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For anyone who missed my first entry, I would encourage you to go back and read part one of this series! I’m going to be jumping in right where we left off last time, so that’d be the best way to understand the full context.
To provide at least a quick summary, my name is Kristen, I have been cheating on my husband Rob for 20 years without getting caught. We have been married for 15 of those years.
Also, to everyone who reached out via Reddit DMs since I posted my first , thank you for reading! I knew it would be a good idea to post about this online, and I very much appreciate all of the kind words and support.
So… last we left off was Rob’s 19th birthday, which was right before the end of our last year in high school. I mostly pushed what had happened at the party to the back of my mind, for some time. I had exams to focus on as well, but I couldn’t quite get it completely off my mind, seeing Jeremy like that.
After exams ended the horny thoughts came rushing back in full force, I started masturbating more frequently. It was clear that Jeremy hadn’t told Rob anything, because they still hung out all the time and everything seemed perfectly normal.
During that summer I became very interested in porn. I think maybe there was a part of me that believed that huge dicks were like, an exclusively for porn thing.. lol. For example how people will say “models set unrealistic expectations for women’s bodies” basically implying that those bodies aren’t attainable for ordinary women, I had kind of assumed that truly enormous dicks weren’t a common occurrence at all. I’m not sure if I thought male pornstars were like taking pills or something else, I just didn’t know and wasn’t all that into porn, before this happened.
But things were a little different now, I personally witnessed that someone I was close to had a pornworthy dick… and I was getting very curious about how common they might be, and how many guys I knew in real life could be equally hung, or maybe even bigger…
I was watching a LOT of porn that summer, and I specifically was fixated on size difference between the man and woman (I am very petite), so just imagining the experience of taking such a large cock, in real life.. was enough to get me off. More than enough.
My drive was extremely difficult to keep under control, I was almost always wet. I kept thinking back to that day after Rob’s party, constantly. I masturbated daily, almost always to porn, and always while imagining myself taking a huge dick. I became a little closer with Jeremy, I started talking to him more often. I also started closing my eyes and imagining Jeremy occasionally when Rob and I would have .
Despite all the temptation though I never cheated that summer. I was still determined to be good, I thought I’d be happy with just the fantasy, and that it’d stay only a fantasy.
I cracked eventually though, of course. Rob and I got into different universities. We decided it wasn’t going to be any issue, as we wouldn’t be far apart at all. The school he was attending was only one hour by car away from mine, which seems like nothing. One hour is however plenty of time to plan for your partner to arrive if you’re busy cheating…
I was really good that summer, I took pride in resisting my temptations, but then the summer ended and it was time for school. Rob left for school one week earlier than I did, leaving me alone in our hometown. It is also worth mentioning that my own birthday is right at the very beginning of September, so this meant that we wouldn’t be together on my birthday, which I’ll admit I was a bit upset about.
I understood of course, he was going to have a heavier course load than me and was staying in dorms so he needed time to prepare. The university I was attending was close enough that I could continue living with my parents, and drive into school each day, so I didn’t have nearly as much preparing to do.
My birthday fell on the weekend immediately before school started, my best friend Maya arranged to have a party for me at her house. Rob had already left town for school.
This is the part of the where things start moving a little bit faster…
I messaged Jeremy (remember MSN lol). I knew what I wanted but I was nervous. I started out with just small talk but made sure to ask whether him and Taylor were still “seeing” each other. He laughed, and explained that no they’re not dating, told me that they fuck sometimes but that she wouldn’t agree to put a label on it because she was planning to do several semesters abroad.
I was feeling lonely already even though Rob had only been gone a few days, it was a shock because leading up to this, we had been spending every day together.
I asked Jeremy if he was planning to be at Maya and Taylor’s for my birthday party, he said yes. I asked if he knew whether Taylor would be there, he said no, she’s already left for school as well.
At this point I feel as though I’ve gotten the answer I wanted, it seemed likely that the reason he was going to come to the party was either for me or for Maya, since the girl he was hooking up with wouldn’t be there. Based on the way he interacted with me compared to Maya during our previous encounter… I had good reason to believe it was me he wanted.
I took a deep breath… I asked him to video call me. He agreed. We did chat for some time but I ended up confessing pretty quickly that I couldn’t stop thinking about him all summer.
He asked me if I wanted to see it again (!!!) and of course I said YES please… so he pulled it out on webcam and gave me a much longer look at it, he was stroking himself for me while spitting on it, showing me different angles to really exaggerate how big it was… I was ecstatic. What turned me on the most was knowing that this was Rob’s friend, and that he was willing to do this anyway. His friend had been out of town for only a few days and already he was eagerly stroking himself over webcam with that friend’s girlfriend… wow! The thought alone was sooo exciting.
I wanted to be bad too, so I showed him everything that night. This was three or four days before the party. I stripped down and spread my legs for him over the webcam, he asked me to spread my pussy lips so he could see inside, and he asked me to bend over and spread my cheeks to get a look at my asshole too. I wasn’t certain what came over me, but I just did everything he asked. I loved it.
We both had a few orgasms over webcam, then while talking afterwards we made plans to hook up at my birthday party on the weekend. I was just daydreaming imagining what it would feel like inside of me.
But I still had my guilt to contend with, also. The following night, I cried, a lot. I called Rob and said I missed him, but I never said anything about masturbating for Jeremy. I started to feel more and more nervous in the days leading up to the party, and more and more guilty.
Finally on the day of the party, I felt no doubt. I was so relieved… I just wanted to fuck him and get it over with, I hadn’t put any thought into whether or not I would continue hooking up with him after that weekend.
We’re partying at Maya’s house, we had a lot of drinks (in Canada drinking is legal at 19, in case there are American readers), and seeing as it was my 19th birthday it was a somewhat drinkingcentred event. My nerves about seeing Jeremy really compounded that as well. I was drunk, but I knew to stop before it got out of hand, I had planned for this.
I saw Jeremy enter the party and immediately started getting ready.
I told Maya “I’m too drunk, I’m going upstairs to nap in your bed ok” and of course she says yes. I made my way to her room where Jeremy knew he would find me.
Five or six minutes later and he was already sneaking through the door into her room. I panicked a little because I expected him to take longer, and anxiously asked about what excuse he gave to leave the main area so quickly. He said he told them he was going to smoke on the back balcony and they didn’t question it… that was good enough for me.
We weren’t talking very long before he pushed me backwards onto the bed. He started kissing me deeply and passionately, he was a very tongue heavy kisser… and while we were making out he was squeezing my ass in his hands. Eventually his hands crept around to my inner thigh and then finally he was rubbing my wet pussy through my jeans while we kissed.
My mind was all over, just absolutely racing. I was cheating on my boyfriend… or I was about to, I wasn’t sure exactly where the line was.
I was so indescribably wet from excitement.
He sat me up on the bed and took off my shirt, and then my bra. That part happened so quickly, I hadn’t even had time to process it, but he was already squeezing my tits and playing with them. He got on his knees and started licking and sucking on my nipples, and his bulge was enormous through his pants because of how hard he was.
I had had enough. I told him to get on the bed, and I straddled him. While we were kissing some more I undid his belt and the button and zipper of his pants, I reached my hand down beneath his boxers and started stroking his massive cock, he was so hard.
I’ll never forget how hard that man was for me, it was surreal. Touching him again reconfirmed everything I had been fantasizing about all summer, the girth was impressive, I couldn’t quite wrap my fingers all the way around it.
He liked my tits, like, a LOT. He spent a lot of time sucking them while I was on top of him. I asked him if it was because he never got to see them during our poker game, he told me he just thought they were perfect, which was flattering.
Then his boxers were all the way off… and then my pants were coming off, things were heating up fast. The nerves and the guilt slowly started to creep back in on me, but I thought I could keep myself distracted just out of sheer excitement. So when I started feeling a little guilty I tried to keep busy by sucking his cock, I went down on him while he laid back and relaxed. I sucked him for at least a few minutes but he was so girthy, it was hurting my jaw to continue, I started spitting on his rock hard cock and giving him a wet handjob instead.
The only problem is now I was feeling really guilty. I had just spent the past several minutes with my boyfriend’s friend’s dick in my mouth and had never done anything like this before. I just wanted to fuck ASAP in that moment, I wanted to just take his dick inside me before I had any more time to think about what I was doing.
I was going to get to live out my fantasy of being with someone huge and I didn’t want to stop, I needed to just go for it before I could second guess myself any further.
So while I’m stroking his dick which is covered in my spit, I ask him please fuck me, I was practically begging him.
Of course he says yes.. so he lays me on my back on the bed. I took off my panties eagerly and spread my legs wide for him, I wanted to give him a good long look. He spat right on my pussy just as I was touching myself, and I started to moan. Then he slid his fingers inside me while I was rubbing my clit, and fingered me hard until I had this incredible, shaking orgasm. I felt every second of that orgasm and it was wonderful, I felt my pussy clenching and unclenching on his fingers while my legs were frantically shaking.
After I regained my senses, a big wave of the guilt came over me this time, I knew I was running out of time. I couldn’t afford to act cutesy anymore, I had no choice but to drop the act. I looked him straight in the eyes and demanded that he fuck me right now, I even grabbed his huge cock with a firm grip, and I started pushing my pussy right into him. I felt him slide and glide over my eager pussy, and the tip just barely slid inside once or twice, but then he says “wait, not yet”
FUCK! Now I’m panicking. I needed him to fuck me immediately. I was going to break if I needed to feel guilty any longer.
But he said “I want to taste you too,” so he starts licking my pussy. While he’s licking and sucking my clit he slides his fingers inside me again while he’s stroking himself with his other hand, this whole situation is so hot, but unfortunately him wanting to eat me out just gave me time to reflect on my guilt.
So I interrupted him, I said something along the lines of “ok let’s fuck now, what’s your favourite position?” hoping he would say doggy or missionary so I could just bend over, lay back or do whatever else it was I needed to do in order for him to put it inside me.
He says “”…
Ok, sure. I had never tried that with Rob. Maybe it would help my mind stop wandering. He asks me if he can face fuck me and I say yes, so he gently lays my head hanging off the edge of the bed and slides his cock into my throat. Then he leans forward and starts licking and fingering my pussy at the same time as he’s thrusting in and out of my mouth. This didn’t last long, like I mentioned his girth made it a little painful to suck for a long time. But it worked at distracting me just enough.
I pushed him away to indicate I needed to switch positions, and he got off me. He laid down and I immediately straddled him again, completely nude this time, with my bare wet pussy directly pressed against his shaft.
I grinded my pussy against him for a quick minute and then reached down and wrapped a hand around his cock, guiding it into my pussy as I sat my weight down onto him.
By the way, when girls say the girth counts, we really aren’t kidding. This man’s cock stretched me so good, that feeling was pure bliss, the first few seconds that I had the entire thing inside me. Once it was completely inside, we just stared into each other’s eyes for a few seconds, I leaned forward and started to kiss him again, and when I was ready I started rocking back and forth on him.
I was so overwhelmed by how big he was, I couldn’t move fast. I had to take it slow. I rode him really deep and slow and gentle for several minutes, while we were staring at each other’s bodies in between breaks of deep kissing and running our hands all over each other. He filled me up more than I had ever experienced, or thought I WOULD ever experience, and I was loving every second that his dick was inside me.
Then we got interrupted by the sound of someone slamming the bathroom door (it was located right next to Maya’s room) which startled me back into my usual state, and I was completely overtaken with anxiety that they might have heard me moaning.
I started crying, I told Jeremy I wanted to stop. He said ok and he was very supportive. I told him I’m sorry he didn’t get to cum but he said not to worry about it. I told him, you’ve been gone too long, I don’t want anyone to hear anything or know what’s happening. He agreed and got dressed, he told me that he would rejoin the party until it was over and then come say bye to me before leaving and I said ok. He gave me one last long kiss before heading back downstairs.
I then spent the next several hours feeling horrible, there was no going back now, not really. I fucked my boyfriend’s friend. I kept running around in circles in my head, looking for excuses like: he didn’t cum, so it doesn’t “really” count as having … or, I only came when he was fingering me and not during the actual , which means neither of us fucked till orgasm. I knew it was all stupid bullshit. I also tried texting Rob, just saying I miss him and feel lonely. I didn’t confess to anything.
Finally at around 3:50 a.m. Maya comes into the room, she says everyone is leaving but that I’m welcome to stay in her bed for the night, and she will crash in her older sister’s bed along with her boyfriend. She also mentions that Jeremy asked to crash on the couch downstairs. It took all of my self control not to react visibly to the news that he was staying.
A little over an hour later, around 5 a.m. Jeremy comes in the room and asks how I’m feeling. I’d had lots of time by that point to cry it out, so I told him I felt better and asked if we could fool around some more. We both got undressed again and I apologized for my reaction from earlier but he reassured me it was fine.
I got on my knees and sucked him some more, it hurt still but I didn’t care this time I was just so grateful that he was gentle with me. I kept sucking for what felt like a really long time, until my eyes were watering and I was slobbering all over my own face and tits.
We were very lucky that Taylor’s room (where Maya was sleeping) was located in the basement, so I was much less nervous about being overheard this time. I sucked him the best I could until he couldn’t take it, and then he grabbed me by the throat and laid me on my back, and told me to spread my legs.
I very much enjoyed obeying him. He held me down while he slowly filled me with every inch of him for the second time, and again our eyes locked right at the moment he was buried deep inside me. I reached one hand down and started rubbing my clit while he fucked me, and seeing that I was enjoying it he started pounding me so hard. I had never experienced anything like this, I felt so full, it all felt so good. I forgot about the guilt.
Finally I wasn’t thinking about Rob at all anymore, and that’s when I was able to cum. I had another incredible orgasm, this time with Jeremy’s huge cock filling me up while I squirmed and shook underneath him.
That must have really turned him on (he told me my pussy got extremely tight while I was cumming), because shortly after he pulled out and he shot cum all over my tits.
I was laying there, sore, exhausted, absolutely trembling and covered in his cum that still felt hot on my skin. Something just clicked in my brain, I didn’t feel guilty about this.
I smiled at him and he grabbed some tissues and cleaned the cum off my tits. I was practically floating, I did it. I got to live out the fantasy I wanted, and it was everything I could’ve imagined.
I asked Jeremy to stay with me that night. The only other moment of anxiety I had was realizing that we should have used a condom, but I knew that Jeremy had only been with Taylor and a few other girls before, so the risk seemed reasonably low.
Neither of us slept, Maya had some movies in her room on DVD so we put on The Road To El Dorado on the little TV in her bedroom. He spooned me while we watched naked, and towards the end of the movie he slid his cock inside me again while spooning.
We fucked two more times, the first time he came in my mouth and the second time he wanted to cum inside me. I told him no, but agreed to let him cum on my pussy lips. He did cum right on my clit but barely had any cum left haha, it was just a few drops, so I suppose it might have been ok to let him cum inside after all. Regardless I was just absolutely thrilled with how the night had gone, it was a total rollercoaster, but it ended with me getting fucked three times and swallowing Jeremy’s cum. I would never be the same after.
From this day onward, I started plotting. I didn’t want to feel shame for being highly ual anymore, I didn’t want to feel guilt over something as simple as cheating.
Jeremy swore on his soul that he would never tell Rob, Maya or Taylor (spoilers Maya finds out but we’ll save that for another time). And I walked away from that party feeling happier and better than I had walked into it.
This was the beginning. Things got very out of control for a while in my first few years of university, I’ll share those stories next time…
ero
