7 Crazy Fun Chastity Pegging Ideas For Your FLR

When you introduce chastity into your female led relationship (FLR), it opens the door to a lot of fun.

In fact, once you start chastity, you will inevitably start experimenting around with other fetishes like cuckolding, foot fetishism, etc.

And eventually you will get pegging.

Pegging your slave husband/boyfriend in chastity is a lot of fun because it provides him with stimulation in a non-traditional way.

Plus, the power exchange of really fucking your partner this way is so empowering. Pegging is also a great way to experience erotic humiliation with your partner (if either of you are into that).

Pegging is a great fetish to explore with your partner and it's the topic I wanted to talk about today.

Specifically, I wanted to share 8 crazy fun chastity pegging ideas you need to try!

What is Pegging & Why is it needed?

So...what in the world is pegging?

Well, in a nutshell, it is when you penetrate a man's anus with a dildo or strapon. Simple enough, right? :)

Pegging can be used in a variety of ways in your FLR.

One way to use pegging is to provide a reward to your slave.

Now, most men may be apprehensive at first when it comes to anything coming in contact with their anus like that.

But once they experience it for the first time, they REALLY begin to enjoy being pegged.

Anal play is a great way to explore beyond chastity - as you can provide him prostate stimulation even while he is locked up in his cage!

You can peg your chastity slave as a reward for a job well done. Peg him and make him cum in his cage (i.e. give him a "sissygasm").

If you've never had a sissygasm like that you are missing out big time. Just search "sissygasm" on Twitter if you don't believe me!

Another reason why you want to peg your slave is to punish him.

But how can pegging be both a reward and a punishment?

Well, it all has to do with the size of the cock used to penetrate him!

For example, smaller cocks are better for the pleasurable side of things. Meanwhile, larger cocks will be used for punishment to stretch out his hole!

Now, obviously "small" and "large" will vary depending on the person.

Anyways, let's talk about some fun pegging ideas to try on your partner!

1. Fuck him over the bed!

One of my favorite pegging games is the simplest.

And all it requires you is to take charge as the alpha female in the relationship!

Bend your partner over the bed and lube up your cock. Play around with his balls and his hole with your cock.

Whisper dirty things into his ear like:

  • "I bet the anticipation of my cock is killing you"
  • "How bad do you want my cock?"
  • "I want you to beg me to fuck you like a sissy slut"

That will really fuck with his mind!

Right before you peg him, order him to open his mouth.

Then, you will stuff your wet, dirty panties into his mouth and inform him that you are doing it so he doesn't scream loud enough for the neighbors to hear!

After that, grab his hips and start thrusting your cock into him! Keep going until you are satisfied with the pounding he took.

2. Make him jerk to it

Okay, the last idea was a "punishment" pegging idea. This one will be a "reward one".

Order your slave onto his back.

Then, lube up your cock and begin thrusting your cock into him!

Meanwhile, order him to start jerking his cock (while it is still locked up).

If you want, you can also squeeze his balls softly with your fingers - nothing too hard, just enough to make him moan and get even harder in the cage.

Keep thrusting into him until he has a frustrating sissygasm in the cage.

Oh and after he cums, make him lick it all up. After all, that cum should be recycled! Not a drop to be wasted at all...

This is how cucks should cum!

3. Make him do cowgirl...

This is one of my favorites because of the humiliation factor.

I'll leave it up to you in terms of if you want it to be a punishment or a reward. But regardless, it will definitely be very humiliating for him!

So here's what you're going to do...

Lie down on the bed with your cock pointed straight at the ceiling.

You are going to have your chastity slave do the work and ride that cock cowgirl style!

He probably won't be used to the motions so it will be really funny to watch him in action!

If you really want to humiliate him, you can record a video of him riding that cock like a slut!

Be sure to slap his ass while he's riding that cock like a sissy. Oh and be sure to tell him to moan like crazy too for it to be even funnier!

This is a great idea if you're into erotic humiliation.

7 Crazy Fun Chastity Pegging Ideas For Your FLR

4. Have your bull peg him

If you are into cuckolding, another way to really fuck with your cuck (literally and figuratively) is have your bull peg him!

If your cuck has never been pegged by another man before, then he's in for a real treat!

Talk to him about it beforehand, obviously. There may be some objections, but eventually he will come around!

When the big night comes along, your bull will bend him over and take his anal virginity!

What a good way to lose it right? Not only did your bull fuck you, but he also fucked your partner as well!

While your cuck is being pegged, whisper some naughty things into his ear. You can even make out together to make it a bit more intimate.

After your bull has finished pegging him, have your cuck suck his cock in thanks. That will really add to the humiliation factor.

5. Make out while you peg him

Another fun way to peg your cuck is to make out while you do it. And this one would definitely be on the "reward" side of the spectrum.

Peg your chastity slave while you make out with him! I find this is a highly erotic experience that all couples should try at least once!

Have him lay on the bed while you get your cock ready.

Put on your strapon and guide your cock deep inside his sissyhole. Do it slowly and softly. It's supposed to be a romantic experience after all!

Thrust into him slowly as you make out.

Moan against each other as you tongue wrestle and swap spit. Keep going until you are both satisfied with the make out session!

While you're making out, you can also reach around and lightly slap/tap his caged cock. This adds another element of teasing that will really elevate the experience.

6. Have your cuck "play along"

This is another fun game for cuckold couples!

Next time your bull is over, allow your cuckold to have fun too! After all, he may get restless just watching you cum on his cock all night long :)

While your bull is fucking you, give your cuck a dildo and have him peg himself on the bed right next to you!

As you are getting drilled by your bull, grab your cuck's caged cock and squeeze his balls softly as he's fucking his own sissyhole.

Order him to go faster or slower based on how fast your bull is thrusting into you.

This is a great way to make him "play along"!

But make no mistake...there's only one person cumming that night and that's you!

Your cuck will just have blue balls and frustration after it's all said and done. That's the beauty of chastity!

7. Milk him in chastity

Giving your cuck a sissygasm by pegging him is an incredible reward. As a result, you should only do this when he has really pleased you.

Now, giving him a sissygasm by pegging him requires him to be incredibly aroused - both mentally and physically.

The best way to achieve this is to lock him up in chastity - the longer the better, but I would say at least 2 weeks.

At that point, his balls should be full of cum and he should be SUPER horny.

Lube up your strapon and peg him over and over again until he cums in his cage.

Trust me, it may not sound like much, but this is an incredible way to cum.

Chastity Pegging Ideas - Final Thoughts

Overall, pegging your partner in chastity is a great way to spice things up in the bedroom.

Pegging can be a very intimate experience for both partners. And depending on how it is used, it can be used for erotic humiliation as well.

In fact, I would say chastity and pegging go hand in hand! Once you try it, you may be addicted though.

So...which chastity pegging idea from this list do you like the most and want to try?

Or maybe you have a naughty idea of your own?

Let me know in the comments!

7 comments

  • how I wish I was just getting married and would be cuckolded on my wedding night by a black bull with a huge cock He will not use condoms so I may have to bring up a black baby and everyone will know that she has been unfaithful Michael xxxxxxxxx

    Michael Toyn
  • one other thing can be done is give the cuck an enema and cleanse him out but use tampon for super flow make him hold it and also loosens him a bit too to take strap ons easier

    stuck in middle of sorts
  • Still working on getting my Mistress to peg me, so in the meantine I put her large strapon on a pole and practice opening up my boipussy solo (just so I’ll be ready for Mistress). Of course I remain in chastity while I do it. Have had 1 ‘ruined’ orgasm (magnificent) and several powerful regular orgasm’s. Of course I don’t waste it and clean up and swallow all that sissyseed. I can’t wait for Mistress to step up and start pegging me good. Maybe after that Mistress will find a Bull and introduce me to him to service.
    Hopeful

    Doug
  • Well, This beta sissy loves the idea of being in panties , trained further in feminization , sissification and being a sissy slut taking a strapon by a dominant woman in a long term FLR . I want to worship and obey her desires , wonder if that will happen in reality with the right woman ?

    Neil
  • my Fiance was balls deep into my ass within an hour of our meeting. A couple of months later we were finally able to get a chastity device in place. The satisfaction we both got from our sex-life(almost all pegging or via cunnilingus) improved dramatically! Occasionally I strap a BBC on above my cage and fuck her. Chastity is a primary facet of our relationship. Should be getting a PA piercing soon 😱💞

    jerry

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