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The biggest cock I ever personally handled was on a guy I met at a bar.
Not handsome, but cute, scruffy, remnants of bad skin.
We weren't friends, just offered one another a friendly "Hello," with each passing.
One night, I went to dinner with a friend, and, he was the server assigned to our table.
He climbed into the backseat and I tried to sit on it- I still remember a remix of that awful Sting song "desert rose" was playing- and I yelped when it went in. 12 years later, I can now handle a pretty big dick. He would wear shorts with no underwear and sit with his legs spread really wide and his cock would kinda hang out of his pants.
Being the little queen that I was, I couldn't take my eyes off of it, he noticed and decided that he was going to use me as a way to get some extra cash from my parents.
Um, yeah it was GHB and I have probably had some 3 or 4 times in my life (and if you'll read my post it was 12 years ago). I wouldn't think any of you were retarded for not knowing. I thought my recollection of the Sting song was pretty good at setting the scene tho!
The older asked me if the younger could fuck me- I had only been screwed a couple times but wanted to try. Laughed it off and we jerked each other but I was pretty embarrassed. He would sit by our pool and I would bring him lemondade.
He was very attracted to me and very aggressive in picking me up.
He was a grad student and we used to meet in his tiny room -- we kissed and made out and he warned me that he was big. 8-9 inches long and the widest one I have ever seen, it was massive. What was incongruous was that the guy was pretty thin.
I wondered later if the hugeness of his penis, the number of people that had either refused to have sex with him because of it, or who ONLY wanted to have sex with him because of it, caused him to be detached and indifferent to it, and actually increased his masochism somehow.
Well, OP asked for your first experience, so I shared.