Tonys Ascent Into Cuckolding Ch 03

She called Brad that evening to let him know that I had come around after some convincing. They chatted for a while, during which she told him about my misbehavior. She moved away from me and talked softly for a while from the other room. Finally, she came back to me. I heard her saying, "Do you promise? You'll do that for me?" Then she listened for a while as her smile grew wider. "Ok, thanks Brad. I'm feeling so wet and wild just thinking about how you're going to take charge of the situation on Friday. Let me give it to him." I had no idea what she was talking about, but she turned to me and said, "Brad would like to have a word with you."

I hesitated to take the phone. She gave me a stern look and shoved the phone towards me. I took the phone nervously as she sat back with a wicked smile.

"Hello, Brad," I said softly, despising him.

I listened to him as he coached me. "Tony, please trust me that you will grow to love this arrangement. I know your cuckold psyche well. You will enjoy it and thank me one day."

"Yeah, sure, I'm sure I'll see the light one day," I answered sarcastically.

"I hear the hesitation in your voice, but that's normal. You will need a good 6 months to adjust to being dominated by Linda and me as a cuckold, but then you will appreciate it."

I thought I heard him say 6 months, which struck me as a long time. I was hoping I misunderstood him. "Ok, thanks," I said softly.

"Tony, I heard some complaints about your attitude today." I paused for a while, not sure what to say. "Tony, did you hear me?" he demanded.

"Yes, I heard you."

"Well you need to acknowledge when I speak to you. I want us to start off our relationship on the right note. Linda is your mistress in charge, I am her bull, and you are the cuck. That means her role is to gives the orders and makes the decisions, my role is to be her man and please her, and your role is to serve us. You will take orders from both of us."

"Yes, I understand," I said.

"Good. Now, did Linda explain to you that you are going to get your first spanking from me on Friday?"

It was notable that he called it the 'first' spanking, as if he expected there would be more. "Yeah, she did."

"I'm sorry we have to start the relationship this way, but I have to establish my authority over you firmly from the start. You understand the role that corporal punishment is going to play in your life, right?"

"Well, she didn't mention anything about an on-going role. It was a spur of the moment thing."

"Wrong. Tony, as part of establishing my dominant bull alpha presence, I will have to periodically discipline you. You may not like it, but it's a necessary part of how I win over your wife."

"She said that?"

"She didn't have to say it explicitly Tony. Real men don't ask. I told her that I would beat your sissy ass to keep you in line. And you know what she said? She smiled and told me that her pussy was salivating."

"Ok, ok, I get it. But may I make a request?"

"Maybe, what is it?"

"I'm going to get spanked the day before my Linda already, so my buttocks are going to be quite tender. Could you go light on me this first time?" He laughed at the other end as my face turned red.

"Ask again, and say 'please' and 'Sir' when you speak to me."

I paused, and then replied, "Sir, could you go easy on me please?"

"Well, Tony, I see your dilemma. How about I make you a deal? Linda has asked me to give you 50 strokes. But I'll go a bit easier on you. You can wear your wife's panties (whatever she's wearing at the time - she'll take off and let you wear them for extra padding. Also, I'll give you 5 less if you submit to the punishment in a cooperative manner when I tie you down. I'll reduce it by another 5 if after every stroke, you say out loud, 'Thank you Sir - I've been a naughty sissy cuck. Please spank me again, SIR!' You'll have to say this loudly and respectfully - Linda will be judging whether you say it well. If she doesn't approve, we'll repeat that stroke. If you agree to both of these things, and if she counts all of the strokes, you'll get only 40 and you'll have the protection of your wife's knickers."

"Thank you Sir," I said feeling even more embarrassed at how dependent I was on my wife's good graces.

"Ok, I hope you feel better now. I also want you to know that after you get paddled by me, Linda is gonna send you to stand in the corner, wearing a little skirt and bra, with your frilly panties pulled down. You'll have to hold your skirt up so we can admire your blistered bottom. She'll take some of her soiled panties out of the hamper and pull them over your head so you can hide any crying and whimpering with some privacy."

"Ok. Good that we cleared that up. Next thing is that I want all of your stuff out of the master bedroom by the time I arrive on Thursday, and I mean everything. I don't want to see any trace of your stuff there. Got it?"

"Yes Sir," I replied.

"Also make some time this week to buy some appropriate clothes for yourself - Linda will know what I mean. See you soon." He hung up.

I put the phone down. Linda beamed up at me with a big smile from the bed. She was dressed in a sleek black negligee. I hopped into bed.

"Honey, did Brad make you a deal?"

"Yes, he did." I was in no mood to humiliate myself. I was hoping to put the spanking out of my mind and try to get it on with my wife, knowing that I was going to be sentenced to chastity soon.

"Well, tell me what it was? What's the deal?" I did not want to share it, but knew that it was inevitable that she would find out soon enough.

"I'm going to get 10 fewer swats by cooperating with him and accepting the punishment, and by saying thank you and requesting another spanking. And he's also going to let me cover my buttocks."

"Or really? Not a bare bottom spanking like the one I'll be giving you?"

"No, he's going to allow me to wear your panties for protection." She giggled on hearing this.

"Oh, that's so sweet of him! As if my delicate little panties will make much difference..you're already scared, aren't you, honey?" I wanted to change the subject.

"Darling, wife, I would like to make love to you tonight," I said.

"And I would love it too. Let's make it something special to remember," she whispered softly.

I rolled up on top of her, my dick hard and erect, all 5 inches of it. She lubed herself. I sank into her sweet pussy, and lay down on top of her. Closing my eyes, I felt her breasts against my chest, her perfumed hair against my face. I began to rock back and forth. She moaned slightly. I moved my hips in and out feeling the warmth and tightness of her vagina against my cock.

"Just think about what you'll be missing," she whispered. "You better enjoy this while you can. You won't be allowed here."

"Please stop, Linda," I begged.

"You don't want to have sex with me?" she teased.

"No, you know what I mean..." I said. She started to move her hips vigorously. Her muscles tightened up all around my cock. She knew just how to milk me.

"Tony, I hope you're going to last long enough to make me come? Go in all the way, would you?"

"I am in all the way," I replied.

"Oh, ok," she said, "I'm sorry. I won't have to worry about that with Brad. His cock reaches deep into me, over 8 inches, and thick too," she added.

"Please don't talk about Brad right now," I demanded.

"Awww...are you all conscious about the size of your little boy penis? I'm sorry - I didn't mean to hurt your pride." Her teasing was perversely turning me on.

"Tony, I think your pricklet is getting harder. Baby, don't come yet. Can you fuck me long and hard, like a real man? Come on Tony!! Fuck me baby. Fuck me!" I felt an orgasm brewing up inside me. I wanted to hold back, but her vigorous milking was winning me over. She looked into my eyes with a wicked smile, "Tony, this is it. What you've been wanting." She kissed me.

"Starting tomorrow, your little wiener's going to go to prison for a long time. You've been a very, very naughty little sissy boy. You know in prison, little sissies like you get spanked hard. It's going to be a long time until you'll be allowed to cum. Brad will not allow you any conjugal visits with me. It's a good thing that Brad will be here in our bed to take your place and fuck me every night, huh?"

At that moment, I came in a throbbing orgasm, a heavenly feeling, one that I would miss dearly in the coming weeks and months.

The next morning, I woke up to the sensation of coldness between my legs. I peered up and noticed Linda holding an ice pack against my penis. "What are you doing?" I asked. "It's 6 AM! Why are you up so early?" I shoved it off and got up from the bed.

"Tony, it's a workday, remember? Also, it's Wednesday, so this marks the beginning of your prison sentence." She told me lie down face up on the bed naked, with my legs spread apart. She tied each ankle to the corners of the bed frame, and then my wrists to the other side. She wiped my penis and balls with a warm cloth, then squeezed a generous amount of lotion onto my penis. She rubbed it into me as I got aroused.

"Now, now, don't get excited." She slapped the ice bag back onto my cock and applied firm pressure as I calmed down. I shivered as my penis and balls shrank down. Little by little, she managed to pull the rings of chastity belt behind my testicles, then put the shaft of the chastity belt over my penis. I looked off to the side as she manipulated my genitals into the device. The final pin was in place. She held the contraption together with her hands, and flashed the tiny metal padlock in front of my eyes. After putting the lock through the hole, she clicked it shut, tugging at it to make sure it was secure. "Tony, congratulations! You are officially in chastity prison. Today is day 1 of your 60 day sentence. You will find a list of rules that you need to learn in your e-mail. Brad and I want to remind you that you must obey all of the rules without any exception. Then, at our discretion, you may be released earlier for exceptionally good behavior. But just to manage expectations, darling, that probably won't happen."

"Wow, that's really harsh, Linda. You know I've never been locked up for more than a few days."

"Well, this time it's going to be a lot longer. And the 60 days is just a guideline. If there's any bad behavior, even the slightest infraction, the judge may impose additional imprisonment, beyond the 2 months. Got it?"

"Yes, I understand. Are you the judge? Or Brad?" I hoped to God it was not up to him.

"I am the one and only judge. I will hear comments from both you and Brad, but the final decision about your chastity belt imprisonment will be mine."

"I'll have a say?" I was relieved to know that my opinion would count, and that I'd be given an opportunity to lobby for my release.

"Yes, but only a small say. I already know what your opinion will be, so I'll most likely discount anything you ask for. I will, however, have to take Brad's opinion into account. If he objects to you being released early, and if he has a good reason, I probably won't release you. And if he feels that we need to keep you locked up longer, I'll certainly have to take it under advisement."

"What do you mean? I thought you said it's your decision only?" I objected.

"It is my decision, but he can influence it. Look, if he has a good reason for extending your sentence, I will have to hear him out and consider the merits of his request. It's important that we have some mechanism to ensure that you have an incentive to behave around him."

"So what kind of reasons would you consider for releasing me early or lengthening the chastity time?"

"Well, for me, if you showed exceptional cuckold obedience and did everything to please me and show genuine acceptance of your new lifestyle, then early release could happen. But if you whine, complain, or show lack of commitment, then I could just as well extend the punishment."

"And how about for Brad?"

"Brad's situation is similar, but you'll have to ask him. I think he would be supportive of early release if you show complete submission to his authority and readiness to commit to being a respectful cuck. On the other hand, if he senses any ego, competitiveness, disrespect, disobedience, resistance, or attitude, he'll probably want you to be punished longer."

"Linda, I don't like this at all. You say that it's your decision only, but then you're taking input from him on all these things. He's bound to find a reason to keep me locked away!"

"Tony, honey, you're not listening. I told you that it would be my decision, but you don't seem to believe me!" she snapped.

"I'd like to believe you, but you're not consistent in what you're saying."

"You over-think everything and you're driving me nuts! How about this for consistency? I'm changing the rules. It WILL be both Brad and my decision. You'll be released ONLY after BOTH of us approve. Now do you feel better?"

"No, darling, please. That's not what I meant. I just didn't want him to have so much power over me."

"Well, too bad, isn't it? You wanted consistency. Now you have consistency! Thanks to your own whining, instead of him just influencing my opinion on the matter, we will both hold the power of deciding when to release you. If he agrees, but I don't, then you'll stay locked up. If I agree, but he doesn't, you'll stay locked up."