If you have been following my stories, you know that I am a young, attractive female medical assistant who works for a leading urologist in a major city. As this is written, I have had this position for three years which makes me 27. Not many women work in this field but frankly I chose it because of my fascination with the penis. And I get to see a great many of them. While most of our patients are older, we get enough young men and even virile middle-aged men, to keep it interesting for me.

Our medical group also specializes in erectile dysfunction (ED) and over the last year I have more or less become the “go to” person in the firm to treat these patients as I have had a very high degree of success. One recent patient who I had “cured” was back for a 3-month follow-up visit. This is routine and it’s basically to check that the patient continues to have success achieving an erection. When I entered the examination room the patient had already been prepared by one of the other assistants. He was sitting on the exam table wearing one of hospital gowns that we provide.

This exam was very simple. All I had to do was make sure that the patient could easily achieve an erection. I greeted my patient, who had been one of my favorites. He was fifty, in good shape, was good looking, and had a very impressive penis. I walked over to the table, moved his gown away from his lap and took hold of his penis. I expertly began to masturbate him and he quickly became hard. Very hard. I congratulated him on his ability to maintain the same level of erection ability that he had reached at the end of my treatment.

“Thanks, doc,” he said, “can you go ahead and bring me off? For some reason I really need a release this morning.”

“No problem,” I replied. “I always like to check that your ejaculatory ability is not diminished in any way.” I laid a large flat dish that we in the office jokingly call the “cum tray” in front of him and proceeded to masturbate him to orgasm. It didn’t take long as I am quite proficient in coaxing orgasms out of erect cocks. He spurted several long streams of semen onto the tray.

“Thanks doc, that was great. Listen,” he continued as I wiped the excess semen off his penis, “I have a proposition for you. I want to hire you to do some special tutoring for me during your time off.”

“I’m sorry, but I am not permitted to have any off-site contact with patients. That’s a hard and fast rule.”

“No, no…it’s not for me,” he protested. “It’s for my 16 year old son.”

“Your son suffers from ED? That would be most unusual.”

“No doc, he doesn’t have any trouble getting a hard-on as far as I know. But he’s painfully shy. Never had a date with a girl. Is extremely protective of anybody seeing his penis. Even his mother, when she was still alive, commented to me how he always covered himself to make sure nobody ever sees his penis. He’s never had any sex educations classes and I’ve never been able to work up the courage to have that ‘father-son’ discussion with him. I was hoping you could work with him a couple of evenings a week and see if you can draw him out of his shell.”

“I would have to get approval from the firm in order to do something like that. I will check with the doctor and see what he says. What kind of money are we talking about?” I asked. He threw out an hourly rate that stunned me. I knew this guy was extremely well off. I could tell by his clothes and his shoes that he had money. He told me he would like to see me do a couple of two hour sessions a week and if need be we could add on a third session if I thought it would help. Maybe do this for three or four weeks or however long it took. This added up to almost as much money as I made with my doctor.

Surprisingly my doctor had no objection and I worked out a schedule with the boy’s dad. At his suggestion he set up an unused bedroom in his sprawling mansion to basically duplicate one of our examination rooms. We both agreed that the boy might feel a bit more comfortable in what looked like a medical environment. I would wear one of my white medical smocks.

Our first session was then scheduled. I showed up at the extremely impressive house located in a very high-end neighborhood. The dad introduced me to the son, who was named Jack. I told Jack that he could call me Kelly. The dad explained that I was basically a health professional that was going to help educate the boy in areas not adequately provided by the school he attended.

The dad then showed me the room that had been prepared and left Jack and me alone. I asked Jack to sit on the exam table while I attempted to explain in general terms what we would be doing. I took my time getting to any discussion about sex education but when I finally brought the subject up, the boy’s face turned crimson. I knew I had to somehow calm him down before the whole thing went off the rails.

“Jack, I understand your concern about getting into areas that are totally new to you. But keep in mind that I am a medical professional who only deals with men. Men, who most of the time totally disrobe for my inspection. So please just relax and allow me to do my job.”

“What kind of inspection are you talking about?” he wanted to know. Real concern showed in his voice. “Am I going to have to get undressed?”

I had planned to hold off any undressing until the second or third session but now that the subject was broached, I felt it best to get right into it before he had a chance to back out of the program.

“Well Jack,” I replied, “the undressing was planned to be later but I think as an ice-breaker it might be best if we get right to it.”

“You mean you want me to take off my clothes now?”

“Yes, here is a hospital gown. Please go behind that screen and remove all your clothing and put on this gown. The gown can go on either way but please put it on so the front is open. There is a place to hang your clothes behind the screen. Take off your shoes and socks as well as I plan to give you a complete medical checkup.”

He very reluctantly went behind the screen and a few minutes later came out in the gown. He had the front tied tightly together with the ties. After he sat down on the exam table I went over and untied the gown. As I pulled the front open he put his hands down over his penis.

“Jack, in my job I see hundreds of penises. So please don’t be shy about showing yours as it is nothing new to me and will be necessary for what we are doing. In fact, let’s start the exam off with me inspecting your genitals.” With that I pulled his hands away from his crotch to reveal an extremely attractive penis. I was surprised to see it was even larger than his dad’s. He had what is known as a “German Cut” circumcision where only the excess skin extending beyond the glans is removed. When flaccid this foreskin covers most of the glans with the tip still exposed. From my experience, I knew that in most cases when the penis became erect, the foreskin would roll back all on its own fully exposing the head.

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.”

“Thank you Miss Kelly. That makes me feel really good to know that you like my prick that much. For my next orgasm, are you going to jack me or suck me off?”

“This time it will likely be both.” My session plans were totally blown to hell. I hadn’t planned to be at this stage until at least our third session. And despite my best intentions, I was about to throw the whole plan under the bus. “Or we have another alternative. How would you feel about fucking me? I really have a craving to feel that big cock of yours inside me. I have never fucked a penis with a head as large as yours and I am super curious to see what it will feel like.”

“Omigod, are you serious? Of course I would love to fuck you. I’ve fantasized hundreds of times about fucking some of the hot girls in my school but figured it could never happen. I’ve jacked off many times fantasizing that my fingers were some girl’s hot pussy wrapped around my prick.”

His cock was drooling some semen and I leaned over and licked it clean. Then I let his cockhead slip into my mouth. We lay there together for about five minutes with me just lolling his penis around in my mouth but not really sucking it. I let my tongue roll over the head of his cock and felt it start to harden. I then began to lightly suck on the head until he was fully hard. Fortunately the exam table his dad had purchased was an extra wide one so there was enough room for us both. I jumped off the table and quickly removed my clothes as he pulled off the hospital gown. Now we were both naked. I climbed back on the table and gave him about a minute’s worth of cock sucking to make sure he was fully hard. I had picked up a bottle of K-Y lubricant and liberally coated his penis and the opening of my vagina with it. I then straddled him placing my vagina directly above his distended penis.

“I am going to control the penetration,” I explained. “Otherwise your big cock might hurt me if you get too excited.” I held the lips of my pussy open with one hand while I guided that big head to my opening. I started to slide my pussy down over his prick. It started in but then it stopped. It felt glorious but I knew I might be too tight for him. But I was determined to get that penis inside me. I rocked up and down and I could feel it almost wanting to pop past my opening and penetrate me. It was hurting me by stretching my opening but I didn’t care. Finally, I thrust down as hard as I could and his cock went in about six inches. That’s all I allowed on the first thrust. He groaned in ecstasy but I am sure it felt even better for me. His cock was about eight and a half inches long so there was still more to take. I wanted it all even though I knew it would be bumping against my cervix. I began to thrust up and down, starting off with 6-inch strokes but then I let each stroke go a bit further. One thing that helped is I was so damn charged up that my pussy was working overtime producing lubricating juice. I was sopping wet. But that just enhanced the pleasure for both of us. After a flurry of strokes I was taking his entire length. Each time he bottomed out on my cervix I felt a stab of pain. But it was a good pain and I was loving it.

I was in a sexual frenzy and I pounded up and down on that glorious cock as furiously as possible. I was on my third orgasm when Jack let out a scream of ecstasy and poured a load of semen into my greedy pussy. His screams were really loud and I wondered what his dad must be thinking. The house was pretty big so maybe he didn’t hear it.

But I heard a door open and looked back over my shoulder to see his dad standing in the doorway. He had a strange expression on his face. A mixture of shock and pleasure. He had a great view of his son’s big cock splitting my tight pussy. Semen was running out of my cunt onto his son’s ball sack. I smiled at him and he smiled back and quietly closed the door. I’m not sure Jack was even aware that his dad had opened the door. He was too far gone in his orgasmic bliss.

We lay there together like two exhausted lovers for about 15 minutes. There was one of those big round clocks up on the wall and I could see our time was just about up. I slowly raised up and felt Jack’s big semi-hard cock slide out of me. It flopped back on his stomach. I hopped off the table and bent over Jack and took his cock in my mouth and sucked his semen and my juices off.

“Oh god, Miss Kelly, I thought that blowjob was the greatest feeling I ever had but fucking you was even better.”

“Yep,” I replied, “that was definitely a really great fuck. I don’t think I have ever had a more satisfying fuck and that was almost all due to that magnificent cock of yours. I never knew what a difference a big head like yours makes in the way it feels as it pumps in and out of me. Just fabulous.”

“We will get to do it again, won’t we?”

“Oh for sure. Many times, but just not tonight. Time’s up.”

“It’s been two hours already? I cant’ believe the time went by so fast. I was really hoping you could make me cum again. I’m ready. I know I could do it again.”

I looked at the clock. We had about ten minutes. I grabbed the bottle of lube and coated his cock and one of my fingers. I started masturbating him while sliding my lubed finger up his anus. It didn’t even take two minutes and his prick was spurting out even more semen. Obviously not as much as the first three times and a bit more watery but still an impressive display.

“How’s that,” I asked. “Feeling better?”

“Thank you so much Miss Kelly. You really know how to make a boy feel great.”

I was confident that our session had provided Jack with a lot more confidence and self-assurance. Any shyness was totally gone and it was obvious he was quite proud of himself. Then we both got dressed and he went to his room and I went to the living room where his dad was waiting.

We were both a bit embarrassed but I broke the ice first. “I think we made great progress tonight. I can guarantee that a lot of your son’s shyness is gone. He’s definitely not concerned about displaying his penis. And frankly he is a very good sex partner considering he’s never had any kind of experience with anybody. As you no doubt saw.”

“I’m sorry I barged in on you but when I heard him screaming, I was very concerned that something had gone wrong. But I must say I was a bit jealous. You did some great work with me in overcoming my ED with some exquisite hand jobs and blowjobs. But you never fucked me and here you were fucking my son less than two hours after you met him.”

“ We kind of built up to it. I started him off with a masturbation session and then to oral sex. And full coitus just seemed like a natural progression. Plus I really wanted to see what it felt like taking that huge knob of a cockhead that he has. I guess you’ve never seen him hard but he has one of the largest cockheads I’ve ever seen and I was dying to find out what it felt like.”

“And…?” he replied.

“It felt amazing. I’ve had quite a few cocks in me but that was by far the best feeling fuck I’ve ever had. I think I came three times. “

“And I suppose you will want to do it again with him?”

“As long as you keep paying me, I will be back here at least twice a week and fuck your boy until he can’t stand up.”

“I know this isn’t part of the arrangement, but talking about all this sex stuff has made me hard as a rock. Do you think you could jack me off?”

“How about a blowjob? Makes no mess that way. Take your cock out and let me at it.” Before I even finished telling him this, he was unzipping his pants and fishing out his engorged penis.

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