Guest Column: Dating Online Series. The Cuckold Experience? Part I

by Ms. Jennifer

I’ve been having phone sex with Edwin.  Edwin who lives almost four hours away isn’t really viable, but darn I’m attracted to him.  

The conversation: Quickly it leaves the mundane world and he’s asking me questions like “how often do you masturbate?”  The “boy” isn’t wasting anytime.  

In the spirit of our communication I tell him “I want you to make love to yourself and to leave you wanting more I’m going to crawl into my bed alone.”  

He responds, “I never masturbate alone.” 

At this point there is still some chance he will be in New Orleans this weekend.   He’s asked if we meet for dinner and then, “you stay with me if you are interested.”

“Let’s get you here first.  We can meet, that’s what I can promise.”

“Fair enough!   I’m going to bed… are you going to masturbate tonight?”


“Damn, will you let me watch sometime?”

“I don’t understand why you can’t make love to yourself?”

“I would if you were watching, there is no incentive alone.”

“Yes, to move your energy, to feel good, to explore yourself?”

“I know how I feel already.  More fun with a semi-active partner.”

The next day I hear from him again: “Been thinking how nice it would feel…to kiss your breast…..”

But today I’m not feeling it.  What’s the point of getting excited with a fantasy?   Beside, maybe the guy is really 600 pounds and into wearing red panties.  That in and of itself isn’t a problem, it’s just 600 pound in thong ain’t hot. 

“Are we not talking anymore?”

And I like the way he asks for more without assuming anything or making anything up.  And I write him some great response with I can’t send so I start over.

“Sorry, I want more than a fantasy.  I have so much more to offer than that.  It’s not that I haven’t enjoyed talking with you, and maybe I should just look at this as transitory fun, but ultimately it’s like having dessert without a full meal. And I want the full meal. Even when I meet a real person and open up and then they disappear, it just all feels so fleeting and harder to invest or be hopeful. I’m very attracted to you, but you are a photo and without meeting I don’t even know if you are real or a figment of my imagination.  You don’t live close by and I can’t seem to do a quick (or long) fuck and then let go.  I don’t seem to be built that way.”

Now, I’m wondering, since I got real, if I will hear back from this guy. The fantasy fun is over and I’m opening up more about who I am.

“Hi, I’m very real, but also understand your feelings towards our situation.”  He may be moving back here at some point and meanwhile he hopes I meet a great guy.  

Now, I like this guy even more… 

A few days prior Daniel blew me off earlier for our date with less than an hour notice and my dad is driving me nuts. I was going to blow Daniel off, but then I saw him back online during the time we were supposed to be out, but then he “forgot” that he had plans with his buddies. 

Of course, my initial reaction is what “bullshit,” but I think about it a little more (I’m learning) and decide to tell him: “I was looking forward to meeting you tonight. It’s disappointing to get basically no notice and then to see you back online?  I am the real deal and I can guarantee you, I would have been more interesting that a computer screen….lol.”

I thought that would be the end of that, but last night I talked to him on the phone. He just lost his father and is moving so it reminds me that I don’t really know what’s going on and it’s probably better to assume the best rather than the worst. Of course, sometimes I will be wrong, but i will be happier if I assume the best about people.   

But what does ANY of this have to do with Cuckold 101? Well, that would require me telling you about Anthony (Antonia)? The more I learn the more he reveals. It’s funny how the submissive lets you know all about what he wants in the form of a question.  

He starts by asking “do you want me to be yours?”

I have no idea at this point.

“I have learned to cool my jets,” I respond.

But I start to thaw, “what a sweet thing to say.”   You are putting yourself out there.  Talking a risk and that doesn’t go unnoticed….these things take time.”

“Yes, Mistress Jennifer…. I know.”

He says he’s always wanted “a girl to tell me I am required to marry her.”   


I reward him with a photo of my naked back.   

“Oh God!!!  Can I be your personal valet and servant?”

I find out he works from home.  

“So you have freedom.  Nice.”

“Until you take it away when I become yours.”

What man has said this to me?


… “she made me get my chest waxed.  You like that?” 

 I don’t reply instantly.

“Never mind.”

“Busy. Will check in later.”

“I’m sorry I won’t do it again.”

And we do this dance…. he asks if i mind that he’s twisted. and then drops relentless hints.  Will you take me to get my body waxed?  And this becomes his mantra.  He needs to be humiliated.

But he keeps asking questions.

“You need a domme.”

“You think so.  Is that you?”

And “this mistress is telling you she’s going to sleep you little shit.  How was that?”  lol

“You like this don’t you?”

“It’s making me laugh, but I do not want to get stimulated so I can’t sleep.  I’m not sleeping much these days with my dad’s demands.”  

“Will I need to wear a bra under my shirt?”

“You aren’t giving me an order, are you?”

“No sorry.  I would never give you an order.”

“Do you want a twisted boyfriend?  Who will do anything you want?”


“I’m sorry I told you.”

“I just woke up. I appreciate you being vulnerable and opening up to me.   There is a lot I don’t understand why u like this, but there is a lot of shit I don’t understand. I assume you don’t understand why you want to be humiliated?  But does it matter?  I would be curious, but not judgmental.”

“Do you like me?”

“I’ve learned over the phone an amazing conversation means nothing more than an amazing conversation.  I have learned perfect on paper means jack shit in person.”

“I’ve learned that loving someone as deeply as you know how to love doesn’t mean they won’t betray the shit out of you to get what they wants and they will run you over if they have to.”   

“You should be a little more positive about that I think.”

“I have learned that opening up to someone new and starting to reveal yourself can come across as having too many expectations rather than just being vulnerable.”   

“Don’t compare me to the shithead you’ve been with, they bear no relevance to me.” 

“Well, that of course that’s true, but we don’t come in as blank slates, now do we, baby?”

“No Miss Jenny we don’t.  It’s not fair to compare me.”   

“I didn’t say you are like all the shitheads I have met.”

“I like when you yell at me.”  

“The more connected the more afraid I feel, but isn’t that true for most people?  It’s an oxymoron.  You want to protect and you want to connect deeply.”

“I’m not afraid, but I understand you.”  

“Is it a fantasy to think there is one man who can fulfill all my needs and desires?  Are we human beings destined to want something new or what we can’t have? Can the erotic and domestic co-habitat? ”  

“I have had something new.  I want something forever.”   

“Erotic and domestic co-habitat?   Yes…especially when your erotic partner is yours totally.”

“Like after the “new relationship energy” has worn off you can still want to fuck my brains off?”

“Yes, Miss Jennifer.”  

And I warn him about the BS that he shouldn’t offer himself to me… we haven’t even met.

“I’ve offered it and I think you want it so its probably a done deal.”  

And then he brings up chastity and I’m not exactly sure what that means. 

“No sex with anyone else but me?”

“Yes, you have control over my equipment. You lock me and of course I become yours.”

Suddenly, I’m realizing how much I like the power of this.  I’m surprised at my thirst for it.  Really surprised. The idea of total control is VERY seductive.  Especially when I feel men’s needs typically dominate women’s needs.   How unusual that I’ve met someone who is willing to let me have the reins.  I can imagine the pressure of this responsibility, but in general I’m thrilled with my female privilege. But we haven’t met yet.