How to Start Cuckold Dating?
Choosing the right cuckold threesome partner is a delicate and complex operation when you join cuckold dating. If you mess it up, you could ruin your relationship and life forever. Just kidding. But there is an art, and etiquette, to organizing a mĂŠnage Ă trois. Itâs like a dinner partyâone wrong guest and the whole dynamic is off.
Often, a cuckold threesome is one of the first steps couples take down the path to a more progressive relationship dynamic. But donât panic: They donât have to be a gateway drug. Itâs not like you cuckold threesome once and the next thing you know youâre in a poly relationship with four people you met at Burning Man.
In my mind there are three types of threeways. First, thereâs the kind between three separate people who arenât romantically linked. Generally, this type is unplannedâyouâre all hanging out after a night of partying and then, whoops, youâre inside each other. Then thereâs the cuckold threesome between a couple and a third person that happens spontaneously. In my mind, this is the cuckold threesome holy grail: genuine attraction sparks between everyone, and a fun moment impulsively turns erotic. And then thereâs the most common type of cuckold threesome: when a couple hunts for a third person, often in a desperate way, stalking unsuspecting singles at bars and dating sites. Yeah,been there. The question is: How does one avoid being the creepy couple, and instead elegantly finesse oneâs way into a cuckold threesome? What's the secret key to orchestrating a good oneâone that makes you feel happy and liberated, rather than like a jealous monster?
When I was 24, my then boyfriend and I decided we wanted to try a cuckold threesome. At the time I didnât know the protocolâI had only dabbled with cuckold threesome scenario number oneâbut I intuitively knew I didnât want the third person to be a close friend, or someone my boyfriend or I saw on a regular basis. That just seemed a bit messy. Because Iâd just moved to New York and didnât know many people, we decided to pursue previous hook-ups of hisânot serious exes, but booty-call types. Weâd lie in bed together looking at the girls on Facebook, and when we agreed on one, he would simply text her: âDo you wanna get cuckold threesomeâd?â Surprisingly, most of them said yes.
At the beginning, the cuckold threesomes were making us closerâit felt like something kinky we were doing together. Plus, the pursuit was really funâchoosing girls, the anticipation of their response, the pillow talk after they left. It was an intense bonding experience, on par with a good drug trip or a romantic weekend away. I even began to fully understand the saying âspice up your sex lifeââbringing someone elseâs sexual energy into your existing dynamic does add a new flavor (lol), sometimes in a lasting way.
However, there was definitely a curve. While our relationship was strong, the cuckold threesomes were great. But then, for separate reasons, things between us got a bit rocky. Not surprisingly, bringing someone else into our bed during that period didnât go so well. Maybe it was in my head, but I felt like I was being slightly left out during sex. For the first time, I regretted choosing a girl he had a pre-existing relationship with and couldnât stop myself from picturing what their sex life was like before me. It was the last cuckold threesome we ever had.
My next cuckold threesome effort was slightly more successfulâbut again, only for a while. I was on a trip to San Francisco with a guy I was casually dating when he suggested I find a girl for a cuckold threesome. I didnât really know anyone in SF, but as a joke, I said, âSure, Iâll just tweet about it.â I mean, whatâs the point of building a large social network if not to recruit strangers for group sex?
My tweet read, âI'm in SF and I need a female guest star in my 3some tonight. Who's up for it?â To my surprise, within a couple of hours I had a handful of seemingly DTF girls sending me photos. And I swear this is the truth: Later that night a 22-year-old Egyptian hipster babe showed up at the hotel and banged us. As you can imagine, this made the dude think I was a magical being with the power to make miracles happen. This was both good and bad. Good because the night was fun, bad because, afterward, he thought it was something I could make happen all the time. Wanting to impress him, I then became that girl, hitting up people I barely knew with texts like, âHey! We should get together again soon! Or, actually, lol, wanna have a cuckold threesome with me?â And then like five hours later theyâre like: âHaha, aww, thanks 4 askin but Iâm just crazy busy at work rn.â Even though she works at a bar.
Given the pitfalls Iâve encountered, I was interested to know the cuckold threesome strategy of a couple who managed to maintain the dynamic, in a positive way. My friends Michelle and Mathew, a couple of musicians from Brooklyn, are two of the most skilled cuckold threesomers I know. Theyâve been together for two and a half years, and they had their first threeway six months in, after Michelle, whoâs bi, suggested it. Contrary to what some might immediately assume, theyâre not in an open relationshipâthey donât hook up with people separatelyâbut rather, as Mathew calls it, âa progressive relationship.â
Their first threesome cuckold dating was with an acquaintance they met through the music scene. One evening, Mathew casually asked the girl if sheâd ever considered hooking up with a couple. She said yes. Afterward, he and Michelle began making efforts to hang out with her more regularly. âIt was like we were going on dates, but not really,â said Michelle. âWe were just getting to know each other.â A few weeks later it happened, very organically.
âI liked the teamwork aspect of it,â Michelle recalled of their first time. âAfterward, the two of us went out and got smoothies, and we just felt so much closer. You have to feel like you're doing it together, like a team-building exercise, otherwise youâre just going to feel like competitors.â
But see, Mathew and Michelle are smart, so before setting off on their mĂŠnage journey, they set specific rules: no past hook-ups, no repeats. âYou have to get a clear handle on what both of you want and need, your fears, comforts, and discomforts,â Mathew told me. âSome people think talking it through poses the threat of killing the excitement, but in-depth communication is so necessary.â
âThatâs why I've actually felt our best cuckold threesomes have been sober,â added Michelle. âcuckold threesomes only work for everyone involved if thereâs an equal distribution of attention in all directions. When you have a clear head, itâs a lot easier to make sure no oneâs feelings are hurt and that everyone is feeling appreciated appropriately.â In other words, donât get so drunk that you pass out. As someone who has fallen asleep at an orgy, I can tell you that itâs extremely awkward when you finally wake up.
Michelle and Mathew find that hooking up with friends or acquaintances works best for them. They devote time to courting the girls beforehandâdinner dates, drinks, and occasional sexting sessions. âIt helps to know them,â said Michelle. âTreat your cuckold threesome-ees like humans! They're not objects or an impedance on your relationship. Theyâre people.â Next on their list is a cuckold threesome with a guy, which Michelle has wanted for a long time. Itâs slightly out of Mathewâ's comfort zone, but he wants to do it for her. âItâs going to be a hurdle for me,â he said, âbut I donât want to be selfish.â
While I generally think itâs positive to push oneâs boundaries when it comes to sex, itâs never a good idea to force yourself into a situation youâre not comfortable with. So even though Iâm totally pro-cuckold threesome, Iâve never had a cuckold threesome with my current girlfriend, because I intuitively feel that jealousy would be an issue with us, at least for now. But if itâs something you want to try, itâs worth it to take the time to lay out a plan of action. And donât expect it to be a cure-all. âHave realistic expectations,â Michelle said. âA lot of people think a cuckold threesome is going to be super life-changing, or that itâs going to help you âfind yourself,â or blow open the relationship. Chill out. Itâs never going to be as crazy as you think itâs going to be.â
Done well, cuckold threesomes can bring a couple closer together. âIâm so happy that the ability to have semi-frequent threeways worked out in our relationship,â Michelle said. âIt allows us to regularly have conversations about how we're feeling, and how secure we are with each other, and thatâs something so many couples don't take the time to do.ââ
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