Hiya, my long term boyfriend has told me he wants to try pegging. Anal play talk came up about 2 years ago and I expressed how I didn’t like it (particularly receiving - bad experience -, but never tried giving) so he usually uses his ‘free time’ to do it himself. We both like switching between sub and dom, so we usually have power play in the bedroom, so I understand (and he explained) he just misses anal/prostate stimulation.
When this came up recently I was very emotional because I really did not want to (I told him this, and he says he feels it as a want not need so he’s okay to not do it), but after reading a lot I’ve kind of come round to the idea. We both really enjoy giving each other pleasure, and I can see myself enjoying using my dominant side to look after him like that, so that’s how I’m starting to see it.
I’ve bought a strap-on so that I can kind of try it on to see how I fee wearing it and so that’s it’s there ready when we want to try it. I know how I’ll approach the subject when the time arises (he doesn’t know I’ve come around to the idea), but I was wondering if I could get any tips (from men and women) on how to make the most of our first experience. And maybe if there are any other couples who like to switch between sub and dom, could you maybe talk me through how frequently you use pegging and what it maybe has brought to your relationship please?
If he’s experienced in anal play and will be able to take the dildo with no physical problems then it might be nice to surprise with the strap-on by being the domme and ordering him into whatever position you fancy and pegging him as your sub. That does it for me every time.
just be honest with each other.
don’t just be like surprise I want to give it a try.
he needs time to prepare.
as for us we have been doing it on and off for 19 years.
but it haves been a regular thing for us for the last 3 years 50% of our playtime is pegging.
and we love it.
anal is something everyone needs to prepare for.
it’s fun and very intimate.
but if your not ready it can be messy and weird
I say just surprise him one night put it on before he comes to the bed and he will so happy he won’t be able to contain him self 
I dream about my miss of doing this for me and everything else will fall in place
I agree with @Peggingand_fun , maybe tell him several hours before your domination , not only will this make it more clean fun but his anticipation will be greater . When my wife is dominate , she tells me what to wear also and that adds to the atmosphere . I also enjoyed my wife "making me " kiss her and lick / suck her tits and eat her to an orgasm before she takes me . Yay for you and him !
Plenty of lube and take your time with him. Going slowly and teasing will add to the anticipation.
Condom can help with some of the hygiene side of things but giving him some notice means he can clean and prepare himself.
If you know he is going to have some “self time” then you could walk in on him wearing your strap on, he will probably think hes won the lottery lol
Thank you all for the advice. I have talked with my boyfriend today, and he seems very excited about the possibilities. I am also very excited.
We talked for about 3 hours just laying all our cards on the table, talked about our traffic lights (our way of checking on each other) and what we both want from our experience.
He has explained to me that he has never experienced an orgasm just from anal/prostate stimulation, and he says he doesn’t think it’s a possibility for him. Please can a male shed some light as to whether they only experienced a orgasm like this during pegging, or is it normal to not get an orgasm just from anal play?
And if there are any more tips on how to make it more comfortable for both of us, or to help me with any kind of forwarnings on what could happen whilst I’m wearing the strap on that would be amazing
I have not had an orgasm from anal alone but the combined is 100 times better it’s like a clit and g spot orgasm at the sametime I’m guessing.
just start slow and communicate before during and after.
maybe put the strap-on on before the forplay even begins get used to how it moves make it part of the fun and get comfortable in your new roles.
and have fun good luck
G spot orgasms are amazing but they won’t happen all the time.
Some very good sound advice can be found on the interwebz. Most important thing is to just have fun with it 
Totally agree with what everyone has said with regard to pegging for thr first time. Slow, steady, patience and lots of lube. Your BF will be wanting you to go at it from the off, i know that because i did when my wife and i started pegging, because wife was new to it too she had to find her rythym. Go at the pace you want first youll soon find what works best. Looking forward to hear how the first time went for you both, enjoy !!!
I suggest getting a regular sized dildo first that is harness compatible. Also plenty of lube, don’t be scared to reapply if needed because the anus does not self lubricate. Go slow at first and work your way up. This is what works best for me every time.
I always recommend the XR University episode on pegging as a good place to start as they talk through it all and then give a demonstration with commentary to explain what’s going on with things like position and movement.
For me pegging has given me a greater appreciation of my partners experience of being penetrated and the dynamics involved.
For the first time as with any first time it’s important to be relaxed and not expect it to be great immediately. There’s lots of learning for both participants about what works and what needs work.
Focus more on having fun exploring and once you have the basics ready then you can explore the more sub dom elements of it.
I thoroughly enjoy all forms of anal play, plugs, vibrating toys, prostate stimulators and especially pegging but I’ve yet to have a pure prostate orgasm. It’s lots of fun trying though.
I have never had a pure prostrate orgasm . However I have had the largest volume of precum ever . Imagine you will both “enjoy the ride” .
Well done for chatting through and being open and honest. 
Pegging will allow you to take the Dom role in any direction you like, so enjoy it. If you’re a little nervous, make him wear a blindfold as that’ll take the pressure off you. You could also tie him down so you have complete control.
If you’re looking for the illusive orgasm, I’ve found this rarely comes when you want it to and more likely when least expected so don’t worry if it doesn’t happen
Being honest and open is 
in every relationship, about anything.
First time, My wife started with a nice sensual back massage which led to butt massage, rimming, anal play then finally pegging! It was incredible, I didn’t cum from it so after my wife was done fucking me, we changed the power dynamic and we have sex.
Also you don’t need to be the sub to be fucked! Women get can be Dom and demand that cock so you can switch up, strap-on on or off, also, we could try wearing it, would leave him fresh for round 2 
So we did it!
We both enjoyed it, although my legs don’t like me much this morning… we did missionary so I was on top, credit to the men and women who use this position frequently!!
Although we both enjoyed it, he didn’t enjoy it as much as he expected so we have both decided it’ll stay on our list of sexy things but it won’t be all that frequent. Before getting down to the act we tried a bit of finger and plug play, which he says he actually enjoyed more. I guess people never know until they try it!
Thank you to everyone who commented and helped!
Hello Everyone, I am the partner of Daisy0211, (who you all helped to get pegged).
Thank you all for being supportive of Daisy and giving great advice, she showed me this thread on the Tuesday after it went up (a couple of days after initial posting). We both went through it and discussed the advice we got together and picked out what we thought the best way to go about things were. By doing so we both build confidence in each other by discussing the event and how we wanted to do it. We also took baby steps sort of speak by trying the position without penetration first, then with clothes off, and worked up from finger to plug to full play (over a weekend).
We certainly both enjoyed the fun and had some laughs along the way too! It’s not going to be a regular staple for us we think (being both switch) but when the mood hits us both again we hope to revisit this fun topic.
Thank you all again.