Chapter 9. Fun with Christy, Jen, and Cindy.
The following Monday after a very interesting weekend with Jeremy, Jo and Jo’s slave, we returned to work refreshed. We had taken Sunday off from sex completely. We needed to recharge our batteries.
While relaxing on Sunday I had come up with some ideas. I put some clothespins into my briefcase, along with some of my wife’s toys. I also remembered seeing a set of kneeling punishment stocks at an antique store a few miles down the road. I left work at about 9:30am on Monday to run down and see if the store still had them. They did, so I bought them and brought them back to the school with me. They were in a large box, so nobody could see what they were. I retrieved a dolly and rolled them into my office and into the closet. I unboxed them, but left them there.
I had my assistant send notes to Christy, Jen, and Cindy for them to report at 4pm to the Headmaster’s office.
My wife came in about 11:30am and asked if we were going to check out the restrooms today. I said that I was going to save myself for the slaves coming to see me at 4pm. She smiled. Well, I’ll let you have your fun without me today. I think I’ll just catch up on some work and see you at home later. She left and I thought more about what my plan was.
At 4pm, the three girls appeared together at my door. I asked them in and told them to close the door. I then told them all to assume the position. They all lined up in front of my desk, leaned over, pulled up their skirts, and put their hands on the desk. Three perfect young asses stared at me. But not just three asses, also three pussies were peeking between the legs as all three had gone without underwear. I could also see that Jen and Cindy had the two butt plugs.
I told them to stay put and I went over to my closet and pulled out the stocks. They were pretty low and required the supplicant to kneel and lean forward to put their hands in the stocks. I looked at the three girls and then at the stocks. Who would be first? Cindy. She was still uninitiated into our circle.
“Cindy” I said. “You have not been properly punished by the Master and initiated into this little group. I want you to come here and get into the stocks.”
All three girls got up and Cindy looked a little uncertain at the stocks, but Christy gave her a little shove so Cindy started walking toward the stocks. She wasn’t sure she wanted to do this. I think she was just thought we had group sex. She looked like she was going to chicken out, so I said to the others “Help her into the stocks.”
“Yes, Master” they said in unison. And they grabbed Cindy tightly and led her to the stocks. Cindy didn’t fight too much, but was a little uncooperative, so Christy smacked her on the ass once and they managed to get her there. They forced her to kneel and put her hands into place, and then I lowered the top of the stocks and put the pin in place. Unfortunately, she still had her clothes on. I forgot about that, so I went to my desk and got my scissors. At first, there was a little alarm in all their eyes. I got to Cindy, lifted up the back of her shirt and started cutting. I cut it all the way up the middle and across the shoulders so that I could get it all off. Then I cut all the straps on her bra and took it off. I loved her large tits, so I grabbed them and pinched them. She jerked. I then just pulled up her skirt because it was not going to be in the way.
I pointed to her ass and said, “Jen, remove her butt plug. Christy, get the bag on my desk.”
Jen reached up and slowly removed the butt plug. While there, she quickly stroked Cindy’s pussy and ass. Cindy jerked and moaned.
Christy came back with the bag of goodies that I had brought. I pulled out the clothespins. Both Jen and Christy stared at them. Cindy couldn’t see them, but she would soon see them.
“Cindy,” I said, “You are going to be punished for putting yourself into a situation that was none of your business. I’m going to make sure that you remember this, got it?”
“Yes, Master, I understand.”
I took out some of the clothespins and went to her tits first. When she saw them her eyes went wide. I pulled and pinched on a nipple and pinned it. She went “Ouch!” and starting jerking. I did the same thing to her second tit. She looked lovely with the clothespins hanging from those big jugs.
Now I moved behind. She couldn’t see very well, but she was craning anyway to try to catch a glimpse of what I was going to do. I told Christy and Jen. “Hold her pussy lips open.”
They did as told and I put a pin on each side of her pussy lips holding them open slightly and pinching the flesh. I decided that that wasn’t enough so I put three more on each side. She now had 8 clothespins, 4 on each side of her pussy. Each time I did it, she jerked and moaned.
I stepped back and looked. It was something I always wanted to do.
I took off my clothes and stood behind her. Christy and Jen were kneeling on either side of her ass.
“Suck my cock and get it wet, both of you” I ordered them.
They slid forward and together started working on my cock. It was pretty hard in a couple of seconds, but I loved standing there watching two young things worshipping my dick. I pushed them away a little and said, “Open her ass.”
Now Cindy jumped. She had obviously never been fucked there and I was going to do it without lubrication. I just moved my dick forward and aimed it at her asshole. Christy and Jen were holding her cheeks apart.
“Please, I have never done anal” Cindy pleaded. “Please, Master”.
I slapped her ass hard and said “Shut up, cum slut. You won’t be able to say that after today. I’m taking that ass cherry right now.”
She continued pleading so I slapped her on the ass again really hard. Once on each cheek. “Shut up, you cunt!” I spat at her. “You wanted some sex, so here is some sex.” And I put my dick against her asshole. She was just whimpering now. Christy and Jen were staring at my dick and her ass. I pushed it hard and it started to go in, but it was very tight with her fighting it. I pulled back and stuck it out at Christy, who wet it very thoroughly again. Then I put it back there and pushed hard. My dick popped in and went in about three inches.
“Ooooowwwww!” came from Cindy.
I started a rhythm and knew this wouldn’t last long. I had never been this forceful and the combination of that and the very tight ass meant it would be quick.
“Pull the clothespins off her pussy, Cindy. Jen, get down there and lick her pussy and my balls.”
The other two did as they were told and with each tug of a clothespin, Cindy jerked. I could tell when they had removed them all because suddenly there was a licking on my balls and Cindy started moaning more as her pussy and clit were licked. I picked up the pace and was slamming into her now. She was moaning like crazy. I finally got ready to cum, but instead of inside her ass, I wanted to cum all over her ass and back. I pulled out and started to cum. I jerked it hard and my first few spurts were up to her shoulder blades and then the rest on her ass. I stood up straight and ordered Christy and Jen to lick up the cum. They did.
“Have you cum yet, Cindy?” I asked her.
“Nooo, Master” she said quietly and with a little whimper.
“Good. I want you to think about trying to get in the middle of something you don’t know about. You can cum only when I tell you.”
To the others I said “Jen, put on the strap on and lay down just in front of Cindy. Christy, mount the strap on. You are going to get filled up now.”
Jen put on the strap on and lay on the floor a couple of feet in front of Cindy.
“Christy, get on board the strap on.” She did.
“Now bend over and get ready to be double-fucked. She looked at me, smiled, and said, “Something I’ve always wanted to try, Master.”
She was impaled pretty good on the strap on. I lubed up her ass and my dick and scooted forward to where her asshole was calling me. I lined it up and started to push it in. I looked at Cindy. She was staring and watching intently. There were still a couple of tears on her chin.
“Isn’t this what you really want Cindy?” I asked her.
“Yes, Master.” She murmured.
I was a little stunned. She had just had her first ass-fucking and it was dry and forced and I’m sure she was sore. But she claimed she wanted to be double-fucked.
I started sliding my dick into Christy. She moaned, a lot. It was very tight and hard to get in there with the large strap on dick in her pussy taking up so much room. She leaned forward a little more to where her tits and Jen’s were mashed together. I pushed and was finally able to pop the head in. The rest went in easier. I looked at the two of them and Christy rose up a little and mashed Jen’s tits with her hands. Jen had her hands on Christy’s hips and mine were over the top of them. I was straddling both of them. I looked over at Cindy. She was completely enraptured by what she was seeing her two 18 year old classmates do to an older man.
I kept up a little rhythm and this caused Christy to slide forward so that the strap on came out a little when I pushed in and then it would go back in when I pulled back and out. She was getting an alternating fucking. I was amazed at where I was a couple of weeks ago compared to now. I wanted to fuck this young thing for hours. But I knew that I couldn’t last forever and I had further plans for Cindy. I was fucking Christy for about 5 minutes when she cried out and came. She was really having a good one and it lasted for a while. Jen was staring at Christy, watching every move on her face while she orgasmed. She seemed as interested as I was in that.
I was getting close myself, so I pulled out and turned to Cindy. “Suck my cock clean and swallow Master’s cum you cum slut.” I expected her to hesitate, but she immediately opened her mouth and started sucking for all she was worth. Obviously, she had done this before. Maybe not straight from another woman’s ass, but she could suck with the best of them. I held her head and fucked her face for a couple of minutes and then told her “Master is going to cum. Make sure you don’t spill any of Master’s wonderful seed.” All she could answer with was “Mmff.
I finally came with a big shudder and spurt down her throat. She really started sucking and swallowing hard to make sure she got it all. I gave her several big squirts and then relaxed and let her keep sucking to get it all. She did a very good job.
I looked back at Jen and Christy, and Christy was absent-mindedly rocking lightly on the strap on and rubbing Jen’s tits, but both of them were watching Cindy closely.
“Very good, Cindy” Christy said. “Maybe you do belong in this group.”
“Christy, get off Jen and stand up in front of Cindy. Jen, get behind Cindy with that strap on.”
They complied and Cindy looked a little scared again, afraid I was going to have Jen ass fuck her. But I had decided once was enough for Cindy.
“Christy,” I ordered. “Turn around and bend over the stock that is holding Cindy’s hands. Cindy, I want you to eat Christy’s pussy and ass until she comes. As soon as she comes, Jen will fuck you and you will be allowed to cum.”
Christy backed up and bent over the stock. I watched Cindy lick Christy’s ass where my dick had just been and then work her way down across her pussy to her clit. She was doing a pretty good job and Christy was having a hard time holding still. I watched for a couple of minutes and decided that she was doing a good job and that Christy would be cumming soon. Jen was kneeling behind Cindy watching. I decided that that wasn’t good enough. I wanted to fuck her, too.
“Cindy”, I said to her. “Take your mouth off Christy and suck my dick back to life.”
She turned and sucked my dick. With all the young tits, ass, and pussy around, and the smell of sex being so strong, I was already getting hard again. She had me hard in a couple of minutes.
“Okay, stop. Now what do you want Cindy?”
“I want to cum.” She said.
I slapped her on the ass hard. “What did you say?”
“Master, may I please cum?” she corrected.
“Soon, my baby, you can cum… soon.”
I pointed her back to Christy’s ass, who was looking a little disappointed that Cindy’s tongue had been absconded. I smiled at her and winked. Cindy went back to work on Christy. I bent over and yanked the last clothespin off her right nipple. “Mmmmff” she went with her tongue buried in Christy’s ass. She was doing well. The left one had fallen off, but the right one had left her nipple very sensitive. It was red and swollen and I stroked it. She squirmed and moaned. I then got on my knees and stuck my head under her and sucked it in strongly. She broke free from Christy and said “Oh, my god!”
I was ready now. I went back behind her to where Jen was dejectedly kneeling. She was feeling a little neglected. I looked down and could see that Cindy was very turned on. Her pussy lips were very red and she was leaking fluid all down her legs. Jen smiled and pointed the strap on at Cindy. I shook my head no. Again she looked disappointed.
But she perked up when I went behind her and told her to bend over. I had the lube in my hand and was lubing my dick. It was also leaking pre-cum and hard as a rock. She bent over and I looked at her delicious tiny ass. She still had the butt plug in. I pushed her forward a little and took hold of it. I twisted. She moaned. I then slowly slid it out and looked at that opening. I looked up at Cindy and Christy. Christy was enjoying it, but didn’t seem to be cumming yet. I squatted a little and put my dick easily into Jen’s ass. She moaned loudly. I told her to see how Cindy was doing with her tongue. She leaned over and licked Cindy once from her clit to her ass. Cindy yelped and quivered. She was so turned on that she was starting to shake. I then told Jen that she needed to be able to fuck Cindy while I fucked her ass. She raised up a little with my dick in her ass and scooted forward keeping me in her ass. She laid the strap on dildo on Cindy so that it was in nestled in her ass crack pointing up in the air. Cindy scooted back and moaned loudly. Christy was getting pretty close to cumming. She was squirming under Cindy’s tongue that was now probing her ass and she was rubbing her clit for all she was worth. I was slowly ass fucking Jen, and Jen was waiting for the moment to fuck Cindy. Cindy was visibly close without any touching from the way her body was now quivering. Then Christy went off like a shot. She yelled and shook and kept saying “Eat my ass, eat my ass”.
She finally collapsed on the floor and Cindy yelled “Please may I cum, Master!!!”
“Yes, you may cum. Jen, stick that fake cock in her pussy.”
Jen waited for me to be on an out stroke and lined her “dick” up with Cindy’s pussy. When I pushed hard into her ass, she let my momentum force the dick into Cindy. “Ooooohhhh!’ cried Cindy. As soon as it reached bottom, she came… in buckets. She started shaking and moaning. Her whole body was racked with spasms and she kept jerking and jerking. She was putting out so much cum from her pussy that there was a puddle on the floor. We had stopped to watch this, but now I started fucking Jen’s ass in earnest. The fake dick was pounding in Cindy who was almost delirious. Her cunt and clit were so sensitive after that long orgasm that she was cumming again. I motioned Christy over and told her to lick my ass. As soon as Christy made contact with my ass while I was fucking Jen’s ass, I came, too. I jerked and jerked and came more buckets in Jen’s ass. I removed my sensitive dick from her ass and she had stopped fucking Cindy. She pulled out and as soon as she did, Christy pushed her over and started eating her ass and my spunk out of it. She put two fingers into Jen’s pussy, licked her ass like crazy and Jen, too, came buckets. She completely soaked Christy’s face.
“Oh, god. That was fantastic Christy” she said as she collapsed to the floor.
“You bet it was” said Christy. She then moved over and cleaned up my dick. I was exhausted. But I had to get Cindy out of the stocks. I went over and opened the stocks and lifted her up. She could barely move. I lay her on the floor and she worked to catch her breath. We were all still naked.
Finally, she looked up at me and said, “Master, that was the greatest thing I have ever had happen to me in my life.”
I just smiled and patted her fine little ass.
“Okay, girls, let’s get this place picked up.” I said.
We put everything away and I expected them to leave, but they waited for a few minutes.
“What?” I asked.
Christy, always the outgoing one, spoke for them. “Master, you have to pick two of us and put the butt plugs back in before we leave. And we need another plug for the other girl.”
I smiled. This was too much fun. I put the plugs in Christy and Jen, figuring Cindy might be a little sore, but she still looked disappointed.
Chapter 10. The Sub Club.

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