Tim in training
Walking in on Gavin and Jason in a scene that surprised me, to put it mildly, and then being treated as a cuck was something I didn’t know I wanted or needed; it was something unexpected. I hadn’t experienced anything like that before. I have to admit I was excited as hell being there as a spectator and then being used to clean them up, it was hot as fuck, and my cock was rock hard through the whole scene. When Jason suggested that he and Gavin continue the night as a date, my cock just pulsed; it felt right. I was just there to serve their needs. When Jason suggested it, I know this sounds strange, but a warm feeling of happiness came over me.
The following weeks were a bit of a blur. We were all busy with our work lives. Jason had a few more large clients, which meant they were working a bit later, although they frequently worked at either Jason’s or our place now. At least I saw a bit more of Gavin than I used to when he first got his promotion.
One evening, I was at home alone reading when Jason's car pulled into our driveway. I glanced at the clock - it was only 7 PM, much earlier than usual. Through the window, I watched him get out of his car, but Gavin wasn't with him. My stomach did a little flip as I wondered what this meant.
The front door opened without a knock - Jason had his own key now, something that had happened gradually without any formal discussion. He walked into the living room wearing his usual confident smile, but there was something different in his eyes tonight.
"Where's Gavin?" I asked, setting down my book.
"Working late at the office. Real work this time," Jason replied with a chuckle. "The Henderson account needed some emergency damage control."
I nodded, unsure why he was here without my husband. Jason moved to the couch and sat down beside me, closer than I would have expected for a casual conversation.
"I wanted to spend some time with you," Jason said, his hand coming to rest on my thigh. "Just us."
My breath caught in my throat. In all the weeks since our arrangement had begun, Jason had never sought me out alone. It was always about him and Gavin, with me as an observer or participant when they decided I could join in.
"Why?" I asked, my voice barely above a whisper.
Jason's thumb traced small circles on my leg through my jeans. "Because I think we need to establish some things between us. Some... boundaries and expectations."
I shifted uncomfortably, both from his touch and the weight of his words. "What kind of expectations?"
"Well," Jason said, leaning back against the couch cushions but keeping his hand on my thigh, "you've been very good at playing a submissive role. You’re a natural at it, actually. But I think you need more training.
My heart started racing at the word "training." The way Jason said it, with such casual authority, made my cock twitch in my jeans despite my nervousness.
"Training?" I echoed, trying to keep my voice steady.
Jason's hand moved higher on my thigh, his fingers now dangerously close to my growing erection. "Tim, you have so much potential. The way you responded that night when I told you not to touch yourself, the way you served us dinner... it was beautiful. But you're holding back."
I swallowed hard, my mouth suddenly dry. "I don't understand what you mean."
"Yes, you do," Jason said firmly, his dark eyes boring into mine. "You know exactly what I mean. You like the idea of submitting, I think you want to submit completely, don't you? Not just watch from the sidelines, but truly serve both Gavin and me."
The words hit me like a punch in the gut because deep down I knew that there was some truth in what he was saying. Deep down, I knew that the feeling of just letting go and serving Gavin and Jason was something that felt right. It was exciting and scary at the same time, not knowing what was going to happen next. I wasn’t sure what it would look like to take this further.
"I..." I started, then stopped, my cheeks burning. Jason's hand was now directly over my hardening cock, applying just enough pressure to make me gasp.
"There's no shame in it, Tim," Jason said, his voice dropping to that commanding tone that made my knees weak. "Some men are meant to lead, and some are meant to serve. You've found your calling."
I looked down at his large hand covering my crotch, then back up to his intense gaze. "What would this training involve?"
Jason's smile was predatory. "First, we need to work on your obedience. You're still thinking too much, questioning instead of simply accepting." His fingers squeezed slightly, making me moan despite myself. "Stand up."
The command was simple, direct. I found myself obeying before I could think about it, rising from the couch on shaky legs. “Take off your clothes,” Jason said.
I hesitated for just a moment, then began unbuttoning my shirt. My fingers trembled slightly as I worked down the row of buttons, feeling Jason's eyes on me the entire time. I slipped the shirt off my shoulders and let it fall to the floor.
"Continue," Jason said, his voice low and commanding.
I kicked off my shoes and socks, then unbuckled my belt. The metallic clink seemed unnaturally loud in the quiet room. I unzipped my jeans and pushed them down my legs, stepping out of them awkwardly. Now I stood in just my boxer briefs, my erection straining against the fabric.
"Everything," Jason reminded me.
Taking a deep breath, I hooked my thumbs under the waistband and pushed my underwear down, my cock springing free. I stood naked before him, fighting the urge to cover myself.
Now stand with your legs apart and hands behind your back. This is how you are to stand anytime we are training or you are playing a submissive role.
Jason leaned forward and held my cock. Part of the training, he told me, will be to lock your cock up so you won’t be distracted.
"Lock it up?" I repeated, my voice cracking slightly.
Jason reached into his pocket and pulled out a small plastic device—a chastity cage. My eyes widened as he held it up, the clear plastic catching the light.
"This will help you focus on your true purpose," Jason explained, his fingers still wrapped around my shaft. "When you're not thinking about your own pleasure, you'll be amazed at how much more attentive you become to ours."
I stared at the device, a mixture of fear and unexpected arousal coursing through me. "Does Gavin know about this?"
"He will," Jason said, his thumb circling the head of my cock, collecting the precum that had formed. "But this is between us right now. This is about you and me establishing our dynamic."
He stood up, towering over me, and used his free hand to tilt my chin up. He leaned in to kiss me.
His lips were firm against mine, demanding rather than asking. I found myself responding instinctively, opening my mouth to let his tongue explore. The kiss was different from the passionate encounters we'd had during our threesomes—this was about dominance, about him claiming something from me.
When he pulled back, I was breathless. "Good," he murmured, his hand still stroking my cock slowly. "You're learning not to overthink." He went to the kitchen and brought back some ice in a tea towel.
He told me to wrap the tea towel with ice around my cock. My erection shrank instantly. I watched in fascination and terror as he began fitting the cage around my cock. The plastic was cool against my skin, and I had to bite my lip to keep from protesting as he worked my softening cock into the confining device.
"This might be uncomfortable at first," Jason said. "But you'll adjust. The important thing is that your pleasure is no longer your concern. Your focus will be on Gavin and me.
The plastic tightened around my flaccid member as Jason locked the device with a small key. A shiver ran through me—partly from the cold, partly from the realization of what I'd just allowed to happen.
"There," Jason said, his voice warm with approval. "Perfect."
He stood up and pocketed the key, then ran his hand appreciatively down my naked chest. I felt utterly vulnerable, completely at his mercy. My cock already strained against its plastic prison, uncomfortable but impossible to ignore.
I wasn’t sure I was 100% comfortable with this. How am I meant to hide this from Gavin? I said. Tim, from what Gavin tells me, you only have sex a couple of times a week at the moment, just think of an excuse if he wants sex, Jason replied.
"How long will I have it on for?" I managed to ask.
"That depends on you," Jason replied, circling me slowly. "On how well you take to your training."
His hand caressed my ass, fingers tracing the cleft between my cheeks. I trembled at his touch, unsure whether to lean into it or pull away.
"Gavin's always been too gentle with you," he said, It’s time for you to pick up your game.
"You need to learn to take what he gives you without complaint. No more wincing when he goes deep, no more gagging when he's trying to get down your throat."
His fingers pressed more insistently against my hole, and I gasped. "That's what tonight is about, Tim. Teaching you how to properly serve a man."
I felt my face burn with shame and arousal. The cage around my cock was already becoming uncomfortable as I tried to harden, the plastic biting into my flesh.
"Get on your knees," Jason commanded, stepping back.
I sank down without hesitation, the carpet rough against my bare skin. From this position, Jason looked even more imposing, his muscular frame towering over me.
He began unbuckling his belt, the leather sliding through the loops with a soft whisper. "Open your mouth," he said as he freed his thick cock. "And remember—no gagging, you need to learn to breathe through your nose”.
I opened my mouth obediently, my heart racing as Jason's impressive cock approached my lips. He was already semi-hard, his thickness intimidating up close.
"Eyes on me," he commanded, guiding his cockhead to my lips. "I want to see your face as you learn."
As the warm, musky flesh pressed against my tongue, I tried to remember everything I'd seen him do with Gavin. The way he took my husband's entire length without struggle, the techniques he seemed to employ effortlessly.
"Relax your throat," Jason instructed, one hand coming to rest on the back of my head. "Don't fight it."
He pushed forward slowly but deliberately, giving me no option to retreat. Three inches in, I felt the familiar urge to gag rising in my chest.
"Breathe through your nose," he reminded me, his fingers tightening in my hair.
I looked at Jason and did what he said, more of his cock inching down my throat. I had about half his cock down my throat when I started to panic. I couldn’t breathe; I thought I was going to black out.
Jason grabbed my head and told me to look at him, relax your throat, he said in a commanding voice, now breathe slowly through your nose. I started to get some air, he pushed more of his cock down my throat, he was nearly all the way down now. I couldn’t believe I had most of his cock down my throat.
He now fed me the rest of his cock, and he started to forcefully fuck my face, and I wasn’t struggling. I took all he had. Jason started to moan of fuck yes, that’s how you do it Tim, yeah, milk my cock, I was a mess; tears were coming down my face, I was drooling, but fuck I felt so happy that I had Jason’s cock all the way down my throat. Oh fuck, here it comes, you cuck he screamed and blasted shot after shot down my throat.
He pulled his cock out of my throat and told me to lick him clean. I eagerly lapped up all of the leftover cum from his cock, I felt an eagerness to do as I was told. That was great Jason said. Gavin will be so pleased when you can finally take him all the way down your throat, although his cock is a bit longer than mine, I had such an overwhelming feeling of satisfaction that I had pleased him.
Over the next few weeks, Jason would come home early without Gavin, and I would make sure I was naked and waiting as expected with my hands behind my back and legs apart. He would fuck my throat, making sure I didn’t have any issues taking his cock. He started to unlock my cock cage as a reward for every time I did a good job and didn’t gag on his cock.
The next time I saw Jason, he told me it was now time to learn to take a bigger cock in my ass. He had brought a bag with him and pulled out a few different-sized dildos. There was a large, thick dildo that looked very much like Jason’s own cock, girth and length-wise, it had to be at least 8 inches. There was also another much larger dildo, it was just as thick as the previous one, maybe a bit thicker, but much longer, it had to be at least 12 inches.
Jason looked at me and told me not to worry; this will be your ultimate goal, once you can take this with ease, you will no longer have any issues taking Gavin’s cock.
Jason Pov
I couldn't help but smile as Tim's eyes widened at the sight of the larger dildo. The fear and excitement mingling on his face was exactly what I'd been cultivating these past weeks. Training him, making him realise how he was the perfect submissive, had been more satisfying than I'd expected. I had purposely kept Gavin busy at work with new clients so I could spend more time with Tim.
"On all fours on the bed," I instructed, watching as he scrambled to obey.
His cage swung beneath him, reminding us both who controlled his pleasure now. I'd kept him locked for nearly three weeks straight, only allowing occasional releases when he'd performed exceptionally well. The psychological effect was exactly as I'd hoped—he was becoming increasingly focused on pleasing me rather than seeking his own satisfaction.
"We'll start with something manageable," I said, selecting a medium-sized dildo from my collection. I lubed it generously, then positioned myself behind him. "Remember your breathing techniques. I slowly increased the pressure against his hole until the head popped inside. Tim gasped, his body tensing momentarily before I felt him consciously relax.
"Good," I murmured, pushing the toy deeper. "You're learning."
Tim's breathing became controlled and measured as I worked the dildo in and out, gradually increasing the depth with each thrust. His submission was beautiful to watch—the way his back arched, how he pushed back against the intrusion despite any discomfort.
"More," he whispered, surprising me with his eagerness.
I obliged, fucking him steadily with the toy until he was moaning and begging for it. Only then did I switch to the larger one—my replica.
You’ve had this one before, Tim I said. When I first fucked you months ago in front of your husband after accepting my offer for the house you now live in.
The memory of that first time sent a shiver through Tim's body as I pressed the larger dildo against his opening. His hole was already stretched and slick from the warm-up, but I could feel the resistance as his body remembered the thick girth.
"That's right," I murmured, applying steady pressure. "Remember how good it felt when I fucked you that first time? How you came harder than you ever had before?"
Tim whimpered as the head breached his opening, his fingers clutching at the expensive sheets. "Yes, sir," he gasped. "I remember."
"And now look at you," I continued, working more of my replica cock into his eager hole. "Locked up, trained, desperate to please. This is who you really are, isn't it Tim?"
He nodded frantically, pushing back against the intrusion. I could see the transformation in him—from the confused, jealous husband to this perfect submissive willing to take whatever I gave him. The cage beneath him strained with his arousal, his body betraying how much he enjoyed being controlled.
"Answer me properly," I demanded, thrusting the dildo deeper.
"Yes, sir!" Tim cried out, his voice breaking. "This is who I am. Please... please don't stop."
I worked the replica cock fully inside him, watching his body accept what once would have been impossible. His training was progressing beautifully—faster than I'd anticipated. Soon, he'd be ready for the final stage.
"Gavin's going to be so impressed," I told him, establishing a steady rhythm with the thick toy. "When he sees how well you can take him now. No more complaints, no more resistance."
Tim moaned at the mention of his husband, his hole clenching around the dildo. "I want to make Gavin proud”.
"You will," I assured him, twisting the dildo to hit his prostate. "He doesn't know about our little training sessions yet. I've been saving that surprise."
Tim's whole body shuddered as I continued working his ass, opening him wider than he'd ever been before. His moans were getting louder, more desperate.
"Please," he begged, "please let me cum, sir."
I laughed, low and deep. "Not yet. You haven't earned it today."
I pulled the dildo out completely, watching his hole gape and contract, hungry for more. "Now for the final test."
Tim looked back at me over his shoulder, his eyes wide as I reached for the largest dildo—the one that exceeded even Gavin's impressive length.
"I... I don't think I can," he whispered, but there was no conviction in his voice.
To be continued………
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