Daisy, still to this day, is easily one of the hottest girls I’ve ever laid eyes on. 5’6, 19 years old and in her physical prime, she was practically a human Barbie Doll. Long, bleached blonde hair that ran down to the small of her back. Electric blue eyes and a heartbreaker smile. She was athletic, with perky little B cup tits, an amazing ass that she loved to show off in her yoga pants, and abs that made you want to stick your tongue into her belly button. It’s been almost 17 years and I still can’t believe my luck for having pulled this girl.
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I had a job working part time at a restaurant in town, and she started as a hostess there about a year before my affair with Nicole. We didn’t have many interactions at first, because I had immediately pegged her as being out of my league, and because every guy in the place was taking a shot at her. She rejected all of them. Daisy loved the attention though, and was always playfully flirting with the guys. She later confessed to me that it drove her crazy that I never showed interest in her. Also, our work schedules rarely lined up, so I wouldn’t have gotten many chances to get at her even if I’d been trying to. Eventually she started dating one of the bartenders and I ruled her out completely.
Around the start of my affair with Nicole, Daisy and the bartender broke up. I’d begun moving with some newfound confidence, and unbeknownst to me, Daisy had been harboring quite the secret crush on me for a while. I couldn’t have been more oblivious to it. Her schedule changed during my time with Nicole and we started working a lot of shifts together. Because I was so focused on Nicole, I didn’t feel any nervousness talking to Daisy, despite how hot she was. Our conversations got deeper, and at times more risqué. Still, I was completely oblivious.
About a month after my affair with Nicole ended, Daisy, myself and another coworker were on a lunch break and got to talking on the subject of losing and taking virginity. I mentioned that my one experience popping a girl’s cherry was terrible and that I wasn’t in a rush to do it again. Daisy made a playful jab that I must not be good in bed, and we laughed it off.
“No, but honestly it was really painful for her. We went slowly and I tried to be gentle, but I’m… kinda big down there and it hurt her a lot. She actually cried from pain the entire first month of us having sex.”
I knew I was taking a risk sharing that information, but Daisy was never the type to get offended. Her response however, caught me off guard.
“I always hear that the first time hurts but I guess I was really lucky. My first time felt amazing, like no pain at all. And my ex was fucking huge.”
My eyebrows raised at that. Fucking huge? She saw the look on my face and turned bright red while she gave me a devilish smile. That was the moment I realized she was into me. That look. I don’t know what compelled her to tell me her ex was big, but I felt competitive almost immediately.
Our coworker rolled her eyes and walked away, but I moved a bit closer and gave her a sideways stare.
“There’s always a bigger dick,” I said, before smiling and walking away. My heart was pounding, and I could sense the inevitability of the moment. What a cocky little fuck I was back then. I was still years away from learning just how true that statement would be.
We started texting within the week, which quickly became heavy flirting, and even more quickly became unfiltered admissions of desire. Daisy held nothing back, confessing that she had been into me for a long time, practically since she'd first met me. She thought I didn’t like her, which was out of the ordinary for her and only fueled her infatuation with me. I asked her on a date, and when I picked her up we were so eager for each other that we kissed before we even got to my car.
That day, two things became apparent to me:
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Daisy was very into me.
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She was a different person behind closed doors.
To everyone that knew her, Daisy was a typical good girl. The All-American, Christian, polite, sweet, girl-next-door type. She would kiss her dad on the cheek each night when she said goodnight. But privately, Daisy was a freak. She was relentlessly horny, and she loved everything about sex. We talked about everything, shared sexual experiences, what we liked, and what got us off. I confessed to her about my affair with Nicole, and that I felt a bit guilty about it, but the story only turned her on. She asked a million questions about the cheating, wanting to know the intimate details. She confessed to me that she had broken up with the bartender at our job out of guilt because she’d cheated on him.
I couldn’t believe it, she never struck me as the type. She told me she felt awful about doing it, but I know I saw a twinkle in her eyes when she told me how it happened. She’d never admit it, but she liked telling me what she did. She told me that she’d seen her ex-boyfriend at a party, and ended up on her knees for him, where she stayed until she made him finish in her mouth.
“The one with the huge dick?” I asked playfully.
“That’s the only ex I have,” she replied.
She felt my cock through my jeans that night but stopped me from taking it out because she didn’t want to regret moving too quickly with me. The next morning, she came over to my place and I guess that was a long enough wait for her. She climbed onto my bed and slipped her jeans down over her bubble butt, showing me the little blue thong she was wearing. It had bows on it, which was appropriate because her pussy was a gift.
She sucked my cock, looking up at me with her blue eyes, telling me how nice my cock was while she kissed it, and then she begged me to fuck her with it, telling me she’s on the pill and that I didn’t need to use a condom. I didn’t hesitate. She looked so pretty on her knees in front of me, I would have cum inside her even if she wasn’t on the pill. I would’ve done whatever she wanted.
The funny thing about Daisy.. she is still to this day one of the hottest girls I’ve ever been with, but she had the loosest pussy I’ve ever felt. She handled my dick easily, pulling me balls deep into her right away. Honestly, I’m grateful she was loose, because she looked so good taking my cock that I wouldn’t have lasted long if she wasn’t. I also didn’t mind, because she was the first girl that could really take my size without complaint or me having to concentrate on not hurting her. We fucked all day, and the entire next day. I came in her mouth and pussy over and over, the way only a 20 year old can. By the end of the weekend, I was head over heels in love with this girl. I ignored the red flags. I thought she was perfect, and our relationship quickly bloomed.
We kept our relationship secret for a little over a month, not wanting to cause a commotion at our work. In that time, we hired a few new people, and I watched all of them pine after her with a smirk on my face. I loved knowing she was mine and everyone else wanted her. I loved watching her reject them. Eventually, the secret got out and my coworkers lost their minds. A few guys at my work were pissed off and jealous, but most of them were hyping me up and telling me how lucky I was. I really felt like the man.
Our relationship burned hot and heavy for 8 months. We had more sex than I’d ever experienced to that point. She knew what she liked, knew how to please me, and taught me exactly how to fuck her. She would kneel in front of her mirror so I could watch her suck my cock from other angles. She did anything I wanted and suggested things I hadn’t thought of. She even let me fuck her in the ass a couple times. We fucked hard and fast, slow and intimate, and everything in between. Looking back, I can’t remember us doing much else besides having sex. We spent all our time naked. I learned tricks from that girl that work wonders on other women to this very day, especially when it comes to eating pussy. Daisy couldn’t cum from penetration, but she loved having her pussy licked and sucked on, and she used to hold her breath and turn bright red when she came for me. Being with her was like being in a PhD program on how to fuck. It was heaven.
Her house, my house, either of our cars, the storage room at work, we found ways to fool around wherever we were. She loved to present her pussy to me from behind, and I’d often find her already wet and waiting for me, bent over and showing me her pink flowery lips. I loved the way she would stare daggers into me with her blue eyes while I pounded her, and how red her face would get while she took my cock.
But then, things ended abruptly. I had plans after work with some friends, and she asked me to come over instead because she was horny. I stupidly told her no and she was upset about it. Only 30 minutes later, my plans were cancelled and I texted her telling her that I was on my way to her house.
I didn’t get a text back immediately, but when she did respond she told me she wasn’t feeling well and not to come. I told her I was already on my way, practically down the street. She told me again not to come but I insisted, saying I’d take care of her, and she relented. Daisy took a long time to answer the door when I got there, and when she did she was bundled up in sweats and a hoodie. She was annoyed at me for coming. She didn’t seem sick, but at one point that night she started crying, and told me she was just feeling really emotional but wouldn’t tell me why. We didn’t have sex that night, which was a first for us.
After that night, Daisy was cold with me for the week that followed, and then ended things, telling me she’d lost the spark. I was blindsided, and devastated. This girl was telling me she wanted to marry me 2 weeks ago, and now she’s lost the spark? It didn’t add up. I experienced the first truly painful heartbreak of my life. I was a wreck. Daisy stopped working at the restaurant, and a little over a month later, word got to me that she had gotten back together with her ex.. of course.
If there had been one negative in our relationship, it was her ex. She talked about him often. Too often. She’d dated him all 4 years of high school, and according to her, he'd treated her like shit. He was a gym rat and a player and did all the wrong things. She hated that he got her to cheat on the bartender from our work, which she swore was a mistake she’d never make again. I asked questions about her ex too, also too often. Girls I’d been with always talked to me about my dick size, and I liked the praise, but Daisy didn’t really fixate on it, and it made me jealous. When curiously got the better of me a few times, I asked her if I was bigger than her ex, and she never gave me an answer that felt honest. It was always, “I can’t really remember.” The clearest answer I ever received was that she was pretty sure my dick was longer than his, but he was a little thicker than me. My over-inflated ego let out some air at that.
And now, she was back with him, a month after abruptly ending things with me. I couldn’t help but wonder if she’d seen him before it ended. I imagined her sucking his cock at a party without me knowing, or him fucking her in his car outside her house while I was at work. I thought back to that night she told me not to come over. She’d been so horny only 30 minutes before, and then was completely different once I told her I was coming. Had she texted her ex when I rejected her? Were they fucking when I texted her? Did she have to rush to make him leave? I knew in my heart that it was very likely that she cheated on me that night, not expecting me to show up. It all added up.
Making these thoughts more painful was the fact that I had been with a cheating woman before. I knew how raw and intense cheating sex could be, and I could imagine it so vividly.
I had no idea what her ex looked like, just that he was buff and had a huge dick, but my mind filled in all the blanks as I imagined what he was doing to her. I knew he was fucking her now because they were dating. But my thoughts were always the same.. her cheating on me with his cock. Because I was so depressed, those thoughts began creeping in while I masturbated, though tried to fight it. I’d be watching porn, and then my thoughts would shift to Daisy, and I’d imagine how she’d look, the faces she’d make, and the things she’d say to him while she took his cock. Was he that much thicker than me? Often times, the thoughts would take me out of the moment and turn me off, and I’d stop jerking off. But as time passed, those thoughts continued until I started cumming thinking of them, followed by intense periods of self hatred and post nut clarity.
Eventually, I grew out of it. I had a dry spell for a several months, and then bounced back. I started fucking a new girl at my work, a strikingly pretty Persian girl named Samira, and we started dating. She should have been an excellent rebound from Daisy, gorgeous and a sweetheart, and we connected emotionally.. but she was boring and sexually conservative. I was in no place for a relationship, and when she moved at the end of summer to go to school out of state, I wasn’t bothered. Samira could never get me back to the highs I felt with Daisy or even Nicole. We continued on as a long distance couple for a little over a year, and during that time, I cheated on her constantly. It was terrible of me, I know. I always felt terrible guilt and regret afterwards, but that never hindered my promiscuity. Because of the emotional connection I had with Samira, it was easy for me to avoid developing feelings for the girls I was fucking on the side, and my lack of feelings towards them only seemed to attract more opportunities.
During this time, I leaned heavily into my fetish for cheating women, and became completely infatuated with it. It was intoxicating, and I loved the thrill of the chase. I was addicted to the moment that lines were crossed that couldn’t be uncrossed. I looked for sustained eye contact from girls who shouldn’t be looking my way at all. The days or weeks of playful flirting and slow escalation that followed. Pushing the envelope, increasing the temptation, and watching the girls make the mental calculations, reasons to convince themselves that nothing wrong was happening and that it was just playful flirting. Her boyfriend or husband had nothing to worry about, even though she made sure never to mention me at all.
I chased the inevitable moment that we ended up alone, and somehow standing far too close to each other, looking at each other in a way we both know is wrong, taking baby steps toward a point of no return. I chased the moment when temptation swung out of control, and her body betrayed her thoughts, knowing she should stop but physically refusing to listen to anything but the throbbing she felt between her thighs. Just a little more, like turning off your alarm in the morning and closing your eyes for just one extra minute of sleep, only to wake up 20 minutes later now terribly late. And now she’s gone too far and she knows it.
I chased the moment when she knows she’ll probably feel guilty later. But she realizes regret is inevitable. She’ll regret it if she cheats on him. But even if she doesn’t, there’s an aching in her loins that will make her always wish she’d just gone through with it. She can see herself touching her pussy at night imagining how it would have been.. wishing she had done it. And so she gives in. Her pleasure in that moment more important than anything else in her life. Ruled by primal desire, she gives in, and gives me what shouldn’t belong to me. I chased those moments desperately.
If you haven’t been in that situation, you might find my description of that behavior abhorrent. You wouldn’t be wrong.. it’s terribly selfish, reckless, and hurtful. But I would hope you can imagine for those who have lived it, how truly intense the release that comes with it was. Like a dopamine bomb, sex with unfaithful women was a schedule one drug.
I almost exclusively targeted girls in relationships. It was more convenient that way, because their cheating made it easier for me to continue cheating myself. Aside from mainlining lust, was also trying to rebuild my broken ego through the affirmations of unfaithful women, and to an extent, it worked. It was one of the most sexually promiscuous periods of my life. I didn’t succeed in seducing every taken girl I’d set my eyes on.. in fact I failed much more than I succeeded, but between school and work, I had plenty of options to pursue. It was also during this time that I met up with Nicole for our final goodbye.
That year, I was the other man to 5 different girls. 2 of them were short and intense flings,1 was married and betraying her religion as well as her husband, and the other 2 were complete sluts who let me fuck them behind their boyfriend’s backs for months. I never felt feelings for any of them, but the cheating sex was always hot, and always the same. The tension was palpable. The build up to the moment where lines were crossed was intoxicating, and the sexual release was incredible. I fucked these girls and they all told me the same things Nicole did.. my cock was better, bigger; I fucked them better; Their pussies belonged to me even though they loved their boyfriends. It was fucked up, but it rebuilt my ego. Daisy felt more and more like an anomaly. But as my self confidence rebuilt, the guilt of cheating on Samira started to wear me down. I loved being the other man, but I didn’t enjoy being a cheater myself. Of everything I’ve done, I hated the guilt and shame that followed that. I knew Samira deserved better, and I could sense a change growing in me, so I ended the relationship.
For a few months, I was happy. I’d finished school. I’d found a new apartment in the city. Got a new job. I was no longer pursuing taken women. Things were looking up.
A friend invited me to a small party, and when I walked in the door to his flat, the first person I laid eyes on was the girl who would end up changing my life forever.. Vanessa.