In this episode…
My personal story of the first time I had an amazing threesome with two women (FFM)
How you can have an amazing threesome too (or at least increase your chances)
How to avoid bad threesomes (hurt feelings and trauma etc…)
Conversation and sex techniques to actually begin your threesome in a good way
My First Threesome Experience (The Truth)…
To be honest, the first time I had a threesome was awkward, and it wasn’t that great. My second threesome was mostly fun, but the next day was weird… The next bunch of threesomes I had were pretty negative, with lots of hurt feelings and challenging relationship dynamics.
The main story on this page is about the first time I had an amazing threesome (that I initiated with two women, AFTER learning from all the mistakes of my earlier threesomes mentioned above).
On this page you’ll find the main story, and then some other threesome stories + threesome advice below.
In the main story, you’ll see that real life is VERY different from porn, and even still, it is 100% possible for you to have an incredibly hot threesome. Especially if you use the techniques described in this story.
The First Time I Had an Amazing MFF Threesome (Episode Video):
My Backstory:
My sex life used to be horrible. I used to struggle with premature ejaculation, erectile dysfunction, porn addiction, and sexual anxiety to the point where I even avoided women because I was afraid of being sexual with them and performing poorly (which is what would happen).
To go even further back, I never had sex in high school. I was an unpopular and underdeveloped stoner geek, who built model rockets, played trumpet in band and ran cross country. Basically the opposite of high school stud material. I fantasized about sex a lot, and was jealous of the guys who had sex and girlfriends.
Through my early 20s and into my late 20s, my sex life was horrible. It wasn’t until my late 20s that I decided I HAD to improve my sex life. Up until that point, threesomes were my biggest long-standing sexual fantasy… and they were something that I thought I would never experience. (And I didn’t until my early 30s).
I share this with you because I want you to know that even if you are currently struggling with sex, and threesomes feel like an impossible pipe dream, IF you put in consistent effort over time, you can experience success and happiness with your sex life too.
If You Want a Threesome, Know This…
Threesomes can be incredible (as you’ll hear in the podcast episode on this page), and if you want to have one, you should put in the effort to figure out how to make one happen in a way that feels good to everyone.
The difference between an amazing threesome and a bad one almost always comes down to the level of skillful communication everyone has before, during and after the threesome.
The reality is that the idea of a threesome is often more fun than what actually happens. A high percentage of people who have threesomes come away from the experience feeling hurt or disappointed (because everyone involved didn’t know how to communicate their desires, fears and boundaries in a skillful way).
If You’re in a Relationship, Be Careful…
Having a threesome with your partner and a guest star can be an amazingly beautiful experience – a great way to go on a new adventure with your partner.
And… The inclusion of an extra partner into your bedroom brings in a LOT more variables than you might think (and they’re not all fun).
For one example, lots of guys fantasize about having a threesome with two women. What happens if during the threesome, the women end up being much more into each other than the guy? What if they focus on each other and forget about the guy? *(This happens more than you might expect, and it can create unexpected feelings of jealousy, anger, fear, loneliness and more in the man…)
For another example, what do you think will happen if you focus more of your attention on the special guest instead of your partner? This isn’t necessarily a bad thing, but if you don’t talk about it and create clear expectations up front, many people have ruined their relationships this way.
If your relationship is on the rocks, DO NOT try to have a threesome to fix anything about your relationship.
If You’re Single, Be Careful…
The idea of a threesome is often more fun than what actually happens when you get real people to have a threesome in real life. I’ve had threesomes when single, and threesomes while in long-term relationship. Both situations present opportunities, and both present challenges.
When you’re in a relationship, if your partner wants to have a threesome with you, then they can be your teammate in finding a third person to be the guest star.
If you’re single, you’re going to have to do all the work yourself of finding both people, introducing the idea to both people, introducing both people to each other, and communicating skillfully every step of the way.
Do not try to force things, and do not try to rush things. As you’ll hear in the threesome podcast episode on this page, there was a moment when the women were in charge, and I didn’t know if the threesome was actually going to happen or not. I had to give up any illusion of “control,” and allow for the two women to come to their own conclusions (without any pressure from me).
Most Importantly, Learn How to Communicate
This is the key to having a successful threesome, so if you want one, it’s a good idea for you to study up. All the porn videos in the world won’t prepare you for what actually happens in the process of getting three people into a bedroom.
Before you have sex with a new person, or have a threesome for the first time, I HIGHLY recommend checking out my how to talk about sex article (and use it during your first date).
It’ll give you an outline of things to talk about BEFORE sexual activity begins, so you can make sure everyone is on the same page (which is what it takes to have a great sexual experience with real people).
Additional Threesome Stories (From My Personal Life)
Part of my commitment as a sexologist and sex coach is to share real and authentic sex stories from my personal life with you, so you can learn from my mistakes, and learn from what worked well too.
Most of us keep this stuff in private as secrets, which makes sense considering the society we live in. But if the goal is to help each other improve in the domain of sex, SOMEONE has to talk openly about their experiences. That’s why we’re here today.
The stories below are NOT perfect examples of how to initiate or navigate threesomes.
They’re just true stories from earlier in my life. I learned a LOT from these experiences, and now I approach and navigate threesomes with much more intentionality and communication.
Threesome with a Best Friend
This was actually my very first threesome experience. It happened years ago, back when I lived in a large community house with 12 other people in Asheville.
I was in an open relationship with an awesome woman, and she was seeing multiple other people at the time (technically that would be a poly relationship).
One night we ended up laying in bed and telling stories about life with another woman who was one of our best friends. Somehow the conversation turned flirty, and then somehow things escalated very quickly without talking about it, and both women laid on their backs while i fingered them at the same time.
None of us kissed, and there wasn’t much intimacy… But it was erotic! I couldn’t believe I was actually fingering two women at once – women who actually wanted and enjoyed this.
The threesome ended pretty quick though, because I got in my head, and when they asked me what I wanted, I felt too awkward and ashamed to ask for anything… so I said I was content.
This was during a period of my life where I was really concerned with being “a good man.” At the time, I thought this meant being “a safe man” who didn’t have strong sexual desires for women (because I thought that meant I would be an unsafe and “toxic” man). Wow was I wrong…
The next day, we didn’t talk about it. And honestly we didn’t talk about it for many years, until just a couple of weeks ago when the three of us were in the same place again. None of us remembered the entire story, and it was fun to remember together. The good news is that we’re still all friends!
Unplanned Threesome with a Couple (MFM)
Many years ago, on a hot summer day in Asheville, I went to one of my favorite waterfalls with two friends who were a couple in long-term relationship (man and a woman). The vibe had always been great with us, lots of jokes, good conversation flow, and lots of fun with whatever we did.
On our hike back from the waterfall we found a wild patch of Chanterelles (delicious edible wild mushrooms), and harvested them to cook with dinner. When we got back to their apartment, I went to the kitchen to prep the mushrooms. We were having normal conversation, and I turned to face the stove top to sauté the mushrooms.
When I turned back around after a minute or two, they were both standing naked, right in front of me (I was fully clothed and didn’t expect this). Definitely a bold move on their part… a move that I would not recommend for most people… but in this context it worked because we were old friends who knew each other pretty well.
I saw them naked, and internally said to myself “fuck it, let’s go!” I turned the stove off, and started making out with the woman, while he touched her from behind.
Quickly we moved to the bedroom, where the full on sexual acrobatics began (threesomes in real life are very different from threesomes in porn). I went down on her while she went down on him. She went down on me while he went down on her. And they made love next to me while I made out with her. I got to be the guest star that day.
My Sexual Orientation
And for those of you wondering about my sexual orientation, I am heterosexual. This threesome happened during an experimentation period of my life, and I did kiss this guy while the woman went down on me.
At one point the woman was riding my face with me on my back, and the man was going down on me (he was bi). It felt great for a couple of moments, but as soon as I looked down and saw his face & beard near my penis, I lost arousal and lost interest in sex. Our threesome pretty much stopped then (it wasn’t awkward or bad, it just came to an end).
I imagine if I was bi, the threesome would have gone on much longer. It was important for me to experiment during that phase of life.
I decided that if I was going to be a sex educator and talk openly about this stuff, I needed to at least check myself to see if my sexuality was a result of societal programming (homophobia etc), or if my sexuality was authentically mine.
Turns out I’m only attracted to women. And honestly I’m glad I tried other options out to the extent that I did. That was the farthest I’ve gone sexually with any other man. I have had other threesomes with a man and a woman, but on those other threesomes, we (the two men) sexually focused entirely on the woman… giving her a queenly experience.
Unplanned Threesome in Mexico for Multiple Nights
One time when traveling with a group of friends, my girlfriend and I had a multiple night stand with one of the woman who was traveling with us. There were 9 of us, and the evening started with a group massage (non-sexual), where we all took turns massaging each other.
Eventually, people started to go to bed, until it was just the three of us left on the bed… And our massaging slowly evolved from therapeutic into more sensual touch. We didn’t talk about it, we didn’t speak desires or set boundaries or ground rules, we just slowly flowed into sexual touch. And it was a LOT of fun.
Our fun lasted multiple nights together on this trip, and we were flirty through the days too… it was definitely a vacation of sexual adventures.
But, the net result was NOT entirely positive though.
Because we didn’t talk about anything beforehand, we missed some important details that could have impacted our decision to sexually engage. Some hurt feelings happened, with awkwardness that lasted a few weeks after vacation, but luckily nothing catastrophic happened.
Threesomes come with MASSIVE risks. You think having sex with one person is complicated? When you add a third, the potential complications increase exponentially. If don’t talk about sex up front, you’re setting yourselves up for potential failure in the form of pain, disconnection, hurt feelings and possibly even trauma.
Connect with Jon Handelman:
EPISODE MUSIC:
“Pink Dolphins” (Numatic Remix)
Written by: Tony Moss/Sunny Solwind/Shireen Jarrahian/David Brown
Remixed by: Numatic
Want to Support This Podcast?
Share this podcast with your friends!
Buy me a drink and directly support the creation of new episodes. Thank you!
Leave a review on Apple Podcasts or Spotify - it helps get this Podcast out there, AND it helps me know that you care. 🙂
Related
-
April 25, 2022 -
April 18, 2022 -
April 11, 2022