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Okay, so this Saturday it might actually happen. We’ve been invited to my brother-in-law’s birthday party—he’s turning 39.
What makes this party so interesting is that it’ll be the fourth time my wife (37) and I (40) run into her ex. He’s been friends with my brother-in-law since way back.
I have dozens of stories about why her ex is so fascinating to me, to her, and to our sex life over the past 15 years. By now we’ve gone through so many role-plays and fantasies, and we’ve even had a couple of real moments. I’m really hoping this time something might actually happen when we see Ryan (40) again. Kelly and he got together when they were 15 or 16—they were each other’s first.
Kelly and I have a great sex life. I give her lots of attention and know exactly how to turn her on or make her cum, but there’s one thing I’m not very good at and don’t really enjoy: long, really hard pounding until it hurts her or me. That’s what she sometimes needs, but it’s not something I can or really want to give. Don’t get me wrong—I give her good, hard sex. I’m not very small, I’m about 6 by 4.5 inches, and I definitely don’t cum too fast. I can make love, play, finger her, go down on her, and fuck in five positions for hours, but I can’t keep up more than ten minutes of nonstop, super hard thrusting. The harder she screams, the less I enjoy it—I don’t know why.
Early in our relationship, almost from the start, we started role-playing. Not full costumes, just taking on roles like the masseur, the doctor, the burglar, whatever. I quickly noticed that the moment something feels taboo or like it shouldn’t happen, she gets really turned on and soaking wet. Over the years we’ve perfected it. I only need to use a certain voice or line and she’s already horny. But there’s one thing we both get the absolute hottest from: her secretly fucking her ex Ryan and complimenting and comparing him to me during the act. We also flip my role sometimes—then she’s with me but telling me how much she loved her ex’s soft but already thicker and longer cock than mine when I’m hard. That big, thick head she used to get so wet from when she licked or sucked it.
Over the years she’s told me everything—literally everything—honestly. From him taking her virginity to the first time she fucked him after they broke up, when she already had a new boyfriend who was bad in bed.
Before she got with me, she had already decided Ryan had special qualities. Besides always being super fit, his dick was simply the golden formula for her. Soft and hanging already big, with a thick head and a slight curve in his long cock. His balls were maybe the most attractive part for her. She had five partners before me and always compared them to him. She’s not really a size queen, but there’s only one dick she’s had that, when she thinks about it, makes her wetter than normal and even seems to stretch her wider when I fuck her.
Over the years we’ve often fantasized about making certain fantasies come true. I’m not really a cuck, but the idea of her ex being better than me triggers something in me that’s simply too hot to describe. We have plenty of other fantasies too—it’s not our main thing, but it is our favorite one.
The fantasies we’ve discussed are all over the place. I think in the right setting she finds the idea of her ex the most taboo and exciting, but she could probably play just as well with someone else if we really wanted to make our cuck fantasy real. There’s no pressure from me on her to actually do anything or make a plan to get Ryan in bed, but I do challenge her every now and then.
Her reactions are different during the day than in the evening or when she’s had a drink, but last Friday at a barbecue with friends she brought up her brother’s upcoming birthday and Ryan being there himself, with a wink. That night in bed we had amazing sex where we played that she runs into her ex in her old room (her brother still lives in the house where she grew up). He’s secretly smoking a joint out the skylight. He’s wearing sweatpants and his bulge immediately catches her eye. They flirt a bit and she confesses she’s secretly been fantasizing about his cock for 15 years. He asks her why and she giggles and tells him that I—Joey—don’t satisfy her the way he could.
He pulls his pants down and she immediately drops to her knees, strokes his cock, kisses his head, and praises his dick and especially his manly, big balls. She looks at me so incredibly horny—I swear, at that moment it feels to her like she’s actually with Ryan. I know this from the completely honest stories she’s told me. He’s her best fuck ever. The best cock, the best head, the best balls, the best sex. She doesn’t see him as a partner anymore, but she does see him as a bed partner.
Then, when I (as Ryan) am fully hard, I fuck her as hard and long as I can while she keeps begging Ryan to go harder and deeper—this is to tease me. Right before I cum we switch roles. She climbs on top of me, kisses my face, and talks lovingly to me (Joey), telling me it’s okay that Ryan fucks her so much better and that I’m always allowed to reclaim her. She grabs my balls with one hand, sighs, and says it’s such a shame they’re so small and that she’s so glad she gets to fuck Ryan every now and then, which always makes me instantly fill her up.
After that we both get that post-nut clarity and drop the role. Until the next time we have sex, we don’t talk about Ryan again except for the occasional joke—always from me. Same thing this time. It was already late and we basically crashed after showering.
The next morning (last Sunday) something happened that doesn’t happen often. The kids slept in and we were awake before them, or at least Kelly was. I woke up while she was playing with my cock, which was already rock hard by the time I realized what was going on. I was happily surprised and asked her what she was up to.
She immediately slipped into a role. She looked at me and said, “It’s not enough, I can’t do anything with this. I’m so glad Ryan fucked me yesterday…” (she’s acting like our role-play from the night before actually happened). I was already hard but now instantly horny again. The post-nut clarity was gone and I was reset. I begged her to suck me or ride me. She refused sternly and already had a dildo ready (8 by 6 inches). She didn’t want Joey—she wanted Ryan and she wanted him now. She got into doggy-style position and demanded I fuck her with the dildo. I fucked her harder than ever, literally pounding that thing into her soaking wet hole. I pushed fingers into her ass—it didn’t matter, she wanted more and more. When she came screaming into the pillow and had caught her breath, she rewarded me in a way I’d never even thought of (though I’ve seen it in porn). She stayed in the role that I was just me and told me that if I wanted anything, I first had to lick her clean. Her pussy juice had never been so intense—I swear it looked like she’d been filled with a bottle of lube. I lay on my back, she sat straight on my face, and I licked her to a second orgasm while she literally jerked my cock. She held my balls roughly in one hand and pulled my dick so hard it felt like she was trying to stretch it bigger. I came so hard my cum literally hit the ceiling—that’s how horny and intense I finished from this scenario.
But right after, as always, that post-nut clarity hit us both.
Tonight after dinner, once the kids were asleep, I massaged her in bed and semi-seriously, flirting and teasing, brought up this Saturday and seeing Ryan again.
For now Kelly still finds it too exciting to actually do anything with it. She’s more than happy to just play it out in bed during role-play and says he’s an easy way for her to get in the mood. She does admit that if we ever actually make a cuck scenario happen, he would be the trusted one (it’s 100% certain she’ll never fall in love with him again, let’s assume that) and the most exciting and most taboo version that could happen. She herself mentioned that this coming weekend might be a chance to light the fuse with Ryan.
I find the whole thing super exciting and I honestly don’t really know how to bring it up. As far as I’m concerned she walks straight up to him, whispers in his ear that she wants to fuck him and that I want to watch, and asks if it can happen in 15 minutes. I’m the type to just go for it—long strokes, quick finish, that kind of thing. But Kelly isn’t really like that and she also sees the risks, plus she’s just a bit of a chicken about it haha.
How would you guys approach this or how have you guys done it?
* Update, (wrote this post yesterday but it did not get posted)
Today in the car we had some small talk, I joked about her wearing something slutty to the party. She asked me again you really want this huh? Don’t you think it’s better to stop this kidding around with her before she would either be really uncomfortable or crazy horny and wet all night. This tells me she is contemplating really doing something with it…. I feel butterflies in my stomach all day now
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