When my OH decided she was going to try anal sex she and spent 3 months stretching first before we tried, she used a variety of gradually larger plugs and dildo’s, she would wear plugs for hours so she was comfortable with something in her bum and she stretched to a size that was bigger than my cock so she knew she could take me hopefully easier, which Im glad to say she did, after around 10 years of an active anal sexlife she can now, with plenty of lube, take me with no pre-stretching.
From my own experience I had an active sexlife when I was first experimenting with my sexuality, plenty of female and male sex, the first gay sex I had I quite naively went straight in to it with no practice and very little in the way of lube, I can remember it not be pleasurable and very uncomfortable the next day, fortunately it didn’t put me off gay sex and I learnt to take it slowly and use lube.
Now I’m a happily married Bi man and I still love anal play, I do more large toy stretching now but its still the same recipe, plenty of patience and lots of lube.
This is something I want to start with my husband. I’ve had anal before over 10 years ago (with someone else) and I didn’t like it, too painful.
I’m ready to try it again, the thought of it turns me on I keep looking at butt plugs to buy. I think I’ll just buy one and give it a go.
Not sure about pegging though, my husbands never mentioned it. Maybe I’ll bring it up. 
All these replies do give me hope now because I thought I wasn’t making progress, my butthole is getting more elastic ( and it does bring me joy because I am going to stop at a certain width and not extreme I just want a little more ) Im trying all day to get my large glass plug in.
Thank you all for the advice and opinons Ive been so busy im gonna get back to you all, so sweet and lovely souls and kinky just like me mwauh <3
Communication is key, bring it up. One thing you learn is people will do all kinds of things if they feel unsatsifed, or they want something and are embarassed to ask… do it inquire its better than leaving the topic alone. Always communicate your wants and needs. That way they are satisfied and you are the only woman for him <3 good luck babes
Anal was hard for me at first too, I started enjoying the feeling a lot with plugs, the deep feeling even after some time still getting use too but my butt is elastic(er) not in a bad way in a reasonable hot way that I can warm up with my largest plug and it doesn’t hurt anymore he he <3
My first experience I needed to do it by myself with a small silicone plug because I was scared too honey buns, I remember the intense pain when it popped in and I wanted to take it out so bad, I decided to wait about 45 seconds.
It shifted away and I got great feelings and then I said okay with a little more time I can do full penetration with my partner, I am glad I started and tried it, because now I love it.
For men it must feel even better for the prostate ! but yeah it just sucks because it effects your appetite you need a routine, clean yourself etc etc
Wow omg this gives me such horny vibes right now, when I tell my partner he’s gonna be happy!
We we’re starting to lose hope that there was just a limit for my body I guess, but I will keep at it day by day thank you.
I have big plugs just waiting for me, tunnel plugs, and oh the speculum is so intense and was scary for me anally at first
my partner calmed me down and the sex and photos was intense and hot though!
We have been having anal and pegging for over seven years.
Started with me seeing anal porn and said to my husband that we should try it. LH butt plugs of various sizes and anal lube was purchased and we started practicing. Difficult to relax at first but soon started to go up in size with the butt plugs. Having PIV with a butt plug in was fun and helped me relax. Then came the day he popped my anal cherry. Lots of lube and a gentle push and he was in my bum. It was an amazing feeling.
Afterwards I said that I was now going to train him so that I could give him a good pegging. He didn’t need any further encouragement and now we do each other regularly.
Ps he loves seeing me walk around the house wearing my butt plug tail 
Started with anal play about 20 years ago . We bought a top shelf harness that came with a large and giant butt plug . Rookie mistake . With much lube and much work she managed to get the less big one in . It was mildly painful . We purchased a tee plug and a number of dildos . She no longer participates but my desires are still there , so it is self service . I think I have four prostrate massagers ranging from modest to pretty fat , they are OK . For me it does little for me to stretch out . Some of my smaller dildos along with my tee plug are where I always start . Interestingly enough only two things have given me prostrate orgasms , my remote egg and my largest dildo . Here is my biggest , at least until I finally pull the trigger to buy the Dragon monster that @Melody1 showed above .
Lifelike Lover Ultra Realistic Suction Cup Dildo 9 Inch - Lovehoney UK As a note for taking the longer toys , it is all about prep . I always start with my trusty old tee plug to get the lube in and relax before taking larger toys . I generally do not wear butt plugs for extended amounts of time . I must confess I do desire anal play often , I would like to have the better part of a day to play with all my toys , undisturbed .
I have that ‘lifelike lover’ too. 
It’s good!
I dearly want the dragon dong dildo , but I think my wife might freak out . The thought of riding that and especially videoing it disappearing in me makes me a horny anal slut .
I understand the horniness I do, when I get that way I can get frisky and think I can take on the whole world and crazy sizes that I can’t ! LOL but yea, my partner was a little nervous to explain to me that he liked the feeling and basically I guess corrolated it with It makes me happy we should try it together I think it could make sex even better for us (it did, I can say that <3 ) so awww I wouldn’t feel like that. I didn’t look at him crazy. It’s nice when you are on the same page, maybe try something a little less freaky to acknowledge her with it and guage the waters LOL but I want the best for you
I’m new to trying anal and wow I’m enjoying it. My only hesitation is how can I make sure I’m clean.
Sh*t happens. Some folks like to use an enema to wash clean, but it really isn’t necessary. If you’ve showered it’s probably fine. When I’m playing by myself I put a towel down under just on account of the amount of lube I use. Anal with my wife is usually quite clean without any special prep - I always wipe my penis with TP afterward as lube and poo get runny and not always easy to see if it’s dirty. Usually wipes brown and that’s fine. Once that’s done I hop in the shower to scrub it with soap and rinse off. No harm no foul.
He says it’s fine and I’m clean but it holds me back thinking I’m not I just want to make sure. We’ve dabbled with a butt plug a dildo and hiimself but he says for all I seem to enjoy it I never let him all the way in. I just need to feel more comfortable because the feeling is amazing
What plug would you recommend for a beginner x
I’m new to Anal sex at 47 how can I make sure I’m clean any tips
When i ride my butt plug i clean myself using a shower attachment to clean anything out, also knowing your own body rhythm helps, try using a classic medium butt plug to start with, and lube
The dildos she uses on me are 8" and 10" long so even douching doesn’t clean that far up.
We just go for it spontaneously and if there is any mess we deal with it.
Absolutely 100% agree.
We started experimenting with anal training my ass since our late teens which is about 15 years ago. We started with a medium sized buttplug with the intention to train my wifes ass for anal.
But how the tables have turned, since the first time that plug was used on me I was hooked, and I was on the receiving end most of the times and have quite an extensive toy collection now.
Over the years we slowly worked up to 10+ inch circumference toys ass and anal fisting.