Sex stories

Sex stories




Dave Gets an Education Pt. 05

Chapter 11 Dave's training continues

For my second week of training I was to meet with Jessica for two hours a day. She was going to teach me the finer points of maid service. This included how to function at a party or formal dinner, proper etiquette, and how to dress properly. It was similar to attending a finishing school for young women.

I still had my normal chores and duties to complete, so I began my day at 7 am. I tried to get all of my required daily assignments completed by about 4. That gave me about an hour or so before dinner to relax. I would sit out by the pool or go back to my room depending on my mood. After dinner I would clean the kitchen which normally took me until about 7. I would spend the evening with Jessica finishing my day around 9 pm.

It was a long and tiring day. Ms. Hilda continued to supervise my work and occasionally gave constructive feedback on how I could do things more efficiently. Ms. Hilda and I developed a schedule that spread the work out throughout the week. It took me about 6 hours on most days to get my assignments done. Laundry day was the exception as that took me about 8 hours to complete.

The additional evening classes with Jessica helped to keep me out of trouble with the other girls. The girls would occasionally watch as I practiced setting the table or simulated serving dinner under Jessica's watchful eyes. Jessica would make me repeat various protocols over and over again until I could perform them perfectly. The girls giggled as I performed my tasks.

Next, I was given instruction in proper etiquette, especially when greeting guests. I was taught to curtsey and bow and proper eye contact.

Finally I was provided with several uniforms. I was told when and where they would be required. I was given a butler's uniform that consisted of black trousers, white button up shirt with bow tie and a short coat that had longer tails in the back. I was to wear that uniform for all formal dinners unless otherwise requested.

The second uniform was my maid's uniform. It consisted of a typical "French maid" outfit complete with garter belt and stockings. Shoes were provided which had 4" heals. Women's panties and a girdle completed the outfit. I was to wear this uniform when Mrs. Baxter had a party for her lady friends.

The last uniform was my punishment uniform. I would be required to wear it when serving guests while being punished. It consisted of a black leather collar for my neck, black thong panties, and shoes with 6" heels and an ankle strap that could be locked into place to prevent removal.

Jessica had me dress and undress in each of the uniforms until I was proficient in donning them without assistance. She had me walk in both the 4" and 6" heels until I could do so gracefully. She or one of the other girls would follow along beside me with a riding crop and smack my butt any time I lost my balance or walked 'unladylike'. By the time I had mastered bending, stooping, walking and so forth, my butt had numerous welts. Jessica tended to only strike hard enough to get my attention, but Megan provided numerous welts to my backside. Anne was not as brutal as Megan, but she got in her share of licks as well.

Jessica came down to my room twice that week to have her itch scratched. She used my tongue and my cock until she was satisfied. On Wednesday, Mrs. Baxter must have had an itch because she summoned me to her room at about 10 pm and I remained there until I had to get up and prepare for work the next day. She was very demanding in bed, and I knew whenever she summoned me, I had better be prepared to bring her to multiple orgasms.

I was cleaning the windows on Thursday afternoon when something unexpected occurred. I was looking out towards the Tri Sig house and saw some activity in one of the second floor windows. The curtains were open and I could see clearly into the room. Samantha and Lucy were standing in the middle of the room naked. I couldn't believe what I was seeing.

I continued to watch as the two beautiful sorority sisters began kissing and hugging each other. I could see Samantha massaging Lucy's large breasts. Lucy threw her head back and appeared to be moaning. I couldn't hear what was happening, but from what I could see, both girls would soon be enthralled in bringing each other to orgasm.

I continued watching for about 10 minutes. A third girl entered the room. She was taller than both Samantha and Lucy. It looked like Lucy was on her knees eating the new girl's pussy while Samantha looked on. I was getting extremely aroused and pulled my cock out as I watched. I masturbated to the sight of these beautiful women making love. After another 10 minutes all of the girls left. A few minutes later I saw Samantha and Lucy come out of the house, spread out a beach towel and stretch out on the front lawn to catch some rays. Both were wearing bikinis and had loosened their tops while they lay on the ground.

I had to get back to my work, so I finished cleaning the windows and headed downstairs. I went into the kitchen to get myself a drink and found Hilda preparing dinner. She reminded me of the meeting that night at 7 pm and told me to be sure all of my daily assignments were done by then. She also reminded me that there might be a quiz on the house rules Mrs. Baxter had given me when I moved in. I hadn't really looked at them since the night she gave them to me, so I figured I better go to my room and review them again when I finished my chores. I thanked Ms. Hilda for looking out for me.

Chapter 12 The first House meeting

I had just finished cleaning the kitchen after dinner. Hilda watched as I scrubbed the pots and pans, washed and dried the dishes, wiped the countertops and table and finally mopped the floor. I put everything away and looked at my watch. It was 6:30 so I had 30 minutes to kill before the first house meeting.

"I have to get my notebook." I said. "So I think I'll head to my apartment and take a quick shower and change clothes. See you in a little bit."

"OK Dave." She replied. "But don't be late if you know what's good for you."

I gave her a little smile and headed to my room. I took a shower, put on some fresh deodorant and a little cologne and changed into a clean t-shirt and shorts. I looked at the entries I had made in my notebook. I knew I would be receiving some punishment. Since this was our first meeting, I really didn't know what to expect. I could only hope for the best.

I arrived in the library with five minutes to spare. Mrs. Baxter was not there yet. Jessica, Hilda, Anne and Megan had all arrived and were sitting around the room. Jessica told me to remain standing for the time being. I had been waiting for a few minutes when the doorbell rang.

"Get that Dave." Jessica said.

I went to the front door and opened it. I found Samantha and Lucy standing there. I asked them why they were here and Samantha said they got an invitation to come over for wine and cheese. I let them in and showed them to the library.

Mrs. Baxter entered the room and sat in the chair behind the table. She looked around the room and smiled.

"I know Dr. Rosewood is running a little late." She said. "She will be here shortly. Are we expecting anyone else?"

There was no response so I assumed that all the women who were coming had arrived with the exception of Dr. Rosewood. Mrs. Baxter directed me to bring some cheese and wine for the ladies. Hilda said she had prepared a cheese plate and that it was in the refrigerator. I headed to the kitchen and returned with the cart. I placed the cheese plate on the table and started serving the wine. By the time I had served everyone, Dr. Rosewood had joined the merry band.

"I think we can begin now. Dave why don't you come over here and have a seat?" Mrs. Baxter said. "Let me start by introducing our guests. Samantha and Lucy live across the street in the Tri Sigma house. Samantha is President and Lucy is Treasurer. Samantha called me this afternoon to tell me what a wonderful person Dave is. She said he helped carry a new sofa into the sorority house last weekend, and that they couldn't have managed it without him."

"I invited them over tonight to join us for some wine and cheese." She continued. "Over here is Helen Rosewood. She is my personal physician and a dear friend. She visits me often, and I thought she could provide some thoughts about tonight's agenda. Please make these ladies feel welcome."

"This is the first of our weekly house meetings." Mrs. Baxter began. "The purpose of this meeting is communication. I have found that when there are so many people living in close quarters, incidents can occur that lead to arguments or even fights. The purpose of these meetings is to bring any issues out in the open and correct whatever may have created the problem."

The women were all nodding in agreement. I looked around the room, there were seven women listening attentively to Mrs. Baxter.

"In addition to preventing problems," Mrs. Baxter continued. "This is also an opportunity to hear suggestions about how the house can run smoother. It gives everyone the opportunity to make important announcements such as upcoming activities and anything else that would be beneficial for the household to know. For example, if Megan is going to be gone for the weekend playing in a softball tournament, it helps Hilda to know that she won't be here for meals. "

"Maybe we could put up one of those monthly planning calendars." said Anne. We could all write down when we will not be here. We could also schedule any activities that are planned."

"That's an excellent idea. Anne." Mrs. Baxter said. "That's the type of input I am looking for at these meetings. I will pick up a planner this week. We can put it up here in the library. That's a convenient location that everyone has access to."

"Maybe we need one to schedule time with Dave?" Megan said with a bit of a smirk on her face. "I know I want to get my hands on him one of these days and it might become a problem if several of us want to use him at the same time."

The ladies burst out in laughter. I felt about two inches tall. I glanced at Samantha. She was smiling and enjoying my humiliation. I still didn't know what she and Lucy were doing here. I thought this was a meeting for those who lived in the house.

"I'll take care of that calendar." Mrs. Baxter said. "We need to be careful not to 'overuse' Dave. After all, he can't be expected to 'get it up'... I mean stay up every night and still be able to function during the day. I think a schedule is a good Idea, but ladies; please come to me so I can coordinate your entertainment."

Dr. Rosewood spoke up. "I can provide a little help in that area, at least with the 'get it up' part. I can prescribe some little blue pills that will help Dave 'entertain' the girls. Of course, you'll have to schedule me for some entertainment time as well."

The room erupted again. There were cat calls and whistling and a few applause before Mrs. Baxter could regain control. I simply stared at the table in front of me.

"Does anyone else have any suggestions or announcements they would like to make?" Mrs. Baxter asked. "Good. Then we can get started with the business at hand. We will meet weekly to discuss performance and attitude. Most of you know that Dave has agreed to be our servant for the next two years. He is being compensated well for his service. Part of the agreement calls for him to be disciplined whenever his performance is poor, he breaks any of the house rules, or develops a poor attitude."

She continued "Each week Dave will confess any deficiencies in his performance or attitude as well as any infractions of my rules. Those present will then determine an appropriate punishment. Just to make sure that Dave reports his acts and omissions accurately, each of you living here can comment on his behavior as well. In fact, anyone can lodge a complaint against Dave and it will be investigated here."

"It's kind of like a trial and sentencing." Anne said.

"That's correct." Mrs. Baxter said. "But my courtroom he is guilty until proven innocent."

Mrs. Baxter had me give her my notebook. She looked through the entries and smiled for a moment. She then had me recite the list of rules that she gave me on my first night here. There were over 20 rules and policies that I had to remember. I forgot two.

"That's two demerits, Dave" Mrs. Baxter said as she wrote in my book. "Hilda, would you give us a summary of his initial training and performance?" Mrs. Baxter asked.

Hilda began by saying that she had been impressed by my ability to learn my duties. She said I had successfully completed all of the tasks she had been assigned to teach and that we had set up a work schedule which allowed me to perform all of my responsibilities on a regular basis. I would be scheduled to work 8 hours per day during the week and a half day on Saturday.

She said that my performance had been generally good with a couple of exceptions. First, I had failed to dust the second floor properly, failing her white glove test. Second, I had attempted to machine wash Mrs. Baxter's intimates. She made me wash all the undies of all the ladies by hand. I was required to sniff each garment prior to washing as punishment, and again after washing just to be sure they were clean. Third, I had failed to clean the glass patio doors and several windows properly, leaving them streaked. For this, she made me wash all of the windows again while she supervised with her flogger; and finally, I had failed to properly clean one the toilets in the west wing by leaving a toilet seat up. She made me clean all of the toilets over using a toothbrush to clean under the rim to ensure they were clean. That took me hours to finish.

"Dave, I don't see these events listed in your book." Mrs. Baxter said after a few minutes. "Do you wish to contest the validity of these incidents?"

"No ma'am." I replied. "I thought Hilda's discipline at the time was sufficient and they would not need further review."

"Dave." She continued. The notebook provides me a history of your behavior and work habits. All deficiencies must be recorded so that we have an accurate record of your performance. I may have chosen not to administer further discipline for these events had you recorded them properly, but since you didn't, I am assigning 1 demerit for each item and another for failure to report them. Since there were 4 items, that is 8 demerits. You're up to 10 now."

"How did he do this week, Jessica?" Mrs. Baxter asked.

"The training on proper etiquette and how to serve went fairly well. He is a quick learner. He had a bit of problem with his dress through, especially walking in heels." Jessica replied. "The girls and I had to encourage him a little with our riding crops, but he finally got it after a lot of practice and a sore butt."

Anne and Megan were giggling at Jessica's remarks. Jessica was looking straight at me shaking her head.

"I thought he had learned his lessons well, but looking at his posture here tonight, maybe I was wrong." She continued. "Stand up straight David. Lower your gaze like I taught you. Better yet, Get on your knees. Kneel before these superior women."

She thought for a moment before adding.

"I think an additional demerit is appropriate for poor posture. Mom, would you write it in his book for me?"

"Certainly honey." Mrs. Baxter said. "Anyone else wish to comment on Dave's performance before we move on to infractions of the rules?"

Samantha spoke up. "This really isn't poor performance, it is actually good performance."

Jessica gave her a dirty look and I could see hints of jealousy in her eyes. Samantha recounted the story of how I assisted them with the couch the previous weekend. Fortunately she left out the part about the naked sunbathers and my erection. The way things were going, I was sure that both would earn me a demerit or worse. Mrs. Baxter smiled and said that men should always volunteer to assist a woman in need. She gave me a merit coin which she said I could use to erase one demerit from any punishment session. I gladly gave it back to her, asking to apply it to my current circumstance. I looked at Samantha and mouthed a thank you to which she smiled.

Mrs. Baxter again asked if anyone had anything to add about my performance. No one spoke up.

"Good" she said. "Dave, bring us some more wine as it looks like these ladies are thirsty tonight.

After a short pee break the meeting resumed.

"OK Dave," Mrs. Baxter said. "I see you have an entry concerning Helen and your physical. It says you were uncooperative when she was measuring you penis. Dr. Rosewood would you like to explain what happened?"

Dr. Rosewood explained that during my physical she had me strip to examine my penis, check for hernias and perform a rectal exam. She had her nurse present as a witness as well as another nurse who was training to be a PA. She said that I initially refused to strip and that when I did, I had a semi erection. She said she wasn't sure if she should be offended by the partial erection or because my erection wasn't rock hard. In either case, it prevented her from properly measuring it as Mrs. Baxter had requested. She said she made me masturbate until I was erect, and after measuring it in the erect state, made me continue until I shot my load and I was soft.

The women were laughing as she told the story. I was actually becoming semi-erect as she told it. I had gotten use to a lot of the humiliation so the story really didn't bother me much.

Mrs. Baxter spoke. "That is an interesting story, Helen." Dave, was it accurate?"

I nodded.

"Well then." I think you should give the ladies a repeat performance. Please face the ladies, strip, and begin stroking yourself. You are not to shoot until I give you permission. You will then lick up your mess from wherever it falls. Understood?"

"Yes ma'am." I replied.

I was naked and masturbating in front of a room full of women who had been drinking wine for the past hour. I was still a little uncomfortable being naked in front of women I hardly knew, but the eroticism of what was happening excited me and soon I was hard as a rock. My cock was now dripping and I was getting close to shooting.

"Let's see what else he wrote in his little book" Mrs. Baxter said. "Megan, he wrote that he offended you and Anne with his erection. He also insulted Anne by staring at her with his tongue half hanging out of his mouth."

Megan and Anne told the group of the incident that occurred by the pool. She left out the fact that she and Anne were naked at the time and had teased me with their feet while in the hot tub. The women were looking at me with disgust.

"Megan," Mrs. Baxter said. "Why don't you help him finish his job there? Try to keep him from shooting for as long as you can. Squeezing his balls when he gets close will help. Anne, here is my paddle. I would like you to paddle his butt until he has shot his load. Megan, you can take over with the paddle while he cleans up his mess. Remember, you control where he shoots. The more he has to clean up, the longer you will get to use the paddle."

Mrs. Baxter was looking in my book and I knew there was still one entry left. I knew the outcome would be bad. Anne was still swinging away. For a novice she was quickly learning how to get my attention. Megan was working on my cock and occasionally my balls.

"Megan, it looks like you had another incident we need to discuss." Mrs. Baxter said.

Megan told the group how she found me going through her things in her bedroom. As she recounted the story, she slowed her strokes giving Anne more time to use the paddle. When she finished the story she returned to my masturbation. Anne said her arm was getting tired and that she would need to do a few more upper body exercises in the gym if this continued every week. Megan increased her masturbation of me and soon I shot all over the feet of several of the ladies. Anne handed the paddle to Megan.
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."
"Megan" Dr. Rosewood said. "I don't think he will be able to count this time. Therefore you will need to count for him. Dave, each time you feel the paddle strike your butt, you are to penetrate Megan's asshole as far as you can. You are to leave it there until she counts and then you may withdraw it. If she doesn't feel you penetrated her adequately, she will not count the stroke and it will be repeated. Now here comes number 1."

I felt the stroke on my ass. It hurt and I immediately pushed my tongue up into Megan's butthole. She pushed back to meet my tongue and gave a little sigh as if she enjoyed the sensation.

"One" she said.

The paddling continued. Megan "forgot to count" four or five times during the paddling just to extend the pleasure she was feeling with my tongue up her ass. Finally it was over and she got off my legs. They hurt from the continuous stretch and my ass was now past red and approaching a crimson color. I knew I would be bruised for days, and a similar episode was scheduled for tomorrow.

Jessica was next. She headed for the corner and selected a cane from the bucket she found there. I had never been caned before but had read stories about caning on the internet. I feared that the caning would make my other punishments feel like child's play. I braced for the worst.

The sound of the cane swishing threw the air was as bad as he actual impact. By the time Jessica was done there were 6 distinct welts on my butt, 6 on my upper thigh, 6 on my lower thigh and 2 crossing the ones lining my butt. Fortunately I did not earn any extra.

Mrs. Baxter was last to go. She chose a hairbrush and positioned me over her lap. My penis was trapped between her thighs and she clamped down on it so every movement she made rubbed it. While her strokes were not as painful as some of the others I had received, her administration of them on top of what the other ladies had administered caused me to cry once more. The added humiliation of being placed across her knee like a schoolboy further contributed to my punishment. When she was done and I stood, I realized that the friction between her legs and my penis had caused an erection. She shook her head and grabbed a ruler which she applied to my cock until it was again flaccid."

"Ladies." She said. "I believe that concludes our activities for tonight." Dave, I want you to go to your room and shave. Come back here when you are done and I will inspect your work. I will have Kali ready for you be then. I am sure you two will get well acquainted by the time the week is over."

Chapter 13 A week with Mrs. Baxter

I was miserable that weekend. Usually I had weekends off. I had finished my daily assignments by 1 pm on Saturday. I was naked, except for the collar around my neck, the shoes with 4" heels that were locked on my feet, and the Kali's bracelet that was secured to my penis. Mrs. Baxter had inspected my body shave and assisted with shaving my back and buttocks. I now was completely shaven from my neck to my feet and that alone made me self-conscious about walking around without the benefit of clothing.

Every time I walked outside to the patio or passed a window facing the street I would glance out to see if anyone was passing by. Usually there weren't, but I also had to worry about the sorority house across the street. Were they sneaking peeks from their windows? Were they taking pictures of me with their cell phones or digital cameras? Was someone coming up our sidewalk to visit Mrs. Baxter or the girls? Anne was right, the idea of not knowing who or when someone might stop by was nerve racking.

The girls teased me all that day and again on Sunday. I was required to do errands for them like bringing them drinks and snacks, rub suntan lotion on them, fetch towels and even dry them off when they got out of the pool. The constant teasing and interaction made my cock want to swell, but Kali immediately took care of that. I hoped the points had not penetrated the skin and that I was not bleeding down there. I didn't see any blood so I assumed there was no permanent damage, at least not yet.

Anne asked Mrs. Baxter if she could use me Saturday night. Mrs. Baxter agreed but said the Kali's teeth must stay on. I arrived at Anne's room about 7 pm. She was dressed in a satin negligee that didn't hide much, not that there was much I hadn't already seen. I liked Anne a lot. She was so ladylike. She dressed professionally and presented herself as a confident, business woman. She was smart and pretty and I knew she would be a successful lawyer when she left school.

In the bedroom Anne was a different person. She was demanding and insatiable. Since my cock was locked up and unavailable to her, she attacked my tongue. We kissed for a long time with her tongue penetrating my throat like a lizard catching flies. She pushed me onto my back on her bed and mounted my face. I licked her fabulous pussy for what seemed like hours. I sucked it, nibbled on it and licked it from end to end until she was screaming in ecstasy.

About 8:30 she got up to take a pee. As I waited for her to return, I realized the price my cock was paying. It was throbbing in pain from the chastity device I wore. I felt the pain while servicing Anne, but the distraction of her body made it bearable. Now, with her gone, the pain was agonizing. I was holding my penis in my hand hoping that it would somehow reduce the pain. It didn't. Finally as my penis began to retract, the pain subsided to a bearable level. Anne returned to the bedroom. She smiled at me before mounting my face. She wanted her ass licked now.

Anne probably weighed about 130 lbs. After all of the ass that had sat on my face over the past few weeks I was able to manage her weight easily. I licked her for a while causing her to squirm. I guessed that this was the first time that anyone had tongued her other hole. Finally she settled over my tongue and I pressed hard. I guess she wasn't expecting it as she gave out a little scream as I goosed her. She settled again and my tongue penetrated her.

"Oh, that feels so good." She said. "If I had known it felt like this I would have been sitting on your face hours ago. God. I think I'm going to... ah... Jesus..."

She exploded. Her love dribbled down my face she rubbed her ass across it. It seemed to last forever and I had trouble catching my breath as she nearly smothered me. Finally it subsided and she regained her composure.

"I can't wait until you get that thing off your cock." She said. "I want all of that meat inside of me as well. It has been so long since I've had a good fuck. Those college guys that are always hitting on me are just assholes, and the guys I work with at the law office...they're arrogant as hell. I need someone who will do as there told. Give themselves up for my pleasure and not worry about their own."

She continued as she repositioned to give me access to her pussy. "I can't wait until I can find my own boy-toy. I think I'll make him my slave. Just something I can use when I need it. Something that I can own until I get tired of it and then throw away, maybe even sell. Then I'll find a new one. Until then I guess I'll just have to share you with the others."

Monday I got back to my normal routine. Mrs. Baxter would be conducting my training this week and she had scheduled it from 7-11 pm each day. I completed my daily assignments paying careful attention to keep from earning any demerits. Kali kept my erections in check so I didn't have to worry about the penis whip, at least for this week. It was amazing how self-conscious I was every time I bent over. All of the girls had now seen me naked on numerous occasions, but every time one would see me bent over it was like it was happening for the first time. I got through my Monday's chores without incident and reported to Mrs. Baxter's bedroom a t 7 pm.

"Tonight we will start teaching you some of the more personal duties of being a maid." She said. "These will include things like drawing a bath, performing manicures and pedicures, and giving back and foot massages. I might even have you shampoo and brush my hair for me. I will enlist some of the other girls to serve as models for you, so I expect you will perform all of these things for each of us. I think Hilda also deserves a little pampering so I will include her as well. Let's retire to the bathroom. I think I'll begin with a nice hot bath."

And so the third week of my training began. I drew Mrs. Baxter's bath, making sure the temperature was perfect and the proper amount of soap was added to the water. I scrubbed her back and feet and anywhere else that she indicated. Once done, I dried her of and applied moisturizing cream, rubbing it into her skin as directed. When I had finished I was instructed to perform the same for Jessica and then report back to her in her bedroom.

Jessica brought me back to her mother's room about 9 pm. Mrs. Baxter asked me how I was doing with Kali and I told her we had become well acquainted with each other. Both women laughed. Mrs. Baxter told me that I was about to experience another new sensation and produced a slender cone shaped object. She told me that this was a butt plug and that I would be wearing one for the rest of the week. She said she would give me an enema to clean me out and then insert the plug into my asshole.

We went into the bathroom and I bent over the tub while she inserted the enema tube and opened the valve. She said this was a two quart enema and that I better learn to hold it all. She said she had other enema bags including one that held 4 quarts but those were typically used for punishment. This one was just to clean me out. I had to hold the enema for 15 minutes before evacuating. At least she left me alone to shit in private. Following the enema I got cleaned up and returned to her bedroom.

"This is one of my smaller butt plugs" she said. "Since you had the ball attached to your chastity device up your ass for a week, I think you should be able to take this. It is only slightly bigger than the ball. She lubed up a finger and stuck it in my ass. She twirled it around a few times inspecting my insides. She gave the lube to Jessica and told her to lube two fingers.

"When I remove my finger, stick both of yours up his ass. You can move them around in there and explore a little. Stretch him out some, but not too much. I want to see his face as I force this plug into him. It's not as fun if he is too stretched out and he doesn't wince a little."

When they were satisfied that I was ready they lubed the butt plug and slid it into place. First Mrs. Baxter inserted it in and out several times and then Jessica imitated her mother's actions. Jessica finally left it in place and I was told to kneel at their feet.

"You are to keep that plug in your ass until I remove it tomorrow night." Mrs. Baxter said. "If you feel it slipping you can push it back in. If it falls out, you will need to have one of the girls insert it for you. It will cost you a demerit if you let it slip out so be sure to record it in your book. See me if you need to use the bathroom. I will remove it and reinsert it when you are done. Now, give each of us a nice foot massage and don't stop until we tell you."

About 11 pm Mrs. Baxter allowed me to return to my room. When I got there Hilda was waiting for me.

"It's been a while since you treated me to your tongue." She said. "I think tonight would be a good time for you to service me."

I got between her legs and started licking. She threw her massive legs over my shoulders and squeezed, trapping my head between her thighs. She grabbed the only hair I had left on my body and pulled me to her. She was directing me to lick and suck her massive cunt.

"You really turned me on today" she said. "Watching you work in the nude made me want to fuck you time and time again. Too bad Kali has your cock occupied or I'd be sitting on it right now."

She was really working me over, nearing her orgasm when it happened, my butt plug slipped out of my anus. There was nothing I could do about it so I continued my service of Hilda. When I was done I asked Hilda.

"Miss Hilda, while I was serving you my butt plug fell out, would you please reinsert it for me? Mrs. Baxter said I was not allowed to reinsert it myself."

Hilda looked at me and smiled. I knew this was not good for me.

"Sure" she said, "go in the bathroom and clean it up for me. I don't want to get any of you ass juice on me."

When I returned, Hilda was sitting in a chair in my bedroom. She patted her lap indicating I should lie across it. She had put on gloves and I handed her the plug. She took a finger and pushed it into my rectum. It hurt. She hadn't used any lube and the previous lube had dried long ago. After she worked her finger around for a while she added a second finger and repeated the process. Her fingers were larger than Jessica's and I felt my asshole being stretched. Finally a third finger was added.

"I don't have any lube so I need to make sure you are really stretched out back here" she said.

She finished and pulled her fingers out, replacing them with the plug. She told me that she would be happy to repeat the process whenever I needed, but it would cost me.

"I have a collection of dildos too, and they haven't been used since Marie left." She said.

I knew what she was implying.

Tuesday went similar to Monday. My session with Mrs. Baxter involved manicures and pedicures. I gave each of the women both that night after practicing on myself over and over again. By 10 pm I was done. Mrs. Baxter said she had my enema ready and to report to her bathroom. She removed my plug and administered the enema. 30 minutes later I emerged from her bathroom with my ass clean and ready for use.

She and Jessica used their fingers to stretch me some more and then inserted the nest sized butt plug. I guessed it was 1.75" in diameter. It slid in easily after being lubricated.

"This won't do" Mrs. Baxter said. "Get me the 2" stainless plug. I think he is almost ready for the next step."

The plug was a stainless steel egg shaped ball on a narrow shaft. It had a slight curve and a handle that fit between my ass cheeks. The business end was 2" in diameter and it took a little pressure to push it past my anal opening. Mrs. Baxter repeated the insertion several times before she was satisfied with the fit. Jessica pushed it home at least 6 times before declaring it secure. It was actually fairly comfortable once inserted, but the bulb passing through the anal opening hurt each time it was inserted. My asshole burned by the time I was sent back to my room.

By Wednesday all of my demerits from the previous week had been paid in full. I had endured a spanking of at least 100 strokes each day and my ass was sore and bruised. It hurt to sit, especially with the new butt plug in place. Wednesday night I reported to Mrs. Baxter. Tonight I would learn to do her hair and perform a sensuous massage.

"By the time you are done tonight," she said. "You will have been taught all of the basic requirements of being a maid. "It will be up to you to practice your skills and perform them properly. You will have to perform all of the skills you have learned at the request of any of the girls. I'm afraid they might keep you very busy over the summer. It will be even worse for you if the girls who move in in this fall choose to use you also."

I had finished shampooing and brushing the hair of Mrs. Baxter and Jessica. Next were the back massages which took until 10 pm to complete. I was sent for my evening enema and when I returned Mrs. Baxter had a package for me. It contained my own 2 quart enema kit with various nozzles.

"You are to perform an enema on yourself daily." Mrs. Baxter said. "You will be subject to inspection by any of the girls at any time. Failure of inspection will earn demerits. Do you understand?"

"Yes ma'am." I replied.

"Now, lay over the end of my bed." She said. "And spread your legs."

I was afraid I was going to receive another paddling, which I was sure my bottom couldn't take. I spread my legs and bent over. I heard someone behind me fidgeting. I wasn't sure what was going on until Mrs. Baxter stepped into view. Around her waist was a strap-on dildo that appeared to be the size of my 8"+ cock. Behind her was Jessica with an identical pecker.

"It is said" Mrs. Baxter began. "That a woman never really owns a man until she has fucked his ass. Tonight, you will learn the meaning of those words. You will learn the meaning of penetration. It will be painful I am sure, especially with your cock restrained as it is. Many men eventually learn to like this and get an erection when a woman takes him. I'm afraid there won't be any erections for you as long as Kali is around."

"And while Mom is impaling you from one end" Jessica continued. "I'll be having at it from the other. I intend to make you deep throat my cock until you can take it without gagging. You will suck cock tonight until you can do it as well as me. And you know, I'm an expert."

Jessica thrust her cock into my mouth. I coughed and choked until she withdrew a little. She told me to swallow as she inserted it which helped to keep me from choking. She rammed it in and out until I was able to take the whole length. Then she pulled out and had me lick the bottom of the shaft and then the balls.

"Does it taste good?" she asked. "I masturbated with it for over an hour today. I would have loved to use your real cock, but it wasn't available. "Maybe tomorrow."

Her comments made my cock want to swell but they couldn't with the Kali's bracelet secured around it. Mrs. Baxter had lubricated her cock and was now ramming it home in my ass. It was about the same diameter as the butt plug I had been wearing since last night but was considerably longer.

The friction between her shaft and my anus was both stimulating and painful. I was learning to associate the two feelings. If this continued, I was afraid that I would no longer be able to get aroused unless it was associated with pain. That thought scared me.

It was approaching 11 pm and the women had been going at it for nearly an hour. I thought the ordeal would soon be over.

"Want to switch now Jessica" her mother said. "Sure, I want to bury this cock in his ass, but let me get a condom first."

Mrs. Baxter was removing the condom she had placed on her cock. Hers was going to go in my mouth now and I was glad I wouldn't have to taste my own ass. She thrust differently than Jessica but soon I got into rhythm with her. Jessica pounded my ass. Her strokes were hard and fast and soon I was trying to cry out in pain. I figured I'd be wearing diapers in the morning.

They didn't stop until after 2 am. They exchanged their cocks for a larger one and it was then that I noticed that there was another cock attached to the harness pointing into their cunts. With each thrust into my ass, they were also impaling themselves on their own cock. No wonder they thrust so hard. They each took a turn with my mouth and ass before declaring me broken. I now officially belonged to them.

I had mixed emotions when I woke up Thursday. My ass hurt. It was a burning feeling, but it also felt empty. Today was window day and I would be cleaning them in the nude. I would have to intentionally expose my naked body to the outside world. Tonight was also meeting night. I knew I had earned a few demerits, but I felt it wouldn't be nearly as severe as the previous week.

I was doing the windows on the second floor when I looked out to see half a dozen of the sisters from Tri Sig sitting in lawn chairs on their front lawn. Some had binoculars, others had cameras or cell phones. I knew what their target was. I continued my work and by the time I was done on the second floor there were a dozen women on the lawn across the street.
I still had the first floor to do. The windows downstairs were larger to allow more sunlight in. It would take longer to clean them and the view into the house would be better. As I went downstairs I saw what was happening. The sisters were actually stopping people who were walking down the sidewalk and inviting them to watch the show. By the time I was finished there were over 25 women watching. Most were college aged. Some were older and probably lived in the area.

When I was done I headed to the back of the house. I still had the windows to do back there. After a few minutes I heard the doorbell ring. I knew I had to answer it. Putting my cleaning supplies down, I went to the door.

"Hi, I'm Mrs. Saunders" the lady said not able to take her eyes off my pelvis. "Is Ruth home? I'd like to speak to her if she's available. I live next door but don't think we've met."

"No Ma'am" I replied. "My name is David and I have taken Marie's place as the mai... butler. Mrs. Baxter is in the library, I'll show you in."

She followed me to the library. She was an older lady. Not bad looking but a few extra pounds around the middle. She wore glasses and couldn't take her eyes off my butt.

"Excuse me" she said as I opened the door to the library. "What is that thing on your... your... penis?"

"It's a Kali's teeth chastity belt." I replied. "I have to wear it this week as punishment for masturbating without permission. Mrs. Baxter is in here."

Mrs. Baxter and Mrs. Saunders talked for a while. I had to fetch them some lemonade. When I returned they ended their conversation with a giggle, then resumed after I left. I knew they were talking about me.

The meeting that night was more manageable. I was able to remove the Kali's teeth and saw the numerous indentations it had caused. My cock was red and sore, but didn't look to be damaged. There were no guests present, just the girls, Mrs. Baxter and Hilda. I confessed the three episodes that my butt plug fell out and had to be reinserted and two other incidents where I had to repeat my daily assignments.

"Five demerits" Mrs. Baxter said. That is much better than last week. I think we can take care of those tonight. Remember, you also have to report to Megan on Monday to start your inspection of her dildo collection."

With that my cock started to rise. I tried to will it down but it wouldn't go. Being naked there was no way to hide what was happening. All the women were looking on. In a matter of a few seconds I was rock hard, probably the result of no sex for the past week.

"Megan" Mrs. Baxter said. "I think he likes the thought of inspecting your dildos. However, this is an unauthorized erection so get your penis whips ladies, help Dave be respectful; and Dave, that's 5 demerits, one for each of us."

That brought my weekly total to 10 and earned me 200 swats. 100 were administered that night and the remainder were administered on Friday.

Chapter 14 The Summer Class begins

The weekend went similar to the previous weekend. The only exception was that without the Kali's bracelet, my cock would get hard several times a day. Hilda offered to help me out Saturday night. By then I had already earned 3 demerits and penis whippings. Hilda's solution to keep me from having constant erections was to fuck me all night long. Most of the time she rode my cock, others were more of the standard male on top conventional sex. Once, she even let me fuck her ass.

I really let her have it in the ass, pumping her good for over 15 minutes. I exploded a huge load in her rectum. When done I was totally limp and exhausted.

"Dave" she was smiling. "You know you have to lick up your mess regardless of where it lands. Time to get busy."

I knew she must have had a reason for allowing me to do her in the ass. Sure, she seemed to enjoy it, but she also enjoyed my cleaning her afterwards. She had me start with her cunt. I had deposited several loads there. I was use to eating my own jism so that part didn't bother me a lot. Her ass was full of my semen as well as some of her own ass juice. It was disgusting and I nearly puked by the time I was done. It was nearly 4 am when I finished and Hilda wanted to snuggle for the rest of the night. I was trapped between her mammoth tits so I lay there and thought of all that had happened.

Sunday was uneventful. Hilda's plan had worked and I didn't receive any additional demerits. Jessica used my on Sunday night. I was still a little spent but able to bring her to several orgasms. She rode my cock for what seemed like hours and I ate her out until she screamed. I was afraid that she would wake up her mother and I would have to pay for that also.

Monday and Tuesday were uneventful. I did my assignments without problem and was still able to control my cock. Monday I started getting acquainted with Megan's toys. She started with her smallest dildos which I easily took both orally and anally. She was impressed and immediately moved on to something a little longer. Mrs. Baxter's training the previous week helped.

I realized Mrs. Baxter had a reason for delaying my training with Megan. She wanted to prepare me herself in a more controlled environment. I think she was afraid Megan would get carried away and do something unsafe. I appreciated Mrs. Baxter more every day. By the end of day on Tuesday I had used over half of Megan's dildos. Their size were now equal to those that Mrs. Baxter had used. I was about to enter "Virgin Territory" once again

Wednesday was June 1st. I was to start my summer class today. I had on my punishment uniform which consisted of black thong panties, my collar and shoes with 6" heels. I also had on my remote control chastity device complete with the penis plug and anal ball. The ball that was inserted into my ass was larger than the one that had been inserted previously. As I prepared to leave the house for class, Mrs. Baxter stopped me. She unlocked my shoes and told me to put on something more appropriate. She hugged me and reminded me to be careful of her sister.

"You know how cruel she can be." She said.

Class started at 8 am. There were 15 students. All were female except for me and one other. It was Jim, my former roommate. It was good to see him and we talked a little until Prof. Williams entered the room.

"It's good to see everyone here this morning" she said. "This is Business 434, an internship in business practices. It is worth a total of 8 credit hours. Six of those will be based on your performance at your assigned business. Two will be based upon the paper you will need to turn in at the end of the class. You will also turn in progress reports at the beginning of July and the beginning of August. The class will end August 30th which will give you a week until fall classes begin."

This all sounded pretty good to me. Eight credit hours meant that I could reduce my course load to 12 hours for both the fall and spring semesters. I would still qualify as a full time student, but I would have a lot more free time available.

Mrs. Baxter continued explaining the course. "I have prepared a folder for each of you. You can schedule your progress reports with me directly so there will be no formal classes after today. This is an independent learning program. You should be honored to be included as it is by invitation only. I will also be visiting with your site supervisors regularly help keep you on track. You will be paid minimum wage while performing your internship and will be expected to work at least 20 hours per week. Are there any questions?"

She handed out the folders. I walked with Jim out to the parking lot. He was a little hesitant to answer questions about what he had been up to since classes let out, but we joked and talked about our adventures over the past two years. We opened our packets. Mine said to report to 9116 Peppermint Springs Ave. and speak with Claire Winslow who was the owner of the business. Jim was to report to 4799 New Hope Way and speak with Stephanie Charles. Neither address looked familiar to us. We did think it unusual that the names of the businesses were not included. The folder also included the topic of our final paper. "Discuss the challenges that women face competing with men in today's society." Things were beginning to make sense to me but I wasn't sure where Jim fit in.

We looked at each other, both confused. We didn't say anything, just said our goodbyes and headed off to our respective addresses. I had never heard of Peppermint Springs Ave. I used my phone to google it It was across town in one of the upscale shopping centers. It took me about 30 minutes to get there. It was a little after 9 am. I read the sign above the door. It read Boutique le Femme. The name sounded familiar but I couldn't place it. I walked in and was greeted by a beautiful young woman who was about my age. It was Samantha and this was where she worked.

"Ah, hi Samantha." I said. "How have you been?"

She gave me an icy stare. It was obvious that she had not forgotten or forgiven me for my voyeurism.

"What are you doing here?" she asked. "And I think Miss Stevens is more appropriate."

"I'm here to see Ms. Clare Winslow." I replied. "I'm supposed to do an internship here this summer for a class I'm taking. Prof. Williams set it up."

"I'm Mrs. Winslow." A dark haired older woman said as she approached me and Samantha. "My guess is you're Dave Robinson and Edna Williams sent you here. It's good to meet you. I see you already know Sam. Let's go into my office to talk for a bit then I will introduce you to the other employees."

The Boutique was in a two story building. The first floor was filled with clothing as you would expect to see in a Boutique. There was everything from casual attire to formal evening wear. I saw short dresses, long gowns, business attire and everything in between. There was even an area for footwear. It was definitely your one stop shop for the professional woman on the go. It was quite a large shop. The fitting area was not your typical cubical with a curtain that could be drawn to cover the door. There was a lounge with comfortable chairs and two sofas that could be used for patrons to wait while their shopping partners tried on their outfits.

Off of the lounge area were six individual dressing rooms, and to the left of the lounge area was the checkout area. It was obvious that the women who shopped here didn't stand in line to pay for their purchases. The staff waited on them hand and foot. There were several women in the lounge as I passed by. They were drinking coffee and gossiping and paid no attention to me.

I followed Mrs. Winslow up the stairs. At the top we turned towards the back of the store to what was apparently the administrative offices. There were several private offices, some cubicles which were set up as work areas and a conference room that could hold a dozen people. Towards the front of the store were some more dressing areas and smaller showrooms that lined both sides of the hallway.

We entered Ms. Winslow's office and she took a seat behind a large Mahogany desk. There were a couple of straight chairs facing the desk and I stood by them waiting to be invited to sit down.

"Edna told me about how polite you are" she began. "Please, sit down. Would you like coffee or something to drink?"

"No thank you" I said. "Ma'am, I'm a little confused as to why Prof. Williams sent me here to serve as an intern. I don't know anything about fashion."

Mrs. Winslow said. "Let me explain a little about my operation. I have customers who drive hundreds of miles to shop here. Do you know why that is, Dave? It's not because of the clothes I sell. Most of my wares can be bought in any Boutique across the country. I do have a few private labels that I sell that are exclusive, but most of what I offer is not something that is unique to this shop. The reason people come here is service. I cater to their needs, their wants and their desires. That is why my customers are loyal to me. They pay a premium price and expect premium service."

"That is a little unusual in today's business world.' I replied. "Your overhead must be incredible. Businesses today are trying to cut corners. The internet has made shopping so convenient that people don't go out shopping and everyone is looking for the best price. It's amazing that you can compete."

"That's a man's attitude." She said. "And maybe that's why Edna sent you here to me. She wants you to understand that there are other ways to be successful in today's society. You, as a man, are looking to cut costs and maximize profits while maintaining low costs. I, as a woman, am trying to maximize profits by providing service at any cost. I'm not selling clothing her. I'm pampering the customer. Giving them what they want and need, or at least think they need."

She continued. "My profit margin is three times that of the big box or chain stores. I don't try to compete with them because they can't provide what I provide. Service. If one of my customer's needs an evening gown for a party tonight, she can come here and purchase one. If it doesn't fit just right, I'll have it altered and delivered to her doorstep. If she decides tomorrow that she doesn't like it for whatever reason, she can return it for a full refund. It almost never happens, but my customers know that I offer those services and are willing to pay a few dollars more for it."

She explained that her customers were not the everyday housewives who shopped at the local shopping mall. Her customers were lawyers, doctors, politicians or their wives. They were women who expected to get what they want at any price. Money was secondary. Service was everything.

"I see what you mean." I said. "I understand the concept, and even understand how and why it works for you; but it isn't a business plan that would work for everyone."

"You are correct." she said. "But what business plan will work for everyone. Each individual must find their niche and exploit it. I was fortunate to have a financial backer who helped me get started when I finished college. I studied business and accounting and all the other BS that you are learning now; but my passion was fashion. I didn't get a degree in it, but I read everything I could, made some contacts and was able to open my own place."

"That's an interesting way to look at it." I said. "You're right when you say that a lot of what is taught in college is BS. Sometimes I think the professors in college lack the experience of living what they are trying to teach. They talk of the theory, but have never applied it to the real world."

"That's what I like about Edna" she continued. "She teaches real world which is why I participate in her internship project. The lady that financed me is her sister. She's my silent partner now and gets 25% of the profits. She lets me run the business the way I want. She has made a lot of money from her investment, but she uses that money to help others get started so I really don't mind. It's like I am helping someone else get started too, and I like that."

"Ruth Baxter is your partner?" I asked.

Things were falling into place now. I could see that Ruth Baxter's influence was one again at work. Between her sister and friends she was controlling my life more and more. I understood what Jessica had told me several weeks earlier was true. She had said that her mother could destroy me any time she wanted, and now I believed her.

Mrs. Winslow explained that she hired highly capable people to staff her store. She said keeping good people motivated is one of the most challenging aspects of management. Empowering the employee is one way to improve motivation. That is why all of her regular employees were assigned responsibilities and made department heads. Amy is in charge of advertising and marketing and Beth takes care of the books and payroll; Cindy is the personnel manager and Denise is in charge of display; Dawn is charge of purchasing and finally there was Robin who is in charge of customer service.

"All of these women are leaders and part of the management team." Mrs. Winslow said. "Part of their day is spent on the sales floor and the rest is spent managing their departments. They are more than sales associates. That is what keeps them motivated."

Mrs. Winslow had some part time employees as well. Most were college students who wanted to pick up extra money or take advantage of the huge employee discounts that Mrs. Winslow offered. In all, there were 6 additional girls, including Samantha and Lucy who worked part time and during the summer.

Mrs. Winslow said the intern program lasted for 12 weeks so she would assign me to each department head for a two week period. That way I would see all aspects of the business. She reminded me that manners were important and that all the women who shopped here were to be addressed as Madam or Ma'am. She indicated that she would like me to work every Tuesday and Friday and every other Saturday.

"Ma'am" I said. "I think I understand why Prof. Williams assigned me here, but I really don't know anything about ladies apparel. I'm not sure how helpful I'll be on the sales floor."

"Since you will always be working with one of my other sales associates" she said. "That shouldn't be a problem. I am sure they will find ways that you can assist customers. You can also help by stocking shelves, straightening merchandise, and answering the phone."

"Very well Ma'am" I said. "Is there anything else I need to know?"

"I'm sure there is" she said. "But it will all work itself out. Let's go meet the girls. I know you already know Sam."

I was to report for work on Friday at 8 am. I arrived home about 5 pm and went to my room to take off my clothes. I reported to Hilda to serve dinner. I was again naked except for my collar and high heel shoes.

Mrs. Baxter wanted to know where I had been all day. I told her I had an orientation for my internship at the Boutique le Femme.

"Claire Winslow?" she asked, "you're doing your internship with Claire Winslow? How appropriate. Maybe you can learn something about fashion while you are there. That might earn you some brownie points with the girls here. They all shop at Claire's because I let them charge everything to my corporate account so they get a huge discount. Hmmm, how funny, working for Claire Winslow."

"Yes ma'am." I said. "She wants me there every Tuesday and Friday and every other Saturday so I will need to modify my daily routine to accommodate my school schedule."

"Very well.' She said. "Get with Hilda and come up with something that is workable. I'll review it when you're done."

I went to the kitchen and had dinner with Hilda. We looked over my schedule and figured out a plan. My only free time would be on Sunday.

I had to report to Megan's room at 7pm for training. She was not alone when I arrived. Hilda and Mrs. Baxter were also there. Each had a dildo strapped around their waist. Each was larger than any I had taken before. I was bent over the end of the bed. Hilda was lying there holding her fake penis with both hands.

"Come on big boy." She said. "Suck on my cock. Make me wet so I can fuck you with it."

It seemed like her cock kept going and going as I stuck it in my mouth and tried to deep throat it. I was choking as I felt the lubed end of Megan's dong touch my anus. She hadn't bothered to stretch me first. This was going to be a cold blooded rape of my asshole.

"Go ahead Megan." Mrs. Baxter said. "Pretend its Lucy and ram it home."

Evidently Mrs. Baxter had put 2 and 2 together the other night and knew it was Megan who had been in the room with Samantha and Lucy. Megan didn't have to be told twice and with a violent thrust pushed her cock half way into my ass. She withdrew slightly then pushed again until it was all the way in. I could feel her balls against my asshole. The thrust forced me to impale my mouth on Hilda's cock. I was split in two. My mouth and ass were both full of cock, and a third one was waiting its turn.
Both women began ramming their monsters home. They pushed together so I could not escape the effect of their thrusts. It continued until Hilda grabbed my head and held me tight against her cock. She screamed as her orgasm rushed through her. Megan was not far behind as her orgasm hit minutes after Hilda's. She rammed it home until her orgasm was complete. Both women withdrew their instruments of destruction. I was hard as a rock.

The women switched positions. It was Hilda lined up behind me and Mrs. Baxter poised at my head. Megan watched.

"Take it bitch" Hilda was saying. "Take all 12" of my fake cock. It's longer and thicker than anything you got. If I had these women for a night and used this on them, they'd never want your little thing in them again. The only thing you would be good for is that tongue for cleanup and your ass for fucking."

It was after 11pm when they finished with me. 4 hours of fucking and sucking and both my asshole and tongue had suffered. Each of the women came multiple times. There were still several dildos left in Megan's collection that I hadn't experienced. They were about the same length as the monsters I took tonight, but their girth was bigger. I was sure my asshole would never recover once I had taken all Megan had to offer.

Chapter 15 Work begins

I made through meeting night with minimal discomfort. I had a few demerits for unauthorized erections. I presented my new daily schedule and some of the women were upset that I would not have as much time to serve them. Mrs. Baxter reminded them that my school work came first. Mrs. Baxter also announced that her daughters would be visiting over the 4th of July holiday and would probably stay for about a week. They would occupy the unused 2nd floor suite and would double up as necessary while staying here.

Friday was my first day at the Boutique. Amy was off that day taking a three day weekend. Mrs. Winslow and the five other department heads were there along with Samantha and Lucy. I showed up a few minutes early. I was assigned to Robin who was in charge of customer service.

Robin was about 30. She was a little pudgy but cute enough. She wore glasses which hid some of the nicer features of her face. She wasn't wearing any rings so I assumed she was single. She was wearing a knee length skirt and white button up blouse. I could see her nipples start to liven up as she approached me.

"What's this?" she asked.

"I'll bet I know." said Samantha.

"Ah, it's my collar," I said.

"Yea," Samantha interjected. "Mrs. Baxter caught him spying on some of the girls and made him wear a punishment uniform under his regular clothes. You should see what else he has on."

The women all looked at me. Ms. Winslow demanded an explanation. I gave them a brief history of my situation and explained that Mrs. Baxter requires me to wear a punishment uniform whenever I leave the house. I have to wear it for another 3 weeks.

Ms. Winslow looked me over. She had me follow her back to the fitting area and the rest of the women followed her back.

"Take a seat ladies" she said. "This might be interesting. Strip Dave, let's see what you got."

I looked at her for a moment. I wasn't sure if she was already in on this and was just putting on an act. She knew both Prof. Williams and Mrs. Baxter and my guess was they had already briefed her about my situation. I wasn't sure if the rest of the employees were in on it or not, but they were anxiously awaiting the show.

I removed my shirt which revealed my locked collar and shaved chest. Even Samantha had not seen me since I had shaved. I heard a few catcalls and an occasional whistle. Soon they were chanting 'take it off'. I removed my shoes and then my pants to reveal my black thong panties which barely covered my cock.

"That too" Ms. Winslow said. We want to see the whole package."

I removed the panties and all that was left was my chastity device and my hairless cock. Ms. Winslow made me explain how the device worked. I explained everything including the ball up my ass and the remote control shocker. She looked me over for a while and then smiled.

"Leave it to Ruth" she said. "Girls, pick up his clothes. He can keep the shoes and his thong, but lock everything else up in my office. I'll be back in a minute."

It was about 10 minutes before Ms. Winslow returned. She spoke with Robin for a few minutes. Robin told me to follow her upstairs. It was nearly time to open for business and Ms. Winslow told everyone else to get ready to open up. I couldn't believe she was going to keep me like this. As I followed Robin up the stairs I couldn't help noticing how good she looked from behind. Her ass filled out her skirt nicely and I imagined my face buried between her ample cheeks.

"In addition to selling women's apparel," Robin was saying. "We offer women some special accessories. We have an entire collection of fetish wear and toys in the show rooms up here. Only those over the age of 18 are allowed in the upstairs showroom. Up here I am sure that you will not offend anyone with the way you are dressed."

Robin led me into the first showroom. The sign said 'Women's apparel'. The room was full of fetish clothing. There were leather, rubber and vinyl outfits. I had seen similar clothing on the internet. It was a huge collection and as I walked through the display I could feel my cock pushing against its cage. The next showroom had a sign that said 'Intimate apparel'. There were all types of lingerie and erotic underwear. Some were open in the front or back to allow access without removing the garment. Many items were see through or nearly see through. My cock was still trying to escape.

A third showroom had a sign that said 'The dungeon'. I walked in and there was a wall with various whips and paddles displayed. Riding crops made up another display. The show case had a display of various types of chastity belts and cock restraints. I even saw Kali laying on a display counter. There was a display of canes of different sizes and a wall full of dildos and strap-on harnesses. Another show case contained clamps for use on the nipples or cock. The room was full of devices designed to discipline or punish. I recognized some of the items from browsing the internet. There were racks and crosses; a row of spanking benches and various queening chairs. There were chains and pulleys and things I didn't know the names of.

"Dave," Robin began. "Claire provides a special service to some of her clientele. Many of the women who come here are dominant. Some dominate other women, others dominate men. We cater to both."

She said I was to help out up here whenever I was not assigned to work with one of the department heads. When working with them I would be confined to their office and my appearance would not matter.

"Go ahead and start looking through the merchandise." She said. "You need to be familiar with what we sell. You can even try it out if you like."

She laughed at what she said and left me to explore. A few minutes later Ms. Winslow came to see me. She said she had talked to Mrs. Baxter and she had confirmed everything I said. She also said that Mrs. Baxter had told her to let her know if I misbehaved.

"Ruth said I needed to keep a close eye on you." Ms. Winslow said. "Keep a notebook and report any inappropriate behavior she said. She also told me you have an excellent tongue and I was free to use you any way I want. I think I'm going to have fun with this internship."

She told me to keep busy until Robin had time to work with me. I could straighten and dust he merchandise while I was waiting for customers.

I was dusting the spanking benches when I felt a jolt to my penis. Someone had activated the remote control to my chastity device. I looked around and saw Megan and Samantha standing in the doorway. Samantha had the remote.

"Megan was nice enough to bring her remote down to me." Samantha said. "It really gets your attention doesn't it?"

"Yes ma'am" I replied.

Samantha and Megan looked around the store.

"I think I need a new dildo." Megan said. "There's this guy I want to fuck and he's a size queen. What do you have in a supersized model?"

They looked through the selection and picked out a couple that looked gigantic to me. I knew where they would eventually end up, but I said nothing.

"Put them on Mrs. Baxter's account" Megan said. "And why don't you come over tonight when you get off. You can help me try them out. Bring Lucy with you. I haven't seen her for ages."

They left me to my thoughts and I resumed my dusting. It was about 45 minutes later when Robin came into the dungeon with another woman who I had never met.

"This is Mrs. Riley," Dave. "She is the wife of Jude Riley. I'm sure you have head of him. She is interested in some nipple clamps. Can you help her out with that? I'll be back in a few minutes."

Robin left me with Mrs. Riley and I showed her the showcase that contained the clamps.

"I don't know" she said. "Some of the ones I buy on line just don't seem to last and they tend to slip if you tug on them. I really need something with a good grip. What do you have? I really like to pull on them or hang weights from them."

I got several different clamps from the case. Some looked like normal clothes pins connected by a chain, others were the cloverleaf type and one pair had spring loaded alligator teeth. She picked up each pair and operated tem

"Well, Mrs. Riley," Robin said. "What do you think?"

"I don't know. She said. I really wish I could try them out. It would make my decision so much easier."

"Dave" Robin said. "Lend us your nipples. Go ahead Mrs. Riley, you may use Dave's nipples if you like."

"Really?" she said. "In that case, let me try these two pair of cloverleaf clamps. And the ones with the alligator teeth to. They look interesting. Do you have any weights I can attach?"

"Sure" Robin said. "You might want to try this also. We just got it in. It's called the tower of pain. You place it between his nipples and attach the clamps. When you screw this yoke it pulls on the nipples. You can continue to screw until it pulls the clamp completely off, or stop just before its ready to let go. That's when it is most painful."

I gave Robin a dirty look and she just smiled. Mrs. Riley tried each set of clamps by applying them then pulling on the chain until the released. She did this several times with each pair. She attached weights to test their holding power. Finally she decided on a pair of the cloverleaf style and the alligator type. Next she tried out the tower of pain. It worked just like Robin said. It was as painful as anything I had experienced thus far. Mrs. Riley bought that as well.

"I'll be back soon" Mrs. Riley said. "It's so much more fun shopping when you can sample the merchandise."

I spent the afternoon in Robin's office. We watched various videos dealing with providing good customer service. She said all of the employees watched these videos so that everyone approached customer service in the same way. She showed me the closed circuit TV system. She said she could watch videos of how the staff dealt with customers. She played the tape of my experience with Mrs. Riley.

"That's what we mean by customer service," she said. "Give the customer what they want. Let's pretend I'm a customer. The service I want is between my legs. Get on your knees and give it to me. Ms. Winslow said you are supposed to have a talented tongue. We'll use the rest of the afternoon to test that theory."

gets   education   dave  

May 9, 2018 in bdsm

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