Dave Gets an Education Pt. 05

Megan said. "You know what to do, go ahead and get started. Each lady will let you know when you have cleaned her feet adequately. Then you can move to the next one in line. I will motivate you with this paddle and I work my upper body and shoulders in the gym every day. Hope you appreciate that."

Mrs. Baxter was watching the action with the other ladies. She knew the paddling would hurt more after I had ejaculated, and my butt could attest to that. The women continued to drink and revel in my situation. There were no more entries in my notebook, so I was hoping that this was going to end soon. They still had my demerits to deal with and I knew that would result in further corporal punishment. My butt was already red and hurting.

I was near tears when Megan finished. She swung hard. Mrs. Baxter asked the women take their seats.

"Messing with another's personal belongings is a serious offense in this house" she said. "Megan, can you suggest how he should be punished? After all, it was your things that he was messing with."

Megan thought for a minute and then smiled.

"Mrs. B" she began. "Since he was so interested in my dildo collection, I think he should get a closer look at them. I think he should experience each and every one until he can take my largest. It is over 12 inches long."

The women applauded but Mrs. Baxter didn't say a word. She was thinking of how to handle this since she had planned to bust my cherry next week.

"That is a novel Idea. I like the concept." She said. "I think that can be arranged. He will be too busy next week since I have him for his third week of training, but the following week he should be free every evening. I believe that will be the week beginning May 29th. Dave, you will report to Megan's room that night and each successive night thereafter until you can accept all of her dildos in both your mouth and your ass. She will decide when you are ready to progress to the next size."

Mrs. Baxter had thought this through. She wanted to encourage the girls to devise suitable punishments, but at the same time she wanted to be the first to fuck my ass. That is why she had plugged it when she loaned me to her sister. She knew that Prof. Williams enjoyed penetrative sex both as a receiver and as a giver. Delaying my anal punishment for a week would give her and Jessica an opportunity to break me in first, and there was nothing Mrs. Baxter enjoyed more than taking a man's anal cherry.

"Megan," added Mrs. Baxter. "I have a collection too. Maybe we can share."

Both women smiled.

"OK" she said after making the appropriate notes in the punishment book. "Who is next? Anyone have something to add?"

None of the women spoke up. I hoped that meant that the trial was nearly over.

"OK then. I have a couple of things that we need to discuss." Mrs. Baxter said.

"Dave, do you remember the conversation we had in this very room the day you moved in?" she began. "It involved living by a set of rules while you are here and the need for discipline and punishment when your performance is not appropriate. One of those rules stated that women should be respected at all times."

"Yes ma'am" I replied. "I remember."

"Then," she continued. "Would you explain why you continually looked at Jessica's legs and ignore me while I was talking to you. It is so inappropriate to stare, as you have already found out. It is worse when you ignore a woman who is trying to provide you guidance. Furthermore, since you did not report this, I can only guess that you were trying to hide this act of disrespect; and that makes you deceitful. What do you have to say for yourself?"

I knew I was busted. She had me on every count. I had no defense.

"Ma'am" I said. "This weak male was caught up in the beauty of your daughter. It was impolite of me to stare at her and I apologize to her for that indiscretion. Likewise, my attention should have been directed to you. Maybe if I had, I would not find myself in my current predicament."

I hoped my words would appease her and lessen my punishment. Given what had already happened, I didn't really believe it would.

"That was well spoken." She said. "Perhaps if you had apologized that night things would have gone easier on you, but since you didn't, I am assigning you 1 demerit for staring at Jessica's legs, another for your inattention to me and a two additional for failure to report both. I believe that brings your demerits to a total of 14.

Mrs. Baxter explained her demerit system to the ladies. The person assigned to administer the punishment chooses the position and instrument used. Normally each demerit results in 10 swats. If I received more than 10 demerits in any given week, the number of swats is doubled. There was also the possibility of losing free time or other privileges.

"Just as it should be." Said Megan.

Anne asked. "Does that mean he will receive 20 strokes for each of his 14 demerits?

"Normally that would be correct." Mrs. Baxter continued. "However, to be fair, these infractions have occurred over a two week period. Actually some occurred even prior to that. Since we were unable to meet last week, I decided that the 10 demerit rule would be doubled, therefore the 20 strokes per demerit will not occur until he gets 20 or more demerits.

Jessica had rolled a TV and DVD player into the room.

"Ladies, it is time for some home movies." Mrs. Baxter said.

Jessica pressed the play button on the DVD player. A moment later the screen came to life and showed me lying on my bed in my apartment. I had my hand around my cock and was stroking it with long slow strokes. As I approached my orgasm the strokes became faster until I erupted in a massive stream all over my stomach. It had occurred after the episode with Anne and Megan by the pool.

"Wow" Anne said. "I want some of that."

The ladies were cheering and applauding to the scene that was being shown on the screen. Three separate episodes of my masturbation were shown. Each ended with a massive eruption. The women were all worked up now. They were staring at me like a piece of meat. I didn't like the feeling.

"Dave" Mrs. Baxter said. "What is the house rule about masturbation?"

"Unauthorized masturbation is not allowed. I am supposed to be ready and able to serve any of the ladies on demand, so I am not to masturbate or even play with my penis unless told to do so." I said almost crying.

"And?" she continued.

"I am to lick up and swallow everything I shoot. Regardless of where it lands." I said.

"That is correct." She said. "Jessica, what do you suggest as punishment?"

"Hmmm," Jessica said. "I think a week with Kali would be sufficient" "I also would assign 3 demerits for his failure to report his behavior and three additional demerits for failure to consume his mess."

"OK, Dave. Do you have anything to say?" Mrs. Baxter asked.

I simply shook my head no.

"That's one week wearing my Kali's teeth chastity belt and 6 demerits." Mrs. Baxter said. "Kali will be applied after the meeting and remain on until next Thursday's meeting. Unfortunately for you, the 6 demerits brings you to 20 for the evening, so each demerit now is worth 20 swats.

Kali's teeth was a clam shell design chastity device which locked around the shaft of the penis. The original design was made out of metal and was heavy and cumbersome. The device that Mrs. Baxter owned was made from plastic. It was light weight but was still not a device you would want to wear for extended periods of time. It was applied by wrapping the device around the penis when the penis is soft. Adjustable plastic points were then screwed into the plastic housing until they made contact with the penis. Whenever the penis tries to become erect, the points would push into the penis causing discomfort. The devise could be quite painful when the points were tightened to extreme.

"If no one else has anything," Mrs. Baxter said. "I have one final video to show you. The incident occurred this afternoon. Jessica would you play the video?"

The DVD started again and the screen came to life. It showed me cleaning the upstairs windows and I knew where this was going. I looked over at Samantha and Lucy. They were watching the screen without a clue as to what was about to happen. The video continued and you could tell that I was watching something going on outside. After a few minutes they could see me unzip my zipper and pull out my cock. It was already semi-hard, and once I started stroking, it stood straight out and was hard as a rock. I'm not sure if Mrs. Baxter even knew what I was masturbating to. She only knew that it was another unapproved masturbation. I shot into my hand and wiped my hand on the paper towels I was using to clean the window. Putting my cock away, the screen went blank.

"Let's make that a month in chastity" Jessica said. "He needs to learn a lesson."

"Wait a minute Jessica" her mother said. "I want to know what Dave was watching that made him so aroused."

The other shoe fell. I knew I was toast. I was sure this explanation was going to be painful, and probably humiliating, and not just for me."

"Ah" I began. "I was looking over at the Tri Sig house. The second floor window was open and the curtains were drawn back. Two of the sisters were... ah... having sex with each other. They were rubbing each other and kissing and, well, I think you can get the picture."

Samantha and Lucy had turned beet red. I was sure they knew it was them who I saw in the window. They were looking around the room, to see if anyone else had figured out. I purposely did not reveal their identity to try and protect their modesty. Jessica wouldn't let it go.

"What exactly did you see?" She demanded. "Who were they? Did they see you?"

I recalled all I could remember about the incident. I told her that I could see well enough to recognize two of them, but I couldn't see the face of the third woman that was involved. I did remember that she was kind of tall though. I looked over at Megan and could see that she was now blushing a little. I put two and two together. It equaled four.

"Who were they?" Jessica demanded.

I hesitated as long as I could. Jessica was staring me down and most of the other women were on the edge of their seats. These women appreciated gossip, especially when it was true. I looked over at Samantha and Lucy. They had actually stood up for me earlier tonight. It broke my heart to disclose their identity.

"ASSHOLE" Samantha yelled. "You fucking pervert. How dare you spy on me? I can guarantee you will pay."

Samantha and Lucy were clearly embarrassed by the situation.

Samantha continued. "Mrs. Baxter. I think you should know something else. When Dave was helping us move the sofa he came up with the idea of using the back door to bring it in the house. I thought it was a good idea at the time but now realize that he only wanted an opportunity to see my sisters sunbathing in the back yard. There were several of my sorority sisters out there. Two were topless and one was nude. He immediately got an erection but made me promise not to tell anyone. I understand why now."

Most of this was a lie, and I suspected that Samantha was trying to get back at me. I didn't really blame her, but still, I didn't need anyone else helping me get into trouble. I had done a good enough job of that on my own. Mrs. Baxter was trying to diffuse the embarrassment that Samantha and Lucy must be feeling.

"Ladies," it was Mrs. Baxter who was speaking. "I think you will all agree that we all have our little secrets. I am sure none of us would want some of our family and friends to know what goes on behind closed doors. Some are more open about our lifestyle, others must keep a little lower key because of positions they hold in the community. I think it is safe to say that it is in the best interest of everyone that what happens or is discussed here, stays here. It's like visiting Las Vegas!"

Everyone laughed and a tense moment was diffused. Mrs. Baxter was able to threaten everyone into silence without them even realizing what she had done.

"Now" she continued. "What Dave did is inexcusable and we need to figure out an appropriate punishment for him."

"I'd like to expose him to the world. Let him know what it feels like to be on exhibit to total strangers." She said.

"Well Samantha" Mrs. Baxter continued, "I think he already can appreciate that seeing that he is standing here naked in front of a room full of women. However, I do understand your reasoning."

"How about making him suck off some other guy in front of us?" Lucy suggested.

"No." Mrs. Baxter said. "Forced homosexuality is something that I cannot condone. I have no problem with consensual male-on-male play. It is even enjoyable to watch every now and again but forcing a guy to suck someone off or take it up the ass is one thing I won't subject one of my servants to do."

She continued, "I wouldn't rule out him sucking on a strap-on though. Especially a huge one that makes him choke. When he gets it wet enough, he can even take it up his ass until he squeals like a pig."

"Yea, and do it in front of a room full of horny women" Samantha added. I've got a bunch of friends who would love to see that, and my sorority, I'm sure they would enjoy it too."

"OK. That's one suggestion." Mrs. Baxter continued. "Anyone else come up with anything?"

"I just want to beat his ass" Jessica said.

"Yea" Megan added.

Anne said. "Make him do all his work around the house naked. He will never know who might be coming to visit, or who might see him through the window. We can keep all the drapes open to improve visibility, and Samantha can spread the word to the other sororities."

"I like it" Mrs. Baxter said. "How interesting. Anyone else?"

No one made a sound. They were all curious of what Mrs. Baxter would do.

"Dave, I think you have been a very bad boy" she said. "I intentionally set you up with some situations that would cause you to fail and earn a spanking tonight, but I had no idea that you would make it so easy. What you did this afternoon was of your own doing, and I am afraid it will cost you dearly."

She continued. "You have earned 3 demerits for watching the sorority girls sunbathing in their back yard. You've also earned another 3 for not reporting it, and an additional 3 for asking Samantha to keep it quiet. You have earned two for getting an erection in front of Samantha and Lucy, and an additional two for not reporting those."

"That's what I'm talking." Jessica said.

Mrs. Baxter continued. "I am also rescinding the merit coin I bestowed upon you because you definitely had an alternative motive for helping the girls. That makes 14 additional demerits, or a total of 34. I think I will add 1 more for not reporting your masturbation this afternoon. That makes it a total of 35."

"Now, for being a peeping Tom" Mrs. Baxter said. "And for causing Samantha and Lucy such extreme embarrassment in front of their friends, you are sentenced to 30 days of nudity. You will wear nothing except for a locking collar around your neck and shoes on your feet. Shoes will have a minimum of a 4" heal. You will shave all hair from your body from the neck down and you will keep it shaved for the duration of your sentence."

"Furthermore, you know unauthorized erections are prohibited. Each of the girls will be issued a penis whip. It is a small flogger that can be used to control a naughty penis without causing permanent damage. Each time someone sees you with an erection, your penis will be whipped until the erection is gone. Be sure to record each incident in your book."

She told me the only time I would be allowed to leave the grounds was for activities approved by her. During those activities I would wear the remote control chastity device. Under my clothes I would have on my punishment uniform.

As for my demerits, she said that I would receive 20 strokes from each lady present tonight and at dinner each night until I had received my 700 strokes. This would be in addition to any other punishments I had received that day. Each woman would decide how her punishment would be performed. I was to count each stroke, thank each lady for taking the time to discipline me, and remain still throughout each punishment. Additional strokes would be added whenever I failed to comply.

"There are eight of us here tonight." Mrs. Baxter said. "That's 160 strokes. When we're done you'll only have 540 left to go. Who wants to go first?"

Samantha raised her hand. She chose the paddle and had me bend over the back of a chair with my hands firmly placed on the seat.

"I thought you were different, Dave." She said. "Not like those other assholes on campus. I thought you and I could maybe..."

She stopped speaking as I felt the impact of the first stroke. I guess she had a little experience with the paddle from all the pledge initiations she had participated in. Her blow landed dead center on the fleshy part of my butt.

"One, thank you Miss Samantha. I am sorry for watching you through the window." I said. Two, thank you..., three..."

And so it went on until I reached 20. My butt was red and I had tears in my eyes. The tears were not just from the pain of my paddling, they were also from the embarrassment I caused Samantha.

Lucy was next. She chose a riding crop. She had me bend over and grab my ankles. She swung as hard as Samantha but aimed for the crease between my upper thigh and butt. That is a very sensitive area. By the time she was done, I was crying like a baby. This didn't deter the ladies one bit. Megan was next to volunteer.

Before she started she whispered in my ear.

"You know I was the third girl you saw this afternoon. This is only the beginning of how you will be paying for your curiosity. I can't wait 'til I get you alone with my collection. By the time I am through with your ass, you will be begging me to fuck you every day!"

With those words I was back over the chair and she was beating me with the paddle. Because of her training she was able to swing harder than most of the other women there. Only Hilda's paddling could compare to the force of her impacts. By 10 strokes I was crying so much that I couldn't count. By 20 I had stood up and tried to cover my butt with my hands. I was in extreme pain.

"That will not do at all" Megan said. "Dave, I want you to bend over this desk and extend your arms in front of you palms up. Hilda. Please sit on his forearms. That's right. Good. I bet he doesn't cover up now. OK, where was I, that's right. Here comes number 1."

Megan repeated each of her 20 strokes. The position I was in was extremely uncomfortable, especially with Hilda sitting on my arms. Hilda was next. She chose her flogger and had me kneel with my arms outstretched and my forehead touching the floor. She concentrated on my back, which at least gave my butt a rest.

Anne followed Hilda. She picked up the paddle but then put it down and selected the riding crop. The welts she created crossed the ones created by Lucy. My butt looked like a steak that had just come off the grill.

The ladies took a break. Some had to pee, others had another glass of wine. None wanted to miss one stroke of the punishment. When all had returned Dr. Rosewood selected the paddle.

"I haven't held one of these since my college days." She said. "Dave, please lie on your back."

I lay on the floor on my back. She grabbed my legs and lifted them until they were doubled back over my shoulders. My ass was lifted off the ground and sticking up in the air. My thighs were stretched tight and I knew any impact to them would hurt twice as much due to the stretching. Megan sat on my legs and her ass was positioned over my face. As she put more and more weight on my legs she ended up sitting on me, her asshole covering my mouth."