So You Want to Try a Threesome…

One of my favorite old BritComs is Coupling (sort of the British Friends). In one of the episodes the highly sexed Patrick announces that he is going to dump his girlfriend of the moment because she is too naive. She ruled out a threesome at the first mention of one! Patrick insists that threesomes don’t really happen, they are just a fantasy that a woman must prolong up until the point she has a baby.

So, okay, looking beyond the misogynism and stereotypes here, the show does highlight the common fantasy of threesomes and the belief of many people that these are not a thing most people ever get to experience. For many people, threesomes are relegated to the fantasy world of porn or Cinamax and HBO. But wait! They are real and it is possible to have a non-awkward threeway encounter where everyone has fun! (stay with me)

Fantasy vs. Reality

The fantasy threesome as portrayed in most media occurs without much negotiation or thought. Often the third party is a surprise for one of the members of an established couple. After a few initial moments of hesitation, the three people fall into a night of ecstasy. That is not how a good/non-awkward threesome happens.

You need to communicate with your primary partner (the first partner you discuss the threesome with for our purposes) about your needs and desires. If you and your primary partner are actual romantic partners (dating, married, long term relationship) this is especially important. For those of us coming from a monogamous culture, not experienced with polyamory or non-monogamy, we often hold unexpressed expectations around sex which are challenged by a threesome.

If you are in a relationship where you do not discuss sex and sexual needs often, this can be a difficult conversation to have. However, you have to have it in order to have a good threeway.

Don’t expect the first person you think about to join you and your partner to be “the one.” They may be very interested. They may only have expressed interest in one of you. They may not know you think about them in a sexual manner. Avoid objectifying the person you and your primary are fantasizing about in the run up to asking this person. Do not get so involved with your fantasy about this third person you forget they are a person with needs and feelings too!

Set Expectations

Before you approach a third party to join you, work with your primary partner to set expectations and any boundaries you might need. These will vary with every coupling and can change for a couple over time. Are you okay with your partner having oral sex with another person? What about penetrative sex? Will all three of you engage in sexual activities? What about initiating the play? What methods of safer sex will you use, if any?

There are a ton of questions to ask and think about prior to setting up your date. I have included a list of possible questions to talk about at the end of this post.

Also, if this is your first threesome with someone, the sex might not be fantastic. Some people have great chemistry in bed early on in a relationship. Some people need time to warm up. You know your own style. You may know or may not know the style of your other two partners. Think about what happens is the sparks don’t fly. Or if the sparks fly between the other parties but not you. How will you deal with that.

The Third Person

Once you and your primary partner have chosen a third person you will want to engage with, approach that person. You may want to have one of you go out on a date with the third party and bring up the subject. You may know the third person well enough to set it up over text of a phone call. You may be searching for the third party online or looking at hiring a professional.

Make your intentions clear. Hinting around the topic in vague and uncertain terms can lead to mixed signals. At some point you are going to have to say, “Would you like to sleep with me and so-and-so in a threesome” or something to that effect. If you never come out and clearly state your intentions eventually you (and possibly your partner) will simply come off a creepy.

Make sure you indicate if this is just a one-time thing, if you are looking to make an emotional connection as well, if you want an on-going relationship of some kind with the third party, or if you simply got a great referral for a pro and need to set up a night.

The third person is a real person with real feelings. Too often folks looking to explore polyamory as a couple will look for their “unicorn” and the obsession of getting their perfect bisexual woman becomes the nasty habit of unicorn hunting. The problems with unicorn hunting are many and I have said much more in this post.

The Night

So you have found your perfect third person! You have set a time and location. Cool beans. Now you need to get ready.

Depending on the situation and location, you will need to consider some or all of the following:

  1. Do you need to get STI tests prior to the hook-up? If so, you will need to do that at least four days prior to the date.

  2. If you are hosting, do you have clean sheets and towels? Nobody wants your first sexy night together to be shared on sheets filled with cat hair.

  3. Shower, shit and shave. Basically, make sure you take car-e of basic grooming and prep.

  4. Got condoms (or other safer sex stuff)? Make sure you have the necessary safer sex items. This can be condoms, dental dams, lube, safety scissors, gloves, fire exstinguisher and whatever else you will be using.

  5. Water. We all need to hydrate. It is good to have water and possibly other stuff to drink on hand.

Reduce the Awkwardness

Threesomes can feel awkward the first time. Hiring a professional is a great way to make this easier since a pro is used to guiding folks through these big moments. If, however, you are hooking up with a friend, a potential new partner for your burgeoning polyam tribe, or some hottie you have been chatting up on Tindr things may be a bit rocky at first.

Think of hosting a threesome like hosting a dinner party. A little music, a few candles, some good lighting, maybe a light snack will all ease the tension Most people like to chat a bit at first so allow for some conversation.

When you feel the moment is ripe, the person who agreed to initial the threesome should step up and do their job! This generally is something like starting to kiss one person and inviting the other to join you both. If you are in a D/s or other power dynamic, this may be the D-type directing the submissive to start kissing or making out with the third party. This can start with cuddling on a couch with the three of you and allowing hands to start wandering while you all watch the Great British Baking Show (shout out to all of my readers with Paul Hollywood fantasies! I see you!).

Allow the session to progress at its own pace. Do not try and jump immediately to penatrative sex or oral sex. If you know your primary partner generally needs a bit of a warm up, allow for foreplay. Ask your third party for feedback (“does this feel good?”, “Do you want me to play with your breasts more?”, “Your moans are hella sexy! You like that don’t you.”)

Plan for the Worst

Hopefully, and most likely, your night will be wonderful and everyone will leave happy. However, this is not always the case. As with most sexual encounters you should have a plan in place if things go sideways.

If, for any reason, any member of the threesome wants to stop, STOP. This is non-negotiable. If anyone indicates they need what is happening to end immediately, you have to honor that. Period. No room for debate. If you pressure the person to continue or continue after someone has indicated they need to stop it is rape.

Do not count on everyone reaching a climax. The orgasms of the three of you are not the point of the evening. Yes, orgasms are great! However great sex and great threesomes does not require any orgasms happen. If one or more of you are not reaching climax and don’t want to continue the activities, that is perfectly acceptable.

Talk to your partners beforehand how you want to handle bodily fluid contact. You may all be comfortable with barebacking (not using any barrier protection methods). You may decide that one or two or all three of the people have to use some sort of barrier protection. If this is the case, have a plan for what happens if someone who is supposed to use barriers does not. Condoms break and slip off. People toss dental dams to the side. In the heat of the moment someone may decide not to use a barrier. Have a solution in mind for if this happens. (This is why STI tests BEFORE the night are pretty important.)

Afterglow and More…

After all the fun is over, one or two of you will go on your own way. If you have hired a pro, a thank you and a good tip are a great way to end the night! If you are hooking up with a relative stranger on Tindr, some kind words and clarity if you will be in contact with them again is appropriate. If it is a friend or someone in your social circle, plans for the next coffee date or a “See you at the Bon Jovi Cover Band concert” will work. And maybe pay for their Uber.

You and your primary should debrief after the night is over. It may be that night. It may be over breakfast the next morning or sometime in the next week. Talk about what you liked, what you didn’t like and how you feel. Be honest. If you enjoyed the sex but don’t want to repeat the experience, say that. If you are disappointed say that. If you discovered you have a new boundary or are upset about something, be honest with your partner. If you now want to start hosting threesomes every weekend, say that!

Communication after the threesome is as important as it is before one.

Personal Note

I have been a part of a lot of threesomes, foursomes, and more-somes. A few have been hot and wonderfully fun! Most result in average sex and I could take or leave them. A few have ended up poorly. Communication before and after the event is critical.

Over time, I learned what I enjoy and what I don’t enjoy in a 3+ encounter. Communicating that to my partners has helped improve the quality and enjoyment of threesome (or more-somes). They are fun to try and can open up new sexual frontiers (or let you know you are cool not doing one again).

Hope you have a ton of fun at your first menage a trios!

Questions To Think About:

  1. What are your general expectations with a threesome?

  2. Ideally, how would you like to see this to play out?

  3. What type of partner do you see bringing into the threesome? Someone you know? A Stranger? A Pro?

  4. Do you want a longer term connection with the third party?

  5. What types of activities do you want to include? Oral sex? Penetrative sex? Voyeurism? Exhibitionism? Any kinky play or fetish play?

  6. What types of safer sex is important to you? Do you want/need STI tests? Do you need to go buy barriers, gloves, lube, safety scissors, first aid stuff?

  7. What happens if there is a break in a barrier or failure to use one?

  8. How do you feel about your partner climaxing with the third party?

  9. Are there things which are off limits? Use of pet names? Sharing robes/sleepware? Sexual activities? Drinking? Drug use?

  10. Do you want to have dinner or drinks before the event? Where will this happen?

  11. Who is responsible for talking to the third party about what you want in the threeway?

  12. Who will initiate foreplay or sex during the encounter?

  13. Practical considerations: finding a baby sitter, clearing the house, changing the sheets (basically a chore list)

  14. Check in with how each of you are feeling about the threesome after talking through these questions.

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