We married young. I was in my last year of college, and Hannah had just graduated. We spent our second year studying in Italy, then returned to the US. Hannah's BA in Philosophy and her fluency in Italian qualified her to work in retail, so she got a job in a local mall.
Her two bosses, both Italians, never knew she spoke their language. She would have told them if they had asked, but they had no reason to assume that a Jewish girl from New York would possibly understand "street Italian." It was after a few months of the partners using Italian to talk to each other about confidential business matters that they suddenly discovered that she understood everything they were saying, so they did the only thing that made sense at that point: they made her a manager.
The raise was great, and Hannah became closer with one of the bosses - Dante. At times he would call her to come down to the store's business office, hidden in the mall storage area. Their conversations started with work, but soon grew more personal. Hannah was very open with me about this - nothing seemed amiss, and we really didn't keep secrets from each other.
Which is why I wasn't totally shocked when she came home one day and said, "Dante made a pass at me today."
"Oh? What did he say?" I asked.
Pause here:
Remember, I had no idea what a cuckold was. I had never heard the word other than in a Shakespeare comedy, and I'm not a fan of Shakespeare. So this wasn't the fulfillment of a long-time fantasy, or even something I had remotely considered before that night. Yet...
a) Dante, who had met me and talked with me many times, felt comfortable telling my wife that he wanted to fuck her.
b) Hannah, who had never heard the word "cuckold" either, felt comfortable telling me that her boss wanted her to fuck him and make me a cuckold. (No, she didn't use those words. But that's what "Dante made a pass at me today" means.) I still don't know whether she told me because we were just open about everything, or if she secretly hoped I'd somehow let her fuck him (but why would she hope that? We had never discussed anything of the sort), but clearly she wasn't worried about me getting a gun and going after the man who made a pass at my wife.
c) As for me, I still think about my response - a response which changed my life. I didn't say, "What an asshole," or "How dare he?" No, my first words were, "What did he say?" WTF? My wife tells me that her boss said he wants to fuck her, and I wanted to hear how he said it. Where did that come from???
...the story continues:
When I asked Hannah what he said, she looked at me a little funny, and then told me. It was more suave than "Wanna fuck?", but not much.
"And what did you say to him?"
"I told him I couldn't; I'm married."
I don't know why, but I ventured further into terra incognita. "You said you were married. You didn't say you didn't want to?"
Now she really looked at me funny. "It doesn't matter if I want to or not; I'm married, so I can't do it."
And now, dear diary, is when IT happened. To this day I can't believe these words came out of my mouth. Oh, I'm immensely grateful that they did, because they changed my life. But again I ask, WHERE DID THIS COME FROM?
"So, do you want to?"
"Do I want to WHAT?" she asked. Her voice expressed surprise, but I thought I detected something else, too. Was it... desire?
"Do you want to fuck him? He told you today that he wants to fuck YOU, so I'm wondering if you want to fuck HIM."
"But. I'm. Married." she said carefully.
"Okay, so what if you weren't married? Or what if I was okay with it?"
"Well, I AM married," she responded quickly. Then she paused before adding, "And what do you mean, 'if you were okay with it'? How could you be okay with it?"
I think that up to this point I had convinced myself that I was just asking a theoretical question - A "do you think he's hot?" kind of thing. But suddenly I had an image of my wife, naked, with Dante between her legs. As if that wasn't weird enough, I also had a raging hardon.
"Well," I said slowly, "If you fucked him, would you leave me and run away with him?"
"NO," she said. "Of course not."
"Would you stop loving me?"
"No way!" she said.
We both knew something had changed, or was on the verge of changing. I realize now that my next words had the power to stop this in its tracks... or not. I chose "not."
"So, if it's not going to hurt us, what's wrong with you having a little fun?" I asked, not knowing how she would react. Would she freak out and call me a pervert? Would she start crying and ask why I was so casual about her having sex with another man?
"But it's not just 'a little fun.' It's FUCKING another man. HOW would you be okay with it?" she asked, now suddenly VERY interested in this conversation.
My answer surprised her. And it surprised me. And it still surprises me more than 40 years later. Possibly the most "cuckold" thing I've ever said, and I said it without knowing the words were going to come out of my mouth.
"Well... Maybe... you could tell me about it... after?"
"Tell you about it? Tell you WHAT? Do you mean, like, details of what we did?"
"Ummm... yes?"
A slight smile formed on my wife's lips. A little scary, but very sexy. When she responded, her voice came from someplace lower. It was the first time in our lives that I heard Hannah sound like she was talking from her pussy.
"How much detail would you want to know?" she asked, not taking her eyes off mine.
"Well, I guess as much as you're comfortable telling me."
"And what would you do while I tell you about what we did?"
"I guess I'd jerk off," I said softly.
"And you'd be okay with that?"
"It might be exciting," I admitted.
She looked at me without saying a word. I was too scared to speak, or even to breathe. It is only now, in hindsight, that I realize what was transpiring at that moment: I was telling my wife that I was not the kind of man who would defend her honor here; instead, I was the kind of... something... that would get excited about her spreading her legs for another man. I often wonder what was going through her mind at that point, and I REALLY wish I knew whether she was suddenly getting wet at the thought that she might actually be able to fuck her boss without destroying her marriage. Hell, with her husband's PERMISSION.
Finally, she spoke. "Let me get this straight. You'll let me fuck Dante if I tell you about it afterwards?"
"Hannah, you're a grown woman. I don't own you or control you, so you don't need me to 'let' you. What I said was, I think I could be okay with it, IF IT IS SOMETHING YOU WANT TO DO. But you still haven't told me if you want to."
She chose her next words carefully. "Look, there are two possible answers I can give here. Are you saying you'd be okay with either answer?" (Was her mind blown at this point? Was she wondering if I was setting a trap for her to say something incriminating? Was she getting wetter?)
Still trying to act casual, when I felt nothing of the sort, I answered. "If you say you don't want to, then we'll keep doing what we're doing, which I think is pretty great. And if you say you DO want to, then I guess we'll be starting on something new and different. So I think I'm okay with either one."
She stared at me for a long time. I stared at her, too, but to be honest, I was still picturing her naked and getting fucked by her boss.
"Okay, then. Yeah," she said softly.
"Yeah what?" I asked.
"Yeah, I guess I want to."
"You want to WHAT, Hannah? You can't do it if you can't even SAY it."
My wife looked hard at me. She knew the significance of what she was about to say, and I'm sure she still didn't understand how this conversation was even happening. (Neither did I. But she straightened her back, looked into my eyes and said, "I want to fuck Dante."
"Wow," I said hoarsely. "Thank you for being honest with me. So how do we make it happen? I mean, you already told him no."
A look of surprise crossed her face and she said, "Wait, are you SERIOUS?"
Now I was the surprised one. We were so close and now she's saying it was a joke? Is she upset, or is she just scared? If she is upset, then this wasn't going to end well, but I hadn't seen any sign that the conversation was bad for her. And if she's scared because this is a wild, weird new idea, then maybe I could help her feel better about the thought of doing this with Dante.
I am now officially thinking like a cuckold.
"I'm serious if you are. You said you want to fuck him; were you being serious?"
Again, a hesitation before she answered. "Yes, I was serious."
"Okay, then. He asked you and you said no, so how are you going to tell him you've changed your mind?"
Forty-one years later, Hannah's response is still seared in my memory. I came to know her expression as the face she makes when she is thinking about fucking Dante, but at that moment it was a combination of sexy, scary, feminine and powerful that would define sex for me for the rest of my life.
"He'll ask again," she said.
"How do you know?"
"I'll make sure of it."
And there it was.
I will remember those words, and the look on her face, for the rest of my life. Because that was the moment when my wife said she was going to fuck another man. "I'll make sure of it" meant, "I will make sure he asks me to fuck again, so I can say yes. I'm not going to tell you HOW I will make him ask again, but believe me, I will make sure he asks."
Right here, my memory fails me. I don't remember what I said after that, but I know we both started to get ready for bed (sleep-bed, not sex-bed!). What I do remember is that during the getting-ready-for-bed process she said, "Do you want to know in advance when it's happening?"
I don't know which turned me on more: having her ask me if I want her to tell me when she's going to fuck him, or knowing that she's working out the details of fucking him right now as we're going to bed.
"I'd like to know in advance, if that's okay with you," I answered quietly. I was embarrassed, feeling the first signs of shame, and so excited that my penis was poking straight out through my pajamas. But she asked, and I wasn't going to pass up the opportunity she was offering me.
"Just the first time, or each time?" she asked. Looking back, I can't believe how calm and level her voice was as she asked me that.
"Huh? EACH time? How many times are you going to do it?" I almost-shouted.
The look on Hannah's face was a combination of amusement, pity and pure animal lust. She crawled onto the bed and lay down beside me. Looking into my eyes she said, "If I'm going to do this, then I'm going to do it a lot. Don't say this is okay without understanding that."
I shook so hard I nearly came. My penis pushed its way out of the slit in the pajamas, and Hannah looked at it and laughed. "I'm guessing you want to know each time, right?"
I hung my head. I couldn't look at her. But I said "Yes. Please."
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