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 as she could. I told her I was going to cum and deposited my third load of the afternoon into her mouth. She sucked and swallowed it all up.
We were all recovering, but my wife got right back to business. She got up, unbuckled the strap-on on Christy and ordered the girls back into “the position”. They obeyed immediately and didn’t look scared this time.
My wife went to her strap-on bag and came out with two small conical items, which I immediately recognized as butt plugs, and some lube.
“Ladies”, she began, “I have something for you. You will have this in whenever you are ordered to come to the Master’s office. Also, there is a Halloween Party next week for the entire school and you will wear it to that party. Master will be checking and not wearing it will bring a severe paddling. Understood?”
The two girls had turned and looked at what she was talking about and both murmured “Yes, Mistress” simultaneously.
My wife lubed the butt plugs up and slowly worked them into the two girls. It went into Christy fairly easily. It took a little more work, my wife moving it slowly in and out until it finally got past the largest part and popped into Jen.
“Stand up, ladies” My wife commanded.
They stood up.
“Check the plugs, Master” my wife turned to me and said.
I checked the plugs. It felt wonderful running my hands over the two different asses and feeling the butt plug securely in place.
“Perfect” I said.
“Okay, ladies” my wife said to the two. “Get dressed and get back to your rooms.”
And they dressed and left.
I turned to my wife. “I have now had the pleasure of a couple of young ladies in this office. What are we going to do about getting some young dick for you?”
“Not sure.” She said. “I don’t see any young men that appear to be that easily manipulated. What do you think?”
“I’m working on it.” I answered. “I’ll see what I can find out.”
She came over and kissed me and since we were still naked, I felt her ass and ran my hands over her tits. She stopped the kiss, looked up at me, and said “I still love sex with you more than anyone”, and so we went home and fucked our brains out.
Chapter 6. The Halloween Party

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