How to go about having a casual fling?

September 18, 2011 1:17 PM

How to go about having a casual fling?

(Long, since this is anonymous and I won't be able to answer questions. Sorry.)

So, my wife has a medical condition* that makes sex difficult for her (pain during sex, medication that lowers libido) so my wife is just not up for sex very often. And by 'very often' I mean, like, ever, but she does on special occasions for my benefit.

*please take this as a given. I don't want to open this up to speculations that she might be making this up to not have sex with me. Trust me, I've been over that line of thinking, too.

So I'm kind of in this weird spot, where I don't want her to do something she doesn't want to do, but... you know what I mean? It kind of takes all the fun out of it for me if I know she's not really into it.

Anyway, she has told me for years that if I need to go "elsewhere," she's ok with that as long as I'm discreet. I haven't taken her up on that, because I'm not really interested in other women. Lately, though, I've been kind of missing that part of life. I'm not interested in the 'poly' lifestyle, and she has indicated that while she would be ok with occasional sex with other women, an ongoing relationship with another woman would not be ok.

My question is two parts. I know she's an individual person and this isn't really generalizable, but women: would you say something like that to me but hope that I would never do it, and then be crushed if I did? I've asked her that question and she says she means it, but... I still kind of feel like it's a trick in the back of my mind. Keeping it a secret, or don't ask/don't tell aren't really appealing options for our marriage.

For the second part: how would I even do that? I didn't date much before finding her and getting married. (Which I don't regret. We've had our ups and downs, but have a pretty good marriage.) How do you propose sex or even flirt more than casually with someone who knows you're married without turning into creepy looking-to-cheat dude?

Also, I can't really hang out in bars and look for one night stands by myself. I'm kind of an introvert. And I don't want all my friends knowing I'm doing this, so going out with friends and then hitting on women is, uh, not cool. Paying is too expensive, and I wouldn't even know where to go in the States without risking embarrassing arrest or dangerous situations.

posted by anonymous to Human Relations (11 answers total)

It's quite possible that your wife doesn't know herself whether she'd be ok with it. She may think it's fine now, but when it actually happens may suddenly realize that she can't deal with the emotions that she's having. Be prepared for that.

As for the looking part, good luck. There are a million guys on Craigslist looking for "just sex" right now. Get in line.
posted by Melismata at 1:34 PM on September 18, 2011 [2 favorites]

How often would be often enough? Could you take a yearly vacation and go off to some resort marketed towards singles/drinking/nudity/etc and ball away, and that'd do it?
posted by kmennie at 1:53 PM on September 18, 2011 [2 favorites]

You don't say much about how you feel about any of this. If you didn't date around and are the monogamous type there could be a whole barrel load of emotion waiting to thwack you in the stomach - are you sure you want to get into that? Men are not automatically immune to the emotional fall-out of casual sex - oxytocin is heady stuff and 'casual flings' can rapidly escalate even if neither person wanted or expected it to happen.

Rather than try and second guess your wife it might be worth thinking more about how you feel about this before you start worrying about to pick up women for sex. If you can specify your expectations it might be easier to help you out.
posted by freya_lamb at 2:24 PM on September 18, 2011 [1 favorite]

How to find this woman? No kidding around here -- I'd say craiglist. Write an honest profile, describe your situation as cleanly and straightforward as you can, and what you are seeking. I've never done it so I'm not certain that it'd work, but I have sold and/or given away things and/or bought and given things that I'd never have guessed would happen. Cast your bread upon the waters, etc and etc.

Melismata: "It's quite possible that your wife doesn't know herself whether she'd be ok with it. She may think it's fine now, but when it actually happens may suddenly realize that she can't deal with the emotions that she's having. Be prepared for that."

BING !!!! A winner here from Melismata -- no one knows what's going to happen when you open up this can of worms, not your wife, not you, not the woman who you get into bed with. There are lots of variables here. You can't get prepared for what will happen, really, as you don't know what's going to happen. I guess you can be prepared for that, for not being prepared.

the young rope-rider: "I absolutely do not agree that leaving your wife is the right way to go here unless you and she both agree that it is preferable to you having sex outside of the relationship. There is no reason to sacrifice your marriage because open relationships make some people uncomfortable. This is about you and your wife and what the two of you are okay with. I personally admire the care and commitment that you are showing towards your wife. ..."

BING !!!! yet again. While I do not think that anyone can know how they may react once they've entered into a situation such as this, it's absolutely totally between you and your wife, what you feel is best, what you believe is best, and then, in time, what you have experienced is best for you both, and for your marriage.

freya_lamb: ""Men are not automatically immune to the emotional fall-out of casual sex - oxytocin is heady stuff and 'casual flings' can rapidly escalate even if neither person wanted or expected it to happen. "

BING BING BING BING !!!! I'd give the big prize to freya_lamb here, sortof a repetition of the comment by Melismata and my response to it but I just want to drive it home -- you might think you're just going to roll around with someone, and kiss their face and their hair and hold them tight and have fun, but your heart can get involved, fast, whether you want it to or not, whether you decide to or not. It happens; it just does. I could never, ever be in an open relationship because I know this weakness in myself, that I could fall, and I'd be scared that my partner would fall, also, with whoever she might be with. I had one of the loveliest -- in so many ways, not just beautiful -- woman I've ever known ask me into bed with her while she stayed with her husband; I would not do it. Could not. Her I'd have fallen for, already had, truth be told, and if I touched her it'd kill me to have waved her goodbye.

So maybe this is all just projection of my issues onto your situation but I don't think so, I know that I'm not the only one who needs to keep things simpler.

Whatever you decide, I hope it adds to your life.
posted by dancestoblue at 3:06 PM on September 18, 2011

This is what escorts are for. In just about any sizable city in the US you can find an escort in the $350-$500/hr range that offers a "girlfriend experience" (GFE). Wear a condom, be polite and I guarantee you'll have a good time. The intimacy is fantasy, of course, but that seems to fit the bill here.

Go on theeroticreview.com and search for reviews of reputable escorts. You can even find etiquette FAQs for newbies.

I'm not saying it's riskless. But I've never had a problem, personally. It's a risk/reward trade-off. Whether you can sell it to your wife I have no idea.
posted by _spoonfull at 4:20 PM on September 18, 2011 [2 favorites]

Look... well... how can put this, all dudes who cheat are creepy-cheating-dudes to me (call it that psychic mustache), and there's no way around that-- but you're not cheating if she lets you. Then it's an open marriage with rules (not poly, yeah, but open). If you're open with your partners about you being in an open marriage and what you're looking for, then it's ok-- look for women on hook-up websites or put 'looking for friends and short-term dating' (say) and that's what you'll get.

The whole trick is whether you'd really stay casual, regardless. That's (I believe) unpredictable. Emotions always are, as is the future. You could stay married even if you've broken your covenant, but that will eventually break down your spirit. So no matter which way you go on this, you're treading dangerous waters. I don't mean just 'is she really ok with it', but are you. Regardless, all I want to say is, the moment you do fall for someone or get serious & don't tell her, you automatically suddenly become 'creepy cheating dude', so please don't do this, as you seem like a nice guy.



Honestly, I don't think you can do this on a permanent basis, as in, for the rest of your life, but I could be wrong. I mean, you don't sound like the type who'd do that comfortably, and if you do, you'll be changing who you are. That may be ok or inevitable. My feeling is that on some level people who can't view sex as 'just sex' basically remain those people, and if they go astray, they snap back eventually. There's another pov that men are all 'like that' and/or that all humans are like that if they're allowed to be, even if they thought they're not. Maybe that's so; that's the best hope for your marriage long-term-- that the pessimists are right. So, um, good luck with proving them right. A sex-life with a willing partner is something anyone should be able to get, after all.
posted by reenka at 5:47 PM on September 18, 2011

Isn't this exactly the kind of thing ashleymadison.com was made for?
posted by jasper411 at 8:54 PM on September 18, 2011

I've known married couples who had varying degrees of 'rules' regarding having relations with other people:

-I don't want to know about it
-I want you to tell me EVERYTHING
-Only if you share with me
-Only if you're safe about it
-Only if you ask permission first

I would consider sitting down and having a big discussion with your wife about it. Don't dodge around the subject matter during -- be frank and honest. Figure out what the 'rules' should be, give it a try once (or twice), then have the conversation again to discuss feelings, maybe adjust the rules. (Maybe she initially thinks she doesn't want to know, but then decides she does! Or you feel more comfortable not telling everything. Or etc etc...)

It's great that you've sort of had a discussion like this before. Please don't be afraid to have it again. If you would feel more comfortable discussing it in a professional environment, see a couples counselor. They're not just for couples thinking about getting a divorce.
posted by Heretical at 12:18 AM on September 19, 2011

This is not all that unusual. Plus you have your wife's permission. It's not poly if it's just sex, it's open. She has been clear she doesn't want to know about it, though.

Do not flirt with women who know you are married. I cannot begin to tell you how much pain you would be bringing onto yourself by doing that.

No, you need to find someone you like who you know is open-minded and explain the situation to them as you have above (and this takes balls) or you need to go the anonymous sex/escort route (and this takes money).

The second option is the more professional option leaving less room for emotional entanglements. There is a chance if you go with someone you know that either one of you will fall for the other one and want more.

But, as everyone else has said, it's all very unpredictable (but so is most of life).
posted by mleigh at 2:13 AM on September 19, 2011

It seems like you already have a intimate relationship minus the sex. Maybe consider going to a strip club. I know it's a tease but, sex with multiple partners are just going to open a can of worms you might not be anticipating. Strip clubs can be fun if you're not lonely.
Gage your sexual needs by starting out slow, see what satisfies you. Maybe by going to the strip club and jacking off to porn followed by some spooning and cuddling with your wife might satiate your desires when they arise. Don't automatically jump to having random hookups or escorts out of the gate.
It's cheaper and safer than other alternatives and, above all, you're still faithful to your wife.
posted by Bridymurphy at 8:02 AM on September 19, 2011

From a user who would prefer to remain anonymous:

Your situation resembles the one I had with my now-ex. We had the deal that sex was ok if done discreetly, and there were no emotional relationships. We had some more issues entangled with this which made it slightly more complicated. This lasted for a few years from my late twenties to my early thirties.

I found that it didn't work out so well practically. Even though my girlfriend was theoretically fine with it, I got the feeling that she might be hurt, and the guilt kept me from engaging in much sexual activity with others. When we talked about it, she reassured me that it was really fine for her, but when we went for a long time without talking, I started to feel uncomfortable, thinking her feelings may have changed. Does discreet mean out of sight/out of mind to you, or does it mean you should keep it secret to people you know due to the stigma? It's best if you can talk about it intimately and with mutual care, and from the begining state very explicitly what's ok and what isn't, what she wants to know and what not, things like that. If she wants to know nothing about it, that can cause some bad tension between you, apart from making the practical matters quite difficult.

The practicalities are difficult in any case, given your constraints and the fact that you're introverted. I am considered attractive, get approached by women fairly frequently when I'm out drinking, and get laid in spite of being a bit awkward now that I'm single. Yet when I was in a relationship, I almost never managed to close the deal and actually having sex with someone else. I didn't have that much time on my own to make it work. When I did, I felt guilty or just had problems explaining to the potential lover what the situation was, and without revealing anything to my friends.

I almost only had sex with other women when I was out of town. Spending the night in somebody else's bed while my girlfriend slept alone at home felt like betraying her. When you're away from home and get in contact with a woman, it can be clear from the start that sex is all there is to expect, and then you don't even have to explain your domestic situation unless it feels like a good thing to do.

This is a matter of your sexual taste, but if you don't mind it, I suggest you aim for women a bit older than you, say 40-50 if you are in your twenties. You don't so easily feel like a potential romantic couple then, and it's easier to be just sex partners. She and your wife might not compare themselves with each other as much as if they were similar in age. The bars where the 40-50 year old crowd hangs out and flirts are usually more suitable than younger places to hang out on your own if you decide to try it out. Meeting women in bars and such is otherwise hard if you cannot reveal anything to your friends, especially if you're a bit introverted. Can you have one single guy friend who knows, and who will be your partner and wingman?

I don't know about meeting women online, I guess it gets a lot easier on a site like Ashleymadison where people know the rules from the start. I never found a good way to say "I'd love to fuck you, but we have to plan it around my wife. She's ok with it though!". Unless it's clear from the start that it's a one-night or all-sexual thing, you have to mention your wife early on! If the prospective sex partner keeps showing some interest, you can hint at what your deal is when the opportunity arises.

I'm relatively cold-hearted and never had problems with emotional attachment to my sexual partners. Beware of that risk though, and keep in mind that it gets easier to avoid if the set of people you have sex with doesn't overlap a whole lot with the set of people you would consider romantically.

Anyways, I hope you're still checking the thread, and that you find something useful in all this text. Good luck to you, your wife and your lovers! I hope you find a way to treat them all well

posted by jessamyn at 4:58 PM on October 5, 2011 [1 favorite]