How To Have a Threeway For The First Time in 2019

people having a theeway

If like many others you've been fantasizing about how to have a threeway and make it reality, this guide will help.

After more than 20 hours of research and reviewing hundreds of other people tips this guide condenses the best threesome tips in one place. Whether it's lesbian threesome or MMF (male, male, female) - we've got you covered.

Me and my partner recently went through our own first threesome experience — FFM and can share the experience… Enjoy:


girlfriend having her first threesome

The Biggest Challenges With Making Threesome Reality

If you're swinger friendly and have done it already it may easy for you…

But for most of us — anything involving more than one person is challenging.

There is tons of emotional baggage you'll need to face:

  • jealousy
  • insecurities
  • fear

It's not like trying anal for the first time. Done badly it can mess up the relationship…

So if you're looking for variety in relationships you may try something simpler first like:

  • anal sex
  • double penetration with dildo or butt plug
  • just adding new sex toys, bondage play, impact play
  • or even buying your own cheap sex dolls —did you know you could buy a shemale sex doll (with anal hole and penis) and use that as a fake threesome and double penetration? 🙂

My point is: if you're completely new to any kind of kinky play… maybe you should simply explore different holes, different toys…new positions, new roleplays and that can provide enough excitement…!

wife preparing for first threesome

5 Tips for Preparing For Your First Threesome

I'll focus here on the perspective from couples side as I believe the most work of communication is done between couple first…

Then the third person.

But either way: a clear communication upfront is key.

And it comes without saying: make sure you stay safe, ensure the third person is clean from STI's and use protection.

Let's get to it:

#1–Make Sure You Both Want A Threesome

If one of the partners is kinda tricked into agreeing on having a threesome, there is a lot more room for error to happen.

You must talk with each other, discuss the jealousy, discuss the ego and what you are looking for in threesome.

In some relationships, one partner will look at it as cheating and the insecurities will rise above the fold.

That's definitely a red flag.

You both must want it.

woman worrying about threesome

#2 — Discuss About Potential Red Flags & Insecurities

Talk in detail how you would want it to happen.

For example, my girlfriend in social dancing was often jealous on other girls… I knew this was going to be an issue.

But still through communication we talked how to make sure she doesn't get jealous, how it should look like — and with me respecting her needs, we'll fixed it.

In her case, it was simply me introducing her with some girls that she felt insecure about. Once she knew them, she was all good.

The same thing is about discussing threesome. You surely can foresee some potential red flags and prepare the plan to deal with them upfront.

lesbians having threesome on mountaintop

#3 — Understand Why You Want Threesome & What You Want To Get Out Of It

It actually is very important to have this talk for all three sides (unless of course you're choosing an escort).

For something like that to happen all sides should be satisfied and clear upfront what they are getting out of it to have enough motivation to go for the trouble of preparation.

It's important that your partner doesn't get insecure and knows that this kink isn't about any trouble that you have in the bedroom.

Best if your sexual life is perfect without a threesome. Otherwise she or he will easily get insecure when seeing you enjoying the third partner too much.

two woman holding hands

#4 — How To Find A Threesome Partner?

There are three ways:

  • pay for an escort — find someone you both like, rent a room in hotel, explain what you want and make it happen. Pretty straight forward and safe.
  • look online for person you don't know — Tinder, Craigslist, Reddit, Fetlife, AdultFriendFinder, OkCupid are all good sides for that. Or find the local one where the swinger type lifestyle or kink/fetish lifestyle is embraced
  • ask a friend you know to join — This is the path we took. It can be both the easiest, but also the most dangerous way, because you can mess up friendships. In our case, we had a very good communication with another girl, who was open…which opened a natural opportunity.

The safest way is to find a professional and then you can just put it down like a list of wishes… But it's also the most expensive.

With people you don't know or a friend you know — you must carefully discuss all sides.

What the third person wants to get out of the threesome?

All of these things must be discussed upfront, taken slow to avoid any bursts of insecurity or jealousy happening during the actual threesome.

hot threesome ready for action

#5 — How To Act During The Threesome?

Expect the performance anxiety to happen — it's a new thing you're doing.

Expect feelings to come up — jealousy, insecurities, excitement.

Take it slow at first — talk it through, drink a glass of wine (but don't get drunk).

Start with kissing, ask before doing something.

Check in with each other to see if everyone is okay. Simple eye-contact will do (agree on it beforehand).

Don't get carried away — going primal probably isn't the best idea.

It's kinda like having sex for the first time…You are exploring something completely new.

Talk beforehand what you gonna do after the act itself?

What the third person will do? Will you hang out afterwards?

I suggest you take the first time super slow, maybe even not having intercourse, if it's a stretch.

If you’re doing it the first time better if the third partner doesn’t stay overnight. It might get awkward and might leave a sour aftertaste.

You're learning about completely new type of relationships. Don't do something you might regret later.

Baby steps will pay off for a more exciting time next time…!

Watch this video by Lena The Plug on all three people explain the threesome experience from their perspective (not so serious).

Very helpful if you get past the sexiness:

woman sharing her surprise threesome story

Other People Best Tips & Stories On Having A Successful Threesome Experience

Here's some perspective from other people:

“Having a threesome is not like trying anal. “

“If you try anal sex and don’t like it, chances are pretty good it’s not going to leave a lasting scar on your relationship.

A threesome that you aren’t both ready for can do just that.

And besides, she could have told you ‘no’ when you wanted to try anal.

I’m in a poly relationship, and before that I was in an open relationship.

I have threesomes on a somewhat regular basis.

They are great, but they are not for everyone.

My girlfriend, boyfriend, and I can enjoy threesome together because we are all on the same page about it.

Each of us wants to be in this kind of relationship, and none of us were pressured or coerced into it.

We also had a very realistic understanding of what we were getting ourselves into, and we maintain good communication when issues or jealousy come up.

We were prepared for the consequences of having threesomes.

If you feel like it’s cheating, then your relationship isn’t prepared for it.
If you feel like it’s cheating then you aren’t prepared for it, which is totally okay.
And if she has to push you, then she definitely isn’t prepared for it.

If she cannot respect your boundaries, then your relationship probably isn’t strong enough to survive the potential fallout of jealousy and insecurity that tends to come from opening up a relationship when everyone involved isn’t ready for it.

It’s totally okay that you don’t want to have a threesome.

Some people are naturally 100% monogamous and there is nothing wrong with that.

It is not okay for her to push you into something like this if you don’t want it.”

Source: Sarilia

couple kissing each other at car

“If both partners in couple aren't ready for threesome — compromise.”

“I wanted to try a threesome, and he was very not into that. We compromised by buying a dildo.

Granted, that dildo can’t do all of the things having a second person around can do, but man, it is fun to be able to play with two cocks, even if one of them is made of silicone.

It has let me experience some of the things I’d wanted to try, like double penetration, and let him continue to be the only man in our bedroom.”

Source: bitemarkedbuttplug

“Advice for a woman being the third person of threesome with married couple.”

“I’m the wife half of a couple that really enjoys threesomes.

I would think it was hot as hell if the woman admitted to me that she’s a little nervous or wants to be taught/directed.

It would also put me, as the wife in the situation, a bit more at ease because your approach is very nonthreatening.

I’ve been in threesomes where the other woman is clearly trying to prove she’s better than me at pleasing my husband, and that competitiveness is such a turn off for me.

Even if she has skills I don’t have, I’m still home-base pussy, and I don’t like that being threatened.

Everyone can please everyone without it being a competition.

I’d definitely level with them how you’re feeling, or even just ask what some of the scenarios they envision are so you know what you’re getting yourself into.”

Source: RedInkRiot

woman contemplating the bbw threesome

All three people matter in a threesome

“Where I’m coming from: I’m a woman who has had multiple threesomes with a male partner I love and other women, and multiple threesomes where I joined an established couple.

I have not yet fucked multiple men at once… but believe me, I want to.

The couples I have joined have all been fantastic and wanted me to have a good time, and I always have.

I am continually dispirited by threesome advice that acts like all the communication that needs to happen is between the established couple, if there is one.

Yes, a threesome is potentially rocky emotional territory for a couple, and people should protect their relationships.

As the third party, I also don’t want to have sex that someone is going to end up regretting, and I’m trusting them to have had enough private discussion between themselves to try to prevent that eventuality.

But you know what?

It doesn’t sit right with me to see post after post about “set rules with your wife,” with no acknowledgement that the third party also has both limits and desires that need to be part of the negotiation as well.

Here’s one example:

People often throw out rules like no kissing or no penetration between a man and the third.

That’s great if it works for them, and of course they have every right to set whatever boundaries they want to have, but I would never agree to have sex with a couple that approached me like that.

Partly because it wouldn’t be enjoyable sex to me (I think kissing is half the point of sex!), and partly because if they took the peremptory tone with me that appears in many of these posts …

If I felt like I was being handed a list of rules instead of having a mutual conversation about what everyone wanted and didn’t want — I would not trust them enough to have sex with them.

It’s not that people shouldn’t set the boundaries they need to; of course they should.

But please treat all your sex partners, including women who join you for a threesome, as human beings and equal participants, not just a stand-in occupying the hole in your fantasy.”

Source: wren_in_the_machine

lesbians scissoring in missionary position

Man Sharing His First MFF Threesome Story

Hey guys. I just had my very first threesome (mff. I am the male).

Thought I’d share how it went for those who are interested.

The Quick Version: it was awesome!! Way better than what I thought it would be. Even though I was nervous, they both made sure to have me relaxed and they made it great.

Ok, the details.

I have been casually seeing the first girl for about 2 months.

It is a FwB relationship. She is bisexual.

I told her I have always fantasized about a threesome, and she mentioned a friend of hers is also bisexual and she would love to bring her over some time.

Yesterday, she did.

They have had threesomes together with other guys, so they were way more experienced than me.

I was quite nervous.

Specially it was my first time to meet the new girl.

I didn’t know if my friend would get jealous, and I was worried about paying too much attention to the new girl.

I didn’t know where I was supposed to come… etc.

I told them both it was my first time ever doing this and I had no clue what to do basically.

They both laughed and told me I was in good hands.

They started by both kissing me at the same time which honestly turned my knees into jelly and I fell into the bed.

They both got on top of me and continued kissing me and each other.

Things got hot and heavy from there on.

We did lots of different things.

I started by giving oral to the new girl, then to my friend.

Then they both gave me oral at the same time (hot!).

I gave oral to one while the other gave me oral, gave oral to one while the other was riding me… etc etc.

It was really really great.

The best part was not the sex part, but the part afterwards.
I got to cuddle with two beautiful girls at the same time.

I like how when girls are talking, the dynamics are very different from how men are talking.

They both talk at the same time, interrupt each other, don’t wait for each other to finish sentences… etc.

The energy level is just way higher.

I was there in bed cuddling with both of them, and they were both talking at the same time, telling me stories, laughing, interrupting each other… etc.

One girl would be talking to me, while the other is adjusting to cuddle closer.

One girl would cuddle closer while the other touched me all over.

This was heaven! I couldn’t help but keep thinking how lucky I was.

Definitely one of the best days of my life lol.”

Source: throwaway_sss

sex woman with round sunglasses

“I’ve been in threesomes with two couples, both of which were awesome experiences.”

“Even though the first couple was only looking for a one-time thing, they still treated me as a person joining them for a night rather than as a disposable toy.

We talked about our fantasies and what we wanted out of the experience ahead of time, and we took turns focusing on each other during the act itself.

There were no issues with jealousy or miscommunication and we even hung out fairly regularly for a while afterwards, which made me feel valued even though we only had sex once.

It was a very good experience overall and opened me up to potentially having more threesomes in the future.

The second couple wanted a regular FWB to be actual-friends with outside the bedroom, which really appealed to me.

We also discussed what we wanted out of the experience and what we things wanted to experiment with, and checked in with each other regularly as the FWB relationship progressed.

This was two years ago and we’re now a poly triad, so I guess it worked out :P”

Source: MountainDew_Me

two lesbians kissing and scissoring

Bringing It All Together

That's it…!

Tons of stories, tons of tips, tons of advice…!

Final words…?

It really helps if you put yourself in their positions either before or during the whole threesome act.

Think how other person would feel if you do this and that…?

It helped tons for me and can help a lot for you to avoid any jealousy even coming up…

Hope this was helpful…

Enjoy and stay safe! 🍷

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