One Year Internship Ch. 15 – Week 30

A few hours later, I arrived in apartment 2 and prepared myself and the room. I sat on the floor and prepared my mind for this experience. I needed to get into character. I am a very open-minded person and needed to be, to execute what I had planned. Shortly after, Pete arrived. I let him in and as he walked past me, I scolded him for being late and told him he was to be punished. He took off his overcoat to reveal that he was not wearing much aside from some leather straps with various handles in convenient locations.

As we headed to the bedroom, he strapped the rest of his outfit around his neck and face, and I removed my clothing. When we got to the room, I ordered him to lie on the bed on his back. I crawled on after him. "I have something for you," I exclaimed.

I got into position, my legs straddling his shoulders. I had my ass and my pussy both plugged. Each had a surprise contained within. I lowered myself down and ordered him to lick and kiss around my plugged holes. Some juices and lube remained from my earlier activities. He slithered his tongue around the plugs and over my taint cleaning me dutifully.

Before I got too aroused, I chided him again. "You did a decent job, but if I give you more, you better pleasure me. Do you think you can do that?"

"Yes Mistress," he replied.

"I can't hear you. Try again."

He spoke a little louder. "Yes Mistress. I'm sorry Mistress."

"What are you going to do for me?"

"Pleasure you Mistress. Give you multiple orgasms and clean your lady parts perfectly."

I lifted my right leg and pushed myself partially up. I reached down and started to remove the thick plug inserted into my pussy. I groaned as it started to slide out. At first it was snug, but soon the thick part of the bulb stretched my tight opening to its limits. I rotated the plug sending jolts of pleasure throughout my body. My toes were still tingling as the plug popped loose.

I grabbed ahold of Pete, by the strap above his forehead, and pulled his face into my cunt. He immediately started sucking and licking. I made sure it was quite full as a result of my previous appointment. Three guys left sizeable donations in there in preparation for this event. Over the next several minutes, he pleasured my pussy, cleaning it along the way, and swallowing everything he found.

Soon enough, his talented mouth gripped onto my clit and pushed me over the edge. Two hours of pent-up anticipation flowed out of my body and into his mouth. It was so much; I think I heard him gulp.

We rode out my orgasm before I moved to the next phase. "You did a nice job cleaning my pussy and pleasuring me. I think you deserve a reward," I commented. I dismounted his face and slid over beside him.

Pete is not a very big man, only a few inches above five feet when standing. Now at his side, I reached down and gripped his slightly below average erection and started to stroke it. I had something in mind that I quickly wanted to get to. A quick glance at his face, in between the leather straps, I could see his anticipation.

After stroking him for a few minutes, I could see the pre-cum leaking from his swollen cock head. I resisted the urge to taste him. But it was time for me to add to his stimulation. I reached over to the nightstand and grabbed a decent size purple ridged dildo and the bottle of lube next to it.

Pete watched me with muted anticipation as a lubed up the rubber phallus. The expression on his face changed as I spread his legs and made his anus available. I placed the bulbous tip of the dildo against his puckered entry and slowly pushed it in. I paused briefly to let him adjust. I leaned in closely to him and whispered, "Is this what you want? You want me to fuck your ass?"

"Yes Mistress," he whimpered.

With only a slight regard to comfort, I pushed the rest of the fake cock into his ass in one smooth motion. He closed his eyes and groaned. I slowly worked him over for a few minutes as a warm-up before finally increasing the pace. As I rapidly fucked him with the dildo, I paid close attention to his leaking cock to make sure he did not explode. I had plans for him.

After some minutes, I pulled the phallus completely out and threw it down onto a towel I had sat on the floor. "Mistress?" he asked. "Be quiet! I am not ready for you to cum yet." I responded.

I crawled back on top of him, straddling his face again, this time facing the opposite way. I leaned forward, lowered my pussy down to his mouth and ordered him to get busy. He dug his face into my wet cunt and started licking and sucking for all his worth. I started grinding my pussy harder into him as I was determined to get another orgasm out of him.

It took some time, but I finally covered his face in the sweet juices of my release. Slowly and deliberately, I rolled my hips wiping myself all over his face, leaving my mark. Now satisfied, I needed to move to the next phase.

Just like before, I lifted slightly, reached around, and started to remove the plug from my ass. I may have been more excited than Pete as the metal bulb stretched my anal opening. Even though I knew what awaited him, I could not help but tease him. With the thick part of the plug stuck in my ass, I chided him, "Do you want what's inside my ass?"

Pete gave me a muffled response. I yelled at him, "Answer me clearly or I'm done, and you will get nothing!"

He spoke up, "Please Mistress. Please!"

I pushed the plug back inside my ass and crawled off of him. I crawled off of the bed and assessed him. His eyes had a strong look of worry. His body was tense and fidgety. His cock was still hard, and leaking juices. I walked around the bed purposefully adding stress to the situation. Without prompting, he pleaded with me, "Please Mistress, let me pleasure you. I want to taste you and experience everything you have."

My emotions felt some sympathy for him. I always knew I was going to give in. It was part of my plan. I crawled back onto the bed and remounted his face. "You better pleasure me better than you ever have before!"

The methodical process started again, as I reached back and gripped the plug lodged in my ass one more time. As the thick part of the bulb stretched me once more, I rotated it in circles causing my body to tingle and my pussy to leak. It also added drama to an already tense situation.

With my other hand, I found the strap on the top of his head and readied him for what was next. As I pulled the plug fully out of my ass, I pulled his head in between my cheeks. I wanted to make sure he got all of what was to come.

I squatted further, somewhat suffocating him. I wanted him fully connected with my leaking asshole. I felt him attach and gasped as his tongue penetrated my slightly gaping hole. I closed my eyes, concentrating on the feeling of the cum oozing out of my ass and his tongue cleaning me so thoroughly. I reached down and started rubbing my clit, causing an orgasm to start to build.

Even though the game plan was intended to benefit him, I was enjoying the special attention. I increased the pace of my motions on my clit, pushing for my orgasm to come out of hiding. "Harder, deeper," I exclaimed, imploring him to help me get over the edge.

My orgasm eventually found its way and as my body jerked in pleasure, I pushed the remaining bits of my previous appointment's donations into Pete's open and willing mouth. I allowed him a few more moments of pleasure cleaning my anal passage before I moved on.

I crawled off him again, moving next to him. "You have done well, and deserve one more gift," I told him. I reached over to the nightstand one more time, this time getting a large black phallus with thick defined ridges and a huge head. As I got into position, I could see Pete's eyes get wide. I knew this was going to be part punishment and pure enjoyment, both of which he needed.

The anticipation was thick in the air, as I lathered up the huge plastic unit in my hands. Once ready, I instructed him to pull his legs back as far as he could. He did so, with some trepidation. Once raised, I pushed them back farther causing him to whimper.

He was almost folded in half as I placed the head of the big cock at his gaping opening. He gasped as the oversized head popped through. I paused letting him adjust to the thickness. The lube started dripping down the length of the fake cock and pooled at the stretched entrance of his backdoor.

After a couple minutes, I told him I was going to continue. He nodded cautiously and I moved forward. His face contorted as I pushed some of the length into his body. His cock was leaking forcibly now, but because of the angle, it started dripping onto his upper chest.

After maybe more than five minutes, I was able to get more than half of the mammoth hunk of plastic into his ass. He was moaning loudly by this point. As I moved the phallus in and out, I assessed the positioning. Lube was good. Angle was okay. It was almost time.

"Do you deserve for me to give you the rest of this?" I asked sternly.

"Ahhhh... yes Mistress... I'm going to cum Mistress."

I positioned myself between his legs, allowing me to push his body forward using my hips, freeing my hands to do what they needed to. With my right hand I increased the pace and thoughtfully pushed a little more of the cock in with each thrust. With my left hand, I gripped his previously unattended cock and slowly started stroking. I knew I did not have long to execute my vision of a perfect finish.

Thankfully, time seem to slow down for me so I could line things up. "Cum for me simp. Do it now!" I yelled at him. I pushed his body forward more than either of us thought possible and jerked his cock violently. Just as I shoved the final portion of the ten inches inside his asshole, he exploded.

I tactfully aimed his cock as it poured what seemed like a gallon of sticky, white sperm all over his own face. His mouth was so wide open from the fucking I was giving his ass, that gobs of cum landed on his tongue and slid into his mouth. The self-facial lasted more than a minute before the last drops from his cock fell.

I backed away, allowing his body to unfold and stretch back out. I crawled off the bed and worked my way around it, gathering up the supplies and cleaning elements of our adventure. Off to the bathroom to square things away. I think I was gone for longer than I had planned, showering, and cleaning the supplies.

When I returned to the room, Pete had removed the huge cock from his ass, and it was lying on the bed. It looked like he was sleeping. I could only see a few small dribbles of cum remaining on the straps covering portions of his face. I left him alone and took the monster to the bathroom to clean.

When I finally returned, Pete was still out. I checked to make sure he was okay and wrote a note giving him instructions for leaving the apartment and headed next door to my own. He sent me an email later that night thanking me for the best experience he had ever had, so he says. Mission accomplished.

That was a few days ago. Now, I sit in my apartment almost thirty minutes short of a much-anticipated appointment with Jon. My goal for this session, is to take him completely in my pussy, completing one of my three goals with him. I am confident I can do it, as I have been preparing myself for two days.

I reach down and slowly pull out the big monster dildo that I have been using to prepare my pussy for this task. I estimated that this plastic phallus is about the same size as Jon, so I am hopeful I can reach my goal. I am finishing touching up some minimal makeup and straightening my summer dress when the alarm goes off telling me that it is time.

Apartment 2 is clean and organized like it always is after housekeeping is done with it. As I gaze at the bed I am soon going to be in, I have flashbacks of some of the adventures I have had in this room over the past several months. From my first appointments with Nicole and Lance, to meetings with Jon, to my early times with Shana, to every single appointment with Ashley, to my latest conquest with Pete. This room has had its share. I was looking forward to adding to it today.

My daydream was interrupted when Jon spoke from the doorway, "Penny for your thoughts?"

I turned to see him, and my heart fluttered. As older men go, I was attracted to Jon more than any other. He is handsome, and distinguished, incredibly successful, and surprisingly compassionate. It didn't hurt that he was a great lover with a deliciously big cock.

I commented, "I am so glad to see you."

"What's on your mind? It looked like I broke your train of thought."

I smiled. I closed the gap between us and commented, "My mind was battling between the memories I have in this bedroom and the one I want to make this evening."

I initiated a passionate kiss with him. My body melted as his tongue tangled with mine. My pussy had been wet all day as I worked to loosen it up and get it ready for its mission tonight. I was not wearing any panties and juices were draining down my leg right now.

We kissed for a few moments before he broke it and commented, "Someone seems quite eager. Are you thinking you are going to be successful tonight?"

I started unbuttoning his dress shirt and replied, "I know I am going to be successful tonight."

It did not take us long before we were on the bed naked and working toward the inevitable. We had been together many times and were quite comfortable with each other by now. He lay on his back, hands behind his head, as I gripped his mostly erect manhood.

I expressed, "I am going to get you warmed up, and nice and hard, with my sexy mouth, and then I am going to ride you like no one has ever ridden you before."

I took in his smile as I slid my mouth over his big helmet. Even though he is quite large, I enjoy sucking his cock as much, if not more than any other. I hummed as I made my way up and down his manhood. It got stiffer as stroked him. I glanced up to see the look of enjoyment on his face.

"Are you going to try for oral today?" he asked.

Just an inaudible 'unt-uh' was all that he heard. I did slide deeper down his cock, teasing him with my throat, but that was not the mission today. This was just to warm him up and get him stiff.

When I felt he was ready, I licked up and down his shaft getting him nice and slick. I kissed up his abdomen, along his chest and up to his face. As I straddled his midsection, I leaned down and kissed him passionately. My pussy was so ready for this, and I was excited.

I broke the kiss and asked him if he was ready. He nodded his head, and I lifted enough to position him at my wet entrance. I whispered to him, "I hope you're ready, because it is going to happen today."

I parted my tiny lips with the head of his cock before carefully starting my descent. I looked into his eyes as I started to slide down his cock. For a brief moment I questioned whether the dildo that I had been using was in fact as large as Jon was. His cock seemed to freshly stretch me as it took several minutes to get even half of him lodged into me. Finally an orgasm helped the progress along.

He had an encouraging look on his face, even if I could read the doubt in his eyes. I was determined to win this struggle. I put my hands flat on his chest and rode up and down his cock with intent, taking opportunities to force more of him in me every dozen strokes.

The fatigue started to set in after a while. I slowed down and reached behind me to gauge how much I had left. Maybe two inches, was the best I could guess. I felt so full, maybe more than I had ever felt before. I think Jon knew what I was thinking. He commented, "That is quite far, Megan. You feel amazing."

"Not far enough. I promised you a ride you have never had before."

His smile motivated me. I reached down and started massaging my clit. I think I needed another orgasm to get to the finish line. Jon reached up and started tweaking my nipples. Between the two motions, I felt that familiar tingle return to my pussy and battle the discomfort from his big cock.

I closed my eyes and visualized an amazing orgasm that was approaching. I pictured his cock completely inside me and the look of ecstasy on Jon's face. I was motivated to make it happen. I increased the speed on my clit and the force at which I was coming down on his cock.

Jon moaned as I felt my pussy start to give, and more of his length fit inside of me. My orgasm was making its way to the surface. My moans started to compete with his. I wish I had one camera positioned between his legs to see his cock disappear and the triumph that was soon to happen. I dreamed of another camera positioned on his face to see the expression when I fit him completely inside. I was almost there.

I started holding my breath and frigging my clit as fast as I could. My orgasm was imminent. I needed to make the rest of it happen. Jon pinched my nipples hard, and I practically screamed. My orgasm shot through my body and I groaned and sat completely down. The orgasm was so powerful, I almost passed out.

I just sat there, with my body throbbing. I finally looked down at Jon and he had his mouth slightly open. It was part smile and part look of disbelief. I also recognized that his chest was wet. I think I squirted on him. I quickly apologized.

"Megan, no matter about that. You did it!"

"Did what?" I asked.

"You were able to do it. Unbelievable."

I smiled. I knew what he was talking about, but I wanted to play with him. "Oh, you mean this?" I said as I moved my hips, shifting his mammoth cock around inside of me.

Jon closed his eyes and groaned, "Yeessss."

I rotated my hips really sucking his cock inside me and only letting a little bit out with each turn. I was almost ready to ride him. The look of pure joy and ecstasy on his face will forever be imprinted in my brain.

"Oh my god Megan! Holy shit!"

"Now for that ride I promised you."

As I started to move my hips a little faster, I felt another orgasm coming forward. I wanted it, I longed for it. I wanted to cum again with him so deep inside me.

I vaguely heard him comment, "So deep... I'm going to cum."

"Cum for me Jon. Splatter the depths of my insides with your load."

I wanted us to come together. He must have been very close because I did not make it three more revolutions before he clinched his eyes, and I felt the base of his cock pulse. I closed my eyes and sunk all the way down and just felt his cock jerk over and over. His orgasm triggered mine and we came together just as I had hoped.

We sat there in a moment of bliss enjoying the afterglow of our shared orgasm. When I saw that he had caught his breath, I collapsed down on him and kissed him. It was a loving kiss as we had just been through a shared experience.

As I parted our kiss, he commented, "That was amazing Megan."

I sat back up and replied, "I'm not done riding you yet."

My pussy now fit his big cock like a glove. All the discomfort had left and all that was left was high level, pure pleasure. I rode him for another ten minutes or so, triggering so many orgasms for me, that if felt like one long continuous one. Finally, I brought him to another orgasm. He groaned almost as loud as he shot his second straight load into the depths of my insides.

I lay on him again, both of us recovering from what just happened. He whispered in my ear, "I did not think it was possible and yet you did it. You never stop amazing me."

"I whispered back, "Challenge accepted. One down, two to go."

I felt him chuckle underneath me. I rose up enough to kiss him again. Again, this one was filled with passion and sensuality. Part of me wanted to get his cock going again, so I could ride it some more. But the logical part of me knew that enough was enough.

Finally, I knew it was time to disembark. I lifted my tired body off of his, allowing his mostly softened cock to slide out of me. Cum dripped everywhere. I hovered over him allowing whatever was going to come out, to come out.