General Question

lou12345's avatar

Given permission from your SO, would you engage in sex acts with another? (NSFW)

Asked by lou12345 (22points) December 17th, 2015

This is a quick rundown, but here goes….

I have always been interested in trying anal sex with a woman. For one reason or another, through the years and various lady friends, it’s just never happened. My current lady friend and I are well on pace to be engaged in the next 6 months or so (though don’t tell her I said that ;) ).... BUT, she has made clear she’s not keen on the idea of trying anal sex, and likely never will be.

A few weeks ago I jokingly brought up the prospect of engaging in the act, and she sat me down and told me… seemingly 100% honestly and without any malice or what not… that she would be okay with me finding another woman to try anal sex with. I tested this notion, pointing out that if I actually did it she would rightfully be upset, etc, etc…. and she assured me she would not be, as she knows this is something I’m interested in and have been for my entire adult life… and she can’t provide it. The caveat being she would never want to know about it. EVER. AND it couldn’t be someone we know or that I am friends with or what have you (basically can’t be someone I see regularly and consider a friend).

Since that talk I’ve tossed the idea around, thinking about it. By in large I am very against the idea of sex outside the confines of our relationship (unless we are BOTH involved in it, IE 3 or more-way, something else I’ve never done, but I digress…).... On one hand I even try to justify it by thinking about the fact that very early on in our relationship (ages ago), she was sleeping with another man at the same time… prior to us becoming “official”.... which has always pained me a bit. That fact, paired with her express permission…. vs my own issues with the concept of “cheating” on my g/f, even with her permission.

But where would I ever find a girl like that anyways right? Well surprise surprise there is now a girl available. One whom I know to be clean of STD’s, free of drama, trustworthy to maintain the secret, and open for the idea of anal sex…....... and NOW i am truly faced with the prospect of this being a possibility.

And I’m battling with some conflicted emotions. My long time desire to try this sex-act, my loves desire to never try the sex act, her express permission, the bitter taste from what I take as an early indiscretion, the perfect candidate to be the other girl, my own feelings about the morality of the subject…. etc, etc.

What would YOU do put in my shoes…. or what comments/thoughts do you have?

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39 Answers

Response moderated (Unhelpful)
dappled_leaves's avatar

I think that you believe that you and your partner are headed for marriage, when in fact you both want very different things, and are probably doomed as a couple.

She does not want you to have sex with someone else. You are ignoring the fact that she does not want you to have sex with someone else, in order to get something that titillates you. She cannot deal with knowing that you’ve done it; you will probably not be able to keep it a secret. She will be devastated when you do it.

Just… how do you not see this, if this is the person you want to spend your life with? How does she not? You are both deluding yourselves.

Response moderated (Unhelpful)
DrasticDreamer's avatar

If this is legitimate, I say don’t do it. Not because I don’t think certain couples can’t successfully pull things like this off, but simply because neither one of you seems like you actually are that type of couple. So, it’s not a good idea.

I feel like if she was truly okay with it, she wouldn’t need you to guard it so closely after the fact. Couples that do things like this do often have certain kinds of rules (like not wanting it to be someone you both know, not wanting to meet them, etc.), but it seems to me as if she’s willing to sacrifice her real feelings to simply satisfy you and make you happy. Which is indicative that she’s simply afraid that if she can’t fulfill that for you, some part of her is very worried that it will become such a big deal that you won’t want to continue the relationship. She’s not going about it the right way – even if she doesn’t realize it – and if those are her true feelings, you definitely should not even consider experiencing anal sex with another person.

You’re at a point now in your relationship, since this has become such a large issue, that you need to ask yourself which is more important. How your partner feels, or your desire to experience anal sex. Don’t just want love to be your biggest desire now, genuinely ask yourself if it is, or if your fantasy takes precedence.

At the very least, you need to have another conversation with her about it before you make any decisions. Honestly, maybe have her read this page and ask her to feel safe enough to tell you how it makes her feel. If you do love her, make her feel safe enough to be 100% honest with you.

Seek's avatar

My personal philosophy: If you have to lie about it, it’s cheating. Lying with permission to lie is still lying.

If you do do it, you get to look forward to a long marriage of wondering if she will ever ask, what you will say if she does ask, and whether she’ll ever find out. The world isn’t that big, and she could easily meet whoever the person is that you’re considering. After all, she’s only one degree of separation from her, through you.

jca's avatar

Don’t do it. Are you so in need of committing this act that you are going to risk the relationship you have with the woman that you love? It seems selfish to me.

Not saying everyone who is in an “open” relationship is bad or selfish, I am saying in the circumstances you describe about your relationship, it’s selfish of you and I suggest you try to live without this act. Maybe in the future, your girlfriend/wife will change her mind, or maybe you’ll deal with not having it. Never say never.

chelle21689's avatar

I don’t think I would because things would get complicated for me. Also, my boyfriend is the object of my sexual desire lol. However, I do have some weird fantasy of him and other women but in real life I would be extremely jealous and not allow it. I’ve always been like this in past relationships. I think it would be too much of a headache to find someone that is attractive, a stranger, clean, and would be kept quiet unless it was some hooker lol.

If she’s serious about it then I don’t see why not. But she seems like she would be hurt if she did find out. Even if you didn’t tel her I think in some way she wild know…people pick up on subtle changes. That can drive someone crazy not knowing and always wondering. If tables were turned would you be ok with it? Maybe discuss that just in case she decided you “owe” her. Also, for some couples inviting others makes things messy and horrible which changes things. They think they’re not jealous but then when the time comes down to it they are.

Zaku's avatar

No, for similar thinking to what DrasticDreamer and others have said. I agree with DrasticDreamer that it does not sound to me like either of you are really polyamory-compatible. I’ve known and talked with quite a few polyarmorous people, some of whom are very intelligent/developed, and I think this sounds like it would be in the back of both your minds.So I think it would probably mess with your relationship, which I would think is far more important.

So since you asked, if it were me, no I wouldn’t, though I’d take the opportunity to get really clear about my feelings about it, and about the stuff that still bothers you about what she did earlier, and more importantly, about this upcoming engagement. Assuming I concluded what I wanted was the partnership, I expect I would find myself expressing great gratitude and appreciation for what she said, and then say that I’d decided not to do that, and to tell her that so she wouldn’t have to wonder.

I would also want to know more about what this mysterious too-serendipitous available anal sex woman is really about. Knowing also of crazy people, I would be concerned it could be a set-up somehow arranged by the future fiance or her friends or something.

jca's avatar

Good point by @Zaku. This other girl is just going to let you fuck her up the ass, out of the blue, no strings attached? Seems a little crazy to me.

SavoirFaire's avatar

First things first. If you have permission, it’s not cheating. Cheating requires you to go outside the mutually agreed upon boundaries of your relationship. Getting permission expands the mutually agreed upon boundaries of your relationship.

The fact that she doesn’t want to know about it complicates things. I disagree with @dappled_leaves that this means she doesn’t want you to do it. Non-monogamy comes in many different forms. Some people want to know everything. Some people don’t want to know anything. Some want to be able to approve or veto extramarital partners. Some just expect you to use good judgment. But whatever the case, any of these arrangements can involve genuine permission (and even genuine desire—some people like the idea of their partner being with other people, even if they don’t want the details).

I do agree with @Seek, however, that a lie is a lie even with permission to lie. So here’s what I would recommend. Talk to your girlfriend about this one more time. You don’t need to tell her there is a possibility of you taking her up on her permission slip. That would violate the “no telling” rule, after all. Instead, tell her that you wanted to check up with her to see if she really meant it—not because you’re definitely going to take her up on it, but because you don’t want there to be any misunderstanding. Also make sure she knows that giving you this permission slip is not a requirement for continuing her relationship with you. Permission under duress is not genuine permission.

If she confirms that she was serious, tell her that the necessary corollary to “no telling” is “no asking.” Tell her that if she asks, you will tell her the truth whatever it happens to be at the time (and by the way: if she ever asks about it, tell her the truth). So if she really doesn’t want to know, she needs to be comfortable with never asking. Then, with that corollary rule explained, ask her again if she’s serious. She needs to know what she is agreeing to—and so do you.

If you get through all of that with your permission slip intact, and if you honestly believe that you can do this without it damaging your current relationship, then go for it.

funkdaddy's avatar

Do this. Fool yourself into thinking you’ve done it last week. It was exactly like you imagine it to be. Make your story detailed in your head, get down to where, what time, what you told her you were doing then, how the whole day went, etc. Then spend the day with your possible life-long mate.

Are you relieved? Stressed? Do you want to tell her? Does she keep asking you what’s wrong? Is it out of the way for good, or are you trying to think of what’s next?

I think if you can fool yourself for one day, that will make your decision clear.

filmfann's avatar

Nope. I have turned down the chance when my wife set it up. A very attractive neighbor was miserable and lonely, and my wife wanted me to make her feel better. I told my wife that I wanted to honor my vows.
Now, 20 years later, I am glad I stayed true, though I occasionally think about the neighbor.

Bill1939's avatar

Been there, done that, wish I hadn’t.

ucme's avatar

Probably, although guilt would likely still play a part.

lou12345's avatar

I’m trying not to delve too deep into the details here, but a few comments/things I didn’t clarify well.

-The other girl is a perfectly fine candidate and isn’t crazy and etc yada yada. I don’t want to dive into this too deep, but suffice to say she is willing and notably not crazy. She meets all of the requirements listed…. and additionally she will no longer be local to us in a few months, so no prolonged crap really is possible.

-Maybe I overstated my g/f’s intentions to not know about this a bit. I shouldn’t have added, let alone capitalized, the “ever.” She intoned, maybe not even that specifically, that she wouldn’t want to know. I honestly don’t remember well enough to say with a certainty now that I think about it. But that was the impression I remember having so there must have been something said that gave me the impression.

-Building off the last point, I do think i will try to broach this topic with her again, to reaffirm how serious she was about the permission. The last time we talked about it I was largely too busy pointing out that I would never do something like that (partially because I was a bit insulted, and thought maybe she was either A)jokingly insulting my integrity as a b/f and what things I might try when left to my own devices, or B)she was upset in some manner and was telling me to do that either in an angry-sarcastic manner or as some have stated maybe out of fear of losing me if she didn’t relent somehow to my desire), and even if I wanted to how would I ever stumble upon such a girl that meets those requirements? It tumbled around in my head after the fact and the sincerity with which she made the offer (she’s not one to hide feelings of dismay if she has them)... then very randomly the girl came into the picture… and here I am.

-I also want to point out that my g/f and I are EXCEEDINGLY happy together and love each other dearly. So pump the brakes on this “oh you guys are doomed, woe is you, just break up now, blah blah coersion, blah blah, BS”..... We love each other and we share our deepest desires. One of mine is to have this sexual experience. It’s not as if I am or have ever been pushing it on her. Long ago it came up as a topic and I informed her of my desire, she informed me of her anti-desire, and that was basically the end of that. The majority, if not all, of the mentions of the topic since then (of which there have been few) have all been clearly in jest. The only reason I even consider the idea now is because of the sincerity with which she seemed to be making the offer. And she pointed out she (this I do remember) that she would want this to happen before we became more serious (IE engaged/married/kids/etc).... and frankly that would be my own wish too if it were ever to happen… While I may be able to try and justify a free pass from my g/f… my fiance or wife…. not so much.

-I again don’t want to delve too deeply into details of the people involved in this… but my g/f is very well settled emotionally. Easily one of the most comfortable-with-herself and strong minded people I know. It’s one of the qualities about her I love. This is not to say she is above feeling hurt or scared or all the other human emotions… but she does not feel the negative ones easily, and she is not afraid to express them when she has them.

jca's avatar

Here’s another idea not tossed around in this discussion, as of yet. How about you try to see if your girlfriend would be open to the idea of some anal play? See if she will be accepting, only if she’s wiling of course, to some play with your finger and lots of lube, and see if she might have been revolted by something that she may actually like? I think some people are closed off to the idea of anything anal, or may have had a bad experience that turned them off, maybe was painful, and they think this is awful, not for them, etc. Maybe she can be turned around and then you’d have the best of both worlds.

lou12345's avatar

@jca That would be an ideal situation. What VERY little play we have attempted, she was not a fan of. Part of it may simply be she wasn’t very open minded to the idea at the time, and I’ve not really tried to push the issue at all or warm her up much to it. Not really sure how I’d go about that even. lol

Zaku's avatar

It doesn’t sound to me like you really get some things about what’s really really going on here, such as:

* What’s the drive to do this thing about, for you? Are you in touch with where that feeling comes from, what it’s about?

* Have you fully processed and healed the feelings around her being with someone else when you were first dating?

* Do you have a full and complete feeling (not just ideas or story) for how the two above events are related for you, or not, and how that’s going to get healed, and how doing this other thing would complicate your feelings about what she did?

* How about her processing your upset about her being with someone else, how this might be related, and what impact you being with someone else is going to add to that?

Stuff like that. I would say that even if you think you’re fully in touch with everything (and your language doesn’t give me that impression), I’d recommend finding a great relationship counselor to support you two in your relationship, and in all of the above.

lou12345's avatar

@Zaku
-It’s a desire/interest of mine. I’m fairly sexually adventurous, and this is one thing I’ve not done that I’ve simply wanted too. If this doesn’t come to fruition and my g/f never comes around to the idea, it is by no means a deal breaker. It will simply be a mild regret later in life that I never tried it… I’m sure among several I’ll have, but I’d live.

-I still have a bitter taste to some small extent about her being with another man when we were first dating. But I have made peace with that.

-N/A and honestly not fully understood.

-There’s not that much upset there at all, if any, about that. I’m simply laying it all out on the table, and that is one thing I could justify putting in the “go for it becasue..” column. It was meant to be much more of a passing addition rather than a focal point of this conversation.

I’m definitely not worried about seeking a relationship counselor. This is easily the most stable and well grounded relationship I’ve ever been in… and I tend to date girls who have their head’s screwed on pretty well.

Seek's avatar

A dear friend of mine is a sexual health blogger (among other things that make her a rank expert on the topic).

I recommend This post, titled “You Want to Put It WHERE?!?” (OMG NSFW, seriously.)

Read it, and then see if she’d be willing to read it. Have a frank discussion on whether the advice is something you’d both like to take into account, and give it a few tries – NO PRESSURE.

LornaLove's avatar

Having a fetish or a desire is one thing, putting a partner you are planning to marry through this is another. I could say she sounded very ‘adult’ and understanding. I hope she is not just simply desperate, desperate to please you
There are things in the past that I wanted to try, perhaps they were better off in my head anyway, but I would not have entertained these whims if I had a steady partner. To my mind, that was my tough luck so to speak. Since having a loving trusting relationship was more important to me. I find the girl that is willing to do this with you curious to say the least, too.
Couples, of course, should communicate what they want, and work that out themselves, not ask random strangers for advice. Besides if you are asking us, I would say that you already realized it was a ‘no go’ for you. Don’t you?

Zaku's avatar

@lou12345 Ok, well it sounds like you think there’s little worry about. You might be right. In fact, this might be something you’ll regret if you don’t do, and the best circumstances to do it.

But since you asked for what we’d do, I’m sharing from my experiences. And I’ve learned that I have convinced myself I knew what was going on in my relationships, for me and for my partners, and only learned later what was really going on. And things like wanting to be with someone outside the relationship for me were signs that something was up for me which needed attention, and would be best explored with other people and with skills and techniques for rooting out the things we self-deceive about. Things like that can be great because they are clues for where we figure ourselves our and can lead to much richer lives – and not figuring what’s really going on for me has led to later bigger problems and relationship breakups.

In relationships, I’ve seen that the stuff we don’t really understand about ourselves, tends to come up in relation to the partner and brought to attention of both, one way or another. In an honest relationship with a healthy partner who looks at themself and does personal work, the relationship can be great for developing both people. But when I and/or the other person have avoided really looking at ourselves, it tends to lead to ever-growing resentment.

An invitation to sex with someone else but not talking about it, has me concerned in a few ways. With the right third party (counselor I mean, not other sex partner), this could be easier. I use the word counselor but I don’t mean in the context “oh no, we need to fix relationship with clinical counselor” – I know people who are awesome at the kind of advice you are asking for here – they’re professionals and have done lots of study and experience with relationships and polyarmory and so on, and the context would be rather like this thread and your question, only with these people who have tons of experience and study with people on these things.

Cruiser's avatar

I only wonder why you feel the need to come here and ask our permission to do this with another girl when you already have it from your girlfriend.

flutherother's avatar

On the one hand you are planning to get engaged, on the other you want sex with someone else. On the one hand you want your partner to know about it, on the other hand you don’t. You are against the idea of sex outside of your relationship and yet you are not. What you are proposing is not straightforward and is a bad start to any engagement.

ibstubro's avatar

The 300 pound gorilla in the room is, “What if you try anal sex with the 3rd woman, and you absolutely love it

Does that mean your relationship with your current girlfriend is doomed?
Does that mean you’ll continue to be unfaithful to your current girlfriend?
Or does that mean you’ll increase the pressure on your girlfriend to try this against her desires?

Commit to your girlfriend or don’t.

Cruiser's avatar

@ibstubro I had the same thought as you just did. Yeah, what if he truly likes it and wants to do it again. Will he hold true to his promise that the one time will forever satisfy his curiosity?

SavoirFaire's avatar

@lou12345 Is this a one-time only deal? Nothing you’ve said so far indicates that it is, but you haven’t really said that it’s a standing offer either. If you only get one free pass, then you’ll need to think seriously about what @ibstubro and @Cruiser have said directly above (though I would reiterate to @ibstubro that it doesn’t count as being unfaithful if you have permission). In any case, you should really take @jca‘s advice—especially if this is a one-time only deal. But you can probably wait until you try it out with this other woman. After all, maybe it will turn out that you’re not interested in a repeat performance (plenty of things that seem desirable in theory turn out to be not all that special in practice). If you do need some tips on how to work your way up from very light anal play to full on anal sex, I can PM you some resources. Your girlfriend has to be fully on board with the experiment, though, and you need to keep in mind that it is an experiment and not a commitment to going all the way.

DrasticDreamer's avatar

@ibstubro asked what I was going to, if no one else did. I’m glad he did, because that is an extremely important question you need to ask yourself, simply because it’s a possibility. What if you love it so much, you end up liking it better than regular sex? It’s a hypothetical, but it’s important to ask, even if you only end up feeling “meh” about anal.

Something else that I wanted to ask is: Do you think there’s any chance that your girlfriend is giving you the okay for this, simply because she knows how you feel about the man that she slept with before you were official?

You’re doing the right thing by talking to her again before you make a final decision. I still think showing her this page could be helpful, if only because it could give you guys a jumping off point and you could explore it all in depth together.

Ultimately, we’re just people on the internet trying to give you the best advice we know how to. We’re all well-meaning, but in the end, you and your girlfriend know each other far better than any of us know you two. Just be open and honest – in all other areas, I mean – and you guys should be alright.

msh's avatar

This will never, ever, go away nor be forgotten in a relationship.
Whether you do or not.
Awfully fast to find a willing partner. I bet that conversation was…odd.

Uberwench's avatar

Fluther can be so fucking prude sometimes.

Newsflash for the judgmental types: some women like anal sex. Some women start to really miss it if it’s been awhile since they’ve had it. And having a conversation with a woman about sex might reveal that she’s open to the idea. If the moral guardians had their way, no woman would ever talk about sex (her mouth being just another orifice to keep shut). But some us aren’t afraid.

Also, not every woman is a jealous holder of grudges. Fucking around with permission is a lot more common than most people think. Ttrust me, I’ve been the other woman for a lot of husbands and wives. And it’s way better than fucking around without permission. If monogamy is your thing, cool. Have fun with it. But it’s not for all of us. And a lot of you seem to be projecting your fears and disapprovals onto this guy and his partner.

@lou12345 I think you should go have your fun. Just don’t do it for revenge. As long as you make sure you really have permission and you’re doing it for you and not to get back at your partner, then do it. Remember to go slow and use a lot of lube. Enjoy yourself, and make sure she enjoys it too. That means having a conversation with her beforehand where you talk about exactly what she’s into. And if she has experience, you might even learn some ways to make it easier for your long-term partner to enjoy it if she ever agrees to try some anal play with you again.

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