If you want to follow the evolution of a first time cuckold as he delves deeper and deeper into his fantasy with his wife and her bull, visit my Patreon page to read ‘Your Cuckolding‘, a multi-part story that takes you on the entire erotic journey.
Now, on to the story of how your first cuckolding might go:
You’ve fantasized about this for years. Decades, even. You’ve had countless orgasms while picturing your beautiful wife cumming on another man’s cock (his much bigger cock, in all likelihood). Even a fleeting thought of being cuckolded is enough to excite you.
Now it’s about to happen. You’re on the verge of being cuckolded for the first time. Your wife’s already been on a few dates with the man who’s going to cuckold you. They’ve kissed. They’ve done a little heavy petting. She’s played with his cock a little, but only over the pants.
Tonight, though, they’re going all the way. Tonight, he’s going to fuck her. He’s going to fuck your wife and she’s absolutely going to have a world class orgasm with his big cock buried deep inside her wet, needy, married pussy.
Preparation for Her Date
The night begins before she leaves for her date. It begins in the shower. She’s kind enough to let you join her so you can wash her hair, soap up her beautiful body, and shave her pussy exactly as she wants it to be for him. In this case, that means getting on your knees in the shower and carefully removing all the hair with the exception of a delicate strip above her pussy.
After the shower, you carefully dry off your beautiful wife and apply lotion to her long, sexy, freshly-shaved legs, leaving her skin soft and shiny. She’s kind enough to allow you to worship her pussy for just a bit. As you do so from your knees, your wife reminds you that another man will be satisfying her pussy that night and that his cock is impressively large.
When you’re finished, she asks if you still want to be cuckolded, that you can still back out. You give the idea serious thought, for despite your excitement, you feel nervous. You’re not wrong to feel that. Welcoming another man into your marriage – and make no mistake, that’s what you’re doing, even if he only fucks your wife once – is a big deal.
You want it, though. You’ve craved it for years. You want to be cuckolded for the first time and you want it to happen many times after that.
She smiles, leans down to kiss you, and instructs you to pick out a matching bra and panty set for her. She wants to look good when her date takes off her dress. She wants to be so enticing that he can’t help but feel an overwhelming desire to fuck her. As you leave the bathroom, she instructs you to add stockings and a garter belt so she can be as sexy as possible.
While you pick out her lingerie, your wife does her hair and makeup. She takes her time – more time than when she does it for a date with you – and after you’ve selected her underwear for the evening she asks if you’ll tidy up the house since she wants it to look good when she and her date return.
You clean the house as instructed and the entire time your head is filled with imagery of your first cuckolding. You wonder if they’ll fool around on the couch before going to the bedroom. You wonder if your wife will let you watch or if you’ll be relegated to listening as your cuckolding unfolds. You wonder if she’ll give him a blowjob and if he’ll go down on her. You wonder if you’ll be allowed to participate in any way.
Your wife calls you back to the bedroom. She’s wearing the lingerie and a pair of heels. She turns and smiles at you. Her hair and makeup look perfect. Her lingerie looks perfect. Your cock stirs to life. You feel desire for her. You suddenly crave her. You feel jealous as you grapple with the notion that she’s put in a great deal of effort to look incredibly hot for another man.
You tell her she looks sexy, that she looks beautiful, that he’ll want her like no man has ever wanted a woman. She beckons you into the room and you share a tender kiss with just a hint of tongue. It’s enough to leave your cock stiff. She asks if you still want to be cuckolded. You tell her you do. You express that you’re nervous about it, but the excitement you feel overwhelms that nervousness.
She tells you her dress is hanging on the back door of the closet and asks if you’ll retrieve it for her. You rush to the closet and stop when you see that she’s picked out your favorite dress, only she plans on wearing it for another man. It’s a low cut red number that emphasizes her spectacular breasts, is tight at the waist, and has a flared, almost pleated bottom. It’s short, too, and when she’s in heels her legs look breathtakingly sexy in it. You’ve never seen her in the dress while in stockings and you’re certain it’s going to look stunning.
She asks if you’ll help her into it. You take it off the hanger. You unzip it. You hold it low so your wife can step into it. You pull it up her lithe, beautiful body and zip it up. You brush her hair aside and kiss the back of her neck. You look at her in the mirror and imagine her date standing behind her like you are. You imagine his lips on her neck. You imagine his hands on her waist. You imagine him unzipping her dress and revealing her body in the lingerie you picked out for her.
Your dick is hard as a rock and your heart is pounding as all of that drifts through your head. You feel jealousy and a bit of angst alongside your arousal. You’re fairly certain those feelings will stay with you for the rest of the night.
It’s time for her to go. A car pulls into the driveway. Your wife asks once more if you still want to be cuckolded for the first time. She doesn’t say so, but it feels like your last chance to back out. You tell her you still want it. You tell her she looks beautiful. You tell her he’ll find her irresistible.
She gives you a soft kiss on the cheek and walks out the door. You watch as her date gets out of the car. Your wife steps into his arms and they share a kiss. Your cock stirs and your heart pounds as you witness what seems to be intense desire between them. It’s not just a quick peck on the lips. It’s a passionate kiss.
His hands move down her back and he gently grabs the top of her ass. She runs her fingers through the hair on the back of his neck. You’re certain their mouths open and their tongues mingle. It’s not the first time they’ve kissed like that and it makes you feel as though you’re guaranteed to be cuckolded that night.
He takes her to the passenger side of the car, kisses her once more, and opens the door for her. Your wife gets in and soon enough he’s backing out of the driveway. Just like that, they’re gone. Your wife is on a date with another man. It’s not her first date with him, but it’s the first time that you’re certain it’s going to end with your cuckolding.
This is the hardest part. Without anything to focus on, your imagination runs wild. You have plenty of time to wonder if you’ve made a terrible mistake, if you should have taken the opportunity to back out when your wife gave it to you. You wonder if you’re going to lose her. After all, there’s a very good chance he’s going to fuck her better than you do, and if that happens, wouldn’t she at least consider leaving you to be with him?
You tell yourself that’s nonsense, that it’s just sex she’ll be having with him, that she loves you deeply, that she wouldn’t leave you. It’s all true, but you still worry. You still feel the angst. You can’t help it.
You tidy the house again. It doesn’t need it, but you need something to do. You make sure the bedroom looks perfect. You check to make sure that the condoms you bought for this occasion are still in the nightstand drawer where you left them.
Forty five minutes after they left, you receive a picture from your wife. She and her date are sitting side by side at a restaurant. He has his arm around her. They’re both smiling. They look joyful. They look like a couple and they definitely had someone else take the picture.
The picture turns you on, but it enflames your angst, too. Your wife looks like she’s out with her boyfriend, like she’s part of a couple with another man. Part of you wants to masturbate and part of you wants to run to the restaurant to tell her that you made a mistake, that you want your first time as a cuckold to end before it even begins. Those conflicting feelings will likely be your constant companion as a cuckold, for there’s an inherent risk in bringing another man into your marriage, a risk that even the most loving couples can’t entirely negate.
You receive a few more pictures over the course of the evening. One is a selfie of your wife and her date sharing a kiss. Another is of him feeding her a spoonful of a delicious-looking dessert. Another is of her offering a seductive-looking kiss against his neck while he smiles at the camera.
Each picture turns you on and leaves you filled with angst. You walk around the house looking for something to do but there’s nothing that will distract you from the increasing sense of nervousness that envelops you. Of course, you feel that telltale tingle of desire between your legs, too. You keep going back to the pictures. You keep looking at the one of her kissing his neck, at the obvious desire on her face as she does it. Your wife wants him, and that turns you on in a way you’ve never been turned on.
Her Return Home
Eventually, your wife texts to let you know she’s coming home. Immediately the arousal and angst increase. You rush to the bedroom to make sure it’s ready for their arrival. You tidy the house once more as you wonder if you’re about to experience the greatest thrill of your life or if you’re about to ruin your marriage.
A car pulls into the driveway. Your wife and her date get out. He takes her hand and they head to the front door. You’re not sure what to do, so you decide to open the door for them.
Your wife smiles and so does her date. They step inside and he shakes your hand as she introduces you. He’s a little taller than you, his shoulders are broader than yours, and he’s unquestionably good-looking. He’s well-dressed, too, as he made just as much effort as your wife to look good for their date.
Without thinking, you ask if you can get them both a drink. They accept and you head to the kitchen to open a bottle of wine. You pour three glasses and return to the living room. Your wife and her date are sitting side by side. His hand is on her leg. His fingers are moving in slow circles over her thigh, just above her knee. She’s looking at him and you can see a sense of adoration in her eyes. She leans in and they kiss as you set their glasses on the coffee table.
For a few moments you stand there and watch as your wife kisses another man. You study her soft lips as they part. You see his tongue move into her mouth and you hear her moan. You see his fingers move up her leg just a little and watch as she rests her hand on his thigh, suggesting her desire to touch his cock and confirm his desire for her.
She looks at you and you realize how awkward it is to be standing in the middle of the living room with half an erection in your pants. You sit on the loveseat across from them. Your wife and her date pick up their wine glasses and share a quick toast.
A conversation unfolds. Her date asks how long you’ve been together and how you met. He asks about your interest in cuckolding. You ask if he’s ever been with a married woman before and he confirms that he has. He goes on to say that the best sex he’s ever had is with married women, that he finds it particularly appealing if the woman’s husband is watching as she cums with his cock inside her.
His desire to be the man that cuckolds you for the first time proves to be more thrilling than you imagined. It helps to calm your nerves, too, as it seems that he has no interest in taking your wife from you. In fact, at least some of his interest in her is precisely because she’s a married woman and that she’s cuckolding her husband.
Your wife asks if you want to watch another man fuck her. She follows it up by asking if you want to watch her cum with another man’s cock deep in her pussy. Excitement courses through you as she asks. You answer affirmatively. You want your first time to be as thrilling as possible, which means you want to witness your cuckolding.
The Foreplay Begins
The conversation continues until they’ve finished their wine. Then your wife sets their glasses on the coffee table and kisses him. She does so passionately. She sucks his tongue into her mouth. She moans and her hand moves between his legs. The foreplay has officially started. She strokes his cock through his slacks. You see the outline. He’s hard and he’s quite large. He’s larger than you, in fact. That excites you, though. You’ve always fantasized about your wife fucking a man with a much bigger cock than yours.
His hands roam as they fool around. He plays with her tits. He slips his fingers into the top of her dress and squeezes her soft flesh as she moans into his mouth. He runs his hands up her stocking-clad inner thighs and she spreads her legs, inviting him to press his fingers against her panties and rub her pussy, eliciting yet another moan.
You lean forward as she unzips his pants. You feel the buzz of the wine coursing through you. You watch your wife’s fingers slip into his fly. You hear him moan as she finds his cock. It takes a little doing – he’s quite large, after all – but eventually she frees him. Her fingers move up and down his shaft as you stare at it. You’re utterly mesmerized. It’s long and thick and, most importantly, it’s going to end up inside your wife before the night is over.
She moves to her knees on the couch and her head drops into his lap. She closes her eyes and takes his cock in her mouth. She moans and you do the same. Your wife is sucking another man’s cock in your living room and it’s the most beautiful thing you’ve ever seen. Your cock is hard. Hard as a rock. Your first cuckolding has begun to unfold and judging by the eagerness of your wife’s blowjob, it’s going to be a spectacular night.
He groans, tells her how good her mouth feels, and runs his hand down her back. He pulls up the bottom of her dress, gives her ass a playful smack, and grabs a handful of it. He squeezes hard and she moans while taking half his length in her mouth. Her head bobs up and down in his lap. The sounds of the blowjob get louder as she coats his shaft with her saliva. She wraps her fingers around him and her hand moves in concert with her mouth.
You marvel at how eager your wife is to pleasure her date. You feel a touch of angst as you realize that she hasn’t given you a blowjob like that in a long, long time. You can’t help but assume that she feels greater desire for him than she’s felt for you in a long, long time. Your angst deepens, but so does your arousal. That’s the nature of being a cuckold, after all. It works best when your wife feels overpowering desire for another man.
She looks at him while stroking his cock. She tells him she wants him inside her. She tells him she needs him inside her.
Then she looks at you. She asks if you’re ready to be cuckolded for the first time. You nod and tell her you’re ready. You tell her you’re eager.
She gets up off the couch. She saunters towards you. You stand. She takes your hand and places it between her legs. She tells you to feel her cunt. You pull her panties aside and slip your fingers inside her. You’re engulfed in the heat and wetness of her utterly perfect pussy.
She tells you she wants him, that she’s desperate to feel his big cock in her pussy. She tells you she can’t remember the last time she was so turned on. She strokes your cock through your pants as she says it, engulfing you in arousal.
Then she asks if you’re absolutely certain you want to be a cuckold. It’s kind of her to give you another chance to back out, but you can’t. You’re far too turned on for that. You tell her that you want it. That you crave it. That you can’t remember the last time you were so turned on.
Your First Time as a Cuckold Truly Begins
She pulls your fingers from her pussy, removes her panties, and turns towards her date. He gets up off the couch and they walk hand-in-hand towards your bedroom. Your heart pounds harder than it ever has as you follow. You step into the bedroom and see him unzipping your wife’s dress. You watch it fall to the floor. You see him kiss her neck before she steps away, spins around, and lets him admire her body in the lingerie you picked out for her.
She approaches and they kiss as she undresses him. She kisses his muscular chest the moment it’s exposed and he takes his shirt off as she works his belt and unbuttons his pants. Soon enough another man is naked in your bedroom.
Your wife expresses her desire for him. She tells him she wants him, she needs him. She tells him that she wants him to fuck her. She tells him that she wants him to cuckold you.
Your wife asks where the condoms are. You tell her they’re in the nightstand. She smiles at you but does nothing. You take the hint and open the nightstand drawer. You pull out a condom and hand it to her. She thanks you, tears open the condom, and he steps closer to the bed so she can dress his cock. They kiss as she rolls the rubber down his thick shaft. She moans into his mouth as he fingers her and plays with her perky tits in the delicate bra you selected.
Your wife gets in the bed. Your marital bed. He gets in with her. He moves between her legs. He runs his fingers up her stockings and over her stomach and grasps one of her breasts. The head of his cock moves over her pussy lips. You’re moments away from being cuckolded. Your first time has exceeded your expectations so far and you’re certain it’s only going to get better.
They kiss as your wife reaches down and grasps his cock. She guides the head inside her. She moans as he slowly fills her pussy. Your cuckolding began the moment you stepped into the shower with her, but this feels like the moment of truth. This is when everything changes. A boundary has been crossed. Another man is inside your wife. He’s moving in and out of her pussy. She’s moaning as she runs her hands down his back and grabs his ass. Pleasure envelops both of them while you stand there and watch his cock move in and out of her.
Your wife tells him how good it feels to have his cock inside her. She tells him to fuck her harder. He picks up the pace. He delivers more strength with each thrust. You watch with a perfect view of his cock filling her. You see her hands grasping at his ass and moving up and down his muscular back. Your dick is hard as a rock.
It’s clear your wife is going to cum quickly. It’s clear she’s going to cum loudly, too, and that he’s going to make her cum harder than you do. You feel the angst. You feel the pleasure. Another man is fucking your wife better than you do. She’s overwhelmed with pleasurable sensations as his big cock reaches places in her pussy that you’ve never reached.
She announces she’s cumming. You haven’t moved from your spot. You haven’t pulled your gaze from the spectacle unfolding in front of you. Your wife cums on another man’s cock as you’re standing there with an erection in your pants. You see her pussy pulsing around his shaft. You see her thighs tremble. You hear her exultations of pleasure and you recognize that they’re different from the last time you fucked her to an orgasm.
She holds him close and they kiss in the aftermath of her orgasm. They kiss deeply, too. She tells him how hard he made her cum. She tells him his cock is so deep inside her. Then she tells him that he fucked her better than you do.
Your legs wobble a little. You’ve been cuckolded for the first time. You’re turned on. You’re filled with angst, too. Your cock is hard and your loins tingle a little. You’re a little lightheaded. You want to masturbate, but part of you wants to leave the room to take a deep breath.
He pulls out and rolls onto his back. Your wife straddles him and guides his cock into her pussy. She rests her hands on his chest and moves her hips back and forth, grinding on him and eliciting a moan of pleasure from the man who just cuckolded you for the first time.
Your Wife Makes Another Man Cum in Your Marital Bed
She asks if her married pussy feels good. He nods and affirms the pleasure she’s offering him.
Then your wife looks at you. She rides him as she meets your gaze. He reaches up to play with her tits in the bra you selected for her. She asks if you’re enjoying your first time as a cuckold. You nod. She asks if you enjoyed watching her cum on another man’s big cock. You nod. She asks if you want to watch your wife make another man cum while he’s buried in her pussy. You nod vigorously.
She turns her attention to her date. She tells him that she wants to make him cum. She wants to make him feel good. She wants to give him the same kind of pleasure he gave her. She tells him that she wants her tight little married cunt to make him feel good and that she wants to do it while her cuckold husband watches.
She’s into it now. She’s all the way into it. So are you. Somehow, it’s even hotter watching her on top. She’s working to make him feel good. She’s working him with the pussy that used to be yours. She’s playing to his desire to cuckold you and he’s clearly getting into it.
You watch your wife work his cock until they’re both in a frenzy of arousal. You rub yourself through your pants, getting closer to an orgasm of your own while their moans fill your marital bedroom.
They cum together. He grunts and groans in a deep, animalistic manner while cumming as he’s buried deep in her pussy. You watch your wife climax but your thoughts are focused on the beautiful pleasure of knowing that another man is cumming while inside her. You think of him doing so without protection. You think of him flooding her pussy with his seed and you very nearly cum in your pants at the notion.
She leans down and they share a deep kiss as his hands move up and down her back. She lifts her pussy from his cock and you see the load of cum at the tip. You stare at it. It’s proof that your wife made another man cum – that he came while inside her – and the sight of it is utterly intoxicating.
They share another beautiful kiss and he gets out of the bed and heads for the bathroom. He shuts the door and your wife tells you to undress and crawl into bed with her.
You do as you’re told and she presses her warm, lithe body against yours. She kisses your neck and takes your stiff cock in her hand. She asks if you enjoyed your first time as a cuckold.
You tell her it exceeded your expectations. She tells you it was the same for her. She asks if you want her to cuckold you again. You tell her you do. You tell her you can’t believe how thrilling it was to watch her cum with another man’s cock inside her and to watch her make another man cum.
She strokes you a little faster. She kisses your neck. She moans like she moaned for him. She tells you how good his cock felt in her pussy. She tells you how good he fucked her. She tells you how hard she came with his big dick buried so deep inside her tight little married cunt.
You cum. You cum all over your stomach. You feel the hot seed splash against your skin as a pleasure unlike any other courses through your body. It’s your first orgasm as a cuckold and in the moment it feels as though it’s far beyond any climax you’ve ever experienced.
You thank your wife for the orgasm and for cuckolding you for the first time. You tell her she’s amazing, that she’s so much more than you ever could have hoped for as a wife.
She asks if you want her to cuckold you again. The answer feels less clear in the aftermath of your orgasm – some of the angst has returned – but you tell her that you absolutely want to be cuckolded again. After all, you both had orgasms that exceeded the pleasure of anything you’ve experienced in recent years, and that’s the best reason to make cuckolding a part of your marriage.
Yes, there will be a great deal of angst in your future. That’s just how it goes for a cuckold. There’s even more pleasure to be had, though. So much more pleasure.