When I lost my virginity. I was 23, she was 18 but had been with lots of guys. As soon as she saw it her eyes bugged out, she changed positions and started making comments while staring. Multiple comments including the word "big." I thought at first she was teasing me or trying to flatter me, so I teased her back a little: "By big, do you mean not small?" She said "Big like I'm about to get fucked by King Kong." Then she brought out a standard condom and I could barely fit it on, it crushed a "staircase effect" into the central ridge and was heavily painful. I had tried a condom on once when I was, uhhh, way younger wink wink, and size had not been an issue. Watching lots of porn had led me to think size had never become an issue. Between the significant discomfort from the condom, my inexperience and her trying to take a first timer who was beyond her size class, we both were not in top form. After squeezing somewhat inside her for a while neither of us were comfortable so I pulled it out. Happily she was very much a fan of naked guys and cock, we pleasured each other all night long without sleeping, if you added up all of the many blowjobs of a full sleepless night it was likely well over an hour of her licking and slurping and even allowing me to drive a pretty hard facefuck, she really trusted me even though I was both big and inexperienced. She loved it and it changed my life.