How to not fuck up monogamish

So in case everyone is not a Dan Savage fan, the term "monogamish" is one that he uses to describe a couple that mostly only fucks each other but occasionally have their fun on the side. My boyfriend and I have been monogamish in theory for the entirety of our 4 year relationship but now I want to make it real.

The whole thing started ridiculously enough with me going out for drinks with an old friend. I'd always found him attractive but never had the nerve to act on it. Far too many beers later, I was confessing that he was super hot and learning that he'd be down, too. He knows my boyfriend and they get along and I am not the type of person to cheat so I forced myself into a cab and told him I'd talk to him later and sober.

The next day (yesterday) I talked to my boyfriend. We have had open communication and a lot of really hot fantasies but never before have I presented an actual person that I might want to fuck. It turned out he was not surprised at all - the looks I hadn't realized I was giving the other guy were quite familiar to my boyfriend. He was only surprised that in our long history (the other guy and I have known each other for over 20 years) we have never hooked up. He said it was about 80% okay with the idea and that he needed a few days to think on it, but it would probably bump up to "have fun, be safe," just don't do any sneaking around.

Today I saw the other guy for coffee, with my boyfriend's knowledge and blessings. We talked and ended up hanging out for most of the afternoon. Neither of us wanted to do anything physical before 80% turned into 100, but our friendship was thankfully not ruined by my artless drunken confession, as evidenced by a really fun day of hanging out with mild flirting.

I guess my question is, this seems as close to perfect as it's going to get so far, how do I not fuck it up? Does anyone have stories of successful non-monogamous relationships or pitfalls to avoid? This whole thing is so new but so incredibly sexy - after 4 years routine starts to set in, but with only the tantalizing "maybe" of this, I find myself counting down the minutes until my boyfriend gets home so I can fuck him senseless!

Sounds to me like the stage has been set for a long time and you're handling it very maturely so far. The main pluses I see are the fact that you've agreed in principle a while ago that this is something you would both be OK with were the opportunity to present itself. Now that it has, you've further done it right by talking about it with your partner, seeking his blessing, and waiting patiently for him to get used to the idea before giving the go ahead. As long as partner #2 is on board and understands his place in the whole thing I don't see how you can get into too much trouble. There's always an element of risk of course any time you start messing with feelings and emotions and tinkering with relationships, but then that applies to more vanilla type relationships too.

Any more questions? If not, then you may proceed.

Let us know how it goes.

You might find something useful in the "what is poly" thread: http://forum.literotica.com/showthread.php?t=1085383

If you haven't had much experience with the "ish" part of it, I'd recommend being careful about what you promise to your boyfriend. Some people go into arrangements like this with an agreement of "won't develop feelings for anybody else" and that's impossible to guarantee, especially when the somebody-else is a close friend. IMHO it's better to base agreements on tangible stuff that you do have power over.

The line between fantasy and reality are vastly different! I would caution you to move forward with the utmost care. While your boyfriend might be ok with the theory of you finding cock outside of your relationship, the reality could be completely and devastatingly different. You have to be absolutely certain in your relationship and communications with each other before you bring another into the mix, whether it is for random hook-ups or as a 3rd.

Whatever you decide, make sure it is what YOU want to do, and that the decision isn't swayed by either the boyfriend or the object of your affections. Good luck, and report back.

and then reality hits.

When I was separating from my ex-wife, we had talked about "dating" each other while we worked out our relationship issues. What we hadn't discussed was whether one of us wanted to date other people. This hit home when one night over drinks my ex confessed that she had been out with someone else she met in the grocery store, and they had "a couple of dinners". I stupidly asked if she slept with him, to which she responded, "that's none of your business". That was code for "yes, I fucked someone else".

My heart sank, and any motivation I might have had to fix the relationship was now colored with images in my mind of my wife giving herself to someone else. I couldn't stop the images of all the things we did together . . . only with another man.

So, my advice is, think REALLY carefully about this, and talk about thoroughly with your boyfriend beforehand.

You current situation sounds a lot like how my polygamous marriage started.

If you want to know the quickest way to fuck things up the answer is simple: lie and stop communicating.

Seems to me that you and your boyfriend communicate well about each other's desires. This is great! Make sure that communication carries over to your friend as well.

The other thing is trust. Without it, you'll have nothing. Both of you need to be 100% certain that if you go through with it that you can still trust each other afterwards. Jealousy CANNOT exist in such a relationship.

My other advice: if you do decide to go through with sex with the other person, make your boyfriend a part of it somehow. I'm not saying a three-some, though that could work too, but at least involve him somehow. Have him watch, be in the same house knowing what you're doing, etc. Exclusion breeds jealousy. You don't want that.

I think you are going to have to go down this road and see what happens. Will it turn out to be the best thing you ever did? Maybe. Will it turn out to be the worst thing you ever did? Maybe. The point is if you don't do it you will always wonder.

I've been successfully navigating polyamory for a long time now. And your situation sounds pretty typical for newcomers. What would I suggest?
Talk to your boyfriend about exactly what makes him uncomfortable with regards to that 20%. You may or may not be able to allay his fears, but get the communication flowing freely.