Disclaimer: this story involves cuckolding, humiliation, etc.
***
Lucas and Emily, both 21 years old, had been dating for about a month. While Lucas had had previous girlfriends, he’d never felt the way he felt about Emily. They’d met in class at their small liberal arts college, hit it off immediately, and gone on several dates. After a week or two, Emily invited Lucas back to her place, and they had amazing sex. Emily was beautiful – blond hair, short at only about 5’3″, thin but still a little curvy, perky tits that were a perfect handful, and a tight body from going to the gym on a regular basis. Lucas, meanwhile, was super-cute – also blond, only an inch or two taller than Emily, and a slim, smooth, toned gymnast’s body.
After a month of dating, Emily started feeling a little weird that she’d never been over to Lucas’s apartment, so she asked him if they could hang out there sometime. Lucas hesitantly agreed, but was quick to warn Emily that he lived with his older brother, Justin, who was 23 years old and could be kind of obnoxious. She laughed this off and asked what he meant. Lucas told her that Justin was arrogant and could be kind of a womanizer. Emily assured Lucas that she could handle him, so they agreed to hang out at his place that weekend and order a pizza.
Before Emily arrived, Lucas told his brother Justin to please try to be more respectful toward Emily than he’d been toward Lucas’s previous girlfriends. “She’s really special,” Lucas told him, “I’ve never felt this way about a girl before.” Justin said sure, of course, and seemed sincere.
Emily arrived a little while later, looking beautiful of course but not wearing anything special – just jeans and a t-shirt. “Hi, Emily,” Lucas said, “come on in. This is my brother, Justin.”
Justin, who was standing nearby, held his hand out, smiled, and said, “Hey, Emily, nice to meet you.”
“Nice to meet you too,” Emily said, shaking his hand. While she could see the resemblance between the two brothers, she was surprised at how much bigger Justin was – he towered above them both at over 6 feet, and he was much more muscular. They had the same sandy blond hair, but Justin had a bit of stubble, and his tight-fitting, v-neck shirt revealed light tufts of hair on his chest.
Emily and Lucas sat down on a couch in the living room, while Justin sat in a chair to the side. They made small talk for a while, Justin asking what Emily was studying in college, Emily learning that Justin had been working at a local law office as he prepared for law school the following fall. The pizza arrived, and they continued chatting.
“So do you have a girlfriend, Justin?” Emily asked. “Maybe we could go on a double date sometime or something?”
Justin chuckled a little. “Oh, ah, no, single at the moment,” he said. “I guess you could say I’m not really the monogamous type.”
“Oh,” Emily said, a little embarrassed, remembering that Lucas had told her Justin was a womanizer.
“Yeah, that’s why Lucas gets all the long-term girlfriends,” Justin said. “He’s always been the ‘sensitive’ brother.” He laughed a little, but then added, “No, really, he’s a sweet guy, you got lucky finding him.”
Lucas was impressed at how polite Justin was being, but still felt a little skeptical. “Uh, thanks,” he said softly.
“He is sweet,” Emily agreed, holding onto Lucas’s arm. “I can’t believe none of his previous girlfriends locked him down!”
“Heh, uh, yeah,” Lucas laughed uncomfortably, blushing a little. Emily noticed that he and Justin seemed to exchange a glance, and Justin cleared his throat a little awkwardly, seeming to stifle laughter.
There was a long pause, and Emily said, “Did I say something wrong?”
“Oh, no, not at all,” Justin assured her. He hesitated and then said, “So, uh, you haven’t told her, little bro?”
Lucas shot him a glance that Emily couldn’t ignore. “Told me what? I mean, I know about his previous girlfriends. He’s had three serious ones before me, right?”
“Yeah, that’s right…” Justin said.
“So…?” Emily said, confused.
Justin looked embarrassed. “Sorry, bro,” he told Lucas. “I just…you said before that Emily was special, and you’ve been dating for a month now, I just feel like you would want to let her know sooner than later…”
Lucas was turning bright red.
“What’s going on?” Emily asked. “Are you lying to me about something?”
“No!” Lucas objected.
“No, no, it’s not like that, Emily,” Justin said. “I’m sorry, I shouldn’t have even said anything. But no, he’s not lying, there’s just something he hasn’t told you quite yet, and it totally makes sense that he hasn’t, because it’s kind of embarrassing…”
“What is it?” Emily asked.
Lucas sighed. “Well, I was going to tell you soon, but I guess I have to do it now…” he said. “My other girlfriends, they all…well…they all cheated on me. That’s why those relationships ended.”
“Oh, sweetie,” Emily said. “That’s not so bad. It’s not even your fault!”
“I know, but…” Lucas continued. “…well, that’s not all…this is so embarrassing…”
“It’s ankara otele gelen escort okay, little bro,” Justin said comfortingly. “If Emily’s as special as you say, you owe her honesty, and she’ll understand.”
Lucas sighed and pressed forward. “Well, it’s not just that they all cheated on me, it’s that they all cheated on me with…Justin.”
Emily looked stunned. “What? Really?” she said, looking back and forth between the two of them.
“It’s not something I’m proud of,” Justin said. “I guess I just have a little bit of a problem resisting attractive girls who flirt with me.”
“Um…wow,” Emily said, absorbing this. “How are you two still cool with each other and living together?”
“Well, I mean, there’s definitely still some anger and resentment,” Lucas said, glaring at Justin for making him talk about all of this. “But, um, we worked through it, and, like Justin said, it was mostly the girls’ fault for coming onto him.”
“Oh…um…okay,” Emily said. “Well…I guess…I’m impressed that you can be so forgiving…and you clearly put family first.”
“Um, thanks,” Lucas said.
“And…I completely understand why you waited to tell me,” Emily assured him. “But thank you for being honest with me, that means a lot.”
Lucas and Emily looked at each other. She smiled warmly at him, and Lucas felt a wave of relief that this confession hadn’t made her think less of him.
The night went on and they had a great time, finishing the pizza and having a few drinks. Justin went to bed, wishing them both good night. Lucas and Emily went back to Lucas’s bedroom, stripped down to their underwear, and got into bed.
Emily put a hand on Lucas’s smooth, bare chest. “Well, that was fun,” she said. “You were so worried about your brother, but he seemed really nice to me!”
Lucas laughed. It was true, Justin had been on his best behavior. “Yeah, I guess maybe he’s maturing or something,” Lucas said.
“Mm,” Emily said. “I can’t believe he did that to you, though.”
“It’s okay,” Lucas said. “Those just, um, weren’t the right girls for me. Not like you.”
Emily smiled. “What were they like?” she asked curiously.
“Um, I mean, I should’ve known from the beginning that they would cheat,” Lucas said. “They were, ya know, the type of girls who always dress super-sexily and show off a lot of skin and go clubbing and stuff.”
“Sluts,” Emily said, and giggled. Lucas laughed. “But you and Justin are really still cool with each other?”
“Yeah,” Lucas said. “Like I said, we, um, figured out how to make it work. But it wasn’t always easy…he definitely has an arrogant streak.” He paused in thought. “And, um, after he…ya know…with my girlfriends, he always kind of acted…I dunno…victorious over me.”
“Oh, wow…um…” Emily said. She had to pause for a second, feeling suddenly aroused, then getting hit by a wave of guilt at being turned on by her boyfriend’s embarrassment. But she had to push forward: “I’m sorry if this is too personal, but I’m just really curious…”
“It’s okay,” Lucas said. “I want to be honest with you.”
“Well…how did you catch them?” she asked. Her hand had moved down to Lucas’s lightly toned abs, rubbing them with the tips of her fingers.
“Oh,” Lucas said, blushing a little. “I mean…each time, I just came home from school and…well…they were…ya know…I could hear them in Justin’s bedroom.”
“Oh my god,” Emily said softly. “That must have been so…humiliating.”
“Yeah, it was…” Lucas said, still blushing.
Emily’s hand slid down Lucas’s abs to discover that he had an erection. “Oh, my, looks like somebody’s awake,” she said, giggling a little.
“Oh my god, that’s so embarrassing,” Lucas said, sitting up a little, startled.
“Shhh, it’s okay, it’s okay,” Emily assured him, wrapping her hand around his hard cock and beginning to stroke.
“Mmmm,” Lucas moaned. “It’s not because of what we were talking about, it’s just, ya know, being in bed with you…”
“Shhhhh,” Emily said, then leaned in to kiss him. They began making out intensely. It didn’t take long before they had both stripped naked and Emily was straddling him, riding him to an intense orgasm before Lucas came inside her.
“That was amazing,” Lucas said. Emily could only sigh contentedly and collapse on top of him.
***
A few days later, Emily was out on a run in a nearby park, just as the sun was rising. She wore a pair of skin-tight running shorts and a sports bra, her hair tied back in a pony-tail. As she turned a corner on the trail she was on, she almost ran straight into Justin, who also happened to be on a run – sweaty, shirtless, and wearing just a pair of mesh gym shorts.
“Oh, hey!” Emily said, surprised, unable to avoid glancing up and down at his impressive body, which towered over her short, slim frame.
“Hey, Emily!” Justin said, also eyeing Emily up and down. “I didn’t know you were a runner. Although I guess I should’ve, with that body of yours.”
“Oh, öveçler escort thanks, ya know, I try to stay fit,” Emily said, a little awkwardly.
“I’m sorry, I shouldn’t have said that,” Justin said sheepishly. “I’m sure Lucas has told you I can go a little too far with stuff like that sometimes.”
“Oh, um, it’s okay, no big deal,” Emily said, shrugging it off. As she stood before Justin’s tall, sweaty body, she couldn’t help but notice that the light from the rising sun was coming up behind him and creating a clear silhouette of what could only be Justin’s extremely lengthy penis. She made a surprised little “oh!” sound and her eyes started darting all over the place, but seemed to keep returning to Justin’s crotch.
Justin noticed her reaction, looked down, and blushed. “Oh my god, I’m so sorry,” he said, trying to cover his crotch with his hands. “I just, it’s more comfortable for me, and usually nobody else is out this early, and…it’s not that obvious, is it?”
Emily couldn’t help but giggle. “No, it’s okay, I understand,” she said. She could still see the shadow of the tip of his penis through his shorts, extending below his hands.
Justin cleared his throat. “Um, my eyes are up here,” he said.
Now it was Emily’s turn to blush. “Oh my god, I’m sorry,” she said, laughing and putting her hands on her face.
Justin laughed too. “Don’t worry about it,” he said. Changing the subject, he casually moved his hands to his waist and said, “Oh, um, actually, it’s a good thing I ran into you, I wanted to get a chance to ask you about something while Lucas isn’t around.”
“Oh, what?” Emily asked. She couldn’t help but be a little concerned what this might be about, given Justin and Lucas’s history.
“Well, you know his birthday’s coming up, right?” Justin said.
“Oh, yeah, in a couple weeks, right?” she said.
“Yeah,” Justin said. “I was thinking, maybe we could throw a surprise party for him.”
“Oh!” Emily said, relieved that Justin’s request was so innocent. “Yeah, that’s a great idea!”
“Great,” Justin said. “So maybe we could exchange numbers so we can make plans?”
“Oh, yeah, of course,” Emily agreed.
“Cool,” Justin said. He pulled his phone from the armband tightly wrapped around his bicep. Emily’s eyes couldn’t help but take another peek at his crotch, and she had to gasp at the size of Justin’s penis. Justin opened his phone for her to type her number in and held it out to her, seeing that she was now staring and subconsciously biting her lower lip. “Um…Earth to Emily?” he said.
Emily looked up at Justin. “Oh my god, I can’t believe myself,” she said, laughing in embarrassment.
“It’s okay. I get it,” Justin said, smirking a little bit. Emily could now see the arrogant streak that Lucas had warned her about. She took the phone from Justin’s hand and typed in her number. “I’ll text you,” he said, putting his phone back. She could only stare as he started running in place for a second, his dick flopping around in his shorts, then took off past her.
***
That week, Emily and Justin texted back and forth about Lucas’s surprise party, figuring out a date and location and who would be keeping him busy and picking out supplies and decorations. Emily had been worried that Justin might have gotten the wrong idea from their encounter and start flirting with her, but he didn’t say anything that wasn’t related to the party-planning.
That weekend, Emily went to the mall to buy a new outfit for the party. Emily had never been a very flashy dresser, but ever since her conversation with Lucas about his previous girlfriends, she had started getting worried that she wasn’t dressing sexily enough. She knew that was kind of irrational, but she also just wanted to do something special for Lucas, so she decided to pick out some sexy outfit that would impress him.
The problem was, she wasn’t used to shopping for things that made her look sexy, and she didn’t really know what Lucas would like. She had asked some of her girlfriends to go shopping with her to help, but they had all been busy. She wandered around the mall aimlessly for a little while, then decided she had to reach out to Justin to see if he could help.
She texted Justin: “heyyy, I know this is a little weird, but I’m at the mall and want to get a ‘sexy’ outfit to wear for Lucas at the party, but I have no idea what I’m doing…do you know what kinds of things he would like?”
Justin texted back: “lol ppl don’t usually come to me for fashion advice but I guess I do have a sense of what little bro likes”
They continued:
Emily: omg thank god I’m desperate!
Justin: lol…soo I mean it’s not that complicated, he’s a dude after all, but I do know from his previous gfs that he likes bare midriffs and cleavage
Emily: *sigh* not really my style!
Justin: I know, and he definitely likes that you’re different from his previous gfs, so it’s not like you have to copy them!
Emily: yeah but I want to surprise him with something sexy! lemme look around for something…
Justin: pendik escort k
Emily browsed for a little while, trying to find something sexy that she was comfortable with. Finally, she came upon a low-cut white strap crop top. Two little white straps wrapped tightly around her sides, but otherwise her flat stomach was completely bare, and it showed off a little cleavage but not so much that she felt like a slut. She looked at her reflection in the dressing room, thinking that she looked good but not sure if she should buy it. She sighed, hesitated, then pulled out her phone and snapped a selfie. She hesitated again, then sent it to Justin, asking, “u think he would like this?” After a few seconds, she got three texts from him in a row: “oh wow”, then “u look amazing”, then “he also liked when his other gfs wore really short skirts btw”. She sighed, then texted back, “ok lemme look for that now”.
She bought the crop top, then moved on to another store to find a skirt. She found a black pleated miniskirt that was her size and tried it on. It only went about halfway down her thighs. She snapped a selfie and sent it to Justin, asking what he thought. He said it was perfect.
She still wasn’t sure, though. She turned around, worried it revealed too much. When she stood up straight, it was fine, but if she bent over a little, a tiny bit of the bottom of her butt was visible. She snapped a selfie, trying to get an angle that showed how short the skirt was. Then she paused, knowing that sending this to him might give Justin the wrong idea. But she had to admit that he’d been pretty much a perfect gentleman up to this point. She took a breath, then hit send, adding “too short?”. Justin texted back, “oh damn” and then “I mean, Lucas would love it”. She asked, “u sure?” and he said “definitely”. She smiled and texted, “ok I’m getting it! thank you so much for your help!”
As she was in line to buy the skirt, her phone buzzed again. It was Justin, saying, “I hope this isn’t going too far or anything, but I also know that Lucas used to pick out these cotton patterned thongs for his other girlfriends and he really liked them…” He sent along a couple links to some Victoria’s Secret underwear that fit his description. Emily gasped a little at her phone and texted back, “omg how do you know that?!” There was an unusually long pause before she got Justin’s reply: “they told me all about it when I was peeling them off”. As soon as she read that text, She felt guilty, but Emily felt her pussy getting wet at the mental image of Justin stripping Lucas’s girlfriends naked. “I guess I’ll have to take a quick trip to Victoria’s Secret then ;)” she texted, telling herself that this was still innocent enough.
As she perused the lingerie and underwear, her breath quickened and her heart started beating faster. She found a few different sets of patterned cotton thongs and bras and took them into the dressing room. Trying on each pair, they made her feel extremely sexy, and she snapped a selfie of herself in each one, making kissy faces and pressing her breasts together. She even took a pic of herself in a thong that didn’t have a matching bra, so that her perky tits were on display.
As her pussy got wetter, she opened her texts with Justin and pasted the pics. But as her thumb hovered over the “send” button, she hesitated and stopped herself. What was she thinking? She couldn’t possibly do this to Lucas. She quickly unpasted the selfies and took some deep breaths. But she still couldn’t resist sending something, so instead of the selfies, she took a few pics of just the thongs and bras, without her wearing them. “Like these?” she asked him. “Those are perfect, he’ll love them,” Justin replied.
—
Emily was proud of stopping herself from sending those selfies, but she still felt guilty that she had been so tempted. That night, she lay in bed with Lucas, and finally she had to turn to him. “I have to tell you something, baby,” she said.
“What is it?” Lucas asked, brushing hair from her face.
“Well…” she started, “I didn’t technically do anything wrong, but I would still feel bad keeping this from you…”
“Sweetie,” Lucas said, “you can tell me anything.”
“Well, I have to spoil a surprise for you then,” she said. “Justin and I have been planning a surprise birthday party for you.”
Lucas laughed. “Emily! Why would you tell me that?”
“Because otherwise you wouldn’t understand why I was texting with him,” she explained. She looked at his face, seeing that he was now growing concerned. Nervously, she picked up her phone. “We’ve been planning the party and stuff, and I went shopping today to pick out a sexy outfit to surprise you with, and…well…I texted him for his advice on what I should buy.”
“Well…that doesn’t sound so terrible, I guess,” Lucas said hesitantly.
“It isn’t,” Emily said. “But I just feel like you should read the conversation…”
“Okay…” Lucas said, taking her phone. He read for a couple minutes, whispering “damn” to himself softly at the pictures of her in the crop top and short skirt. Finally, he turned back to Emily’s nervous face and said, “Well, I mean, there’s nothing really so bad here. I wish my brother hadn’t said the thing about peeling thongs off my other girlfriends, but, ya know, you’re right, you didn’t really do anything wrong. And…you sincerely just wanted his advice, right?”