How often and for how long do you play with anal toys?

I would love to have my butt played with much more often

Just need to offer an update to a previous post or 2 in this thread. My wife is now retired so my enema time is severely limited. This past Monday when she was out to dinner with friends I jumped at the chance to give myself several enemas for the first time in 3 weeks. At the end of my enema session and time penetrating my ass with 3 dildos mounted on the shower wall, I inserted my 12" double header with the intent of leaving it in overnight. Well, it's been in continuously for 74 hours. I have taken it out twice to add some lube. I can't count how many other times I've taken it out to put it right back in and out again and in and out... Yes, I'm playing with my ass.

Two things I know: 1. I have to take it out during the day at least every few hours just to pee. It must press on my bladder just right as I cannot pee while it's completely in. I've now gone those same 74 hours with my anal playground remaining completely clean. I've yet to find the first hint of a dirty playground. It's not like I haven't been eating; but, it's staying in tonight and I'll see if the playground is still clean in the morning. My favorite 12" double header isn't coming out until the playground needs cleaning again.

The point is I'll play as long as I can.

Well today started of very well and it began last evening. I just got a new Njoy 2.0XL plug and been playing with it the past 4 days. I really like it. It weighs 22 ounces -1 pound 6 ounces. That's a carpenter framer hammer weigh. I tried sleeping with it in the first day but it was too distracting to really sleep so I stopped about 2 hours after going to bed. Last night I had it in till 3-took it out for a wee and then feel asleep and put it back in about 430 and slept again till 7 am. I then decided to try to get this new mega plug up my butt first thing this morning. It is just shy of 3" diameter and its silicone and only flexes a little. I have the 2 1/2 XL version and that is doable and I used it as a warm up along with a 12 dildo that is also the same diameter as the plug but is a more flexible material. After about 30 minutes it snapped into my ass forcing its way in around my sitbones. I was terrified it wouldn't come out so after I removed it today that was the only attempt. It was a success and that thing is definitely the bomb.

I like to play a bit everyday in the morning before the day begins its solo and no one is around to stop my entertainment but I'd love to have a playmate in the not to distant future. In the meantime I have an awesome arsenal of anal delight to attack my bad ass.

It kind of goes in waves for me - for some months I'll be doing it 5-7 days a week, then other times I'll go for weeks without anything. When I'm in an almost daily routine my sessions are longer, usually 1.5-4 hours but longer on occasion. I also get into buttplug wearing when I'm in one of those phases, and I'll wear them almost constantly with just a few hours of break during the day.

When I'm in a phase of not doing it too often I do it more to heighten orgasms rather than just enjoying the anal, so typically just 15-30min of butt fun then I blow. When I am in one of these phases I often won't bother toying myself at all because of laziness. I end up just fantasising about using my own toys and always feel lazy and kind of stupid after LOL, "why am I imagining what this feels like when the toys right there?"

My wife and I started pegging about three years ago. For more than two years now, she pegs me every time we have sex (about 3x per week on average). She loves me going down on her and this is how she cums. We will usually engage in PIV for some period of time before she pegs me. The reason that pegging is always part of the mix is because my orgasms are so much more intense when I'm pegged. I love it, and she really likes to being able to see me have such incredible pleasure. I often rim my wife (contributes to her having more intense orgasms as she often rubs her clit while I tongue her ass), so I think she fully appreciates and is comfortable with anal play. We mix things up a bit when pegging through the use of different dildos. Less frequently she uses a handheld vibrator (Lelo Billy) on me while giving me a blow job. It's funny to think that I had no anal activity in my sex life (including masturbation) until three years ago, and now it's part of every single episode. Wish I had jumped into the fray much earlier, but happy to be hear now.

I like to do anal play when ever chances are there, and as long as I can enjoy it.

Occasionally I'll get a strong desire to have something up my butt. My wife is very accommodating. 'Occasionally' these days means every few weeks or a month apart but when the urge hits it is strong! Years ago this was a usual part of our sex play maybe a couple times a week. Once on a cruise we tool a double headed dildo and she did me 5 out of the 8 days. She would use one end in her pussy and the other up my ass. She now has a corset style strapon harness but looks really hot when she wears a pair of tighty whities and slips the dong through the fly. Usually on this state of mind I want a hard fuck, just line it up and push. That initial stretching pain is exquisite and I like her to fuck me right through it. Our sessions go on for up to a half hour or until I cum.

We also use butt plugs. The soft classics and we have a couple of fancy glass types (medium size). I have worn the hard glass in me for a couple of hours. If were not playing together I can work on myself. Again, I love the initial stretch and the little pain that usually comes with it and I'll play maybe 15 minuets to a half hour especially if I'm in the shower.

So, how often? Maybe every 4 to six weeks but varies on my state of mind. How long? Perhaps up to a half hour.