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.

At this writing I have had three sessions with the son. This is a report on the third one, which just took place. Prior to each session I always meet with the father to go over how the prior meeting progressed and also to get his feedback on any noticeable behavioral changes that his son might be exhibiting.

“Well, Miss Kelly,” the dad began, “I can report that Jack is a totally changed boy. You have worked wonders with him. He now has an incredible level of self-confidence that he never had before. And although I find this hard to believe, inviting me to participate in your last session has worked wonders with the father/son relationship. When you put our two cocks together and jacked us both off, it created a bond between us that totally thrills me. I understand he would like to make that a regular weekly occurrence, which is fine with me. It not only strengthens the bond between us, it was one of the most fulfilling orgasms I’ve ever had. To see your hands wrapped around our two pricks pumping the cum out of both cocks was an extremely memorable experience. Actually I can’t wait until next week to repeat it.”

“I know Jack is really looking forward to it as well. And it was an extra thrill for me to have two big cocks to play with. By the way Jack suggested increasing our sessions to three times a week but I am afraid that would be too much. I don’t want to overwhelm him with sexual experiences too fast.”

“I agree. He’s already getting more sex than any other kid his age. Considering that you have in the first two meetings brought him to mind numbing, semen spurting orgasms seven times, that seems like more than enough. Handjobs, blowjobs, and full-on coitus, you have already covered most of the bases.”

“True. I know he really enjoyed fucking me and considering it was his first time, he did extremely well. He has been really bugging me about a repeat performance so I will probably fuck him again tonight. The first time, as you no doubt observed when you walked in on us, I was controlling the action with him on his back and me on top doing all the action. But tonight I will let him be on top and see how he does.”

“Sounds good. Do you have time to give me a blowjob before you start your session with my boy?”

“Not tonight. I only have a couple of minutes before our scheduled start but if you can hold off until after the session I will be happy to suck you off later.”

“OK, I can do that,” he replied.

With that, I went upstairs to the room that the father had outfitted to duplicate one of my firm’s examination rooms, except he had an oversize exam table custom built that was easily large enough to accommodate two people. Jack was waiting for me sitting on the table. He was nude and already had a throbbing hard-on. He was primed and ready to go.

“Hi Miss Kelly,” he said enthusiastically. “I have really been looking forward to tonight. I am very proud of myself. I haven’t jacked off since the last time you were here. I have been edging quite a bit (I had given him a lesson on edging) so I have a huge amount of cum stored up for you.”

“That’s wonderful,” I replied. “You know how much I love seeing your penis spurt out a big load of semen. So let’s get started. Tonight I want you to get one your hands and knees on the table with your butt facing towards me.”

He assumed the position as I had directed. I got directly behind him and reached between his legs and got a firm grip on his penis. I laid a towel on the table. I pulled his penis back towards me. It was so hard that I had difficulty pulling it back but got it aimed at the towel. I started to masturbate him while also licking his balls. As I pumped his cock I asked him if it felt good and of course he exclaimed that it did. I continued to lick and suck on his balls but then worked my way up to his anus where I gave him a rimming I am sure he will never forget. I licked, sucked and tongued his asshole while I fisted his cock making sure that my hand stroked down over the coronal ridge of his massive cockhead giving him the best sensation possible. It wasn’t long before he began to twitch and jerk his ass around, likely due to the pleasurable sensations that had to be shooting through his prick and asshole.

As I knew it would, it didn’t take long before streams of semen shot out of his cock onto the towel. Maybe it was my imagination but I swear I could feel the cum shooting up through the shaft of his penis where I had a tight grip on it. I continued to tongue his butthole the whole time that the cum spurted from his engorged cock.

“Omigod Miss Kelly,” he blurted out, “that was amazing. What an incredible feeling. I’ve masturbated hundreds, maybe thousands of times, and none of my orgasms ever came close to matching that. You are wonderful.”

I had Jack turn over and lay down after I snatched the cum soaked towel off the table and threw it in a waste can. I often wondered what the maid thought of all the cum saturated towels that we left behind after each one of our sessions.

After Jack laid back, somewhat exhausted, I took hold of his still half hard penis and lightly sucked that big knob end. I loved the feel of his silky cockhead in my mouth. As my sucking got a bit more active I could feel his penis stiffening in my mouth. I decided to see how quickly I could bring him to orgasm again. I usually gave him some rest time between orgasms but I knew teen boys had amazing recuperative powers. I remember one very young patient that I had where I had sucked him to three consecutive orgasms without ever taking his penis out of my mouth. So I was pretty sure I could get Jack to spurt a second load of cum, this time down my throat. And I wasn’t disappointed. It took a bit longer than I had expected but when it came, it was an extremely large load considering I had just jacked him off. There was so much cum that I had a bit of trouble swallowing it fast enough to keep it from spurting out of my mouth. I had a firm grip on his nuts the whole time I sucked him, just releasing them when his orgasm started to avoid doing anything that would pinch off the streams of semen that flowed out of his prick.

“I can’t believe it Miss Kelly, but it seems like each orgasm is better than the last one. I’m not complaining but why did you bring me off two times right in a row without a rest period?”

“Because after you recover, you’re going to fuck me and I wanted to have as much available time as possible for that. We are going to try as many different positions as possible. Either until we run out of time or you shoot your cum into my pussy. If you noticed I had your dad move a standard sized bed into this room. I think a bed is a much better place for what I have planned than this exam table.”

“That really sounds wonderful Miss Kelly. I really loved fucking you the last time although it would be more accurate to say you fucked me. But feeling my penis inside your vagina was unbelievable.”

“OK, I want you to just lay there and relax for 15 minutes. Then I am going to give that wonderful penis of yours a workout you will never forget.”

“OK, no problem. Can I ask you a question?”

“Sure, what is it?”

“I don’t know quite how to say this but one of the things I’ve seen on the internet is where guys put their penis in a girl’s ass. Will we be doing that?”

“I kind of doubt it. You have an extremely thick penis, especially the head. I am afraid it would hurt too much. I’ve actually never done anal sex just for that reason. If you had a little boy dick I might be tempted to try it but your big cock scares me. I hope you don’t mind. We have plenty of other things we can do to make up for it.”

“I understand and that’s ok. I just thought I would ask.”

After his 15-minute rest period we moved over to the bed. He had lost most of his hard-on so I jacked and sucked his cock for a few minutes until he resumed his full erection state.

“Here’s what I want you to do. We are going to take this slow and steady and try a number of different positions. We will start with what’s called the missionary position. Me on my back and you between my legs. But first I want you to rub the tip of your cock up and down my slit.” I laid back on the bed and spread my legs. I could feel my lips part slightly. “Do you see that little button that’s at the top of my vagina? That’s my clitoris. Some people call it the love button. That’s where almost all my sensitivity is. The actual inside of the vagina does not have that many nerve endings so most women cannot reach orgasm from just having a cock thrust back and forth in their vagina. However I am much more orgasmic than most women so I usually have no trouble cumming even without direct stimulation to my clit. But I want you to rub the head of your cock on my vaginal lips and also my clit.”

Jack proceeded to do as instructed. It felt heavenly to me. I felt myself starting to get wet which is why I wanted him to rub my pussy with his cock. I reached down and massaged my clit and almost immediately had an orgasm. I wasn’t kidding when I had told him how orgasmic I am. I can literally cum after just a few seconds of stimulation on my clit. If I keep rubbing it I can cum over and over and finally it gets to be too much and I have to stop.

After feeling myself getting wetter and wetter, I reached down and took hold of Jack’s cock. “Let me guide you in, Jack,” I whispered. I nosed the head of his prick around my opening letting it push aside the outer lips of my pussy. When I had his large knob comfortably resting between my now sopping wet pussy lips, I told him to shove it in, but not too hard. Which he attempted to do. But as before, when we initially fucked, the head was so large that it didn’t want to easily slide into my pussy. I told him to keep pushing but not too hard. Finally after several thrusts, I felt the cockhead push past whatever was holding it back and slide right onto my vaginal canal. When he was about three quarters of the way in, he bumped up against my cervix. Unfortunately that was as far as it was going to go. Despite the widespread belief that the penis can penetrate the cervix, that’s a myth. I told him to start fucking me but to be careful about hitting bottom too hard. I told him every time he hit bottom it hurt a little but if he hit it too hard, it would hurt a lot and that would lessen my pleasure substantially. A little pain actually felt good for some reason.

We fucked in that position for maybe fifteen minutes but I was afraid he might cum. So then I turned over and had him enter my pussy from behind. By now I was well lubricated and his cock slid right in. He said the feeling of my pussy on his cock actually felt better in the doggy-style position but he missed seeing my face. He said we couldn’t do it doggy-style for very long or he was definitely going to spurt his semen. He said that position somehow put additional pressure on his cock that made him want to cum. I had heard this many times before from other men so I knew he was right.

I took him through about four or five other popular positions. I guess there are a great many different ways to fuck but I felt it was best to just stick with the more common ones. After we had tried a number of different ones, I knew he was definitely ready to cum. We had been fucking for about 45 minutes with frequent stops to allow his cum urge to abate. I asked him if he had a favorite position he would like to use to finish off. He said that he would like to do it doggy-style because that really felt the best on his cock of any position we had tried. He also said that he would really like to be facing me when he came but we would probably have many other opportunities to do that.

So I rolled over on my stomach. I actually put a pillow under my belly that arched my ass up in the air and gave him better access to my pussy. He slid his cock into me with no problem and started really pounding the hell out of my pussy. I know he was trying to avoid slamming my cervix and most of the time he was successful but a few of his thrusts really hurt when he went too deep. I didn’t say anything because I knew he couldn’t last long and there were really only about a total of ten or twelve thrusts before I felt a massive flood of semen spurting into my cunt. He was definitely ready. He kept pumping away as spurt after spurt of his creamy semen buried itself deep in my vagina. I was on birth control pills so I wasn’t worried about getting pregnant.

Finally he was fully spent and collapsed onto my back. He was breathing heavily and was groaning and moaning in ecstasy.

“Oh Miss Kelly,” he gasped. “That was the best orgasm I’ve had of all of them. It was wonderful.”

“It was glorious,” I breathed, “I think I came at least five or six times. If felt so good I lost count.”

After about ten minutes of just lying together, he rolled off of me as his cock slipped out of my pussy. I turned just in time to see it slap back on his belly still somewhat engorged. I rolled over next to him and took his penis in my mouth and sucked all our combined juices off of it. Even after lapping it completely clean I continued to lightly and playfully suck the large knob on the end. I couldn’t get enough of his really large cockhead. Finally we were out of time and had to get up and take a quick shower together. We played with each other’s genitals in the shower. He wanted to go again but I was adamant that we had to closely maintain our time schedule. I know he was disappointed but there had to be some limits.

After we dressed he retired to his room and I met with his dad. I had promised the dad a blowjob and I planned to make good on that promise. Also he had said he would pay me after each three sessions so I had some money coming.

I told Robert that the session had gone extremely well and per our plan, I had brought his son to orgasm three times. I said that his boy acquitted himself quit well when I let him fuck me and that Jack had said that was the best orgasm he’d ever had.

“Miss Kelly, here’s a check for your services plus I put a little bonus in there because I am so thrilled with the results you are achieving with my boy.” I peeked at the amount of the check and was shocked to see it was for $12,000. Our deal was for $1,000 an hour and I had been with his boy for six hours so the bonus was an extra $6,000. But I had also given him a few blowjobs as well so I guess I earned it.

I slipped the envelope in my purse and thanked him profusely.

“OK, Robert, get that cock out so I can suck you off like I promised.” He was wearing sweats and I could see he was already hard from the prominent bulge showing. He quickly stripped the sweats down and wasn’t wearing any underwear. He lay back on the couch and I proceeded to suck his cock until he exploded in my mouth.

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