The Headmaster Ch. 05

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Ağu 31, 2023 // By:analsex // No Comment

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Chapter 5. The Halloween Party

We have been at the school now since July and the Halloween Party was approaching. My wife and I decided to go out and get some costumes that covered us enough that we couldn’t be recognized if we didn’t want to be. I ended up going as a ghoul with a face mask and a completely covering robe with a hood. My wife selected, of all things, a Star Wars storm trooper with the headgear and everything. There was no way to tell who was who and you could barely tell that she was a woman.

I told her that I had a surprise for her and I could tell that she was hoping it was some young cock. I had had some chances with two young ladies and now it was her turn to get fucked by some of the students.

The party took place at the school, so there were going to be plenty of opportunities to sneak off. As an administrator, you always try to limit this, but you know that it’s going to occur.

We got there late to make sure the party was in full swing. There was a lot of dancing in the gym and there were some students in a couple of corners doing a little making out already. We moved around and talked to some of the students, trying to conceal our voices and who we were. There were many folks who had their faces covered.

Finally, I directed my wife into the library and we went back to an office in the back. We knew it would be locked to prevent anyone from getting in there, but I opened it with my pass key and led her inside. I asked her if she was ready. She said yes very quickly. I pushed her down on the desk. I then got down and, using the scissors in the office, cut away a small portion of her costume so that her pussy was exposed. No panties! Very naughty! I teased her by stroking her a couple of times. I had her turn around and bend over and it was perfect. You couldn’t see much, but you could get your dick in there and fuck her.

I tested to see if she could get a cock in her mouth, by using mine of course, and the opening was just the right size. Besides, I didn’t expect the youngsters to care or last that long.

I turned out the lights and told her to stay there and await her “gifts”.

I made my way back to the party. I knew some of the guys because of their lack of costuming, but there were some I did not. I struck up a conversation about a young lady with one and he was gushing about her tits. I then leaned over and whispered, “I have a babe back in the library waiting for me. She wants to do two of us. You want to come?”

I thought he was going to drop his teeth. “Absolutely!” he said when he recovered.

We snuck our way around a couple of corridors, avoiding everyone else until we got back to the library office. The windows from outside barely provided enough light to see anything. I moved in first and said “Hey, baby, I’m back… and I brought a friend.”

“Mmmm.” was all she said. She walked up to me, lifted my robe and grabbed my bare dick (no underwear for me either). She told the other guy, “Get your cock out, I want you to fuck me.”

He had it cock out so fast we barely had time to blink. It was already hard. Not big, but sufficient to fuck my wife with.

She bent over and said “Put it in, baby.”, He shuffled forward and she reached back and guided it into her pussy. “Mmmmm.” she said again. “That feels good.” And then she took me into her mouth.

The guy started a fast rhythm almost immediately and my wife stopped sucking my dick and turned around and said, “Slowly, slowly. I want to come, too”.

He slowed down but started moaning. My wife turned back to my dick and started sucking. I was so turned on. She was being rocked slowly back on forth onto my dick by this young guy who was fucking her. She worked on my head, sucked my balls, tried to do everything, but the rocking made it a little difficult. Suddenly, I sensed movement and looked to the doorway. Another young man was standing there with his mouth open.

“Oh, shit!” he said. “Are you guys fucking a girl in here?”

“Yeah.” I said. “If you get your dick out, you can, too.”

He got his dick out and started stroking it. It was hard instantly and this one was maybe a little larger than mine. My wife glanced over and waved him over in front of her. He stood next to me and she grabbed his dick. She switched from me to him and starting sucking him. I was standing there watching as she sucked his cock! The guy behind her was pounding into her pretty hard and I knew he wouldn’t last long. My wife was moaning and sucking and jacking me, but I knew she had a while to go yet. Much too soon, the guy in back yelled “Oh, yeah, baby, I’m cumming in your pussy!” and jerked his spunk into her cunt. My wife took it all and didn’t miss a beat with the other guy. She took her mouth off of him and said, “Now you. Fuck me!”

I added “Yeah, man. Fuck this little slut!”

My wife looked up at me and I could tell she was smiling. The first guy was still pulling his pants up when the second guy started pounding her. He was larger and pushing my wife Van Escort much closer to orgasm. The first guy stood there and continued to watch while she sucked my cock and the other young guy fucked her. He kept pounding and pounding until finally my wife let go of my cock and yelled “Oh, yes, keep pounding my pussy. I’m going to cum!” and she did. She jerked and spasmed and kept moaning and letting out little “Oh”s. The young guy then yelled, “Here I come. I’m going to fill that fucking cunt with cum!” And he jerked and spasmed and came in my wife. He stood there for a little while, letting his cock slowly shrink back up before pulling out.

“That was fantastic!” and he slapped her on her costume on her ass. The first guy said “No kidding. Give me your name and we’ll get together and do this again.”

“Sorry, stud.” my wife answered. “This is my little secret.”

They didn’t seem too concerned and turned to leave. My wife looked at my rock hard cock and said “What about you?”

“I’m okay.” I answered. “I’m going to wait to check on a couple of plugs that I know about.” I snickered and grinned.

“Good.” My wife said to me. “After you fucking me last night and those two young boys just now, I need a break. I’m going to go back to the house so that they don’t see me in this costume and rest. Let me know how it goes with the slave girls.”

“You bet.” I said. I kissed her on the mouth. Hard. The mouth that had just sucked me and some young stud. I then ran my hand down to her cunt. It was soaked and dripping cum. Between those two they left a lot of cum in there. I brought my hand up to her mouth. “Here’s some of that young cum, milady.” She licked them clean, hugged me and left.

I returned to the party to look for Christy and Jen.

The party was going full bore now, so I was having trouble finding them. Finally, I spotted Christy by her tits. Most of the young women had something on display, legs or breasts, but for some reason I just knew it when I saw the shape and size of the woman and those breasts. I sauntered up and waited for her to finish getting something to drink from the drink table.

“Hello.” I said in a voice different from my own.

“Hi.” she said, not sounding very interested.

I switched back to my normal voice and leaned closer. “Master needs to check to ensure that you followed Mistress’ instructions.”

She looked up at me, smiled, and said “Yes, Master”.

She led me by the hand over to the side of the gym near the wall. She was wearing a skirt that kind of went with her outfit, but without the mask, she could have worn it anywhere. She turned and faced the room and said. “You may check now, Master.”

I looked around. She wanted me to check right here in the gym while all of the dancing and partying went on around us. This girl was fantastic!

I turned and faced the party, too, and acted like I was putting my arm around her. In fact, I slipped my hand down to her lower back and placed it on her ass. I ran my hand over her ass a couple of times and then down to the bottom of her skirt. I lifted it enough to get my hand under there and then ran it up her legs to her ass. As soon as I got to her ass, my hand hit the rubber piece of the plug protruding outside her asshole.. It was delicious and turning me on so much that my dick was hard again.

I grabbed it and turned it a little. Christy sucked in her breath. “Ooohhh.” She cooed. “I like that.”

So I did it some more. She was starting to breathe heavily. So I leaned over a little more and ran a couple of fingers past her plug and onto her pussy. It was soaked. This girl was a sex machine!

“I think we should go somewhere so that you can satisfy Master.”

“Yes, Master, we should go somewhere so that I can satisfy you.”

Damn, I loved this game.

I led her towards my office, but she stopped me.

“Master, I must get Jen so that you can verify all of Mistress’ instructions.”

“Yes, you must. Please get her and return to my office for proper verification and satisfaction.”

“Yes, Master.” She said and she hurried away.

I went to my office, took off my robe, which left me in just a polo shirt. I had worn no pants or underwear under the robe. I sat at my desk and it left me looking somewhat proper.

There was a knock at the door and I told them to enter. Christy and Jen entered, but now they had another young girl with them. I didn’t know this youngster, but I could tell she was young. She looked to be about 17; a short-haired brunette, with overly large tits and a small, tight ass.

“Who is this?!” I demanded.

“Master, this is Cindy. She saw Jen and I put our butt plugs in and said she wanted one, too. I told her that that was very bad and that she was going to be in trouble with the Headmaster. She called me a liar and said that the Headmaster didn’t know anything about butt plugs. When Jen and I were coming in just now she was hiding outside in your assistant’s office. What should I do, Master?”

I Van Escort Bayan was lost for words at first. I was sitting behind my desk with a hard on and no pants and they bring in a totally new person. I tried to thing it through. I didn’t want to ruin a good thing and I loved all the fucking and sucking from the young girls.

I figured I better be firm.

“Cindy. What were you doing hiding outside my office? What did you think you were going to do?”

She looked at me and then said, “I wanted to see if Christy and Jen were lying. Christy said I would be in trouble and get punished if I kept talking about those things. I didn’t think it was any of your business.”

She thought she was a bold, smartass. I had a plan for that.

“Christy and Jen, show her the position.”

Christy and Jen led her rather forcefully over to the desk. Jen said “Like this!” and showed her the “position”, including lifting her skirt up over her ass.

“No way!”, said Cindy.

I looked at her firmly. “Cindy, you are going to get a paddling for being a smartass to the Headmaster and for talking about butt plugs and sex like a whore. Now get into the position. NOW!”

Cindy slowly put her hands on my desk.

“Christy, fetch the paddle.” Christy retrieved it. I continued to sit in my chair, hiding my nudity under the desk. I suddenly reached over my desk and held Cindy’s hands down.

“Christy, three smacks with the paddle.” Cindy started squirming, but I held on to her by her wrists and hands. Jen pulled Cindy’s skirt up over her ass. Christy smacked her once, twice, three times. By the third one, Cindy was almost in tears.

After number three, I looked at Cindy and said, “Are you going to try to be better and not act like such a slut?”

“I’m not a slut.” She whimpered, “I just like sex.”

“Do you like butt plugs?” I continued.

“Yeah. My sister and I started playing with them in the seventh grade.”

“Christy, come here.”

Christy came around to my side of the desk. Her eyes opened wide when she saw me without pants and my hard on sticking up.

“Bend over, putting your ass toward Cindy and show her your butt plug.” Christy obeyed.

I ran my hand over her ass and put it on the butt plug. “Are you sure about this?” I asked Cindy. I looked up and her eyes were as big as saucers. She looked at me. I was fondling Christy’s ass and holding on to her butt plug like it was a normal everyday thing.

“Yes.” she whispered.

I reached up and pushed Christy so that she bent over a little more and slowly extracted her butt plug. Playing with her ass and extracting her butt plug meant that my dick was now freely leaking pre-cum. I stood Christy up, handed her the butt plug and said, “Christy, put this butt plug into Cindy’s tight little ass.”

“Yes, Master.” she echoed, “I’ll put this butt plug into Cindy’s tight little ass”.

Cindy again looked at me incredulously. But she didn’t move. She let Christy come around behind her and push her over more at the waist. I watched her face as Christy slowly inserted it into her ass. She looked a little concerned at first, but once it was in, let out a big sigh and smiled. “I guess we have another sex lover here,” I thought.

“Cindy, I want you to go back to your room with that plug in your tight little ass. Then I want you to come back tomorrow and report to me with it already in. You understand?”

“Yes, sir.” She answered.

She stood up and Christy and Jen watched her go.

“But that was my butt plug, Master.” Christy said with just the hint of a smile.

I stood up, showing them my rock hard boner. Jen’s hands flew to her mouth. “Master! You are naked!” she exclaimed.

“Not yet.” I said as I removed my shirt. “Christy, since you lost your butt plug, I think we need to put something else up your ass, don’t you?”

“Yes, Master.”

“What do you say?”

“Master, will you please put your big hard cock in my tight little ass?” She playfully asked.

“Yes, Christy, I will put my big hard cock in your tight little ass.” I moved to one of the guest chairs and sat down. “Sit on my cock facing away from me.” I ordered. “But wait. Jen, get my dick wet.”

Jen got on her knees and took my dick into her mouth. She wet it completely and then licked my balls for good measure. She, too, was loving this game.

“Okay, Master, your big hard cock is wet enough to go into Christy’s tight little ass.”

Now Christy did as she was told and turned around. I held my dick up and she looked back between her legs and lined up her ass with my dick. She was ready because she still had lube on her ass from the butt plug. She lowered herself slowly and tried to relax her asshole. I stayed still and reached up and took hold of those wonderful hips. Her ass was just too beautiful and this will mean that all three of her holes have been mine. Wow!

She kept pushing down and I pushed up until the head popped in. As soon as it did, another two inches slipped in Escort Van because of all the pressure the two of us were putting on it. Man, was it ever tight and hot.

She slid a few more inches in and then stopped. She started rising back up.

“Christy, lean back and let me feel your tits. I want to play with your nipples.” I ordered. “Jen, get on your knees and lick my balls, my shaft, Christy’s pussy, and whatever else you can get to down there.”

They obeyed immediately. Christy leaned back and I covered her tits. I rolled them around, then pinched her nipples, eliciting a moan, and just started rolling them between my hands. We both were thrusting up and down to get a rhythm for me fucking her ass. Meanwhile, I could feel Jen licking my balls, and then moving up my shaft to lick Christy’s pussy. Man, was I hard. I felt like my dick could just break off it was so hard.

Jen was doing her job well, because I felt Christy reach for Jen’s head and felt the increase in her tempo. “Right there, oh yeah, lick my pussy, suck my clit, yeah, slut, make me come.” Christy started talking dirty to Jen and rocking hard. I knew I wasn’t far behind. Then Christy had a major orgasm. She held Jen really tight and started jerking and spasming and my cock was getting squeezed and her muscles were contracting and just as she was finishing, my dick went off in her ass. I jerked and jerked and shot a huge load into her ass. It had been building since my wife was sucking it while being fucked by those two young guys. I had so much building up, it hurt to spew it all out.

Finally, Christy and I settled down. She extracted herself from my lap and my dick slapped, completely spent against my leg. Jen wasted no time in getting in there and cleaning up my dick. She sucked every last remaining drop out of it and cleaned up the mess all around my balls and my pubic hair. I watched in amazement at her voraciousness. She didn’t want to miss a thing!

“Christy, that was fantastic.”

Christy, remembering the earlier lesson said, “Thank you, Master, for putting your big hard cock into my tight little ass and cumming in my ass. It felt wonderful.”

I looked down at Jen and said, “Still one left to be satisfied.” And Jen just smiled and nodded.

“Jen,” I said, “lay down on the desk, hang your head off the other side, and pull your legs wide apart.” She obeyed and it was a spectacular view.

I moved around to the other side and stuck my dick in her face. “I don’t know if I can get hard again after that, but I want you to suck my dick and lick my balls anyway. Christy, you get over on that side and slowly remove her butt plug. I’m going to eat her pussy, and you are going to tongue fuck her ass.”

We started working on Jen as I planned when suddenly Christy moved up and started kissing me. I realized that I had had sex with these girls, but no kissing. She was fantastic as we traded tongue sucking. I was really enjoying it and realized that between that, Jen’s pussy, and her sucking my dick and licking my balls that I was getting hard again. Wonderful!

I stopped and said to Christy “Change places.”

We swapped. Christy decided that Jen should watch what I was doing and didn’t ask her to eat her pussy, just held her legs back while Jen watched me slowly enter her pussy. Was she ever tight! I watched my head slide in and as I pulled back, her inner lips held on to me like they never wanted to let go. She was very wet, but still very small and tight and I slowly started to fuck her. Christy reached down and started massaging Jen’s clit. Jen moaned and I started fucking her good then. I started getting a rhythm and was pounding her pretty good when she yelled out that she was cumming and orgasmed all over my dick. It felt wonderful because she really released a lot of fluid when she came. Now my dick was well lubricated, so I pulled it out and aimed it at her ass. When Jen felt that she flinched, looked at me, and then nodded. I pushed. She was even tighter here and my dick didn’t want to go it at first. Christy started massaging her clit again and she relaxed a little and my dick went in. I slowly went in and out, in and out, until after about only 1 minute, she announced again that she was cumming and went off like a roman candle. I wanted to blow my load, but I wanted it to be in Christy’s mouth. I always liked the idea of ass to mouth and wanted to try it.

“Christy.” I said. “I’m going to pull my big hard cock out of Jen’s tight little ass and I want you to bend over, open your mouth, and suck my cock until I fill it with my spunk. Then I want you to share it with Jen.”

“Now?” she asked.

“Now!” I commanded. And with that I pulled out of Jen’s ass and leaned forward. Christy leaned as far as she could over Jen, barely enough to get my cock in her mouth, and I came as soon as she got there. I pumped stream after stream of my load into her mouth. Finally, I stopped and pulled back. Christy stood part of the way up, leaned over, and unlike in some of those ass to mouth movies where they just let it drip in, she opened her mouth and as my cum started to pour out, bent over and hungrily kissed Jen, swapping all my cum with her. After about 20 seconds, she stood up, smiled, and smacked her lips. Jen did the same.

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