My Crush Dates a Jerk

"Yeah," I admitted. "I mean, it's pretty humiliating, but..."

"...but that's what you like about it?" Emily asked, smiling a little.

I felt myself turning red. "Yeah, I guess, kind of," I said.

"It's okay," Emily said, rubbing my arm. "So...is it okay if I go talk to Brad?"

I let out a sigh. "Um...yeah, okay," I said. "But, ya know...don't go sneaking off anywhere or anything."

She smiled. "Okay."

I watched as Emily walked over to where Brad was standing against a wall, drinking a beer.. She looked up at him with a smile, then noticed something on his arm. "Oh, is that a new tattoo, Brad?"

"Oh, uh, yeah," Brad said, smiling back at her. "You must have missed it last night. I got it a few weeks ago now, I guess."

"Cool!" Emily said. "Can I see it?"

"Sure," he replied.

I watched from across the room as he pulled his t-shirt sleeve up a little bit so Emily could see all of the tattoo he had gotten on his bicep.

"Oh, wow, I like it," Emily said, looking closely. She brought her hand up and touched it lightly with her fingers. "Sorry, do you mind?" she asked him.

"Not at all," Brad said, smiling a little. He brought his arm up to flex it.

She giggled, giving his bicep a light squeeze. "Oh my god, you're so vain. Always finding an excuse to show off your big muscles."

He grinned at her. "As I recall, you always liked these big muscles."

She laughed. In the living room, a group of people who had been occupying the couch and some chairs all got up to grab more drinks. "Oh, good, I've been wanting to sit down," she said.

"Me too," Brad said.

They both walked over to the now empty couch and sat down next to each other. Most people at the party weren't paying any attention, but I saw a few people glancing back and forth between them and me, covering their mouths to hide their laughter as I stood there. I felt myself turning red. While I was definitely still turned on, I was also getting kind of uncomfortable now. I decided I had to intervene in some way so that I didn't look like a complete loser. I walked over to them with my beer.

"Oh, hey, pretty boy," Brad said dismissively.

"Look at Brad's new tattoo, baby," Emily said to me, sliding his t-shirt sleeve up and lightly rubbing his arm.

Brad smirked at me as I stood there. "Uh, yeah, cool," I said.

Emily smiled, holding eye contact with me as she continued to touch Brad's arm. Finally, she slid his sleeve back down and took her hand away. I sat down in a nearby armchair.

Brad rested his arm on the back of the couch, above Emily's shoulders. He grinned confidently at me, making it clear that even though he wasn't touching Emily, this was still a territorial move.

One of Brad's lacrosse teammates came over with Madison. It was the same guy Madison had gone home with before. They sat down in a loveseat across the coffee table from me. "How's it going, y'all?" the guy said.

"Real good, Steve," Brad said. They smiled knowingly at each other.

"Hey, you missed a great party last night," Steve said to me. "Brad and your girl finally got to mend fences after their break-up, ya know?"

Everybody looked at me. "Um, yeah, Emily told me they ran into each other," I said. "That's great."

"Yeah, when I saw Brad show up, I thought things might get awkward," Madison said. "But they got along really well!" More suppressed laughter. "There's no hard feelings between you and Brad, are there, Emily?"

"Oh, no, that's all in the past," Emily said. "I mean, things were maybe a little awkward at first, but, ya know, we got past it."

"Yeah, we could tell," Steve said suggestively, laughing. Madison glanced over at me and elbowed him in the side, clearly thinking he was being too obvious.

Chloe and Jenny then came over with a couple other lacrosse guys. Chloe and the guy she was with pulled up a couple more chairs, while Jenny and the guy she was with just sat down on the floor. We all greeted them. There were now nine of us sitting around the coffee table in a circle.

"So is it weird seeing Emily here with Lucas, Brad?" Madison asked. Everybody laughed at Madison's bluntness.

"Nah, not really," Brad said. "It's cool. I guess I'm just not the jealous type, ya know?"

"That's sweet," Emily said. "So unlike you."

Everybody laughed. "Yeah, I mean, I guess I've always been kind of an asshole to you, huh?" Brad asked me.

"Um...maybe a little," I said awkwardly. Of course, it was easy for him to be nice to me now that he'd gotten a blowjob from my girlfriend the night before and was now sitting there with his arm around her shoulders.

"I actually feel really bad for that night I sent you that video. You remember that, right?" Brad asked.

There was a look in his eyes that let me know he didn't actually feel bad, he was just taunting me by bringing up this embarrassing incident from our past. "Oh, uh...yeah, I remember," I said softly.

"Wait, what did you do?" Chloe asked.

Brad grinned, acting like he was embarrassed, but then quickly launched into the whole story, clearly unconcerned that I might not want him to tell everybody about it. "Oh, well, there was this night when Emily and I were still together, and Emily got mad at me about some bullshit and ran off. And Lucas here thought she might dump me, so he could finally get his chance with her, ya know? So he keeps texting her and texting her, asking what was going on. But unfortunately for him...well, let's just say I found a way to persuade her to stay with me. And Lucas, I'm sorry, but your texts started getting really annoying. They were, uh, interrupting my flow, if you know what I mean. So I picked up Emily's phone and texted him that she was busy. And then I...well, I'm not proud of this, but I sent him a video showing him exactly what she was busy doing."

Everybody gasped and laughed. "You mean...?" Jenny asked, looking at Emily.

Emily just giggled and nodded.

"Like...going all the way?" Steve asked.

Brad laughed. "Oh yeah. He saw...everything. And, I mean, I don't want to brag, but she was really enjoying herself."

They all laughed some more, looking over at me. I started laughing too, trying not to look too embarrassed. At the same time, I felt my hard-on growing in my jeans. I didn't know why this was turning me on so much, but it definitely was.

"It was pretty cruel," Emily said, still giggling. She looked over at me. I felt myself blushing and looked down. "I'm sorry, honey, I know it wasn't funny at the time, but we can laugh about it now, right? I mean, you can't feel too bad, you ended up with me in the end!"

I forced a smile. "That's true," I said.

"Wow, that must have been hard to watch," Madison said. "You obviously had a huge crush on her, and there she is, with another man..."

"Uh, yeah," I said, discreetly putting my hands in front of my crotch in case my jeans started to tent up.

"You must have deleted that shit right away, huh?" Steve said.

I froze for a second, caught off guard by the question. "Oh, uh, well, ya know, I..." I stammered for a few seconds.

Everybody looked at each other in shock, then burst out laughing.

I quickly began protesting. "No, no, I did, I did delete it right away!" I lied.

"Yeah, right, sure you did!" Jenny said, laughing.

"Oh my god, dude, he probably jerked off to you fucking her!" the guy with Jenny said to Brad.

Brad looked at me. As everybody laughed, his arm casually moved down a little so that it was now around Emily's shoulders. "Dude, that's pretty fucked up," he said.

"I didn't do that, I swear!" I objected. I could tell nobody believed me. I looked at Emily, who of course knew all about my experiences with that video. She was just smiling slyly at me, glancing back and forth between me and Brad's hand on her shoulder.

I could now see a lot of people in the circle, and even other people at the party standing nearby, glancing over and noticing that Brad was pulling Emily closer to her in what was almost a cuddle. I was now incredibly turned on, but I also felt like this was going pretty far and it was time to put a stop to things. "Um...can you please take your arm off my girlfriend's shoulders?" I asked softly, trying and failing to sound assertive.

There was a little bit of a hush as everybody waited to see how Brad would react. "Dude, you're gonna make a big deal out of this, after what you saw in that video?" he said.

Everybody laughed. Brad kept his arm around Emily's shoulders, grinning confidently at me. "Very funny, but still, I think it's a little weird for your arm to be around her," I said. "You're not dating her anymore, remember?"

"Ooooh," some people said at this challenge.

Now Emily interjected, saying, "Baby, I really don't mind, it's just his arm touching me a little. It's not a big deal." She scooted a little closer to him as she said this. I could tell how badly she wanted to push this, but I could also see a questioning look on her face, like she was asking my permission. I felt like this was my moment to really decide if I wanted this to stop. I felt confident that if I objected again, Emily would get the message and stop, and we would go home. She might feel a little disappointed, but she'd be understanding about me not being comfortable with this.

Then I saw her smile as her eyes darted quickly down to my crotch, then back up at me, as if to say she knew what was hiding under my hands. My hard-on twitched, and I finally swallowed nervously and said, "Um...okay. I mean, I guess if you don't mind, it's not a big deal."

Brad smirked a little and moved his hand further down, his fingers lightly rubbing her upper chest. Everybody kind of took this in for a second, clearly entertained as Brad openly cuddled with my girlfriend, whom they all knew had cheated on me with Brad the night before.

"I have a great idea," Madison said suddenly. "We should play truth or dare!"

There was laughter and agreement from the others. I looked around in disbelief, knowing they were all going to try to push this even further. "I dunno, guys, we're not in middle school anymore," I said, trying to sound too cool to play.

"Aw, come on, sweetie, it'll be fun!" Emily said, still smiling slyly at me.

"Yeah, dude," Brad said. "Or, ya know, if you don't want to play, you can always head home and leave Emily here with me."

The crowd laughed. "Ha ha, yeah right," I said. Again, I now had a choice. If I insisted that I didn't want to play, I was again sure Emily would be disappointed but would go along with it and we would just leave. Or we could play, and see where things headed. "Okay, fine, I'll play," I said finally.

"Hey, everybody, if you wanna play truth or dare, gather around!" Madison called out to everybody at the party. A few more people quickly gathered around, sitting on the floor wherever there was space.

Madison called on Chloe to go first. Chloe asked for a dare, and Madison quickly dared her to make out with the guy she was with. Chloe laughed and quickly agreed. The two of them began making out as the crowd cheered them on.

A couple other people I didn't know took their turns next. A guy picked truth and got asked about the craziest thing he'd ever done sexually. He told a story about a sex party at his frat. A girl picked dare and had to flash her tits to everybody for ten seconds.

The sexual tension in the room was now obvious. I saw several people filing out the front door, clearly not interested in the direction things were headed. Plenty of others stuck around, though, eager to see where things went.

Next, it was Emily's turn. I felt my stomach tighten, as I knew this was going to get sexual. Emily smiled slyly at me and chose dare.

"I dare you to take that bra off," Brad said quickly.

"Oh my god, no!" Emily said, laughing and slapping Brad playfully on the chest. "This tank top is see-through."

"Exactly," Brad said, grinning. "Come on, rules are rules!"

The crowd cheered her on. She glanced over at me and smiled, then reached behind her to undo the strap of her bra. She pulled it out from under her tank top, held it for a second, then looked over at me and tossed it to me. "Can you hold onto that for me, honey?" she asked teasingly.

"Um...sure," I said softly as people laughed and cheered. I was taken aback, but I also felt myself pre-cumming into my underwear.

All the guys in the crowd were now staring lasciviously at Emily's perky tits through her white tank top. Her nipples were at full attention and poking through the fabric. Brad quickly put his arm back around her and pulled her closer to him, his fingers lightly playing with the strap and upper hem of the tank top. I saw some of the girls glancing over at me and giggling at my reaction as I sat there helplessly, staring and blushing.

"Okay, Brad's turn!" somebody called out.

"You know me," Brad said cockily, the tips of his fingers slipping just slightly under the top of Emily's tank top. "Always gonna go with a dare."

"Hmmmm," Steve said, glancing over at me. "I dare you to...give your ex-girlfriend a kiss. Don't worry, Lucas, just a quick one for old time's sake, ya know, to prove there's no hard feelings between them?"

I swallowed heavily, and felt like I had to object again. "Come on, guys, that's going a little too far, don't you think?" I said.

"Um, sorry, it's not your turn, Lucas, you don't get a say," Chloe said, giggling.

Emily smiled and bit her lower lip. "I'm sorry, baby, but...it's just a game," she said. "Let's just not make it weird, okay?"

"Yeah, dude, just relax and let me make out with your girl a little bit," Brad said, then quickly pulled the back of Emily's head toward his and slid his tongue in her mouth. The crowd cheered. They began making out, gently kissing at first, then Emily let out a little moan and rubbed his muscular chest while he slid his other arm around her waist. It felt like this lasted for a full minute, the crowd watching and the sexual tension in the room growing.

I was completely humiliated that my girlfriend was doing this right in front of everybody, but I also felt like if I gave my dick the slightest rub I'd be shooting my load into my pants. The two of them just looked so hot together.

Finally they parted lips. Emily was blushing a little, but had a big smile on her face and seemed to be catching her breath. Brad looked around and high-fived a couple of the guys around him, then looked over at me. "See, no big deal, right?" he said tauntingly.

"That was a little more than just a quick kiss," I grumbled.

The game continued, with people being dared to take off items of clothing or let somebody squeeze their tits or rub their crotches or take a body shot off somebody. The less adventurous players chose "truth" and got asked highly sexual questions. The atmosphere was extremely charged by this point. Couples were moving close together and cuddling or lightly rubbing each other. Of course, I continued to sit in my chair by myself, only able to look across the coffee table at my girlfriend cuddling with her ex-boyfriend.

Eventually it was my turn. I worried that if I chose a dare, they would just send me out of the apartment or something so that I couldn't stop Brad and Emily from going even further. So I reluctantly said, "Truth, I guess."

"Okay...you didn't really delete the video Brad sent of him fucking Emily, did you?" Madison quickly asked me.

I sighed, realizing I should have expected this. I looked over at Emily, who was smiling slyly. "Be honest, baby," she said teasingly. I felt a queasy mix of embarrassment and arousal, wondering why I was getting turned on at being made to admit this in front of everybody. I shyly looked around and blurted out, "No, I didn't...it's still on my phone."

People gasped and laughed. "Still?" Steve asked. "Even after you started dating her, you kept it?"

"Um...yeah," I said.

"So, like...it's just saved on your phone, or you actually watch it and, like...jerk off to it?" Jenny prodded, clearly amused.

"Um...isn't it supposed to be just one question and then it's somebody else's turn?" I objected.

People started laughing. "That means he jerks to it!" one guy said. "Come on, bro, just admit it."

I swallowed heavily, feeling my cheeks burning. "I mean, I...okay, yeah, I still...watch it sometimes."

Brad burst out laughing. I noticed his hand creeping further down Emily's chest. "Oh my god, dude, let me get this straight," he said. "You can fuck this girl whenever you want, but instead you stroke it to a video of me giving it to her?"

Everybody stared at me expectantly, waiting for me to answer.

"...yeah, sometimes," I said.

"Why?" a guy asked, genuinely confused.

"I dunno," I said nervously. "Emily just...she looks really hot in it."

"Yeah, because she's enjoying herself so much more than when she's with you," Brad said.

The crowd laughed and Brad got some more high-fives. Emily herself even giggled a little, but then said sympathetically, "Come on, everybody, stop being mean to my boyfriend! Are you okay, honey?"

She looked me in the eyes and seemed to be sincerely trying to gauge whether this level of humiliation was going too far. I could tell she was turned on and wanted to keep going, but I also knew she didn't want to really hurt me. A part of me definitely felt like running out of the room, especially since my girlfriend coming to my defense only made things more embarrassing. But I also felt almost liberated admitting to everybody that I got turned on watching my girlfriend get fucked by another guy. More than anything, I remained insanely turned on and really wanted to see things go further. So, as casually as I could, I smiled and said, "Yeah, it's okay, honey. I mean, Brad kind of has a point there." I laughed awkwardly, now having basically agreed with Brad in front of everybody that he fucked my girlfriend better than me. "Anyway, it's just a game, right?"

People seemed a little amazed that I was being such a good sport about things, but I got a few cheers and a couple guys slapped me on the back good-naturedly, even as they shook their heads in disbelief at what I was saying. Meanwhile, Emily smiled, clearly aware now that I was fully invested in this going as far as she wanted to take it. She leaned in closer to Brad, pulling his hand down until it was over her right breast. He smiled at her and started lazily moving his finger in circles around her nipple. She then put her hand on his thigh, rubbing it gently.

Everybody saw this and glanced back and forth between them and me. I had no intention of telling them to stop, though, so I just swallowed nervously and said, "Um...whose turn is it?"

Some people laughed, some gaped in awe at my inaction. But nobody said anything, and the game continued. A few couples had now gone off to corners of the room to make out and were no longer playing, which made things go faster. Madison and Chloe and Jenny each had a turn, all of them accepting dares to strip off items of clothing. They all cuddled up against the lacrosse guys they were with, in various states of undress. Eventually, it came back around to Emily's turn.

"You certainly look comfortable over there," Madison said to her. Emily just smiled as Brad lightly flicked her nipple with the tip of his finger. Madison looked over at me and finally had to say something. "You're seeing this, right?" she asked me.

"Oh, uh...yeah..." I said. It seemed like it was now obvious to everybody that I didn't really object to what was happening, but I still felt like I was supposed to say something. "Uh, Brad, can you, like, maybe stop doing that, please?" I asked him.

People laughed at how weak and insincere I sounded.

"Honey, it's actually making me feel really good," Emily said. "Is it okay if he keeps going? I mean, you did just tell everybody you jerk off watching him do way more than this, so it's really no big deal, right?"