After coming out to my wife as bisexual, something I wasn’t hiding from her as much as never really addressing with myself, the only thing she was concerned about was not being able to meet all my “needs”. We talked about pegging and she came around to the idea, deciding it would actually be a turn on for her whilst satisfying at least some of the rest of my sexuality. Great! The question is now though, what next? I don’t want to get hurt or injured by myself or her, so how do I properly prep myself to being used to being penetrated? Also this something that’s best done on my own until I’m comfortable? Should I get special lube etc?
If you have a search (I’m not sure where they are located) there’s a few guides on getting into anal. (Ah have a look at this https://www.lovehoney.co.uk/sex/buyers-guide/first-time-anal-sex-guide/)
They all generally suggest to start small and always take it slowly. Clean yourself up and start with some lube and a finger, you can slowly progress to two.
The lovehoney basics anal proper and anal beads should fit without much issue and get you used to something being inside. It’s easier for the pair of you to go slow and judge how things are going with hands / toys than a strap on (to begin with at least).
Lube wise make sure it’s compatible with toys, so normally water based.
We find the menthol lube by first it really good, but yet to try the others if you wanted a more normal lube.
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All of those things! Yes to lube and yes to practice. In terms of prepping, make sure you are clean, douching can help but isn’t essential. A nice bath can help you feel clean and relaxed.
Be prepared for it to be a learning experience for both of you and something that may not click straightaway.
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Hi @JGHunter good on you for fronting that I bet you feel better.
All good advice above, as for prep the best way I have found is:
Not too hot and not too full but clean out until happy.
Lube is a must the thicker the better and water based. I have used:
https://www.lovehoney.co.uk/product.cfm?p=32745
And
Both very good handy to have a pump for easy application. Don’t go made with the numb element, good to relax but you want to feel so you know when to stop.
Best advice, take it slow, lots of lube, listen to your body if it hurts stop.
For pegging maybe this would be a flexible bit of kit:
As it can be used with all types of attachments.
Hope that helps, good luck! 
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I prepare for a pegging session by wearing a well lubed butt plug during our foreplay.
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It can also help clean up if you use a condom on the dildo.
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So first of all congrats on addressing/accepting your sexuality. The next thing I want to just throw out there and thats you may find you don’t like receiving anal stimulation, not everyone does including bisexual and even gay men. In my opinion when it’s done right it is fantastic but just don’t feel a expectation to like is my point.
Now for prep if you have high fiber diet and are regular going to the toilet and having a shower can be enough. If not or you’re concerned about it, a douche is a good thing to get. You don’t want to use it to much as over doucheing isn’t good for you but 2-3 times a month is ok. Go with barely warm water not to hot or to cold. I find the most every really needed is filing the douche bulb twice at the most. If you do go with a douche to clean, you want to do that 20-40 minutes before you start play.
You want a really thick water based lube(silicone if you are using glass or metal toys anything else is water based only). LH discover is great, it’s labeled a anal lube but it’s basically just a super thick water based one so it can be used for all types of sex.
Start slow with something small and use lots of lube, circular motions are great as well. A little discomfort is ok but pain is not, so any pain stop and add more lube or go back a step etc.
You have a few options for toys, you could go with a small starter dildo or a small p-spot massager or a plus trainer set it’s all just a matter of what you’d like to start with.
Lastly as for whether it’s best to be done alone or not that is strictly up to you and what would make you the most comfortable.
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I always start on my husband after a relaxing bath. First of all I live up a small butt plug and work it into him slowly. I leave it fully in place and then slowly pull it out repeating this a few times ensuring that there is plenty of lube. I then step up in size repeating the same process. I have three different sizes and by the time I’m finished my husband is gagging for the strap on. It’s all about anticipation so I slowly get the strap on ready to wear and lubed. I usually take him doggy slowly. He’s ready as I always slides in smoothly. I finish him off with him on the edge of the bed an in missionary position. Where I can masturbate him with both hands whilst still thrusting. He has the most intense orgasms. I hope my advice helps you get started and tell your wife that she will really get off on the dominance of what’s going on plus my man says he loves to surrender to me.
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Hi, sorry it took me so long to reply, thank you for all your responses! I made this and completely forgot… but that’s December for you. Seasonal stuff just gets in the way.
I bought these late in 2019
This was around the time our marriage went off the rails a little, so it seemed as good a time as any to confront my sexuality and accept what it was and then tell my wife. If it was too much for her, that was the time for her to find out and we’d go our separate ways. Thankfully we didn’t! Anyway, she happened to have booked to go travelling with a friend for a few months earlier in the year so I had my own place and it seemed a good time to experiment with myself. I got to the point where I was able to just about use the middle sized one. However, after she got back, lockdown happened and I haven’t really had time to myself to “experiment” or get accustomed to anal play so I think I lost what little progress I made there. I did notice the gel lubricant I got seemed to “disappear” fairly quickly.
@Davy_Brown I may well get that shower attachment, it seems like a lot less hassle!
@rockstar I would like to be in a “position” wear I can wear a butt plug for long periods even when not preparing for sex, so it seems more normal. I have heard of people doing this, even just on the weekend lounging around the house.
@FindingLibido The idea of using a condom certainly sounds like it would make cleaning up that much easier and hygienic!
@Enchantress29 As an almost-completely-vegetarian I do have a high fibre diet 
but I will still get a douche anyway. That’s one thing that really unnerves me, so even if it’s a little unnecessary the peace of mind will be worth it. As mentioned above I did enjoy anal play with myself, even if I might have pushed myself now and again too far and it hurt, I knew the reason, rather than feeling it wasn’t for me. I could stick it on a hard floor, put cushions either side, and kneel over it and “ride it” and it created a far more intense orgasm when I was done, so I’m pretty sure I “have it in me”, so to say. LH discover is the one I have, as mentioned above 
other points you raise I think I’ve responded too as well.
@Love_Stud_Too we have actually talked about how we’d do it, positions etc, as dirty talk during sex and she really gets into it. She was a little bit “oh” when I first suggested it
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Good luck
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I need more information about this lar time I rushed it