I took hold of his penis and pulled the foreskin back. He had a very prominent coronal ridge on an unusually large glans. While the penile shaft itself had considerable girth, the glans was much larger which provided more tactile area than normally found on a penis. I massaged this area with my fingertips and immediately felt his penis start to enlarge.
“What are you doing?” he exclaimed. “Should you be doing that?” His face was flushed and I could tell he was terribly embarrassed to have a strange woman massaging his cock. He had no control over his penis. I am sure he would have preferred it to stay soft but my ministrations had achieved a full-on rock hard erection. After it was fully erect I proceeded to start jacking his shaft, rolling his foreskin all the way back and then up over the head.
Jack’s eyes closed and his head lolled back. No man or boy could resist the sensations that I was providing his penis. I hadn’t planned to bring him to orgasm until after at least two or three meetings but those plans were dashed as a fountain of semen erupted from his teenage cock. As I furiously pumped his big thick cock, spurts of boy juice continued to forcefully shoot from the tip. I was totally unprepared for his orgasm so the cum went everywhere. I really hadn’t had much experience with boys this age. Even when I was younger, most of my sex was with older men. Although I knew that teens didn’t take much stimulation to reach orgasm, I still was not prepared for it. So as not to diminish his orgasm in any way, I continued to pump his prick until he was totally devoid of semen. At least for this round. I also knew young boys could come right back for a second or third orgasm, or even more. Now that we had broken the ice so to speak, I was sure that getting another few orgasms out of him would be no trouble.
By now he was lying prone on the exam table gasping for breath. I released his penis, which maintained its hardness and was now sticking straight up. It looked out of proportion to the size of his teenage body. I had laid in a large supply of hand cloths and towels for clean-up but didn’t realize I would need them so soon. While Jack recovered, I started the clean-up task, which took a while because there was literally semen everywhere. It was all over him, all over me, on the exam table, and on the floor. I even found a few droplets on a nearby chair.
While I wiped up his cum, he started to apologize. I walked over to him and took hold of his cock. “Jack, there is no need to apologize. You did nothing wrong. What happened was totally normal. When a woman or girl stimulates your penis, as I did to yours, there is only one result that will happen. Cum is going to squirt out of your penis. As our sessions continue you will learn that your cock and I will be forming a very nice relationship. I know what happened was quite a shock to you and probably embarrassing. But that was just the beginning of what I know will be a very satisfying connection between your penis and me. I will teach you all the ways that a man, or boy in your case, will be able to achieve orgasm. Your embarrassment will totally disappear and you will eagerly look forward to the ministrations that I will be applying to your manhood.”
“Are you sure that it’s ok for you to jack me off?” he asked.
“Jack, I am a trained medical professional. I have been hired by your father to advance your sexual knowledge and prepare you for the various sexual scenarios that you will face as you mature. I hope you understand. During our sessions over the next couple of weeks I will be providing your penis with a variety of stimulations. Each week my goal will be to drain your system of as much semen as possible. Does that sound ok to you?”
“Well…uh…I guess so. Does that mean you are going to get me to cum again tonight?”
“Yes, at least two more times. We will start off with just three orgasms in this session. By the end of our last session I hope to get you to ejaculate at least five times during the two-hour session. Maybe even six times if you are up for it. Most teenage boys have no problem doing that. I bet you’ve jacked off more than that in one day. Plus I have some additional enhancements that will help.”
“What do you mean by ‘enhancements’?” He had a worried look on his face.
“Don’t be concerned. Everything I will be doing is to increase your pleasure. I guarantee you will love it. Now it’s time to continue. I want you to just lay back like you are now.” I climbed up on the table with him and kneeled between his legs. I had decided on these early sessions to remain fully clothed. As we progress to later sessions I will likely remove my clothing.
Jack’s penis was still semi-hard. I grasped the base of his shaft, leaned over and sucked the large head of his cock into my mouth. Jack loudly drew in his breath when my lips closed over his glans. I ran my tongue around the coronal ridge where I knew he was super sensitive. His cock quickly returned to a full-on steel hard erection. I lightly jacked the shaft with one hand while I fondled his testicles with my other. I loved to suck a thick cock. Especially one with a large head like Jack’s. I knew that the many men I had sucked off considered me a world-class cocksucker. I started to apply more suction pressure to the head of his cock and then let my lips slide down over the head and onto the shaft. I began to deep throat his cock while it swelled to a very impressive size. I then backed off a bit and slowed down. I wanted this to last as I was really in heaven with his big penis tickling my tonsils. I knew if I applied too much pressure he would be cumming again in no time.
With my extensive experience I knew just how far to take him without his cum shooting out. I managed to make the blowjob last almost 30 minutes. By then he was begging me to let him shoot his load. I sucked his cock right to the balls and then started bobbing my head up and down as fast as I could. It didn’t take long to achieve my goal as a massive explosion of cum shot down my throat. I could feel each spurt slam against my throat as his cock convulsed and his body bucked in orgasmic ecstasy. And a rare thing happened. I also experienced an exquisite orgasm myself as I greedily swallowed one of the largest volumes of semen I had ever received. This surprised me because I had milked a very large load of cum out of his prick when I jacked him off. But teens can obviously recover in a very impressive manner.
As I raised me head and let his prick slip from my mouth, he had a look of wonderment on his face. “Is that the first time anybody has sucked your penis?” I asked, knowing that it was.
He could barely speak. “Oh god yes,” he murmured. “That was the best feeling in the world. I never knew anything could feel so good. Nobody has ever touched my penis before but me. And you have given me two fantastic experiences. Will we get to do this again?”
“Yes, many times,” I replied. We still have nearly an hour left in tonight’s session and I plan to have you experience at least one more orgasm. I want you to know that as a medical professional I am supposed to keep our sessions as clinical as possible but I have to compliment you one having one of the nicest cocks I have ever been exposed to. I really enjoyed both jacking you off and sucking you off.”