Further update:
The “D/s lifestyle” thing has all but disappeared from our relationship now, but there’s still very much a D/s vibe when we’re in playing mode. It’s absolutely the case that I do as I’m told, within our agreed limits.
My “Boss” has become a very good friend to me, with exceptional Read more… benefits! It’s a mutually beneficial arrangement that is continuing to work well for both of us.
The play we engage in has become ever more extreme, and consequently more exciting. Not that I’m lacking anything, but I want to share these experiences with others, so I’ve had permission to play away too, with conditions. It’s all good. Very good .
Further updates to follow in due course…

I’ve been meeting up with people through various media over the last 30 plus years. I’d agree that there are a much lower proportion of meetable women on sites like this now. I used to have a big choice of females to pursue a meet with, but now there really are very few.
One problem is the sense of Read more… entitlement that persists. This never used to exist, or at least it was rare. Many players now have such an entitled attitude and get nasty when consent is not forthcoming.
And then you get those that have “post meet regret”. And they then ghost you. Or turn nasty. Either way, it’s not nice.
I have to say that although I’ve had some of the best conversations with folk on here, my best and most memorable physical encounters and experiences have not been with those I’ve met through this site. Paradoxically and unexpectedly, it’s been people I’ve met through a couple of well known hookup apps that have made for the best kinky encounters. Possibly because I’ve found ways to post very detailed profiles of myself, which effectively vets potential playmates very well: most are frightened off!
This means that those that I do meet with are usually already very well informed of where I’m at and they know their own needs well enough to know that they’ll be getting pretty much what they want. This works well for me, but then I do have very extreme kinks by many people’s standards.
Many folk on this site are here to “heal” or “recover” from something. Many have “issues” or “triggers” that need “therapy” involving BDSM practices, apparently. And all that is fine.
But it’s not for me. I don’t want to be a shrink, a therapist, a mentor, a Daddy, a Dom or any other label apart from “playmate”. Fun is what I do this for. That’s all. And my experience has been that there are a lot more people, including those of the female of our species, who share my view, on other vehicles than this one.
So everyone has a choice. If this site works well for you, happy days. If not, consider moving on!

Yep. Just you. Enjoy!

Well I’ve been playing for well over 30 years. I’ve tried just about every different lube out there. I love J-lube, but it’s messy and a bit of a faff to prepare. I’d definitely use that for a really good fisting session. It’s best mixed up with a blender, with a good dollop of aqueous cream with Read more… it, which helps to stop it drying out so quickly, and it also reduces the crazy stringiness of it.
These sachets of “silky” lube really aren’t that good and they can leave you feeling sore and irritated. I just don’t use them anymore.
Proprietary lubes such as Durex lube is ok, but it can be a bit sticky. KY Jelly has been around since Adam was a lad, and yeah, it’s ok, but really? Meh…
My everyday go-to lube for anal play is Tresemmé hair conditioner. Yes, really! It’s cheap, readily available, smells pleasant, it’s easy to clean up and it’s non allergenic. It stays where you put it (as in “between the cheeks, not on the sheets”) and as it’s water based, it’s kind to toys, including silicone ones. As I don’t own a vagina, I couldn’t comment on it’s suitability for such an orifice, but it’s certainly very good for bottoms!
Body shop body butter is lovely stuff for intimate times. It massively reduces friction and improves sensitivity. It seems to be kind to both anal and vaginal orifices.
Baby oil is just amazing, but it’s not easy to clean up and will probably end up leaving you with thrush. Not nice. Best not used internally.

It was early May last year that I posted the OP on this thread. Here we are now some 15 months later, and all is well, absolutely incredible, in fact!
My Boss has his health issues that cause him discomfort and sometimes he just can’t play. I make allowance for that. But when we do play, pretty Read more… regularly, it’s amazing! To have built trust with a playmate over a long period can lead to activities that bring levels of satisfaction and sheer unbridled joy that simply aren’t possible with brief fleeting encounters.
To all the naysayers: you were all so wrong on this one, but thanks for your well-intentioned advices.
To those who were supportive and excited for me: Thank you!
This is an adventure that gets more exciting with every meet and the level of extreme play we have reached is beyond anything that I ever could have dreamed of, or even fantasised about. When you find a playmate that is so in tune with you, who gets just as much out of a session as you do, with you both fulfilling each other’s needs and wants so fully, it really doesn’t get any better than that.
All of this experience goes to prove that you sometimes have to take a punt. You have to seek out that person that you don’t yet know, the one that is going to be that incredible playmate that you click with so comprehensively. It’s worth the effort when it happens.
And for the record, I’ve never been physically hurt, threatened or otherwise ***d outside of the mutually agreed boundaries we’ve set. My Boss is first and foremost my trusted and deeply respected friend. We don’t have official exclusivity over each other, but why would I want to play anywhere else when it’s so good here? It’d have to be a pretty special offer…
When you find a playmate like this, it’s absolutely magic!

I have recently posted about being punch fisted by my machine. I wouldn’t say it’s addictive, but it is pleasurable beyond description! I can see how it would possibly become addicted to some people with a certain type of personality.

Thanks @PebblePebble. Not being the owner of a vagina, I’m evidently not as in tune with the needs of such an orifice, compared to a rectum!
However, I do consider that my comment about not stretching is the most important thing. I had a long discussion with a surgeon about this and they confirmed Read more… that it’s stretching that really does the damage. This is one reason why they prefer to cut a woman’s birth canal during childbirth rather than have her tear.
When you say that you don’t think that a vagina can be “trained“, is it any different with a rectum? Can that be “trained“? And what is “training“ in that context, anyway? I certainly know that I “trained“ my former partner’s vagina, in that we achieved ever larger and larger penetrations, over a period of time. But she was definitely not “stretched”. She learned to relax, more and more.
As a free diver, I know that to get ever deeper on one breath of air, you use “incremental progression“, where you are doing the same as you did last time, and then just a little bit more. It’s all to do with managing the mental aspect of things, much more than the physical. This is exactly how I got to the stage where I am at now. But I also know for sure that I am not stretched. I am not loose and my rectum certainly doesn’t need a nappy. I’m glad to hear that your vagina doesn’t need one either! Happy days! 🤪

Oh dear. Yet again, too much inaccurate, and wrong advice, sadly. I’ve been doing this for over 30 years and therefore consider myself to be reasonably experienced. I’ll keep this pretty brief, but feel free to message me privately if you want further detailed comprehensive information!
There’s a Read more… lot of good information on this thread about this, but not all of it is good. As always, there will be many people with a little knowledge who think they know a lot.
The same thing that comes up on every such discussion is “stretching“. Stretching in any way at any time, for any reason, is physiologically definitely not good. Stretching causes tissue damage, internal bleeding, nerve damage, scarring, and permanent slackening-off of muscle, which you certainly don’t want “down there“! Women who have been badly stretched during childbirth are permanently changed.
If you take nothing else away from this entire thread, take this away: It’s absolutely NOT about stretching. It’s about relaxation. The latter infers that you need to be comfortable, in the right environment, with the right person, having done the correct preparation, and most importantly, being in tune with and knowing your own body. So without wanting to put too fine a point on it, if you can’t already take a toy that is a bit bigger than the fist that you want to take, you shouldn’t even attempt it.
The biggest barrier to this kind of play is mental, not physical. Achieving total relaxation requires you to be in the right place in your head. Otherwise it simply is not going to happen without physical damage.
Playing by yourself, you are in control, and you can get to a point where you feel comfortable with a certain toy, then you can take it a stage further and involve somebody else. Proper relaxation comes from having the mental knowledge that you’ve done something almost this big before and you’re only going very slightly bigger this time. Small incremental steps lead to confidence and subsequent total relaxation.
I have fisted a woman who had never experienced it before and I certainly consider that having also previously experienced having been the fistee myself, it brings a lot of empathy, understanding and consequent care in the conduct of such play when you are the fister.
For me of course, it’s anal, not vaginal, but the same considerations apply. I can take some huge toys and I can take a fist or even two very easily, but I’m also still very tight and I don’t need a nappy. That’s because I’m relaxed, not stretched. Because I’m confident in the knowledge that I can take something of a certain size, there isn’t a mental block and understandable apprehension about having something huge pushed inside me: I know that I’ve done it easily before.

You’re going to need lube. Pegging is just one aspect of “anal play” of course, and there are many more aspects.
Use lube. I’ve been pegged by my ex-wife over 30 years ago and I loved it, in a purely carnal way. But because we were young and inexperienced, it was a bit perfunctory and so anal play Read more… for me now is more about the entire experience, with a deep emotional connection being essential for the best outcome. This connection can happen quickly with the right playmate.
Lots of lube. It’s been a long time since I was “pegged”, but I regularly enjoy being penetrated by large toys. The most sensation is felt through the rectum and sphincter, not the intestine, so I generally don’t use very long toys, unless my playmate particularly gets off on the idea of that. So yes, I’ve had long flexible toys over two feet long inside me, but it’s the 3.5 inch diameter Fat Boy type of toy that really does it for me. The sensation of the movement inside me is incredible.
Water based lube is great. But so are other lubes. Tresemmé hair conditioner works really well for me. And it smells nice. And machines. Oh, yes please! The power dynamic that can be established when I’m firmly restrained and being banged by a 3 inch diameter toy fixed to a capable, indefatigable, relentless machine, in the control of a suitably interested and intensely involved playmate that is getting as much out of it as I am, is just…mind blowing. And that’s what, for me, leads to the full body orgasms and out-of-body experiences that I feel privileged to have experienced on a regular basis. This can’t usually happen for me during “normal” vanilla penile/vaginal sex (although it did happen on a couple of occasions), so some sort of anal play is always a bonus.
Lube. Did I mention lube? It’s really, really important, and you can’t have too much. But. There’s always a “but”. And at least one butt, of course, in this context! For it to be enjoyable and safe, you need to know your own body very well. A torn sphincter, a ripped rectum or worse, a separated colon is going to require surgery and it’ll almost certainly bring a permanent end to any such play. So preparation and understanding by both (“all”? Lucky you!) participants is key. If you are thinking “Ewwww…” and screwing your face up in disgust at the thought of squatting down in the shower with a douche (or for the more experienced, a shower head or hose douche attachment) and giving your back passage a good flushing out prior to getting it on with your playmate, then it’s just not for you! If a bit of poo absolutely repulses you, then stick to knitting. If you don’t know your own body well enough to be able to know when something isn’t quite right, then you shouldn’t let someone else stick anything inside it! Oh, and lube, don’t forget the lube. I think I might have said something about lube already…

Well this is a simple one to address. You’ve not been relaxed.
It was 31 years ago, I was in my early twenties and I had my first anal sex experience. I really wanted it and I thought I was ready for it. It was awful. So ***ful. I just wanted it over. I ached “down there” for over a week. I’d Read more… certainly been internally bruised .
I didn’t understand why I was able to take big toys inside me and be comfortable but this experience was so ***ful. I soon realised that I hadn’t been relaxed and “in the zone”.
The next time was completely different. I talked through my first experience with my playmate. I explained that it had been ***ful. I also expressed my genuine desire to have sex anally, but to enjoy it like I enjoyed toys. He was very gentle, went slowly and gave me time to get in the zone. I totally enjoyed it. No ***. No long term aches. Just pleasure and fun. Things just got better and better.
I’ve been playing for well over 30 years now. I’m able to take a 3.5” diameter toy in me. But I’m relaxed, not wrecked. I don’t need a nappy!
My advice: Plenty of lube. Plenty of time. More lube. No rush. Even more lube. Relaxing breathing exercises. Did I mention lube? And poppers. And lube. This will lead to serious fun and unbelievable pleasure. Enjoy…😀