I had my stuff packed before my last final. I remembered Rick saying that he would be providing me everything for the summer but I still packed some basics. I did my best to prepare everyone for me to not be around for the summer. I had broken things off with my law school semi serious girlfriend once I met Rick. She was going to DC for the summer anyway so it was sort of a non-issue. I told my parents that I expected to be basically working 120 hour a week for the summer and I apologized in advance for not being able to contact them much. Nobody suspected a thing, why would they?
Rick lived in the first ring of suburbs in the south side of the city. Not surprisingly, he lived in an impressive home. Not quite a mansion, it had impressive landscaping including strategic tree placement to keep the home completely hidden from the street. The house was ultra modern and was probably 5-6000 square feet. It had the look of a successful law partner home.
I took a cab to Rick's house per his instruction to not bring a car. It was early evening when I was dropped off.
As soon as I walked up to the door Rick opened it, clad in a fancy bathrobe. He had a collar in his hand and he handed it to me without speaking or looking me in the eye. He seemed impatient. As soon as I snapped the collar on (pleasurably tight) he snapped the leash that also had in his hand onto the ring of the collar and pulled me violently down to my knees. His dick was in my mouth almost immediately. I'm fairly sure that sequence occurred fast enough for the cab driver to still be in the driveway. I hoped so.
Rick wrapped the leash around his hand enough times and pulled tightly so that I was actually on the verge of choking. He was yanking the collar at just the right angle as to pull my head up and down on his cock. I looked up at him because that was what I thought he liked and he looked at me with near disgust. He pursed his lips and spit a perfect stream of spit directly on his dick as I was slurping him.
"Ever been spit on boy?" He asked.
"Uh uh" I garbled - cock in mouth - the honest answer.
"Oh shit?" He semi-asked as he pulled his cock out of my mouth. He then grabbed me under the chin and instructed me to open wide. I did. He launched a heavy loogie directly into my mouth. If my dick had been touched at that moment it would have exploded I was so turned on. He then proceeded to spit a few spitballs onto my face and wiped it over my face with his open palm, before using his dick to spread it and slap my face.
All this continued to take place at the threshold of his house, with me on my knees on his doormat and him standing in the door, step above me. For the next few minutes Rick engaged in some very serious throat pummeling. He would continue probing his cock all the way down his throat and keep it there, even as I gagged and choked, creating a large amount of spit and snot on my face. I felt like I was going to puke and I was resisting the urge, but any time I tried to pull away at all Rick would pull my head tighter. I gagged and burped a number of times and I believed puke was imminent a few times. However, I wanted to impress Rick that I could take a dick. I am not sure if resisting puking was helping because it was unclear whether he was trying to get me to puke or if he was just pushing the limits. At times it really felt like he was trying to hurt me. For the first time and not the last time that summer, he restricted my airway enough while facefucking me that I got extremely light headed and felt on the verge of passing out. In fact, I may have lost consciousness very briefly, but it wouldn't have made a difference, since I was being used like an inanimate object.
Rick eventually started to growl while pumping my throat and I anticipated a load was coming. He groaned to me "wanna see how my boy looks with a messy face" and he pulled out and provided me with a Peter North-esque face painting with his cum, to go along with the spit and snot that had accumulated. My eyes were virtually glazed close. I could feel Rick jerking every drop out near my face groaning "sweet nothings" of sub boy humiliation. Telling me what a messy little pig I was and all that.
As I sat there coated in cum I started to realize that my knees were sore from the concrete and that the leash had started to feel pretty restrictive. A fun little session to start but I was ready to go in and hopefully get situated.
"All the clothes off, bitch." Rick said as he ripped the T-shirt that I was wearing straight off my body "sorry, don't want to mess up my artwork."
I kicked off my shoes and unsnapped my jeans and pulled them off quickly, along with my boxers. The socks came off last. My eyes were barely operable from the caked on mess as I sat obediently on the leash.
He picked up my jeans and pulled out my phone and wallet "I will keep these safe for the summer" Rick said and then he walked over to the small suitcase I had brought "what is all this shit?"
"Just some stuff, I didn't know...." I started to say.
"I told you I was going to take care of everything this summer, come boy." Rick picked up my bag and started walking away from the house. I got up to start walking and Rick said "nope" and pushed me hard. I didn't fall but the message was clear I was not to walk while on the leash. I got back down and crawled along with Rick towards the driveway. He opened the trash barrel in front of the garage and threw my bag in and move back towards the house. When we got back to the front Rick maneuvered into the front door, keeping me outside, and closed the door behind him as he slipped in. I could hear and feel that he was wrapping the leash around the inside handle. "Stay boy" I heard through the door.
I sat back down on the front step area. I could feel my eyes burning a bit to look around. The leash was not locked in any special way so I could take it off. However, I had heard the door lock and I was completely naked. I also looked up and saw the camera pointed towards where I was. I knew that Rick had told me that I could walk anytime that I wanted but if I stayed with him it would be a great summer for me and my future. The message was clear that I should stay on my leash if I wanted to make it with Rick.
As I suspected when he closed the door behind him, Rick was not playing around. He did not come back. Time ticked by and the minutes clearly turned to hours. The sun started to go down. It wasn't long before I started to feel hunger and I eventually ate the load off my face for sustenance, as dried and caked as it was. Rick eventually walked around the house with a dog bowl with some chicken and rice and a bowl of water.
"Get some rest boy, we have a lot to do tomorrow." Rick told me as he slipped by me into the house. I ate my dinner and I eventually found the most comfortable position I could find and started to try to wind down to relax. There was no real comfortable position but sitting with my back to the door near where the leash was tucked brought me the most comfort.
I can't say I had a good night's sleep but I eventually did fall asleep. There was a certain enjoyment I got from knowing that Rick was not the type of dom that was going to leave me there for a few minutes to play around. He was sending a message that he expected absolute obedience and that he was going to push me to the absolute limits of submissiveness. I had hoped that he would come back and let me in, but I fell asleep feeling a slight bit grateful that I was being trained to be such an elite piece of meat.
Rick woke me up in the morning by jerking the door open and pulling on the leash. The result was that I was pulled backwards into his house and pulled a few feet away from the door.
"wow that was impressive, no barking or whining during the night, another successful test. want breakfast?" Nice and tender Rick had woken up this morning (except for the leash pulling).
"Yes please."
He unsnapped the leash and helped me up. He looked at me and smirked, maybe even laughed, when he saw what a disheveled mess the night had left me. He put a hand on my ass gently and guided me toward the dining room. He guided me to sit down at the table and he gave me some fruit and oatmeal for breakfast. He told me a little bit about what we were going to do workwise that day.
After we ate he showed me around the house a little and guided me to the guest shower space. He told me to cleaned up and told me to be extra thorough washing out my ass "for my own sake." He left me and I saw the enema, bidet, and shower head system for asshole cleaning that I would get very familiar with during the summer. I spent some time enjoying the shower and cleaning up before thoroughly cleaning out my insides. I had been eating extra well since Rick had told me the summer plans and had me working with the trainer, plus I had been mainly deprived off food the night before so it was fairly easy to clean out.
When I finished in the shower there was a jock strap and an outfit waiting for me. Never in my life had I worn a jock strap before this so I was a little confused by it. As I started to fuss with it I felt Rick's presence in the hallway and he came into the guest room and redirected me and helped me get the jock strap on.
"Don't worry, you won't be staying in here, but we gotta get you set up for the summer so starting in here." As I started to put the suit that he had left for me on Rick said "Oh, hang on" and he pulled something out of his pocket. I could see pretty quickly that it was a medium sized butt black butt plug. He spit on it and pushed me down onto the bed so I was bent over.
"Can't believe I have held off on tapping this so far." Rick said as he slapped my ass hard. I moaned with pleasure. "Oh shit you do like the rough stuff don't you?"
"Yes sir I do." I said - speaking truthfully (thought Rick was certainly a guy I knew was going to test me).
He spit on the plug again and grabbed one ass cheek and started pushing the plug in. Now, I had somewhat limited anal sex experience at this time, but I did know that my preference was for dicks and tongues and not hands and toys in my ass. The wide head and the rubber material felt uncomfortable on my ass. The limited spit lube didn't help. As Rick forced it into my relatively tight asshole it really ripped a shock of pain through me. I practically screamed and moved my hips to escape the plug. Rick had a good grip on my ass cheek though and was able to keep me from getting far just holding my ass. "You are going to have to learn to tolerate pain - you ass will be tested with me" Rick barked as he pushed even harder in response to my reaction.
And then, suddenly, it was in. A relief. I stayed prone awaiting instruction, not wanting to trigger Rick. However, as I was learning, Rick didn't need to be triggered to unleash aggression on me. He kept his grip on my asscheek and pushed the small of my back down - to keep me bent over the bed. He let go of my ass cheek and grabbed the belt that he had left out with the suit. He wrapped the belt in a loop and unleashed a symphony of slaps on my ass. In this regard, Rick was a benevolent abuser, as he knew perfectly well how to whip my ass with the belt without making the type of painful blunt impact that less experienced masters sometimes subject their whipping boys to.
After a little while the lashes started to add up enough that it started to hurt a bit. But it was mostly euphoric. I moaned in pleasure. Rick wasn't sure if I was moaning despite the pain to show obedience or if I was truly enjoying it. Either way after a minute or so that he dropped the belt on the bed, pulled me to a standing position, and grabbed my throat firmly and looked me in the eye. "I'm so lucky I found a good boy like you. You're going to do great." He then gave me a sensual kiss and massaged my chest for the minute or so that we were making out.
"Ok, let's hurry, we have a lot to cover today." Rick said as he walked out of the room.
After I was dressed I came out and Rick gave me a look of approval. His driver arrived shortly thereafter. I was introduced to Jeff the driver. It was a professional and friendly conversation, but there was no avoiding that Jeff must have known I was his boss's new fuck toy. It was a mix of erotic and anxiety inducing as we drove.
Jeff dropped us in the parking garage and we took the elevator up. I was just following along but I was very nervous because I didn't know exactly how to act. When we got up to the office Rick showed me around. He introduced me to his personal assistant and paralegals. I had no clue who knew and who didn't know what was really going on. He took me down the elevator and introduced me to the other Dayton attorneys and staff on the other floor. I got the sense that the "other floor" Dayton people were pretty clueless. I would quickly learn that Rick was able to keep things seperate as needed by using the facade that he was difficult to work with and a maniac and he needed his own space to operate.
He took me back up and showed me his office. It was a luxurious corner office with lots of space and nooks and crannies. He explained to me how he had been able to soundproof his office by telling the Dayton folks that his yelling on phone calls had been distracting to the other people in the office. He also had a nice camera system in his desk area that showed basically what everyone else was doing in his mini office.
He took me to my office, which was a nice windowless space next to his office. It had a hallway door and also a door connected to his office. It had a lock. He explained how he had gotten the contractor to put up sound proofing in there as well. My office had a luxury bathroom with a mini-shower. The office had a back area with a couch and lazy boy chair. I could see the possibilities.
"Here is some stuff for you to look at for the work we have to do" handing me a binder. "There is more stuff on our firm file system, take a look around and get familiar."
"Lunch is at noon, come see me around 11:15 so we can put our orders in." Rick said to me with a smirk.
I spent the next few hours getting acclimated with the work part of the job. There was definitely a lot of legitimate work to be done.
I went to Rick's office as instructed at 11:15.
"Can't believe I made myself wait this long for some of that ass" Rick said as I entered and closed the door.
"Come here boy let me get a taste." I walked around his desk and coyly faced him as I got close, unsure how he was going to proceed. Being in a corner office with panoramic windows made me feel like I was about to get fucked in front of an entire city... and that was cool. I was a little nervous about someone coming in on us. When I stood and faced him Rick unbuckled my belt and unbuckled my pants and pulled them down. He quickly spun me around and bent me over the desk. The jock strap was still on as he bent over and put his face between my cheeks and took a few licks. He seemed pleased. A few moments later as he was sensuously licking he suddenly and violently pulled the plug out of my ass and stood up and reached around and jammed it in my mouth to the hilt. He immediately got back to eating my ass. I could hear him unbuttoning and unzipping as he licked. Soon I heard him pull the drawer open and grab something. I assumed that it was lube, which seemed merciful for Rick.
He stood up and I heard the cap of the lube come off as he prepped his cock. Soon he was slapping his dick against my hole. "Finally, the moment we've all been waiting for." He slid into me. The plug had opened me up but I still felt the pressure of his large piece. However, I was incredibly turned on as I soaked in the moment of getting fucked on the desk of my boss's corner office during the workday. I was able to see the camera system on his desk and could see the door around the corner a bit. It seemed risky but also safe. I turned my head to the side to look at the view of the city. Rick took that as a good moment to push my head down hard into his desk as he started to get into the rhythm of fucking me. It wasn't long before I was thinking "I hope to god this is really sound proof" as Rick's pumping was eliciting loud grunts from me, the usual Rick shit talk from him, and loud smacks of my ass whenever he decided to remind me that I was his little piece of ass.
As far as core experiences of being a little sub boy, this will always be one of the hottest. In that moment I was a hot young associate getting fucked to make my way to the top. And nobody would have ever expected that from me.
AS he continued his fucking got more violent and he was pushing harder into my insides. I was not a very experienced bottom at the time and I could feel the various walls of my ass being broken down. When it was time for him to cum he grabbed me by my shoulders and let out growls as he pumped me full of his spunk.
He collapsed on my for a few seconds, sweating, his cock still inside of me. He whispered in my ear "you're the fucking best pussy I can remember" and he took the plug out of my mouth, that I had been compliantly groaning through during the fucking. He put it in his drawer with the lube and took a few steps back to get dressed. I pulled my pants up and tucked back in and got ready to head back to the office.
"Stop by at a few minutes before noon."
I came back a little before noon and he had our lunches ready. He had picked up a healthy salad with chicken for me.
"You cleaned that asshole out good, right, boy?" he asked me.
"Yeah it was clean, right?" I answered, worried that I was about to be in trouble for making a mess.
"Well, guess we will find out how clean it is... you ever push a cream pie out before?" Rick asked me. The truth was he was the first guy to cum in me so I was dealing with being full of semen for the first time.
"No I haven't sorry." I said.
"Just take your pants off real quick." Rick instructed. He then directed me down onto all fours. "Lean back a little and push like you are trying to take a shit." Rick instructed. I heard him pick up the lunch and open up the box for my salad. He positioned himself behind me with the box. It took me a few moments of pushing before I started to fart his jizz out. It felt something like giving birth as Rick was waiting behind me with my lunch ready. As I started to spray him out of me, he placed my lunch right near my asshole. A significant load dripped out of me and Rick was directing it all onto my lunch. After I got what I thought was all of it out Rick ran his fingers into and around my ass and told me to get up. When I got up he spooned the residual cum into my mouth.
"Get dressed lets go eat." Rick closed the lunch back up and placed it into the bag. We made our way down a floor to the Dayton lunch area and sat with numerous other attorneys and staff. I was introduced as were several other new summer associates. I ate my creamy salad and enjoyed every bite and drop. Rick kept smirking as me and I realized that nobody had a fucking clue how nasty we were and I was loving every second of this.