Too close to a near-miss reality to be funny... Short form, I was 23, she was a PYT being served in the local bar, and things worked out so that at the end of the night, we were both out behind the lilac bushes in the park, nekkid, getting seriously hot-n-heavy, with me less than an inch from slipping inside her when she says "Um... don't stop, but go real slow - it's my first time and I heard it hurts" My response, hovering above her, "how can it be your first time??? You're gorgeous, and as far as I can tell, it seems like you've done this before?" She comes back "No, before was all practice - Tonight was the first time I was able to get into the bar." "Why's that?" I asked, rubbing the tip up and down between the lips of her vulva, almost in her, but not actually trying for penetration - just trying to keep from going soft and having to start over. "They boot you out or something?" She comes right back "Well, I wasn't supposed to be there tonight, but I slipped in when the door-guy was tossing out two of the other girls from my class." "Your class?" I said, starting to wonder if there was some serious shit about to hit the fan. "Uh-huh - We had a bet against (name deleted) that we could get in when she couldn't."
I should mention here that I knew (name deleted) - quite well, since she often worked right alongside me - She was my boss' daughter, and would be turning 14 in about 3 weeks - I was already on the schedule to drive the horse-drawn hayride for her birthday party. "What are you doing making that kind of bet with a kid her age? As much older than her as you are, that's almost like... " I trailed off as the calculator buttons in my head started to rattle - 2+2=... and my cock started to go limp and slipped out from between the lips of her vulva as I saw the total coming up to 4. "How old did you think I was?" she asked. "At least 21, since you were buying beer in the bar... Oh, shit... you can't be saying..." She giggled and said "Great makeup job, huh? (name deleted) is a year older than me - She's in the next grade up... What? What's wrong?"
My dick not only went limp - I swear that for a few days afterwards, I practically had to use tweezers to reach up inside and pull it out when I needed to take a leak! It wouldn't surprise me a bit if someone today, pretty near 30 years later, were to go to that location and report that they could still see the scorched dirt from my cartoon-character style burnout as I snatched my clothes and got the fuck outta dodge...