Sex in Odd Numbers: Is a Three-way the Way to Go For You?

Mike Szymanski
5 min readOct 14, 2021

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By Mickey Skee

Having a third person enter a relationship can be a challenge.

Everyone thinks that the ideal relationship for a couple to be in a triad: me, my partner and a plaything. The reality is, that it’s practically impossible to sustain longterm.

I recently had three close friends give it a try. Two guys who were in a long-term committed monogamous relationship, one bisexual, decided to let a guy move in with them.

They slept in the same bed, they spent all their free time together, they ate, shopped and played together. It was a disaster from the outset.

I’ve heard the explanations from all sides, and thankfully all three remain quite close friends. But, although they’re all very expressive people, and they’re all well-liked, they weren’t very good at communicating among themselves. In fact, they all seem to have their own ideas about what went wrong.

The trouble is, when a third party enters an already existing relationship, that person is very literally the odd-man out. In this case, the new guest really didn’t have a chance to make himself an equal leg of this tripod because the guys had a six-year history between them before the third entered into it.

So, if he wanted to spend more time with them, or one of them, the guys naturally saw this as an intrusion that they weren’t used to having. And, when he moved in, this intrusion wasn’t something that they could easily get away from, and they couldn’t send her home.

The other big problem, in this particular case, was how exactly their relationship would be defined once the third moved in. One of the guys thought it would be simply a “fuck-buddy” relationship, the other guy was taking a “wait and see” attitude about how it all would develop, but the newcomer was hoping that he would have “equal footing” in the triad.

Now, as hip, cool and even masculine as this newcomer was, I don’t think he was ready to be just a fuck buddy. And, as much as a slut as he thought he was, he really wasn’t good at being fuck buddies, or understanding what it truly meant.

The newcomer wanted to have a relationship, too. He needed to be nurtured, cajoled and pampered during sex. That’s why he no longer went off to bathhouses to seek anonymous sex as much anymore.

So, I don’t think any guy likes the idea of sitting in his own room like a concubine, ready to be called by the other guys to their room when they’re in the mood. Nah, it’s not going to work.

My own foray into a stable triad arrangement kind of materialized simultaneously, rather than one person intruding on another’s relationship. I was dating a guy, and he was also casually dating another guy. His date started showing interest in me, too, and we all began dating each other.

At first, it got on my nerves that they were dating, too, but part of me fantasized about my perfect threesome.

He defined himself as bisexual, and had a recent relationship with a woman. We both dated a guy who considered himself as solely gay, but had sex with women in his past. I’m bisexual, leaning on the gay side. So we had a bit of that in common.

We worked out a system. He and I went out on Fridays. The two guys went out on Saturdays. The third guy and I hit the gay bars on Sundays. The rest of the week we shared.

We went to movies together, we camped together, we took trips together, we even worked together. It was doomed from the outset.

There was one moment when we all were rather tipsy after a party and we were rolling around on a bed together that it looked like something more may happen.

“I just realized I know what both of your dicks look like,” one of the guys said.

We all looked at each other, and I laughed, “Oh really? Who’s bigger?”

We launched into a very candid description about what we knew each liked in bed. One squeaks during orgasms, he sticks his cold feet in crotches, I squeeze my arms too tight around torsos during sex. It seemed like a natural way to lead to a three-way.

In fact, that talk led to our break-up. Neither of them could ever see the three of us together, even for a single sexual romp. One guy was sensitive about giving bad blow jobs because he had a poor gag reflex. The other didn’t want to get fucked by me.

And I just dreamed of being in the middle of them both. My insistence, my urging, my pushing for that, ended up pushing them both toward each other, and I found myself pushed out of the trio. They didn’t last, of course. One married a guy, the other is a perpetual loner gay. I found a bi boyfriend.

Now, all that being said, there are examples of very successful triads. A few long-term couples I know are able to juggle a third and even have children together. They’re all equal with parenting, with sex and with love.

That’s not to say they haven’t had their share of troubles and jealousies. But, it’s a kind of relationship that we may all aspire to have, whether it’s in odd or even numbers.

But one of the guys in that successful triad summarizes his success in the relationship with one simple word: Communication.

“Talk things out, get your feelings out, communicate,” he says.

It seems like simple advice, but it takes practice. And, if you can’t do it with one partner, how can you possibly do it with two?

This is part of a series of mini-paperback books and Kindle mini-books as part of the Mickey Skee Hardcore Diaries. Check out these books:

Contemplating My Penis & Other Short, But Hard, Diary Entries of a Porn Reporter: More of the Hollywood Hardcore Diaries https://www.amazon.com/dp/B085RSFLND

Cum Chronicles:: Deposits at a Sperm Bank, The White Stuff & The Money Shot https://www.amazon.com/dp/B0863QDG2B/ref=cm_sw_r_tw_dp_U_x_bJHKEbTCMMSRY

3 is Never a Crowd:: Gay Triads with Daddies, Twins, Twinks & Negotiating a Threesome https://www.amazon.com/dp/B086G4JQB5/ref=cm_sw_r_tw_dp_U_x_uHHKEbJ8WWP2A

Secret Same-Sex Liaisons With Celebrities: First-Hand Accounts of a Porn Reporter https://www.amazon.com/dp/B086PNZDS4/ref=cm_sw_r_tw_dp_U_x_AFHKEbVECG7D

Global Gay Sexploits: Kinky Memories of Amsterdam, Borneo, Ibiza & More https://www.amazon.com/dp/B086Y4ZS71/ref=cm_sw_r_tw_dp_U_x_wDHKEbGAZRZW8

Seducing A Straight Man: Best Tips, Hints & Twists on Boffing a Breeder https://www.amazon.com/dp/B0872ZKKK9

check them out!

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Mike Szymanski
Mike Szymanski

Written by Mike Szymanski

Journalist, writer, activist and bisexual, living with Multiple Sclerosis and Dachshunds in Hollywood.

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