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Jack experiences his best orgasm to date.
My full time job is as a female medical assistant to a leading urologist in a major city. I sought out a career in this field mainly due to my fascination with penises. One of my patients recently hired me on the side to tutor his 16-year old son. The son, Jack, was painfully shy, had never dated, and the father felt he was in need of some sex education. Preferably hands-on sex education, which is why he hired me. The father, Robert, is extremely wealthy and paid me a ridiculous amount of money for two 2-hour classes a week at his home.

I was connecting with Robert’s son Jack for our fifth meeting. I had a special procedure that I wanted to show him. It was more of a training session actually. I planned on teaching him the fine art of edging. I would give him a training lesson in proper edging and then in the future he could perform it himself. Jack was waiting for me in the examination room that his father had set up in their large home specifically as a place where I could hold my twice-weekly two-hour sessions with Jack.

For those readers not familiar with edging it’s the practice where the penis is stimulated by masturbation right to the point of orgasm, and then stopped before ejaculation. Tthe masturbation procedure is halted until the immediate urge to ejaculate passes. Once that occurs, masturbation of the penis is resumed until the urge returns and then it is stopped again. This procedure can be repeated over and over as many times as is possible without actually cumming.

The process has a two-fold purpose. One, the repeated lengthy masturbation of the penis feels wonderful to the person being masturbated. Two, once orgasm is finally permitted, the volume of semen that is ejaculated is much greater than usual and the force with which it is spurted out can result in some very impressive cumshots. And best of all, the orgasm itself will be unbelievably pleasurable. It can be several orders of magnitude greater than an ordinary orgasm.

The challenge, of course, is to avoid actually achieving orgasm for as long as possible, which can be very difficult. Sometimes just one extra stroke on the subject’s penis can result in ejaculation.

As I walked into the exam room, Jack was sitting on the examination table completely nude. And as usual he already had a very impressive erection. His large penis jutted straight up from between his legs with his very prominent glans on display. I found Jack’s penis to be unusually appealing. I have seen a great many cocks in my line of work but I can honestly say that looking at young Jack’s penis really got my juices flowing.

“Well, Jack, it looks like you have started the party without me,” I said.

“I hope it’s ok Miss Kelly. I know that our sessions always have me undressed so I thought I would save time and be ready for when you arrived,” Jack replied.

He was right of course. But I have to admit that I was a bit disappointed that he was already hard. I was hoping that at one of these sessions he would be totally flaccid and I could enjoy massaging his cock in the soft state and bringing his magnificent penis to a fully erect condition. Having done that to hundreds of cocks in my profession I got an extra thrill with the process of taking a soft cock to full hardness. Of course since Jack was only 16 years old, just his anticipation of what was to take place in one of our sessions would have his young cock rock hard in seconds all on its own. The chances of me ever even seeing it soft were slim. Even after jacking or sucking him to orgasm, his cock never seemed to totally deflate.

“Don’t worry about it Jack. I’m glad you fully prepared yourself for our meeting,” I lied. “Here’s what we are going to do today. I want to commit the entire first hour of our session to this exercise. I will have you lay back and I will start masturbating your erect penis. However, when you feel like you are about to cum, I will stop and let you rest. After a minute or so I will resume masturbating you and again, once you are close, we will stop. Now it’s very important that you don’t cum. We did something similar to this once before but not for as long as I want to do it this time.”

“You mean you are going to spend a whole hour jerking me off without me cumming?”

“That’s correct. I have a very good sense when a man is about to cum while I am masturbating him. But young boys like yourself can be very quick on the trigger so I will need your help in having me stop in time. The result of this procedure is at the end of the hour when I bring you to full orgasm, it will be the most intense and pleasurable orgasm you have ever experienced. You will also have the most impressive cumshot ever, both in volume and distance. A huge amount of cum will spurt from your penis and it will likely shoot halfway across the room.”

“Wow,” Jack exclaimed. “That sounds wonderful. I love it when you jack my cock. You really know how to make it feel so good. I can’t even imagine you doing me for a whole hour. I hope I can hold off for that long.”

“Ok, please lay back and let’s get started.”

As the boy lay back, I grasped his penis with just the tips of my fingers and gently massaged the huge knob end of his cock. I was literally obsessed with this boy’s dick. I stared at it, unable to take my eyes off of it. As I continued to massage the head, I was mesmerized by the tightness of the skin on the head of his engorged member. I have always been fascinated by how cockheads had an almost silky consistency to the skin on the glans and also how it had a deep purple color making the head of Jack’s cock stand out even more than it did due its sheer size. I leaned over and placed my nose directly above the head of his cock. I inhaled deeply and took in the slightly pissy odor that emanated from his penis. I loved that smell. As I rolled his foreskin back and forth his penis continued to give off that sexy fragrance that made my pussy tingle.

I was very tempted to take his cockhead in my mouth and see if it tasted as wonderful as it smelled. I remember the first time I took a freshly washed penis in my mouth and was both surprised and disappointed that it had no taste whatsoever. I have since learned that an unwashed cock has a slightly tangy taste to it that I have learned to love. I am sure Jack’s would have had had a great flavor but I was committed that this session be devoted to manual stimulation only. We would have a second hour where I could suck his cock to another orgasm or two. In fact I would make it a point after he reached orgasm as a result of the edging session to make sure that plenty of semen coated his cock so I could suck it clean.

In the meantime I had a full sixty minutes to devote to stroking and massaging his penis. I always looked forward to manipulating Jack’s cock. One reason was its hardness. I had handled a great many erect cocks in my day but I am certain that Jack achieved a level of hardness that no other prick I had ever stroked came even close to. It was so stiff that if I pulled down on it, it barely moved. It was my job to provide a level of stimulation over the next hour that would keep it in that state 100% of the time.

As I manipulated Jack’s foreskin back and forth along the length of his cock I marveled at how the knob head literally popped into view each time I pulled the foreskin back and exposed the head. It took every bit of will power I had to keep from planting a big wet kiss on his glans each time it popped into view.

I swirled my fingertips around under the coronal ridge, which was very prominent on Jack’s member. I knew that was the area of greatest sensitivity. I could tell it felt wonderful to him as his body squirmed and bucked beneath me. As I massaged that special area with one hand, my other hand gently jacked the shaft.

“Are you getting close to cumming?” I asked.

“Oh Miss Kelly, it feels so wonderful I don’t want you to stop, but if you don’t, I’m gong to cum,” he groaned.

I stopped all movement but continued to tightly hold onto the shaft of his cock. With my hand wrapped around the shaft that huge cockhead protruded out of my fist. It had even deepened in color from when we started. By the time we finished it would be bright red. I leaned over and inhaled the scent of his cock again.

“What are you doing, Miss Kelly?” he choked out. “Are you smelling my dick?”

“Yes, and it smells wonderful,” I replied as I pulled his foreskin fully back and got another whiff of his cock’s pissy fragrance. “Smells and tastes are an important part of sex as you will learn.”

“I think I already learned a bit. That time in our first meeting when you let me fuck you, I got a faint smell of your pussy and it really turned me on. I can’t wait to smell it again.”

“You will get your chance. Don’t worry. And what’s more, you will get to taste it as well and I am sure you will love it.”

By now I had drizzled some lubricant all over the head and shaft of his organ. Once it was fully lubricated, I proceeded to masturbate his cock using both hands. With one hand I wrapped my fingers around that huge knob head and massaged it while my other hand jacked the slippery shaft. I twisted and turned my hand wrapped around the head. I knew Jack wouldn’t be able to withstand my ministrations for long and within a few minutes he was bucking and squirming and crying out that he was about to cum. Again I stopped and just held his dick motionless.

Next I let his dick flop back on his stomach and focused my attention on the frenulum, that area on the underside of the penis just below the head. There was a raised seam of flesh there that was about ¾-inch long. I knew this little ridge of skin was a super sensitive area. I kneaded and fondled his nutsack with one hand while I ran the tips of two fingers up and down that ridge of skin. I only did this for a minute or two and then stopped to give him time to calm down. Then I resumed rubbing that area. His poor cock was throbbing and pulsating with pleasure. I knew I couldn’t keep this up too long or the semen would be spurting forth.

I had a dish of warm water next to the exam table and if the lube on his cock and my hands started to dry out I just dipped my fingers in the water and the original super slippery condition returned. Eventually I would squirt a bit more lubricant on his dick.

Next, I decided to slip a finger up his anus and fingerfuck his butthole. I had to be very careful with this maneuver because it could easily cause him to ejaculate all over the place. When he felt my lubricated finger searching for his entrance he spread his legs and raised his butt off the table to give me the best access possible. He loved having my finger up his ass.

The room had one of those big commercial wall clocks and I was keeping an eye on the time. By now 55 minutes had gone by since I had started masturbating and edging him. He kept crying out for a release. I was very impressed that we had managed to go this long without him spewing semen all over himself as well as me. I didn’t really care at that point. I just wanted to see him cum. I was really looking forward to seeing just how powerful and voluminous his ejaculation turned out to be. I knew it would be big.

“Are you ready to cum, Jack,” I asked, knowing what the answer would be. He had been ready to cum for the past 50 minutes.

“Omigod, Miss Kelly, please make me cum. I can’t wait to shoot this big load. I know it will be huge. Make me cum!”

With that I began pumping my finger in and out of his ass and jacking the shaft of his cock as hard and as fast as possible. My little hand was a blur flying up and down his prick. I also was gripping it about as tight as I could. As suspected, it didn’t take long before a fountain of jism erupted from his magnificent cock. It shot straight up in the air and splattered back all over his chest, stomach and cockÔÇŽeven on his thighs. And it liberally coated my hands and arms. Honestly I had never seen one cock spew out that much boy goo. The semen smell was overwhelming but I loved it. And the more I jacked and pumped his dick, the more semen that kept spurting out. It just kept cumming and cumming just like in those phony cumblast videos. But this was real cum, not the fake stuff used in the videos.

I knew Jack was experiencing the best orgasm of his life. His hips bounced up and down off of the table as he fucked my fist. He was actually screaming out to me telling me to make him cum and yelling the word “fuck” over and over. He must have cried out “I’m cumming” about ten times while the semen spurted from his cock.

As long as the semen kept squirting out I continued to furiously jack his erect prick. Finally it had dwindled down to just a few stray drops that I was able to milk out.

Jack was so out of breath he could barely talk. “Oh Miss Kelly, that was definitely worth an hour of torture. You have given me many great orgasms but that was unbelievable. The orgasm feeling just lasted forever like it was never going to stop. But sadly it did.”

“All good things must come to an end,” I replied. “Here, let me clean you up.” I leaned over and took his still rockhard penis in my mouth and sucked that huge cum covered knob end. After sucking the head clean I got as much of his cock down my throat as possible but then had to finish cleaning off the part I couldn’t get in my mouth by licking the cum off. There was so much cum on him as well as me that I had to get some towels I kept handy just for this purpose and wiped as much off as I could. Finally I gave up and told him to step into the shower that was adjacent to the exam room. I was able to wash off my hands and arms.

After he finished showering and toweling off I noticed that amazingly his dick was still about half hard. Oh, the joys of being a teen aged boy. I had him lay back down on the exam table and I proceeded to suck his cock. Despite the huge cumshot he just experienced I knew I could bring him off again. It only took about 15 minutes and another load of cum erupted, this time down my throat. I finished off the second hour by stripping my clothes off and climbing up on the table with him. I straddled him and positioned my dripping wet pussy directly over his massive piece of rock hard meat. I grabbed his dick and directed it right into my pussy. I spent the next 30 minutes very slowly and gently pumping my body up and down on his cock. My wet slippery pussy was juiced to the max. I probably orgasmed at least six or seven times and finally he also came and unloaded another load of boy juice into my eager pussy.

Jack didn’t see him, but I noticed his dad Robert standing in the doorway watching us as Jack’s big cock flopped out of my pussy, completely covered in my pussy juice with semen drooling out of that huge cockhead and running down my leg. Robert unzipped his pants and pulled out his hard penis and started jacking off. Amazingly it didn’t take long before he reached an orgasm and spurted his cum all over the floor. He didn’t make any attempt to clean up his cock, just stuffed it back in his pants, zipped up and slipped out the door. I wondered how I was going to get Jack out the door without him seeing his dad’s cum all over the floor. By now Jack was about half out of it from so many cum blasts that I figured I could maneuver him around the puddle of cum and out the door. Which I was able to do.

The good thing about Robert seeing us and jacking off is I could probably skip giving him the blowjob that he liked to have after I finished my session with his boy. I really didn’t mind sucking him off. He had a cock almost as nice as Jack’s and I loved sucking it.

Robert told me later that Jack was so loud when he came that he heard everything Jack said and knew he was having the orgasm of his life. Robert said that listening to Jack’s cries gave him a hard on and he had to come in and see what we were doing. I had locked the door but Robert had a key. And once he saw what we were doing and saw Jack’s big wet cock slip out of my pussy, he couldn’t control himself and had to jack off. He apologized for leaving a big puddle of cum on the floor but I told him not to worry about it. By now all the household staff knew what was going on and I would have the housekeeper clean it up. I had cleaned up enough jism for one day.

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