How Sex Toys Can Help You Fuck a Locked-Up Man

Some Keyholders are apprehensive about male chastity because they think it excludes penetration. But that’s not entirely true.

Can You Still Fuck While Your Man’s Locked Up?

Ah, sex toys. They are the answer to just about everything, aren’t they?

If you’re on the precipice of becoming someone’s Keyholder, you’re probably wondering what your sex life is going to look like in the future.

Sure, you’ve done the dance of negotiating the power exchange between you and your bottom or slave. You’ve dotted all the I’s and crossed all the T’s on the contract (or just had an in-depth conversation) that outlines how your chastity play will look. Still, first-time Keyholders are usually worried about the nitty-gritty of the actual sexual intercourse.

That’s especially true for couples who are trying out chastity and cuckolding as a lifestyle. Being a Keyholder or a Mistress is a brave endeavor and a great responsibility on your part. Yet no one can deny that it’s also immensely pleasurable.

Having a man submit to you so much that you’re the one who gets to say when he comes or if he comes at all is a fantastic rush. It’s almost indescribable. Still, that’s not the question on everyone’s mind today. So let’s get down to the dirty details — can you still fuck while your man is locked up?

Yes, You Can!

A cock that’s in a chastity device leaves a lot to be desired penetration-wise. There’s no denying it — there’s no way you can get satisfied by that sad lump of useless, caged meat.

And it really is useless, you know. The number-one reason men seek chastity devices and crave to be denied is that they know, somewhere deep down, that they can’t satisfy their partners (or anyone else). It’s a testament to their insufficient masculinity.

Of course, the reality is that there’s probably nothing wrong with them. These slaves are probably virile and capable as much as any other guy. But they feel like less of a man, unworthy or inadequate. They think and see that way in their heads (which is the only thing that matters). Thus, chastity.

Chastity devices don’t allow the man to get an erection (which he doesn’t think would be up to par anyway). Therefore, they also control and block his ability to masturbate and have traditional penetrative sex.

So their cocks will bring pleasure to no one, and they know it. Still, that doesn’t mean that they can’t pleasure and service their Keyholder/Mistress.

More than anything else, being aware of the power that the chastity keys give you and the fact that your partner is consenting to being entirely submissive to you is almost better than orgasming. But don’t worry — there are also orgasms in your future.

A man in a chastity device can use a wide variety of sex toys to give you what his flaccid good-for-nothing penis can’t — sexual pleasure!

Strap-Ons: For Him

There’s this ugly lie society as a whole perpetuates — strap-ons are just for women. That’s not only untrue but also a great disservice to everyone out there.

Our typically patriarchal society wants us to believe that men don’t need strap-ons since nature gave them cocks. But we know better, don’t we? Not all men have cocks that are worthy of entering us. Some men need all the help they can get.

Penetration — An Achievable Goal or Wishful Thinking?

Just because you have your subby man locked tightly away in a chastity device doesn’t mean he can’t top you. Well, top might be a strong word there, as there’s nothing in him that’s topworthy. But he can penetrate you, just not with his own flesh.

That’s precisely what strap-ons are for. Now, strap-ons are glorious devices, in more ways than one. They can contribute to your chastity play by not only giving you, the Keyholder, pleasure, but also by providing an extra layer of humiliation to your chastity bottom.

The strap-on highlights the fact that the man’s cock isn’t what’s going to satisfy the Keyholder. What’s more, it makes the man acknowledge the fact that he’s inadequate and lacking in specific fields.

Traditionally, men get pleasure from penetration. They come to expect it and crave it all the time. So making your sub fuck you with a strap-on and penetrate you while not getting any pleasure himself from an action that used to bring him immeasurable joy is almost cruel.

What’s more, he’ll feel all the sensations he usually does when it comes to sex — another body sliding against his, the sound of flesh slapping against flesh — everything, except for the grand finale. That feeling is reserved only for you.

The Best of Both Worlds — For You

Those who are working on long-term orgasm denial will be pleased to hear that strap-ons provide the best of both worlds. You’ll still be able to deny your man what he craves (an orgasm) while enjoying traditional penetrative sex.

A lot of women are fine with only receiving pleasure from oral sex. However, some don’t want to miss out on feeling a thick cock pounding them. And why should they? As the top in the relationship, they should be able to get fucked any way they see fit.

Which Strap-Ons to Choose

Of course, you’ll be the one to choose the suitable strap-on for your chastity play. After all, you’re not only the one who will feel it deep inside of you, but you’re also the dominant partner. Therefore, all decisions are yours to make.

Given that prolonged chastity and humiliation go hand in hand beautifully, we recommend you pick a sizable strap-on. There are a few reasons for that. Firstly, if you’re going to get a cock up in you, you might as well go all the way and get something substantial. However, more importantly, a big strap-on will serve as an exceptional point of comparison for your man in a cage.

Men can’t help but compare themselves to anything and everything. It’s because their frail male egos seek reassurance around every corner. So making him wear a huge strap-on will show him just how incompetent he really is. Sitting just above his small, sad caged cock, the strap-on will taunt him, ridicule him, and humiliate him splendidly.

Wearing a Strap-On Over the Cage

There are a few ways that a locked-up man can wear a strap-on to pleasure his Mistress and Keyholder. If you’re in a pinch, you can get just about any strap-on and go to town.

Regular Strap-Ons

Practically speaking, most strap-ons will fit both women and men (in or out of chastity devices). That’s a pure stroke of genius on the manufacturer’s side, as it does make choosing the sex toy in question quite easier.

Regular strap-ons are readily available, and you can fit them over, under, or above the actual penis. What’s more, because all of them have adjustable straps, they are a one-size-fits-all type of sex toy (but only when it comes to the actual harness).

Chastity Strap-Ons

There are, of course, strap-ons explicitly designed for men and those that are meant for men in a chastity device. We’d recommend choosing one of these since they fit not only the penis but also the fact that it’s in a non-erect, locked-up state. What’s more, they also accommodate (knowingly or otherwise) the fact that you want the flaccid caged cock to be visible so you can compare it to the strap-on.

Chastity-friendly strap-ons go over the cage and have a harness that fastens around the waist. Alternatively, the harness can also go around the man’s thighs, which means that you can position the dildo part of the strap-on anywhere you please — below or above the cage.

Most chastity strap-ons have a harness that extends around and behind the entire scrotum. That means that both the cock and the balls are nestled comfortably and safely in the strap-on and are on full display.

A chastity-friendly strap-on for men will allow the Keyholder to ride the man until she’s satisfied. That way, the Keyholder controls the pace, the depth of penetration, and the entire sexual experience. It’s another way of dominating the submissive partner and making sure that the pleasure only goes one way.

Strap-Ons: For Her

When we’re talking about using sex toys in a male chastity relationship, specifically strap-ons, we can’t help but mention strap-ons for women. Wearing a strap-on can be quite a powerful experience, as it lets the woman assume a traditionally male role.

That is another way to dominate your man while he’s in chastity. You can show him that he’s such a failure of a man that he doesn’t even deserve to fuck you. Quite the contrary — you’re the one doing the actual fucking because, just like anything else, you do it better than him.

Begging and Pegging for an Orgasm

Pegging is an excellent addition to a male chastity relationship. It provides shameful pleasure for the man and an immense feeling of power for the Keyholder. What’s more, it also allows the Keyholder to tease the man further and deny his pleasure and climax if she so chooses.

Again, because humiliation usually goes hand in hand with chastity, pegging provides a unique opportunity. First of all, most men aren’t used to actually being the bottom in the relationship. What’s more, so many men live in tiny little boxes that have sexual labels on them. Therefore, they can’t seem to embrace sexual pleasure if it’s associated with anything other than what their label says.

Anal penetration is something most men associate with homosexuality or even weakness. Men who label themselves as straight will probably shy away from anal pleasure. That’s due to the misguided belief that anal pleasure is “gay.”

Of course, we know better, but why pass up an opportunity to humiliate your chastity slave, right?

Anal penetration gives the Keyholder the option to tease, deny, or even force the most intense orgasms out of her chastity slave. No matter what the man thinks of anal penetration, after some prostate stimulation, he won’t be able to stop the orgasm from rushing out of him.

The best part about anal orgasms is that they will most likely be humiliating (at first, at least) and shameful, especially if the man grows to like them (and he will)!

Safety First

Of course, when pegging your chastity slave, always make safety a priority. Lube and careful penetration are a must. Assholes aren’t self-lubricating like vaginas are, so you’ll need external lubricant.

What’s more, if your chastity slave hasn’t been pegged before or penetrated anally in any other way, you will need to take things slowly. Prep him thoroughly before penetration (using fingers) because no sexual pleasure is worth a potentially risky injury.

Dildos

Dildos are another way to either get sexual pleasure from penetration or to peg your male chastity slave. When it comes to sex toys for couples, dildos are the most popular ones. What’s more, you probably have one (or a couple) that you can use without having to go shopping.

However, keep in mind that, just like with the strap-on, for a full, humiliating effect, you should choose a huge dildo. We’re talking massive proportions here (if you’re comfortable with that, of course).

The bigger the dildo, the better the psychological effect it will have on the man in a chastity device. Now, dildos don’t allow the same hands-free experience that strap-ons do, but they have their own deliciously pleasurable benefits as well.

For Her AND for Him

Dildos can provide the same options that a strap-on can. In other words, you can use it to peg your locked-up man or have him fuck you with it.

Dildos are one of the most versatile sex toys since they offer pleasure for both sexes. What’s more, there aren’t any specific dildos for men — if you don’t count the smaller dildos meant for anal penetration.

The traditional dynamic of a male chastity relationship is that the only person who gets pleasure is the Keyholder. The man doesn’t deserve to provide penetration, nor is he capable of providing it with his weak appendage.

The Keyholder may magnanimously allow her chastity slave to still bring her pleasure by penetration via a dildo. The submissive man can fuck his Keyholder and see her get pleased and satisfied, which only increases the anticipation and frustration that’s no doubt building up inside of him.

In these situations, the man gets no stimulation at all. That means that he doesn’t even get a taste of what he’s craving for. The humiliation and the lack of control are intensified because the man has to use a lifeless device to do what he can’t.

Not only that, but he also probably won’t get off anytime soon, given that his Keyholder will finish without him (and without ever touching him). Those are the intense feelings that are the focal point of a male chastity relationship and the driving force behind almost every one.

Pegging Is Still an Option

Of course, a dildo offers an opportunity for pegging, just like a strap-on does. The Keyholder can use a variety of sex toys for this purpose. What’s more, she can also pick some of the raunchier dildos for anal play if she so chooses (and if the agreement allows that, of course).

To bring the entire experience to the next level (of humiliation), she can choose to penetrate her male chastity partner with a dildo that shoots out fake come. That way, her partner will feel as if he’s been penetrated by a man. That opens up a space for a whole variety of kinks.

For example, if both partners are inclined, they can indulge in the breeding kink. The Keyholder can use butt plugs to keep the fake come in place or let it slowly drip out of her partner’s asshole to perpetuate the shameful feeling.

Alternatively, she can use a remote-controlled butt plug to tease her chastity partner by stimulating his prostate without letting him reach the climax he so craves.

Vibrators

Because it’s natural to always seek more pleasure, introducing vibrators to your male chastity relationship is the logical next step. Vibrating toys range from small bullet vibrators and clitoral stimulators to massive monster cocks that go the extra mile by offering a pulsating feature. So when it comes to getting sexual pleasure from a vibrator, the sky really is the limit.

Why Use Vibrators?

First of all, vibrators are a surefire way to get you to a fast and satisfactory climax. Because they offer two (or more) types of sexual stimulation — penetration and vibration — they are more likely to get you where you want to be going than most other sex toys.

But in the context of a male chastity relationship, what do vibrators have to offer?

Vibrators offer one-sided pleasure that’s so often the objective of a male chastity relationship. By making the man use a vibrator on you, you’re not only getting physical pleasure but psychological as well.

Your man has to stare down at his sad little penis in a cage and manually fuck you with a vibrator. Not only is the difference in size quite telling of his inability to do what a man is supposed to do, but the vibrator has features his cock simply doesn’t.

So even if he was at the height of his abilities (and he’s not), he could never compare to a vibrating toy that’s plunging into you and bringing you delicious pleasure that’s making your pussy practically salivate.

For an added effect, while you’re making your sad submissive fuck you with a vibrator, make sure to let him know he would never and will never be able to satisfy you in the same way.

Tease an Orgasm Out of Him (Or Don’t)

Just like dildos and strap-ons, vibrators can come in handy if you want to make your man a real bottom in the relationship. Vibrators are better P-spot stimulators than dildos since the vibrations shake the internal walls and provide more intense pleasure. Furthermore, you can use the vibrator to tease his cock as well.

Placing the vibrator gently on the cage and turning it on can not only rattle the man but make him lose control completely. Male chastity usually doesn’t involve any cock stimulation, but if you’re looking for high-stakes teasing session ideas, you should consider some vibrator-on-cage action.

That might also be an excellent way to spice things up in a male chastity relationship where the Keyholder has been teasing the man for quite some time. Of course, just like always, your man won’t be allowed to come unless you specifically instruct him to do that. If he comes without permission, make sure to punish him appropriately and deny him even more next time.

Oral Sex Toys

Many male chastity relationships don’t include penetration at all. So if that’s not your thing, don’t worry — you have options. If you’re one of the many (many!) women who get more sexual pleasure from direct clitoral stimulation than from penetrative sex, you can make your man use one of the many oral sex toys out there to pleasure you.

Just like all other options, oral sex toys will highlight your man’s incompetence. You can, of course, make him pleasure you with his own tongue. However, making him use a toy will show him how much more efficient an artificial tongue is and how much pleasure you’re getting from it.

Because he lives to please you, he’ll enjoy doing both for you. However, because of his already mentioned fragile ego, he’ll also be humiliated.

Imagine being compared to a simple sex toy and falling short. Well, you could never, of course. You’re a woman and his Keyholder — inherently better than him in every way.

Clit Sucking Vibrators

If you’re a fan of clit sucking, you should make your man use one of these bad boys on you. While using the toy on you, he gets to pitifully watch you squirm and squeal with pleasure. Make sure to let him know the exact differences between the superior clit sucker and his sub-par mouth action.

Most of these little suckers come with several different sucking intensity options. You can use that tidbit of knowledge to humiliate your chastity slave further. Let him know that a simple three-inch machine takes direction better than he ever could.

Tongue Vibrators

Just shy from a regular vibrator, the tongue vibrator will still please you better than your man in a cage. So make sure to tell him that.

G-Spot and Clitoral Stimulators

The best of both worlds — a little wand that stimulates you externally and internally --is a fan favorite among women. It’s also a useful torture device. While your man is pleasuring you with it, tell him he could never reach the necessary heights of dexterity and flexibility to stimulate you the way this wand can.

The humiliation here is especially fun and thrilling for you because there’s a good chance your words are entirely accurate. Unlike other teasing and humiliating comparisons you make, this one actually has a lot of merit in reality and not just in your man’s mind.

Fucking Machines

If you want to eny your male chastity slave any sort of pleasure completely, use a fucking machine. By using a sex machine, you’re not even letting him touch you, let alone please you. Not that he could satisfy you, of course. As both of you are well aware, he’s nothing but a sorry excuse for a man.

A fucking machine is really a slap in the face of his masculinity. By riding one and making him watch, you’re telling him he’s completely useless. In fact, he’s so ineffective that you had to go and buy a whole damn machine to do a job he can’t.

Anything You Can Do, IT Can Do Better

Although you can’t tease your chastity slave physically, the machine allows you to taunt him and humiliate him verbally. And as a bonus, you’ll also get your rocks off at the same time!

A sex machine can go all night! Your chastity slave, if he could get it up at all, could probably offer a few pitiful thrusts before he unceremoniously comes all over himself. Make sure he knows that.

Furthermore, a sex machine offers consistency. It can fuck you with perfectly even strokes. You control the depth of penetration, and there’s no chance that a machine can get “carried away” and ruin your orgasm. The fucking machine can also never lose an erection. These are all excellent humiliating points that your chastity slave should hear.

You Can Look, But You Can’t Touch

If you want to organize an extra long and extra demeaning teasing session, we recommend using a fucking machine to its greatest extent. Sit your male chastity slave comfortably in front of you. Well, on second thought, don’t let him get too comfortable. After all, this act isn’t about him; it’s about you.

Then, straddle (or lay in front of) that fucking machine. Make sure he can see everything — the machine penetrating you, your entire body and its reactions, and your face. Then, proceed to fuck the life out of yourself with the device. If you can, try to go for hours or even the whole night! He could never drag those multiple deliciously long orgasms out of you.

Moreover, he could never fuck you for so long. Refractory periods are a bitch, but that’s not the only problem. Let him know that his lack of manly prowess and general inability to step up and fuck you are responsible for your resorting to a machine, and watch his already pathetic self-esteem crumble completely. You’ll surely enjoy it!

A Few Parting Words

A male chastity relationship can be infinitely rewarding. You get the pleasure of being the dominant partner for a change! And just because his cock is in a lock-up doesn’t mean you can’t get an earth-shattering orgasm (or a few).

Fucking while your man is in a chastity cage is entirely possible. Moreover, you have so many options available that the potential teasing scenarios are practically endless. So take that power, lock that cock, and enjoy yourself!