How To Have A Threesome, According To Men Who Have Been There, Because You Really Shouldn't Go In Blind

Here are two facts about threesomes: 1. they’re super hot and, 2. they are minefields. These days it seems like more and more people who maybe would have identified as fairly “vanilla” are joining the sexually adventurous in the pursuit of threesomes. I am so all about it! I think that threeways are super fun and a great way to learn more about yourself, your partner (if you have one), and your sexuality. However, when it comes to fact number two, they’re also potentially hazardous to your health and happiness. So what are some good threesome tips to ensure that your experience is more on the super hot than the super awkward side of things?

I’ve enlisted the help of men who have some experience in the area. Some, like sex educator Reid Milhalko, have a lot of experience.

“I’ve been very fortunate in that I’ve had at least 150 threesomes so far in my life, and the one thing I’ve learned is that initiating threesomes are always awkward at first!,” Milhalko told me via email. “Whether it’s inviting people to have a three way or making the jump from everyone sitting on the couch looking expectantly at one another to ‘the sex’ happening… Initiating threesomes always feels like a seventh grade school dance on steroids to me!”

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Milhalko has made helping you get out of that awkward spot part of his job and you can check out his work on the topic of threesomes here. For more advice on the topic, keep reading as these 11 guys share their top tips for making the most of your three way experiences.

1. Joe, 44

"Make sure everyone gets a turn at 'being in the middle', i.e., getting pleasured by both others. That way no one feels left out!"

2. Morgan, 32

"The first really important thing is to have a conversation with your main squeeze about expectations. Like, for MMF or MFF threesomes, is the partner that is about to confront similar genitals to their own actually bisexual, or just a voyeur? If they aren't bisexual, are they truly comfortable being naked around this other person, or are they just doing it for the sake of their partner? This is the place where people usually gloss over things and end up having a bad experience or feelings of regret afterwards. Decide what you are both comfortable with ahead of time, and be sure to clearly communicate that to your invited third person ahead of time, so that their expectations match your own.
If you are the one who is being invited to join a couple, be sure to ask lots of questions about expectations and boundaries. An all-too-large number of couples give threesomes a shot in order to make one of the pair happier, while the other partner is miserable the whole time. Be sure you ask questions to ensure you aren't entering that kind of a situation, or you'll end up having sex with one person while their partner stands in a corner crying, and nobody wants that.
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A threesome is logistically awkward! It's just plain going to be awkward and different than one-on-one sex, because the three of you are going to be sitting on a couch watching Netflix or whatever, getting into the mood, and somebody is going to have to kiss somebody else in front of a third person to get the ball rolling, which is not normal for most people.
The solution to that awkwardness is to have a good sense of humor and be direct. Make a joke about it, defuse the tension, be yourself. Communication is super important, and a threesome just plain involves more talking than most other sex. If you aren't able to talk frankly about sex and positions and how to get your butt over here while my head is over here, you really aren't going to have fun. That's just the facts of the matter, and you need to accept and embrace that if you want to have a good time. Somebody my wife and I recently hooked up with texted me the next day to thank me for being so direct and forthright, and keeping everybody laughing about the inevitable tangled legs and bumping elbows.
Bring lots of fluids and make sure you have a big bed or other comfortable space. The kind of area you can have a quickie on/in (say, a carpeted floor) simply won't do, because you will end up tired and sore and cranky and be giving bad sex to one or more other people."

3. Angel, 33

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"When my hubby and I first considered the idea we overthought it way too much. Planning which nights we were going to try and land someone and it never happened. When it finally happened, it was spontaneous. It just felt right. So, I guess, don't take it all so seriously. If three people are feeling each other, allow the couple to invite the third over and see what happens. But don't force it. From the perspective of the third, I would say make sure both persons in the relationship are equally into you. If one seems distant (cold, NOT shy) and the other one is hard up…..RUN!"

4. c0g, 44

"Set aside gender, and just look at it like this: whomever had the idea for a threesome in the first place should offer for their partner to choose who to invite to join them. This may help with confidence for a first timer. Kind of the same principal as if you cut the cake: someone else should pick the first piece. More experienced play partners will use other methods of selecting additional partners, but its not bad advice for noobs."

5. Laurence, 31

"Planning can be good. Think of how hard it can be just to get two people together. Each extra person makes it exponentially more difficult to find a time to play. As said, make sure everyone is giving their “Fuck yeah!” to the occasion and finds each other attractive.
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If you are worried about feeling left out, or not sure what do to, consider simply taking turns performing certain actions on each person. I think most are creative enough, but simple ideas are: having fun chaining people in different ways, having two ladies riding one gentleman, or two gentleman on different ends of a lady. Also, don't think everyone has to be on a bed the whole time - standing at the edge/foot of a bed opens other opportunities."

6. R.d., 32

"Cardio... And don't forget to stay hydrated."

7. Wry, 31

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"Keep reminding yourself how much everyone wants to be there. It's not luck. It's a fantasy come true for everyone. (You can find more sex advice from Wry here.)"

8. Kisser of Sinners, 36

"I can't count the number of threesomes and group encounters I’ve had. I got good at making sure whenever someone started getting ignored I made a conscious effort to give them attention. This works for larger groups as well. For larger groups having a box of gloves on hand (Badumbum) helps keep hands clean and frees you of trying to track; just accept lots of gloves being used.

Don't always expect lots of actual intercourse. It's sometimes make outs and hand sex. Sometimes it's awesome to have it be a special requested all-on-me birthday request, but that's the only time I've planned a thing in advanced or not made an effort to keep play equal."

9. Chris, 51

"Get tested, share test results. Talk about assumptions and expectations of the threesome. If it's FMF then you get one “pop” per scene as a general rule, make sure the FF team has a way to figure out who gets it, how and when. Not everyone is bisexual, so one of the three if you're doing FMF or MFM will get a lot more attention and do a lot more work. Learn how to lead (like in dancing) and learn how to pass the lead to one another. Depending on body shapes and flexibility, DP ranges from awesome to hysterically funny, be ok with however that works out. Oral sex is wonderful, discuss STI's before doing/receiving it.
The most important tip for me is to make sure that no one is intoxicated in any way. Threesomes without intoxication (at least the first few) are way better than intoxicated threesomes. Save the intoxication for when you know each other's bodies, and are used to (and can anticipate) your partners' reactions. Be playful, instigate. If you're the M in the FMF, don't push for your orgasm. Keep giving to the FF pair until they can't take it any more. Part of the fun is the tension around the M orgasm, so play with it."

10. Anthony

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"Communication before during and after. I can’t stress that enough. No matter how much you talk about it, you will have to talk about it again. It’s about trust, having fun, and making sure everyone is getting their needs met. Be willing to be open during the sex and — just like when tying someone with rope — don't forget its not about the rope or the sex; it’s about the people. Also, it’s important to not be selfish. If everyone is committed to ensuring everyone involves gets their desires fulfilled, it will make for an amazing time, time after time!"

11. S, 39

It's easier if: All participants are bi/queer'ish, all parties like to watch and be watched, intercourse is not the end goal, agree on the level of intoxication, don't have problems with show stopping jealousy, everyone can pay attention to each other, partners that are comfortable pushing but not exceeding boundaries, find people open to spontaneous encounters in advance and have the discussion, Viagra is helpful. If you REALLY want a threesome/group play, try bringing it up on the first/second date. Ignore my advice and others and try to find your own voice to discuss this with partners.

Images: 雷米 杜Flickr; Giphy (7)