Chasing Summer Ch. 01

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I never knew I was a cuckold until Summer revealed her past.
3.3k words
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Part 1 of the 3 part series

Updated 06/08/2023
Created 12/27/2016
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We started dating back in high school.

We were the typical high school sweethearts in many ways, I suppose. We sat together at lunch, suffered through P.E together, and we both survived my senior prom.

Her prom was a different story altogether, but that's neither here nor there.

Summer Campbell was a couple of grades below me when we met, but we've managed to stick it out for the last few years, for better or for worse. It's been anything but easy. We've had our fair share of fights, explosive arguments, and otherwise toxic moments. We've gone through periods of distrust lined with shaky foundations.

Okay, so we're one of those couples that's broken up a few times and then gotten back together. So what? We love each other and that's the bottom line.

Truth is, Summer is the best thing that's ever happened to me, and I will always treasure the moment that she walked into my life.

I met her at a party - feels like so many years ago, now. My buddy Jason was throwing a little shindig at his place and he invited me over. I, being the social maestro that I am, ended up on my phone most of the night. I'd tried to strike up conversations with people at various points throughout the evening, but I just didn't know anyone there. Truth is, I've never been the kind of guy that can get dropped into a social scenario like that and, without knowing anybody, become the life of the party. Instead, it was quite the opposite. It was a pretty lonely night that left me feeling awkward and introverted for the most part.

For the most part being the operative part of that statement: that was all before Summer. Changing her transformed my night, and ultimately my life.

Jason, who had been one of my best mates for years, ended up introducing us. It feels like forever ago, and as clichéd and tired as it sounds, I can remember it like it was yesterday.

"Have you met Charles yet? Probably the smartest and dumbest guy you're likely to meet tonight at the same time," he chuckled, punching my arm.

That's when I saw her for the first time. She laughed and I swear she glistened. Her shimmering, golden blonde hair fell back over her shoulders and down her lovely toned back. She was fit, but not in a distracting or overbearing manner. Her tan frame looked like it was sculpted from a collage of supermodels. She must have been about 5'6, I'd say, and with hips like a...god damn, I'm not lying, she was the hottest chick in that room. She beamed a smile at me that would have intimidated the varsity quarterback. It was at that moment that I knew I was a goner.

"Oh really? And why's that?" she asked.

"Huh?" I snapped out of it, realizing that I was probably staring.

She giggled, seemingly recognizing this fact. "I was just asking your friend about you."

"The dude quotes Kant and eats differential equations for breakfast, but he's gonna bomb here like always," Jason laughed before slapping his buddy gently on the shoulder reassuringly. "Have fun, you two," he told them while making his way back over to the keg.

Okay, so my memory's not perfect. I can't remember the first thing I said to her, whatever dull line that might have been. Really, I'm not sure that I even remember the first thing that I ever heard her say. But I remember Jason's sarcastic introduction, because it lead to one of the best nights of my life. We talked for hours on end that night, just the two of us. We slipped away from the crowd, looked up at the stars, and I felt the blueness of her eyes intertwine with mine.

Sometimes I wish that night could have lasted forever.

Now, I know what you're thinking, but we didn't get together that night. She just wasn't that kind of girl. We were both young and didn't really know how to approach things back then. There wasn't even a goodnight kiss. It was just talking.

When I went home that evening I knew that I had met someone who was truly special. Even then, I'm not sure I would have anticipated how big a part of my life she would one day become.

About a month later I finally got the courage to ask her out and she said yes. The first kiss came about two months after that. I'll admit, it was a slow and arduous process. I'd had a few girlfriends up to this point, but none of them had been even remotely as...well, attractive, as Summer. That's not to say they weren't good looking, they were, and honestly I had felt lucky to be with them at the time. But Summer was a different level of hot. She was a different level than I was used to, so to speak. And to be perfectly honest, probably above the level that I had previously thought possible for me.

Moreover is the fact that I just wasn't that experienced. I had a dating history, but it was shallow, and I didn't have a good history of being bold in the intimacy department. Up to that point I had kissed a few girls and made out with others, but nothing more. And if I'm being perfectly honest, many of those instances were more a product of the situation or even the girl being a bit forward rather than my own persistence or initiative.

So yeah, the first kiss took a while. I'm not gonna lie, I was a little worried about Summer getting impatient with me. I explained to her that I wasn't that experienced, and she told me not to worry because neither was she. She was understanding and reassuring. What's more, turns out that she was a tad more bold than I. The first time I visited her she tackled me the moment we stepped into the bedroom and we started making out. Another time she lead my unsteady hands underneath her shirt to unhook her bra.

Several months later she took my virginity, and I took hers. It was at my birthday party, funnily enough. We snuck off into the bedroom and she told me she was ready. I remember being quite surprised, a little terrified, and really excited all at once.

I still feel the same way to this day, almost two years after that moment. Okay, maybe not so much terrified, but sometimes still a bit intimidated by her body. Don't get me wrong, my confidence in that regard has come a long way, but she is still so damn sexy that sometimes it's just a little hard to believe.

We've been together for about three years now, on and off. We've both graduated from high school and moved on; I'm over at University of Berkeley studying to be an Engineer and she's taking classes on campus at Berkeley City College. She's still figuring out exactly what she wants to do, which I think is great. Until then she does some waitressing at the local Hooters. We moved in together recently, and that has been an adventure in itself.

Now, when I say we've dated off and on, that's because of the aforementioned fights. We've broken up and gotten back together again a few times. We've gone on breaks. You know, the typical stuff. I guess that means we're not perfect. Oh well, I like whatever it is that we are.

Lately, we've lived up to this imperfection. There's been a bit of fighting. We've seen much, much worse - but things still haven't exactly been smooth sailing as of late.

The start of our recent troubles came a couple of months ago. Little did I know, this was also going to be the start of something...else.

As I stated before, we had just moved in together and were still in the process of exploring what that's like and how it can change relationships. For me, it meant wanting to know her better. Sure, I was pretty positive that I knew about 90% of what there is to know about her, but the 10% left is usually what's the most intriguing. Living together was a new kind of intimacy all together, and so with it came new questions.

One night one of those questions treaded on dangerous waters. While we were doing some messing around I got curious and asked her a question that I maybe shouldn't have asked her. As stated before, we've been on a few break: even one somewhat recently before we decided to move in with each other. They were usually over something petty that I did or said, and Summer would decide that she needed some space. It was rarely anything more serious during that.

I don't know what possessed me to ask this question, but that night I decided to ask her whether or not she had ever dated anyone during one of our breaks.

"What?" she paused, looking at me confusedly. "What makes you ask that, baby?" she put her hand on my shoulder.

"I don't know, just curious I guess. I mean, haven't you ever met anyone any of the times that we were broken up that you, maybe sort-of developed a bit of a crush on?"

"Have you?" she shot a glare that I wasn't sure how to interpret.

"No."

"Baby, the past is the past. Can we drop this and just focus on what we've got now?" she asked.

"So you have, then?"

"Why do you care so much?"

"I don't, babe. I promise, I'm just a bit curious," I gave her a reassuring peck on the lips.

She sighed. "Okay, please don't get mad. But there were a couple of times where I ended up dating someone after we broke up. Sometimes the fights are just too much, and I just don't think we can make it. But every time I've tried dating again...I...I realize how lucky I am to have what we have. And I realize that it is worth fighting for," she whispered, taking my hands within hers and staring into my eyes.

"What about this last time?"

"What about it?" she asked.

"Did you end up seeing anyone last time we broke up?"

"Why do you care?"

"I don't. I'm just curious."

"Yes. I did."

"What was his name?"

"Charles, don't do this baby..."

"Summer -"

"Babe, the past is the past. Just leave it alone, please?"

I looked at her and saw that she really didn't feel like discussing it any longer. Worrying that I might cause a fight, I decided to let it go. At least for now. She seemed happy by this fact, because she rewarded me by finishing me in that perfect mouth of hers.

After that night I couldn't get the idea of her possibly seeing someone else out of my head. I guess I shouldn't have been perplexed about the idea of Summer dating other guys. She was a virgin when we met, but she had dated other people. When we had broken up in the past I knew she had talked to other guys, but never really thought anything had materialized from it. I knew she had friends like Mark and Randy that had hit on her before and were likely prospects to hit on her anytime a beautiful creature like her was single. But we loved each other, and in some weird, naïve way, he had just assumed that she only had eyes for him all that time. A silly thought, really.

Either way, the thoughts were there and questions began popping into his head. The kind of questions you're not sure you want the answer to. The kind that can definitely start a fight, and in this case, did.

He kissed her longingly as she climbed off of him, making her way to his side where her left hand drifted towards his member.

She kissed him deeply as she began jerking her off. "Yeah, you like that?" she whispered into his ear.

"Yeah," he groaned, my mind swimming with unwelcome, borderline intrusive thoughts.

"Did that pussy feel good? I bet you wish you could cum in it, don't you?"

"Fuck yes..."

"Hopefully we can get this whole birth control thing figured out soon...I want to feel you in me...all of you."

"Damn...that'd be...hey, baby, could you slow down," I asked, gripping her hand and guiding her to a slower pace without completely stopping.

"What's up, baby? Everything okay?" she asked, a bit concerned.

"Yeah, everything's fine. I just...you know the other night, when I asked you about whether or not you'd dated other guys while we weren't together?"

"I thought we put that behind us, Charles..."

"We did. I did. I just...look, I'm not trying to start a fight or anything. It just has raised a few questions that I've been wondering about. I'm not mad, I just want to know."

"Know what?"

"When you dated these guys, did you all ever...do anything?"

She stopped her hand from moving and looked at me with a bit more concern. "What do you mean?"

"Like...physical?"

"Why does it matter? We're together baby, that's all that matters," she said, trying to reassure me and take my mind off the situation.

"I don't know. I'm just curious. I guess I am just wondering if any other guys have kissed my future wife since we first started dating," he chuckled weakly.

"Are you sure you want to do this?"

"Yes...please."

She looked at me for a minute as if contemplating what to say. "I mean...that's what happens when you date someone, right? You kiss them, you cuddle, things happen."

"So you're saying things happened?"

"I guess."

"How far?" he asked.

"What?"

"How far did you go?"

"With who?"

"Whoever. Whoever got the furthest." I looked at her for a response but she didn't budge. "Last time we broke up, did you kiss anyone? Be honest with me."

She looked down, avoiding eye contact with me. "Yes."

I put my on her face, and gently brought it back up so that they made eye contact. "Have you made out with other guys?"

"Yes."

"With touching?"

"Yes."

I started trembling ever so faintly. "Show me where other guys have touched you..."

She gave me a slightly confused look before grabbing my right hand and placing it on her hip. She leaned in and kissed me gently while scooting my hand down the small of her back onto her ass. Her eyes scanned mine intently, as if gauging my reaction. "Here..." she whispered into my ear, while grabbing my other hand and placing them both on her breasts, "and here."

I was visibly shaking just a bit now. I felt almost nauseous. There was a nervous energy that was building up inside of me that I didn't know how to control, or really what it meant. "Other guys have touched you there?"

She nodded.

"Over the clothes or under?"

"Honestly?" she asked.

"Please."

"Both," she said with a bit of a guilty look on her face.

I kissed her. "It's okay baby, I just want to know." She kissed me back. It was at that point that we both noticed that a certain part of my body had...grown a bit, and was not poking her in the side. She gently placed her hand over it, as if to keep it comfort.

"Okay," she said, as if admitting defeat. Maybe her guard was dropping a bit and he could get more out of her. Whether or not that is a good thing is, of course, another question entirely.

"Did they touch you anywhere else?"

She used her other hand to guide my hand down the front of her thigh, where it rested. She looked up at me, again as if gauging my reaction, before sliding it down to her pussy. It seemed wet.

"Another guy fingered you?" I asked, feeling a bit betrayed.

"Yes."

"Did anything else happen?"

She slowly began moving her other hand as my dick began to grow. "There were a few other things..." she said, barely above a whisper.

"Like what?"

"Are you sure you want to know this?" she asked, flashing me a serious look. All the while she had me in her hand, literally.

I paused briefly before answering yes.

"There may have been a few other guys who have had my hand on them like this."

"A few?" I asked.

"I've dated a few guys other than you, honey. These things happen..."

I nodded, looking at her to continue.

"There might have been a time when I did something like this..." she lowered her mouth onto my cock, faintly kissing the tip while never breaking eye contact.

"Just like that?" I asked.

"Maybe a little more like this..." she said, running her tongue down the shaft and underneath my balls, sucking on them a bit before burying the shaft in her mouth, working her way up and down it a few times.

"You...you did that to another guy?"

Her lips broke contact with my dick and she looked up at me like a scuba diver coming up for air. She nodded slowly. "Are you okay baby?"

"Yes. Did...anything else happen?"

"What else could have happened, baby?" she asked, looking up at me with my dick in her hand, slowly stroking me.

"I don't know..."

"Do you hope something else happened?"

"Why would I hope for that?"

"I don't know, you tell me," she smirked.

I tried as best I could to stifle a groan, but it escaped ever so faintly.

"Hmm...I wonder..."

She slowly worked my cock in her hand.

"What else...

Could have...

Happened."

She emphasized the last word, letting it hang in the air before trailing off in a sultry whisper that made me jump.

"I mean...I guess I can think of something," I said.

"Oh really? And do you think it's something that your pretty little girlfriend would let some other guy do to her?"

"I...I don't know."

"What if something else did happen?" she said in just about the most innocent sounding voice I've ever heard her muster.

We both just sat there, silent in the moment, each of unsure of what to say next. There was an elephant in the room, and we were trying to figure out whether we wanted it there or not.

"Baby...I kinda wanna hear you say something. But I don't want you to judge me, and I don't want you to say it unless it is true," I said, my voice quivering with hesitance.

"I understand," she said. And I got the feeling that she really did understand.

I leaned forward. "I...I kinda want to hear you say that other guys have fucked you," I whispered in her ear, barely audible.

"What?" she looked at me, confused.

Fuck. Maybe this was a mistake. Dammit, this whole damn thing was a mistake. This was all so weird and new and I didn't know what the fuck was going on. I just...I needed release. And I needed to know. Fuck it, I asked her again.

"Please don't be mad...but there's a part of me that kind of wants to hear you say that other guys have fucked you. Like, if things happened when we were on break or broken up...but I don't want to force you to say anything that's untrue," I barely managed to choke out, just a hair above the volume of the previous request.

She looked at me for a moment before looking down at my cock, and then back up to me. She leaned forward and looked me right in the eyes. "Baby...other guys have fucked me."

I exploded in her hand.

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cuck1cuck1about 2 months ago

Good story so far but slightly annoying how it switched from 1st to 3rd person at times.

iammweaseliammweaselalmost 2 years ago

So this dude didnt realize he had deep seated homosexual tendencies until now? Riiiiiiiiiiiiiiiiiiiiiight.

NegativeNellyNegativeNellyalmost 3 years ago

It’s my understanding that they aren’t married. Can a man dating a woman technically be a cuckold?

WhackdoodleWhackdoodleover 3 years ago
Inconsistent.

They were typical high school sweethearts but he was in grade 12 while she was I. Grade 10 and he met her at a party throne by his friend and he didn’t know anyone there even though they all went to the same school?

She wouldn’t have seen him for 2 years while he was in Berkeley but somehow goes to university and is a Hooters waitress? Why not skip the middle man and make her a stripper?

This story has done good moments but overall, it felt thrown together.

AnonymousAnonymousalmost 4 years ago
Curb Her

Slow down to 35 then Kick her to the Curb .

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