First off I'd like to apologize for the delay between chapters. With everything crazy going on in the world today, I've not had much time to devote to writing. With two other projects on Nifty, most of my writing attention has been on those two projects. But now I believe that this story is heading in the right direction, and I'll certainly make sure there will not be such a lapse in chapters going forward! Thank you for being patient. I'd also like to give a shout out to say THANK YOU to those who have written me in support of this story!
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Trevor's Transformation, Chapter Eight
My sleep was troubled for close to three hours. I tossed and turned and could not get comfortable. The idea of Will being with another man did indeed bother me. Although we'd been dating in a long distance relationship for the better part of two years, we both agreed that it would be virtually impossible to stay true to each other.
There were some periods of time where we would go close to three months without seeing each other, and wow, did we ever make up for it when we did eventually get together. But we both pretty much knew that the other was more than likely going to have some action on the side. He knew about my master status and my desire to train subs since that was how we met. I had told him all about Trevor, and he had told me about a few of the guys he'd met in Champaign-Urbana where he worked at the University of Illinois. There had been talk of him thinking about accepting a better position with a firm in Madison, which would have been ideal for us. But after the initial conversation about the idea a month or so ago, nothing more was said. We made a great couple and were very complementary of each other, but unless he decided to make the move to Madison, our future was headed toward an eventual dead end.
To find myself caged up for an entire week with him holding the key made me believe that he'd come close to a decision. After going through a methodical decision making process about our relationship, I'd come to a conclusion and would definitely talk to Will about it when we got together later in the evening. Instead of flying home to Champaign, he had opted to fly into Madison instead where I would pick him up in great anticipation of the weekend together.
The last time I looked at the clock radio on the headboard, it was almost five am. Trevor was deep asleep next to me, and the last thing I remembered was kissing the back of his neck which caused my caged cock to stir in my briefs. Not wanting to get aroused for nothing, I rolled back over on my left side and fell into a deep, dreamless sleep. When I finally woke up, it was nearly eleven-thirty. I rolled back over to see that Trevor was no longer in bed. Figuring that he was probably out in the family room watching television, I went to the bathroom, took a quick shower, and went out to talk to Trevor.
He was nowhere to be found in the house. Since I knew he was in bed when I fell asleep, I accessed my closed circuit surveillance system to see when he left. I had forgotten to set the house alarm before we went to bed but checking the time stamp on the perimeter doors revealed that he left the house just after ten-fifteen. Someone that looked like a twenty-something male driver in a blue Toyota Corolla picked him up.
Immediately my mood shifted from content to pissed off. I was still responsible for bailing him out of jail, and if he screwed up and got caught doing something illegal again, even if it was being at a party that got out of hand, I would be on the hook for him. There was no note left, no text or anything from him. I only blamed myself for thinking that maybe he'd changed, especially after our conversation last night where he confessed that he was tired of fucking up and just wanted to do the right thing for a change. I decided to send him a text.
<"Where are you? You had better be home soon."
No response.
My idea of how the day was going to play out had just taken a turn in the opposite direction. I should have known that this troubled kid would take any opportunity to leave if he had the chance. If it had been under any other situation, I wouldn't have worried about it. But being responsible for him really bothered me. I tried texting him again.
<"Skippy! Where are you?"
No response again. Damnit!
I decided to make breakfast. Since yesterday's adventure to the leather gym made me incredibly hungry and sore, I opted to make five strips of bacon, three eggs over hard, some hash browns, whole wheat toast and a hot cup of Starbucks "Pike Place" blend. Once breakfast was over and my stomach was satisfied, I cleaned up my mess and then decided to work through some past due invoices for work I'd done in the fall.
Still no word from Trevor three hours later. I had an hour left before I needed to drive to Madison to pick Will up at the airport. Will would definitely have some explaining to do about the phone call from his supposed companion at his hotel last night. Furthermore, he'd better darn well take this damn cage off my cock the very first thing. Honestly, had he not placed this cage on me, I wouldn't have agreed to him flying into Madison.
It was nearly time to leave. I had showered, fought off the hard on that tried desperately to develop in the shower as I thought about being with Will tonight. Once again, I sent the same text to Trevor. No response. As each hour passed, the madder I got and knew that the punishment (should he stay out of trouble and NOT get arrested) was going to be severe. Lucky for me, Will would be home to help administer the punishment, which would be unlucky for Trevor. I dressed in a pair of khaki's, a red and black checkered flannel shirt, my light tan work-like boots, grabbed my jacket and keys, set the house alarm, and headed out. Since the roads were free of snow and ice, rather than drive my truck, I opted to take my Camry instead. A 2019 jet black XSE V-6, the Camry would be a fun ride to the airport. I headed out of town and was on my way.
The ride to the airport on the north side of Madison was uneventful. However, the events of the previous day and the previous week weighed heavy on my mind. First, the fun weekend spent with Will, only to wake up and find this god awful cock cage that I finally got used to wearing, especially after the time spent at the gym yesterday with Trevor and the guys at the gym. That was an entire experience in itself. I chuckled to myself and shook my head in disbelief that I was actually used by those four guys as an initiation into the club. Would I ever go back with Trevor? Perhaps. Once my cock was free of this damn cage, I'd definitely show those other boys a thing or two about being a top and them being the bottom bitches. Would I ever take Will there? Doubtful. Thinking about Will, How would I handle the phone call I received from his supposed lover in San Fran named Preston?
So many unresolved questions. First things first. Get this fucking cage off and maybe I'll be able to think clearer. Sure am glad I'm man and not a woman!
And thinking about unresolved questions, Trevor. What's up with him, where is he, and why isn't he returning my texts. All I can hope is that he doesn't get in trouble with the police, otherwise I'm screwed out of my bail money. Fuck! Why did I get involved with this damn kid who acts like he's ten sometimes instead of twenty years old?
The lights of the beltline now came into focus as I quickly approached Middleton. A short drive around the south side of Madison and then a few more miles through town and I'd be at the airport. Will's flight was supposed to arrive at 7:25 pm, and I was running at least a half hour early. With that in mind, I pulled into a Dunkin Donuts drive through, picked up a large hot coffee with cream and sugar. With the miniscule amount of sleep last night, I needed the caffeine to clear my brain. Sipping the hot coffee did help, and minutes later I pulled into the Madison airport, parked, and began the walk to the terminal. Checking the status of Will's flight, I was glad to see that it was actually on time for its arrival in fifteen minutes. At least my wait would not be too bad, so choosing to sit down and people watch seemed to be a great idea.
A half hour later, people started emerging from the second level of the concourse, where arriving passengers came down a flight of stairs to retrieve their luggage. Since this was a flight from San Francisco, there appeared to be a larger than normal group of obviously gay passengers. A flamboyant, obviously gay guy that appeared to be in his early twenties screamed his friend's name when they saw each other, and the friend, who was there with his lover ran up to greet him as they embraced. Finally, after another group of seven or eight passengers descended into the baggage area, Will appeared at the top of the stairs. Dressed in a white dress shirt and a blue sport coat wearing blue dress pants, his blonde hair neat and perfect, one could easily think of him as a GQ model. Immediately I felt my cock start to stir in my boxer briefs. The pain of the cock cage would soon be gone, and Mr. Will and I would soon celebrate his return with a night of passionate, yet hungry sex that just might include a fair amount of bedroom bondage...
"Hey Johnny, how are you? Did you survive the week without me?" Will started the conversation. His million dollar smile nearly melted me into forgetting everything that transpired over the past week, culminating with a middle of the night phone call last night from a very intoxicated guy claiming that he was going to steal my lover.
"I'm as good as can be, much better now. Come here you big jerk. You know I'm not very happy with the condition you left me over the past week!" As we embraced, I could feel his hardness pressing against my captive cock, causing my own cock to strain against its steel restraint.
"You lasted the entire week? Wow! I'm surprised you didn't find the key. I left one in your headboard cabinet, in your box of Trojans. Holy fuck! I thought for sure you'd find it!"
"You bastard! You're going to pay for this!" I said half laughing, half pissed. "What a great trick you played on me. So I'm assuming you the other key with you?"
"Yes, my love, of course I do. If you wouldn't have been able to make it the entire week, I would have told you where the key was."
"Sure you would have. Easy to say that now!" I laughed and smiled. Despite all of the pain and agony this damn cage caused me, it was a great lesson in behaving, even though I did anything but behave over the past week. "Are you hungry? Want to get something to eat?"
"Yeah, that sounds great! What do you have in mind?"
"Well I heard about and saw a new Thai restaurant located near the beltline in Middleton. Hungry for Thai?"
"Oh fuck yeah! Especially since seeing a lot of hot Thai boys in San Fran! Let's go!"
The restaurant was fantastic. The restaurant had just opened a few weeks earlier, so for a Friday evening it was packed. Lucky for us, I'd made a reservation on the drive to the airport, feeling pretty confident that Will's flight would arrive on time.
Our conversation was awesome. Will told me about his business success on the trip, how groundwork was laid for the project, and how he could do most of the work virtually but would probably have to make another trip to SF in a month or so. After we exhausted talking about the trip, Will asked about Trevor.
"So what's up with your sub boy?"
I had temporarily forgotten about Trevor, immersed having an adult level conversation with Will. "Well, my boy has screwed me over again. Explaining to Will what transpired over the past week, including our trip to the leather gym club here in Madison, seemed to interest Will on what course of punishment should be given to Trevor.
"Wow, John. Sorry to hear that. Obviously, this kid is really messed up. Do you think you've helped him or hindered him with treating him like a pup?"
"Not sure." I replied. "On one hand, he responded really well and didn't mind being my pup. There seemed to be a bit of a breakthrough in his emotional being as well. He spoke of his father and did seem to be genuine when we talked in the truck coming back from the club. But when I woke up this morning and found him gone from my bed -- and keep in mind he's been locked up all week as well -- I just was severely pissed in thinking that he screwed me over like this."
"I think he played you and knew exactly what he was doing when he cried on your shoulder about his dad and all. He knew if he was sympathetic and cried on your shoulder, you'd let him not be caged, thus giving him the chance to bolt away from you."
"Damn. You do have a point. I'm surprised I fell for it," was all I could think of in reply. "He screwed me purposely. Fuck! Now I just hope he doesn't get caught doing anything wrong and gets re-arrested. But I did not remove his cage, so I'm thinking he's going to have to come back soon."
"John, if it's one thing that is a consolation, my feeling is that a runaway dog usually finds his way back home to his master, one way or another."
"I hope you're right." Our meal was over, we paid our server, left the restaurant satisfied with an awesome dinner. We hopped in the Camry and headed west to Spring Green.
Our conversation about what to do with Trevor continued. Over the next ten miles, just on the other side of Cross Plains, we had developed a plan on how to deal with Trevor, whenever he showed up at the house. Since Will would be staying with me for the weekend, it would soon become a weekend that none of us, especially Trevor, would forget. But first things first: time to get rid of this damn cock cage!
The remainder of the thirty minute drive went quickly. My caged cock, which had now become accustomed to being restrained from reaching a full-blown erection, was leaking like a faucet into my black CK boxer briefs. To make matters worse, Will was caressing my neck, ear, and sometimes my right nipple with his hand. To say I was horny was an understatement. It had been a miserable entire week without any touching of my now semi-hard cock. I could not wait to get home.
As we pulled into the garage, I looked over at Will's blue slacks and noticed that he was tenting. Now nothing was going to stop us. We were like a freight train that was headed downhill with no brakes to stop us from delivering our loads. We nearly made it into the kitchen and were now wrapped up in each other's arms. I realized just how much I'd missed him, and not just because I was caged. We embraced immediately and began kissing with a passion that burned like a wildfire out of control.
"I need a shower" Will whispered in my ear. "The long flight from SF to here has me in need of a shower." I nodded my head, thinking that I would join him.
"Okay, just get this cage off my cock first," I replied in his ear, nibbling on his earlobe. "I'm in need of a good scrubbing of my junk, if you know what I mean." With that, we stripped off our clothes in the bathroom and as Will retrieved the key that would set my cock free, I drank in the beauty of his long, lanky body. Standing nearly six foot-three, Will's body had virtually no body fat, but rather lean, tight ripped muscles that defined a strong upper body. His six pack and the rest of his body was smooth, except for a slight blond treasure trail that led to a similar patch of blond pubes around his seven inch uncut cock that has a nice upward curve. A full set of larger balls in a smooth sack were hanging low, begging to be sucked. Both of us were now naked, and acting as if he was forgetting something, Will reached into his pants pocket, and pulled out a key ring that held six or seven keys. Looking at them one by one, he finally remembered which one unlocked the cage. He knelt in front of my cock, and before inserting the key in the lock, he ran his fingers up and down my legs, then my abs, finally tweaking both of my nipples while his tongue found the bottom of my sack. I was starting to get hard, which in turn caused the cage to push the hard metal ring down onto my balls, and that familiar ache returned in my gut. Knowing I'd suffered enough, he finally inserted the key, turned the lock and the top portion of the cage finally came loose, and my cock sprang free into the first full-fledged erection I'd had in a week. Will went to take my entire cock in his mouth, but the smell from not being cleaned stopped him.
"Eww, baby, we need to get you cleaned before I'm putting this in my mouth." I just laughed and turned the water on in the shower. Once the water was warm, we both entered, embraced again, Will kissed me shoving his tongue deep in my mouth. I had almost forgotten what a great kisser he was, as our bodies intermeshed together with the warm water from the shower head cascading down upon us, my now rock hard rigid cock touching his, I was afraid I was going to shoot my load all over his junk. Will grabbed a wash cloth and the bar of Dove Men's soap, lathered up the wash cloth and commenced to wash my chest, my arms, my back, my legs, feet and then finally moved to my rigid cock that was as hard as I can ever remember it being. With the steamy water showering him like a rain shower, he knelt on the tile floor and carefully cleaned my cock and balls with the washrag before finally soaping up and cleaning my still sore hole, which was abused by the gang bang at the leather gym the night before. My hands were all over his wet blond hair, and as soon as he was done washing my hole, I pulled his head to my cock. Expertly, he engulfed the head and shaft of my cock in his mouth, working it in until his nose touched my trimmed pubes and his chin rested on my now full smooth ball sack. The feeling of Will sucking and deep throating my cock was almost way too much for me to handle. Sensing I was close to blowing my load deep into his throat, he pulled out what seemed like a foot of cock from his mouth, then moved up to kiss me; our tongues and cocks now entangled in each other as we held each other under the shower. The feeling of his hard on against mine was incredible, and the feelings I had for Will came flooding back like a tidal wave drenching both of us in a special love that we shared just between us. He then whispered in my ear "take me downstairs; I've been bad and need to be punished."
I nearly came at the very notion of returning to the special bond that Will and I had as master and sub. It had been nearly ten years since we'd role played. He was my first sub and played the role perfectly. Tonight was going to be special, no doubt. I reached down and shut the water off. After drying off, I dressed in a pair of leather shorts, got my socks and leather boots on, as well as my black leather vest. Will met me in the basement wearing only a pair of skimpy black g-string underwear -- the kind that only had a pouch for his junk. At the sight of him, my cock which had softened only a bit returned to its hardened state. The fun was about to begin.
As soon as we entered my dungeon room, I immediately pushed Will up against the cross and fastened his arms to the cross at his wrists. He played the part of a sub perfectly, asking me what I planned to do to him. Next, I fastened his legs, which were now nearly three feet apart at his feet. Of course, his black g-string pouch was growing, and so that meant he was liking this too much and would have to get some punishment. I grabbed the small black whip out of the closet and began lightly whipping his lean stomach and abs.
"So you've been naughty little bitch, huh? Going out on your master? Think you can find a better piece of ass? Is that it?" with each response of no, the whip hit him harder. His abs were now getting red, his cock was obviously rock hard, straining to get out. Time to take things up a notch. Next, I applied two nipple clamps to his nipples, causing him to wince in the pain mixed with pleasure from the pressure applied from the clamps. He knew that if he showed pain or spoke, it would only get worse. And show it he did. I responded by shoving the ball gag in his mouth and fastening it around his neck. His moaning continued and so did the whipping. Whipping him up and down his thighs to his feet, his cock to his mouth, and back to his cock again. He was enjoying this way too much. Reaching in the drawer, I pulled out a donut shaped ball weight. The weight was one of the biggest ones I have and is held on by a hex head screw. I ripped off his g-string, freeing his cock which was now dripping precum. After fastening the ball weight and tugging on his full balls, Will moaned even more from feeling his balls being pulled down. The pressure in his groin gave him the sensation of being kicked in the balls, one that he had always enjoyed.
"Oh, so you think you can leak your piss or juices all over my floor you fucking maggot? I don't think so!" With that I grabbed the 10 mm penis plug, the one that is close to three inches long, that has a ring fastened to the end which fits snugly over the head of his cock. Even after applying cold lube and quickly shoving in his pee hole, he still remained rock hard.
Next, I untied him from the cross and fastened his hands above him to a chain hanging down from the ceiling. This allowed me to focus on his tight, muscular legs and ass cheeks. I must have whipped his ass close to fifty times, each cheek now a bright red, almost matching the red skin of his abs. All this time his captive cock completely erect, his ball sack taut and his full balls aching to be released. Going back to the cabinet I pulled out one of the largest black butt plugs that I have. I lubed it up generously and began to insert in his hole.
"This will be the test to see if you fucked around on me when you were away. If your hole takes this all the way, I'll know you've been getting fucked by another stud. If it doesn't then I'll know you're telling me the truth." He mumbled something incoherent through the ball gag that sounded like he'd been true to me, but I'd find out in a few minutes. Slowly I tried to insert the butt plug in his hole.
His hole was tight as could be. I knew that more than likely he hadn't cheated on me with Preston or whatever his name was in San Francisco. But as master and sub, I would play along with it until he told me the honest to god truth.
I knew that the huge triple ring butt plug wouldn't work, so I grabbed a thinner plug that was about the size of my cock. I lubed it up and slowly stretched his tight hole until the plug was implanted in his rectum. As the tip contacted his prostate, he began to moan with pleasure. With a longer leather whip now in my hands, I got as close to Will's face as I could. I was pretending to be really pissed off now and started yelling at him like I was a drill sergeant and he was my soldier.
"Goddamn it maggot, you better tell me the fucking truth about that queer fucking piece of shit who woke me up last night. Did he fuck you? Did he?"
"No sir, he did not." Will replied quietly, now playing along.
"I asked you a fucking question. Did you let that faggot fuck you last night you fucking maggot?!"
"NO Sir, he did NOT!" I cracked the whip three times across his back, and lightly on his now completely hard cock.
"DID YOU Fuck HIM?"
"No sir, I did not." He whispered, almost defeated. Two more cracks of the whip. Will's cock was still standing tall and hard.
"Did you Suck his cock, or did he suck yours?"
"No Sir, he did not, and neither did I." Three more cracks of the whip on his back and front. Cock pulsating, desperately wanting release from the penis plug and the ball weights.
"ARE YOU LYING TO ME?" Four more cracks across his reddened ass cheeks and now red cock.
"No, No. Please sir, I am not lying to you. I would never do anything to jeopardize what we have here, sir." I detected a few tears starting to roll down his face. Will always did have a penchant for crying on demand, so he was acting the part of a sub that was sorry for what happened.
"Okay maggot, I'm going to unchain your hands, but now you're going to climb up on the table, lay your head over the edge, and you're going to suck on my hard dick until I tell you to. And if you make me cum before I tell you to, I'll leave you tied up down here all night. A slight grin appeared in the corners of Will's mouth.
Now tied up on the bench, hands at his side, legs shackled down, he could not move. The butt plug was still inserted in his ass.
I released the piece of wood that was on hinges to support his head and set the flat piece of plywood on a forty-five degree angle so his eager mouth could take me deep into his throat.
Both of us were really horny for the fun that was about to start, and as I eased my throbbing cock into his mouth, instantly I could feel precum oozing from my cock into his mouth. I know that Will's cock must be ready to explode, and after I felt the onset of my own orgasm brewing, I pulled out of Will's mouth and slowly pulled the penis plug out of his swollen cock. Sure enough, it almost appeared as if a stream of piss was dribbling out of his cock, but it was pent up precum that I could not let go to waste. I eagerly lapped up his pool of precum from his abdomen and as it mixed with my saliva, I closed my mouth long enough to deposit the mixture directly into Will's mouth. He eagerly sucked it out like it was the sweetest nectar he'd ever tasted. As the pain phase slowly was giving way to pleasure -- mainly Will giving me one of the best blow jobs I'd had in recent history -- I was ready to untie him and take him upstairs so we could make the most passionate love two lovers could experience. Will sensed this and even begged me to let him finish sucking me on the bed in my room. I was so fucking hot and hard that thought of our bodies writhing around in the most desirable passion on my bed almost caused me to explode. Pulling out of his mouth to instead unfasten the nipple clamps, the rope around his body, and the shackles around his ankles, I grabbed a bottle of massage oil and began to rub his entire body down. First his chest, then his abs, his arms, his legs, and then finally his stretched scrotum and tender balls. With the penis plug now out of his piss slit, the precum was like a slow running stream, pooling on his abs.
I was ready to tell him to head upstairs with me, to make the love we both loved doing. As if on cue, we were both naked with our hard cocks pointing the way up the stairs when I heard the doorbell ring.
"Fuck, who can that be here now?" I said to Will, not wanting to be interrupted. No lights were on in the house, so we slowly crept up the stairs to the kitchen where I'd left my phone. Turning on the app that is connected to the security cameras and system, I was partially relieved but mostly pissed off at the young man in the dog costume who was wanting to get in the house.
It was Skippy/Max/Trevor.
The night of fun for Will and me had barely even begun.
The night of pain and suffering for Skippy/Max/Trevor was about to begin.