The Headmaster, Chapters 1 To 11 free porn video

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, 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 for me, too, in case there were 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. 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. 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 starting 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 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. Hear about that in Chapter 2.

Chapter 2. My wife gets her chance.

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 some in the other bathroom. 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 lightly. 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 and the words “Oh, my god, don’t stop”. 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 and manage to whisper, “Fuck my ass!” 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. Then he exclaimed “I’m cumming”, and 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 come 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 3.

Chapter 3. My wife gives me a surprise.

The next day was Thursday and we wondered if anything else would happen. I heard someone come into the women’s room and I checked it out. It was a gorgeous 18 year old name Christy who I knew a little, and the same 19 year old named Veronica who sucked my dick the previous week.

Christy was a little busty, probably only a C cup, but plenty busty for such a young thing. She had strawberry blonde hair, a small waist, and those great womanly hips that were so good to dig your fingers into when you were fucking doggy style. She was probably only 5’3”, but was a little healthy girl at about 130 pounds.

Veronica was saying to Christy, “Just check it out. When I was in here last week some guy stuck his dick through the hole and I sucked it off. I think the men’s room is on the other side. It was different and I liked it.”

“No way”, said Christy

“Oh, yes”, said Veronica. “It was a decent size one and if you get lucky, one of the boys with a decent dick will give you a chance, too.”

“That would be cool!” said Christy. “I haven’t fucked in about 6 months and I want to feel a cock again. I love sex and this anonymous stuff kind of turns me on!”

My wife and I listened to them, and my dick was getting hard from being able to listen to them talking about sucking and fucking.

My wife knew it and got behind me. She unbuckled my pants, dropped them around my ankles and started to stroke my dick. She was always good at that!

Then Veronica started gently rapping on the wall.

“What are you doing?” asked Christy.

“Just letting anyone who is over there know that there’s someone here ready to suck cock.’ She responded.

“Keep it down!” Christy answered. “We don’t want anyone else to hear us.”

My wife then opened the hole and guided my cock toward it. I stuck it through.

“Whoa!” said Christy. “That’s a decent one. Looks like just the right size for me.”

Veronica stepped forward and wrapped her fingers around it. It was heavenly every time one of these young girls grabbed it through the hole.

“Hold on there, Veronica”, Christy whispered. “This one’s mine.”

“Then take care of it, slave girl”, Veronica said mockingly.

At that Veronica smiled and stepped back. Christy swooped in on my dick. It was throbbing and starting to leak pre-cum. Christy stroked it a couple of times and then got down on her knees. It was the moment I was waiting for. Veronica came forward and leaned against the wall so she could watch. I didn’t know she was going to watch and enjoy her friend suck a strange dick, but she seemed very interested. Christy licked the head lightly and held it in her right hand. She smoothed the pre-cum over the head with her thumb as she stared straight at the one-eyed monster staring back. She then leaned forward and starting sucking on just the head. I could feel her moving her tongue against the underside. Wow! Either these teenagers were pretty damn good at sucking dick, or I was just so turned on at having these youngsters doing it that I just thought it was good, but either way, I was really turned on. My wife was up at the mirror watching the girl suck it. She was again playing with my balls. I starting playing with her ass through her skirt, but she pushed it away.

“This is for you”, she said.

I looked back down at Christy, and she was sucking pretty well on about the first 4 inches and using her right hand to jack it up and down as she pulled back from it with her mouth.

“Mmmmm”, Christy moaned. She then took it out of her mouth, looked up at Veronica, and said, “I’ve got to have this in my pussy.”

“Go for it”, Veronica said. “But I still want to watch”, she said while licking her lips.

“Good thing this is the handicapped stall”, commented Christy.

Christy stood up and raised the cute little skirt she was wearing. She had on a black thong, the standard wear of all the teenagers it seemed. She lowered the thong and rubbed her hand through her gash. It was definitely wet. She brought her hand up towards her mouth, but Veronica stopped her by grabbing her wrist and directing Christy’s fingers to her own mouth. Christy hesitated, holding her hand back, but then relaxed and let Veronica suck her cunt juices off her fingers.

“I have got to get that cock in my cunt”, Christy said rudely as she backed up to my dick.

I felt her rub my dickhead up and down her pussy, lubricating it and readying it to enter her pussy, which felt very wet and extremely hot. I wanted so bad to be able to reach through the wall and grab those wonderful hips. Her ass was so smooth, round, and beautiful, that I wanted to smoother it with kisses and fondle it, and then fuck the shit out of her.

I turned to my wife and whispered, “This girl is just downright gorgeous”.

“I think so, too” she whispered.

She looked down and we both watched her slide my cock into her cunt. It was very tight. She made it sound like she had had plenty of sex, but at her size and being so young her pussy was extremely tight. But it was so wet that my dick still went in as far as it could as her ass backed all the way up to the wall. Veronica giggled and said, “That is so hot!”

Christy responded, “Everything is hot… my pussy is very hot and wet and this dick feels like it’s on fire.”

She kept her ass still for a couple of moments so I automatically started fucking her.

“Oh, wow!” she muttered.

“What?” asked Veronica.

“He’s f-fucking me”, she stuttered while enjoying the moment.

Suddenly, my wife moved behind me and left the closet. I was momentarily startled, but my dick had a mind of its own and didn’t miss a beat (or throb). Where was she going?

I was fucking her slowly, but knew that I was going to cum soon… and then she started moaning, “I’m going to cum”.

I could feel her increase her rubbing of her clit and I started fucking her faster. She rubbed and rubbed and moaned and then starting quivering, saying “Here it comes!”

Little did she know that that was exactly the right thing to say. I could feel her pussy muscles contracting and I knew I was gonna blow. I shoved it into her and kept it buried as she came and I spurted once, twice, three times and then it just kept throbbing. Christy moved forward and let it slip slowly from her cunt. I left my cock there and I could look down and see all our mixed juices on it. While Christy sat down and rested with her legs wide open, Veronica got down and started cleaning up my dick. It was wonderful. If I wasn’t on the other side of 40, I probably couldn’t have gotten it right back up.

Suddenly, the door to the stall flew open, almost hitting both of the girls, and my wife was standing there looking very angry.

“Just what the hell do you girls think you are doing? And whose dick is that?”

That was my cue, I figured, so I pulled it back and closed the hole cover.

“We’ll deal with that later.” My wife continued. “Veronica, get off your knees. Christy, you look like a terrible fucking whore. You are lying there with your legs wide apart and what looks like that dick’s cum all over your pussy and legs. That is disgusting! Now get up and report to the headmaster’s office immediately”, and she closed the door and stormed out.

“Oh, fuck!” Christy said.

“Sorry, Christy.” Veronica said. “I hope it’s not too bad. I’m sure she’s going to come back and get me soon. Let me know what happens later. You’d better get moving”, and she rushed out of the bathroom.

I was paying so much attention, that I forgot that I had to get my pants back up and get into my office. The young woman I just fucked was coming to my office with my spunk still in her pussy! YES!

I had just sat down at my desk when there was a knock. I told them to enter and my wife came in dragging Christy by the arm. She looked more than alarmed, she looked cowed and scared out of her wits. She was trying to put up a front, but her eyes were giving this away. I knew from her background that she was going to jail if this didn’t pan out.

“What’s going on here?” I asked, acting surprised at what was before me.

“I caught this slut fucking in the bathroom!” my wife said loudly and rudely. I could see that Christy was shocked at my wife’s language in front of me. But she continued “I caught her just as she finished and she has a pussy full of cum!”

I loved the dirty language and was getting a little turned on again. “Who was the guy?” I asked, pretending not to know about the glory hole setup.

“That’s the worst part,” my wife said, “She was fucking him through a hole in the wall and the dick disappeared before I could grab it and determine who it was.”

By now, Christy was standing in front of the desk, her head bowed, almost in tears at the thought of going to jail. But my wife had other ideas. I just didn’t know what they were yet.

“Well, Christy, what are we going to do with you?” my wife asked as she lifted Christy’s chin and made her look up. “I think the first thing you need is the headmaster’s paddle.”

Christy looked up suddenly and started to say something and my wife slapped her. The smack was flat-handed but pretty strong and loud. Christy was flabbergasted and stood there in stunned silence. Then my wife led Christy to my desk.

“Put your hands on the desk and bend over. Prepare to get paddled.” My wife said. Christy obeyed, but with small whimpers.

I got up and got the paddle from where it hung just inside the door. It wasn’t used much and hadn’t been used at all by us in the short time we had been there, but it was a big flat wooden paddle and would definitely hurt. I handed it to my wife and she motioned me to sit down in one of the visitors chairs in front of the desk. I sat down to watch the show.

My wife turned back to Christy and said “Ready?” Christy didn’t answer, but just nodded her head. My wife landed the first smack with a loud thwack and Christy flinched and whimpered some more. My wife waited for a minute and then ordered her “Raise your skirt up so that I can get a proper paddling in. Pull it up over that slutty ass!” Christy hesitated and took a peek back at me. My wife pointed and said “Now! I didn’t tell you to look around you slutty little whore!” Christy obeyed.

Now I was looking at that beautiful ass in person, covered only by a little thong material. My wife smacked it again and Christy audibly exhaled and let out a long “Oooohhhh”. It obviously hurt. My wife stopped and looked again and said to Christy, “Oh, my God! Your little whore cunt is leaking that man’s cum and your juices all down your legs! It’s disgusting! What are we going to do about that? HUH!?!” and she prodded Christy’s ass with the paddle.

“I-I d-d-don’t know” she stammered very quietly, afraid to speak up.

“I do” said my wife. “Take off that thong and wipe it up off your legs. NOW!”

Christy looked up. She had gone completely pale, but my wife glared at her and pointed the paddle at her. Christy slowly lowered the thong, bringing that gorgeous pussy into view as she bent over to get them over her shoes, and then wiped her legs. But my wife wasn’t finished. She reached out and grabbed the thong and tossed it to me, turning to me and winking so that Christy could not see it. Christy had resumed her position, so my wife smacked her again. Now you could see more cum and juice dripping from her pussy, so my wife decided to take matters into her own hands, literally.

My wife reached over between Christy’s legs and said “Look at all this cum you scumbag whore!” and she ran her hand through Christy’s gash and gathered a good amount of goo. Christy shivered at the contact and tried not to move. My wife said to her, “Turn around and face us”. Christy obeyed. “Keep that skirt up, slut!” she told the young girl. Christy obeyed again. And then my wife said “Look at this goo from your gash. It’s disgusting that you have it dripping down your leg and might get it on the headmaster’s carpet. Here, clean this disgusting stuff off my hand before I get sick”. Christy looked completely obedient now and just did it without any reaction. She let my wife put her fingers into her mouth and licked them clean. I was getting a major hard-on.

My wife then stepped directly in front of Christy. She glared and Christy averted her eyes. Christy was still standing there with her skirt around her waist, holding it and I could see that she shaved her pussy, leaving only a little triangle above it. It meant that the lips were clearly on display. While I was checking all this out, my wife moved to the next part of her plan. She slowly slid her hand down the front of Christy’s bare pussy and stuck two fingers in. She pulled up like she was grabbing onto something heavy. She looked Christy directly in the eyes as Christy’s eyes fluttered and focused on my wife, and said “This is now my pussy. I will tell you when and where you can let it be fucked and who can cum in it. I will use it as I see fit. If you don’t agree, then we can call your parole officer right now and send you back to jail. Do you understand your Mistress, my little obedient slut?”

Christy looked a little confused at first and then her shoulders sagged and she acquiesced. “Yes, Mistress. I will do whatever you order.”

I was amazed and shocked and so fucking hard I could almost come just sitting there without touching my dick!

“OK, Christy,” my wife continued. “First, I want you to go clean yourself up, get to class, and come back to the headmaster’s office after your last class. At that time we will discuss the next step in your punishment and how you will serve me. Understood?”

All Christy could do was say “Yes, Mistress” again.

My wife pointed to me and said “And that’s your Master. We will be Mistress and Master whenever the three of us are alone. Got it?”

“Yes, Mistress” she said one last time.

“Now go get cleaned up and get to class” my wife ordered, as she waved Christy for the door.

Christy finally lowered her skirt and smoothed it out as she headed for the door. She was gone quickly and my wife turned to me with a big grin on her face.

“Well, what do you think? Is this something you are interested in?” my wife asked me.

I stood up, dropped my pants and grabbed my engorged dick. I had Christy’s thong in my hand and wrapped it around my dick. “Does this answer your question?”

“Obviously”, she responded. She came over and wrapped her hand around it, but didn’t start moving at all. She looked at me, smiled, and said “But I think we should let it rest until this afternoon when you get to fuck that gorgeous creature, don’t you?”

My dick throbbed at the thought and she said “Yep, I can tell that your dick approves. I’ll get back to my office and come up with my plan for later”.

She left to go to her office and I tried to get my pants back up and sit down behind my desk. I wanted to get my emotions under control before I starting whacking off right there on the spot. I was extremely turned on but I managed to get under control so that I could save myself for later.

“Wow!” I thought. This was going to be amazing.

To find out go to Chapter 4.

Chapter 4. Christy’s Punishment.

I was trying to get some paperwork done, but couldn’t concentrate very well. I kept thinking about what my wife had done to Christy and how that beautiful young thing was going to be coming back at about 3pm.

I checked my wife’s office at about 2:30 and she wasn’t there. I walked all the way through to the other side and asked her assistant about it and she said that my wife had run out on some errands and would be back by 3. I went back to my office and told my assistant that she could leave early today if she had no pressing paperwork to get done, and she said she would leave as soon as she finished some report she was working on for me. I was afraid it might get too loud in my office after 3pm.

Finally, around 3pm, my wife strolled in with a shopping bag and sat down in one of the visitor’s chairs. I asked where she had been and she put her finger to her lips and shushed me. She grinned like a Cheshire cat and finally said “Anticipation baby, just enjoy the anticipation.”

It was well after 3pm, in fact closer to 3:30 when there was a knock on my door. I knew that my assistant was gone, so my dick jumped a little in anticipation of it being Christy.

My wife went to the door, opened it, ushered Christy into the room, and told her to stand before my desk. Christy was dressed in the same outfit from earlier; a white button down shirt and a mid-thigh skirt. My wife told Christy to face me to tell me what exactly had happened in the bathroom. Christy hesitated and then began telling the story.

“Veronica said she had a surprise for me, so we went in to the lady’s room and she led me to the last stall and told me to go in there for the surprise. We went in, and then she told me that some guy had stuck his “thing” through a hole in the wall and she sucked him off. I didn’t believe her at first, but then a dick came through the wall. I was excited and put it in me until he came. Then I had just sat down when Mrs… I mean Mistress came in.”

We both knew that that was an abbreviated version of the story. My wife got up and stood directly behind Christy.

“Are you afraid of the more common terms for the human body, Christy?” my wife asked. “You said he put his “thing” through the hole. It was a big dick, right?”

“Yes”, said Christy tentatively.

“Yes, what?!?” my wife demanded.

“Yes, mistress, it was a big dick.”

“And where did you put this big dick, Christy?”

“I put the big dick into my vagina, Mistress.” She responded.

My wife wouldn’t let it go at that, though. “That’s all? Just into your vagina?” my wife continued.

“I think I might have sucked on it when it first came through.”

“You mean “Yes, I sucked on that big dick, Mistress” don’t you, Christy?” and with that my wife grabbed her face with her right hand and squeezed her cheeks.

“Yes, Mistress, I sucked on the big dick” Christy said weakly. She appeared to be putty in my wife’s hand. Meanwhile, my hard on was becoming uncomfortable.

“And then you let that big dick fuck you, right?” my wife continued.

“Yes, Mistress, I let that big dick fuck me.”

“Did you like it?” my wife asked.

Christy hesitated, but then it seemed that she figured the truth was best. “Yes, Mistress, I liked it.”

“I could see that by your pussy juices running down your leg.” My wife said. “I think it’s time for some more punishment. What do you think, Christy? Are you ready for some more paddling?”

Christy hung her head and muttered faintly, “Yes, Mistress”.

“Assume the position” my wife said.

Christy bent forward and placed her hands on the desk. My wife lifted Christy’s skirt up over her ass onto her back. Christy had put another thong on after cleaning up all the cum juices. This one was pink.

“Master,” my wife said to me, “Please retrieve the paddle for me.”

I looked at her questioningly. I had a boner the size of Wisconsin in my pants and getting up with Christy leaning onto my desk meant that she wouldn’t be able to miss it. My wife nodded and winked at me, leading me to believe that this was part of the plan. So I stood up and my hard on was unmistakable. Christy saw it immediately and kept her eyes on it the best that she could without moving her head as I moved to get the paddle. I retrieved it and handed it to my wife.

My wife looked at Christy’s ass and ran her hand gently over it. Christy squirmed just a little.

“It is a very nice ass, isn’t it Master?” my wife asked me and she motioned me over.

“Yes, I would say that that is a very fine young 18 year old ass.” And I ran my hand over the cheeks. “Oh yes, it’s very firm and in good shape”.

“Well, let’s hope it’s ready for this.” And my wife smacked her with the paddle. Christy jumped at the first contact.

My wife acted like she just noticed my predicament as I stood on the other side of Christy.

“Oh, my god. Christy, stand up and turn around, but remember to keep your skirt up to your waist.” My wife said. Christy did as she was told. “All your terrible, dirty talk about sucking and fucking a big dick has gotten my husband’s dick hard. Now you’ve made him terribly uncomfortable and even at his age, he’s going to need to relieve it soon or he’ll get blue balls. I don’t want to have to satisfy him every time one of you sluts decides to display yourself or talk dirty around him. Do you think that’s fair to me, Christy?”

“No, Mistress.” She answered. Her eyes were locked onto my dick, but she seemed unaware of where this was going.

“Well, what are you going to do about it?” she asked Christy sharply.

Christy started to open her mouth, but was unable to come up with anything that might please her Mistress and looked questioningly at my wife.

“You are a brainless slut, aren’t you, Christy. I want you to get down on your knees, take out my husband’s dick and relieve him of that pressure, understand?”

Christy looked quickly up to my wife and started to say something, but was greeted with a slap across the face. She didn’t get to object. She stood there in shock for a second, but then let go of her skirt, slowly lowered herself to her knees and started undoing my pants. I, on the other hand, was ready to explode at this idea of my wife ordering this young woman to blow me and watching it.

Finally, she had my pants pulled down and my boxers, too, and my dick was there standing up waving in the open air. I looked down at Christy, who was wrapping her hand around my dick and smearing the pre-cum across the head just as she had done earlier in the day. I looked up at my wife and she was grinning at me. I was in heaven. I then watched as Christy took my cock into her mouth and started sucking. She was doing it much better than I expected considering she had been ordered to do it, but she seemed to enjoy it no matter the circumstances.

I was aware that my wife had moved, but I was not paying attention until I saw her come back into my field of vision. Christy’s sucking was so good that I was not paying attention to the fact that she was now naked and wearing a large strap-on dildo. It was larger than my cock! Oh man, she was going to use it on Christy! I watched transfixed as she got down on the floor behind Christy.

“Master, please sit down in that chair behind you. Christy, don’t stop sucking Master’s big hard dick.” My wife said.

So I backed up a couple of steps slowly as Christy shuffled along on her knees and then slowly lowered myself into the chair. Christy came with me, her mouth remaining connected to my hard cock. I was going to last a very short time again with this. She was very good at sucking my dick and I was watching my wife come up behind Christy.

My wife grabbed Christy’s hips and said to her, “Christy, do not quit sucking Master’s dick. I wanted to let you know that I know this kind of thing makes us all horny, including you. Mistress doesn’t want you to go back to your room unsatisfied so just relax as Mistress fucks you with a big strap-on dick.”

At the sound of that, Christy lifted her head off my dick and turned around to see what was happening. My wife shook the dick at her, lifted her skirt, and put the dick against Christy’s pussy. Christy moaned and went back to sucking my dick. I could feel Christy rocking as my wife pushed the dick against her hole. My wife didn’t go easy on her, but she didn’t try to tear up the young girl either. She was just forceful enough and when it was in a ways, Christy raised off my dick and moaned. She was really enjoying it now.

My wife started fucking Christy with the strap-on, and I knew that I was going to cum from her blowjob. I said to Christy, “Christy, Master is ready to cum, so keep sucking and don’t spill a drop.”

Christy just looked up at me and nodded. Then she closed her eyes as she also enjoyed my wife’s fucking her.

Then I exploded into her mouth. I spasmed hard and my whole body went rigid. I held on to her head and kept pumping sperm into her mouth and she kept sucking and sucking until I was done. Then I pulled out of her mouth and she started moaning loudly. It was apparent that she was about ready to cum as well. I just sat there and watched her face as she reached up and braced herself using the arms on the chair. Her face was beautiful as I watched her with her eyes closed savoring the hard fucking my wife was giving her.

“I’m c-c-cumming” she finally stammered, and started shaking and spasming. The orgasm lasted quite a while and I looked down to see that my wife was not only fucking her, but appeared to have a finger in Christy’s ass as well.

When her orgasm had subsided, she leaned forward and placed her head in my lap, her cheek resting against my limp dick. She was exhausted. My wife pulled out of her and there was quite a sucking sound as Christy’s pussy released the large dildo. My wife stood up and she was gorgeous standing there naked wearing this large strap-on covered with Christy’s juices. She reached down and slapped Christy’s ass, startling Christy out of her relaxed moment. She remembered where she was and stayed there kneeling, being very still. She was staring at my cock and probably thinking about what just happened to her.

“Did you enjoy being fucked by this dildo and sucking Master’s cock?” my wife asked her.

Christy seemed a little unsure to admit that she enjoyed it, but finally said “Yes, Mistress.”

“Good. Now there is one member of this group who is not satisfied. Do you know what that means Christy?” my wife asked as she sat down in the chair next to mine.

“Yes, Mistress.” She said, and without further prompting, she turned around on her knees and shuffled over to my wife. My wife removed the strap-on, leaned back, and opened her legs for the young girl. Her pussy was soaking wet. She was as turned on by all this as I was.

Christy looked at my wife’s cunt, which was also fairly well shaven, and started licking. My wife leaned back, turned her head toward me, and smiled. She had never told me that this was something she would do either, but all of this was new and she was enjoying being in charge of this beautiful young woman. For her part, Christy seemed to know her way around a pussy, and my wife looked like she was going to come quickly. I watched as Christy now had two fingers in my wife’s pussy and was sucking on the clit. My wife was moaning loudly, and getting close, because she grabbed Christy’s head and said “That’s it, my little cunt-licking slave, suck on my clit and fuck my cunt. Eat me all up you slut.”

And with that she came. Her orgasm was a major one. She spasmed over and over and held Christy’s head like vise grips. She kept saying, “Oh yeah, Mistress is cumming!” until her last spasm and she relaxed.

She raised Christy’s head up, looked at her, and said “You are a very good slave, young lady. Now watch your step or we may have to take more drastic action and punishment, understand?”

“Yes, Mistress.”

“Now tell Master thanks for cumming in your mouth.”

“Thank you for cumming in my mouth, Master.” Christy echoed.

“And thank me for fucking you and letting you eat my cunt.”

“Thank you, Mistress, for fucking me and letting me eat your cunt.”

“Now get back to your room.” My wife said.

After Christy left, we slowly got dressed ourselves and my wife looked at me with a twinkle in her eye. “I think you’re satisfied for now, eh big boy?”

“Whew!” I said to her. “That was the most fantastic thing I have ever seen. If I hadn’t already been blown twice by that girl, the second time just before she sucked your cunt, I would have been hard again watching that. You were just too fucking hot!”

“Well, thank you, good sir.” She said. “We’ll have to see what else we can cook up.”

I was also thinking of some things I could cook up for her. She had taken care of me, so I wanted to try something similar. I set to work on that idea while we dressed and closed up for the night.

In Chapter 5: Christy’s Back… with a friend!


Chapter 5. Christy’s Back… with a friend!

We hadn’t had any action of any kind, which was surprising and I kept mulling over different ways for my wife to get her share of attention. I was thinking about something to do with the Halloween party that was coming up while my wife and I sat in the closet one day when something very interesting happened in the ladies room. Christy, who had been punished for using the glory hole, was back, and bringing with her another girl, this time 18 year old Jennifer (Jen for short). Jen was a petite about 5’ tall girl with just enough hips and tits to make her a woman. Not extremely attractive, but cute. She was wearing a polo shirt and skirt, just like Christy.

We had not had Christy back into my office for more “punishment” in the 10 days since her last episode. We were trying to think of a way to get her back in there, but she was staying out of trouble and working hard on her schoolwork.

My wife and I were immediately at the window/mirror because this had our attention. Christy was obviously taking some sort of action.

Christy brought Jen in and said to her “I’m not kidding. You just come in here during lunch time, and if you rap on the wall at the right time, one of the boys will stick his dick through there and let you play with it. I did it a couple of weeks ago and it was way too cool!”

Jen looked at her with a smile. “You’re kidding, right? I mean, this is just a gag and you’ve been trying to get me in here to scare me or something, right?”

“No, and I can prove it. Just tap gently on the wall and see what happens.”

Jen tapped gently on the wall and looked back at Christy. “Nothing’s going to happen.” But she was about to get a surprise. My wife had already dropped my pants and was stroking my dick hard, but it didn’t need much help. She opened the hole and I stuck my dick through.

“Shit!” said Jen, and she immediately reached out and grabbed it. “I think I’m going to like this. I don’t have to worry about the drooling and pawing of those morons, just get my jollies and get out.”

Those words were sweet music to my ears.

“Go ahead and suck it” Christy was saying. “I sucked it and fucked it and it was great!” When she said this and Jen started to kneel down, I noticed the nasty grin on Christy’s face. She definitely had this planned.

When Jen’s little hands and mouth started working on my cock, I was wondering how I was ever going to give this up. It was just too good to have these anonymous young things suck my dick while my wife tickled my balls.

My wife leaned over to me and whispered. “Tell me when you are about ready to cum. I’ll go the ladies room, wave to you over the top of the next stall and then in about five seconds, fling the door open again. I want to startle them and have Jen let go of your cock so that you cum all over her face.”

“Sounds fantastic” I whispered and kissed my wife hard. She returned it and sucked on my tongue almost as good as Jen was sucking on my dick. I knew I wouldn’t last long, so I gave her the thumbs up and she left.

A minute later, Jen was still sucking when I saw my wife’s hand. I was glad, because having this little thing’s mouth on me while Christy was watching was making it hard to hold back even this long.

So I let it go and was just about to start cumming when my wife flung open the door and yelled, “Stop right there”.

Christy was standing there watching and fingering her pussy under her skirt. She jerked upright and stopped. Jen, who was still sucking my cock, pulled back and looked up just as I started cumming. I looked down as I spurted several streams of cum across the side of Jen’s face, hair, and her polo shirt. She flinched, but was so taken aback by my wife, that she didn’t move out of the way.

“What the fuck do you think you are doing?!?” my wife demanded. She stepped over and grabbed my cock as it oozed the last drops of its cum out. She got some on her hand and said to the girls, “Whose dick is this?”

They both muttered “I don’t know” and my wife moved on. She released my cock and I immediately starting getting dressed and watched my wife work. She looked at Jen and said “Were you going to swallow all the cum from that dick?”

“Yes.” Said Jen quietly, eyes down on the floor.

“And you,” my wife turned and spoke to Christy “I guess you are back for more punishment?”

Christy looked my wife right in the eye and whispered “Yes, Mistress”.

Holy shit! Christy wanted some more. She was horny and wanted to fuck and suck some more of the Mistress and Master!

Jen looked confused, but my wife just grabbed both of them by the arms and started dragging them out of the bathroom.

I went and sat back down at my desk to await the “punishments”.

My wife stormed in past my unaware assistant and said “No interruptions”. My assistant didn’t seem to bat an eye because my wife had two obviously in trouble girls.

My wife marched them over to my desk. She told Christy to assume the position, and she did immediately. She bent over, pulled her skirt up over her ass and put her hands on the desk. Jen just stared. My wife moved over to Jen and said, “That’s the position, so assume it and prepare to receive the paddle!”

Jen looked very worried, but did as she was told. I got up before my dick got hard again, but Christy was looking anyway to see if I had a boner yet. I went and sat in one of the guest chairs in front of my desk and prepared to see what my wife had going here. I took a good look at the pristine asses in front of me and my dick started to rise again anyway. Christy’s was just so beautiful and round. It was perfect! Jen’s was a little smaller, but it looked absolutely scrumptious and I licked my lips involuntarily. I could see them so well because Jen was wearing the standard thong and Christy, well, she was not wearing any underwear at all. I could see her lips where they disappeared between her thighs and they appeared to already be glistening.

My wife came back with the paddle and took in the same view. First, to Christy, she said “My, my, you are a little slut aren’t you. Wearing no underwear at all, your cunt easily seen by anyone in your classes or when you want to flash them.” Then, to Jen, she said, “And you. You are covered with cum. Your face, hair and blouse are a mess. Take off that shirt and wipe your face and hair with it.”

Jen looked back and hesitated. My wife smacked her on the ass with the paddle and said “I mean now!”

Jen quickly removed her polo, revealing no bra, and tried to get it off and start wiping her face and hair without displaying her tits to me. My wife just looked over and winked at me. She was really getting off on being in charge of these young ladies.

I smiled and pointed to my raging hard on.

This led to my wife saying, “Well, well, Jen. I see you are in also in violation of the dress code by not wearing a bra. I guess it’s not easy for us to tell because you have small tits. Christy, do you have a bra on? I hope so because you seem to have larger tits than Jen, right?”

Jen didn’t move a muscle. She seemed complete petrified.

Christy answered “Yes, Mistress, my tits are larger than Jen’s and I am wearing a bra.”

Jen then glanced at Christy, apparently over the use of the word “Mistress”, because the larger tits comment was too obvious to draw attention.

“Well, “ my wife said, “Christy, remove your blouse and bra and Jen remove your thong. I want you two to be uniform while in this office.”

“Yes, Mistress” Christy responded and started removing her polo and bra.

Jen didn’t move. She started to get up and turn around.

Smack went the paddle again. “There are no options here, young lady. I just caught you sucking dick in the ladies room through a hole in the wall. You had best cooperate.”

Slowly, Jen removed her thong and reassumed the position.

I took in the view. Christy had turned slightly so that I could get a peek at her tits, but now that she was back in position, I really had a better view as they jutted downward. They were definitely large and heavy and beautiful. The nipples were very pink and her skin was pale.

Jen, on the other hand, had slightly darker areola and bent over I could see that even her pussy lips were darker than Christy’s.

“Jen” my wife started. “You have some things to learn about these punishments if Christy has not already told you. When in this office with just the headmaster and me you will refer to me as Mistress and the headmaster as Master. You will do whatever we say and always respond whenever we ask a question repeating what we ask. Understood?”

“Yes, Mistress” Jen said, haltingly.

“Good. Now Christy, you appear to be very wet. Don’t tell me that your pussy is wet and wants some more attention!”

“Yes, Mistress, my pussy is wet and wants some more attention.”

“See how that’s done, Jen?” my wife asked.

“Yes, Mistress, I see how that’s done” responded Jen.

“OK. First, we need to apply some punishment to these asses. Master, you apply them to Christy with your hand while I apply them to Jen with the paddle. She was doing the more troubling thing.”

I moved up behind Christy and she looked sideways at me and actually smiled. Wow! She was wanting and enjoying this!

My wife landed the first smack with the paddle and Jen jumped. I then landed a good open hand on Christy, leaving my hand’s imprint on her ass. She, too, jumped. My wife landed another one on Jen, and I hit Christy’s other cheek.

My wife stepped forward and started stroking Jen’s ass. “I hope you understand why we are doing this. We don’t really want to hurt you, but you need to be taught a lesson.” And she kept stroking Jen’s ass. I decided to do the same and started lightly running my hand over Christy’s ass. She arched her back down a little and pushed her ass out some more. She actually wanted this, so as I stroked her ass, I let my fingers brush over her asshole. She moaned, which caused Jen to turn and look at Christy and see what was going on.

My wife suddenly said “Men really have a problem when there are bare tits, ass, and pussy on display, don’t they Christy?”

“Yes, Mistress, men have a problem when there are bare tits, ass, and pussy on display.” She replied.

“Well, Master has that problem and I want you to relieve it so that he can go back to concentrating on the punishment. But I want you to use a different hole this time. You sucked his dick last time and now must let him fuck you in the pussy or ass. Which do you prefer?” My wife asked, making sure it sounded as dirty as possible.

“I want him to fuck my pussy, Mistress.”

“Ask him nicely.” My wife said to her.

Christy turned and looked at me. “Master, will you please fuck my pussy?”

I looked at Christy and in my most fatherly voice said, “Yes, dear, I will fuck your pussy.”

Christy didn’t move from the desk and I dropped my pants and shorts to my ankles. I positioned myself behind her, but I wanted to taste all of her first, so I dropped down and licked her from her clit to her asshole very slowly. She moaned again and I could see Jen watching wide-eyed. I licked her a few more times and that young cunt was so delicious. It opened up and was very wet. I ran my fingers through it and her outer lips were wide open, revealing her inner lips. A very nice clit was peeking out. Her ass was also very delectable and so untouched. I knew that I wanted that next time.

I stood up and pointed my dick at her hole. I was so turned on that I thought I might come as soon as I was buried in that twat, so I did it slowly and let her pussy get used to me. She was still very young and tight. I also enjoyed grabbing those wondrous hips. I looked down at my cock disappearing in that tight young twat and at the smooth round ass. Everything was so gorgeous.

I looked over at Jen. She was watching, but also had that glazed look in her eyes, so I turned further to the left and saw that my wife was watching us and running her hands down between Jen’s legs and rubbing her pussy.

I started fucking Christy in earnest now and she kept saying “Yes, Master, fuck me!” It only made my dick harder and my fucking stronger. I wanted it to last a long time. I could feel how her cunt walls clung to my dick. It was throbbing and hot and I kept fucking and fucking and then suddenly, it was there. “I’m cumming!” I yelled, and started gushing. My orgasm was so strong and my reaction clenching so tight that when I finished, I realized I had been really clutching her hips. I was holding on so hard that I was afraid I was leaving handprints on her hips.

It all happened so fast that Christy did not have an orgasm. Everyone knew it because she was still trying to move her hips and get some fucking for it. So my wife did what every good Mistress does. She asked Christy what the rule was about satisfaction.

“Everyone has to receive satisfaction, Mistress” Christy said.

“Did you hear that, Jen?” my wife asked her.

“Yes, Mistress,” she moaned as my wife removed her hand from Jen’s pussy, “everyone has to receive satisfaction.”

“That is correct.” My wife said. “I want you to kneel behind Christy. First, you need to clean the Master’s dick of his cum and Christy’s pussy juices. Then you need to clean up Christy’s pussy and get all of Master’s cum out. You also need to makes sure that Christy has an orgasm. Do you understand?”

“Yes, Mistress, I understand.” Jen responded.

“Have you ever eaten pussy before, Jen?”

“Yes, Mistress, I have eaten pussy before.”

So Jen got down on her knees, took my dick in her little hands and started licking and sucking on my dick to clean it up. That only took a few seconds and then she was on to Christy. She put her hands on Christy’s ass and Christy arched her back pushing her ass out again. I shuffled around and pushed Christy down so that she wasn’t leaning on her hands, but had her face on the desk. Her ass was really sticking out now and Jen starting licking and sucking on Christy’s pussy. She was doing a good job from the sounds Christy was making so I decided to fondle Christy’s tits for the first time. I reached under and grabbed them. They were fleshy and heavy and the nipples were already partially distended. When I mauled them, the nipples got very hard and I could tell that Christy’s nipples were very sensitive. She was really moaning now and Jen was acquitting herself well as a cunt-licker. I then saw my wife appear just behind Jen and she was again wearing that large strap-on.

Finally, the words “I’m cumming” came from Christy and I teased her nipples as Jen sucked on her clit. She shuddered and shook and her orgasm left her gasping for breath.

“Okay, ladies” my wife said, “Now I want you two to get into a 69 position on the floor, with Christy on the bottom. We are going to take care of Jen next.”

They got into position, both eyeing the large strap-on, not out of fear, but lust. They both were hoping on getting fucked by that monster. My wife positioned herself behind Jen and told them to get started on each other’s pussies. While Christy was licking Jen, my wife moved forward and placed the strap-on at the entrance of Jen’s pussy. Jen picked up her head from eating Christy’s pussy, looked behind her, and moaned. As my wife started pushing it in, Jen groaned, “Oh, shit, that’s enormous!”

But she didn’t pull away. Quite the contrary, she arched her back and tried to help my wife get that thing plunged all the way in to her pussy. My wife got most of it in before it seemed that that was all the Jen could take. Jen exhaled audibly as my wife started picking up a rhythm and went back to eating Christy. It only took a couple of minutes and Jen shouted “Oh, Fuck!” and started shuddering and cumming and my wife pounded her and Christy clamped down on Jen’s clit. Jen spasmed for about 30 seconds and then collapsed flat onto Christy. My wife pulled the strap-on out of Jen and asked Christy to lick it clean, which she did.

“Now, ladies, it’s Mistress’ turn.” My wife announced as she stood up unbuckling the strap-on.

“Christy stand up and put this on. I need this monster in my pussy.”

Christy stood up and started putting it on.

“Lay on the floor and let me sit on it.” She commanded.

Christy lay down and my wife squatted over it. She slowly lowered herself, oohing and aahing as she did so. I was sitting there watching and my dick was again as hard as iron. Jen was just standing there watching and doing nothing to my wife said to her, “Master has that problem again and I want you to relieve him.”

Jen looked at my dick, wondering how to do so without direction of which hole to use. I just watched to see what she did. Finally, she decided to blow me and kneeled down, took my cock in her hands, lifted it, and started by licking my balls.

This was just too fantastic. I was sitting in my office with a cute young 18 year old girl licking my balls as I watched my wife and Christy. My wife was bouncing up and down on a huge strap-on dildo, moaning and rubbing her clit and tits. She was completely self-absorbed and looked fantastic as she worked towards her orgasm. Christy was doing what she could with the strap-on and her large tits were bouncing all over.

Finally, my wife screamed and yelled and came all over the dildo. As she was doing that, I knew that I was going to blow my load. Jen was getting as much of my dick in her mouth as possible and slurping up and down as fast