Hi Folks:
My wife and I are considering trying swinging. We are considering starting with a MFM threesome (there's essentially a current opportunity to do that), then an FMF threesome (when the opportunity presents itself). I guess our main question is: are there any red flags in starting this way? I don't know if we'd continue with anything else after that...a lot probably depends on how we feel about these two experiences. More details below if you have the stamina to read my long posts!
I"ll try to make this as short as I can. About 1.5 years ago, I visited a strip bar in Toronto...I hadn't been to a strip club in years and my wife encouraged me to go. I ended up getting a lap dance from two hot ladies. My wife wanted details, and it was a little hard for me to open up, but I did (I do my best to be completely honest). I figured she'd be a little upset about how intimate the lap dance was, but she was totally turned on by it.

When I got home from the business trip, we had the hottest sex we've had in years.
So that got us to talking. This also of course led me to share with my wife that a sexual fantasy I've had for 2 decades was to have a threesome with two women. I offered to take her or send her with a bunch of girls to a male strip show, but she wasn't really into that idea. She likes to be in control...she would much rather give a lap dance than get one. I said "Cool...we could actually do that!" Then she asked me "How would you feel if I was grinding naked on another guy?" I thought about it for a bit and answered "I'd be totally turned on by it". And I would.

From just talking about all this, if I recall we had some smokin' hot sex.
Since then, we've started fantasizing more and more openly with each other, now well into people we know (excepting very close long-term friends) and could possible engage in some play with. We've both written erotic stories for each other, and often flirt/tease other people just to arouse each other. End result: hot sex with each other.
We've visited some strip bars together and gotten couple's lap dances, we've partied with some acquaintances, flirted, teased, danced, fondled and groped a little, etc...essentially some very mild erotic play with others. End result: we have smoking hot sex with each other.
We've engaged in quite a bit of online flirting and a few cyber-sex encounters...I've encouraged my wife to take advantage of cyber-sex with a young "virtual boyfriend", and she's enjoyed it (and so have I). I've been quite entertained in strips bars and I really want to be fair to her, so I encouraged her and him to engage in whatever felt natural. End result: after she has a cyber-sex encounter with her virtual boy-toy, we have hot sex.
I probably don't have to say much more about where this appears to be headed, do I?
The cyber-BF has asked if he can come visit us...my wife has told me about his request, and we've talked about it quite a bit (for a month or two now). I've thought it all over carefully and I've said "Tell him to come on down." I've suggested to set the expectation that we'll hang out and have a few drinks and laughs...if anything erupts, we'll run with it. She likes him a lot as a person, and I know she'd essentially fuck his and my brains out. She's much more suspicious than I am, so if her barometer says he's safe and trustworthy, then I'm good with the safety element, even if it involves a little alone time for them. We're both in our early 40's and he's in his early 20's, so the "training a young stud" element has some appeal for her. And that's cool, if we're going to do this, I'd definitely want it to be as smokin' hot for her as it can be...her doing someone she's been burning for sexually is what I'd want for her. That turns us both on.
We've talked about fairness quite a bit, and I get to have a similar experience with her and another woman when the opportunity presents itself. I'm patient, so I'm in no huge hurry...like her, I would want it to be someone I really like and am turned on by (and someone who isn't shy about playing with both of us). We're both quite attractive people with engaging personalities, so I don't think finding a willing participant for me will be too difficult, although I realize it'll take a little time (I'm fine with that).
We've both talked a lot about how we think we would feel the next day and not just during. I'm quite positive that I'll be fine with it all the next day (and we'll probably have smokin' hot sex for quite a while afterwards).
Our sexual relationship has always been good...there have been a few dry spells here and there, but in general I think we have a really good sex life. I'm about the only guy I know personally who doesn't complain about the lack of sex or quality of sex. It's always been good, usually excellent, and sometimes just phenomenal. All these erotic shenanigans have done nothing but heat it all up. Our relationship otherwise has had it's ups and downs (we fairly recently worked through a very tough time, but managed to essentially wipe our slates clean and reset to zero...almost a fresh start, it feels like). I feel like our relationship has had some big swings in contentment at times over our 12 years of marriage, but overall I believe it's quite strong (we have ALWAYS managed to work through our problems somehow)...we both love each other and have a deep emotional connection. We have both always been faithful, we've never cheated on each other even when one of us might have wanted to. In fact, we've even gotten to the point of openness and honesty that we can admit to each other when we have crushes or infatuations with other people (and we end up using that in our fantasizing). We even encourage each other to flirt and playfully pursue our "crushes".
I've suggested that we go to a local swinger party and watch, flirt, maybe even make-out with another couple if we meet some folks we like, but not engage in anything actually qualifying as "sex"...then see how we feel the next day about it all. (I'd suspect "hot sex with each other", but you never know for sure until you just try it, I guess.) I'm not sure that would be all that "hot" for us though...we both like to really know and like the person's we have sex with. I've never been a pick-up artist nor has she ever been a pickup-ee. We both have to at least really like the respective person we want to do.
We've talked about setting boundaries for this first MFM...my wife feels that if we're going to do this, she wouldn't be satisfied without the whole enchilada (meaning everything including intercourse). After thinking that over, I see her point and I agree. I could be happy just doing oral with some of the ladies that I might end up with, but then I have to consider that some women may not want to give oral to me (although I love giving oral to a woman!), so I suppose I could feel a little left out if I gave her oral and essentially got nothing in return. Regardless, I do agree with my wife...if we're going to do this, why not just go at it and let each other have maximum enjoyment, right?
One thing I will say: even if we end up doing nothing, all the talking and openness and honesty sure seems like a great thing for our relationship. I feel good about us, and I guess in a way I want to reward us both for being good (ie. not having affairs, etc.) by us allowing ourselves to have some play time with others. We wouldn't want to do anything that would damage our relationship...but I just have this gut feel that after either encounter, we'd end up doing the usual...smokin' hot sex with each other.
I'm going to point her to this thread to see if she has anything she wants to add. (Her username is Sif, if you catch our little Norse mythology allusion. )
So, given all that I've written, are there any glaring red flags that pop up to you experienced folks? Please let us know what you think about starting with a MFM, following with an FMF, then re-assessing how we feel and where we go from there if anywhere.
Thanks in advance!
Loki