A Seeker's Sexual Pilgrimage Ch. 04

Someone had been training this pupil before she came under my tutelage.

"Indeed you may, you naughty little girl, when I have completed my inspection and the time is right."

You can't let the little girls set the pace. The Headmaster must remain in control. Thusly I determined that I would conduct another inspection before delivering the second strike. Usually I prefer to give them half a dozen warm up swaps to each cheek, nothing too hard, then do a quick inspection and only get down to serious business right before I stick my cock in them as I am very visually oriented, but this time I would make an exception.

"Alright, young lady," I said to Freddie, " I want you to place one hand on each buttock and spread them for me so I can have a good look at the area."

Like a belly dancer or a ballerina, with the grace of seaweed in the tides or the metamorphosing of an exploding star, she brought the extended beauty of her arms symphonically around floated her hands onto the crescents of her cheeks and separated them as the continents cleaved once upon our earth. The majesty of her fertile diamond shown forth.

I determined to examine the tangle of her pussy lips more closely. Labia can be classified much as asshole can be, but we won't do that right now.

I brought my nose close to the source of her odors. In order to smell anything, molecules of it have to touch the lining of the nasal cavity. Tiny microscopic droplets of pussy juice and anal effluvient crowded like a cloud around her open and exposed center. There was the smell of earth warming in the springtime sun, of ocean spray driving into the sky, of brown and orange. The aural sensations drove straight into the limbic system of his brain. My amygdala told me, "Fuck that hole!" I wanted desperately to comply.

Even though Freddie had a good spread going, her pussy lips clung together. I touched the center of them with my fingertip and they separated, swinging apart like vines in the jungle. The tiniest of hairs projected from the ridge of the flesh on both sides. Moisture glistened along the insides of both lips. One could almost see the curve of the liquid where the surface tension held it in place right at the middle. I inserted my finger far enough to touch it.

"Let me taste it." I turned my head to the right and there was Jeannie looking into my eyes again. "Let me taste it," she said again, so I brought the tip of my index finger up to her and let her lean forward and suck it off me. She took the whole finger into her mouth and ran her tongue around it like a cherry stem. Then her eyes directed me back towards the dewy hairs of Freddie's cunt. She really just wanted to mark her territory.

I was still wearing my pajama bottoms, but they had a big wet stain in the front of them now. Nonetheless, there was a spanking in progress and that had to be respected, so I turned my attention to her right buttock. I gave it the same respectful consideration that I had given the left side. Then I gave it a good solid smack right on the sweet spot. I cupped my hand to maximize the sonic repercussions.

Next, I began a slow steady rhythm. I favor the "circle, smack, switch, circle, smack, switch" type of routine. The "circle" portion of the proceedings can be tender and loving but ultimately it is all about the smack. The best part about a rhythm is that you can vary it. Just when the pupil thinks she knows how to anticipate the strike, you withhold it. Then you give her a double hard on the opposite cheek. You can play great head games with an ass.

Freddie was a real champ. She turned her ass to present the target each time. She didn't whimper or beg or scream or squirm, she just took a wallop and showed me the other side. It was clear that Jeannie didn't need to be holding Freddie's feet anymore, so as the sting began to build in my hand I asked Jeannie to take over for a minute while I went to get my Ping-Pong paddle.

When I came back in the room, I saw Jeannie reared back on her toes like a tennis player at full stretch getting ready to lay a righteous one on Freddie's posterior. It was a noble effort, but didn't have a chance against the largest muscle group in Freddie's Amazonian body.

With paddle in hand, I felt renewed energy and positioned Jeannie, doggie on the floor between Freddie's knees. That way I could paddle high and then paddle low. It was like a drum set. I really needed two paddles. The girls loved it.

Finally though, my arm was tired and the asses were glowing and it was time to move on. I freed my warrior and stood as naked as the girls. Twats and asses were everywhere, but I had my eye on the new one. There is nothing like a piece of strange. I pulled Jeannie out of her bottom position and stood directly behind Freddie. My cock was in my hand. Her browneye and my third eye were having a staring contest. I was ready to plunge in and suddenly, Freddie put her hand right in the way.

"Oh no no," she said. "No fucking. I'm married and I would never cheat on my husband."

"You're married!"

"Oh yes. Long time."

"And you don't think this is cheating?"

"Not as long as you don't stick it in."

"You let me look at your asshole."

"But I'm not going to let you fuck it."

"You let me taste your pussy juice."

"Well, that was kinda pushing the boundaries, but Marvin doesn't have to know, and anyway, it was just the tip of your finger."

"What about your ass? It's bright red."

"Yeah, well, that is kinda a problem. Hopefully I can hide for a couple of days til it mellows out and if he catches me I'll just say I was a bad girl and got punished but nobody fucked me."

So that's the way that episode ended. I mean, of course, Jeannie gave me her pussy and ass and Freddie stuck around and took great pictures of all the action. Having her watch and look for interesting angles was pretty exciting all by itself and when I finally came, I pulled out so Freddie could watch me spurting. Still, that's one hole I'll never get in this life and considering what a beautiful anus she had, I am saddened.

So now you are probably wondering, how did I screw this one up? Here's a lovely woman that not only let's me fuck her in the ass, she brings her friends over so she can show my cock off to them and lets me spank them and photograph me fucking her. So why am I not still with her? Well, remember I wasn't really supposed to be with her at all. I was supposed to be with Kathy.

The sad truth is that there for a while I was getting so much pussy that I decided maybe sex wasn't the most important thing in the world. Maybe, the warm and fuzzies that Kathy gave me had more value than the screeching earthquakes that I got when Jeannie was around. Stupid. That's only true for one to eight hours after the orgasm is over. From that point on, sex becomes more and more important until nothing else matters at all. Of course, if you wait a few years, the urge starts to go away and after a decade or two you can't remember what all the fuss was about in the first place.

So when it came time to decide between the two, as it inevitably did, I chose Kathy. Really, it's even dumber than that. At first, I was going to go with Jeannie. The night I told Kathy that it was over she wouldn't leave and she wouldn't stop screaming and crying and then about two AM, she hauled off and hit me right in the jaw with her best round house punch. For some reason that I will never understand, it was like the punch woke me up. "This girl really loves me" I thought to myself. Right there, I changed my mind and decided to go with Kathy.

I will never know now if it would have worked out with Jeannie, but I do know that things didn't go so great with Kathy. I am a man on the loose once again seeking smelly pussy and fucking anything that doesn't move too fast. Wish me luck.

Doctor Deucel K. La Brew Master Headmaster

*

(Author's note: These are the true confessions of Brewster926, a sexual pilgrim seeking love. If you have any advice or think you can help in any way, please get in touch. I wish you the best on your journey.)