A Cuckold's Diary Ch. 00

"Prologue: How it Began"

The events described here happened in the 1970s. Before smart phones. Before the Internet. Hell, before Penthouse Letters. Which means that what I was (a cuckold) and what I am 40+ years later (still a cuckold) were not things I heard about and got curious; apparently they sprang of their own accord from my fertile and fevered little brain. This matters, because I am often asked where my desire to be cuckolded came from. Herein, my best recollection of how it all began.

Part 1 - The Conversation

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."

*************************

Part 2 - First Date

Four days went by after our conversation. I knew it was on her mind, so I didn't feel the need to ask her for an update. On the fourth day I stopped by her store on the way home from work, and she ran to greet me and hug me. As we hugged she whispered in my ear, "I have a date tonight."

She seemed so happy. And to be honest, the passionate hug she gave me got a rise out of me even before she told me the news.

"He asked again?"

"Yes."

"And what did you say?"

"I said yes." She moved back from hugging me, and it was clear she was waiting to see my reaction to the news that it - IT! - was going happen. Looking at her I pictured her naked and spreading her legs for her boss, and the words came out without any filter.

"Oh my God, that's great!" I said. "How did you get him to ask?"

I could see the relief on her face: our conversation the other night still stood! She relaxed before my eyes, lowered her voice and said, "Leaving an extra button open on my shirt was all it took."

I checked out the button-down shirt she was wearing. Two buttons were undone at the top, and the effect was modestly sexy. I tried to picture what would be visible if another button was undone, and again, the words just fell out of my mouth.

"I hope you're wearing a pretty bra."

The weird thing was, I really meant it. My head was spinning from a hundred images and thoughts that were competing for my brain's blood-deprived attention. The image that won out was of my wife opening her shirt so her boss could see her bra... and what was in it. And the winning thought was that she did it to let him know that she changed her mind about fucking him.

"I am. I was hoping today was the day, so I came prepared."

"Could you show me? Could I see what he saw?" I was suddenly overcome with embarrassment, and was about to apologize, when Hannah looked at me and smiled.

"Sure," she said. "I'd really like to show you. Come with me."

We walked together to the back of the store, and as we walked Hannah undid another button. Then she bent over, as if straightening the merchandise on a low table. I looked and saw... everything. I saw her bra - black, lacy and low-cut - and I saw the pale skin of her breasts through the lace. She saw me looking (staring, actually) and said, "That's what he did when he saw me, too."

"Then what happened?" I whispered.

"Each time he looked at me, I smiled at him and held my pose. It took about ten minutes before he said, 'That's a really nice view.'

"When he said that, I knew it was time. I stopped smiling, but never looked away. I said, 'There's a lot more to see, if you're interested.'

"I watched his face, and saw him look down at my tits again. He said, 'I'm VERY interested.' So I have a date tonight."

Months later, I asked her if it was hard for her to say that to me - to tell me she was going to fuck another man. She said she thought it would be, but my reaction was so positive that it was way easier than she expected, especially when I asked to see what she looked like with the button open. We didn't know it at the time, but we were setting the ground rules for the next four years of our marriage: she would fuck her lover, and I would help her feel good about doing it... and get VERY excited.

And wow, was I excited. I thought I would burst out of my pants. If I could have, I would have pulled out my penis and masturbated right there, seeing my wife's body the way her soon-to-be lover saw it. Looking at her lace-covered breast, I remembered that she had said she would "make sure" he asked again. She sure as hell did.

She remained leaning over as long as possible, then quickly stood up, buttoned that extra button and said, "Time for me to get back to work."

"I hope you have a really good time tonight," I said softly.

She looked at me with a mixture of love and amusement. "You really mean that, don't you?"

Her asking me that made me think about what I had said: I told her I hoped she enjoyed fucking another man tonight. Again the image of her naked, lying down and spreading her legs for Dante flashed in front of my eyes, and I realized that I actually DID mean it. And right now, my job was to make sure Hannah knew that I wanted her to do this.

"Yes, I really mean it. Do you still think you can tell me about it afterward?"

She smiled with that combination of happiness and what I was just beginning to understand as her look of sexual excitement. "I promise I'll tell you all about it when we're done," she said, using the pronoun "we" for the first of many, many times.

I went to give her a kiss goodbye, and she offered me her cheek - not her lips. I kissed her chastely, said "I love you," and I left.

I was home by 6:30, and the store didn't close until 9:30. I jerked off as soon as I got home, and came - hard - to the image of Dante seeing my wife's nearly-exposed breasts and the thought of how much more he was about to see. I foolishly thought I would be able to relax, at least until 9:30, but by 7 I gave up and started masturbating again. I didn't eat dinner because I would have thrown it up. I didn't have anything to drink. Hell, I'm not sure I breathed. But I kept stroking my penis until the old-style digital clock clicked over to 9:30.

At 9:30 it's fair to say I lost my mind.

Closing the store was a process: get the last customers out, close everything, vacuum and count the registers. Hannah had done it many times, so I knew it would be at least 15 minutes before they were finished working. Or would it be? I remembered times when they absolutely had to get out early, and on those days they managed to get everything done before the 9:30 closing bell. Was this one of those times when they had something more important to do than store chores?

It's 9:35. Have they started?

9:40. Now?

9:45. They're ALWAYS done by now. They must be... what? Kissing? Touching? Fucking?

Is he hard? Is she wet? Is my wife fucking her boss RIGHT NOW?

At 10:20, Hannah gave her "I'm home" pattern of doorbell rings. I met her at the front door, still naked and still masturbating. As soon as she closed the door I said, "Are you okay?"

Later she told me that seeing me standing there jerking off was exactly what she needed to see. With one look, all her worries about whether I could really "be okay" with her fucking Dante - and enjoying it - were relieved. She gave me a big hug (standing beside me, to avoid getting poked) and said, "Yeah, I'm okay. I'm really good."

"Did you have a good time?"

"Yes."

"Did you fuck?"

"Uh-huh."

[OMG - SHE FUCKED HIM!]

"Did you cum?"

"Uh-huh," she said. She paused and then added, "Three times."

"You came three times??"

"Uh-huh."

"What did he do to make you cum each time?" (Are you still with me? Yes, I DID want details.)

"He fucked me," she said with that wicked, sexy smile.

"You came three times while he fucked you??" I couldn't believe it; in all the time Hannah and I had been having sex, she had never cum more than once. Ever. Did she just tell me that the first time she fucked him, he made her cum more than I ever did?

"You came three times while he fucked you? Wow... were they big or little?"

"The first one was medium. The other two were BIG. The last one was REALLY BIG - that's when he came."

"You came together???"

"Uh-huh. And his was big, too." She smiled as she was obviously reliving the feeling. "REALLY big."

"You made him cum... you made him cum IN YOU?"

"Uh-huh. He came so hard I felt it shooting into me."

"Really? You felt his cum shooting into you?"

"Uh-huh. Five or six times."

PAUSE HERE:

If you are not a cuckold, then what you just read should immediately cause you to think really horrible things about me. Hell, you're right. But as a newly-minted cuckold who still didn't even know what the word meant, I was absolutely thrilled that my wife was willing to share such intimate details of her fucking her boss. It had really happened, and she was comfortable telling me about sex with another man.

We went into the bedroom, where we sat facing each other on the bed while she told me everything that happened. When she skimmed over something I asked her for more details, and each time she happily went back and filled in the particulars. When she got to her third orgasm - the one where he came, too - she said she thought she was a little too loud, and she hoped no one was walking by the store right then.