The Rules of a Threesome

Rules of a Threesome: The Comfort Zone

Having written previously about how to initiate a threesome, I think it’s important to dig deeper and look at some of the potential hazards lovers must navigate once they’ve found the third person for their “ménage à trois.”

Pre-Game Report: Get in the Zone

While sensitivity, compassion and respect are foundationally important in all forms of sexual
exploration, they’re critical to threesomes, where the tastes and boundaries of each person
must be clearly communicated in advance to maximize “the comfort zone” for all involved.

I subtitled my jessica drake’s Guide to Wicked Sex DVD from Wicked Pictures Every Man’s
Fantasy because, ultimately, this has been my experience after years of interaction with my
male fans. So let’s get real. Men, if another woman is entering the sexual equation, keep
one thing in mind: It’s not all about you! If you’ve followed the steps outlined in my previous
Threesomes article, then this lady is there because she’s likely as attracted to your partner as she is to you. Everything you do physically and emotionally should reinforce this chemistry.

Possibly the most important rule to remember during a threesome is the Rule of Firsts. Always make sure your everyday partner is the first you go down on, have intercourse with, give an orgasm, or receive your semen. The more couples I speak with who engage in threesomes, the more I understand this to be the Golden Rule when it comes to bringing in a third person.

Halftime Report: First Among Equals

Once you are in bed, pleasure both women with as much mutual attention as possible. Be
generous! As you’ve already discussed boundaries and positions in advance, modulate your sensual choices accordingly – for example, if kissing isn’t within your new lover’s comfort zone, touch and caress her body passionately without “going there,” even if the heat of the moment is attempting to persuade you otherwise.

And of course, it’s the same once the penetration begins. If she seemed disinterested in, say, one-on-one missionary sex with you when specific positions were discussed earlier, don’t try to press the point once all three of you are between the sheets.

If you’re truly 100% present with both ladies as you move from each mutual act to another, you’ll treat each woman as “firsts among equals.” And chances are, you’re going to enjoy the way your sexual savvy is rewarded.

Post-Game Wrap-Up: Don’t Be the Last to Know

As this heady adventure becomes a happy memory,  be open and honest with your partner
about your experience. You may think you were the perfect gentleman, but invite her opinions, good and bad.

Communication and honesty are key, as always. Regardless of whether you both see more
threesomes looming on the horizon, candidly discuss what you got right and even, more
importantly, where you may have gone wrong – especially if any sexual “lines in the sand” were blurred or, even worse, crossed.

Of the three stages of sharing I’ve outlined here, the “Post-Game Wrap-Up” may be the most important of all, as it will probably dictate whether or not you and your partner ever go down this road again. So don’t just listen to her thoughts – hear them.

Be completely honest in your own feelings as well. This is why honesty is so paramount – if you don’t believe your partner has accepted your thoughts on the subject with sincerity, you’ll find yourself reminding her of it in a million ways.

While I touched on positions ever so briefly here, be sure to investigate jessica drake’s Guide to Wicked Sex: Threesomes – Every Man’s Fantasy for more explicit and varied examples.

I’ll be writing more on this topic in the near future, but in the meantime, I wish you the best as your own “Game Day” threesome approaches. If you stay within the comfort zone, not only will you cross the finish line, you’ll recognize it like a long-lost friend.

A Seminar on Threesomes in Toronto

Just last week I was in Toronto launching the premiere of my line of instructional movies on Adult 4U Channel 100. I had a series of meetings and lunches, did some radio (thanks, Dean & Todd!), and also gave a seminar on threesomes. I’ve done my seminars and workshops all over the world, and I always make sure people know even if it covers the same topic, each ends up completely different, depending on the part of the world, comfortability of the audience, the time of day, ratio of women to men, and even whether or not alcohol was being served. (Side note – I gave one hell of a fellatio workshop at a ladies night after the wine and cheese was served. I’ve never seen so many women replicating tongue and hand techniques with no hesitation!)

As it turned out, the venue was a local swingers club I may or may not have visited a few times prior. Certainly this group did not particularly need my advice on pulling off a threesome, especially considering the fact the club actually had a regular “Threesomes Friday” night every week. But once again, I was reminded I am not only teaching at these workshops, I’m learning as well.

I breezed through my intro and was well into discussing rules and boundaries, when I noticed some ears perking up. There were a few questions from the audience about how to go about choosing a person and setting rules, as well as some talk about positions and double penetration. Then I closed it out with a short Q & A session. Due to time constraints at the venue, I did my meet and greet upstairs, where I went to sign autographs and pose for pictures. As soon as I started it, I quickly realized my meet and greet would be an extended Q & A, and given some additional privacy, the majority of the questions from men AND women had to do with jealousy. I was really surprised, but once again, jealousy is a very normal emotion… I just didn’t think there, of all places, people would be prone to any type of insecurity. I was wrong.

Ego aside, I like being wrong. I usually learn a lot from it. Moving forward, no matter what the venue, I’ll spend more time discussing jealousy, and ask my audience more questions as well. It’s the feedback that helps me strive to make my line of instructionals even better for you.


How to Initiate a Threesome

A threesome is like the Holy Grail of sex, but much like the quest for the Grail, many people don’t know where to start.  If you are part of a couple considering your first three-way experience, there are certain helpful steps you can take.


First, you have to make sure your partner is on board.  As is the case with every aspect of a relationship (in and out of the bedroom), communication is key.


Often couples imagine a three-way while they’re in bed having sex, either watching an adult movie or talking dirty to one another.  This is a good time to gauge your partner’s reaction.  Are they even more turned on at the thought of another person in bed?  Is it a reoccurring theme?  If the answer is yes, a three-way may be worth pursuing, though there are still quite a few things to consider before green lighting it.


Do not agree to a threesome solely to please your partner or as a last-ditch effort to save your relationship.  Additionally, if either of you is exceptionally jealous, it may be best leaving the idea of a third person in the realm of fantasies.


Partners should come up with a threesome strategy before the act begins.  Be upfront about your expectations.  If something doesn’t feel right during the threesome, there should be a way you can alert your partner without making the other person feel uncomfortable or self-conscious.  Come up with a safe word or signal.


Also, you should discuss what you’re okay with and aren’t.  Is kissing the third person acceptable?  How about oral sex, penetration, anal sex, petting, cuddling, orgasms?  Some things are best left between the couple as a way to reassure your commitment.


The game plan should also include what happens after sex.  Decide whether the third person is allowed to spend the night and where they will sleep.  While opinions may change after the experience, you should also agree on whether the three-way is a one time deal or if possible repeat performances are in the future.


You can have this conversation over time or all at once, but it is important to have it.  Remember, it is an ever-changing negotiation.  What you try the first time may not end up as protocol in later adventures.


Once you come up with a three-way strategy, it’s time to consider who the third person will be and how to find them.  When choosing a potential third person, consider how uncomfortable you would be if the situation backfired.  There is a lot of risk for disaster when inviting your best friend, co-worker, or neighbor.


If you decide to bypass asking someone you already know, there are a few places you can try to meet a third person, some a bit more up front than others.  Bars and nightclubs are obvious options where inhibitions are lowered due to alcohol, however all involved should be sober enough to give sincere consent in order to avoid regret.


A swinger’s club or party offers an environment with like-minded people.  Here boundaries are respected, and for some couples, simply being in this environment is such a thrill it gives the sexual jumpstart they are looking for.


Websites are always an option, though come with plenty of uncertainties.  You never really know whether someone is truthfully representing themselves.  Meeting them first during the day in a public place is strongly recommended.


An option rarely addressed is a legal brothel, such as the ones in Nevada.  There a couple can settle in, be introduced to a variety of possible partners, talk a bit, and negotiate what will happen and how much it will cost.  Brothels take the guesswork out of the equation and guarantee a sure thing.


The important thing is for both people in the couple to agree on who the third person will be, which reinforces the integral nature of communication.  Once you’ve agreed to pursue a three-way, developed a strategy, and found the ideal consenting person, the Holy Grail is in sight.  There are many helpful tips for the actual act, including positions, but that’s an entirely different article… or you may pick up a copy of jessica drake’s Guide to Wicked Sex: Threesomes on DVD.