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Illustration by Tricia Lim

Threeways: From fantasy to reality

By Lady Marmalade and Ms. Robinson, February 12 2019 —

Threesomes can come in many different forms — two men and a woman, two women and a man, three women, three men — any combination of gender expressions and identities are possible. 

There are plenty of misconceptions surrounding engaging in sex with multiple partners at a time. As a person who’s never had a threesome, I interviewed Ms. Robinson, someone who has participated in several of the above iterations of the activity, to talk about her experiences.

Lady Marmalade: How does one initiate a threesome?

Ms. Robinson: Threesomes are best when they happen organically. Initiating one depends on the relationship of the involved parties. They can happen just the way regular hook-ups happen. Three folks are out at a party or a bar decide to go home together. If you’re a couple looking for a third party, dating websites are popular places to enlist an interested singles looking to join you for the night. The couple can be out in public and just have great chemistry with a third person. 

LM: Speaking of couples engaging in threesome sex, does it work if a pre-existing relationship is involved?

MR:It absolutely can. Plenty of established couples bring in a third party for the evening, or even for a long-term, friends-with-benefits type of situation. 

LM: How do you deal with jealousy in those situations?

MR: Setting boundaries is super important. If you’re the really jealous type, a threesome while you’re in a relationship probably isn’t for you. If you’re a couple
looking to add a third, you really need to think about whether or not the image of your significant other going down on someone else is something you can live with.

LM: What types of boundaries need to be set and how do you go about setting them?

MR: If you aren’t a couple, the same rules apply during threesomes as during one-on-one sexual interactions. Consent is vital and you’ll need to be as vocal about your boundaries as you would be in those one-on-one situations. 

If you’re in a relationship, the two of you should definitely discuss boundaries prior to engaging in a threesome. Are you comfortable with penetrative sex? Is oral off the table? Do partners of the same sex want to spend any time getting intimate with each other or simply focus their attention on the partner of the opposite sex? Also, do you want the person you bring into your bedroom to be someone you know? What are the rules for either of you contacting this person again post-threesome? There’s a lot to discuss.

LM: How do you stay safe during threesome sex?

MR: Health is ultra important during a threesome. Remember that the threesomes you see in pornography are performed by people who have regular STI checks as part of their job. Unless you absolutely know the sexual history of both partners, threesome sex can be risky. Make sure you’re wearing a different condom for each partner — you’ll need a lot of condoms if you plan to swap quite a bit during the interaction. 

LM: What’s your favourite type of threesome and the hottest thing that’s ever happened to you during one?

MR: I enjoy all types of threesomes — that’s the benefit of being bisexual. Two men paying attention to me is amazing, but so is myself and another woman focusing our attentions on another man — or woman. I find that people naturally choose a focal point of the threesome. While it’s generally the odd gender out that gets all of the attention, the best threesomes happen when all partners happily engage with each other. 

As for the hottest thing that’s ever happened to me during one — everything! There’s so much to see and touch and so much variety. If all the partners are comfortable with each other, it’s hard not to enjoy it. For me, the best threesomes happen when I’m in a friends-with-benefits situation with someone and we engage a third for some fun.

I do have one fantasy that’s never been played out during a threesome, but that’s a story for another day…



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