Innocent Girlfriend

Note: this story involves cuckolding and humiliation.

Lucas and Riley had been dating since their freshman year of high school. Everybody who knew them thought they were the cutest couple, even if they were both a little conservative. They were model students who always followed the rules, played the lead roles in all the school plays, and graduated first and second in their class.

Lucas's best friend Chris was also popular and well-liked, but he was much more of the "jock" type. He was only average in his classes, but he was the star of the football team and ended up dating pretty much every girl in the cheerleading squad.

Chris ended up not going to college. Instead, he stayed in their small town and got an office job. Lucas and Riley, meanwhile, went off to the same university. They stayed together all through college, avoiding the drunken parties that the other students seemed to love. After their graduation, Lucas and Riley could both have gone off and made a ton of money doing whatever they wanted, but together they decided to return to their home town and start a charity organization to serve underprivileged people in their community.

Just before they graduated and moved back home, Lucas proposed to Riley. Of course, Riley said yes. They were both so excited to spend the rest of their lives together. They bought a small house in their home town and began making plans for their future.

Naturally, it wasn't long before Lucas reached out to his old buddy, Chris. Chris was happy to hear from Lucas, and they made plans for all three of them to get dinner together at a local restaurant. When they got to the restaurant, Chris gave each of them a big hug.

As they sat down, Riley began beaming and holding her hand out on the table. "So, Chris, do you notice anything new on my finger?" she asked with an excited laugh.

Chris saw the sparkling diamond ring that Riley was wearing. "Holy shit!" he exclaimed, then looked at Lucas. "You popped the question?"

Lucas grinned and put his arm around Riley. "Yep! We're officially engaged!"

"Congratulations!" Chris said, slapping him on the arm. "I'm so happy for the two of you!"

"Thanks, we're so excited," Riley said.

"How about you, buddy?" Lucas asked. "Finally settling down with anybody?"

Chris laughed. "Oh, no, not yet," he said. "I guess you could say I'm still playing the field, ya know?"

Lucas and Riley laughed. "Yep, sounds like the same Chris we knew in high school," Riley said.

"Hey, what can I say?" Chris said with a little bit of an arrogant swagger. "Some of us just aren't wired for that monogamous life, ya know?"

They laughed again. "How about Liam?" Lucas asked. Liam was Chris's little brother, two years younger than they were. "I thought I saw online that he got married a couple years ago?"

"Oh...yeah," Chris said, a little awkwardly. "Right out of high school. But actually, uh, that isn't going so well."

"Oh no!" Riley said. "What happened?"

"Well...they're talking about getting a divorce, unfortunately," Chris explained.

"Oh, no, that's terrible," Lucas said, surprised. "What happened?"

"Um, well, ya know...Liam's kind of embarrassed about it, but Jenny, his wife, ended up cheating on him."

"No!" Riley exclaimed.

"Yeah," Chris continued.

"Why would she do such a thing to Liam?" Riley asked, scandalized by this news.

Chris sighed. "From what they've told me, after they got married, Jenny started having second thoughts. Like, worrying that she might have settled down too quickly. I guess she started feeling like she was missing out on other experiences and stuff. So...she started, like, hitting on, um...another guy. And...ya know...one thing led to another."

"Oh, wow, that's...awful," Riley said, glancing over at Lucas.

"Yeah..." Lucas said. "I hope he's not too broken up about it. I'm sure once he's ready to move on, he'll find the right girl for him. We should all hang out sometime, keep his spirits up."

"Um...yeah, maybe, we'll see," Chris said, a little evasively. "He, uh, hasn't been too social with me lately."

"Oh," Riley said. "Well, he probably just needs some time alone."

"Yeah, something like that," Chris said.

"That's okay," Riley said. "Give him some space, I'm sure he'll be fine once he's had some time to process."

"Yeah," Lucas said. "And we'll be on the look-out for a girl we could match him up with. Ya know, when he's ready, of course."

"A good girl," Riley added.

Chris smiled. "Right," he said. "Although, it was pretty surprising, everybody had thought Jenny was a good girl."

"Yeah," Riley agreed. "I remember her from high school, she always seemed so sweet. I wonder what made her have all these crazy thoughts about settling down too fast."

"Well...obviously I'm no expert on relationships, but if you ask me my opinion," Chris began, "it was because she had never been with anybody but Liam, ya know? She never had those wild years that young people should have, when they're in their prime and they date different people. Like, she never had different experiences that would let her figure out what she really wants in a relationship. Like the two of you got to have in college, right?"

"Oh...um..." Lucas said, exchanging an awkward glance at Riley.

"Um...actually," Riley said, "Lucas and I stayed together the whole time in college."

Chris looked a little stunned. "Oh, shit," he said. "I'm sorry. I just assumed you had, like, the typical college experience where you take a break and play the field for a couple years, and then got back together."

"Um, nope," Lucas said, smiling at Riley. "We've only had eyes for each other this whole time, I guess."

"Wow, damn," Chris said, shaking his head a little. "And you two were together all through high school too. That's a long time for two attractive young people to spend just with each other."

"I guess so..." Riley said nervously.

"Shit, I'm sorry," Chris said. "I meant that as in, like, I'm impressed that you're both so committed to each other. I didn't mean everybody has to date around or whatever. I'm sure you two are, like...special."

Again, Lucas and Riley looked at each other awkwardly.

"Listen, forget I said anything. What do I know anyway?" Chris said apologetically.

Lucas forced a little laugh and waved his hand. "It's okay, don't worry about it," he said, taking Riley's hand in his. "We don't need to have dated other people to know we love each other, right, honey?"

"Right..." Riley said, but Lucas thought he heard a hint of doubt in her voice. He gave her hand a squeeze, but she didn't squeeze back.

***

After dinner, Riley and Lucas drove home in an uncomfortable silence. Lucas could tell that what Chris had said had gotten in Riley's head. He worried that she was starting to suspect that he was going to cheat on her or something. But that was ridiculous - Lucas truly felt completely satisfied with Riley. Through high school and college, he had never seen a more beautiful girl, and he had never even considered the idea of betraying her.

When they got home and got into bed, he turned to her and said, "Baby, I can tell something's on your mind. Are you still thinking about what Chris said at dinner?"

Riley bit her lower lip nervously. "Maybe a little," she admitted.

"Well, listen, honey," Lucas said. "Chris is a nice guy and everything, but he thinks about relationships in a totally different way than I do. It's never even crossed my mind that I haven't, like, experienced being with other girls or whatever. You make me so happy, and I love you so much, and I would never, ever think about being with somebody else."

Riley smiled and gave him a kiss. "You're so sweet, baby, thank you for saying that," she said. "I believe you, I'm definitely not worried about you cheating on me or anything."

"Oh," Lucas said. "Well, then, what is it? I can tell you're worried about something."

"Nothing really," Riley said, somewhat unconvincingly. "I guess it just made me think about how I've never even so much as gone on a date with a guy other than you."

"Oh..." Lucas said. Now he was the one concerned about Riley. "So, like...what are you saying? You think Chris is right? You want to...?" He couldn't even finish the sentence as his stomach sank at the thought of Riley dating other men.

Riley could see the look on Lucas's face and quickly reassured him. "No, no, no, baby, of course not," she said comfortingly. "It's not a big deal. It just made me think about things in a way I never had before. But you're right, we love each other so much, and we're perfect together, so there's nothing to worry about, right? Who cares if we haven't dated other people?"

"Yeah," Lucas agreed. "I don't feel like I've missed out on anything." He hesitated, then turned to her. "Do you?"

"...no, I guess not," Riley said softly.

But Lucas could see a look on her face that made him think she wasn't being completely honest. He didn't want to push her on it though, so he just told her that he loved her, and they went to bed.

***

A few days later, Lucas asked Chris if he wanted to get drinks at a local bar. He said sure, and the two of them met up that evening.

"How's Riley doing?" Chris asked as they drank a couple of beers.

"She's good," Lucas said. "She's just having some girl time with some of her friends."

"Hmm, cool," Chris said.

"Um," Lucas began awkwardly. "I think what you said the last time we hung out, when you were telling us about what happened with Liam, maybe got in her head a little bit..."

"Shit, man," Chris said. "I'm sorry I said that dumb shit. I need to learn to keep my mouth shut."

"No, no, it's okay," Lucas said, not wanting Chris to feel bad. "I mean, you were just telling us your opinion."

"Yeah, I know," Chris said. "I just didn't know my brother's relationship was so similar to yours."

"Well, I mean, they were a lot younger when they got engaged," Lucas said, a little defensively.

"True," Chris said.

"They probably just weren't right for each other, don't you think? And they rushed into it?" Lucas suggested.

"Maybe," Chris said with a little shrug. "I mean, I'll be honest, everybody who knew them thought they were absolutely perfect for each other. They had the same interests, the same sense of humor, all that stuff. I kinda wonder how things would've ended up if they had met a few years later, after Jenny had the chance to, like, be with other guys and stuff."

"What do you mean?" Lucas asked.

"I dunno, I just think if she'd, ya know, had her fun and gotten some things out of her system, and then met Liam and fell in love and all that stuff, it could've worked out," Chris said.

"Like, she wouldn't have cheated?" Lucas asked.

"Yeah, maybe," Chris said. "Because she wouldn't be wondering all the time about what other guys are like."

"Oh," Lucas said. There was an awkward pause. "...do you think Riley wonders about that?"

Chris sighed and looked guilty for saying the wrong thing again. "I'm sorry, dude, I didn't mean it like that," he said. "I mean, women aren't all the same, right? I'm sure that in her case, she's totally committed to you."

"Yeah..." Lucas said uncertainly. "I mean, she's always been so...innocent. I can't imagine her thinking about, like, other guys and stuff."

Chris shrugged. "Yeah, you're probably right," he said. "Although, I mean..." He trailed off. "Nah, nevermind."

"No, what is it?" Lucas asked, concerned at what Chris might be holding back.

"Well, I'm not trying to say you should be worried about Riley," Chris said. "I'm sure she's...different. But, like, Jenny was always super innocent too. Girls can definitely surprise you sometimes. But, like, yeah, I wouldn't worry about it or anything."

Chris's insistence that he shouldn't worry was only making Lucas more worried. Just then, his phone buzzed. It was a text from Riley.

"What's up?" Chris asked.

"Oh, nothing, it was just Riley saying she's gonna be a little late getting home tonight," Lucas said.

"Hmm," Chris said thoughtfully. "Everything okay?"

"Yeah, she just said she and the girls were having a good time, ya know, drinking and stuff," Lucas said.

Chris nodded. Lucas could tell he was holding back from saying something.

"What is it?" Lucas asked.

"No, nothing," Chris said.

"Dude, I can tell you're thinking something," Lucas insisted.

Chris laughed a little. "No, I'm sorry," he said. "I just, like, have a suspicious mind, I guess. Especially after seeing what Jenny did to my brother."

Lucas furrowed his brow. "What do you mean? You think Riley is...lying?"

Chris waved his hands. "Dude, no, seriously, forget I said anything," he said. "I'm sure she's really with her girlfriends."

"Yeah," Lucas said, suddenly concerned. "I mean, she wouldn't..."

"No, definitely not," Chris said. "And, like, relationships require trust, right?"

"Right," Lucas said.

"So forget it," Chris said. "Look, I said from the beginning, you shouldn't be listening to me anyway. I haven't been in a relationship that's lasted more than a couple months."

Lucas laughed nervously a little, but he was thinking about the possibility of Riley being with some other guy right now. "You're right," Lucas said. "You just had me worried for a second, ya know? Like...maybe what you said at dinner put some thoughts in her head and now she's...ya know..."

Lucas was hoping Chris would laugh off this suggestion, but instead he seemed to think about it seriously for a second and just said, "Hmm...yeah."

"I mean...you don't think that's what she's doing, do you?" Lucas asked.

"Nah, probably not," Chris said. "Like you said, she's a very innocent girl. I seriously doubt that she would immediately run out and just bang some other guy the first chance she gets, just because of one conversation, ya know?"

Lucas gulped nervously and tapped his fingers on the table. "I dunno...she has been acting kind of different, ever since our dinner."

"Oh...really?" Chris asked, sounding intrigued.

"Yeah, ya know, just acting like she's got a lot on her mind or something," Lucas said.

"Damn," Chris said. "Well, I dunno, dude. Don't stress about it too much, I guess? Kinda out of your control at this point."

"Yeah..." Lucas said.

Just then, Lucas got another text from Riley. It was a picture of her with her girlfriends, hanging out at one of their apartments. They all had drinks in their hands, and Riley looked red in the face. Riley captioned it: "we're having so much fun baby! so drunk though...we're playing never have I ever and of course I am losing every round!"

"Oh, phew," Lucas said, showing Chris the picture. "She really is with her friends."

"Oh, good, that's a relief," Chris said. Then he read the caption and said, "Hmm."

"What?" Lucas asked. "That's good, right?"

"I mean, yeah, it's good she's not with some other guy, obviously," Chris said. "But, ya know, you said she's had a lot on her mind, and now she's out with her girlfriends, hearing about all the experiences they've had and she hasn't..."

"Oh...shit, yeah," Lucas said.

"You know how those games are," Chris said. "They're probably talking about threesomes, and different sexual positions, and all the kinky stuff they've done, and the size of guys'...ya know..."

"Oh...fuck," Lucas said, thinking about how he and Riley only ever had regular, missionary-style sex, and that his penis was not very big. "What should I do?"

"I dunno, man," Chris said. "I mean, not much you can do, ya know? You're already engaged. At this point, ya just gotta roll the dice and see what happens, right?"

"I mean...I guess so..." Lucas said doubtfully. "Do you think she's gonna...ya know...end up cheating on me? Like Jenny did?"

Lucas expected Chris to reassure him, but instead he just kind of shrugged and said, "I mean...gotta wait and see, I guess. But, um, ya know...I'd keep a close eye on her if I were you."

"Shit," Lucas said, putting his head in his hands.

"Although..." Chris added thoughtfully. "If you're really getting worried...there is something you could try..."

"What do you mean?" Lucas asked.

Chris shook his head. "Nah, forget it, it's too weird," he said.

"No, no, what is it?" Lucas said, now panicked at the thought of Riley cheating on him.

"Well...it's kind of a crazy idea, but...what if, before you get married, you could, like...make an arrangement?" Chris said.

"An arrangement?" Lucas asked confused.

"Yeah, like, what if you talked to her about how you're worried, and you said, look, let's take a little break before we dive into the wedding planning? Just to give her some...time."

"Time? To do what?" Lucas asked.

Chris just raised his eyebrows, and Lucas realized what he meant.

"No, no way, I could never do that."

Chris shrugged. "Okay, man, I get it," he said. "I'm just saying...it might save your marriage in the long run."

"Shit...you really think so?" Lucas asked. He thought about it. It sounded crazy, but Chris did seem to know a lot about girls and how they thought. "I dunno, I just don't think I could handle knowing that she might be doing...whatever...with some random guy."

"Or guys," Chris said, and Lucas's face fell. Chris laughed a little. "Okay, I get it, that might not be such a great idea."

They sat in silence for a second, then Chris seemed to get an idea.

"Hang on...what if it wasn't some random guy? What if it was a guy you know and trust?"

"Jesus," Lucas said, rubbing his hands through his hair. "That still sounds so...weird."

"Yeah, you're probably right," Chris said. "I'm just thinking, ya know, that would be a safe way to let her explore, so that she doesn't get tempted into doing something even crazier, after you're married, like Jenny did to Liam."

"Fuck," Lucas said. "I dunno...maybe it's not such a bad idea."

Chris shrugged, letting Lucas think about his options.

"I dunno, man," Lucas said. "I always thought we were so perfect for each other. But I don't want her to think that being with me prevented her from, ya know, having all the experiences she wants and deserves."

"Hmm, yeah," Chris said. "You're such a good guy like that."

"But...I dunno...who could I trust for her to go on a date with?" Lucas asked.

"Yeah...you'd have to think carefully about that," Chris said. "Wouldn't want some asshole friend to take advantage of the situation, ya know?"

"Right," Lucas agreed. "Plus it would be so embarrassing to try to explain this to any of my friends."

Chris laughed a little. "Yeah, that's true, it is a pretty strange request. 'Excuse me, will you please take my girlfriend on a date and show her a good time for me?'"

Lucas sighed, almost giving up on the idea. Then he looked over at Chris and said, "Hey...what about you?"

"Me?" Chris asked. "Oh, nah, bro, I don't think so."

"Why not?" Lucas asked. "Dude, it would really help me out. You're one of my best friends, I totally trust you, and this way I wouldn't have to explain it to anybody else."

Chris thought about it. "Well, I mean, if you really think it would help," he said. "I guess I could do it."

"Please, dude?" Lucas said. "All you'd have to do is just, ya know, take her out to dinner and have a good time."

"Yeah, I mean, I guess I can do that," Chris said. "Just...normal first date stuff, right?"

"Right," Lucas said, then laughed. "You can even give her a kiss good night."

"Well, hey," Chris said, smiling. "I'm down for it if she is."

"Great," Lucas said. "And I bet that after a date or two, she'll realize she's not missing out on anything special and we can go back to normal, right? No offense, I'm sure you're plenty of fun on a date and everything, but I just mean, like, she'll see that what we have together is special, and she won't need to wonder about other guys anymore."