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 mĆ©nage Ć trois. Itās like a dinner partyāone 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 donāt panic: They donāt have to be a gateway drug. Itās not like you cuckold threesome once and the next thing you know youāre in a poly relationship with four people you met at Burning Man.
In my mind there are three types of threeways. First, thereās the kind between three separate people who arenāt romantically linked. Generally, this type is unplannedāyouāre all hanging out after a night of partying and then, whoops, youāre inside each other. Then thereās 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 thereās 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 oneās way into a cuckold threesome? What's the secret key to orchestrating a good oneāone 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 didnāt know the protocolāI had only dabbled with cuckold threesome scenario number oneābut I intuitively knew I didnāt 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 Iād just moved to New York and didnāt know many people, we decided to pursue previous hook-ups of hisānot serious exes, but booty-call types. Weād lie in bed together looking at the girls on Facebook, and when we agreed on one, he would simply text her: āDo you wanna get cuckold threesomeād?ā Surprisingly, most of them said yes.
At the beginning, the cuckold threesomes were making us closerāit felt like something kinky we were doing together. Plus, the pursuit was really funāchoosing 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 āspice up your sex lifeāābringing someone elseās 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 didnāt 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 couldnāt 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 successfulābut 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 didnāt really know anyone in SF, but as a joke, I said, āSure, Iāll just tweet about it.ā I mean, whatās the point of building a large social network if not to recruit strangers for group sex?
My tweet read, āI'm in SF and I need a female guest star in my 3some tonight. Who's up for it?ā 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, āHey! We should get together again soon! Or, actually, lol, wanna have a cuckold threesome with me?ā And then like five hours later theyāre like: āHaha, aww, thanks 4 askin but Iām just crazy busy at work rn.ā Even though she works at a bar.
Given the pitfalls Iāve 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. Theyāve been together for two and a half years, and they had their first threeway six months in, after Michelle, whoās bi, suggested it. Contrary to what some might immediately assume, theyāre not in an open relationshipāthey donāt hook up with people separatelyābut rather, as Mathew calls it, āa progressive relationship.ā
Their first threesome cuckold dating was with an acquaintance they met through the music scene. One evening, Mathew casually asked the girl if sheād ever considered hooking up with a couple. She said yes. Afterward, he and Michelle began making efforts to hang out with her more regularly. āIt was like we were going on dates, but not really,ā said Michelle. āWe were just getting to know each other.ā A few weeks later it happened, very organically.
āI liked the teamwork aspect of it,ā Michelle recalled of their first time. āAfterward, 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 youāre just going to feel like competitors.ā
But see, Mathew and Michelle are smart, so before setting off on their mĆ©nage journey, they set specific rules: no past hook-ups, no repeats. āYou have to get a clear handle on what both of you want and need, your fears, comforts, and discomforts,ā Mathew told me. āSome people think talking it through poses the threat of killing the excitement, but in-depth communication is so necessary.ā
āThatās why I've actually felt our best cuckold threesomes have been sober,ā added Michelle. ācuckold threesomes only work for everyone involved if thereās an equal distribution of attention in all directions. When you have a clear head, itās a lot easier to make sure no oneās feelings are hurt and that everyone is feeling appreciated appropriately.ā In other words, donāt get so drunk that you pass out. As someone who has fallen asleep at an orgy, I can tell you that itās 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 beforehandādinner dates, drinks, and occasional sexting sessions. āIt helps to know them,ā said Michelle. āTreat your cuckold threesome-ees like humans! They're not objects or an impedance on your relationship. Theyāre people.ā Next on their list is a cuckold threesome with a guy, which Michelle has wanted for a long time. Itās slightly out of Mathewā's comfort zone, but he wants to do it for her. āItās going to be a hurdle for me,ā he said, ābut I donāt want to be selfish.ā
While I generally think itās positive to push oneās boundaries when it comes to sex, itās never a good idea to force yourself into a situation youāre not comfortable with. So even though Iām totally pro-cuckold threesome, Iāve 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 itās something you want to try, itās worth it to take the time to lay out a plan of action. And donāt expect it to be a cure-all. āHave realistic expectations,ā Michelle said. āA lot of people think a cuckold threesome is going to be super life-changing, or that itās going to help you āfind yourself,ā or blow open the relationship. Chill out. Itās never going to be as crazy as you think itās going to be.ā
Done well, cuckold threesomes can bring a couple closer together. āIām so happy that the ability to have semi-frequent threeways worked out in our relationship,ā Michelle said. āIt allows us to regularly have conversations about how we're feeling, and how secure we are with each other, and thatās something so many couples don't take the time to do.āā
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