What is the first thing you put up your bum?

[trevorness]

In my youth, experimenting, i used pens, brush handles, plunger handles, vegetables and whatever was handy. Later a nice sized plug.

 

[liqueur]

60's man here thinking of trying some anal play alone and with my wife, but other than fingers I'm not sure what to try. Jumping straight to a life-size dildo seems to much to start with, so was hoping to get some ideas of alternatives.

What did you start with and how do you progress to something bigger?

I started when I was unmentionable young. Thing is, at that age your body is a lot more flexible and resilient, and lubricious too— or at least mine was— so it was easy. I was first sodomized by a plunger handle in the bathroom, but it wasn't long before I'd graduated to a pitchfork handle the hay loft. I never looked back.

 

[liqueur]

Carrots are a bit hard at the edges.

Try cutting the very end off smooth, just where the greens would start, and then slipping it in big end first. It's great!

 

[liqueur]

V proud to say that after a tentative beginning, this is what I managed to work my way up to: https://gofile.io/d/4I9Qkd

What a great cock! I want some of that!

 

[liqueur]

..

You do know you can delete your post if you don't like it, right? No need for the dots.

 

[daytr1pper]

I was pretty young. Taking a bath. Had some toys I was playing with. One was a plastic cart. I stuck the 'hitch' end up my sphincter.

The next item I can recall was a toilet plunger handle. A nice size for starters.

With all of that said - get a toy. Don't stick anything up your butt that wasn't designed to go there!
(I've got a list of things I could share that have been there that shouldn't have been... And one day I should take my own advice...)

 

[sandybrooke]

My finger. Still do this

 

[phunkyphresh]

my own finger ... its been a while since i did that.

 

[aquam34]

A nine inch cock. I met him at a local football ground while I was watching a match. He was playing on the team and somehow we made eye contact as he came to fetch the ball that had rolled off the pitch near me. He came up to me after the game. It was almost as if he read my mind. He asked me to join him for a coffee. We had a coffee and ended up at his pad close by. I intended to suck him to an orgasm which was my fantasy. But even after twenty minutes of sucking his rock hard cock, he just seemed to be unaffected. My jaw hurt and I wanted to rest. It was then that he pulled me onto the bed and turned me over. Then with a steady, continuous thrust, he took my virginity. He fucked me for an eternity and shot his load on my back.

 

[OralAllOver]

My head

 

[YummyCumDump18]

First thing I ever tried was a blunt carrot. Not a particularly large one and with less girth than the average dick, but I knew if I couldn't handle that I'd no business offering my ass to a guy.

That’s what I first used too!