Go to YouTube, login (no login, and you will be blocked due to adult content), and search for and view the following videos:
Pain Free Anal Sex Guide
Epic Anal Sex in 7 easy steps!!
How to Have Anal Sex: Anal Sex Tips for Beginners
Preparing For Anal Sex
How to Prep for Anal Sex: First Time Tips and Tricks For Getting
Your Booty, Body & Mind Ready
Tips for anal sex | Featuring Dr. Martha Tara Lee
I took note on the steps given in each video, and it seems to serve as a good reference.
18ā?!? Are you hollow?!? Thatās impressive
Yes when you go deeper into them areas you have to do a full cleaning so cold water douching to help speed it up and plenty of it plus better to not eat anything for a hour or two beforeā¦ quite the chore to get through really and sometimes belly feels a bit weird afterwards 
I am not really sure where it actually goes, which is disconcertingā¦
the first time I wasnāt expecting to go that far, but it just kept going and goingā¦ looks damned hot though 
It really is a process when it comes to figuring out what works and what doesnāt. Some have mentioned their capability varies day to day and I agree with that.
It took me a few years, yes years to figure out what works most of the time and to get what my body was ok with that day. When I was 18 I dated a guy I really liked who was in his early 40ās. The first couple times we had sex he spent a lot of time eating my asshole which was my first experience with that. He tried sticking a finger up there those first couple times and it was a no go. We went out to dance one night and I drank way too much. As we were dancing he made his way under my skirt and fingered my ass while we danced. Complete change from the tightness I felt the first couple times we hooked up. We went home and he fucked me in the ass all night and thatās no exaggeration. A couple days later sans excessive alcohol and after a while of trying and warmup he couldnāt get in. Over the next couple months I realized when I drank I was good but sober I was not.
What I learned after that was it really had nothing to do with the alcohol itself. Through trial and error I realized it was all about being confident and relaxing my mind and my asshole. Eventually it became a regular thing after realizing that. As far as size goes start small and I echo the lube sentiment of others. To me, girth is the main factor not length. Most guys Iāve been with are just happy to get inside there so you dictate how deep he or a toy goes.
My girlfriend I thought was fingering my arse but pardon the pun was fisting me loved it I try and fist myself just canāt get the angle right any suggestions
My partner asked me if we could try anal a couple of years ago but we made the excited mistake of not stretching my asshole first and him just trying to go straight in (with lube) needless to say it was too tight and painful and we had to stop and steered clear until recently.
A few weeks ago he started fingering my butt during sex and Im pretty sure its a hint that he wants to try again. Im also keen and so I got a beginners anal kit and an 8" dildo with slightly less girth than my bfs penis. He doesnāt know yet but ive been using both to stretch my asshole in preparation. As soon as the time is right im going to get them out and weāre gotta have a whole lot of anal fun this time! 
@playtim1 You should ask him if you can try it on him first, might give him an idea of what it feels like on the receiving end so he might be more gentle. Did you get a strap on with the kit?
I didnāt get a strap on no, but I might ask if heās up for trying it and I can order one. Good thought actually! Would be fun to be the one doing the fucking for a change!
Also he wasnāt being rough the first time, I was just too tight. With the butt plug and mainly the dildo Iāve learnt how to relax as I lower onto it. I can take the full 8" fine now so its just the extra girth iāll feel with his penis but I know how to relax now. Definitely done my research this time
You should ask him, from what i understand a prostate orgasm can be awesome.
Besides a bit of girl power would feel great.
Haha!! Defo a little different a finger from a fist 
Hmm with the angle your pretty limited when it comes to self fisting unless you give some them fist toys a try.
Hey on the subject of anal , has anyone here done double penetration? anal sex and a toy for vaginal . Any advice or thoughts on this would be welcome. Thanks.
Done it the other way round.
PIV with a toy in her ass.
It tightened her up significantly and she always came harder with a toy in her ass.