As a male who loves a bit of bum play I’d say initially go slow. Whilst giving a hand job use the other hand to put a bit of pressure on the bit between the balls and hole. This feels nice but then slowly go a bit lower and a bit lower until you are just very very gently touching and rubbing the hole. If he doesn’t resist then apply a bit more pressure and then before you know it you’ll have a finger in, rubbing the prostate and giving him the orgasm of his life. I know there is still a lot of stigma when it comes to the bum but I don’t know why when there is so much pleasure to give and receive!!
Since the wife started playing with me I’ve got a bit more adventurous and got the NJoy wand for a bit of solo prostate fun. Would imagine it’s great with a partner as it’s also meant to be amazing for the female g spot
I’m getting used to my prostate massager now and absolutely love it. Have had only one orgasm but it was amazing, wasn’t even touching myself. Never felt anything like it. Definitely keep at it
I basically just gleaned some knowledge and while we were shopping for toys I just casually said I’d read somewhere about the prostate and just regurgitated some facts I’d learned on here to him.
It took him a while but eventually he came round and we bought some stuff to try. He’s tried a bit here and there but it’s early days yet for us too.
As a gateway idea, today I suggested he put our wand on his perineum and he actually loved that, said it felt really nice. Non intrusive and if he lets you it’s something you can do without him hitting the ceiling.
Saying that I found for us personally it’s been better for him to explore himself first then bring it to the sessions once he’s ready. He lets me watch so I’m cool with it.
That’s just us though, he’s naturally dominant sexually and was very, very hesitant when I once asked him if he would ever let me peg him. 
So I won’t bring that up again until he does, but I suspect it’s because he’s been asked to do anal on previous partners (I’m not in to it personally) and he far prefers PIV so doesn’t see yet the benefits it could bring to him.
Re the gay thing, you could just casually mention there’s nothing more attractive than someone who is well and truly comfortable with who they are. You could also say I enjoy being licked but that doesn’t make me a lesbian just because they do it too? It’s flawed logic! But I get that it’s a real concern for a lot of people. Maybe I’m too blunt but that seemed to click for my butt-reserved-masculine-hetero-protective male. 
All the best on your butt loving journey.
I’m jus bout to purchase an upgrade on mine, bigger n stronger. Maybe let him try a toy on his own, let him get comfortable with it n see from there
What toy was it
I have a plethora of anal toys and massagers, but still chasing the unicorn of an anal / Prostate orgasm.
I have managed to ‘milk’ my prostate using my NJOY wand … and love licking that … but never yet, the full Monty
R xx
The aneros vice2 got delivered today. Anyone tried it? I’m charging it now!
@Dom624 - no haven’t tried that one - let us know how it works and if it can deliver the holy grain male super O hands free.
Have tried it once, didn’t get there but was nice as always. Will give it another go now tonight I think
Yes sometimes good but not quite there.
I was born female…but I’m intersex. Found out this summer that I have a prostate, of all the crazy things. I was enjoying anal sex long before I knew about it.
Most of the time, I pass as (and have sex as) a boy. Which means mostly anal sex with my husband, and a focus on the spot inside my that I really like…which happens to be the prostate. IDK how my nerves compare to those inside an actual “XY” boy, but I’m really sensitive. A combination of anal pressure on the prostate and plenty of stimulation in front creates a surprising amount of liquid dribbling, along with some very weak-in-the-knees orgasms.
@Dom624 I’m seeing this late. But. I got mine a few days ago from LoveHoney.
I’m a long term user of Aneros products.
They gave me my first prostate orgasm.
Then I got acclimated and learned how to Super-O. That’s. Well.
The Knee shaking, earth rumbling uncontrollably vocal, “is this even real” level of orgasm.
The Vice 2? Haha. Well. Mine was delivered by LoveHoney a few days ago.
Let’s just say it as according to others that have posted where you would expect to find their posts, go from a 90 minute warm up time to Super O launch, to a sub 20 minute rolling wave of Super Os?
Absolutely correct and true for me. My GF just sat there for over an hour lightly touching me while I’m spasming like I have a neurological disorder, full body style, one after another.
I’m a very reserved quiet dominant type of “orgasmer.” And Super Os objectively make me look absurd. But they are so amazing I literally (can’t)care about that.
After that hour or so of watching. She just rode me. Almost every time I hit another super O. She hit her own orgasm. And her orgasming between caused another Super O peak.
I had no clue how long this went on until she eventually got off me and ever so sweetly asked me if I knew what time it was or how long that had been going on.
It was a little over 3 hours later and…that’s the effect a Super O has when you are finally able to have them.
Vice 2? Amazing isn’t a descriptive enough word to use. I can’t think of any word short of “ethereal, celestial, “out of the realm of comprehension,” capable of describing the ease, frequency and duration it causes Super-O’s.
If anyone reading this is at all curious after reading that. Buy one from LoveHoney and actually do the research to learn how to use it as it’s meant to be used (hands free, controlled by the “slip out, grip it, pull it back Kegel control,” with or without vibration mode on) and well.
I can guarantee you that either your life will be forever changed. Your partners will be.
Or both of your lives will be if you’ve got a Girlfriend (or Partner), like mine who’s not only accepting of exploration but also encouraging of it.
Edit; Forgot to add, give your girlfriend/wife/partner the remote and let them help push you along if they are attuned to your pleasure peaks, might just be the very thing that gets you to the Super-O. Especially with the touch sensitive 1-4 levels of intensity Joy button that overrides the set vibration pattern and intensity.
If that doesn’t do it. Well. Keep at it. But they won’t be “left out watching you,”’and will probably enjoy “controlling my ride as much as my GF did, while she was riding me.”
Sustained use time is 90 minutes but it you keep the vibration low; which won’t numb your prostate as fast. And every now and then get that Joy button spike unexpectedly from your OH’s control. It can last a lot longer than 90 minutes.
I meant the vibrating part of the vice 2 when first writing that edit, then was like oh good I didn’t state it that way.
Because I meant, the vice2 vibration, the Super-O (once you’ve learned to have them and how it’s like riding the best rollercoaster wave in existence), and the entire experience for both of you will be longer than 90 minutes.
I have a free day and night tomorrow so have a date with my NJoy planned and hopefully finally reach the super-o. Just reading your message has got me excited as I’ve heard so many amazing things about how the super-o is much more powerful and lasts longer.
My problem is I think I am too eager and try rushing when trying before. Do you have any tips as an experienced super-o-er? Is it just being patient? The NJoy has got me the closest to what I thought was going to be a super-o but never took me over the edge 
Up until a few years ago I had never considered anal play for myself and it was my wife that introduced me to it completely unexpectedly and never looked bk
None of my previous partners have ever wanted me to play with their anus and some have not wanted to play with mine. Strangely the stock answer they have given is that it seems gay which I find very odd in this day and age.
Mr B has been open to everything we have discussed or tried and this subject is one of them. We don’t tend to plan things as when we start something we tend to be spontaneous and go with whatever we feel like at the time.
Our first experience was when we had been kissing him then started to play with him, as I did I slowly inserted a finger inside him asking if it felt OK and if anything felt differently. It was a bit like when he had his fingers inside me looking to find if I had a g spot which I didn’t know at the time. After a while of playing around he said something felt nice and I realised that the little lump thing that I was touching must be his little walnut prostate. He got on his hands and knees and I tried again, this time after a while we both realised what prostate milking was. He has only ever cum once with me doing it but has much more intense orgasms when I touch there at the same time as playing with his cock. He has tried toys on his own and has managed to touch it himself but it is very hit and miss
As we always say, everyone is different but we definitely enjoy it
I know this post has been up a while, but thank you for this advice. My husband is pretty open to things but has been hesitant on prostate play. We’ve done it once before and he liked it, so I don’t know why the hesitation other than the stigma around it.
Worth adding that you can apply pressure to the prostate externally, pressing on the area between the testicles and anus. Worth a try for anyone squeamish about internal stimulation. Wand vibes work great for this too.
I’ve been reading up on different techniques and that was one it suggested before penetrating, so I hope to try that.
Ok so far more advanced but a metal rod or silicone ribbed sound slipped into your c**k can reach the prostste from inside and give serious stimulation