So you need to try everything @ least once in life to know if you would enjoy it or not. Don't knock till you try it.

How would 1 go about try peggin bearing in that the only previous experience was just a petite females finger and that was a while back

1 - Well, you could perhaps start with a small, thin butt-plug to see if you can accommodate it and that it "agrees" with you. Or anal beads. Back in the day I started like that and went a bit bigger and went from there to option 3 below (not for everyone).

2 - There are ladies on the site that have mentioned pegging services, so perhaps one of them has different sized "attachments" that can ease you into it (or ease it into you lol). Or you can find one that will use some toys on you (perhaps bring your own). I have not tried this way yet.

I know I like it, especially since "keeping wood" is very easy for me during. Good luck in your experiment, whichever option you choose.

3 - Not for everyone. I skipped option 2 and went for a she-male that basically did option 2 on me with toys before...well you know. She unfortunately left the business a couple of years ago already.

Which ladies is offering this service?

On 2018-03-24 12:19:20 Cumster said:
Which ladies is offering this service?

I Do.. prostrate play,buttplug,anal beads,strap on..take a pick;)

Me too
www.massagebysage.wordpress.com.
I must add that I'm exceptionally gentle too.

Is it painful for a first timer?

It shouldn't hurt at all.

I know Mercedes is very good on this, I too try but not as good as her though.

On 2018-03-24 12:55:54 Cumster said:
Is it painful for a first timer?

There should be enough lube involved, and one should start smaller if one is new to this. Relax as it will help ease things in causing feelings anywhere between "hmmm interesting sensation" and full on "omg that is the spot spurt spurt" :)

Go for it!. As Chameleon says, plenty of lube, and maybe start with something small. That said, nothing wrong with a ladies finger if she knows what she is doing. Luckily my wife is an absolute wiz at this - many happy orgasms while she is sucking me off and playing in my butthole - with fingers or toys. And one one the most amazing orgasms I have had was a threesome where my wife was riding me, with the SP tea bagging my balls and playing with my prostrate with her fingers!

Not sure where you are, but Chasidy in Pretoria and Jiah in JHB are highly recommended.