MacNfries said:
I'd love to know all about you guys ... how you met, how you got into Cuckolding, etc. Thanks for the contributions thus far! Mac 
How I met my wife? Through a mutual friend a LONG time ago. How we met her lover? Online

Took a year of him and I talking to get to know each other and then eventually meet. When my wife and I picked him up at the train station she was super nervous and said nothing would be likely to happen but if she thought it was ok, she'd give me a sign. About 20 mins later on the subway she turned to me and grabbed my crotch and gave it a rub before winking at me. A good sign ;-) 2 hours later she was on her knees sucking his cock. He's been fucking her regular ever since and that was over 2 years ago.
How we first got into cuckolding? Man, that's a good question. I've always been into watching my women with other men, there's just something so incredible about it. So hot. So naughty. What turns me on the most is not so much sharing her, its showing her off and looking at her. I like watching her with others (girl, guy, couple) but it isn't really about the sex. Its seeing her let go of insecurities and inhibitions and just having fun and knowing other people admire her as a good looking, sexy woman and not just as the nice sweet person she is. I also like being watched while we have sex. My turn on is basically having other people look at her and admire her like I do. She modeled for me for a nude photo project in the past and I love showing the pictures to others. I love when she wears tight or see-thru clothes when we go out. I like catching other people looking at her chest or her ass. It doesn't bother me at all when people approach her at bars or flirt as long as they're not pushy or disrespectful. I don't need to be involved and would even like to watch from across the room while I jerk off or secretly watch from a closet or keyhole.
We started talking to couples after a few years (literally) of me trying to convince her. We hooked up with a few couples and it just didn't click for a couple of reasons. Either the girl didn't want to be shared, just play with my wife or the couple were doing it for the wrong reasons, etc. Plus I wasn't THAT interested in fucking other women, to be honest. Sure, I wouldn't turn down the chance to fuck another hot woman but to be honest, the women we found were never as hot as my wife so it's like why drive a ford when I can drive a ferrari. So we started to focus on my real passion which was her with other men (with or without me involved.) And that's been incredible so far, we both love it. The only struggle has been finding guys we both like and are just as comfortable with as friends as we are as lovers.
The search continues....