<p>I’ve always been a little different, at least where sex is concerned. I remember reading erotic stories of domination and submission soon after I started masturbating (God bless the internet for making it so much easier to explore my sexuality).</p><p>The very first porn video I can remember loving featured two women having strapon sex. There was a femdom tone to the whole thing and I remember being absolutely taken with it. It felt like a revelation, honestly.</p><p>I won’t bore you with the whole tale. The point is, my journey eventually took me to cuckolding. It happened after I married Naomi. I don’t know if I started fantasizing about being a cuckold because it seemed like there was a chance of it actually becoming a reality (I was married, after all) or if it’s always been lurking there as my ultimate fantasy, but it quickly became the only thing I masturbated to.</p><p>The first time I told Naomi about my fantasy, she was…unenthusiastic, to put it mildly. To be honest, she was pretty upset. She seemed to have two concurrent reactions. One was that she thought I was trying to get us to have an open marriage so that I could fuck whoever I wanted. The other was that she thought I just wanted her to be some kind of wanton slut, fucking anyone and everyone so I could get off on it.</p><p>We ended up having a lot of conversations about it, which I gather is pretty common with this sort of thing. When you’re introducing a totally foreign idea to someone, it’s going to take a while for them to understand it.</p><p>Then we had a conversation that laid the groundwork for the version of cuckolding we enjoy. It happened three months (or thereabouts) after I first introduced the idea.</p><p>It was late on a Friday night. Naomi and I were in bed. I believe we were both reading on our iPads (iPads were really big at the time).</p><p>“Can we talk?” Naomi said as she let her iPad drop to her lap.</p><p>I tensed up immediately. In my experience, that kind of introduction to a conversation rarely results in anything good.</p><p>“Of course,” I said, trying my best not to seem apprehensive.</p><p>Naomi looked over at me, paused for a moment, took a deep breath, and said, “Someone at work asked me on a date.”</p><p>Because I was prepared for the worst, I was caught off guard by the news. It took a few moments for it to register that my wife was almost certainly using this as a way to talk about my desire to be cuckolded.</p><p>“Really?” I said. It was all I could think of to say. I didn’t want to seem overeager.</p><p>Naomi’s lips curled into a little smile. It almost seemed like she was trying to repress it. “Yes, and it got me thinking about…well, about your fantasy. You know I’ve struggled with the idea of making that a reality. I haven’t been able to wrap my head around making that happen.”</p><p>That was true. Naomi couldn’t get away from the idea that I wanted her to be a slut, something she found offensive. No matter how many times I assured her that wasn’t what I was looking for, she just couldn’t comprehend that I wasn’t looking to turn my wife into a slut.</p><p>“Well,” she continued, “weirdly enough, being asked out on a date cleared things up for me.”</p><p>“How?” I asked. By this point I was having a hard time containing my excitement.</p><p>Naomi rubbed her fingers over the darkened screen of her iPad as he looked down. She seemed a little nervous, which I found impossibly cute.</p><p>Then she looked up at me and said, “I wanted to say yes.”</p><p>“Did you?” I replied instantly. I knew I was too excited, but I couldn’t help it.</p><p>Naomi shook her head. “No, of course not.”</p><p>For a moment, my hopes were dashed. I remember feeling like the conversation was a confirmation of my desires to be a cuckold, though. The excitement I felt at the notion that she’d accepted a date with someone else was palpable.</p><p>“I did spend the rest of the day thinking about it, though,” Naomi said as she brushed aside a few strands of hair that had fallen in front of her eyes. “And thinking about it helped me discover that I want to cuckold you, though perhaps not in the way you’ve imagined.”</p><p>“How do you want to cuckold me?” I asked. I knew I was failing to hide my overwhelming excitement.</p><p>“I want a boyfriend,” she said. “I want to date someone. I want it to be more than just sex. I need it to be that, to be honest. That’s been the thing that’s been holding me back. I just wasn’t aware of it until now. I hate the idea of finding some big cock guy to pound me while you watch. Nothing about that turns me on. The idea of dating someone and experiencing all that early relationship stuff, it turns out, is really hot to me.”</p><p>Looking back, I distinctly remember that I wasn’t hard but I felt an almost overwhelming sense of arousal as I listened to her. I think it’s because she was telling me that she was ready to make my fantasy a reality. I knew that dating someone would absolutely lead to having sex with someone. I mean, that was the whole point, right?</p><p>There was something about the look in her eyes that made me try and turn the conversation into something lusty. To me, it looked like she was suggesting we fool around.</p><p>That’s why I moved closer and pulled back the sheets. She was wearing a pair of exceptionally sexy white lace boyshort panties. I found the sight of them thrilling as I moved my fingers over her inner thighs.</p><p>“I think it would be incredible if you dated someone,” I said.</p><p>A quiet, lusty moan escaped Naomi’s lips as I ran my fingers over her lace-clad pussy. “Yeah?” she said softly.</p><p>“I can’t really explain it, but yes. In fact, I’m pretty sure I’d find it hotter than if you were just finding some random guy to fuck. Just hearing you talk about it, even a little, has me insanely excited.”</p><p>By that point my cock was hard. Being a little closer to Naomi and touching her was enough to give me an erection as thoughts of her dating someone else filled my head.</p><p>“You’d really be okay with me having a relationship with someone?” she asked as her fingers moved between my legs. It felt heavenly when she touched my cock.</p><p>“Absolutely,” I said. “As long as you don’t leave me, of course.”</p><p>I moved my hand into Naomi’s panties as I said it. She smiled and then her face quickly took on a look of pleasure as my index finger found her clit.</p><p>“I can’t see why I’d ever leave a man willing to let me date someone else. If I can have the best of both worlds, I’m taking it,” she said.</p><p>In hindsight, that was the moment I knew things were going to work out. It was a strong indicator that Naomi really had thought about all of this. She’d considered the potential fun of being married to me and dating someone else and she clearly enjoyed the possible thrills that would come from such an arrangement.</p><p>“You might not be able to watch if I’m dating someone,” she said. “He might not be comfortable with it. He might just think I’m an unsatisfied wife cheating on my husband.”</p><p>I hadn’t considered that, but in the moment it honestly didn’t seem problematic. I’d shared with Naomi that the idea of watching her with someone else was a turn on for me, but it never struck me as a necessity.</p><p>“That’s okay,” I said. “The thought of you being with someone else is more than enough to turn me on.”</p><p>Naomi had worked my cock out of the front of my boxer shorts and was stroking me at that point. I couldn’t help but moan. Her fingers felt fantastically good as they moved up and down my erection.</p><p>“Oh yeah? Are you thinking about me being with someone else right now?” she asked. The sense of lust in her voice was incredible. She was totally into it. It probably helped that I was still playing with her pussy.</p><p>“Yes,” I admitted. I was absolutely thinking about it. I couldn’t get images of her doing all manner of dirty things with another man out of my head. “Are you thinking about it?”</p><p>I pushed two fingers into her wet pussy as I asked the question. The dampness between her legs was all the answer I needed. There was no question she was thinking about it. Still, it was nice to hear her admit it.</p><p>“Yes,” Naomi admitted before closing her eyes, rolling her head back, and unleashing a surprisingly loud and long moan.</p><p>I’ll admit that hearing that one word was enough to bring me right to the edge of orgasm. It felt momentous. It was obvious she’d been thinking about it, but hearing it felt like taking a much larger step. I wanted to probe a little more, to see if I could get her to open up a little more.</p><p>“Are you thinking about the guy that asked you out?” I asked.</p><p>Naomi opened her eyes and looked at me. She had this endearing, nervous look on her face. She briefly, lightly bit her lower lip. It was so fucking sexy. She was admitting it without saying a word.</p><p>It was exceptionally hot to hear her say, “Yes, I’m thinking about him. I can’t help it.”</p><p>I was still playing with her pussy. She’d started to moan a little louder and her breathing was definitely getting heavier. She was close to cumming.</p><p>I was too. I loved that she was thinking about someone else as we sat in our bed. She was picturing another man and was likely thinking about doing something dirty with him. I wasn’t sure if I should ask for more, though. We’d had enough conversations about cuckolding and sex in the past three months for me to know that she didn’t always think about it the same way I did. I didn’t want to ruin the moment by asking if she was thinking about his cock because I knew she probably wasn’t.</p><p>Thankfully, Naomi stepped in. She stroked my cock a little faster as she said, “I’m thinking about kissing him. I’m thinking that I wished I had said yes today and that he and I were on a date right now, that our date was coming to a close, that we were in his car right outside the house, that I was kissing another man while you were waiting inside.”</p><p>Now it was my turn to close my eyes and roll my head towards the ceiling. I couldn’t believe how hot it was to hear Naomi express her desires. It seemed that she’d taken my fantasy and made it into something that worked for her. The whole thing turned me on immensely.</p><p>“God, Naomi, that’s so hot,” was all I could manage to say. My cock was harder than it had ever been.</p><p>With surprising swiftness, Naomi released my cock, pulled off her panties, and straddled me. She sank her wet, hot pussy onto my erection and rode me.</p><p>She kissed me fiercely. Her tongue darted in and out of my mouth. I did my best not to cum immediately as I felt her slick pussy swallow my cock.</p><p>Neither of us said anything. I assumed Naomi was indulging in a bit of fantasy play just like I was. I didn’t know who’d asked her out, but I imagined a handsome man. I imagined her riding him instead of me. I imagined her in his bed, straddling him, taking him into her pussy as they kissed and he played with her breasts.</p><p>It was less than a minute before we both came. There was no way it was going to last longer. We were far too turned on.</p><p>Afterwards, I couldn’t help myself. I had to know. I knew it was potentially a stupid question to ask, but my curiosity was too strong.</p><p>“Were you thinking about him?” I asked.</p><p>Naomi was on her back at that point. She stared up at the ceiling and smiled as she said, “Yes I was.”</p><p>I still remember how happy that moment made me. The whole night had been a strong confirmation that I was actually going to end up being cuckolded, but that felt like the strongest. She’d just cum and she was gleefully admitting that she’d been thinking of another man. There wasn’t a hint of shame. She’d embraced the idea fully.</p><p>As you’ve probably already guessed, Naomi did cuckold me. She has a boyfriend, in fact, and it’s been an insanely thrilling experience. Next time I’ll tell you about how that relationship got started.</p>