How to Teach Your Cuckold the Joys of Anal Play

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This guide is written under the assumption that you like the idea of your cuckold submitting to anal penetration. That you like the idea of him taking your fingers, a dildo, a strapon, or even your bull’s cock up his ass. If that’s not for you, I’ve written many other articles you might find useful.

For the rest of you, there’s a certain pleasure in the idea of your cuckold getting fucked. Maybe it’s because you know he’s bisexual and you want to let him explore that pleasure. Maybe it’s because there’s nothing hotter to you that your straight husband submitting to bisexual play for your pleasure. Maybe it’s just because you’re both into exploring ass play or because doing something kinky feels good.

What the reason, the pleasure is real and it’s worth exploring. What follows is a guide that will help you explore the joys of anal penetration with your cuckold, starting from the most basic play to full-on bisexual penetration with your bull, though of course you’re free to take it only as far as you’re comfortable.

I’m going to start under the assumption that your cuckold husband isn’t wild about anal play. If yours is, feel free to skip to the next section.

Step One: A Little Anal Teasing to Excite Your Cuckold

This first stage is about exploring your cuckold’s level of interest in anal play (if you know he’s already interested, you can skip ahead).

You need to know if he’s eager or if he’ll need a little convincing. Thankfully, you can follow the same path no matter his level of interest. It just might take a little longer if he’s reluctant to surrender his asshole for your pleasure.

You can begin your exploration with your fingers. Take your cuckold to bed. Lure him into a state of arousal, ideally after another man has fucked you. Kiss him. Stroke his cock. Tease him. Get him to a place of intense lust.

Tell him to masturbate. Play with his balls and whisper into his ear about how good it felt to have your bull’s cock inside you. Listen to your cuckold moan. Run your fingers over his taint – that strip of flesh between his balls and asshole – and moan like you’re turned on to touch that spot.

Watch him as he nears his orgasm. When he’s close, let your fingers wander a little further south. Rub them over his asshole. Moan. Nibble his earlobe. Kiss him. Let your tongue slip into his mouth.

You’re just rubbing his asshole here. You’re not penetrating him. That’s too far for the first time. You really just want to stimulate all those nerve endings around his anus. You want to enhance the pleasure his masturbation is bringing him.

You can work in a little dirty talk to make it hotter, too:

“Does that feel good, cucky? Do you like it when I play with your tight little asshole?”

Utter those words in a lusty voice and he might very well cum. You see, your cuckold is almost certainly kinky and far more open to a wide range of pleasures than most men. He just needs a little help to fully embrace the joy of sexual exploration.

Scarlett is a beautiful seductress determined to make her husband into the bisexual cuckold of her fantasies. Through orgasm denial and sensual teasing, she convinces him to dip his toe into bi play, starting with a toy and moving on to a man.

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After the first time, you’re going to repeat that basic process numerous times, unless of course you’re absolutely certain your cuckold is so into anal play that he’s more than ready to move on to the next step.

If he’s not, though, you get to have fun getting him ready for that next step. It doesn’t have to be with him masturbating while you whisper into his ear, either. There are lots of ways to play with his asshole while making him cum:

• In a 69 – You’re on top. Your pussy is on his face. His tongue is working your clit. You’re stroking or sucking his cock. As he nears his orgasm, let your finger wander between his ass cheeks. Rub his asshole a little. Moan for him. Make him cum as you indulge in a bit of light anal play.
• Fucking in Girl on Top – You’re on top. His cock is inside you. You can see that he’s nearing his orgasm as you near yours. You lean back. You reach down. Your fingers find their way to his asshole. You rub it while he cums inside you. If you fail to cum, have your cuck use his mouth or fingers to get you off.
• Fucking in Missionary – You’re on your back. Your cuckold is inside you. He’s fucking and kissing you. You grab his ass. You spread his cheeks. You reach between them and give his asshole a good rubbing while he cums.
• After He’s Watched You Cum with a Vibrator – You masturbate together. You with a vibrator and him with his hand. You tell him not to, cum, though. He watches you get off. You talk dirty about how you wish your bull was there to fuck you. Then, when you’re done, you roll next to your husband and vibrate his asshole with your toy while he cums.
• While You’re Giving Him Head – If you give your cuckold blowjobs, you can very easily stimulate his asshole when he’s about to cum. It will make his orgasm even better.

The duration of the first phase is up to you. Ultimately, you’re trying to associate his pleasure with anal play. You want to get him to a place of comfort for the next stage, which involves penetrating him for the first time.

Step Two: Your Cuckold’s First Anal Penetration

Teasing his asshole is the appetizer. It’s actually penetrating him that will begin to change things for your cuckold.

It can be a special moment for a hotwife, too, especially if her husband is resistant to the idea of receiving anal sex. When you first penetrate him – even if it’s with just the tip of your finger – it can be hugely erotic as he’s engaging in an act of beautiful submission as he puts your needs above his own.

The first time can happen with your fingers, a plug, or a sex toy. I’d recommend you use your fingers or a toy, and I’d lean towards a toy. You’ll have a better feel doing it with your fingers, but to be honest, it can get a little bit messy and it’s easier to clean a toy.

You want him massively aroused the first time you penetrate his ass. Thankfully, you should be aroused, too. There should be lots of kissing and dirty talk. There could be sex if you want. Just don’t let him cum. I’d recommend you work in some dirty talk about your bull so he’s in a cuckold’s state of mind by the time you penetrate his asshole.

It’s also worth utilizing lube in this situation, so add some to his cock. Add plenty. Lube his cock and his balls and let some of it drip down to his asshole. Even rub it around with your fingers while you’re down there, making everything nice and slippery.

Then comes the toy. You’ll want a fairly slender vibrating dildo for the first penetration. Make sure it’s on – though not vibrating at too fast a pace – and then rub it around his crotch. Rub it over the head of his cock. Rub it over his balls. Rub it over his inner thighs and his taint. Move it towards his asshole. Watch as he lifts his hips.

Whisper softly, “Does it feel good when I play with your asshole, cuckold?”

Listen to him moan. Watch him lift his hips just a little to give you easier access.

Kiss his neck and say, “I love watching you stroke your cock. I love how hard you are. I love how much it excites you when I play with your tight little asshole.”

Press the tip of the dildo against his anus. Apply gentle pressure. Watch his face. If you see pain, pull back. You shouldn’t, though. You should see pleasure. You should see him enjoying the fact that his wife has just penetrated him for the first time.

You might see a bit of discomfort. You can counter that with soft kisses against his neck and sensual moans that make it sound like you’re on the verge of an orgasm.

You can say, “I’m inside you, baby. I’m in your ass and it turns me on so much.”

Even if there’s discomfort, it will likely abate the longer you’re inside him. So keep the toy in him. Move it in and out. Do so slowly. Fuck him. Fuck your cuckold husband. Fuck him while he masturbates. Show him the utter joy of anal penetration.

Make sure he cums with your toy in his ass. Make sure you’re moaning. Make sure you’re talking dirty to him. Make sure you’re expressing how much you love that he’s willing to let you fuck him.

Once he cums, pull the toy out, set it aside, and shower him in lusty praise. Tell him how hot it was, how much you love him, how much it turned you on to be able to fuck him while he masturbated.

If you’re up for it, sit on his face and let him lick you to an orgasm. Let him feel how wet you are. Show him that the arousal is real and let him feast on it.

Now that you’ve penetrated him for the first time, you can begin to explore anal sex with your cuckold just a bit more. Don’t jump right to a big toy or your bull’s dick yet, though. He’s nowhere near ready for that.

Instead, you can try:

• More Toy Play – Use that same slender vibrator again and again. Don’t do it every time he cums, but work it in every now and then.
• Introduce Your Fingers – Again, this can be a bit messy, but if you wear a condom or a glove, fingering his ass can actually be a little more intimate. Plus, you can use your fingers to find his prostate and provide extra stimulation in that way.
• Enemas Before Play – Once he’s gotten used to the idea of anal penetration, you can have him start cleaning his ass before you play. It doubles as a way for him to surrender his ass to you as he’s effectively cleaning it out so you can use it.
• Butt Plugs – You can buy a set of plugs that get increasingly large and work your way through them, starting with the smallest. Sliding a plug into him before a quick trip out can be really kinky. Putting it in while you’re having sex is also exciting as you can play with the plug while your cuckold’s fucking you, thus adding anal stimulation to his pleasure.
• Have Your Cuckold Fuck Himself – If you’ve established that anal with your cuck arouses you, perhaps he’d be willing to use the toy on himself while you watched. You can masturbate while he does it, showing him that his anal submission is more than enough to give you an orgasm, or at least get you all worked up. Plus, there’s a very good chance he’ll enjoy putting on a show for you.

This step is likely to last for quite some time as he needs to get used to having toys up his ass and he needs to wrap his mind around the idea of becoming someone that indulges in receiving anal pleasure.

You’ll have to judge when he’s ready to move on to the next step – which is bigger toys and more overt penetration – but before that there’s a bonus step I recommend you engage in if possible.

Bonus Step: Associate Anal Play with His Cuckolding

This is most useful if your end game is to see your bull fuck your cuckold, but it’s also a great way to further differentiate between your husband and the man that satisfies your sexual desires.

Pick out a plug before your bull arrives. You can go with something that’s a touch humiliating if you like, such as a butt plug with a jewel at the end that sticks out of his ass. It looks pretty and a little bit feminine and there’s a chance your cuck will find it thrilling to wear.

Once you’ve picked out the plug, have your cuckold strip and bend over the bed. Have him reach back to spread his ass cheeks and then squirt a little lube on the toy and on his asshole.

Say, “I love that you’re letting me plug your ass while my bull is here, cucky. I get so turned on at the idea of my husband’s ass being stuffed with a nice thick plug while another man fucks me.”

Listen to him moan as you rub the tip of the plug over his asshole. Slowly work it inside him. Fuck him with it a little bit. Use it to remind him of his place.

Say, “It feels like the right thing for a cuck’s ass to be plugged while another man fucks his wife, doesn’t it?”

He’ll say ‘yes.’ Of course he will. He wants to make you happy and he can hear the arousal in your voice.

Once you’re done, give his ass a good smack and then kiss him. Make it a long, lingering kiss. Involve your tongue. Pull him close. Feel him get hard. Grab his ass, spread his cheeks, and wiggle the toy while your tongue explores his mouth.

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Make sure he wears the plug all night long. It will depend on your bull’s willingness to play along, but you could have your cuckold show off the plug while you both admire it, or humiliate your cuck for wearing it. How you engage with that sort of fun depends entirely on the nature of your relationship and what sort of humiliation your cuckold is eager to receive.

If you have a chastity cage you could lock your cuck in it. Doing so would assert your control over both his cock and his asshole while another man gets to slide into your pussy and fuck you as hard and long as he likes, hopefully giving you multiple orgasms in the process.

If you’re into anal play, there’s little reason not to have your cuckold plugged every time you and your bull meet up. You could also plug his ass while you’re on a date and he’s at home, or while you’re staying overnight at your bull’s.

Step Three: Bigger Toys and Strapon Sex

Learning to enjoy anal sex is all about patience. His asshole needs time to adjust to being fucked, which means you both need to exercise patience.

If you plan on fucking him with a strapon or having him take your bull’s cock, you’ll have to slowly increase the size of the objects entering him. Luckily, you can be honest with your cuckold that you’re training his ass. He’ll probably like that. He’ll like the sense of submitting his ass to you, of his wife taking control of some part of him.

If you bought a set of butt plugs of increasing sizes, use those on a regular basis and keep moving up. Show him how happy you are each time he upgrades. He might even take to training his ass on his own if he’s rewarded with praise, the chance to worship your pussy, or an orgasm.

You should increase the sizes of the toys you use on him, too. Find dildos that are thicker. Stretch him with them. Fuck him with them. Make him cum while you’re fucking him with them. Make it so that he gets off on receiving anal sex from his wife.

If you’re keen on him being a bisexual cuckold, purchase a toy that looks like a cock. They come in all sizes, so you can start with something smaller. You can have your cuckold suck on it to get it lubed with his spit and then you can slide it up his ass and fuck him while you stroke his cock and tell him how much you love seeing him take cock.

The strapon sex (or pegging, if you prefer) is the most significant part of this step. It may not feel that different, but it really is. It represents a complete role reversal and a significant power exchange and there’s intense pleasure to be found in that.

There are numerous vibrating strapons now available on the market (such as Strapon Me) and I’d recommend trying one of those to start as they’re damn near guaranteed to make you cum while you’re fucking your husband’s ass.

Find yourself a strapon you like. Have your husband strip naked and then let him watch as you put on the dildo you’re going to fuck him with. You could even have him dress you in it, which would be quite the trip.

Once you’re ready, lube your cock while he watches. It will be hotter if he’s on his knees and looking up at his wife as she strokes her dick. If you’d like, you can have him suck it a little before you lube it.

For the first time, I’d recommend fucking him while he’s on his back. He’ll feel vulnerable – which is what you want – and you can easily stroke his cock while looking into his eyes and connecting with him as he experiences an entirely new kind of anal sex.

Lube his hole. Make sure your cock is lubed. Gently work yourself inside him. Make him take your cock. Be gentle about it, but make him take it. If you bought a vibrating strapon, make sure it’s turned on and offering you both pleasure.

Once you’ve filled him, lean down and kiss him while he gets used to the size of your cock in his ass. Let your tongues dance and move your hands through his hair and over his body. Encourage him to caress you, too. To grab your ass. To play with your breasts.

Then you fuck him. It’s hottest if you start fucking him while you’re kissing, just like when he has missionary sex with you. You’ve completely reversed roles. You’re the one doing the fucking. You’re taking his ass. You’re making him submit to your cock. You’re having anal sex with your husband and the vibrating strapon is likely ensuring that you feel really fucking good while you’re doing it.

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Say, “It feels so good to fuck you, baby. It feels so good to fuck your tight little ass with my cock. It feels so good to make you take my dick, to make you take it so deep in your ass.”

If he’s moaning, fuck him faster. Fuck him harder. Fuck him like he’d fuck you. Fuck him like your bull would fuck you.

You want to make him cum, though, so at some point you’ll have you to lean back and take hold of his cock. You could also have him scoot his ass forward until it’s hanging over the edge of the bed and fuck him while you’re standing and jerking him off.

Either way, fuck him, stroke him, and time it so that you both cum at the same time. Jerk his cock and make him cum all over his stomach while the vibrating strapon gives you a fantastically pleasurable orgasm.

Then, collapse on top of your husband while you’re still inside him. Kiss him. Tell him how much you enjoyed fucking him. Thank him for being willing to take your cock like a good boy.

If you want to mix it up, you can fuck him doggystyle. You can get a little bit rough and aggressive and dominant. You can smack his ass and pull his hair and call him names if you’d like. You could also just pound him from behind until the vibrations make you cum. You can give him a reach around if you like or you can just make him take it if it turns you on to do so.

Many cuckold and hotwife couples are happy stopping there and simply working anal penetration into their sex lives. If that’s you, then enjoy exploring the many ways you can make your cuck give up his asshole for your pleasure (and his pleasure, of course).

If you want more, move on to the next step.

Step Four: Have Your Bull Fuck Your Cuckold

For some hotwives – especially those with a dominant streak – this is the pinnacle of pleasure.

If you’re one such hotwife, you know that there’s nothing hotter than the thought of your cuckold husband getting on his hands and knees and submitting his asshole to your bull. It makes you wet to imagine your bull mounting your cuckold and sliding into his ass from behind. It makes you want to masturbate as you imagine your bull’s fingers digging into your cuck’s hips while he pounds his ass in pursuit of an orgasm.

Some cuckolds will refuse and you should respect that if yours refuses. Many will happily do what their wife desires, though. If you’re lucky enough to be with a cuckold like that, take full advantage.

Inform him beforehand that your bull will be fucking him (the idea of a surprise might be sexy, but it might also feel like a betrayal to your cuck and wouldn’t be worth it).

Make it very clear that the idea turns you on. In fact, try your best to introduce it while you’re fucking your cuckold’s ass with a strapon. Say, “Mmm, baby, I can’t stop thinking about my bull being the one to fuck you. I’m thinking about it right now, actually, and it’s making my pussy so wet. I just keep thinking about his cock in your ass, about him pounding you from behind. about him cumming while he puts my cuckold husband in his place.”

When your bull arrives, serve everyone a drink. Have your bull sit on one side of you and your cuckold on the other. Kiss your bull and then kiss your cuckold. Stroke them both through their pants. Tell your husband that you can’t wait to see your bull fuck him. Let them both finger you to see how wet you are. Make sure everyone is aroused by the time you go to the bedroom.

Strip your cuckold naked while your bull takes off his clothes. Be as intimate as possible with your husband. Kiss him. Let him touch your body. Let him worship your breasts a little.

Ask him, “Are you ready to get fucked, cuckold? Are you ready to let my bull have your ass?”

When he answers ‘yes,’ have him get on his hands and knees in the bed. Let him watch as you suck your bull’s cock until he’s hard as a rock and wet with your spit. Let your cuckold watch as you roll a condom down your bull’s cock.

Say, “I can’t wait to watch you fuck my husband.”

Grab a bottle of lube. Generously coat your husband’s asshole. Prepare him to be fucked by a man.

Have your bull approach and crawl into the bed. Run your fingers over your cuckold’s ass and then grab your bull’s cock and guide the tip to your husband’s anus. Rub it around, Do it slowly. Take your time. Reassure your husband that you’re insanely aroused.

Have your bull push the tip inside your cuckold. Have him penetrate him. Have him fill him. Just an inch. Just the tip. Listen to your cuckold’s moans. Rub your hand over his lower back and his ass cheeks. Tell him how much you love him. Tell him how wet you are. Tell him how hard you’re going to cum as you watch him get fucked.

Now move in front of your husband. Spread your legs. Let him see your wet pussy. Play with it. Masturbate. Finger yourself vigorously while your bull slowly works his cock into your cuckold’s asshole.

Let your husband suck your fingers clean. Push them in and out of his mouth. Fuck his face while your bull fucks his ass.

Lean in and kiss him. Push your tongue into his mouth. Moan for him.

Whisper, “I’ve never been so wet, cucky. Watching him fuck you…it’s the hottest thing I’ve ever seen. Will you eat my pussy while he fucks you? Will you eat your wife’s wet cunt while my bull has anal sex with you?”

He’ll nod. Lie back. Spread your legs. Let your cuckold feast on your pussy while he gets fucked.

Tell your bull to fuck him harder. Tell your bull to use your cuckold’s asshole for his pleasure. Grab a handful of your husband’s hair, lift your ass off the bed, and rub your wet pussy all over his face as he gets pounded from behind by your bull.

Try and cum with your bull. Try and make it happen at the exact same time. Let your cuckold experience the joy of making two people climax simultaneously.

Say, “Baby, I’m close. Watching you get fucked has me close. Eat my pussy. Eat my pussy while he fucks your ass. Eat my pussy and make us both cum, cucky!”

Orgasm with your bull. Cum on your cuckold’s face while your bull is getting off with his dick buried deep in your husband’s asshole.

Enjoy your orgasm. Lie back. Kick your legs open. Play with your tits.

When your bull pulls out, invite your cuckold to crawl on top of you. If you have energy for it, let him inside you as a reward for getting fucked. Let your cuckold fuck you. Let him cum inside you. Let him enjoy the reward of being a good boy and taking a wondrous anal fucking.

There you go. You’ve done it. Your cuckold is into anal sex. He might even love it. He might be willing and eager to do it whenever you’re in the mood.

Even better, you’ve just added a whole new wrinkle of pleasure to your sex life, ensuring that neither you nor your cuck will ever get bored. What could be better?

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