Dave Gets an Education Pt. 05

"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.