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Introduction:

Teenaged Jack meets the second woman who is interested in his genitals.

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.

After Jack had several sessions with Miss Kelly, he had an experience with one of the staff that worked for his father. The following is told by Jack:

My dad has an all female staff that works for him at our house. There is a maid, a housekeeper, a chef, chef’s assistant, and the driver. All are women and mostly young and very attractive. After mom died, dad wanted to at least have some nice eye candy in the house at all times. I am pretty sure he wasn’t banging any of them. But it did make things more pleasant around the house.

One day the maid, who is named Ellen, and who is 28 years old, and extremely attractive, approached me while I was in my room. She seemed a bit hesitant but I asked her what she needed.

“Jack, I am somewhat hesitant to mention this but I accidentally saw you in the nude the other day. I couldn’t help noticing that you have a very unusual penis.” She saw the shock and embarrassment on my face. “No, no,” she said, “it’s nothing to be concerned about. I was quite impressed with the size and that large glans is very appealing.”

I was somewhat relieved when she said this because I’ve long been ashamed of my freaky looking dick. I’ve been very shy about letting anybody see it.

“I’m taking classes at night school,” she said. “I am majoring in anatomy and frankly I find your penis very interesting. Because it is so unusual I have a very unorthodox proposal. Each student has to submit a paper or dissertation each semester focusing on a particular part of the anatomy and I would like to do a paper featuring your penis.”

“Isn’t your instructor going to think that’s kind of weird?” I stammered.

“It’s a legitimate subject. We’ve already covered male genitals in class but they didn’t go into much detail. I don’t care if he likes it or not. I want to do it.”

“What do I have to do?” The idea both intrigued and scared me.

“Well, I guess I need to closely examine your genitals and I’d also want to take some photos. Most of the submitted papers include photos and because of the unusual size of your glans…the technical term for your cock head…the paper wouldn’t mean much without photos. When I accidentally saw you nude, it looked like you had a bunched up foreskin right behind the glans. I would need to see that and discuss it with you.”

“When would we do this?” I said in a choked voice.

“I just went off the clock a few minutes ago and I’m off all afternoon so we could do it now,” she replied.

“Ok, what do I do?” I didn’t really think I was ready for this.

“You can take off your pants and underwear to start. And maybe lock the door to your room so we are not interrupted.”

I was very hesitant to show my cock to this woman. Up to now the only female to ever see it was Miss Kelly and she is a medical professional. That’s a lot different than showing it to the maid. I was also really worried that my cock was somewhat freakish with the huge head but Ellen didn’t seem to think so. Despite my fears, I took off my pants and underwear and stood before her with it all hanging out. My cock is quite large. Even soft. It’s about 6-1/2 inches long and very thick. Along with an unusually large head. When it gets hard it’s about 8-1/2-inches.

“Are you a shower or a grower?” Ellen asked me.

“I don’t know what that means,” I replied.

“A ‘shower’ is a large cock that doesn’t get much bigger when it becomes erect. A ‘grower’ is a penis that gets bigger when hard.”

“I guess I am a ‘shower’ and a ‘grower’ considering my cock starts off pretty big and just gets even bigger when I have an erection.”

“Ok,” Ellen said. “I have a few questions. With a glans that large do you have any trouble pulling your foreskin up over it?”

“Not when it’s soft. I am partially circumcised so even when I pull the foreskin forward, it doesn’t cover the entire head. The tip still is exposed.”

“Interesting. Can you demonstrate that for me?” she asked.

I rolled the foreskin forward and showed her how it only covered most of the head. Then she asked me to retract my foreskin. And I did. When the foreskin pulled back off the head, the head kind of popped into view. She found this very intriguing and asked me to do it again. And again. So basically I was masturbating my cock for her and the inevitable happened. I got an erection. I apologized. I was mortified.

“Don’t worry Jack. In order for me to gain the necessary information to write my paper I would need to see it in the erect state in any event so don’t concern yourself about it. Please continue to roll your foreskin forward and back. I want to see how difficult that becomes now that your penis is fully erect. And I must say that is an extremely impressive erection. I’ve never seen a cock that large before. Keep it hard for me while I get some photos of it to use with my dissertation.”

I continued to masturbate my prick for her. It felt really good now that it was fully hard. She got her camera phone out and took several close-up photos of my erect cock.

“It appears to be more difficult to get the foreskin to roll up over the enlarged head,” she commented.

“Before Dad had me see a doctor about it, it was almost impossible to get the foreskin all the way forward when my dick got hard. But the doctor did some minor surgery on my foreskin that loosened things up a bit, but it’s still kinda tight.”

“Do you mind if I check it myself,” she asked.

I told her to go ahead and she took over masturbating me. Each time she pulled the foreskin back and my large cock head popped into view she let out a little giggle. “Jack, I really love the way the head of your cock jumps into view. It makes my pussy tingle.”

Did I hear her right? Did she say my dick makes her pussy tingle? I was already overly excited from having my dick stroked but when she said that, I couldn’t hold back and semen spurted from my cock. I expected her to release my cock like it was a hot potato but just the opposite happened. She increased her grip on my cock and pumped it even faster. More and more cum shot out splattering all over the carpet on the floor. I was in total ecstasy and didn’t even worry about the mess I was making. Finally the streams of semen abated but she continued to milk my dick forcing a few more drops out. She leaned forward and licked off the last dollop of cum that she squeezed out.

“Well, Jack,” she said, with wonder in her voice. “That was quite a display of manhood. I really wasn’t expecting you to have an orgasm. I had forgotten how easy it is to make a teen boy ejaculate. I bet that felt really good, didn’t it? And don't worry about all that cum on the carpet. I can clean it up.”

“The best feeling in the world, Ellen. I’m sorry for shooting so quickly. I kind wish it had lasted longer. It felt wonderful when you were stroking me.” Which she was continuing to do.

“If I keep stroking your cock, can you ejaculate a second time?”

“No problem,” I replied. “I’ve jacked off three or four times in a row.”

“Since you didn’t think that first handjob lasted long enough, maybe I can make this second one last a lot longer.”

With that she started pumping my cock again but this time she fondled my nutsack which really felt super good. Every so often she would stop jacking me off and she would force the head of my cock into her mouth and sucked me. Omigod, that felt amazing. Miss Kelly had sucked my cock and she was really good. But so was Ellen. Maybe not as good as Miss Kelly but Ellen had a slightly different technique that really felt fantastic.

She continued to alternate between jacking me off and sucking the head of my dick, occasionally stopping or slowing down to make it last. It was the most incredible feeling a boy could experience. Her hands were so soft and my dick was so hard.

She somehow sensed when I was about to cum again and took me into her mouth and sucked the head while she jacked the shaft and massaged my nuts. My whole body tensed. I grabbed her head in both hands and forced my cock in and out of her mouth. Actually it was just the head of my cock because that was all that would fit. And the inevitable happened. I forcefully ejaculated an amazing number of shots of semen down her throat. I thought the first orgasm was fantastic but this one was even better. Somehow she managed to swallow all of my cum. I finally let my cock slip out of her mouth. She took it in her hand and gently continued to massage the head.

“Jack, I hope that was a satisfying orgasm for you. It’s never happened to me before but I actually came while I was sucking you off. It always takes some actual contact to my clit to make me cum but not this time.

“So do you think you have enough info to write your paper?” I asked.

“Oh, no,” she replied. “It will take several more sessions like this one to get all I need.”

“Are you going to write about jacking me off and sucking my cock?” I asked worriedly.

“Oh no,” she replied quickly. “That has to be our secret. I could get in a lot of trouble if anybody knew I was having any kind of sexual contact with a boy your age.”

I didn’t tell Miss Kelly about my interlude with Ellen. I didn’t think she would approve of me having sexual contact with any of the staff. Little did I know about the future plans she had for me, as well as for my dad, with respect to interaction with the staff. But I would soon find out.

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