Jack bottoms.....

When I first met Amigo, and we were getting to know each other, over our first coffee date, we were quite honest and straightforward with each other.  Amigo let me know he was a "bottom".  He had little interest in dating another bottom. 

I, of course was/am a total top.  I tried to bottom a couple times, with the same partner, and once was a total failure, and once, I believe penetration happened, but it was short-lived, painful, and embarrassingly, a little bloody.

I'm afraid, I just wasn't built to bottom.

Not that I don't want to.  I see all those guys in porn, moaning with pleasure.  I read the stories about "unbelievable waves of pleasure."

I've expressed this desire to Amigo.  He's not particularly huge, smaller than me in fact, and we've alway joked around that one day, we were going to try.  I was going to try to bottom, and he would try to top me.  He even toys with my hairy ass sometimes, but I alway swat his hand away.  It feels a little foreign to have some  strange fingers roaming around down there.

He was alway asking, but it never really seemed like the right time.  Week after week he would say it was his turn, and then I would wave him off.

But, lately, I've been thinking about it.  Why not just try it?

Last week if he once again asked if he could fuck me and  I said yes.  I wanted to try. 

He looked like a deer in the headlights.  "Really?"

"Sure, let's do it.  Just be gentle."

Pause.   "No."

Turns out, he was bluffing all along!  He doesn't even want to try.  And, when I pressed him for a reason, he said he didn't want to turn me into a bottom!  He's afraid I will love it, an that will change our dynamic in the bedroom.  Haha!

I guess it could happen.  I'm a bit fan of  Reddit's Gay Stories Gone Wild.  Many times I've read how anal virgins were exposed to this previously unknown pleasure, and now they are itching for dick.

Perhaps Amigo is right.  Perhaps I don't need to travel down that path.  After all, we have a good thing going and we both pleasure each other.  I guess there is nothing wrong with that.

So, no.....Explorer Jack did not bottom.  Is not a bottom, will probably never bottom.

Butt, that's okay.

Just some photo I found online, to entice you to read my entry.  :)