I'm curious - there must be a lot of different stories here and something must have sparked off a desire to try something this radical so let's here about it.
Me and my girlfriend broke every rule in the swinging book with the way we started. At the time we spending quite a few saturdays at her best friends house getting pissed - so there's me and 3-4 girls having a laugh. We got on very well and enjoyed the time.
One Friday night myself and Sarah were at a meal when she suddenly decided that a friend (Let's call her Jane, for the sake of protecting the innocent) was a bit lonely and needed a confidence boost from a man. Well, that's great - but what was I supposed to do, I couldn't go chatting up her best mate. Sarah agreed, but decided a great idea would be to have sex with her.
I laughed and left it to that, but the next morning on the bus Sarah re affirmed that her plan was indeed entirely serious - again, I giggled - though to say I didn't find the idea attractive would be a lie.
So, we get to her house and proceed to have dinner and get midly (very) drunk when we all retire to Janes bedroom. Sarah decides that it'd be an excellent plan to play a truth or dare game - though I don't ever recall getting an option to tell the truth, instead I ended up kissing Jane. Lots. It seems Sarah had either briefed Jane on this or she'd caught wind of it (I should find out, actually!) and had got very into the game.
Then, as if by magic, it was time for Sarah and the other friend here today to go downstairs to wash up or somesuch. Myself and Jane just sat on the bed kissing, until she pushed me away and said "So, are we going to do anything or what?". Never being a man to turn down an offer like that I slid off her trousers and went down on her.
Sarah and the other friend did come in a few times, and obviously everybody knew what we were doing, though Jane covered up for modesty - yet it was just so surreal. It was like nothing was up (Well I was!).
In the end we didn't have full sex (I didn't plan on it anyway) and when everything was over and people sobered up a touch things did get slightly weird. Sarah was completely confused between being turned on like nothing else and being slightly annoyed - and I didn't know whether to treasure it or regret it.
It certainly wasn't the best way to begin swinging, but it was a laugh none the less. Sarah and Jane went on to have quite a few sexual encounters themselves (though never with me), but after that nothing happened for just under 12 months when we decided to go to a club.
So, that's how we got into it - after never speaking about it before, and I'd never thought about it before.
What about you?