Disappointment, Early Arrivals, and Farm Equipment

I feel like sometimes I disappoint.  I suppose it's related to the self esteem issue that I battle, but there's a touch of perfectionism, a little bit of not measuring up, and probably just a lot of nothing when I feel this way.  I did get to stop and visit a guy on the road Friday, a visitor in a hotel room...an ideal setup.  And me, having not gotten any at home, had a big load (that's a positive) that blasted out way too early (that's the negative).  He was nice, enjoyed playing a bit with my load, and it didn't seem to bother him.  But it bothered me.

When I get to stop and play, I want to make the most of it.  And a 5 minute roll around wasn't exactly what I was hoping for.  So I disappointed myself that I wasn't able to take full advantage of the time I had.  Is this a common thing, being hard on yourself for performance?  It's probably a little bit that way, but also people aren't likely to share this info when talking about their conquests.  Why wouldn't you brag about your prowess, how you fucked him til he couldn't walk, when you have the chance?

I suppose that's why I lean a little more to the bottom side lately, it certainly takes the pressure off from that perspective.  And who doesn't want a big dick bottom?

My first time on the bottom was, as I'm sure it is for most people, a difficult, somewhat painful experience.  I had chatted up a guy on gay.com (wow, how long ago was this??) chat room, and he was staying in a hotel in downtown Des Moines.  I was going to have some free time while in town, and we made arrangements for me to stop over.  He was a nice looking guy, farm type, skinny, reddish brown hair, here for a farm equipment meeting (cliche, huh?)  We made out a bit, and he made it clear he wanted to fuck me.  I'd only had one dick in me before that, and while it was not an accident, it didn't last for me.  It was before I understood the immense value of warming up and lube.

This guy was good, patient, and took plenty of breaks as we worked toward him getting into my ass.  The time was well spent, as once I got used to the invader, I enjoyed the feeling of fullness.  I was glad he was on the thinner side of cocks, made things easier.  So being face down and getting drilled, albeit relatively gently and carefully, was something that I found out I enjoyed, and would like to try again.  Regardless of what those sexy stories online tell us about a first time, going in dry, taking a huge one, I would imagine that would be a bit much for all but the most sadistic bottoms.