I used to ride my ex'es dildo. Who else enjoys anal masterbation?

Can't go a day with out butt play

Feels good.....Why not do it!!

I often use objects and my fingers. My wife has a huge strapon I enjoy.

Lucky you. My ex would never let me use a strap on on him

I used to always get turned on at the thought of a hot looking woman fucking my ass with a strap on, but at the same time thought I would never want anything in my butt. Then, one day after working outside on a very hot day, I came inside to lay down. My ex-wife layed next to me and started caressing my cock and balls, not to get me tuened on or get me off,but just to relax me. She rubbed under my balls and hot that sensative area leading back to my anus and as she noticed I was liking that she kept gradually moving further back until she was rubbing the outside of my asshole annd it was feeling really good. She kept that up for a few minutes until, without any warning, she slipped a finger inside and WOW! She wiggled that finger around for about a minute and then decided to put some lube on it and put it back in which helped her to slide it in and out asier and she was able to go deeper. She was not intending to do this, just that the further she went she could tell how good it was feeling for me so she kept going and I am so happy that she did. Her lubed finger working in and out of me was so incredible feeling. I never expected anything in my ass would ever feel that awesome. It started out with me laying on my back and after a while I got up on my hands and knees and stroking ny cock. The feeling of her finger sliding in and out of my ass and wiggling around until she hit that spot and I told her to keep rubbing there. It felt so good and I didn't want her to stop. It took longer than makinng my cock cum, but she gave me my first ever anal orgasm and a couple of minutes later my cock shot its load. I was hooked right away and ordered my first sex toys kit for anal play, which was a plain vibrator with attachments designed for anal. One was a about the length and width of a pencil, which is what I started with and was planning to eventually work my way up to just the vibrator itself (C battery size vibe) there were a few other attachments that got gradually bigger, but after I got off with the small attachment, I just lubed up the vibe and slowly worked it in. She said I shouldn't go so big so fast, but it was fantastic. I wound up getting other anal toys, such as an expandable vibrating butt plug, which was difficult to get in, but once it was in there it felt really great. My favorite toy for my ass on most occasions is my slim vibe that is just a regular vibrator that uses 2 AA batteries instead of 2 C batteries. I do have one huge dildo that I use on rare occasions. I have to be in the right mood for that one, but it's great when I am in that mood and get to use it.
I had never even fucked a women in her ass before this. I thought that would happen before a girl would play with my ass or that I would play with my ass, but I am not complaining one bit. A few weeks later she decided to lick my ass. HEAVEN!!!!
My ex-wife did decide she wanted to try having me fuck her ass, but she said it was too painful. Not from trying to doo too much too soon, but because of other health issues she was having.
We did talk about getting a strap-on and having her fuck me with it, but we just never got around to getting one.
Since we divorced, I have had other women who surprised me by fingering and some who licked my ass, some who used toys on me and some have said they would love to fuck me with a strap-on, but being fucked with a strap-on still has not happened for me. I do have a few girls who have told me they would be more than willing to do that with me. Hopefully I can soon knock this fantasy off my fuck it list.

I used to try fingering my ass. I also tried a few different itmes. It felt ok. Then one day i tried a big barrel sharpie marker. No idea why but that was perfect. I came hands free which really blew my mind. It wasnt easy for me to do and i only ever came twice that way. Dont do it anymore but that was sure a hot experience.

Do it about 1x per week.
I insert my anal vibrator, pull my panties up to hold it in place, turn over and doze or go to sleep.
Some time later I become aware that the internal stimulation has made the front of my panties soaking wet with precum.
It doesn't take much manual intervention to change the clear precum flow into squirts of white cum.
Replace batteries frequently to avoid in-flight frustration.

Big anal masturbation fan here. Used to be into it more, doing so once a week, but a leaky battery ruined ALL of my toys. Used to love using dildos and vibrating toys. Just using fingers for now, getting three in provides a good stretch. Definitely need to go toy shopping again soon.

Some of my most intense orgasms have come from my 6 inch. Once it's all the way in it's hard to not cum, just wish I got more time to do it.