In 1999 I was a normal Australian teenager of 14 going about my business when my father got a job in Hong Kong. My family moved there with him. From 1999-2003 I had almost zero luck with girls there UNTIL I was 17 and started dating this utterly gorgeously cute girl from the year below me just after I graduated from high school. Her name was... Debbie.
Anyway, it was a first love kind of thing for both of us. It was corny as fucking fuck and looking back on it I cringe a little sometimes at the shit we got up to. Central to this story is how we dealt with our hormones given both of us were living with our parents in rather small, HK-style apartments.
You see, we used to go for walks around the place and find the quietest, darkest, most private secluded enclave we could. On Hong Kong Island this is a pretty tall order but we managed it. After a date of getting dinner or seeing a movie or whatever we would go to whatever semi-private public place we could find and make out, dry hump a little, feel each other up... all that sort of stuff.
Of course, this was interspersed with us sneaking into eachother's rooms for more serious fucking sessions but this wasn't always an option. Neither of us really considered the possibility of a love hotel. Like I said, we were kinda naive in an odd way.
ANYWAY I'm getting side-tracked. In these public park adventures she would often blow me. It was fucking great (she swallowed like the best of champions) but she could sometimes be a little too rough with her hands. This was an issue for me as I had a somewhat more prominent frenulum than the average guy.
'What's a frenulum?' you ask. Well, that's a small piece of connective tissue that joins the foreskin of the penis to the glans. It's also known as a banjo string in modern parlance. It's much like that flap of tissue than joins your tongue to your lower palate. If your frenulum is too prominent it can make vigorous sexual activity uncomfortable, given its proximity to the festival of nerve endings down there. Mine was a fairly mild case, but I was definitely aware of it.
So, setting the scene. I have to leave Debbie to go back to Australia for university. We are both SUPER FUCKING DEPRESSED at this. First love! We were both fucking crying over it but nothing can be done. We just make the most of the time we have together before I leave.
Cut to the night before I fly out. It's Valentine's Day. We meet up, comforting each other, have dinner somewhere and walk around holding hands. I buy her a rose. Habits are hard to break so we find a little park off a fairly major road that pretty much no one visits. We sit at the conveniently hidden bench we found there behind some bushes and get down to business. For the last time in who knows how long. On Valentine's Day (I can't emphasise that enough).
We're making out, my hands and fingers are all up on her boobs and in her pussy under her jeans. As per the usual eventually she unzips me, gets down between my legs and begins to suck me off.
Part of me knows I will be utterly sexless for the next few months at least so I lean back and enjoy. We are both getting into it, my hips are thrusting and I can feel I'm about to cum. As was (and still is!) my custom, I inform her of this in breathless tones so she speeds up that wrist action a bit.
Simultaneous to me JUST beginning to blow my load into her mouth, I feel and somehow HEAR my frenulum fucking SNAP. Well, more accurately somewhere between a snap and a pop. I freeze after crying out OHGOD in pain and shock and doubling over.
Debbie shoots up from her knees in about a millisecond, having heard and felt the same thing except in her mouth. There is blood, spit AND cum covering the crotch of my unzipped jeans and smears of it on her lips and chin.
She is crying and screaming and literally fucking running around like a hamster in a cage thinking she has broken me forever. Tears of shock and horror are streaming down her face, meeting the blood and cum on her chin and forming a mixture of utter sorrow and pain. I am literally - LITERALLY - zipping up and chasing her telling her not to worry, I'll be fine I'll be fine. Hugging her (hips out) to get her to quit pacing like a mental patient on meth.
That's right, MY COCK IS BLEEDING and I'M comforting HER.
Anyway, once I reassure her that I'm not going to bleed out the date ends. I recall getting an ice cream on the way back to dropping her back at get house. It was a weird night.
When I get home my cock is a horrific mess. There is a mixture of semi-congealed blood and semen slowly cementing the underside of my cock to my boxer shorts.
After peeling it off my underwear, washing and disinfecting it hurt like HELL but there was no way I was going to the doctor with this unless it got infected and I really had to.
The following day she comes to my family's apartment and my parents actually have the grace to give us some alone time. Unfortunately my cock is completely put of action (that's right, I've had a scab on my penis. You?) sooooo basically instead of fantastic goodbye sex all that happens is a tearful goodbye.
addendum: turns out she did me a favour. She COMPLETELY OBLITERATED my frenulum with one downstroke which means my foreskin moves as freely as if I'd had corrective surgery!
tl;dr - my cock broke inside my ex's mouth on what was supposed to be a tender goodbye date