Cuck shit

Story Info
Size queen wants to make fiancé her cuckold.
15.3k words
2.41
33.6k
46
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

This story is named in honor of some of my faithful readers. All the fictional people having imaginary sex would be over 18 years old if they were real. I hope you enyoy it.

"Cleopatra Sage Dwyre, will you please do me the honor of becoming my wife," I said kneeling on one knee and looking into her shocked eyes.

I had reserved a table at an exquisite restaurant not too far from my apartment. Lately I considered it OUR apartment even though Cleo had three months left on the lease of her studio. We have been dating for six months in what I considered a whirlwind romance.

We fell deeply in love in very short order. I was literally still learning about her family, likes and dislikes, and many of the things that make her who she is.

I have never felt like this about a woman. Sure I had my infatuated romances in high school and my horny, sex driven flings in college, but this was way more than any of that. Since I graduated and started working as a computer engineer, I haven't had time for dating that much. The few dates I had usually ended with sex and not much more.

Cleo came into my life unexpectedly. She was a salewoman for a company we had started dealing with at our company. The first time we spoke I was infatuated. She fit my "type" to perfection. She was about 5' 4" and thin, very light skin and hair with breasts on the smaller side of average and the cutest little ass you ever saw. But it was her personality that made the sale. She was friendly which isn't abnormal for a salesperson but it was genuine. She had a dry sense of humor just like I enjoyed. Her intelligence was at a level that made her intensely interesting. She also seemed to like me since she always stopped by my desk to talk.

Soon I realized I needed to do something about it. I asked her out on one of her visits and the rest is history. She has been staying at my apartment for about three months now. We are both pretty busy at work so our time together is a little limited.

----

The patrons at The Siam Orchid were watching and holding their breath. The slight hesitation seemed like an eternity, maybe just two heartbeats too long. Then, after looking away from me and seeing everyone that was watching she said, "Yes." It was a bit weak but she stood up as I did when the crowd cheered and kissed me then put me in a bear hug. I could see some sort of conflict on her face. Did she mean it when she said yes? It hadn't been the ecstatic reaction I had envisioned. She didn't even put the ring on.

My nerves were now creeping into my brain. I was wondering about all sorts of bad things that might happen and we hadn't even left the restaurant yet. We hadn't even said anything of substance to each other since that life changing moment.

I was afraid. I didn't know what to say next. 'Nice weather tonight?' Nope, that would be bad. 'You look beautiful tonight?' That would be great if I hadn't already said it twice before the proposal. I thought about waiting for her to say something but that could get extremely awkward.

We walked towards the car and I just decided to take a shot. "How are you feeling?" There, I put the ball in her court without being too confrontational. I waited. Again the delay was far too long to be okay. My heart sank. Something was wrong.

As she opened her mouth to say whatever it took her so long to think of, I interrupted with the real question I had. "Do you really want to marry me, or did you just say that in the restaurant so we wouldn't be embarrassed?"

"Noah," she got out at the beginning of her sobbing. "I'm sorry, this should have been a highlight of our lives but I fucked it all up, I'm sorry."

She was crying on my shoulder standing next to the car. I helped her into the passenger seat and I drove away not sure what was going on. It was silent for half the drive home. Cleo finally broke the silence.

"I do want to marry you," she said and began sobbing all over again.

"Buuuutt, you're already married to someone else?"

"No!!"

"You forgot to tell me you used to be a man?" This time I got a chuckle.

"No," she said in a softer voice. "I want to spend the rest of my life with you. I love you so much. You caught me off guard tonight, I wasn't expecting it."

"Babe, I know this is a little quick, but we can have a long engagement. I just want you to know my intentions. Still, even if it was a little too soon, I sense more of a problem than that. Am I wrong?"

"No, you're not wrong. Let's not start this conversation until we are sitting at the apartment, changed, comfortable, with a drink in our hands." I nodded.

The last 5 minutes of our trip seemed to take forever. We didn't speak but Cleo cried again. At home we both washed up and put on sleepwear. I poured a red wine for Cleo and grabbed one of my expensive beers out of the four pack. We sat at the kitchen table and I steeled myself for the coming conversation.

"Ok babe, you have the floor. What's on your mind?" I smiled one of those smiles that means 'I'm not so sure a smile is in order here.'

She wrung her hands with white knuckles. She couldn't make eye contact. She started to cry again so I took her hands in mine and said, "I will listen without judgement until you're done. Please babe, just spit it out."

She finally looked at my eyes, probably seeing worry in them. "Noah, you know I love you, don't you?" I nodded.

"When I met you I knew right away you were special. You turned out to be more than I could have ever hoped for. I had never met a man that was so close to perfect."

"I wasn't perfect though, was I?"

"Please babe, let me get through this. I wanted to have this conversation soon because I had a feeling you were going to propose before too long. I was scared and kept putting it off thinking you wouldn't propose this soon. Well, I was wrong. Babe, did you tell anyone you were going to do this?"

"No, I wanted to keep it a secret so I could surprise everyone at once. Besides, people get angry when some people know and others don't."

"Good, if you decide to retract your proposal we can just make believe we just broke up." I was shocked. Why would I want to do that? She saw the shock in my eyes and took my hands.

"Alright, let's get to the point. Before I met you I have had other boyfriends. Nobody all that special but boyfriends. In high school my only steady boyfriend was a basketball player named Jamal. Yes, he was black. He was a nice guy. His family hated me and my family didn't approve even though they never said it out loud. No big deal, it was to be expected. We were together for almost 6 months. He took my virginity when I turned eighteen. At the time I had never seen a penis before. I did know that I loved having his cock in me."

Cleo let out a long sigh, took a sip of wine, and took in another deep breath. She was starting to relax into the story.

"We broke up the middle of my senior year. Turns out he was a player and loved bangin white virgins. I was upset but he was never going to be THE ONE. The rest of my senior year became a whirlwind of sex with various partners. I had become known as a slut. I didn't mind since I was getting what I wanted and would never see those people again after graduation. I did learn one thing during my senior year. Every guy is different. Some are good at licking my pussy, some are gentle, some are rough, some have big cocks, some love to watch me swallow their cum, some like cumming on my face and tits. You get the point. For me one thing stood out that I liked. When I went to college I focused my dating on the one thing I liked. I searched and found myself having sex with ten different guys. I was addicted to the one attribute they all shared. Big cocks."

My spirit took a nose dive. My pride was hurt deeply. "Are you saying you don't want to marry me because my penis isn't big enough?" I know I looked hurt.

"No, no, no. Let me clarify. Your penis isn't small!! When we make love there is no place I'd rather be. You are wonderful and I want to spend the rest of my life as your wife."

"But..."

Cleo looked at her hands then into my eyes. "I have become accustomed to a life of getting fucked hard by big cocks. The last six months have been great and I was 100 percent faithful to you but I was at a point where I was ready to explode. I have a compulsive need for big cocks. You have to understand, I don't just like it as a quirk, I have to have it or I go through withdrawals. I become unhappy."

I looked at her questioningly, "So..."

"So I had never considered the idea of being monogamous until I met you. Now after six months I knew it could never work. Unless..."

"Unless I had a bigger cock?"

"Unless I could have my cake and eat it too."

"S-S-So you want to marry me and fuck other guys?" I was gobsmacked!

She looked down. She seemed defeated. "Babe, I know this sounds stupid, selfish, and straight up batshit crazy, but yes that's the gist of it. I can't imagine ever being happy without having those nights. I'm sorry I didn't bring it up sooner. Like I said, I was afraid. I still am. I don't want to lose you but you have to understand that this is a big part of who I am."

I was shocked. I imagined her in the arms of another man. "I don't know why this is my first question but how would I even know you wouldn't fall for this other guy."

She looked very serious. "I'm going to be very honest with you. First of all, it wouldn't be just one guy. One man can't keep me satisfied. I told you in college I had up to ten guys. I need at least 5 guys to keep me happy. I get bored with the same guy. Secondly, I don't have feelings for any of them. They just provide a service. I am actually friends with a few of the men but nothing more. I have more often disliked the men I fuck. It's the cock that matters, it has to be big, the bigger the better."

I sat stunned to silence for several minutes trying to digest all I had heard. What I hadn't heard is what the end result was supposed to be.

"So let me get this straight. Are you asking me to marry you and give you permission to fuck other guys?"

"In essence I'm telling you if you want to marry me this has to happen. I don't want to call it an ultimatum but unfortunately that's what it is. It will break my heart if you reject this plan but I don't think you want to be married to a very unhappy woman. You can end it right now or I recommend a trial period. This way we can be sure it works before committing to each other."

"So if I want you I have to submit to this lifestyle. Would I be allowed to sow my oats in other pastures?"

"Unfortunately babe this is a one way street. This is a must for me but for you it would just be cheating. I can't live with the thought of you with another woman. I know I'm a hypocrite but it's the only way I can do this."

"So a trial period? I don't know." I felt tears running down my cheeks. It felt like we just broke up.

Cleo cleared her throat. "I know this is asking too much of you. Why don't we sleep on it. We can talk more tomorrow. I'll sleep on the couch." I nodded and headed to bed.

It was a fitful night with little sleep but my mind is able to line things up nicely in the dark and in bed. It was the first night in a long time that Cleo wasn't in my arms. I hated it. By dawn I had more questions and my initial shock had finally worn off. I left the comfort of my bed, showered, and dressed for what I thought might be a long day.

I made coffee while Cleo shook the cobwebs from her head. She looked as unrested as I felt. She smiled and said, "Morning, how are you doing?"

I shook my head. "I don't know. Thank God it's Saturday, if I had to work I'd be useless."

"I feel awful. Do you have more questions? Have you come to any decisions?"

"I'm close. I do have questions. Let me start with this. Do you use protection?"

"I use birth control. I do not use condoms. Most of my men would refuse. I don't like them much myself. So as for STDs I am at risk, however, I have not had an STD since college. The men I have been with are pretty careful about that. They don't just fuck anyone."

"So there's a chance you could infect me? NICE!! What if we want kids? How do I know it will be mine?"

"Yes, then I will either abstain or use condoms until you get me pregnant."

"When you come home to me you will have another man's sperm inside you and your vagina will be stretched out, making my dick seem even smaller to you. That's a statement. How am I supposed to keep any modicum of pride. I will be a fucking cuckold." I was hurting now. The reality of the situation was hitting me.

Cleo shifted in her seat. She took a sip of her coffee then exhaled. "The flip side of my infidelity is that I would give you total control of the rest of our relationship. Sexually, I would give you anything you asked for and never turn you down. I'd essentially be your slave. I would cook, clean, pay the bills and you would automatically win every argument. You would be my boss in every way. If there was a date that interfered with something you wanted, I'd break the date. If you didn't like a certain man I would dump him. You would always be first no matter what."

I nodded my head. "Ok, Would you be telling me when you are having a 'date'?"

She looked thoughtful then said, "This is where you start to have more control. If you don't want to know, I'll just be discreet. If you do want to know, I will keep you informed with no secrets. If you want to know who I'm fucking, I'll tell you his name, where he works, anything you want. If you want to know where I'll be, I will give you the hotel and room number or his address. There doesn't have to be any secrets if you want it that way."

"I guess my biggest concern is whether I can handle sharing you. This is not how I pictured our marriage. I do love you Cleo but I'm not so sure this is going to work. I think I might be happier if we just end this now. A trial period would just be torture."

Cleo began bawling loudly. She certainly wasn't bluffing. This was a take it or leave it proposition. I asked for another day to think about it. This night I gave her the bed and I took the couch. I slept more but still got up very early on Sunday. Sleeping without Cleo brought me to one more question before I made my decision.

Over coffee I asked her, "Will you be sleeping with me every night?"

"If that's what will seal the deal, I would have no problem doing that."

"I don't like any of this, but I do love you too much to throw it away without trying. I hope you understand how hard this is for me. I will go through the trial period. However I don't want a time limit on the trial period. Also, as of now we are not engaged. I will have to ask you again for us to be engaged. Understand?"

She nodded her head half smiling for the win but seeming to understand that we aren't in a good place yet.

She meekly asked, "When should we start?"

I said, "You will come to bed with me tonight and blow my socks off. Then you will sleep in my arms. Then on Monday you should get started. I don't want to drag this out too long."

"Great, now do you want to know or should I try to be discreet?"

"No, I don't think I want to know when you're cheating on me. Be discreet, in fact be downright sneaky like I might catch you and murder both of you." I didn't smile.

Cleo looked concerned but continued, "I'm sorry about all this. I know you don't deserve to be treated like this. I hope you know it's not your fault, it's mine. I was already like this when you found me. This is the one thing I need to keep me happy. I don't need money, or status, or for you to remember my birthday, just this, your love and big cocks."

-------

As I mentioned earlier our work schedules are rigorous and often keep us apart too much. As the first week of work was ending I felt pretty good. There weren't any pangs of jealousy or bouts of anger. I also wasn't sure she had started her hookups yet.

The weekend was just getting started when Cleo let me know she was going out for a few hours on Saturday. I didn't know what to do. I didn't want to ask where she was going. She would either have to lie or tell me what I didn't want to know. Instead I grunted and turned away almost angrily.

On Saturday Cleo left late morning with a bag over her shoulder. She gave me a peck on the cheek and I thought she blushed, or it could be my imagination. I could have done many things to keep my mind off of it. The laundry needed to be done but I remembered her saying something about being my slave. I could watch the Sox game, so that's what I did. I drank beer and watched the game. But it's baseball, it barely holds my attention. Instead I was thinking about Cleo. Cleo getting fucked by a big cock.

I felt sorry for myself but I also fantasized about Cleo and what she was experiencing. To kill some time I figured I could masterbate since I was alone. Why waste a little alone time. I cast some porn to my TV and found a girl that looked like Cleo getting pounded. I had a very nice ejaculation. Then I was back to wondering where she was, who she was with, what was happening.

Finally, the few hours were up and Cleo had returned home. The awkward moment of her doing the walk of shame had arrived. But she didn't look guilty or ashamed. She just looked like her usual self, even smiling. I wasn't sure how I was going to handle the residual sperm. Would I ever want to lick her pussy again?

"Hi Babe, how was your time out of the house," I asked awkwardly with a cringe on my face after stumbling through the question.

She had a perplexed look on her face for a second and then it looked like a light went on. "Oohh yes, my trip to the gym was excellent. What did you do while I was out?"

She looked past me to the side table next to me where a used tissue layed. "Are you coming down with a cold?" she said smiling crookedly.

I'm sure I turned red. Before I could form a response she was halfway up the stairs so I just left it. For the rest of the week I was anxious every time Cleo wasn't home with me. It was eating me alive when she texted Friday to let me know she would be working late. I had a crockpot dinner made that could go on warm until she got home.

She finally walked in the door at 8:30 looking exhausted. I had been going through the same anxiety and using some therapeutic release methods to help keep me calm. I also carefully crafted my greeting so I didn't sound like a moron this time.

"Oh honey, you look tired. I have dinner ready and I'll pour you a wine while you're getting cleaned up." It sounded better in my head, well fuck it. When we finally sat down to eat together I let Cleo know about a decision I had made.

"Babe, I've decided that not knowing is going to kill me. I'm not sure knowing will be better or worse but the status quo isn't working for me. I want you to tell me when your dates are. If I can't handle that I'm afraid we're through."

Cleo looked horrified. A very long minute passed before she answered.

"I understand why not knowing would be difficult. I can't believe you're so ready to call it quits. Please just try for me, Please!!"

"I am trying. I'm trying hard. I told you this might never work. Please tell me now if you were on a date tonight or any time in the last week. I just need to know."

"I haven't been on a date yet. All I've done so far is make some phone calls. These guys were on hold for 6 months. Getting them back and scheduling takes some coordination. I can tell you I have one date set for this Sunday evening." Cleo stopped to watch my reaction and I assume she was waiting for a fight.

"Thank you, now at least I can relax until then. I have another request that just crossed my mind though. I want my own, cast in stone, bona fide date night just for me. One night every week that I can count on having you to myself."