7. Tell
All men are different, and some guys can get by with simply saying “I do threesomes” or “We’re going to take this guy home. You don’t have to participate, but it would be cool if you did.” Not a question, not even a suggestion - a simply stating of a fact.
I like guys who know what they want and state it outright, but I think there is significant risk in a relationship context with simply telling your boyfriend that you’re going to have a threesome and hook up with a third.
But some guys - typically the ones who are more dominant in bed and who may date guys who enjoy handing over control of what happens in the bedroom - get by with doing so. I must caution that if you simply tell, not ask, he might not be into the idea or into the guy - and he may leave. This is the singular most important fact for anyone and everyone to remember in the dating world: You are always free to go; no one has to stay.
All men are different, and some guys can get by with simply saying “I do threesomes” or “We’re going to take this guy home. You don’t have to participate, but it would be cool if you did.” Not a question, not even a suggestion - a simply stating of a fact.
I like guys who know what they want and state it outright, but I think there is significant risk in a relationship context with simply telling your boyfriend that you’re going to have a threesome and hook up with a third.
But some guys - typically the ones who are more dominant in bed and who may date guys who enjoy handing over control of what happens in the bedroom - get by with doing so. I must caution that if you simply tell, not ask, he might not be into the idea or into the guy - and he may leave. This is the singular most important fact for anyone and everyone to remember in the dating world: You are always free to go; no one has to stay.
8. “Jason, one of my old f.u.c.k buddies, told me he thinks you’re hot.”
Be careful when choosing a third from your list of previous playmates.
I know many couples whose third-party playmates are previous fuck buddies and even previous boyfriends. I applaud these couples, because their communication skills must be strong.
As a guy who simply cannot do monogamy, I have found that the most frustrating part of being a couple that plays together are the unavoidable situations when a guy is only interested in one of you and not the other.
When you play with previous BFs or FBs, this problem becomes kind of obvious. Your former playmate is likely to be more into your than your beau. But this problem also can occur with onetime Grindr hookups and guys with whom neither of you have any history.
This aspect of threesomes is something that will come up, so be prepared for it. It will introduce a whole new kind of jealousy and a different kind of tension. You might find yourself suddenly wondering why nobody ever seems to be interested in you and everyone is interested in him, or you might find yourself having to turn down and refuse interested thirds because it is clear he is only interested in you, and you know your boyfriend would be hurt.
While monogamy is totally absurd and unrealistic to me, I will admit that good threesomes are hard to come by. A good threesome is when the guy is interested in both of you equally.
9. “We should meet up with Andre, Brent, and Will. I’m sure they know a lot about threesomes.”
Chances are that if you’re an out gay man living in an out gay man’s world, you know at least one triad, “throuple,” or three-guy relationship. If you’re interested in breaking open your relationship enough for threesomes but are skeptical of anything beyond sex - three-way dating is not something you are interested in - talk with your triad friends.
Plan a dinner date between all five of you with the clear intention (communicated beforehand) of asking your triad buddies how they came together. Many triads - including all the ones I know - started off as couples that met and played with someone and gradually, mutually fell for him.
Ask them about their process of letting third-party playmates in when they were still a two-person couple. Ask questions: How did they navigate the boundary between sex and affection? In the beginning, were threesomes with one-timers OK, but repeat partners a no-go?
Chances are that they will tell you the same thing I’m telling you now: They communicated openly and honestly, expressed their desires, accepted the desires of each other, and went through the process with a vast array of tense moments and surprised moments and happy moments - the moments that make up all relationships.
Enjoying threesomes with your boyfriend does not always lead to a triad relationship - in fact, the vast majority of couples who play together with occasional thirds never go on to have three-way relationships. A triad is a whole different ball game and a far cry from being a couple who occasionally hook up with a third.
10. “I have really strong feelings for you and I am interested in having something with you, but we both play for the same team. So…threesomes?”
Sometimes you fall for a guy who happens to enjoy the same sex role as you do. In the age of Grindr and Scruff, this happens less frequently, since we live in an age when one’s sex role is either clearly displayed on their profile or one of the first things communicated, and for many gay men, this is an automatic deal-breaker.
But sometimes you meet a guy at a bar or on the subway or behind the register of your favorite clothing store that you really click with, and you two get coffee and talk for hours, and you fall for him the way people used to fall for each other. Suddenly you realize that you are scared of asking that fated question - “What are you into?” - because you like him.
Your heart might sink a little when he says he’s interested in the same thing you are, but I must stress that there are few things more valuable in life than friends and people you connect with romantically, so do not immediately discard guys who play for the same team you do. I know a few long-term gay couples who both bend to bottom or top, and their relationships are solid - and nonmonogamous.
The “threesome talk” happens early and automatically for these couples. I have heard several tops say their LTRs with other tops are some of the best they’ve had - they simply hook up with bottom fuck buds whenever they want to get off.
I’ve heard a few bottoms say their relationships with other bottom guys are some of the most romantic and powerful they’ve had. People are more than their sex role - a fact that gay men should remind themselves of more often - and threesomes can be a healthy feature of a stable long-term relationship.
11. “What would you do with another top/bottom?”
That “I’ve always wanted to try DP” line worked because I am a bottom and my boyfriend at the time was a top who got off on using me with another top. Our threesomes consisted of two tops banging one bottom (me).
Other relationships did not work out so well. My most recent ex was also a total top and more dominant than anyone I have dated. But for some reason we could never find another top who wanted to spit-roast me (a dick in the mouth and a dick in the butt) or even a versatile guy who could both fuck me and take a pounding from him.
Every threesome we had was with guys who claimed they were versatile, but when playtime came, I was always lying there twiddling my thumbs while some guy got fucked hard by my boyfriend. The thirds we took home were consistently dissatisfying to me and to our relationship, and eventually became the source of arguments.
The difference between the two? In the first relationship, we knew what we were looking for. My boyfriend knew he wanted to see me get fucked (and I obviously wanted to get fucked) and we communicated this pre-established objective to interested parties.
If you and your boyfriend have become comfortable with the idea of threesomes, discuss with him what what you are ideally looking for. Playing together means you will inevitably be dissatisfied at some point with the guys you take home, but if you are looking for a third to satisfy a certain fantasy or perform a certain sex act, good threesomes might happen more easily because a clear goal is communicated.
12. “Any kinks?”
Threesomes and all forms of group sex can be kinks for some people. Some guys fetishize the idea of three people in the same way others fetishize the presence of very large groups (gang bangs, sex parties) or particular kinky setups and role-play scenarios that require more than two people.
Some interrogation scenes work well with multiple people, and many submissive guys love the idea of being dominated and shared by two dominants (myself included). I know quite a few Sirs who love dominating two subs at the same time. If you’re a kinky couple, threesomes might not seem that outlandish.
Then again, they might. It is one thing to get kinky with your boyfriend. It is another thing to get kinky with your boyfriend and someone else. Jealousy and the boundaries of intimacy still apply here, on top of safe words and aftercare and all the stuff involved in kink play. Navigate with caution and care.
In the early days of your relationship, when you are still figuring each other out and talking about the things that turn you both on, tell him you are interested in threesomes, even if only as an idea that you think is hot, not something you have to do with him immediately or even as a practice that you wan to work up to as a couple. It is enough to simply say “I like threesomes” or even “I like the idea of threesomes” without saying they are something you want to do together, now or ever.
When I am getting to know a guy, I always try to talk about my sexual bucket list, preferably as early on as possible. My sexual bucket list includes some more extreme activities - getting fisted in a Berlin darkroom, hours of anonymous sex at the Saint at Large - and while most things on it I have already done (for me, a desire does not stay unmet for long), I want the guys I like to know that I can want them and want to satisfy these desires synonymously. I want him to know that if he stays with me for the long run, at some point he will either be fulfilling these fantasies with me or waiting in the hotel room.
If threesomes are on your list, tell him. They might be on his list too.
Read with part 1 in here:
Be careful when choosing a third from your list of previous playmates.
I know many couples whose third-party playmates are previous fuck buddies and even previous boyfriends. I applaud these couples, because their communication skills must be strong.
As a guy who simply cannot do monogamy, I have found that the most frustrating part of being a couple that plays together are the unavoidable situations when a guy is only interested in one of you and not the other.
When you play with previous BFs or FBs, this problem becomes kind of obvious. Your former playmate is likely to be more into your than your beau. But this problem also can occur with onetime Grindr hookups and guys with whom neither of you have any history.
This aspect of threesomes is something that will come up, so be prepared for it. It will introduce a whole new kind of jealousy and a different kind of tension. You might find yourself suddenly wondering why nobody ever seems to be interested in you and everyone is interested in him, or you might find yourself having to turn down and refuse interested thirds because it is clear he is only interested in you, and you know your boyfriend would be hurt.
While monogamy is totally absurd and unrealistic to me, I will admit that good threesomes are hard to come by. A good threesome is when the guy is interested in both of you equally.
9. “We should meet up with Andre, Brent, and Will. I’m sure they know a lot about threesomes.”
Chances are that if you’re an out gay man living in an out gay man’s world, you know at least one triad, “throuple,” or three-guy relationship. If you’re interested in breaking open your relationship enough for threesomes but are skeptical of anything beyond sex - three-way dating is not something you are interested in - talk with your triad friends.
Plan a dinner date between all five of you with the clear intention (communicated beforehand) of asking your triad buddies how they came together. Many triads - including all the ones I know - started off as couples that met and played with someone and gradually, mutually fell for him.
Ask them about their process of letting third-party playmates in when they were still a two-person couple. Ask questions: How did they navigate the boundary between sex and affection? In the beginning, were threesomes with one-timers OK, but repeat partners a no-go?
Chances are that they will tell you the same thing I’m telling you now: They communicated openly and honestly, expressed their desires, accepted the desires of each other, and went through the process with a vast array of tense moments and surprised moments and happy moments - the moments that make up all relationships.
Enjoying threesomes with your boyfriend does not always lead to a triad relationship - in fact, the vast majority of couples who play together with occasional thirds never go on to have three-way relationships. A triad is a whole different ball game and a far cry from being a couple who occasionally hook up with a third.
10. “I have really strong feelings for you and I am interested in having something with you, but we both play for the same team. So…threesomes?”
Sometimes you fall for a guy who happens to enjoy the same sex role as you do. In the age of Grindr and Scruff, this happens less frequently, since we live in an age when one’s sex role is either clearly displayed on their profile or one of the first things communicated, and for many gay men, this is an automatic deal-breaker.
But sometimes you meet a guy at a bar or on the subway or behind the register of your favorite clothing store that you really click with, and you two get coffee and talk for hours, and you fall for him the way people used to fall for each other. Suddenly you realize that you are scared of asking that fated question - “What are you into?” - because you like him.
Your heart might sink a little when he says he’s interested in the same thing you are, but I must stress that there are few things more valuable in life than friends and people you connect with romantically, so do not immediately discard guys who play for the same team you do. I know a few long-term gay couples who both bend to bottom or top, and their relationships are solid - and nonmonogamous.
The “threesome talk” happens early and automatically for these couples. I have heard several tops say their LTRs with other tops are some of the best they’ve had - they simply hook up with bottom fuck buds whenever they want to get off.
I’ve heard a few bottoms say their relationships with other bottom guys are some of the most romantic and powerful they’ve had. People are more than their sex role - a fact that gay men should remind themselves of more often - and threesomes can be a healthy feature of a stable long-term relationship.
11. “What would you do with another top/bottom?”
That “I’ve always wanted to try DP” line worked because I am a bottom and my boyfriend at the time was a top who got off on using me with another top. Our threesomes consisted of two tops banging one bottom (me).
Other relationships did not work out so well. My most recent ex was also a total top and more dominant than anyone I have dated. But for some reason we could never find another top who wanted to spit-roast me (a dick in the mouth and a dick in the butt) or even a versatile guy who could both fuck me and take a pounding from him.
Every threesome we had was with guys who claimed they were versatile, but when playtime came, I was always lying there twiddling my thumbs while some guy got fucked hard by my boyfriend. The thirds we took home were consistently dissatisfying to me and to our relationship, and eventually became the source of arguments.
The difference between the two? In the first relationship, we knew what we were looking for. My boyfriend knew he wanted to see me get fucked (and I obviously wanted to get fucked) and we communicated this pre-established objective to interested parties.
If you and your boyfriend have become comfortable with the idea of threesomes, discuss with him what what you are ideally looking for. Playing together means you will inevitably be dissatisfied at some point with the guys you take home, but if you are looking for a third to satisfy a certain fantasy or perform a certain sex act, good threesomes might happen more easily because a clear goal is communicated.
12. “Any kinks?”
Threesomes and all forms of group sex can be kinks for some people. Some guys fetishize the idea of three people in the same way others fetishize the presence of very large groups (gang bangs, sex parties) or particular kinky setups and role-play scenarios that require more than two people.
Some interrogation scenes work well with multiple people, and many submissive guys love the idea of being dominated and shared by two dominants (myself included). I know quite a few Sirs who love dominating two subs at the same time. If you’re a kinky couple, threesomes might not seem that outlandish.
Then again, they might. It is one thing to get kinky with your boyfriend. It is another thing to get kinky with your boyfriend and someone else. Jealousy and the boundaries of intimacy still apply here, on top of safe words and aftercare and all the stuff involved in kink play. Navigate with caution and care.
In the early days of your relationship, when you are still figuring each other out and talking about the things that turn you both on, tell him you are interested in threesomes, even if only as an idea that you think is hot, not something you have to do with him immediately or even as a practice that you wan to work up to as a couple. It is enough to simply say “I like threesomes” or even “I like the idea of threesomes” without saying they are something you want to do together, now or ever.
When I am getting to know a guy, I always try to talk about my sexual bucket list, preferably as early on as possible. My sexual bucket list includes some more extreme activities - getting fisted in a Berlin darkroom, hours of anonymous sex at the Saint at Large - and while most things on it I have already done (for me, a desire does not stay unmet for long), I want the guys I like to know that I can want them and want to satisfy these desires synonymously. I want him to know that if he stays with me for the long run, at some point he will either be fulfilling these fantasies with me or waiting in the hotel room.
If threesomes are on your list, tell him. They might be on his list too.
Read with part 1 in here:
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