Worst I ever had was with my best friend growing up. She and I had been friends since junior school, by the time we were late teens we’d had the occasional drunken kiss and famously she jerked me off one New Year’s Eve (I say famously because she did it in a room full of people we thought were all asleep but one friend was awake and watching…)
Anyway, by the time we were mid twenties and working we still maintained our friendship and one drunken summer’s afternoon we ended up at my place , making out and generally being naughty. As with previous occasions I was playing with her tits and she was jerking me off. I stopped her and told her I wanted something else.
I stripper her down, found a condom and slipped inside her. Unfortunately, the build up of the previous 20 mins being jerked off meant I came as soon as I was inside her. I tried to disguise it, but almost immediately went soft. All I could do was apologise and offer to help her out another way, which she declined and we ended up just sleeping.
We never did anything else together like that, so if she remembers it at all she will have the abiding memory that I’m rubbish in bed (I’m fairly certain I’m not)
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