My introduction to cuckolding started rather innocently.  No, that’s not true.  It wasn’t innocent at all.

A friend of mine and I were engaged in what had become a regular CoVid Zoom visit.  We talked about everything under the sun, most often amidst lots of laughter.  When we weren’t deep in conversation, we watched TV shows and movies together.

After viewing an episode from “Billions” where the main male character indulges himself with a dominatrix, she asked what I was doing with my sexual desires during CoVid isolation.

“I masturbate.”

She laughed and said. “Doesn’t everyone?”

I shared in her laughter. “I don’t know. Do you?”

Before answering she looked away for a minute.  “That’s not a simple answer. Before I tell you, let me ask you about your masturbation. OK?”

“Be my guest.”

Forgoing questions, she cut to the quick. “Tell me what you do. Create a typical self-pleasuring scene for me.”

Sharing Secrets Along the Cuckold Road



“Hmmm.” I tried to gather myself before revealing my deep secrets. How much should I share? “Well, let me tell you the absolute truth, I imagine you.”

Fortunately, my words were received with a warm smile. “Now isn’t that interesting. And what do you imagine of me?”

“I imagine what your mouth tastes like, what your exhale smells like, how your lips pucker when we kiss.  I watch as you pull away and undress just for me. You dance and bit by bit show me the parts of your body you otherwise keep under wraps. Your hands lead me on an erotic tour that starts with your neck and slides down to pinch your nipples. You raise them to your tongue until they glisten with saliva. And then you circle your belly and part your thighs. Your pussy is shaved.  I watch it moisten in response to your touch, in response to my desire to put whatever parts of myself that I can inside of you. Your fingers glisten like your nipples and when you rub those pussy laden fingers along my lips, I want to come.”

Awaiting Answers During My Introduction to Cuckolding



We look at each other in silence.  “Whew,” she says, “I wasn’t expecting all of that.”

“Too much?”

“No, just right. Let me compose myself.” She takes a drink of water and fans herself. “So, it’s safe to say you like to watch.”

“Yes, I like to watch, preferably to watch you.  I never tire of imagining you naked. Enough about me, though, it’s your turn. Tell me why your answer to the question about whether or not you masturbate is not so simple.”

“I’m sorry my dear friend, but that is going to have to wait.” She anticipates my response and says, “don’t worry, I will tell you, in due time.”

We exchange good byes and return to our pandemic sanctuaries.

Immediately, I fantasize her masturbating.  My mind pictures her lying in bed with a favorite sex toy. As I try to imagine more, my phone notifies me that a text has arrived. I open it to find message that reads, “Here’s the first part of my answer.” A series of photos follow her words: images of what I imagine when I see her in my mind’s eye.  “I think we are a good match. You like to watch and I love to be watched.”

So, that’s how my journey into the world of cuckolding started.  It progressed from there and continues to do so.

What is Cuckolding?

Cuckolding derives from the Cuckoo bird and its tendency to lay eggs in another bird’s nest. The female bird’s apparent disloyalty to her mate is the source of cuckolding’s negative connotation.

“With that whiff of unfaithfulness, the carefree bird gave us the word ‘cuckold,’ which came in the Middle Ages to mean a husband with an errant wife,” the BBC’s Janet Williams wrote. “But there are more subtleties in that rude gesture. The word ‘cuckold’ also implies that the husband is unaware of his wife’s infidelities. And he might only find out on the arrival of a baby — palpably not his. Which takes us back to the cuckoo.”

Cuckold’s modern definition differs from its ancients roots insofar as a partner’s apparent infidelity is no secret. Instead, it’s a committed relationship where one partner finds pleasure watching their mate have sex with a third party.  Traditionally the person watching, the one being ‘cucked’ is a man, referred to as a ‘wittol’. He gets off—and suffers humiliation–watching his female partner have sex with a more well-endowed man.

Back to My Introduction to Cuckolding Journey



It soon became clear why my partner’s response to my masturbation question was not so simple.  What started with her sending me erotic photos of her glorious naked body, evolved to watching each other masturbate.  And then she took it a step further.

You’re not the only person I do this with.”

At first, my heart sunk.  I felt like she was cheating on me.  Given that my ex-wife had affairs throughout our marriage, my partner’s admission was my worst fear. We tried to talk our way through it.

“Maybe the best way for you to finally leave that fear behind is to confront it.” She wisely suggested. “I had a cheating partner, too. And, I always wished that I could catch him in the act.  Maybe I was mistaken but I thought if I could see his infidelity with my own eyes it would somehow lessen the power his actions had over me.  I could steal his secret and get over my lingering fear.”

Beyond My Introduction to Cuckolding: Developing Trust



She let me ponder her words and then asked a question that lay at the heart of our connection. “Do you trust me?”

I thought I did. The more we talked, though, the more I realized I didn’t. My fear of infidelity meant I never trust anyone I cared about.  Eventually, I thought they’d all find someone else. “I want to.  The strange thing is that my first reaction to what you just told me was to run and hide. But, the more we I think about it, the more I realize that you’re being honest. Your openness makes me trust you more than anyone else I’ve been with. I think trust means being with someone without fear. I want to get to the place with you.”

“So trust me on this. I commit to being in a primary relationship with you. But, I want to have other sex partners and I want you to be a part of everything I do.  I want you to watch knowing that when I’m with someone else it’s really about being with you.  My gut tells me that if you can find pleasure in watching me with others, you will kick your once and for all kick your infidelity fears to the curb.  I promise we will talk our way through anything that comes up. OK?”

At that moment I realized that I loved this woman very much. I loved her to the point I was willing to trust her and be her cuckold.

Cuckolding Challenges

When the pandemic relented, we moved in together. Without strong communication, we never would have made it.  I had lots of insecurities to overcome.  She had lots of boundary issues we needed to negotiate.

One of my biggest concerns was could my partner respect me if I was relegated to role of an acquiescent observer? I needed to be secure in my role.  In addition, she needed to constantly be aware of her choices and not get defensive when I communicated mine.

I felt the need to create common understandings. Her initial response was the ultimately the choice as to where she decided to lay her eggs was hers and hers alone.  Things changed after a sex partner decided he wanted to be more than fuck buddy and followed her home.  They really changed after a different guy got rough with her.

Clearly, we needed agreed upon rules.

Our Cuckolding Rules

First rule was no secrets. Second rule was no unprotected sex except with me. Third rule was full disclosure to all parties about the nature of the arrangement.  Fourth rule, a tough one, was we had to reach consensus on all decisions.  Finally, our points of emphasis were communicate, communicate, communicate.

Still, both of us had to overcome our traditional notions of a loving relationship.  Girl on the Net captures the dilemma well in an Esquire magazine piece. “Most of us have grown up being told that love and sex should be between two people, not two people and a guy called Brian that you met on the MF4M section of Craigslist.”

To my dismay, I became jealous when my partner described the details of great sex she had with other men.  Neither one of us felt good about my jealousy. With my partner’s help, I eventually worked through it.

Not surprisingly, I didn’t react the same way when she hooked up with women.  I had to draw a line, though, when she told me about a guy who got rough with her.

In addition, I drew another line when she asked me to join in with a man she felt totally comfortable with.  Again, my boundaries, fears, traditional attitudes held me back. Participation with another woman, when beckoned, I was willing to try.

What I Learned from My Introduction to Cuckolding

Clearly, any relationship can struggle trying to keep up with change.  Change is inevitable and desirable.  We want each other to grow, meet new people and expand our comfort zones.  Growth leads to healthy transformation which enhances existing relationships.

Yet, if you’re not ready, too much change, too fast can undermine what you have.

We took turns calling for things to slow down.  And, we took turns shouldering the many ups and downs of our choices.  Ultimately, we found what Dr. David Ley concluded to true about cuckolding.  “Overall, our research found that for the most part, cuckolding tends to be a positive fantasy and behavior. It doesn’t appear to be evidence of disturbance, of an unhealthy relationship, or of disregard for one’s partner.”

In the end, we also found the key word in Dr. Ley’s research to be “tends.”  Sometimes it works, sometimes it doesn’t.  Cuckolding is a big leap into a totally different world for most couples.  So, make sure you take the leap with your eyes wide open. You don’t want your desire to cuckold to be an endless freefall.

My most profound learning along my still unfolding journey was also my simplest.  No matter where I venture with the woman I love, nothing rivals the moments when I look deep into the dark wells of her brown eyes. Yes, I do trust you and feel your love each time your eyes meet mine.

All sources available upon request