My 1st time was with a fuckbud with a small cock and it was neither painful or memorably pleasurable. He did use plenty of lube and was very gentle.
The reason I let my small fuckbud fuck me was I had met a guy with probably the biggest dick I had seen up to that point play with my hole for hours on several occasions, but was afraid to let him pop my cherry. After few days of thinking about it I met up with the small guy to see if I could take it. Less than 24 hours later I got back with my huge dicked new friend he hurt some going in but he actually fucked the cum out of me without any stimulation to my cock, just as he filled the rubber in my ass, and I could feel him filling his rubber and was scared that it had broken, but it was intact when he pulled out. I was hooked.
Both guys fucked me regularly for my remaining semester and a half of college.
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