Adding to the Conversation: Your First Threesome by Dan and Jennifer
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As a swinger, the title of the video, “Your First Threesome: Who Should It Be With?,” created by Dan and Jennifer, caught my eye when it was mentioned on Twitter. I couldn’t wait to see it. And now, I can’t wait to comment on it.
The video was created based on a question submitted by a woman. Something to the effect of: My boyfriend and I decided to participate in a threesome. Who should it be? Should it be a close friend who’s comfortable with the idea or should it be a stranger, but a clean stranger of course?
I agree with one statement: It’s a bad idea to have a threesome with a complete stranger. That’s where my agreement ends. And my concern begins. A concern that caused me to tell Tank about what I heard.
“They said it’s probably not a good idea to have a threesome with a close friend who’s comfortable with the idea. They made it sound so black-and-white.”
“Really?”
“Yes. Wasn’t your first threesome with two girlfriends who knew each other?
“Yes. And when I was married, my wife and I had a threesome with a close friend of hers that I dated in the past.”
“My point exactly. I’m not seeing the problem in having a first threesome with a person you know and trust. Someone who’s comfortable with the idea.”
“What am I missing here?’
“Well. There’s one question everyone needs to answer. And that’s ‘why.’ Once you agree on the ‘why’ with your partner——the rest doesn’t matter.” The answers to who what, when where, and how easily fall into place.”
“You’re right. It does.”
My answer to the option of inviting a friend to join in would have been “it depends.” It depends on why you want the threesome in the first place. And sometimes, inviting a trusted friend who has similar motivations to you is the perfect choice.
Unfortunately, Dan and Jennifer also miss this critical conversation in their follow-up video called “5 Tips to Make Your First Threesome More Successful.”
They go on to say that a first threesome should be held with a third person who is experienced—what they call sexually social. While I agree that experience is very helpful, based on what I’ve seen and experienced, it really helps to make the situation lighthearted and enjoyable. This is NOT a test of sexual prowess or skill. Because, at the core, swinging isn’t about the sex—it’s about enhancing the relationship a couple has by adding a variety of amazing intimate experiences to it.
I’m also not fond of their online site recommendations to find a third person for a threesome. SDC tends to be for the “beautiful” people—at least in my community—which has more than a million of people living in it. AFF (Adult Friend Finder) members don’t all necessarily understand or embrace the mindset of swinging (as compared to wife swapping behavior). And Kasidie includes other sorts of fetishes like BDSM, kink, and the like—which may be too much for first-timers.
The reason I prefer Swing Lifestyle is that people of all looks, sizes, and ethnicities are members. (Disclosure: I do not sell memberships on behalf of the organization.) Many are professionals in their communities. People you interface with every single day. And most understand the mindset and rules behind swinging. One of which Dan and Jennifer also neglected to mention in their 5 Tips video: No means no. Period. End of story.
I’ll stop here. If you have the chance to watch one or both of the videos, please feel free to add to the conversation. I’d love to hear your comments.







