Hi there, I am new to lovehoney (super glad I stumbled upon it though) and reading through it seems maybe I can get an answer to my question. I have been pegging my guy for a while now, we both absolutely love it! But I’m not sure if I’m doing it right lol. I mean we have six different harnesses, several toys all sizes, costumes, wigs, we have advanced to ten inches and there are times we play for 3-4 hours. Never had he orgasmed from pegging. To me this has become a challenge which has robbed me of some of the fun. I know there is no wrong way of doing it yet I read posts and see porn and these men have the most intense orgasms and I want to give that to my man!!! Are we just trying to achieve something unrealistic? Am I trying for something I don’t fully understand? Don’t get me wrong, we are not going to stop. I don’t know, any advice, feedback, etc. appreciated.
There’s a good thread on prostrate orgasms on here that may help.
A summary of it is that that type of orgasm is elusive and needs, time, space and relaxation and a lot of experimenting.
The main thing is that you’re both having fun rather than getting frustrated and making it about the journey not the destination.
There’s all sorts of subtleties at play and sometimes all it can take is a small shift in angle or depth to get the magic going. The other issue can be that when you get the right spot the sensation can be intense and bordering on painful in a way that can be scary!
It can be tricky to get right. We’ve found it took a lot of practice (good thing!). Try to not let the pressure of achieving it bother you both, as that will make it more difficult. Have you tried a vibrating toy?
Here are a couple of topics that may help
I’m a newbie when it comes to pegging, and our sessions are no way as long as yours! But so far while I find the sensations fantastic, and very intense they have had a different quality to them and seem not to lead directly to orgasm on their own. My wife (or I) have to help things along usually by ‘manual handling’. The release is extremely intense and often leaves me seriously wobbly at the knees. I would like to get to a ‘hands free’ orgasm, but am really enjoying the journey to get there!!
Size wise we have worked up to 8.5 inches and definitely prefer the ‘cowboy’ position, as it allows me to adjust angle and depth, and gives us both access to my cock.
As for costumes the current favourite is the Sexy Nurse which works so well with her Strap-on, the dress hides the straps and makes the dildo even more lifelike which plays very much into my fantasies!!
I doubt that it’s anything you are doing wrong. Anal or prostate orgasms don’t happen to everyone.
I have been pegged regularly for a long time now and also indulge in lots of other types of anal play but, although I’ve come close, I haven’t orgasmed from anal stimulation yet. That doesn’t mean that I don’t enjoy it. In fact being pegged is wonderful and I crave it constantly.
From the reading I have done it seems that being able to orgasm from prostate stimulation is something that can be learned so perhaps it’s something you and your partner or just your partner alone could practice alongside pegging.
Don’t over think it. If you are both enjoying it then you are doing it right. If you can do ten inches that’s really impressive .
As above, there are more specialist toys designed for encouraging prostate orgasms
Hey welcome to the forum and great first post too 
I’d say as everyone is different, it’s more about exploring to discover what makes it more intense for him. Bare in mind also that many porn videos are acting and the people in them will go to the limits of making an orgasm seem 10x greater than it really is… but that’s not to say it can’t be achieved with the right mix of stimulation both emotional and physically.
Hey and welcome to the forum, me and the OH partake in a wee bit of pegging occasionally
we too have various harnesses and different size dildos, it’s quite normal for me to go completely soft whilst being pegged and I think this is down to the stimulation all being around my anus and not my cock, it doesn’t mean I’m not turned on, just in a different way, depending on the position we’re doing my OH often has to stimulate my cock to get me to cum but we have found that if we use a curved G/P spot dildo in her harness and again depending on what position we’re doing, curved down for doggy or curved forward for me on top this stimulates my prostate and I leak prostatic fluid constantly even if my cock is soft, known as prostate milking, it’s a weird sensation, almost like a peeing sensation mixed with a constant mild orgasm and it looks amazing.
Has he made an issue of not cumming from pegging stimulation alone? Or is this just you worrying your doing something wrong? If he’s enjoying it and has no issue with you having to finish him off then I don’t think you have anything to worry about. There are plenty of pegging videos on the net and very rarely do men cum when being pegged. To be fair when I have had anal sex with a man I also never came during the sex if I was the one being fucked, would always need cock stimulation to finish me off.
Honestly think you have nothing to worry about if he’s enjoying the play! Plus you must have some stamina! My OH cant never go for 30-40 minutes let alone 3-4 hours!! 
I’ve never came via pegging yet. I don’t think its easy to achieve. Still love pegging tho. Cumming isnt really the point, would just be a nice natural end point, a very visual sign of progress, but it feels as good either way.
Thank you for sharing!!
Everybody’s replies are on the money . It is rather difficult and rare for me to have an orgasm while being pegged or other anal play . I have found I can produce a lot of pre cum while being penetrated and who does not like the taste of their pre cum . Enjoy the ride !
You are all amazing!!! Thank you so much for the feedback! He has no complaints whatsoever, it’s just me! I tend to be a bit of an over achiever!
To be fair @Mommydommy I can more or less guarantee he’s more appreciative that you are prepared to peg him as there’s not many that would even entertain the idea of pegging their OH regardless of what they want, I have a female best friend who knows all about my pegging and she can’t believe my OH would do it as she said if she had an OH who suggested pegging and anally playing with him it would be a no way, never.
I really love a dildo in my ass when my wife sticks it in. She’s not big into toys but that’s ok. My erections are not the best as I get older. I have a hard time putting my cock in my wife. We mostly have self satisfaction sessions which we have a great time, but I’d like to be totally hard again. And I don’t want to take the ‘little blue pill’ to get it.
Try a metal cock ring though getting the right size is tricky asa lot are too big think mine are 40-43mm
@Mommydommy that’s awesome that you are so into it and looking to improve, your S/O is a lucky man. I wouldn’t say pegging him correctly, as I think as long as you both enjoy it, use plenty of lube that’s the only requirements for doing it “correctly”
Based on my experiences, I’ve had about 12 women peg me (currently trying to broach the subject with my current S/O). Everyone is different, but I’d suggest trying out various positions and see what works best for your S/O. My first girlfriend that did pegging with me was kind of the same way and wanted to see if she could get me to orgasm just by pegging me, and it honestly put some pressure on both of us and for a month or two couldn’t achieve it.
I’m a bit OCD with prep for obvious reasons, usually I will give myself a couple of enema’s and a good shower first, this particular day I went the extra mile and had a colonic cleansing the morning of and showered well when I got home, then put in a but plug to stretch myself out a bit and relax. That afternoon we had a planned an extended session (got to love snowy Saturdays in Colorado) We drank a little wine, had a little bit of pot and were both really relaxed…we also both enjoyed playing dress up, usually wearing similar outfits, so initially we were both wearing stockings and garters, crotchless thong panties, mini skirts and blouses too. She always loved reverse cowgirl because she loved to watch her strap-on slide in and out of me so I pulled out the BP and we started out with that with her 8" vibrating strap on. She almost always comes from that and it didn’t take long for her, but I still didn’t cum from prostate only. We had also done a bit of shopping the previous day, since we were both interested in something a bit larger and ended up picking up a 12" dildo that didn’t vibrate, that was also a little more girth, at almost 2". Since it was a bit larger we started out in reverse cowgirl again so I could control entry and eventually was able to slide all the way down and she loved it even more, making a joke that I must be a size king/queen lol. I rode it for a bit in that position, but we had a new position we wanted to try that we both liked with vaginal sex called the butter churner. We both were taking yoga classes together, so I was fairly flexible but the harness didn’t allow the dildo to go at such an extreme angle so it was a bit more of a flat butter churner position. We had a smaller bean bag that we put under my back too which helped a bit. Needless to say, the extra pressure this position put on my prostate was noticeable as she slowly slid into me. A bit more lube with each initially thrust and she started pounding away pretty good and I was rock hard with no stimulation from her or myself. I started to tingle and knew I was about to come and moaned that too her and she started pounding even harder and I had one of the most intense orgasms ever…needless to say a lot of it blasted me in the face and hair and I didn’t care. She kept going and started cumming too and that sent me over the edge again, having another orgasm…and another until she finally stopped because she was ready for a break. We took brief cleanup break, but I wanted more so gave her a break and I rode her in cowgirl position and wasn’t even hard and came yet again.
So without a doubt I think it helped due to a few things, for me mentally knowing that I was 100% clean prior, and the extra prep with the BP helped a bit. I think a few glasses of wine and pot helped us both relax and not worry about the prostate orgasm, but just enjoy the ride (pun intended) helped too. I think the increase in size helped a bit too, but in follow on sessions I was able to have prostate orgasms with smaller dildos, I just prepped the same.