Dear Addy,

I’m in a long-term, long distance relationship. Until we can be together in one city again, my boyfriend and I have an open relationship. He has made some friends with benefits in the last year, but I haven’t found anyone and have had other things to occupy my time.

One of his friends with benefits is married. I met the couple at dinner about 6 months ago, and they later both expressed interest in a play session with me (and my boyfriend, but mostly me). I’m intrigued by this idea, but I’ve never been involved in one of these before. What should I know before going into this? Is it OK if I do a little drinking beforehand to ward off nerves?

Sincerely,

Totally Having Exciting Thoughts In The Shower

Dear THE TITS,

Fear not, young adventurous lass, I am still here! You can rest easy knowing that my cross-country move went smoothly. By the way, did you know that it’s been 85 degrees and sunny all week in Los Angeles? FYI: It’s pretty sweet.

Now, onto the issue at hand: Foursomes! (Man, you guys and your group sex questions…)

For those of you that consider yourselves fans of Love Is A Gamble (ha!) you’ll remember that a few weeks* ago I advised a gentleman interested in group sex to keep his pants zipped to avoid becoming entangled in a potentially friendship-damaging situation.

This case, however, is an entirely different box of peaches.

Here is what I’ve gathered from your inquiry, TITS: You and your boyfriend have a clearly established set of boundaries. (Props for that, by the way. Personal experience has taught me that long-distance relationships rarely survive unless both partners get around to addressing the difficulty of scratching their itches.)

I’m also not detecting any notes of jealousy or pressure to engage in an arrangement that doesn’t work for you. The couple that you’re interested in playing with has (1) already come to their own boundary agreements and (2) already (presumably) has some sexual chemistry with your boyfriend. It also doesn’t hurt that they’re laying it on thick trying to woo you. It’s always fun to realize that somebody wants your shit.

It sounds like the primary ingredient in this party soup is Fun, which is exactly what sex should be. (Whether you’re a group of two or a group of twelve.)

Now that we’ve satisfied the Ethics Fairy, let’s address your other questions. Is there anything that you should know about group sex? Sure. I won’t try to summarize an entire Internet subculture in one column, but there are a few issues that might come up:

1. Have a discussion with your boyfriend (and the other couple) about what’s allowed and what’s not allowed.

This is the only hard and fast rule I have for you, TITS. I’m sure your guy has his own idea about how this will play out, so make sure to enunciate your deal-breakers before the clothes come off.

2. Don’t be surprised if it’s not the end-all-be-all amazing Fuck Fest you had imagined.

Group sex can be chaotic. All those limbs and naughty bits and pieces in desperate need of attention. There’s a lot of repositioning, and the sheer mechanics of it can be exhausting. Then there’s the issue of who’s come and who hasn’t, who’s hard and who needs a rest, and the simple logistical problem of finding the moves that get a new partner off.

I’m friends with a Very Happy Couple who enjoy swinging and here’s what I’ve deduced from their stories: Hooking up with other couples turns them on a lot, but at the end of the day, they love going home to an empty bed where they can relive their sexy transgressions without the hassle of another set of balls hanging over their faces.

What I’m saying is: The group thing might be good, but the one-on-one afterward might be even better.

So go, explore that uncharted territory and plant your flag wherever you see fit. And feel free to have a couple glasses of wine to get your cylinders firing. Just try not to get too messy. It’s called social lubricant for a reason: A little bit is fine to help the process along, but use too much and you wind up losing all feeling.

What say you, readers? Do you have any useful group sex advice for all the newbs out there? Hit up the comments section with your finest war stories.

If you have a sexy question for Love Is A Gamble, send an email to loveisagambleTFT@gmail.com

*–Okay, months.

I am fortunate enough to be having sex with a certain person who is quite vocal about when he is about to have an orgasm and makes a lot of noise when he is actually coming. This is a big turn-on, and extremely convenient. But, in my previous dating life, it was always a big mystery to me when the moment was imminent and often even when it was actually happening. Sometimes when I was giving blow jobs, the guy would actually come, but not release much semen, so I would keep going until he said, “Ow, stop.”

It would have been nice to know what was going on, so I could adjust my moves accordingly, but short of just saying, “Dude, tell me when you’re coming” I never had any idea.

What clues should I have been looking for?

Sincerely,
Clueless in New York

Dear Clueless,

First of all, congratulations on finding someone who has eliminated some of the guesswork for you. Sex can be tricky enough, it doesn’t need any added ambiguity. Knowing when (or even if) your partner has climaxed is, arguably, one of the most important indicators of sexual compatibility. Continuing to suck and pound away after a (male) orgasm is sort of like continuing to dance once the DJ has stopped spinning. No one wants to be that guy.

Ladies, on the other hand, myself included, sometimes enjoy extended stimulus, which may lead us to the brink of another glorious O. Then again, some women can’t handle the intensity so soon after climax. Always remember that vaginae are like snowflakes; a veritable torrent of trial and error.

But you’re right; some people just don’t give you enough information to work with.  It’s nobody’s fault, not everyone can be the village screamer. But if you’re getting to the point where he’s stopping you because it hurts to continue, well, that’s just a shame and a half. Generally the physical signs you should be looking for are sharp, rapid intakes of breath, moans of increasing loudness and frequency, and a tensing of the muscles especially in the legs and pelvic region. When it comes to the mythical beast known as the cock, I find that most men become harder than diamonds right before their “big finish.” Plus it’s pretty easy to identify this handy indicator of a man’s pleasure:

If you had asked me this question back in your mime-fucking days I would have the following bits of advice to offer:

Step 1: Let your man know that you’re having a hard time figuring out when he’s about to come and it’s starting to make you feel anxious. (Note: This is what experts like to call the KEY STEP.) The worst time for this chat is mid-coitus, so try and time your approach so that you catch him in a relaxed mood.

Step 2: Ask if there’s some sort of way he could let you know as he’s getting close. It doesn’t have to be a vocal cue or cheesy safe-word, it could be something simple like a tug of your hair or a pinch of the nipple.

I’m glad that you found someone who makes his bliss crystal clear, since it seems that your silent partner’s lack of expression was frustrating you. I hope that your quiet riot found himself a mute princess and they’re giving it a go somewhere in Connecticut.

You see? All’s well that ends well.

If you’ve got a dirty, sexy, difficult question that you’d like answered, send an email to: loveisagambleTFT@gmail.com

Dear Addy,

I am a bi-curious guy in a weird situation. I have been friends with Cool Dude for many years during which he has gotten married and started a family with Sexy Chick. The three of us get along quite well. Recently, our gatherings have shifted in tone: After several bottles of wine, Sexy Chick starts to openly hit on me in front of my friend. She basically invited me into a three-way with the two of them. My buddy seems to be interested in this arrangement too. Up until this point I’ve turned her down.

Here’s the issue: While I am definitely interested in exploring the less traditional aspects of my sexuality, I don’t know whether it would be a good idea in this particular case. I’m not entirely comfortable with the fact that we’re all such close friends, plus I don’t like the idea of a wet and wild threesome when there are young children sleeping down the hall. Should I say yes, on the condition that we go someplace safe like a hotel?

Sincerely,

You & Me & The Bottle Makes Three

Dear You & Me,

The first thing I notice about your letter isn’t ZOMG HOT SEXY THREESOME (!!!) – it’s Hesitation, with a capital H. That should be the first sign that this isn’t a good idea. Regardless of what any stupid advice columnist will tell you, your gut is one of the best decision-making tools you have. And if your gut is telling you this isn’t a great idea then perhaps in this case it’s best to listen.

Listen, I’m not the type of gal to go around bashing the idea of a threesome. In my opinion, they’re sort of like chocolate-lava cake: Very delicious and decadent, but not something to be routinely indulged lest they lose their appeal. Dessert metaphors aside, I think that group-sex activities are best practiced with those you don’t already have a long-standing friendship with. Unless you plan on entering some sort of polygamous co-relationship with these two, best to find your jollies elsewhere. Having casual sex with a married couple with whom you are already close friends can lead to a number of possible scenarios, many of them being awkward and friendship-dissolving.

Let’s also consider your needs in this situation: Are you even attracted to your (male) friend? It sounds like the wife is the one putting on most of the pressure. Remember: Just because someone’s offering up booty on a platter doesn’t mean you have to say yes. (Wow, never thought I’d type that sentence with a straight face…)

Do people hook up with their married friends over bottles of wine and have great times doing so? Of course. Do I think you should explore your bi-curiosity? Most definitely. Do I think you should avoid a potentially sticky situation that could cost you your friendship with this couple? Yeah, I think it’s for the best. I don’t think you’re wavering because there are “children sleeping down the hall” (which, ew) but because deep-down you’re trying to spare yourself the confusion and controversy that comes after your best friend’s wife gobbles your junk and likes it a little too much.

If you’re interested in exploring your naughty boy-curious side, try a free dating site chock full of like-minded gents such as OKCupid.

Bonne chance!

Got a dating/relationship/sexy question that needs answering? LoveIsAGambleTFT@gmail.com

I have been married to the same woman for 24 years. She’s never enjoyed cunnilingus even though it’s something I’m good at and really enjoy doing. She is kind of a cold fish in the sack and it has always been a struggle to get her to be more experimental. Do you have any suggestions?

Regards,

Barking Up The Wrong Tree

Dear Barking,

Buddy, it’s been 24 years. At this point I don’t think any amount of cajoling is going to change your wife’s stance on the issue. I will assume, of course, that you’ve already tried asking politely and/or offering to finally clean the damn gutters. If you’re really, truly dying to get your face between a nubile pair of legs, get on the Internet and hire yourself a professional. (Helpful hints: Be discreet, be respectful, and steer clear of Craigslist.)

Happy hunting.

Got a dating/relationship/sexy question that needs answering? Send all of your burning questions to: LoveIsAGambleTFT@gmail.com

I am not what you would call super-experienced in things like love and romance. I make friends very easily, but when it comes to relationships I’m notoriously picky. I’m not really interested in casual flings and I’ve been quite unlucky in the past, so naturally I’m a little wary about opening myself up.

Recently I’ve gotten myself into a situation that both confuses and excites me: I started hooking up with my sister’s husband’s brother. He’s super-cute, it’s convenient because we’re all part of this tight little circle, and he’s very into me. I’ve never experienced anything like this before — usually I’m attracted to funny, outgoing dudes who ignore me and/or treat me like crap. But this one is different: He’s quiet and shy and sweet. He also likes to be touchy and affectionate. (Something I usually shy away from, but for some reason when he does it I don’t mind so much.)

What I need to know is: is this a bad idea? Should I be getting involved with someone so close to me? Is it weird that he’s so different from the guys I’m usually into?

All in the Family

Dear All in the Family,

Have you ever watched “The Real Housewives of New Jersey?” It is an important, sweeping family drama that teaches us all about the fragility of the human condition and the strength of family bonds. (Also: bubbies.) Thus, my expert analysis is that if it worked for Dina Manzo, it can work for you too. See, a few years ago, Dina divorced her first husband, so she moved into a big mansion with her sister Caroline and her husband, Albert. After Dina moved in, Albert’s brother Tommy started giving Dina the ol’ googly eyes. Dina wound up marrying Tommy, her sister’s husband’s brother. Now Dina gets to live in a mansion of her own with her daughter and her wrinkled, hairless pussy!

It’s like, the American Dream.

But honestly, this is what poker nerds like to call a coin-flip situation. Best case scenario, you two fall madly in love and y’all become one big happy family. Worst case scenario is an awkward Christmas dinner somewhere down the road.

In this case, based on the information I’ve been given (he’s treating you well and you seem to be responding to his advances positively) I’d say it’s safe to proceed with caution. Date the guy, have some sleepovers, enjoy yourself. People come together in all sorts of ways; it’s best not to question these things. Get to know him in a context that exists separately from your sister and her husband. And remember: Nobody is saying that you’re required to get hitched just because your siblings did.

But what about the fact that he’s not a cocky, gregarious funnyman like the guys you usually date? Having a preference for witty douchebags myself, I know how hard it is to open yourself up and just let guys be nice to you. After years of second-guessing yourself around those “life of the party” types it’s hard to accept the fact that a person could actually be into you without being a distant asshole about it. Believe it or not, these dudes exist! (So I’ve heard.) You’re in a unique situation because you’ve had a chance to get to know this shy guy in a family setting, where he is presumably more comfortable than he would be, say, at a bar talking to a complete stranger. I know it’s a strange sensation, but go with it: that’s the sound of being adored. Relish it.

Also, never underestimate the power of chemistry. If you’re not usually a touchy, affectionate type of gal and there’s something about his touch that excites you, there’s something to be said for that. I would definitely have a chat with him and mention that you don’t want to jump into anything too serious too quickly. Tell him that you enjoy his company and you’re interested to see where this is going, but make sure he knows in no uncertain terms that you don’t want to start picking out wedding china just yet.

Obviously it’s confusing when someone you’ve just started dating is clearly sprung before you’ve had a chance to figure out what’s what. Screws up the power dynamic, yadda yadda. But I’d say that due to the circumstances in which you met, this is not unexpected, nor should it you freak out too much. After all, it’s not like you just met the guy, you’ve had a chance to get to know each other without your respective game faces and from the way it sounds, you like him quite a bit too. Moral of the story: don’t shy away from a relationship simply because he/she isn’t what you think you’re looking for.

I hope you wind up with a hairless pussy of your very own someday. Good luck.

Got a dating/relationship/sexy question that needs answering? Send all of your burning questions to: LoveIsAGambleTFT@gmail.com

Dear Addy,

Hi. I am stuck in a bad situation and I’m not quite sure what do to. I recently moved across the country to live with my boyfriend. We haven’t been dating very long, but I really felt like we had something special. At first, things were great; we’re both sexually adventurous and agreed to an open arrangement. The only thing we required from each other was honesty regarding our extracurricular activities. Cut to: two months later, he unceremoniously dumped me for another girl that he met on the Internet. (He’d never met this woman before but apparently she had something that I didn’t.) Also, I found out that he’s been hooking up with lots of girls (and guys!) and lying to me about it. Now I’m stuck in a new city with no savings and a broken heart. A week after he dumped me, I resolved to get myself out of there and all of a sudden he started crying that he wanted me back. He bought me an expensive new toy, professed his love, and begged me to forgive him. I’m finding it hard to trust him, but I did uproot my whole life and want to try and make this work. What the heck should I do?

A Wii Bit Confused

Dear AWBC,

I don’t want to sound like a naggy Jewish mother, but there are so many things wrong with this picture that I don’t even know where to start.

Let’s break it down:

You moved across the country for a person you’ve just started dating.

This was perhaps your biggest mistake. I know in the movies it’s all kittens and puppies as soon as someone makes a grand gesture like a cross-country move (I’m talking to you, Mila Kunis in “Forgetting Sarah Marshall)” but listen: reality does not always favor the Dracula puppet show ending. The bottom line is that people should not move in together unless they’ve been dating for an extended period of time and are comfortable with each other’s assorted array of bullshit. Have you seen his bedroom and his medicine cabinet? Do you know how he takes his coffee? Do you know about where he keeps his secret stash of porn? If the answer to these questions is, “I don’t know, we haven’t been dating that long!” then it’s too soon to move in together.  I know even the best of us can be blinded by the power of a good lay, but for the love of God, don’t let hormones dictate your rental agreement.

He lied about his partners, despite coming to a mutually beneficial open arrangement with you.

This tells me that your guy probably gets off more on deception and illicit sex than the variety that an open relationship provides. I’m not going to rag on you for attempting a non-monogamous arrangement — I personally can’t see myself in one that isn’t, to some degree — but if the only caveat you agreed upon was honesty and he couldn’t even commit to that, it shows a serious flaw in his character. If you caught him in a series of lies this early in the relationship, what happens down the road when you’ve become considerably more invested? Not to mention the fact that if he’s having a bunch of sex that he isn’t telling you about, who’s to say he’s being careful and protecting himself every time? You’re putting yourself at great risk every time you have sex with him, especially if he’s having unprotected sex with both men and women.

He dumped you for an Internet persona and then reconsidered when you made plans to move on with your life.

Sad and typical. Sounds like your guy didn’t understand the theme of “High Fidelity.” Constantly chasing the elusive manic pixie dream girl is not a fulfilling destiny. Some guys (and, let’s be honest, some girls) never grow out of this phase. Wandering eyes are to be expected at some point in every relationship, it’s human nature. But let’s think about the context in which his eye wandered: you had just moved in two months ago, so your relationship was still new and exciting. He outright dumped you for a complete stranger, rather than discuss the issue like an adult. And as soon as you had made peace with his idiocy and vowed to move on, he changed his mind and showered you with affection and presents. This is not the behavior of a good boyfriend, it is the behavior of an indecisive man-child.

The best move you can make in poker is folding a bad hand as soon as possible. By which I mean, dump the untrustworthy fuck and run as fast as you can. Stay with a friend, get a second job, do what you need to do and don’t compromise your integrity for a shiny whirring box of empty promises. Good luck with your next move. (Oh, and definitely take the Wii with you when you go. Those things are awesome.)

Got a dating/relationship/sexy question that needs answering? Send all of your burning (or unexplainable itching) questions to: LoveIsAGambleTFT@gmail.com