Well. I posted a long description for you last night, TM. And today I do not see it posted. I don't think I have the energy to rewrite the whole thing. So I'll give you the highlights.
After a couple of false starts with other guys, we finally met a guy from Craigslist who wold follow through all the way with us. We met him for drinks on Thursday night last week. My woman wore a skirt with no panties, which he eventually discovered there in the bar. She was very wet, so he enjoyed what he found.

We had determined beforehand that the first meeting would not involve sex, so my gal and I talked about whether we wanted to go all the way with this guy, after I licked and fucked her hot, wet pussy. We agreed he was good for us, so I emailed him and we arranged to meet Saturday night.
We met for dinner (I didn't taste a bite) and then moved to his condo a couple miles away - he was good enough to host. We had talked in email about having a glass of wine and him giving her a back rub, with the intention of warming her up and calming her nerves. He waited exactly as long as one swallow of wine before starting to kiss her. He then moved down, enjoying her exposed nipples above the push up bra, and then moved down to her thighs above her skirt. It was obvious to us both that he was going in, so she stripped and gave him full access. He started licking her wet pussy there on the couch, and I got undressed on the nearby other couch, watching intently. She was physically ready for the activities - I'd seen to that before we left to meet him - so he had a very wet reception. But his style of oral sex giving was all wrong for her. She likes slow and easy - he was quick and strong. I give her blame for this - she was really hot and inviting. But neither of us had time to really get into this totally new experience. I could tell from her body language that his sexual style didn't turn her on, and this, combined with my nervousness, reduced my excitement terminally. That is to say, I never could get hard the whole evening.
After he'd licked her pussy and nipples all over, and having stuck four fingers in her tight pussy - what a waste, stretching out such a tight pussy, and not her preference, either - we moved to his king-sized bed. He got on the edge of the bed and she started sucking his cock. I sat on the edge of the bed and got out my phone to take some pictures. His quick, slightly aggressive style didn't quite suit her here again, with him telling her to get on her knees to suck his dick. She ignored him - she gets on her knees for no person - but continued to give him a really good blow job. He got nice and hard and then told her to lay back on the bed. He put on a condom and slipped his cock into her wet, swollen pussy, being sure to give me a good view. After a couple changes of position he got behind her and came in her pussy doggy style.
She really needed to cum, so she laid back on the bed and masturbated to an orgasm with us watching. She then wanted me to fuck her, but as mentioned before, I was having a power failure despite all efforts, so she laid me back on the bed. I really needed to cum, so it didn't take long for her oral powers to draw a huge load out of me. It was somewhat embarrassing to not get hard in front of another guy, who had no such troubles, but I've had the occasional problem with that the last few years (I'm only 48, damn!), so I was mentally prepared. We had all cum, so we lounged around on the bed a few minutes before getting dressed again and returning to our neglected bottle of wine. We sat around and talked about many things, and not so much what we were really there for, and left after finishing all the wine within an hour.
In conclusion, I am very glad to have gone through with this. It was a long roller-coaster 2-month-long experience placing the ad, screening the dozens of responses ( a whole separate topic, way off topic here), meeting a couple of guys who seemed interested but backed out, and finally the whole complete experience. The heights of the anticipation were huge. All we had to do was talk about what we were going to do with another guy and she would get wet. I do love licking her wet pussy! Taking her out to a bar wearing a skirt with no panties and watching a guy explore and discover her wet, swollen pussy lips was so very exciting. The actual event, apart from being backed out on, was the most disappointing part of the whole fantasy. I don't blame our guy for this. We purposely did not script the night of the full encounter; I wanted to let him have rein and enjoy himself, perhaps showing me things about her I did not know. While this made for mediocre sex, I did learn that I know my woman well and can read precisely what turns her on or doesn't, even when I'm not the one touching her. I was somewhat humiliated to not get hard and do what I wanted to do that night, namely fuck her right after he had, but I knew this might happen and wasn't too surprised by this. If he'd gone slowly and given ME time to get accustomed to this, if his oral technique had been more to her liking and thus worked her up even more, and if I wasn't so prone to being nervous, things might have gone differently in the wood department. Way too many strikes against me! The situation was the issue with me; the next morning when we woke up caressing at home in bed, I quickly got hard and gently fucked her and came (she was still a bit sore). So all came out well in the end.
Would we do it again? Yes, I'm game, but probably not with this same guy. Our sexual styles are too far apart. But the whole experience was so exciting, and I have some exciting pictures that I still look at at least a couple times a day. My gal asked for a break for a while before finding another guy to do this with, and I'm not sure how long that break may be. This really increased the communication between me and my gal. She has always been the adventuresome one, and she has corrupted my repressed ass.

I felt that our relationship was strong, and that we were both secure in it. But I never could be completely sure until we went through with it (this was not done as a test, by the way). Somebody else in this forum said that seeing a guy stick his cock in your woman's pussy was something that you'd better feel sure you can take, because "you can't unsee that." The phrase stuck in my mind the whole way through this process - thank you, and I'm not being sarcastic. But I felt exactly zero jealousy in watching him fuck her. I had slight qualms about seeing them kiss, but I know her well enough to know that she is quite able to separate sex from feelings (though not with me!)... that felt more intimate to me than PIV sex somehow. But it was all part of the encounter, and I was ready to see that. Our sex life is great now, and it may be that our curiosity is satiated now. I would have liked to have found someone we felt inclined to meet once in a while for more sex, but I just don't see this happening with this guy, and my gal agrees. Since things are going so well, why would we want to bring possible drama into things? Well, it's exciting, so who knows...
If anyone wants to know more about this, or has other questions, I would welcome them, either here or in private messages. Talking more about this helps me process it more completely. I sure hope this posts this time!
Device(s) owned: CB6000S, numerous stainless steel Chinese knock-offs.
Last ejaculation: Recently