One Year Internship Ch. 11 – Week 10

I took him in my hand and started to stroke his partially erect manhood. His skin was soft and warm. All day, I had been daydreaming about taking his huge cock in my mouth and now it was time.

I leaned in and took him into my mouth and sucked like you would a piece of candy. I think I enjoyed it just as much. I started massaging his dangling balls as I sucked and bobbed up and down his growing unit. My moans were competing with his.

Soon his cock was very stiff, and I started to get into a rhythm. I felt Jon run his hands through my hair. I love it when a man does that, but in this moment, I was in love with Jon and anything he did would have set me off.

Before I got too carried away, he backed up and separated himself slightly from me. I looked up to him with a confused look on my face. He reminded me, "It is not time to get me off. Do you want to see how far down you can go?" I nodded and he stepped back in front of me.

I sat up to change positions. I needed to be higher than I was. As I shifted my weight and rolled over on my ass, I felt both the plug and dildo adjust inside me. I paused to feel the tremor it caused before cautiously moving more gently to my desired spot.

Once in position, on my knees, still on the bed, I reached out and gripped his thick cock again. I knelt a little and slid my mouth over his head and pushed him to the back of my mouth. I relaxed a little, but no progress yet. Slowly I went up and down working to relax my throat and let his huge invader through.

I changed my angle a little more again and went back down. This time, I relaxed as much as could and pushed with added determination. I felt his cock slip into my throat and tried not to gag. I left it there as I got used to the feeling. I let my mind wonder to the last time we were in his office and managed to get a few more inches into my throat.

He gasped a little as I pushed down a couple more inches and held him there. I pulled off him and caught my breath and went for it again. A few more tries and I was as far as I had last month. I held him there but was having trouble going any farther.

After several minutes of working on him, he finally pulled away again. As I looked up at him with disappointment, he commented, "We can try again later. I want to continue to work on the other parts of you."

Jon pushed me back on the bed and told me to get comfortable again. I slid up to the pillow and he followed once more. Soon he was right back between my legs. I felt him slowly pull out the dildo and then the plug. I felt sad and empty. I did not have to wait long for my fill to be replenished.

I felt another object start to invade my pussy. It was bigger than the first dildo. Much bigger. There was a lot of pressure, but Jon went slow. As he pushed it in, he rubbed my clit sending waves throughout my body. My mind could not decide whether to focus on the pleasure of his fingers on my tiny nub or the pressure of the dildo.

He started moving his fingers faster and that dominated my attention. I felt an orgasm building already. My pussy was adjusting as he slid the giant dildo in and out slowly. The pressure started to change over to pleasure.

Jon stopped everything for a brief second. I took a few breaths and tried to relax. I could feel the dildo stretching my tiny hole. Several seconds later, I felt his tongue on my clit, causing me to moan loudly. He pushed the dildo in farther and I groaned. I felt so full, but his tongue was forcing my building orgasm to dominate my attention.

"Oh my god!" I moaned as the orgasm came pouring out of me. I gripped the bed sheets as my pussy pulsed around the fake cock. My orgasm lasted forever, I thought. I was out of breath and my body was spent. I closed my eyes and tried to let my other senses focus on what was happening.

Jon pulled the dildo completely out of my pussy. I could feel and hear him working his way around my pussy enjoying the juices I was letting out. When he was done, he let me catch my breath before asking, "Ready for more?"

I smiled and replied, "Yes please."

He pushed my legs back a little father and I felt an object pressing against my anal opening. I quickly realized it was bigger than the first plug. I relaxed, knowing that was the only way this was going to happen.

It took several minutes and Jon working over my clit some more before the bottom of the plug pushed through allowing my anal ring to grip the skinnier handle. Jon applied some more lube and started working over my clit again. I could feel him pulling and tugging on the plug working it back out. Upon success, he pushed it back in. Over the next few minutes, he moved it in and out a few dozen times before finally pushing it back in and leaving it like before.

I did not have an orgasm during the process, but by the end the discomfort had switched over to pleasure and I was feeling very worked up. The next action was the toughest. Jon slowly started working the bigger dildo back into my pussy. I was not sure how he was going to manage without tearing me. But he took his time, used a generous amount of lube, and kept my clit stimulated.

After what seemed like forever, both of the largest toys I had ever seen were logged deep inside me at the same time. Even with all of the care that Jon took, I had never felt more stretched in my life. Jon must have seen the distress on my face because he commented, "You might feel stretched right now, but it is going to make your experience with me much easier."

He moved away from me and crawled off the bed. He walked around to the left side and reached his hand out towards me. Unsure of what he wanted; I moved my hand to meet his. He gripped it and pulled me toward him. I slid over on my back, and he grabbed my other arm and positioned me right under him. I looked up in time to see his enormous manhood come into view. I heard him comment, "I'd like to try this angle if you don't mind."

Jon helped me shift a little bit more until my head hung off the edge of the bed. Playfully he rubbed his balls on my face until I opened my mouth and started attending to them. I gently licked and sucked on his balls until he was ready to move to the main event.

I was hopeful this angle would help me get more of him down my throat. He pulled back and aimed his cock at my open mouth and slowly pushed it in. It took several strokes in and out before we found the ideal angle. Soon he was pushing himself into my relaxed throat.

A few minutes in and I could tell I was making progress. I felt his balls push up against my forehead. He slowly pulled out and said, "I am going to press in further and leave it there longer. Let me know if you need me to pull out sooner." I nodded my agreement and opened my mouth wide.

My heart fluttered thinking this was going to be the moment that I took his monster all the way in my mouth. He aimed his cockhead at my mouth again and slowly pushed himself in. When he felt a little resistance, he pushed a little harder. I felt his manhood stretching my throat. I tried to relax and breathe through my nose, with no success. I was still motivated to take all of him and was not going to let a little discomfort hold me back.

Jon stopped pushing and held his cock there for a moment before pulling out. Once my throat was clear, I started breathing heavily. He let me catch my breath before going back in. This time he tried to go a little deeper.

For several minutes he would push in, sometimes making progress, or so I thought, and sometimes not. There were a couple moments, where I was very uncomfortable, or I struggled with no air. But my determination won out and I never pushed him away too soon.

Eventually, Jon pulled away and did not come back. He took my hand and pulled me around until I was sitting on my knees on the edge of the bed. As much as I wanted to concentrate on him, the immediate pressure of the objects still lodged in me were very distracting.

He leaned down and kissed me pulling my attention back to him. As our tongues danced, he ran his hands over my back and pulled me into him. I could have stayed like that forever, but we had other things to attend to.

We broke the kiss, and he walked over to the nightstand and grabbed a towel and the lube. As he picked up the objects, he commented, "Megan, you are amazing. I will say that you are very close to completely taking me orally."

"How close was I? It is hard to tell from that position."

He came back to the bed and replied, "You are maybe 80% of the way there. You probably have a couple inches left."

I smiled, "I am not that fond of that position. I think I prefer being able to see you and have more control."

He nodded and commented, "We can go back to whatever position you like next time. But we need to move along. Do you want to do anal or regular first?"

I thought for a second before responding. "Anal first."

He smiled and nodded. "What position do you want it in?"

"I don't know. I assume doggy style might be the easiest right?"

"I think I would like to lie you down on your stomach. I think that is the best way for you to relax your entire midsection."

I nodded and moved my way back over to the middle of the bed and landed on my stomach. I could feel the large objects inserted inside me moving around. Jon crawled back on the bed and hovered over me.

In a very sensual way, he kissed the back of my neck and slowly worked his way around my bare shoulders and down my back. I felt my pussy squeeze onto the dildo and slightly gush as he kissed my cheeks and down the sensitive portions of my upper leg.

Slowly he moved the plug around in my ass teasing its exit before my ass sucked it back in. He joked, "It does not look like your body wants to let this thing go."

By now the anticipation was building. I replied, "If you don't pull it out, I am going to. I want to feel your glorious manhood in my ass as soon as possible."

He chuckled and went back to work. A little more forceful maneuvering and it broke free, and he pulled it all the way out. I felt the emptiness and a slight gape of my backdoor. There was a slight pause as I felt him reposition himself that only fed into my anticipation.

I felt his lips kissing my lower back and his big powerful hands squeezing my cheeks. My pussy tingled again as the intensity of the situation was building. I jumped slightly when I felt his tongue on my sensitive bud. I quickly got into the moment as his rimming was extremely arousing.

As his tongue did a number on my back door, his hands started working over the dildo in my pussy. I could feel the alteration between his tongue going in my ass and the dildo coming out. He toyed with me for a few minutes until he finally pulled the dildo all the way out. A final round on my ass before he pulled completely away.

After having those large toys in my holes for more than half an hour, I felt very empty. I did not have to wait long before I was to be satisfied again. He asked, "Are you ready sweetheart?"

I looked back to him and nodded. He continued, "Remember to relax and let me know if you want me to stop."

"I will."

The bed moved a lot as he shifted around. I felt his presence as he positioned himself over me. His lips returned to the nape of my neck, and I felt his manhood rest between my cheeks. The rational part of me felt that anxiety of what was about to happen. My sexual side pushed those thoughts down as I desperately wanted to feel him penetrate me.

The lube was a little cold as it slid down my crack and lathered up my hole. A few seconds later, I felt his cockhead press against my entrance. He took his time to allow me to get my breathing right.

Very slowly, he pushed. Very slowly his cockhead split my ass. I tried not to hold my breath, but it was difficult as I felt the pressure growing. Thinking this through, I studied my previous anal experiences. In all of them, I felt the pressure and discomfort in the beginning. In all of them, it soon turned to pleasure. I started playing mind tricks to help with the process.

I was jolted out of my mind games when his head popped through. I jerked and he apologized. I replied, "It's okay. Keep going."

Slowly and deliberately, he moved in and out of my ass, pushing deeper over time. The process was agonizing, but necessary. Quite often, he would just stop and keep his cock still and let my body get used to its invasion. After what seemed like forever, he asked, "Megan, how do you feel? Does it still hurt?"

I took a deep breath and replied, "It doesn't really hurt anymore. But it hasn't started to feel good yet either. Does that make sense?"

"Kind of. I think your body is ready for the sex part of anal sex."

"Well, my mind says let's go."

He chuckled and slowly started to pull his cock a little bit out before pushing it back in. In and out he shifted himself, slowly and gently. "Play with your pussy," he instructed.

I reached between my legs and found my sopping pussy. I started to roll my nub under my fingers sending waves of pleasure throughout my body. It woke up the sensations in my ass and I could more intensely feel his thickness expanding my asshole to its limits.

I concentrated on the sensations right at my ring as his slippery cock pushed in and out. Tiny surges were being sent out and touching my pussy and making me feel a warm glow deep inside my core. "Faster," I moaned. I arched my back even more so he could really push himself into me.

Jon increased his speed the sensations started to rev up. I started having flashbacks of my experience with Nicole; when she rapidly plunged a buttplug in and out my ass until I squirted and passed out. I felt a similar orgasm approaching me now.

My moans got louder. My breaths became shorter. I started chanting, "Oh fuck. Oh fuck." Jon kept his pace consistent until my orgasm hit me. I did not black out, but I screamed as my body convulsed under Jon. There was so much fluid coming out of my pussy, I might have squirted or was just incredibly wet.

Jon held himself still in my ass until the orgasm subsided. Then he pulled out and crawled off me. I turned, and in between deep breaths exclaimed, "We aren't done yet, are we?"

He smiled and asked, "You want more of that?"

I shook my head violently. "Yes please."

"I thought you might. But I want you on top so you can control the depth."

I rolled over to the side of the bed and Jon took my place in the middle. It almost took more energy than I had to crawl on top of him, but I did. He pointed to the edge of the bed, suggesting that I refresh the lube.

I spent a few enjoyable minutes making his huge cock slippery once more before cleaning my hands on the towel. It also allowed me to recover a bit of my lost energy. I lifted and took his giant erection and aimed it at my gaping ass and slid down. I string of explicatives escaped me as the sensation of him splitting me open returned.

"Oh fuck! You are so big. God damn it." I could not help myself. Up and down, I went until the pleasure receptors kicked back in. Finally, I was happy again and moaning at how he was making me feel.

He pulled me down to him and kissed me deeply. My ability to ride such a big cock and kiss properly was being challenged. Finally, I pulled away, gasping for air. "I love your cock in my ass," was all I could mumble.

He smiled and replied, "Sit up and see how much you can fit in."

I sat up and started riding him with more intention. I tried and I tried to get more of him inside me, but it was as if I were blocked. It did not stop me from riding him hard until I had my second anal orgasm. This one was just as intense, and I fell forward letting the sensations surge through my body without constraint.

Once my orgasm was gone, I worked my way back up on my hands. I looked down upon Jon, my tussled hair falling into his face, and I smiled. He pulled me in for a kiss.

As we kissed, I felt him start rocking his hips up and down sliding his manhood in and out my ass again. I felt completely taken, with his sensual kiss melting me as usual; his strong arms wrapped around me pulling me into him, squishing my boobs into his chest. His thick cock pushing into the depths of my anal cavity.

Our kiss broke and I moaned into his face. He whispered, "As good as your ass feels, I want to feel your tight pussy. Can we switch?" I helplessly nodded my agreement. He rolled us over and before I knew it, he was sliding in and out of my ass as I lie on my back.

I looked up at him and he smiled back at me. "You really do like my cock in your ass, don't you?"

I smiled and nodded yes. He continued, "Would you prefer that I finish in your ass right now?"

I had an unexpected moment of clarity. "Do I have to choose between that and feeling you inside my pussy?"

He nodded, "Given our time constraints and the fact that your sexy body is making me want to cum soon, then yes."

"Then I want to switch. I want to feel you cum inside my pussy."

He smiled and pulled himself out of my ass. For the first time in several minutes, I felt that emptiness again. As he cleaned up and refreshed the lube on his cock I asked, "How deep did you get?"

He threw the towel back to the corner of the bed and replied, "A little more than half."

I got caught up in wondering how I would ever fit the other half of his manhood in my ass. He broke me out of my trance when he leaned down and kissed me. Several sweet kisses soon turned into another sensual kiss. I relaxed again enjoying his tongue gently tangle with mine.

I moaned through our kiss as I felt his cockhead press against my pussy hole. Even though I was wet, and he was slippery, it still took my breath away to feel him split my tiny pussy. He took my head in his hands and started kissing my neck as he slowly moved the head of cock in and out of my entrance.

His teasing only made me hornier; I wanted him more than I had ever wanted anything in the world. I exhaled, "Please!"

Jon pushed himself into me a few inches and I groaned. My pussy gripped him as if it were trying to pull him in deeper. I wanted him and told him so. "You feel so good. Give me more," I expressed.

Slowly and methodically, he fed me more of his manhood as I wrapped my arms and my legs around him. I had multiple orgasms, one after the other, over the course of several minutes. It was then that I truly felt what intimacy was like.

He pushed himself up onto his knees and pushed my legs farther back. He picked up the pace a little. I could feel him through my entire body as it tensed. My fingers and toes curled. Without thinking about it, I started gripping the sheets. I tilted my hips forward trying to entice him to go deeper.

He pounded my pussy deep and hard. Our grunts competed for domination. I held off the little orgasms fighting to come out. I wanted us to cum together, as one. Jon fell forward onto his hands and kept his pelvis pushing into me, driving me into the bed. The whole building may have heard our noises.

Jon exclaimed, "Here it comes. Here it comes!" With one final push he let out all his air, "Ahh!" I felt his cock pulse hard one time and I started to cum with him. My body started to convulse and spasm. I felt my pussy grip onto him like a vice. Time slowed down and I could feel each cum shot as it raced down his shaft, out the head of his cock, and pound into the back walls of my pussy.

I pulled him into my embrace, wrapping my arms and legs around him again. We were one as we shared a powerful mutual orgasm.

We lay there, breathing hard, with me wrapped around him, refusing to let go, treasuring the last feelings of him inside me. Together we expressed, "That was amazing," followed by a laugh.

I loosened my grip enough for him to come up a little. He met my loving gaze and kissed me. It was sensual and amazing, like everything about him. He finished kissing me and pulled away enough to look down upon me again. I commented, "Thank you for making me feel so good."