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Considering an Open Relationship-- Questions to Ask First

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Rookie Scribe
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Hi,
So I have been seeing a new guy for a while and he recently talked to me about his ideas of monogamy/expectations in a relationship and told me that he is really only interested in pursuing an open relationship.
He presented this in a very open, honest, and mature way, and asked me to please think about it and think about what kinds of expectations I have. (Note: By open, he means dating other people, not having casual sex/hook ups, and it would always be something discussed beforehand.)

Now personally, I have been "dating" openly for more then two years (since my last very significant relationship). Dating multiple people at once does not bother me at all. I have not, however, gotten serious or too emotionally involved with anyone in this time.
I am really starting to like this new guy though, and would like to keep seeing him and become closer with him.
I told him that I'd like to talk more about what being in an open relationship means and want to go into the conversation with lots of questions.

I was wondering what you guys would want to know/what boundaries you would discuss right upfront.

So far, on the "to ask about/discuss" list I have:
Casual Sex/hookups-- when, if ever, do they happen, how/do you share about them.
Safe sex practices.
If he is looking for a primary relationship that is not closed, or seeking multiple relationships.
If he was in a primary relationship would he want to actively seek other partners vs. if an attraction comes up he'd like to pursue it.

Thoughts? Warnings? Questions? Encouragement? I'd love to hear.
Active Ink Slinger
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I guess the most important thing is how you feel about it. It sounds to me as if you've been where he is now but are ready to move on to something more serious.

Are you in danger of being not much more than a friend with benefits?
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The Linebacker
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I definitely advise regular check ups with the doctor. Don't wait until you are peeing bullets. Maybe use BeenVerified and other sources to check out your new casual hook ups so you don't get stuck with a serial killer or psycho stalker.
Rookie Scribe
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Buz, I'm not sure you read/understood the point of the post... This is a person I know personally, have been dating, and am on verge of becoming more emotionally involved/attached too who practices polyamorous relationships... I'm not concerned about that he is a serial killer.
Internet Philosopher
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I would probably ask myself how am I going to feel when Saturday night comes and Im at home while (he) is out with another. Am I going to be miffed because it was 'my' weekend? Is it going to bother me that I dont dare call for fear of hearing her in the room when he answers? Am I going to wonder if she was there all night or if maybe she is willing to do things sexually that I wasn't comfortable with.

Jealousy can be a sneaky poison. It can show up very powerfully when you least expect it. Unless you are sure that you can answer those questions, and that he can too, you will be walking the razors edge. Good luck to you though. Most open relationships fail eventually.
Rookie Scribe
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Thanks Milik.
I am going to see him this weekend and have a frank conversation about not being able to predict how I'll feel if we become more serious. I do like him, but that's a lot of patience we would both be asking of each other very early on in a relationship.
I'm disappointed though, he really is what I was looking for otherwise! Oh well!
Lurker
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I would have much deeper discussion. Does he want to live with you and play the field? A swinging lifestyle? Or does he want to live alone with a night or two in your crotch? Does he want to shack up and both of you have nightly romps to the bar and bring someone home and go to different bedrooms? Find out exactly what he has in mind and decide for yourself if this is something your willing to do.
Active Ink Slinger
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Hmmmm.....this is a serious one.
If you read my profile you'll see that I am a dedicated swinger and multi partner sexual person, so my response comes from that perspective.

Over the years I have encountered many couples in this and similar situations.The relationships that survive are those where both partners want the same thing and accept that from their partner.

The strongest relationships are those where a couple can share these things together. You are both trusting enough that you can have your partner go out on a date with someone else, knowing that they will come home to you, and you can go out on a date knowing that you will come home and love your partner even more for giving you that freedom. It has to be 'want' on both sides; and I don't mean sexual 'want' but the want of satisfaction and happiness for your partner. In return, your partner has to have the same feelings of wanting you to be happy and satisfied.

I'm not qualified as a counselor, just experienced from a couple of decades in the swinging and group sex lifestyle. I've seen relationships bust up through jealousy brought on from inequality of freedom for each partner. Similarly I've witnessed many that grew into inseparable bonds because both partners 'got it'. The strongest and happiest relationships I know are couples who share this and understand what it means.

From what you've written, it seems that you've been around the block with some FWB's and have no issue with that. I assume your partner has done the same and you have no issue with that. The test is if you can do it together. Can you watch your partner fuck someone else and be happy for them? Can he watch you fuck someone else and be happy for you? Until you know this, you will never progress to independent dating. Sitting at home wondering who he's with and what he's doing will likely tear you up. You have to know that he is fucking someone else; you've seen it before and you hope he's having fun. In the morning, he comes home, washes his dick, tells you what a great or dull time he's had and life goes on. Same for you. If you've been out and partied with two or three guys, come home dribbling cum and tell him about it, he has to be happy for you too.

My recommendation is for you both to go to a soft swing party or club where you live. Have a threesome both ways; an extra guy for you and then an extra girl for him. Be together in the moment; be involved. Hold his cock while he pushes into her. Have him fold your legs back when the guy penetrates you. Watch your partner while he is in pleasure with someone else and examine your feelings. If you are jealous and feel dead inside, then it's not for you. If you feel good about it and enjoy the freedom of pleasure you get from it, then explore it further.

From what I've seen, jumping into independent dating (let's be honest; fucking) without being comfortable in the shared sex experience, is a recipe for failure.
Hope this helps you on your journey.
Lurker
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Well, I can speak for our experience. We married and after about 5 years, we began moving toward an open relationship. We had been in a number of threesomes, in the early years. At 5 years, we began to swing lightly at first, then gradually it moved forward until we were involved in a group that met monthly for an all night party. Both of us bi, we each had our "lover." It seemed to make our personal sex better, she was more willing to do certain things. We went on trips, not together, with friends that would get very naughty. We were as open as we could possibly be. We went through it without a hitch, however, some of the other participants eventually had problems. Our openness was sexual, not really wanting to have someone different to go on dates and one night stands with.
I would advise you to maybe try it out, remember, you're not too emotionally attached. If things go bad, get out. You've already stated that you have dated several, not just one. Lines get blurry and you make find you're way over the line at some point. He already wants to fade the line going in so if you do decide to do it, keep an open attitude that you can get out before drama begins to build. And let him know you'll jump as soon as you don't feel right about it anymore.
Active Ink Slinger
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The OP was last on here 6 years ago, so I doubt they still need our advise. Further, while I know what works for us, I wouldn't presume that it's going to be right for very many other couples.
Active Ink Slinger
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what works for you, with my husband and I we enjoy threesome, also swapping, husband is a voyeur which suits me as I'm exhibitionist