. "What did he say?"

"He was like, 'you're not still dating that pretty boy loser, are you?'"

"Oh haha...sounds like him," I replied, trying to sound casual.

"So I told him yes, I am, and we're very happy together!" she texted.

"Haha, good," I replied. "I bet he didn't like that."

"He just rolled his eyes. But um...don't get mad..."

"Mad about what?" I asked.

"Well...the whole time, he was...looking down the front of my dress."

"Oh," I replied, my hard-on twitching. "Well, that's not surprising...but it's not a big deal, baby, of course I'm not mad."

"Ok good...I just wish now that I hadn't worn something so revealing..."

"It's okay, sweetie...you should be able to wear what you want without worrying about jerks like him."

"Thanks, baby...I guess I'm just worried that I gave him the wrong idea or something, because then he did something else..."

"Oh..." I said, getting a little worried now. "What do you mean?"

"Well...right before he left to go get a drink, he kind of...grabbed my ass," she said.

My hard-on strained against my jeans. "Oh...shit," I texted. "What an asshole."

"Yeah, I know," she replied. "I couldn't believe it. Other people saw it and everything."

"Wow...did you say anything?" I asked.

"I guess I kind of just laughed it off," she said. "Is that okay? I probably should've slapped him or something."

"No it's ok, I get it, you didn't want to make a scene," I replied.

"Are you mad?" she asked.

"No," I replied, then prodded a little. "...you didn't do anything to encourage him, right?"

"Not really," she said.

"Not really?" I asked.

"I mean, I was friendly with him and laughed at his jokes and stuff."

"Okay..." I said.

"And when he was leaning over me to look down the front of my dress, I didn't push him away or anything."

"Right..."

"But it's definitely not like I was flirting with him!"

"Ok...I get it," I said.

"You believe me, right?" she asked.

"Of course, honey," I said.

"Thanks, sweetie," she replied. "But...can I be honest?"

"Of course," I said. "You can tell me anything."

"The whole thing got me kind of...wet," she said.

"Oh...shit," I said.

"Is that...bad?" she asked.

"No...it's okay," I texted. "I mean, I know how attracted you are to him."

"...yeah," she replied. "I'm sorry baby. When he put his hand on my butt, it was just...a lot."

My hand couldn't help but rub my crotch through my jeans a little. I didn't know how to respond to this, so I just texted back, "...ok." She didn't reply for a few seconds, so I added, "So what's going on now?"

"Not much, I'm just having another drink and hanging out with Madison and Chloe while I text you," she said. "They found the whole exchange very entertaining, of course."

"Haha," I said. Something about the idea of them witnessing this whole thing turned me on even more. "So they saw when he...?" I asked.

"Slid his hand under my dress and squeezed my ass?" Emily replied. "...yep."

I let out a long sigh. She was clearly teasing me with this now, and it was definitely working. "Wait...it was under your dress?"

"Oh...yeah. I didn't mention that?"

"No, you left that out."

"Oops," she said. "He has some nerve, doesn't he?"

"Definitely," I said. "So...what did Madison and Chloe say?"

"Madison said it's a good thing you didn't end up coming out tonight. Chloe just keeps talking about how hot Brad's looking."

"Haha...wow, such good friends, huh?" I replied, trying to sound casual.

"Haha, I know, right?" Emily replied. "They're bad influences. But don't worry, they're just kidding around."

"I get it, it's okay," I said. "Is Brad still there?"

"Yeah, he's across the room, hanging out with his lacrosse friends. He keeps looking over at me."

"Of course he does," I said. "Are you looking back?"

"...sometimes."

"Are you still...wet?"

"Baby!"

"It's okay, just tell me."

"I mean...yeah...is that ok?"

"Sure," I said. "Just my girlfriend getting turned on and making eyes at her ex boyfriend while I'm not around. No big deal."

"Haha," she said. "Be honest...are you...hard?"

I swallowed hard and texted back, "Very."

"I thought so," she texted, then added, "But I shouldn't, like...do anything, right?"

"Like what?" I asked.

"I dunno, like...go flirt with him some more?"

"I thought you weren't flirting with him before," I said.

"Oh right," she said. "Well, Madison and Chloe both seem to disagree with me about that. I guess it depends on what you call flirting."

"Giving him a view straight down the front of your dress? Giggling at him after he gropes you?" I replied. "I dunno, probably qualifies."

"Hmm, yeah, I guess so..."

"And now you want to flirt with him some more? In front of all our friends?"

"Maybe..."

"Don't you think that might turn into something...more?"

"...maybe."

I forced myself to put the phone down. This was a crucial moment in our relationship, and I knew it. Slowly, I let out a long sigh and took my hand off my crotch, which I'd been rubbing the whole time we had this conversation. I told myself that I had to put a stop to this before it went too far. "I don't know, honey," I texted. "I'm sorry, but I'm not sure I could handle things getting real like that, ya know?"

"Oh...ok," she said.

"I mean, I'm definitely turned on right now, and I know you are too," I said. "But...this is just going too far, right?"

"Yeah, you're right," she agreed. "I know we play around talking about it, but yeah, actually doing something with him would be pretty extreme. I would never want to do anything that would really hurt you."

"Right," I said, breathing out slowly and trying to calm myself down and tell myself I was doing the right thing. "Thanks, Em. I love you."

"I love you too, baby," she replied.

The next fifteen minutes were excruciating as she stopped texting and my mind raced with the possibilities of what she might be doing at the party. I trusted her, of course, but I also knew how hard it was for her to resist Brad's advances. I could only hope that she was able to avoid him. But at the same time, my erection refused to go away, and a part of me was even hoping that she chose not to listen to me.

Finally, she texted again: "Ok so...he came up and talked to me again," she said.

"Shit. And...?"

"Don't freak out."

"Em, what happened??"

"He kind of pushed me up against a wall."

"What??"

"Just listen. He sort of grabbed my waist and pressed me up against the wall and whispered in my ear."

"Omg!! What did he say??"

"He said, 'I want to take you into the bathroom and get you on your knees so I can slide my fat cock down your throat.'"

"Jesus," I texted back.

"Yeah."

"In front of everybody?"

"They couldn't hear what he was saying, but yeah, they could see him grabbing me and pushing me against the wall and whispering something to me."

My hand found its way back to my crotch, rubbing my persistent hard-on. "Fuck...so...what did you do?"

"Don't worry...I thought about what you said and pushed him off me and walked away."

"Oh wow...good job, Em! I know you find him kind of hard to resist," I texted back.

"Thanks...but I do feel like you should know...my panties are completely soaked through right now."

"Oh...ok."

"Are you still hard?"

"Um...yeah."

"His body was pressed up against me and his hand was sliding up and down my body in front of everybody, baby."

"...fuck."

"That turns you on, doesn't it?"

"...yes."

"Of course it does. Every time we have sex you get off hearing me tell you how much I want his dick, don't you?"