not worst sex as such
I shall not give the ladies identity away (cos we're still together), but many moons ago I started dating a rather marvelous young lady only to discover that she was a virgin. A real live in the flesh virgin.
Normally I would have been totally put off by this (I like my ladies to know what they are doing) however, there was something different about this girl (took me a while to realise it but I was in love).
Anyway, we'd been going out for about three months and I've been patient and not tried to get her to do anything she didn't want to. Actually it's better than it sounds as the only thing she hadn't done before was the deed itself.
So, I whisks her away down sunny south to my parents caravan (I'm quality me) for a few days 'away from it all' and 'together time'.
The night comes and I'm all prepared (12 pack in my back pocket) I've cooked a nice meal, got a few bottles of nice wine, old spice splashed in all the right places etc.
She tells me pretty formally that it's time and we retire to the bedroom with the wine.
Now, the beds in caravans are normally not very big.
I'm quite big. At least a a foot or so longer than the bed.
So, we start getting into it and things are hotting up. She's getting excited and tells me to go for it.
A quick fumble with the condom wrapper and I'm all set up. Except, I can't seem to get a good angle as I don't really fit on the bed properly. Rather than change postitions - flip her over, do her up against the wall or make her do the wheelbarrow (thought I'd save them for her second time), I put one hand one the bedside table to give myself some leverage.
Bad idea. My mum is a total cleaning freak and polishs everything like crazy. I'd put alot of weight on my hand and there was no friction on the table at all. My hand skimmed across the surface, swiping the (mostly full) bottle of wine across the room so that it shattered against the wall, drenching the room in red wine. At about this moment I also hit the floor and rolled over onto my back.
My gf shouted "oh my god!" and sprang out of the bed to get a rag. I thought it was the funniest thing I'd seen in ages and cracked up.
As she was cleaning she turned to me, pointed at my cock and said "and you can get rid of that". Thankfully she meant the condom. Sadly this meant I was not getting any sexy loving tonight.

Thankfully all went as planned the next day, and umpteen years later we're still going strong and she's my totally hot hunny baby.
(EvilMeister, Sat 16 Jun 2007, 0:48, Reply)