The funniest one was a time that I started to penetrate a guy that was lying on his back in a sling, so he couldn't see me very well. I was astonished when he came before I was even all the way in on my initial thrust. "I guess it was bigger than I thought" was all he said. We both cracked up laughing.
Sometimes at sex parties, I will find a guy in a position where he can be fucked, but not necessarily expecting what's coming. I've had some guys violently buck or push me off after I penetrated. Others will just shout some surprised exclamation, like "OH Fuuuuck!" Still others will just bite the pillow and stay quiet.
It's always interested me that it's often the larger guys that have trouble taking me. I remember once I had this 6' 4" walking brick shithouse get in the sling in a rather dark room, so he didn't know what to expect. I was exceptionally excited (he was HOT!
, but when I put it in, he made this loud bellow like a sick cow, they said "It's not going to work." Another time, I was playing with this young (22) guy who towered over me at 6' 6". He had been loaned to me for the evening by his "Daddy," while Daddy had another playmate. When it came time to fuck, he called Daddy on the cel phone and said "No, I can't. Eric's too big." Despite his refusuals, I knew he wanted it, and eventually did get into him. The reaction was quite amusing:
"Oh no! It BURNS! It Burns! Take it OUT!"
I did, but soon had it back in. I never really was able to fuck him, though, except very slowly and gently for only about 5 minutes.
On the other hand, I've played with these little Asian guys, barely as tall as my shoulder, that just pop me in like it's a toothpick, and want to be rammed as hard and long as possible.
Most of my size is in the form of large girth, with a quite modest length of only about 8 inches, and my cock is not tapered to any great extent. So, in my case, it is an immediate surprise as I get in my thickness. I've always wondered what it would be like to have the same amount of meat arranged differently, with average girth but great length. I wonder what the reactions would be as such a penis enters without much fanfare, but then keeps going deeper and deeper...