Best Cuckold Story

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Really Good Story Found on Literotica.com
I found this a few days ago on Literotica.com. In my humble opinion, it's one of best cuckold stories I've read in years (can't wait for the author to carry it forward).

Tony's Ascent Into Cuckolding
by Cuckyboy3

Linda looked at me lovingly, holding both hands and sitting me down gently. She had that look in her eye that told me she had something difficult to say to me, something I would not like. I sat down with a resigned sigh and waited. She affirmed her long-term and undying love for me for several minutes. Finally I could not stand it any longer and simply asked her, "Linda? Is there something you need to tell me?"

She realized that she had been setting me up for a purpose. She pulled herself forward in her chair, paused a moment, and then looked down at the floor. "Tony, this is unbelievably difficult for me to do, so I'm going to ask you to support me. Can you promise me?"

I smiled to myself, marveling at the power I held at this moment in the conversation. "How can I promise you? You haven't told me what it is!" I observed.

She looked away for a minute to collect her thoughts. "Tony, let me clarify what I meant. I'm not asking you about the thing itself. Brad and I have talked at length over these months, and I've made some decisions that I think are in everyone's best interests. I'm just asking you to support me, unconditionally, okay?"

"So you're not asking for my permission," I concluded.

"No. I'm not. Look, I know this is hard, Tony. This may sound cold and cruel. I'm not asking for your permission, and in fact, I'm not even asking for your opinion on the matter. I just need to know that I can count on you."

"Well then there's really not much to talk about, is there? You haven't told me a damn thing about what might be in my best interest or not!" I said as I got up, suddenly feeling miffed.

Linda reacted immediately and firmly. "Sit your ass down, Tony! I will tell you everything you need to know, eventually. Right now, I just want an assurance that you'll keep an open mind – that's all. Do this for me, okay?"

I sat silently. I wanted to cooperate, but I had no idea what she had in mind. She had been dating Brad about a dozen times over the last 4 months, and had steadily heated up the relationship from casual lunch and dinner dates to dancing at clubs, and then to more intimate evenings at his place. Where was she going with it I wondered.

She looked dismayed, realizing that I was not ready to commit. "Fine, it's okay. Let's talk about it later." She got up and walked away, clearly upset about my reaction.

I could not let it end like this, and immediately followed her. "Please, Linda, I want to help but I just need to know--".

She cut me off, "No, Tony. I should not have brought this up right now. Brad was right that this would not go over well with you. Let's talk about it another day when you have a better attitude."

"Fuck that! You can't just leave me hanging like this Linda. I want you to tell me what you have in mind!"

"There's no need to. Remember that when we started this, you agreed that you were surrendering to me?"

"Yes."

"Well that's what you're going to do," she said as she stroked my cock through my jeans. "You're going to submit - you just don't know it yet."

I was insulted by her presumptuous tone. "So, then why did you even bother asking me?" I demanded.

"I asked you because I wanted your yes to come from you, so you could be a willing partner in our mutual fantasy."

She sounded sincere, and I realized the truth of what she was saying. The fantasy was initially inspired by me, and now we both shared it. It was only natural for me to be supportive, and for her to be insistent.

"Okay, I promise to support you," I replied in resignation.

"Are you sure you're ready?"

"Yes, I agree. Whatever you've decided, I will agree to and be supportive, unconditionally and completely."

Linda looked at me straight in the eyes, and with a faint smile, she explained, "All right then - Brad is going to move in with us." She said it confidently and firmly.

I turned red in the face in shame that she would not even consult me on such an important matter. "What do you mean he's moving in with us? When? How would this work? What if I don't like it?" I asked.

"Tony, honey - please calm down. I asked myself all of these questions too. Brad explained to me that there would have to be a series of adjustments over time. At first you will probably feel angry and rejected - that's normal. Then you will come to accept it and cooperate. In the final stage, you will understand that it's actually for your own good, and then you too will welcome it happily. I'm looking at the long-term picture. You have to trust me on this!" I looked away, unable to confront her on this, realizing that she had put in a great deal of thought into the matter already.

"Linda, how the hell would Brad know? He's not the one whose life is being turned upside down?"

"Brad knows what he is talking about." She unzipped my pants and wriggled her hands inside my boxers to pull my penis out. "Admit it. You want to submit to me!" My cock started growing harder. "Isn't that right? That's why your little dicklet is getting so excited, isn't it? Your own cock is hard as a rock so it's clear that part of you agrees with him. You need to come to terms with your inner self, honey."

She continued, "For now, he's moving in only for extended weekends."

"What? Is this something you two are just considering? Because it doesn't sound like it. It sounds to me like it's already been planned."

"It has been decided and planned. He's taking some time off from work to move in. Starting this week, he will come over on Thursday nights, and stay through Sunday evenings – 3 nights."

"For entire weekends? But that'll totally change our lifestyles!"

"Well, uh, yes...I certainly hope so!" she giggled.

"Very funny," I muttered. "So what now? The two of you will do your thing in our home. That's the last thing I imagined when we bought a house with a guest room. Look, Linda, I know this whole cuckold thing excites me too, but can I just have a little time to think things through? I didn't think I would be locked out of the decision process and that things would move this fast."

"I understand how your head must feel confused, but you really don't need time to think about anything. Your penis has made it very clear that he approves. Tony, you'll have to get used to being locked out, figuratively with certain decisions, and sometimes literally too."

"What do you mean, literally?"

"We will lock the door when we need our privacy. That's all I meant."

"But there's no lock on the guest room--", I objected.

"Well, of course, Brad and I will s_l_e_e_p in our master bed room, so YOU will need to move your stuff to the guest room."

I was utterly devastated to hear how the two of them would be sharing my marital bed. I felt a sinking feeling in my gut, envisioning another guy in my bed, underneath the covers with my wife. She stood next to me, with her hair d_r_a_p_i_n_g down and eyes gleaming, looking more seductively beautiful than ever.

"Stop...I think I've heard enough. I can't believe how far you've planned out all this without even telling me!"

"Yes, it took a while to figure everything out. Other more subtle changes will fall into place. I can't tell you all that right now. Right now, I need to know that you're going to support me in all of this. Happily." I sat glumly. "Tony, you know this is what you want...deep down inside." She stroked my cock again as it grew even more erect. I felt a surge of erotic energy as she continued to tease me. "Tony, you know that I need a real man in this house to make me experience the joy of being a woman." My cock throbbed. "You'll have to channel your jealousy into something productive while he's fucking me in our bed." I tightened my pelvic muscles to avoid having an orgasm.

"There's gonna be a whole lotta sex happening in this house from now on, but not for you."

"No, I don't think so," I lied to myself as my own penis grew more excited.

Linda responded by stroking my cock faster, "Tony, you can't hide your true feelings. If you keep lying to me, I may have to use the paddle on you." She was speaking f_o_r_c_e_f_u_l_l_y and looking straight into my eyes. "Would you prefer to get a spanking?" I shook my head 'no'. "If I have to Tony, believe me, for your own good, I'll tie you down and blister your cheeks until you tell the truth." At that moment, I came all over in my underwear as she stroked me vigorously, validating what she was saying all along.
Later on, Linda told me the additional things she had decided. "I'm going to get my hair cut short."

"Did Brad ask you to do that?"

"Yes. I know you like my hair long, and it will grow back. But right now, I'm cutting it to just to please him."

"We'll also have to go to the mall tomorrow to expand your wardrobe of fem attire so that you can be dressed appropriately whenever Brad is present."

My mind was spinning as she dropped all this on me. "Of course. You want to make sure I don't run out of panties and skirts." I snapped back, having anticipated this already.

"Yes, actually, Brad and I agreed that if you're going to play the sissy role well, you may as well go the whole way. So we're going to get you some satin camisoles for lounging around, babydolls and slips for s_l_e_e_p_i_n_g, bikinis, bras and halter tops for added fun, and stockings to cover your legs!! " I turned red all over my face in shame, but before I could even react, she added fuel to the fire. "And one more thing," she added, "I'm not going to use condoms any more with him."

"What?" I exclaimed, "Why not?"

"It's okay. We've gone through months of stable relationship building. We're ready for this commitment now."

"What's wrong with continuing to use protection? Please!"

"Tony, it's not your place anymore to tell me what to do."

"I'm just trying to understand why. Is that so hard?"

"You really want to know? I just want to feel his raw dick inside me – it's as simple as that. I want to feel his meaty cock ravage me and pound me deep and hard. I want to feel that hot semen shooting up inside of me, and then the slick feeling of it dripping into my panties and down my legs for hours afterwards."

"Holy smokes, Linda...you're insatiable! You were never this graphically sexual in your desires with me. Where's the energy coming from?"

"It's thanks to Brad and you. Brad because he just turns me on so badly...he's got that manly man thing that drives me wild. And you, because you'll be taking care of everything else so I can focus on him. You'll be responsible for grocery shopping, cooking, laundry, ironing, house cleaning, and washing dishes from now on."

"Sounds like I have to do all the work! Are you going to do anything around the house?" I barked back.

Linda looked at me firmly, "Husband, you're going have to stop the attitude when you speak to me. I am your superior."

"It was just a simple question!" I said with an exasperated and blaming tone of voice. She stopped and stared at me without a word. The seriousness in her expression made it clear that I had crossed the line.

"You know what? You've just earned yourself a double spanking for this, once for asking a disrespectful question, and the second one for the bad attitude that you said it with!"

"I'm sorry," I replied.

"You will be more sorry on Thursday night after the paddling, and then really painfully sorry after Friday's paddling."

"I'm really sorry, honey. Listen, may I please request that you do the spankings today and tomorrow? Before Brad gets here? I don't want him to see or hear me getting spanked by you." I said.

"No, we're going to stay with Thursday and Friday. It'll give you some time to dwell on the impending punishment. As for Brad, he knows already that I periodically use the paddle to punish you. And as for him witnessing it, it's not a problem. In fact, how about if I ask him to do the honors on Friday and administer the paddling himself!"

I was horrified. "No, Linda, please! Please don't. I'll already be sore from the day before!"

"I know you will...and after Brad finishes smacking your ass, you won't be able to sit down - I can promise you that. He'll whip your ass harder than I would, and he won't care that you'll already be sore from the day before. I know he wants to set the tone right from the start of this new relationship."

"Linda, why do you want to humiliate me like this in front of him?"

"Tony, you're going to get punished, just like you deserve. Whether it's humiliating or embarrassing or not is up to you. If you take it like a man, better for you to preserve your self-esteem." She looked at me with a mocking attitude, as if questioning my virility.

"Don't worry," I replied, "I can take it."

"Ok, sure you can?" she teased. "You know if you start whimpering during the spanking, it'll be too bad when he treats you like a sissy! But like I said, that's all up to you."

"I'm not going to cry!!" I objected. She looked at me skeptically.

"Tony, I didn't even say anything about crying. I said 'whimper'. But it looks like you're scared you might start crying, aren't you? Oh, poor like Tony baby - you can certainly try not to cry. But if you can't help yourself, it's okay. I'll give you a tissue to wipe your little girly tears, all right?" She was gloating in my h_u_m_i_l_i_a_t_i_o_n before it even happened.

"Stop it! Like I said, I'm not going to cry."

"Ok, I'll stop. And by the way, do you really need to ask 'what am I going to do while I'm not doing housework?' Take a guess! It should be obvious. While you take over responsibility for all of the housework, I will have more time to hang out with Brad, and not just hang out, but also to fuck. We'll be having a lot of fun under the covers. Fucking several times a day, and night. That's why you have to do the work. Get it?"

"Yes, I understand. But Linda, what about us? When will we get to make love?"

"Well, that's an interesting question. I'll generally be too exhausted and sore on Sunday night, you know, from all the sex, of course. And then I need to be fresh and ready for Brad on Thursdays, which means I can't do anything with you for 48 hours before, so that eliminates Tuesday and Wednesday. So that leaves Monday for your window of opportunity."

"That's all? Once a week?"

"Yes, and that's if you behave well, and if you can manage to get an erection going with your pee wee penis...otherwise it could be less often. You should be thrilled that you have a window at all."

"Oh, and by the way, I almost forgot to mention something very important. You will have to get Brad's and my permission to have sex with me while he's gone. That means you will have to please us and be on your best behavior all weekend. Before he leaves on Sunday night, you will have to request his permission. If, and only if he approves, then I'll have to also think about it and will let you know on Mondays."

"What if one of you will always say no?" I cried.

Linda embraced me closely, putting her head against my chest. She whispered to me lovingly, "He won't always say no. He is a possessive alpha male type, so he may well deny you, in which case, you'll just have to live with it like a cuckold should. But he's really a nice man, and after getting laid all weekend, I expect he may sometimes be in a giving mood. And if he approves, then I will probably give also. I do love you after all, and you are my husband!"

I sighed in desperation, "Ok, I hope so." I paced back and forth, feeling a bit lost. Linda headed towards the kitchen to prepare dinner. Then she turned around with an expression of sudden surprise.

"Oh, wait. Hold on. Actually, there is one correction come to think of it." She gave me a firm look straight in my eyes. "All of this business about Monday sex for you won't happen right away. I forgot to mention that there will be an initial break-in period where Brad and I will be exclusive. No sex for you."

"No sex? Holy s_h_i_t! What else did you fucking forget to tell me?" I was feeling angry now.

"That's right. No sexual action at all. Not even a blow job, no hand jobs, no masturbating...nothing."

"But what about when he's not here?"

"Didn't you hear me? No sex at all for you, even when he's not here. If fact, you'll be caged in chastity so that you can focus on learning how to please us."

"And how long do you two propose this would go?"

"Look, I'm not proposing - I'm telling you. Get that through your head. Brad and I will have to finalize the length of your chastity belting. Initially I was thinking just a month, but he feels you may need a good 3 months of abstinence while he and I establish a healthy relationship with each other."

"A healthy relationship?" I thought to myself. I sat down to absorb all this. My head felt dizzy.

"Tony, remember that this is all for your own good in the long-term. I read up on this and I'm confident that it will work. For your health, we'll remove the chastity belt for cleaning every week, and we'll release the pressure on your balls every two weeks through prostrate massage."

"Please, don't humiliate me by inserting anything up my ass! I can just release the built-up semen during the weekly cleaning by jacking off."

"No, Tony, sorry. You won't be allowed that pleasure. The reason for the prostrate massage approach is to drain the cum out of you without an orgasm. You won't be allowed to touch your penis at all. It'll simply twitch and the semen will dribble without the pleasurable orgasmic sensations. We'll do it just before washing you up so that you don't accidentally ejaculate. That would be a shame, because then I would have to add a week to your chastity time."

"Oh, damn! This is going to be so hard. I don't know if I can do it. How can you expect for me to not touch my own penis and let it just go down the drain without an ejaculation? It's just not fair!"

"It will be sweet t_o_r_t_u_r_e I promise, but you'll enjoy it. We'll actually capture your spunk in a little cup."

"May I ask why?"

"I know this may seem a bit gross, but you will have to eat your ejaculated semen after being milked."

"You're kidding. Please tell me that you're kidding."

"No, for real. Brad and I want to train you to get used to the taste and texture of semen." We stared at each other. I suspected there was more to it, but she wouldn't say anymore, and I just wanted to change the subject. I excused myself to go outside and be myself.

She knew she had pushed my buttons quite hard. I took the opportunity to mow the lawn and take my mind off of it. When I finished, I headed back in. Linda was preparing dinner, but did not turn to look at me. I went straight upstairs for the shower. That evening, we had a quiet dinner. She toyed with her food. I ate uncomfortably. Finally we broke the silence and start
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