The Headmaster Ch. 01

This is the first is a series that I am working on. Hope you like them.

Chapter 1. The Opportunity and First Times.

My wife and I decided to get out of the fast lane of the high tech world. We had an opportunity to take jobs that were offered to us by a friend who knew we were a little burned out. He was on the board of a private school that dealt with children or young adults who were trying to get their lives together. It was for those who had made the tough decision to try to get a high school diploma after run-ins with the law. It was a kind of boarding school for miscreants. Since we both had advanced degrees and plenty of experience, he got us a chance to interview for the positions and we were accepted.

We would be taking over as the "Headmaster" and "Dean" of the school. I would be the headmaster based on my experience as a leader and manager. My wife, who has the English degree and writing experience, would be the dean.

After we moved into the house reserved for the headmaster of the school, which was directly adjacent to the school property, we settled in to what appeared to be a normal academic situation, albeit with youngsters who had had problems and were trying to do the right thing. Most were between the ages of 17 and 22.

When we moved into the offices, we found that our two offices were adjacent with a connecting door and we each had an administrative assistant outside on opposite sides of the two offices. The planning had not been perfect for this converted old public school, because our offices shared a common wall with the men's and women's bathrooms. If there was ever a backup in the sewage, it was going to be monstrous in the offices, but so far so good.

My wife and I have always had an excellent physical relationship, and we had discussed several times moving to another level sexually, but stress, jobs, and everything else in life interfered. This would turn out to be our first opportunity.

The layout of the offices was rectangular with a storage closet in my left corner and my wife's right hand corner. They were next to each other with the wall of our offices between them. They were recessed right next to where the men's and women's bathroom stalls were. One day, while in my closet getting something, I neglected to turn the light on and was retrieving something quickly, when I saw light coming from behind a stack of boxes that was nothing but a bunch of old files. I moved the boxes and noticed that there was a small handle there. When I pulled the handle, it pulled back on hinges a small piece of plywood that was hiding a small hole. I bent down and checked it out. I had a bird's eye view just behind the last women's room stall, the handicapped stall, at the toilet. The hole was very small. It was barely large enough to get a good view, but as I stood there wondering who made the hole, the stall door opened and a young woman entered. I was transfixed by being able to peek in on her. I quickly closed my closet door so that there was no chance for any light from my office to give me away. I sat down on a box quietly and watched her go to the bathroom. I decided to approach my wife with a plan to expand our horizons.

After the young woman finished and left, I studied the layout. The storerooms shared a wall that turned out to be just a couple of sheets of plywood that must have been thrown up quickly, because it could quickly be taken out. I went through the adjoining door into my wife's office and checked out her closet. There wasn't a pre-made hole in there, but I figured it would be easy to make one.

I formulated my plan the rest of the afternoon and discussed it with my wife that night. We would make a hole for her to watch and "play" with the boys and for me to watch and "play" with the girls and then come up with a way to circulate a rumor about a "glory hole" type of operation. We had visited some of the sites on line and discussed it, but never got around to trying it. I was dying to have my dick sucked through one by a stranger and have my wife do the same to another man. In this case, it would be much more of a thrill because of the situation. We would start the rumor and see if some of the older students would attempt it. Of course, in our busy schedule, it might be a little difficult, but we could definitely work on it at lunch.

We made the hole on my side a little larger, at least for my dick. It's not long, only about 6-7 inches, but has good girth. On my wife's side we made it large enough to allow some well endowed men. Finally, we made some cuts into my closet so that I could put a special one-way mirror in there and watch the young ladies as they sucked my cock. My wife decided that it was best for her to do it anonymously and that was what excited her.

With this plan made, we then had to make sure the rumor got started. It only took a couple of questions like we were asking some of the older students about this rumor, before it was rampant. Now we waited.

One Friday during lunch time, we took our lunches into the closet and sat quietly, hoping for something to happen. It did when we heard a young lady enter the stall next to my office. I immediately checked her out (nothing too young would be acceptable), and it was perfect. She was one of the nineteen year old "tough" girls. She was a little goth-like with a couple of tattoos, dark hair, a lithe body (probably about 5'5" and 110 pounds), and great sucking lips. I watched her take down her pants and panties and sit on the toilet, and my wife started undoing my pants. I let her pull them down and stroke my dick a couple of times. I was hard instantly.

My wife whispered into my ear. "Any time now."

Then, I did it. I stuck my dick into the hole and watched her reaction. She gasped, then immediately recovered and acted very nonchalant as she reached over and ran her fingers over it. It felt heavenly. Suddenly, my wife came up next to me to watch, too. As the woman started stroking me, my wife ran her hands lightly over my ass, tickled my balls and kissed me very hard. I looked back down just in time to see the young woman turn and bend forward. Oh my god! She was going to suck me! My fantasy was about to come true! She licked it very lightly all around the head and then very carefully wrapped her lips around it and started a light sucking. She still had her panties down and started stroking her pussy. She leaned back and looked at my dick and her saliva that had made it so wet and slick. She seemed to be studying it; the veins, the way it was throbbing, and its general size. She very slowly leaned forward and took as much as she could into her mouth. She wrapped those wonderful lips around my cock and swirled her tongue across the bottom of the head and moved her head back and forth slowly as I stood there transfixed. My wife continued to watch her and was stroking my balls.

She leaned up and whispered into my ear. "Is she any good?"

All I could do was nod my head. I was in heaven. My cock was as hard as it had been in quite a while and was starting to throb heavily. I'm sure she could tell that my dick wasn't going to last too long. Suddenly, the young woman increased her sucking and tugging with one hand on my cock while she stroked her clit and pussy. I was going to blow my load really early, I could tell. I started moaning and that automatic thrusting instinct started happening. That made the young woman start sucking hard and I could tell she knew by my actions that I was going to cum. I started fucking her mouth strongly and finally came in several large spurts. She just kept sucking and swallowing, sucking and swallowing. When I stopped thrusting, she carefully backed off it and looked at my dick. She then took it in her mouth again to clean it off. My dick twitched and she giggled.

I slowly pulled back and she sat back, opened her legs wide and started furiously rubbing her pussy. She was completely shaved and was rubbing her clit as fast as she could. She was desperate for release and my wife and I watched as she got off, cumming loudly and moaning so much that anyone in the bathroom would have known that she was masturbating. When she finished she stood up, straightened herself and left. I turned to my wife and she had her pants down around her knees masturbating, too. I dropped to my knees and started licking and sucking her clit and pussy. I put two fingers in and sucked on her clit and she grabbed my head with both hands and started moaning and groaning. It was probably too loud, but she was past caring. She held on to my head as I ran the rough part of my tongue over her clit again and again, and now with three fingers going in and out of her pussy as fast as I could. Suddenly she stiffened and held my head like a vise as she cried out that she was cumming. I didn't let up until she started to collapse to the floor.

Finally, with both of us sitting on the floor completely spent, we knew that this was going to be amazing. We also knew of some other things that might make it even more interesting.

It was a few days later before something happened again, and this time it was in the men's room. We didn't know if anyone had tried to use the bathrooms when we were busy, but we figured they would not expect for there to be someone in the other bathroom all the time. We just hoped that a couple didn't try to arrange to do this to each other and then find that they couldn't get together.

It was lunchtime the following Wednesday when one of the young men entered the last men's room stall, saw the hole, and decided to check it out. We had draped a black cloth over the men's hole so that they couldn't see anything in the storeroom, although the light level was pretty low as well. We could tell that he tried to look into it by pushing on the cloth, but obviously couldn't see anything. He either recognized the idea of a "glory hole" or just took a chance. In any case, suddenly a decent sized dick came through the hole. My wife looked at me, questioningly I thought in the dark, so I pushed her on the back of the head towards the dick. She turned and put her hands on it and starting stroking it. It was hard and throbbing immediately. Ah, youth! She stroked it a few times and the pre-cum started leaking lightly. She leaned forward and licked. We could hear a moan from the other side of the wall. Then she just engulfed it totally and must have been swirling her tongue, because we heard very clearly his gasp.

"Oh, my god, don't stop." We heard him say.

She wasn't about to, but was very turned on herself so she got up from her knees, bent over from the waist, lifted the skirt she was wearing that day, and pointed at her ass. I knew what she wanted. While she was giving head, she wanted me to do her. As much as I wanted to watch her, I could hear and feel the actions from her body, so I got on my knees and ran my tongue from her clit to her asshole. She jerked slightly from the contact. She always tasted delicious and had a very sensitive clit. I could feel her working on the hard cock. She was slurping and licking and the sound was turning me on so much! I started tongue fucking her asshole and stuck a couple of fingers in her cunt. Her inner lips opened up and she was getting so wet that she was about to start dripping. I kept slowly swirling my tongue around her ass, which she loved and then would alternate with a quick poke into it. This combined with my finger-fucking was making her get closer and closer to cumming. I could hear her sucking and his moaning and she suddenly took her mouth off the young cock

"Fuck my ass!" She whispered harshly.

She had never wanted anal sex. My dick was so hard I was having a difficult time getting my pants and underwear down. Suddenly, I heard the young man's groans increase and I had to shuffle forward to see her mouth. I wanted to see her take the cum. She kept sucking and saw me shuffle around to her side with my pants around my ankles. She looked up and I could just make out her actions in the dark. She worked hard on the cock, sliding it in and out and jerking on it in time with her sucking.

Suddenly he exclaimed "I'm cumming!"

My wife's eyes went wide as the first squirt hit the back of her throat. She kept sucking and swallowed his entire load. She held on to his dick after the last couple of squirts and licked it lightly and he moaned from the sensitivity of the underside of the head. She smiled at me, he pulled his dick back and muttered a thank you through the wall, and I shuffled back behind my wife with a boner that felt as big as a large cucumber. I slowly entered her pussy and it was so wet and tight. She moaned at the same time I did. She was so turned on, and I wanted that ass badly. I slowly stroked in and out and started wetting my finger in all the pussy juices that she was leaking out. I put my soaking wet finger into her ass to prepare her for my dick. After a few strokes, I knew I was ready for her ass and I pulled out of her pussy and put it to the entrance to her ass. She moaned and reached back to pull her ass cheeks apart. I pushed forward to try to enter her virgin ass. In all our years together, she had never wanted anal sex, but this was obviously a new chapter in our relationship. I kept pushing and she took her hands off her ass to put them on the wall in front of her to steady herself for the pushing. The sphincter muscle finally gave enough for my head to pop-in and she exhaled audibly to let me know that she could tell the head was in. I kept slowly pushing until about 5 inches was in and she reached back and stopped my progress.

"I feel completely full at this point." she said.

I knew that she had enough, so I started pulling it back out until the edge of the mushroom head was touching the rim. She reached up and starting fingering her clit and was beginning to shudder. I knew that that meant that she was ready to cum. Of course, being in her virgin ass, with its newness mentally and tightness physically, meant that I could come in about three strokes, so I eased it back in and she starting rubbing her clit really hard and had a major orgasm. It was so strong that she almost couldn't stay standing and her knees tried to buckle. I helped her stay up by holding her hips and knew I should cum immediately. I then used about two quick strokes and my cock spasmed over and over and the sensation was amazing. It kept jerking and jerking and I could barely stand up myself. We collapsed onto the floor and my dick made a wet squishy sound as it popped out of her ass.

We lay there together on the floor and she whispered "That was the largest orgasm I've had in years."

"Me, too." I confided.

We were close enough to see each other now and she asked "Did you enjoy seeing your slutty wife suck the dick of a young stranger?"

"It was better than I ever imagined. What about you getting fucked in the ass by your husband with his cum still in your mouth?"

"I want to do that again, but my ass is going to be sore for a day or two. Maybe next time we can try something a little different."

I looked at her puzzlingly and was silent. I didn't know what she meant.

"It'll be a surprise and I know that you will love it. Just let me handle everything."

I couldn't wait. See what's next in Chapter 2.