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 is extremely wealthy and paid me a ridiculous amount of money for two 2-hour classes a week at his home. The boy’s father thought that it might take a couple of months to achieve the desired results. The dad had even turned one of the home’s many bedrooms into a duplicate of a medical examination room where I conducted classes with the son.

Our first class was successful beyond anyone’s expectations. I had originally planned that in the first class I would verbally lay out the preliminary groundwork for what was to take place in future classes where more hands-on instruction would take place. But somehow those plans got derailed and we immediately got into the hands-on stage. I masturbated the boy to a spectacular orgasm, then I proceeded to gratify him orally. The son had an extremely attractive large penis with an amazingly large cockhead. The largest I had ever seen and at that point in my life I had seen a lot of cockheads. An overwhelming curiosity as to what that knob headed cock would feel like inside my vagina led me to end the session with the boy’s penis buried deep in my cunt. Actually, that’s not quite accurate. Even after three terrific orgasms, the young man was still rock hard and begged me for a release. So I jacked him off to a fourth orgasm.

An hour prior to the next scheduled session, I met with the boy’s father to discuss the future steps of the program. The father was fully aware of what had taken place in the first session. He had actually walked in on us when the boy’s penis was buried in my cunt.

“Miss Kelly,” the father said to me, “I want to congratulate you on the amazing changes in my boy after just one two hour session with you. A lot of his shyness is gone. He definitely has a lot more self-confidence. I had mentioned to you before how hesitant he was for anyone to see his penis. I never understood that but now that you told me about the overly large head on his penis, I assume he was somehow ashamed of the way it looked. Anyway, I have already gotten a complaint from one of the maids about him “accidentally” exposing his penis to her. After discussing it with him, I don’t think he purposely set out to expose himself but I think he no longer cares about any modesty.”

“That does sound like progress has been made,” I replied. “I was afraid that I had moved along too fast. I originally had hoped to lay some basic sex education groundwork but that got totally bypassed.”

“I guess some of that is necessary but it appears the hands-on approach is working so well that I would just stick with that.”

“I also have had some second thoughts that I have moved too fast.

What transpired at our first session was a lot to throw at a young boy all at once. It was all so easy for him that I am concerned that he might feel that sex with any woman, or girl, is more available to him than it really is. That could get him in a lot of trouble if he comes on too strong.”

“I can see why you might think that and it’s a valid point,” the father replied. “It will be up to you to educate him on what types of approaches to girls are appropriate and what isn’t. I would l like for you to continue on with him and I am ok with you engaging in any type of sexual contact with him that you feel is necessary for the advancement of his sex education.”

“Miss Kelly, we have a few minutes before your scheduled session with my son. Do you think you could spare enough time to suck me off?” As he said this, he unzipped his pants and took out a very large erect cock. I was pleased to see how quickly he had achieved an impressive hard-on. I had successfully treated him at the urologist’s office for erectile dysfunction. That’s how we met. And during our training sessions together I had masturbated him and orally serviced him multiple times in our journey together to solve his problem. So to see how quickly he got hard was very gratifying.

“Of course, Robert,” I replied. I am always willing to provide you the release you need.” Considering what this guy was paying me to train his boy, I would be more than happy to suck his cock any time he asked.

After swallowing his large deposit of semen down my throat, I had to get upstairs to the home’s pseudo examination room for the next scheduled session with the son. When I got to the room I was a bit surprised to find Jack sitting on the exam table totally naked with a very impressive erection.

“Hi Miss Kelly,” he exclaimed. He was obviously very happy to see me as his throbbing penis made abundantly clear. “What are we going to start off with?”

I had told him in the first session that I planned to bring him off to a minimum of three orgasms per classroom meeting. So he was obviously anxious to get started.

“I have a few questions for you. Since our last meeting a few days ago, have you been masturbating very much?”

“Yes, all that sex we had together really got me charged up. I have been beating my poor penis nearly to death. I haven’t jacked off at all today, however, as I wanted to save my cum for you.”

“That’s very considerate of you, Jack,” I replied. “I definitely enjoy large cumshots and I would hate to think that you wasted a lot of semen down the toilet bowl. Now let’s get started. When I masturbated you at the end of our first session, did you enjoy it when I inserted my finger up your anus?”

“Omigod, Miss Kelly,” he enthusiastically replied, “that was the best feeling ever. Especially when you pulled your finger out just as I started spewing my cum. That was great.”

“Ok, we are going to try something a little different this time but still involving my finger up your anus. I will put my finger up there and massage your prostate. I want to see if I can make you ejaculate with just a prostate massage and no actual contact with your penis. Now lay back on the examination table. Pull your legs up until your feet are flat on the table.”

I would normally wear a glove for this procedure but today it would be my bare hand. I liberally applied K-Y lubricant to his exposed anus and also on my index finger. I slid my finger up his anus and began to massage his prostate gland. I perform the majority of the prostate exams at the urologist’s office where I work and am considered an expert with the procedure. As I worked my finger in and out of his anus applying pressure on the prostate gland I watched his penis jerk and twitch. Jack let out a groan as I performed my magic.

“Oh, Miss Kelly,” he uttered. “I think I am going to pee.”

“That’s a natural reaction to what I am doing. Just ignore that feeling. You won’t pee but you will powerfully ejaculate a load of semen so be prepared.” As I said this, jets of semen shot out of his penis and splashed up his stomach and chest with the first blast actually hitting him in the face. His body bucked and reacted with a series of spasms with the intensity of his orgasm. I continued to massage his gland as long as the semen continued to spurt and drip from his cock. Finally I had milked most of it out. I pulled my finger out and wiped the lubricant from my finger and his butthole.

“Wow, that felt totally different from a regular orgasm,” he gasped. “Different, but still good.”

“I want you to experience all the different orgasms that can be produced with a variety of processes. I am glad you liked it. Now I have some questions for you. I know you must have seen a lot of porn online. Have you seen any particular act that you would like to try?”

“I did see something that really interested me. But maybe it’s kind of gay. I don’t know. But it was two guys who placed their cocks together and then a girl jacked both cocks at the same time until both guys shot their cum. I thought that was really hot. But of course there’s only me so we obviously can’t do that.”

“I could ask your dad. How would you feel about that? That cock-to-cock masturbation works best when both cocks are approximately the same size. Both you and your dad’s cock are roughly the same. Yours is a bit larger but the two are close enough that the two-cock jackoff will work quite well. Do you want me to ask him? Your dad is extremely liberal and will do anything for you.”

“Well, if you think he would be ok with it, I am willing to give it a try.”

I called his dad on the house phone and asked him to come up to the examination room. He wanted to know what’s up and I told him everything was ok but I needed him in the room. When he arrived I quickly explained what his son was interested in. While explaining the idea I stood by the exam table and lazily masturbated his boy’s penis.

“Wow,” he exclaimed, “that’s really an off-the-wall idea but it does sound like fun. Let’s do it.” He immediately started removing his clothes and by the time he was naked his penis was rock hard.

I had him get up on the table sitting facing his son who was also sitting. The two scooted close together with the dad putting his legs over the son’s legs. After some adjusting both ball sacks were touching and both cocks were standing straight up and dancing back and forth in anticipation of what was to come. I liberally coated both dicks and my hands with K-Y lubricant. Grasping both cocks with both hands I wrapped my fingers around the rock hard dicks and started jacking them. Occasionally I would slip a finger between both cocks so that additional friction was applied to the underside of them both, right where the sensitivity was the highest. I had performed cock-to-cock jackoff previously. Not at the office, but with a couple of casual boy friends. So I had some experience. We continued this for a good 15 or 20 minutes and by then I could tell they were both ready to cum. I started asking them both to cum for me, to shoot their jism all over my hands and sure enough the cum started spurting. The son was first but quickly followed by the dad. I must say that seeing two cocks side by side, both shooting streams of cum into the air with it splashing back down over both cocks as well as my hands was a glorious sight. So much so, that I experienced multiple voluntary orgasms. My own orgasms were so strong that it was a challenge to continue jacking those two magnificent pricks. But I hung in there despite being flooded with semen. I still gripped both cocks together. I had an overwhelming desire to take both cockheads in my mouth and suck all the cum off of them but of course that was anatomically impossible. I could just barely get the son’s huge cockhead in my mouth by itself. I settled for just licking the cum off of the heads of both cocks. My eager tongue laved over both pricks until every single drop of cum was gone. Then I took each prick and sucked it right to the balls going back and forth from each one until the boys begged for mercy. They said the feeling was too intense and they couldn’t take it.

I got some hand towels from the pile that were kept handy just for semen mop-up and wiped both boys clean. The father and son had collapsed onto their backs on the oversized exam table. They were both spent. I continued to idly play with both cocks while they recovered. Finally the father got up and started getting dressed.

“Damn, that was terrific. Thanks for inviting me. I hope we can do it again. Talk about father-son bonding. I can’t imagine anything else we could ever do that would equal that. I will leave you two to get back to your lessons.” With that he departed the room.

“What did you think, Jack?” I asked. Was it everything you expected?”

“Omigod, it was ten times better. And especially doing it with my dad was spectacular. Promise me we can do it again.”

“How about we make it a scheduled weekly event? With your dad’s approval of course.”

“I never knew there were so many enjoyable things I can do with my penis. I’m learning a whole new world and you are the best teacher a boy could ever have.”

“Thanks for the compliment. We are going to take a 15-minute break from the sex but I am going to lecture you on some various aspects of regular contact with women, or girls in your case. I have some slight concern that all the easy sex you are having with me might give you the idea that you could have similar relationships with other females. You can, of course, but only if the proper steps are taken. That’s what we are going to talk about now. Then I am going to suck your cock in as many different ways that I can think of. Sounds good?”

“Oh yes, Miss Kelly. I loved it last week when you sucked me off. I am really looking forward to it again. Will I get to fuck you today?

“I doubt if we will have time. The blowjob I will be giving you in a few minutes will be your third orgasm of the day. And the session with your dad went on a lot longer than our other ejaculation producing events. But I promise at next week’s first session I will have you fuck me with that big knob-headed prick of yours. But please don’t jack off too much over the weekend. I want as much of your semen as I can get.”

After my little lecture, we assumed the position on the table and I proceeded to give him a world-class blowjob. I sucked and licked every square inch of his cock and balls and even tongued his butthole. He got the full oral treatment with every trick that I had learned over the years. When his orgasm finally came, he blasted a huge load of semen down my throat, nearly choking me. I greedily sucked and sucked his exploding cock. The feel of his oversized cockhead on my tongue and in my mouth was heavenly. I couldn’t get over the fact I as being paid an obscene amount of money for something I would gladly do for free.

We cleaned up together in an adjacent shower and then got dressed. He went to his room while I went downstairs to report to his father.

“How did it go after I left? And did anything special happen before I got there”

“I started him off with a prostate massage that produced a very powerful ejaculation. The feeling of orgasm with that procedure is decidedly different from other types of orgasms. I just wanted him to be aware that there are different types of orgasms.

“Then after you left I had short lecture on various proper ways to approach women that he might desire to have sex with. Then I finished the session off with the best blowjob that I know how to give. I licked and sucked every square inch of his genital area including tonguing his anus. He had a terrific orgasm and copious ejaculation.”

“I want to thank you for including me in the dual jackoff. That was really great and I am sure the bond between me and my son is ten times more powerful than it was before. You don’t think that was too gay do you?”

“It wasn’t the slightest bit gay. One of the things that I am going to teach him is that sex between two men doesn’t have to be a gay experience. It’s just another way to expand one’s sexual experiences. At some point I will have the two of you suck each other’s cocks while I participate. Maybe you suck his while I suck yours. Or you both suck each other while I tongue somebody’s anus. We’re going to have a lot of fun and learn a lot. “

“Damn…all this sex talk, especially talk of sucking my son’s cock has given me a massive hard-on. Do you have time to suck me off?”

“I always have time for a blowjob for you,” I replied.

################

---