So, pegging, we’ve finally got there! If you’re not familiar with the term, it is where the male partner is penetrated by the female partner, with the aid of a strap on.
I was never really interested in this, and it was one of the few things we hadn’t tried until we got the strap on about a year ago as part of our developing chastity play.
On the whole, my advice is to think about this just like you do if he’s using a strap-on on you. It’s a toy! It’s held in place with the strap on harness so it leaves your hands free. But it’s just a different way of using a toy.
But, okay it IS more than that. And this is part of the excitement of it.
Clearly there is a big element of power exchange in this, but for us it’s actually been a remarkably sensual experience when we occasionally do it.
But as far as the power exchange thing goes, there are two fascinating things I’ve found as we’ve explored this over the last year. It is INCREDIBLY empowering to be the one doing the fucking. It’s hard to describe. It’s just switching everything around when you become the penetrator rather than the one on the receiving end.
It’s almost like those switch movies where the guy goes into a woman’s body and vice versa, it honestly gives me a greater empathy and insight into what sex is like for my husband!
And conversely the same is true for him. In part it’s a similar experience to anything anal that causes him to be aroused or hopefully cum without his cock involved. It totally widens his impressions of what sex is and can be, and I think that’s a very good thing.
A warning that I’ve never seen anyone mention, this will be painful, for YOU. Yep, you will use muscles doing this that just never usually get that movement, well this is my experience anyway. So the next day I was all achey. Which is fascinating because it’s so natural for a guy.
This means first time you may not actually be able to do it for very long. That’s okay! If you’re both really getting into it then you can lie on your back and he can, for the first time ever, try being the cow..boy? Anyway, cowgirl position with him sitting on the dildo. And yep, that’ll make HIS muscles ache! lol
That isn’t all that aches, of course. For those of you who like, or have at least tried being on the receiving end of anal sex, there is an achey throbbing feeling of being fucked there. He’ll have that too, that’s normal.
As for some of the practicalities, here are some of the headlines, but I’ve added some great articles from other sites with all kinds of tips too.
Make it sensual, not dominating, at least at first. Treat this as kinky love making rather than some fantasy domination scene. His body is DESIGNED to be able to take pleasure and orgasm from stimulation of his prostate, so this can be an incredible experience.
Get him to be nice and clean beforehand – a shower and bottom wash is great but an enema a few hours before will get him even cleaner.
Use a condom on any toy that isn’t just for anal only (it’s SO weird putting a condom on yourself!!!)
Use lube, lube and more lube, you can never have enough. Lube the toy yes but literally push it against his bottom and squirt it up! Or else lots of it just gets wiped off as it goes in.
Foreplay to relax him is great. A lubed finger is perfect, or playing with butt plugs. Again use all of that as a chance to get lube in there.
Take your time. He’ll need to relax, get used to it, and relax again so no hurry, talk, touch, tease, play with his cock too.
Uncage his cock so you can wank him too. It’s so hot. One hand on his cock, one on a nipple and pegging his bottom, he’ll be in heaven.
Of course the big question is whether you can make him cum like this. It took us four or five different attempts before we got that right. Now we have it seems to be easier, and we’ll even do it with him caged so the stimulation is ALL from the peggng.
But cumming isn’t the entirety of this experience, simply doing it is the big thrill, and really worth trying.
Despite nearly every picture on Tumblr being of pegging Doggy Style it’s one of the worst and least successful in my experience. Him lying down as in the picture further up this post is good for aiming and slowly working the tip in.
Spooning is my favourite as it’s all snuggly and I can whisper in his ear and play with his cock and nipples and the rest of his body as we do (reach your lower arm around under his neck).
We’ve tried him lying on top too, that kind of works but I think you need a longer toy for it to work well. But sitting up, cowboy style works well but wasn’t as sexy as me doing it to him.
But face to face is also a favourite. This was the position that first made him cum from it and OMG…looking into his eyes as I made HIM cum from fucking him – absolutely incredible.
Equipment
You need a good quality strap on and a nice not too big dildo (most of the ones in the pictures are ridiculous…), plus some good lube
This is the one we use from Lovehoney, it’s wonderful, it works just as well on me as it does when he wears it. It has different fitting sizes so it can take the bigger dildo we love to use on me. But slim, curved, silicon one it comes with is PERFECT for pegging.
So we’ll continue the theme of plugging today if you have one, but it’s going to be combined with that I think is key in any relationship, a date night!
We didn’t have date nights routinely until a few years into having kids, when friends told us to get them sorted or we’d never get any romantic time. They were right!
So today’s a chance to have another date night. See the impact of this time of chastity exploration has had as he takes charge of the evening. Food, something to do together, a movie or something else you both enjoy.
And as I said, add caging and ideally butt plugging to the mix to see what effect that has had.
Tonight in bed the focus should be about you, but I’d suggest if you are letting him out, a good edging to get him really horny for tomorrow would go down well.
So as promised, butt plugs are coming into play today in order to get us more relaxed for the weekend.
So, if you’re able to, try getting him wearing it during the day, at least for a while. I find that it acts like a hornyness accelerator. It gets his balls full faster, turns him on more, it’s a brilliant accompaniment to caging.
And of course you can leave it in him for your playtime tonight too. I especially like him wearing it when he’s using the strap on me as it stimulates his prostate as he’s thrusting and he ends up dripping out of his cage, so, SO hot.
Just use today as an opportunity to discuss how it feels and what it does for him. If you have two plugs you can always wear one too, make it a shared experience!
They do take time to get used to, so if it gets uncomfy, just take it out. But give it time to settle, remember to use lots of lube to put it in.
If you’re squeamish about this, and I get that, I really do, please try and just push past it today, just so you can try it out. Particularly on guys the bottom is a source of all kinds of pleasure, and it’s really worth at least trying it out to see if you’re missing out. Taking it out in the shower is the easiest way to have no clean up issues at all, but just babywipes do great otherwise.
So yes, as suggested above, try some strap on sex with him plugged perhaps, a perfect opportunity to remind him soon that the tables will be turned! Or just have him go down on you!
And if all this isn’t for you, just pick something else from this month or have a night off!
So we haven’t actually had much sex during this Locktober. And I guess that reflects how it sometimes goes with caging, we tend to have less penetrative sex, but much more actual sexual time together.
That’s a mixed blessing. I do miss him in me, but I don’t really miss the mess he used to leave, and the fact when we’re making love, he tends to get focused on what feels good for him.
What we’ve done more and more over this year is uncage him to have sex, but he doesn’t cum, which again is a real mind fuck, but refocuses him on enjoying it but keeping control. The rule has become that if he does go over, he has to pull out and ruin it on me, and then clean up. This is surprisingly hot, so it’s a bit of a win-win for me.
It also makes him cumming in me the pinnacle of pleasure, he keeps getting tastes of it but it makes him long for it so much more. And that feels right, I don’t want blowjobs or hand jobs to take it’s place as what he really aches to have.
I also use it as a tease, when edging him with my hand, for example, I’ll say ‘i would let you cum but I want to save it all for my pussy, and I don’t want to get messy today’. What a great excuse to not let him cum, leaving him thinking and wanting you even more!
So today you have a few options. If you’re enjoying restraining him you could do that again and uncage him, and do a mix of grinding on him and cowgirl sex to edge him.
If you would prefer him to do the work, then you can lie back and have him go down on you (let him make you cum this time, before he gets in you) and then have him fuck you till he edges, with the ‘ruin and lick’ provision in place if he goes too far.
Make it personal, get some eye contact, kiss, tell him how much you love all this. Tease him.
And then, if you’re feeling a little mean…at some point whisper, ‘I want something bigger’ and have him wear the strap on. If you leave him uncaged with the strap on, in missionary position his cockhead will rub over your bottom… it feels amazing and is a HUGE tease for him!
If you’re feeling even meaner, you can lock him up of course. Or never let him out in the first place, and just use the strap on. You really are in control now, enjoy it!
Some advance warning. This weekend, as promised, we’re going to try some sensual pegging (where he’s penetrated with you wearing the strap on).. So, firstly if you want to try that and don’t have one, you will need a strap on harness and dildo. Secondly, it’s well worth him getting used to some play there by using a butt plug, so it’s easier and you can both enjoy it more. So if you don’t have one, here’s our recommended ones – the Roll Play Plugs from Lovehoney. I’ll include some tips for him wearing them over the next few days.
He probably thought he might be getting out tonight if he didn’t manage your criteria from yesterday…. he isn’t! lol
A bit of an adaptation on a previous post today. You tried, I hope successfully, to give him a caged orgasm last week. Tonight we’re going to try edging him in the cage!
The same options apply as before really – use a vibe on the cage, use a vibe on his prostate or a toy in there! But this time, no cumming.
If you haven’t watched the video I posted yesterday, let me really encourage you to check it out. It’s utterly fascinating. And while not anything attractive, just treat it as a bit of a biology lesson on just what a man’s body is capable of, because omg, he’s having his mind blown:
So a nice one today, some training for him, on going down on you.
He’s going to stay caged, and spend the entire time down between your legs.
But this time it’s a game. You see you have to set some secret criteria.
An amount of time, and a number of times you cum. You don’t tell him what they are, just that you know.
If he meets BOTH those criteria then afterwards you can reward him with a nice long edging. Otherwise he just stays locked up.
I’d go for something like half an hour and four orgasms but you could make it harder or easier. If he’s not done it much then his tongue will be worn out after 15 mins or so. But he can use fingers or a vibe to mix it up!
Get somewhere comfy for this. Lying in bed is of course a good start but it’s often easier if you’re on the edge of the bed so he can kneel and be more upright – he can breathe more easily and move around more. Or sitting on a sofa is hot, or lying back in a chair like
So while he goes down on you, you can do what you fancy! Read a book, put on some TV, browse Tumblr. I’d personally go for something sexy, read some erotica, watch some porn, let him hear that, comment on it, tease him… so good.
A few things you can do to make this sexy for him too.
Be vocal. Yes, you are putting it on a bit but that’s OKAY! It turns him on like crazy and actually it’s really just letting it out. When he gets something right, make noises to show him! Say it feels good, swear under your breath.
Grab his head, his hair, press him on you – so hot – even rub yourself against him
Tease him – remind him of his caged cock, how much you love it, how it must be straining, dripping, that you should just keep him like this, all you need is his mouth now
Instruct him – don’t just leave it all to him, take control sometimes, tell him what to do – lick my clit, tongue fuck me, suck gently on my clit, finger fuck me, stick your finger in my… – it’s fun treating him like a sex toy! And then, of course, tell him, ‘make me cum now!’ when you want to
Be daring, try some bum licking – try lifting your knees up and telling him – lick lower… or simply rolling over and presenting your bottom to him – then rub or vibe yourself so you cum while he licks your bum
Here’s a few captions I found that might inspire you…
So I’ve had various requests this week for more teasing of various kinds so I thought I’d indulge that tonight. Also I’ve pointed you to some of the best tease tasks we’ve written for this Locktober – worth trying if you haven’t or doing again!
So a bit of a mix and match but you’re getting good at this now!
Teasing is just a huge bit of denial, for us anyway. I know some guys fantasise about being locked away for months with no release at all but for us the cage is very much a tool to enable and enhance tease and denial play together.
We’re doing the strict lock up option so that means hubby will be restrained before (or if… lol) I decide to take his cage off, and it’ll go on before he’s untied too.
If you don’t have restraints then just making him put his hands beneath him with the threat that if they come out he’s locked up, no warnings, is hot too! But him actually pulling on the restraints, yeah, even hotter in my mind!
So the other day I mentioned a great source of the videos we like most and I’ll flag it up again as I think they are super sexy and links like this don’t tend to last very long
So one of my other favourite types of teasing is about cock size, you may have noticed? If this isn’t for you, no problem but, yeah, turns out we both love it
So here’s an image to get you started… even just admiring it will get him going.
There are lots of pictures and phrases to tease him with from the earlier Locktober post Day 8 Size Teasing so have a visit to that together!
Something that drives hubby crazy is if I tell him to go down on me while i look at this kind of thing… why don’t you try it.
Or if you have a big dildo then get it, and start using it, right next to him. More tips for that on from Day 15 – Tease and Tied
If you fancy mixing things up again you could use the Wheel of Chance we made for the Spinner task recently.
And then if you really want to go for it, why not revisit last night’s strap on adventures, I can’t think of a better way to end the evening…
nfrdm 