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Craziest and biggest thing inserted in your ass.

I haven't done too many insertions. But I did find an aluminum cigar tube one time. Was going to throw it away, but then I thought, "huh, looks like I could do something with that."

Next time I started full on jerk-off session, I lubed the thing up and slipped it in my ass. It was completely smooth and not super thick, and lubed up, I barely felt it go in once it was past my pucker.

So I sat down and started watching porn and jerking off. Never really could feel the thing inside me. After I blew my load, I tried to fish the thing out of my ass and couldn't. 😱

Ended up sleeping with the damn thing up my ass. Had to poop it out the next morning. Will be more thoughtful about the next thing I shove up my butt. 😆
 
I bought a 20 inch thin dildo and started with that. Then I got a slink dildo and thats about 30 inches, but I never could get the whole thing in - probably got 24 inches. As for width, an inflatable buttplug that was about the size of a grapefruit (inflated when inserted). Had these large anal beads, the size of tennis balls - fit three in. Had a large buttplug, about the size of a soda can… but I stopped with all but the inflatable - the wide would make me bleed a little, and the long was probably not a great thing to do in the long run. Me challenging my asshole days are over, I think.
 
NCWSLvr said:
I bought a 20 inch thin dildo and started with that. Then I got a slink dildo and thats about 30 inches, but I never could get the whole thing in - probably got 24 inches. As for width, an inflatable buttplug that was about the size of a grapefruit (inflated when inserted). Had these large anal beads, the size of tennis balls - fit three in. Had a large buttplug, about the size of a soda can… but I stopped with all but the inflatable - the wide would make me bleed a little, and the long was probably not a great thing to do in the long run. Me challenging my asshole days are over, I think.
Click to expand...

Where does it go. The longest I’ve been able to take is 9-9.5 inches.
 
Mrs_and_mr said:
Where does it go. The longest I’ve been able to take is 9-9.5 inches.
Click to expand...
Large intestine. It takes a bit to get past the second sphincter. The first bend is wild. Never could get it past the second. It takes a lot of persistence and work.
 
NCWSLvr said:
Large intestine. It takes a bit to get past the second sphincter. The first bend is wild. Never could get it past the second. It takes a lot of persistence and work.
Click to expand...
We use soft silicone dildos so they can bend but they hit a dead end at 9”
 
I guess the craziest was a hair product bottle. I don’t know what I was thinking at the time to do some like that . I was in my 30’s which is a very horny time for women so trying over the top masturbation methods got me really turned on. I was able to get it all in with plenty lube. I also fucked my ass with 7 inch dildos before taking an actual cock .
 
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The knurled handle of a socket wrench set. I mentioned to Her that I would like to try it. She thought it would be fun if I stood in the corner and held it in for her by clenching my anal muscles. It dropped out (from gravity), She gave me a stroke of the folded belt. Every time it dropped out after that, she stroked again plus whatever the number of the try was. By the time I learned how to hold it in, I had a few welts. This was many years ago. We're in our seventies now. She's still very adventurous, though we play nowhere near as frequently.
 
my Mistress/Wife inserted a borrowed giant black life-like dildo in my boy pussy in preparation of Her Bull using His massive cock to fuck me in of possibly having Her black Bull use His massive cock to fuck me. He had never shown any inclination to use me in that manner, and i was scared for the real thing to penetrate me. i worried for nothing. my Wife only "felt" like humiliating me. When He arrived i did my usual fluffing of His monster cock, and then He, as always, dismissed me so He could fuck my Wife in O/our bed.
 
I've gotten bored and used my wife's 10" dildo, it's really thick too, actually done it several times. Almost got it all the way in. It actually helped me approach anal sex with my wife better as first hand experience is a great way to know how to make it better for the receiver. She'd think the worst of me if she knew I did that.
 
LinusLattimore said:
The knurled handle of a socket wrench set. I mentioned to Her that I would like to try it. She thought it would be fun if I stood in the corner and held it in for her by clenching my anal muscles. It dropped out (from gravity), She gave me a stroke of the folded belt. Every time it dropped out after that, she stroked again plus whatever the number of the try was. By the time I learned how to hold it in, I had a few welts. This was many years ago. We're in our seventies now. She's still very adventurous, though we play nowhere near as frequently.
Click to expand...
Not ever been into anything like this, but I am absolutely thrilled to read that your partner/wife is adventurous into your seventies. :):nana:😃😍🤩
 
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