I have had all sorts of inanimate and live things in my butt (bare cocks) for 30 years. Love the feeling but no hands free orgasms.

 

That's really easy, when I lost my anal virginity to two gay men when I was 18,ever since I have loved having one when I'm getting fucked up the ass hard

 

I started playing with a dildo just to please my anal pleasure, then I tried my wifes g-spot vibrator which is curved & realized I had found my p-spot, felt awesome, then all the sudden I started cumming a thick cum, whole body shaking for felt like 5-10 minutes, it was awesome, & it tasted much better than my usual cum

 

Hooked up regularly with a friends dad when I was a teenager. Started off sucking his BBC only because I was worried it was too big, a bit scared
Took a bit of time, but finally gave in and surprised him in bed ass out and ready to go...first time was the charm and it was crazy!

 

My first time was a solo event. I had been curious about anal play for awhile and had ventured into it a few times but never got the outcome I was looking for. I enjoyed the feeling of cumming with something stretching my ass hole but never had the full on explosive experience I heard people talking about. I had tried different items up there from around the house and even built my own silicon dildo but what did it for me was the handle of a toilet plunger. Not the wooden kind but the clear acrylic kind with the stacked bubble handle. I was working myself over with it rubbing the upper inside of my hole feeling my sphincter open and close around the handle knobs when I pushed in farther. I could feel it pressing on my bladder and although it was not painful or uncomfortable it was an odd feeling I enjoyed. I wiggled the shaft around pressing on all the spots that felt good until I hit the spot on the front that made my leg twitch involuntary. I focused on the spot watching my precum ooze from my tip with each push.I wasn't even touching my dick just poking that spot when my entire body shook and I unloaded the biggest puddle of Jim in my life all over my stomach. I swear it was a quarter cup. My entire body tingled and continued to convulsive slightly. From then on I have been hooked and used my piston sex machine all the time to butt fuck myself. Like any drug it is never the as good as the first time but I keep trying to reach that bliss again. Maybe one day I will try a real one and it will be.

 

A gay guy recruited+me as a tenager abx over a few months he woulx fuck my as with his 5 inch dick.id sometimes pass out .be careful. its powerful

 

This is so hot

 

I have never tried. I'm not sure if I even know what to try to give myself one.

 

I've never had one of those.
They say you can't teach an old dog new tricks,
I say bullshit to that, this old dog is willing to learn.

 

HFOs are nice. Mine were by surprise. I don't plan on one, a little fondling makes it a good every time.

 

Had a ten inch cock in me up to his balls, while his wife sucked me dry. Did not know I could ever cum that hard. Use a vibrator now days.

 

I haven't ever had one but I've tried

 

Had a footboard that had turned wood end pieces that fit nicely ad could give me a prostate cum. Simply amazing. Wife never knew

 

Cleanest floor around the bed!

 

My first one was when I was in my early 30s. Took a long time and a lot of patience with a dildo to make it happen. My body didn't know how to connect the act of masturbating to having something in my ass. Both of which I'd done a zillion times before. But the first time I paired the two acts I didn't think it would ever get there. When it did I thought I was going to black out! I've never shot cum that far before! It literally flew across the room. And as my ass clamped down on the dildo it hurt and felt amazing at the same time. If a real man had been back there with his cock inside me I think I might have pinched it off!

Been hooked every since.