The Best-Laid Schemes

Story Info
Gang aft agley.
4.1k words
4.04
22.3k
42
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
stev2244
stev2244
1,935 Followers

"So you've decided to turn me into a cuckold?" I asked my fiancée Anna, still a bit in shock. Quite a bit of shock, actually. This was a life changing moment for me. Nothing had hinted at what was currently unfolding. Just a few minutes before, we were busy with our usual Sunday breakfast and I remembered clearly thinking how much I had lucked out with getting Anna to accept my marriage proposal. Sure, she was a bit quirky sometimes, but nothing horrible so far. Now I held my cooling and unnoticed cup of coffee in my right hand while trying in vain to get a grip on what she had just dropped upon me.

"Tom, honey, it sounds so unloving and cruel when you say it this way," she said, sounding empathic. "Cuckold is such a dirty, demeaning word. You're not going to be a cuckold, you're going to be a hero, a man who is getting a unique opportunity to prove his strength, his confidence, the level of his love and devotion. You're the love of my life and nothing will ever change this. I wouldn't dream of removing this lovely ring from my finger and I'm definitely going to marry you as planned."

That was a lot to digest. No communication was necessary at this point. She had clearly expressed her wishes. The mere talk we just had had already changed our life, our relationship. She had challenged me to prove my love. Did I still love her? Did I accept that challenge? Was this even a completely bad thing? Maybe there was some kind of stimulus in it for me as well? Might be worth a try. There had to be excitement for the cuckolded man in this whole concept, otherwise it wouldn't happen as frequently as she said it did. What was the allure in this? Well, only one way to find out, right?

I came to a conclusion.

"I understand what you're proposing... no, demanding," I cautiously began. "May I ask where this sudden change of behavior comes from?"

"Tina...," she started to gush, obviously interpreting my reaction as not being totally averse to this whole thing. "You see, Tina tried this with Mark for a while. Although he didn't want it in the beginning, he came around quickly and enjoyed it a lot after a while." Mark? Really? The self-declared alpha male Mark? So there really had to be something in it for the cuckold. Well, assuming she was telling the truth. But it didn't matter too much, I would be experiencing the whole thing up close and personally anyway, it seemed. She was smiling widely now, assuming she had convinced me already with her considerable female charm. Even though I always enjoyed said charm, it seemed I had just seen a totally new side of my loving fiancée.

"Mark? Seriously? I'd never have guessed," I answered, avoiding any mention of my own feelings. I was still a bit undecided about those.

"It doesn't make him less of a man. On the contrary, I think it shows how super-mature and self-assured he is and how much he loves and trusts her. However, it spiced up their sex life a lot." She was babbling again; the pure joy of her perceived success was practically pouring out of her, and it was almost infectious.

"Wow. They're still doing it?"

"No, they stopped when she had their first child."

"Anna, this has the potential to alter our relationship permanently. Have you thought this through? You're really sure about this?"

"Yeah, kind of." She pretended to think about it for a few seconds. "Yeah, I am," she firmly declared.

"This is a serious decision, possibly changing our whole relationship."

"No, it will be just a bit of harmless fun for a limited time. Afterwards, we will live our lives as a conventional couple, happily remembering this exciting time of our lives."

"May I ask if you have already decided on this or if you're merely proposing this?"

"Tom, I really love you and I know you're reluctant to try this. But yes, this is decided. I need this experience. And to be honest, I even had a bit of a jump start, yesterday."

"Huh?"

"You see, Roberto can be quite convincing."

"What? Roberto? Who is Roberto?"

"You don't need to worry at all, dear. Yes, he's very handsome, but so are you. He's charming and good at sex, but he has nothing on you in these regards. It's just this whole cuckold situation that makes sex with him so damn hot and mind blowing. Roberto is very experienced, he has already done this for others, like Mark and Tina. This has helped them sooo much," she happily exclaimed.

"I bet it did," I drily stated. She wrinkled her forehead a bit, but chose to ignore my less than enthusiastic reply.

"Anyway, we just knew that you'd come around to this. I know how strong and self-assured you are, how much you love me and how open you usually are for kinky ideas. I might have jumped the gun a bit, but we saw no harm in getting going when the opportunity arose."

"Wow." This was a lot of news at once. I felt a lot of strong and widely mixed emotions about the whole thing. "So, what would be the rules?" Not the most intelligent question, but the only one I could think of.

"Well, Roberto is going to fuck me, of course." She even giggled a bit. "No making love, just pure unadulterated sports sex. That's the whole point of this game."

"I see. And what about me? What's my role in this, apart from being the cuckolded fiancé?"

"Roberto has agreed that I'm still going to be allowed to service you orally. But you using my pussy or my ass, or giving me orgasms is a no-go from now on. I know it sounds weird, but these are his rules and he's certainly the expert here. That's obviously quite a sacrifice for me as I love having sex with you, but I've decided to go along. Of course, he's going to use me in any way he wants, including anally."

"Really? You never wanted..."

"Yes, I know. We never tried that. I still don't fancy it, but it seems quite important for him."

"Wow. I see." I never understood some men's fascination with anal sex, so this added detail was no big deal for me. She knew me well and was quite aware that I would need time to think over this new information. She again waited patiently for me to finish.

"So, this will be only for a limited time?"

She jumped up in pure joy and threw her arms around me, assuming I was on board with this.

"I knew it," she squealed. "I just knew it. You're simply the best. Ah, Tom, from now on I will call you Tommy instead of Tom, okay? That's part of the cuckold game."

"Hmm... okay." I never liked that name, but hey, it was part of my role, wasn't it? "Do I at least get a last fuck?"

"No, Tommy, I'm terribly sorry, but Roberto has forbidden it. The game is already on. You are already a full-blown cuckold. I will just have to make sure that the pun fits," she explained, giggling a bit.

"I see," I said as she began to get on her knees in front of me, taking my cock out of my trousers and into her mouth.

* * * * *

Reluctantly, I opened the door a few hours later to find a guy, presumably Roberto, standing there. He offered me his hand, grinning widely. I ignored his hand and just stepped aside. He seemed a bit surprised, but got over it quickly, his arrogant smile returning. At least I felt like I had scored a point, small as it may be. But then I remembered why I was there and what my role was to be. I wasn't there to score points or to win. My job was to be cuckolded and to lose. I realized that this was way more difficult and it would take a while for me to get used to it.

I thought that the whole point of this was to make me feel humiliated and jealous while having to watch Anna greet this Roberto guy with a deep, passionate kiss and it fully lived up to the expectations. Boy, did this hurt. I felt my eyes starting to water while my emotions varied between anger, hurt, humiliation and, surprisingly, excitement, all in industrial strength.

Anna had described Roberto as a handsome and charming man. Well, I could hardly judge his charm at this point, but he seemed mostly arrogant. Maybe Anna liked it this way? What confused me were his looks. I always had problems judging the attractiveness of other men, but this guy seemed surprisingly unremarkable and even unattractive. Come to think about it, he didn't look even a bit Latin. I asked myself if Roberto might be a stage name. He looked like a Walter or Michael, just some normal guy. He was a bit smaller than me, definitely a lot less muscled and not in nearly as good shape. I was almost disappointed, having expected a big, mean and dominant hunk and not a smallish accountant type with a receding hairline. But hey, this game was played solely in the minds of the people involved. Physical appearances probably weren't too important. What was happening was essentially between Anna and me, this guy was just a tool.

I was still curiously soaking up all these new experiences and insights. I certainly couldn't be described as enjoying this situation, but it was definitely very interesting. And while I was far from being an adrenaline junkie, I felt a lot more alive than I had for quite a while. All of this was as exciting as I had expected it to be, but unfortunately, not in a purely positive way.

Anna chose this moment to wobble past me on her unaccustomed and obviously recently purchased red high heels with him in tow, leading him towards our bedroom. I had never seen her wearing the like, and to be honest, it looked a bit ridiculous on her. There are women who CAN wear such shoes and walk in them like they were sneakers. Anna was clearly not one of them.

As she passed me, I saw a white tag had escaped her obviously newly purchased black lace panties, pointing upwards along her spine. Anna's unsteady stride and the sticker gave the whole scene a definitely amateurish look. If she wanted to achieve the cuckoldress/slut/femme-fatale ambience, she still had a long way to go. There also was a small green "Q.C. Checked OK" sticker on her panties, right on her ass cheek. This described her ass quite well and seemed more appropriate than the cheap looking garment, I thought.

She kissed him briefly but deeply and went to her knees in front of him. While I watched her sucking his dick, a whole new bunch of emotions passed through me. The humiliation was now mixed with a pinch of arousal and other emotions.

After a bit of sucking, which was accompanied by exaggerated noises worthy of a cheap '70s porn movie, they announced that they were retreating to the bedroom to start the main event and that I was invited to watch them. I politely declined, already having received an entirely sufficient dose of cuckolding experience for the day.

To my surprise, they managed to increase their general groaning and moaning level, making the scene even more unbelievable. "Ah, ah, ah, uh, yes, do me! You're so good!" and so on. This didn't sound like fun, but I realized that this whole cuckolding thing was not mainly about fun. They were doing this at least partially for my benefit. We were all just playing our assigned roles. I was supposed to suffer, which for some reason Anna planned to derive pleasure from. I sighed and retreated into the guest bedroom, which was now officially my room. Cuckold country, as Anna had described it. I wondered if I would find some cheesy sign on the door: "Welcome to Cuckold Country!" I was not supposed to soil the bed for her lover, she had explained. I asked myself what I had let myself in for and how long I'd be able to endure it. Although this whole thing was an interesting experience in its own way and some part of my varied mix of feelings was arousal, I still doubted I would be able to stand this for very long.

* * * * *

In the following weeks, they never met at his place. They always had their trysts at our home, in my former bed. I understood that completely, meeting somewhere else would remove an important part of this game--my humiliation. So, she usually went out with him, always dressed to the nines, parading herself in front of me. Greeting him enthusiastically in front of me. Going out to meet our friends and openly discussing her having a lover with my consent. Coming back to our home to gloat. Retreating to her bedroom (our former bedroom) with much fanfare. Whenever they were around, I was invited to watch them. Sometimes I did for a few minutes, usually I didn't. The novelty of the experience wore off after a while. I still felt some interesting and conflicting emotions, but they were not as strong anymore. Anna was always affectionate and loving and offered blowjobs several times a day, but only when Roberto wasn't around. Roberto was always a bit arrogant, but mostly ignored me altogether. For a while I accepted the blowjobs, but after a while, I didn't want them anymore. Surprisingly, Anna was quite unaffected by this change.

* * * * *

"Tommy?"

"Hmm?" I was reading a fascinating book and had hardly noticed their sex show today. Roberto had reached his climax with some kind of loud rutting call--he sounded like a water buffalo on one of those nature channels--and Anna had screeched like a little girl. They were acting weirder by the day, obviously trying to keep the game interesting. He had claimed her last virgin orifice long ago, so I didn't see too many options for them to further up the ante and keep things hurtful for me.

"You see, sex with Roberto is very exciting. You can probably hear that; my reaction is much stronger than it was with you back when we still had sex."

"Well, you seem to be much louder," I cautiously answered, avoiding any statement about their credibility.

"Right." She seemed very excited, there clearly was more to come. I expected some new addition to keep their humiliation game interesting and wasn't disappointed.

"You see, as exciting as giving myself completely to this dominant man and marvelous lover is, there is one thing that would make things even more thrilling."

I just looked at her, politely awaiting the news.

"He calls it repro sex."

"Retro sex? You mean, like they did it in the old days?" Here I thought sex had pretty much worked the same way since the very beginning, but I guess there was always something new to learn.

"No, Tommy, repro sex. As in reproduction. According to Roberto, the possibility of getting pregnant enhances the feelings a lot, for all of us. I can't even begin to describe how excited I am about this. What a thrill! Just imagine it--every time he comes in my pussy, I might get pregnant with our first child! I never came so hard as right after I agreed to this, even though I was still on the pill."

"Our first child?"

"Yours and mine. Not his, of course. The child will be ours in any case, Tommy," she sincerely stated.

"I see," I answered in a neutral tone.

"The second child can be sired by you, of course. At that point, this whole game will have ended anyway and I will be yours alone again, like I've promised."

"I see."

"I see? That's all you have to say?" She seemed a bit disappointed by my reaction.

"Well, of course... well..." I was actually at a loss for the right words. "I'm glad that you find such a big satisfaction in this."

"You bet, Cucky." That still stung a bit.

"So, when are you going to start?"

"Start?"

"When are you going to go off the pill?"

"Oh. That was about three weeks ago."

"Oh, wow. So, you might already be pregnant?"

"It's unlikely, but I might be soon. Isn't that exciting?"

Well, yes, it was exciting all right, along with several other feelings. I had to admit that I felt the rush of adrenaline that I hadn't felt for the last few weeks as the so-called game grew more and more stale. So, in some perverse way the new turn of events made sense.

"This game will end with our first child, just remember that. You're not going to be a cuckold anymore then, never again. You're going to be a proud man again, my man. I'm going to be only yours again. We're going to be so happy." She was gushing with happiness.

"I see that this makes you happy."

She confirmed this by squealing.

"Just remember, as soon as my belly starts getting really big, Roberto has agreed that I'm yours again forever. Isn't that great?"

I nodded to confirm that I had understood, smiled and turned to my book again.

"A blowjob maybe, just to celebrate?"

"Ah, no thanks. Those should be reserved for Roberto."

She frowned a bit, but left it at that.

* * * * *

A few months later two things became apparent. Her growing belly and Roberto having left for parts unknown. Anna came into my room dressed to the nines, smiling expectantly.

"Tadaaaa."

"Tadaaaa?"

"Yeah. Tadaaaa. You have your loving wife back."

"Well, technically..."

"I know," she interrupted me. "We're not yet married. But you're my fiancé, my man--always have been--and I'm your woman again. Roberto has left the scene forever."

"He has?"

"Yes, and like I promised, I'm yours again forever."

"So, it's done? You're actually..." Yes, I know, it was a silly question to ask while looking at her swollen belly.

"Pregnant, yes. Isn't that great, honey? We're going to be proud parents."

She tried to act overjoyed, but it didn't seem sincere. Actually, she suddenly seemed nervous. I looked into her eyes, I looked over her face and her body, taking my time. Suddenly I felt like I had just met her. There was a woman standing in front of me. Did I like her? Good question. I didn't know. Did I love her? I remembered that I once did. Now, she was pregnant with another man's child, conceived in a deliberate act of betrayal.

She wanted to marry me.

She expected to marry me.

Did she? She looked at me with an unfamiliar, clearly anxious expression. This was a life changing moment and we both saw it with crystal clarity. Things had changed, the clock had been reset, all choices had to be made again.

"Tom..." She was at a loss for words, which was unusual. Her insecurity emphasized the new shift of power. "Tom, I hope you've never doubted my love for you. This was just a short aberration, an exciting experience before our married life starts. Consider this like marrying a single mum. Only in my case... I don't know. Tom, please say something."

"This leaves you in a quite difficult situation, doesn't it?"

"Leaves me? What? Why? You have me back now. I will never even look at another man from now on. I've had my experience; it was a kinky adventure for both of us. That whole cuckold fantasy is safely behind us now. Now it is time to go on with our life and plan the wedding before I start to show too much. We will meet our friends a lot to show them I'm your woman again, fully committed." She was talking too loud and too fast now.

"Hmm. You're pregnant, unmarried and have a low-paying job. That sounds like a bit of a problem." I was so damn calm. This was not an act; it was how I felt. I had a choice to make, and I didn't plan to rush it. I felt like I suddenly held all the aces in my hand.

"What do you mean, I'm not married? We're going to change that soon. You're the love of my life, like I am yours. You have proposed to me and I've accepted. Yes, my job isn't as well paid as yours, but we had agreed that I'd be a stay-at-home mom anyway."

"You seem to assume that I still plan to marry you." Her look told me that she had the same doubts, but wanted to whitewash it with her fake cheeriness.

"What? What are you talking about? Of course, you're going to marry me, doofus." She advanced on me, clearly wanting to kiss, cuddle or whatever. The palm of my hand stopped her quickly.

"Why should I? I'm not saying I won't, but it's not an easy decision. I'm pondering the pros and cons. I proposed to you once, but you've added a lot of baggage since. Emotionally and physically." I pointed at her belly.

Dread started to show on her pretty face as the reality of her situation started to sink in. She would have to convince me to go ahead with the life she had planned, and she needed to come up with some good reasons, fast. She had no plan B; if I refused to marry her, she would have nothing. We both realized what a terrible risk she had taken by getting knocked up by some idiot while needing me to take care of her. Especially as that idiot had somehow experienced some unfortunate occurrences recently and was unwilling to return anyway, but she didn't know that.

stev2244
stev2244
1,935 Followers
12