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dzepher Novice Jackinchatter

49 posts since 2010-05-21
42 year old heterosexual
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Just read a few different discussions like the prostate massaging one and was wondering what the most bizarre thing you guys have ever shoved up your bums was.

What takes the cake for me was definately the drunken night I decided to plant a spade shovel into the ground, pulled a connie over the end, spat on it, sat on it and drove her home.
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luvheels Skilled Jackinchatter

611 posts since 2007-03-16
59 year old heterosexual transgender female from Canada
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A backscrubbing brush. It wasn't thick but it was long. I got over 10 inches in my ass.
No heel is too high
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kungfu40 Amateur Jackinchatter

411 posts since 2007-10-27
bisexual from Canada
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A Maglite flashlight (D cell size) wrapped in Saran Wrap and a condom, with lots of KY. I have gotten it in up to 10 inches on occasion, but it takes a lot of patience!
Whatever gets your rocks off!
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It's pedestrian, but a cucumber. The highlight of the event was being a 16 year old boy arriving at the counter with three sizes of insertable melon, condoms and lube. The cashier and I died laughing shortly after I turned bright red.
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Weird_Al Novice Jackinchatter

88 posts since 2009-02-16
heterosexual from Chicago, Illinois
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Sears Craftsman #3 phillips screwdriver handle
Thinking about getting a #4
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thickboner4u Professional Jackinchatter

1030 posts since 2008-10-07
70 year old curious from KY
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Nothing particularly odd...just routine household items....carrot,cucumber,candle,hair brush handle...the usual suspects.
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When I was first experimenting as a teen, it was a piece of string cheese. Lol. I found I needed something bigger and more solid.
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mrtoelover Novice Jackinchatter

62 posts since 2009-06-25
52 year old heterosexual
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a tampon
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Barefoot Amateur Jackinchatter

152 posts since 2005-08-27
41 year old curious from Wales, UK
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During my teen years I used to try out every weird fantasy that would spring to mind. One day I decided to put of load of gelatine (mixed with water and left to set) up there to see what it felt like. Strange maybe, but it made a great lube!
"Going barefoot feels like secretly going naked in public."
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mwm4usil Novice Jackinchatter

42 posts since 2009-01-30
60 year old bisexual male from Southern, IL (C'dale-Marion)
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I'm with kunfu40.
I've used a MagLite 5 cell (D cell) flash light in plastic wrap & a Magnum condom.pussy It was awesome!cock With some practice I was able to take it right up to the the flare for the light.amazedstrokeeyeshot
By far the biggest (longest) thing I ever inserted.
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Man....you boys are making me hot!
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Early on when I discovered my favorite pastime in the bathtub. I was playing with an empty shampoo bottle when one thing led to another. I filled the bottle with warm water and squirted it in my butt. After I had squirted 2-3 bottles in me I would jack off. When I came, I blew out of both ends.

Hmmm recalling this memory has got me all hard. I think it's bath time!
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papabare Amateur Jackinchatter

425 posts since 2006-12-30
85 year old bisexual from Chicago, IL, northeast: East Rogers Park
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dzepher said:
Just read a few different discussions like the prostate massaging one and was wondering what the most bizarre thing you guys have ever shoved up your bums was.

What takes the cake for me was definately the drunken night I decided to plant a spade shovel into the ground, pulled a connie over the end, spat on it, sat on it and drove her home.

My best buddy had hurt me accidentally when he entered me too hard, I was about to try again, with someone else. In preparation, I used a cucumber twice the thickness of his cock, figuring if I could get that in, I could relax and enjoy things with this new guy. IT WORKED!!
PM me for phonetext info: [email protected].
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curiousbored1298 Amateur Jackinchatter

202 posts since 2010-03-26
42 year old heterosexual male from San Francisco Bay Area
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six inches of a small flash light. using hand soap as lube ( I dont recommend it), it slid in and out smoothly. Once it slid in for the first time, my cock got super hard super fast. Best organism till I had sex for the first time.
Masturbation is fun, let's chat about it! Link to my bate pics and vid is in my profile.
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