Interested in Trying Anal, but Lots of Questions

My wife and I have been married for more than 12 and a half wonderful years. We have a great sex life, and we usually have sex around four to five times a week, sometimes more. Lately I've been looking up ways to get her to orgasm more easily, and a lot of people are saying that anal sex is the way to make it happen.
She and I have never done anal. We've both always thought that it would be nasty, so we've always done it other ways, usually vaginally. But as I've been reading more and more about anal sex (and pegging), the more interested I find myself in both giving and receiving anal with her.
As I've discussed it with her, she appears to be also mildly interested. But I'm going to have a lot of questions about it, because I've never really thought much about it until lately. For example, if we try pegging, how can we be sure that she'll "find" my prostate?

 

I would encourage exploring pegging on your own first. Will help u figure out what u like and help wife ease into it. Just my thoughts.

 

Oh and get a good cleaner for the toy

 

I have a glass set w 3 sizes and I luv it! The small one is comfortable enough to wear all day long. I think a set like that is a perfect place to start anal play. Also lots of lube!

 

Haven’t done the all day thing yet. Do u still get the sensation without discomfort? Is it just a plug or does it vibrate?

 

I rarely get discomfort anymore. I honestly forget about it sometimes then I'll move a certain way that give me a pleasurable sensation like "oh yeah!" like a sexy little secret my coworkers don't kno about. It's just a regular plug

 

Will have to look into it. Thanks for sharing!

 

Damn that sounds hot

 

Wow, great response. Thanks for all the suggestions. My next question was going to be about how to prepare, but that's already been delved into. Glass butt plugs? That would kind of freak me out. lol I've read that a plug should be used about an hour prior to beginning to play. Is that about right?

 

I'm interested more in pegging right now, because I anticipate that that's how I might convince my wife to try receiving. If she pegs me and I enjoy it greatly, then I have to imagine that she'll want to try it and feel what it's like. So, next question: Can I be pegged if I'm in a standing position? For the first time, I'm envisioning being on all fours. Any recommendations regarding positioning, either first time or more times?

 

Rheeglenn: The best position for us is with me on the very edge of the bed and her between my legs. I can rest my legs on her shoulders and watch her hips move while she fucks me. Our height difference does not lend itself to standing. Hope that this helps.

 

Yeah, that sounds like a good one too. What's the best kind of lube to use, that you've found?

Also, I've read all about how never to go from anal to vaginal without cleaning up in between, but what about from vaginal straight to anal?

 

I haven’t tried pegging but definitely try you in her. I wish I’d tried it sooner. It’s fantastic

 

Awesome. If you don't mind my asking, how old were you when you first tried it? I recently turned 38, and if this turns out to be anything like what's been described to me, I'm going to wish we'd tried it much sooner as well!

 

Okay, all you experienced anal-players. I just read an article that warned that, on the day after having anal sex (or pegging), the receiver may experience painful and/or loose bowel movements. Is this something that can be expected to occur after EVERY session of anal/pegging, or after only the first time or so? This is really important, because my job often requires me to be more or less the center of attention on a daily basis, and I need to avoid potentially embarrassing situations. How has this aspect played out for you?

 

It's never affected me. I can't quite recall from the first couple times I did it as that was about 16 or more years ago but I don't remember any bowel issues. If I feel like I need to have a movement and still do it with no flushing then yes, I get the toy dirty but otherwise no day after issues

 

Okay, cool. Yeah, I'm not too worried about that in the first place, but still, I wanted to know what I could be dealing with.

 

So we tried stuff last night, pretty much along these lines. My wife figured that a tampon would be good to use on me in the early going. It's not as long as a dildo, but we haven't bought a dildo yet, and the tampon is very narrow, so it would assuredly not over-stretch me. But because it's not as long, it didn't go very deep, so I didn't feel any euphoric sensation. I told her the feeling is interesting, intriguing. I want to try more stuff, both on myself and my wife using stuff on me, so I figured I would buy a plug set this weekend.

After she did this on me, we turned around and I tried gently working on her. She got on her arms and knees, and I put an abundance of lube on my penis. I encouraged her to relax, and I started to rub first the shaft and then the head of my penis between her cheeks, taking care not to try to enter her anus yet, as I had promised her. The problem was, she kept flinching when I was there, even though I could even see a space between us, so that I knew I wasn't penetrating.

That's all she could manage that first time. I told her that I hope we can try to go further in the coming days, because it's almost like the ultimate trust exercise between couples. I used to think of this as something that was very unnatural and weird--like a bad "weird"--but the more I think about it, the more I'm realizing how natural it actually is.

 

At least u r working on it together...good start!

 

Going to an adult store together would be a good idea. Staff is pretty helpful and u really shouldn’t feel awkward cause trust me they’ve heard worse things than what u r gonna say!