Chapter 1

After leaving Michael’s office on Friday, Angela made only one additional small sale, but did well on Saturday and Sunday, putting her well above her goal for the week and a good start on week three. She was glad Michael had given her the extra cash since it would still be another week before she got paid. She had calculated how much gas she would need and put in just enough to get her by, leaving her a few dollars for groceries and soda.

When she arrived home on Sunday, Dawn told her a package had been delivered for her and was in her room. She also said she had roasted a chicken for dinner and asked her if she wanted to join her.

Angela accepted then went to her room to change and see who sent the package and what it contained. There was no return address on the package, so she opened it. Inside was a note with a list of instructions that she was to follow to the letter.

At exactly 10:00 am Monday morning, she was to be at a certain address. The package also contained a small red box she was to take with her unopened. She was to do what they told her. When she was done there, she was given another address to go to. It was a lingerie store and an account had been set up for her. She was to purchase three new bras. One was to be red, another black and the third was her choice. They were to be the type that opened in the front.

She was also to pick out several garter belts and a half dozen pairs of nylons. The note went on to say that after today, she was to no longer wear panties when she was out. When she was done there, she was to go to the women’s section at Jergen’s department store and ask for Amy. Amy would help her pick out some new clothes. Angela was unsure what to make of this, but would do as she was told. She wanted to please her Master and he must care for her or why would he do this.

Angela dug further into the package and found several additional items, numbered sequentially. Some of the boxes had notes with a note telling her what it was and how it was to be used. The first box contained three different sized butt plugs and a bottle of lubrication. She was to start using the first one immediately. She was to use the lubrication to help her put it in and was to fuck her ass with it for ten minutes.

When the ten minutes were up, she was to leave it inside her for an hour. If it came out during that time, she was to start the hour over. When the hour was up, she had to remove it. She was to repeat the process two hours later. On Monday morning, before her first appointment, she was to use the second plug. She should fuck her ass with it for ten minutes, then leave it inserted the remainder of the day until she got home. She was to use the same plug on Tuesday and wear it to work.

The second box contained a pair of heels. They were at least three and a half inches high. She was to wear these to work from now on. The third box contained a choker type necklace. A small charm in the shape of a pair of handcuffs served as a clasp. She was to put it on and wear it all the time. She was to leave the remainder of the boxes unopened until she was told to open them.

Angela took the necklace and put it on. It was just a little bit tight, but she left it on, hoping she would get used to it. She was more concerned about the butt plugs. One of the guys she had dated had wanted to fuck her in the ass, but she had resisted. She had finally let him put one finger in her, but it was so painful, she made him stop and never let him try again. Even the smallest of the plugs was twice the size of a finger. She did not know how she was going to get that inside her, let alone the second or third one, which was HUGE!

Still, she was determined to try. She decided to first use one of her fingers. She took the lube and generously coated her fingers and spread it around her rim. She slowly tried to push her finger in, but kept tensing up. She forced herself to relax some and her finger finally went in. She moved it in and out a bit, then added some additional lube. This time, she tried to work a second finger in and was able to get them in about halfway. Then she took the first plug and put some lube on it. She reached around and pushed it in.

She heard it pop as it cleared the muscle, but it hurt like hell. She just lay there for a few minutes until the pain subsided a bit, then slowly started working it in and out. The more she moved it, the more she relaxed, which helped ease the pain. She was beginning to enjoy the sensations she was feeling. She watched the clock closely and stopped when the ten minutes was up. She left it inside her and put on a thong. She tried to wipe some of the excess lube off, then put on some jeans and a t-shirt and went out for dinner.

Angela was sure she was walking funny and that Dawn would notice, but if she did, nothing was said. Dawn did ask her how the job was going and she told her about the sales she had made. Angela had told Dawn about the fact that she had to wait three weeks for her first paycheck, and would pay her rent as soon as the check was in the bank. She did not tell her about the sessions with Michael or anything else that had happened. When Dawn asked her what was in the package, she just said it was some stuff she had asked her parents to send her.

Angela kept an eye on the clock, waiting for the hour to pass so she could remove the plug. It was very disconcerting as sometimes it pressed her wrong and made her feel very full like she had to go, but at other times, was very arousing. When the hour was up, she excused herself and went back to her room. She removed the plug and immediately felt the need to use the bathroom. Her hole was very sore and stung when she touched it. She would have to watch that. Surely, Michael would not expect her to continue using it if it was causing her pain like that.

She went back out to the living room to watch TV with Dawn. After two hours, she excused herself saying she was going to read awhile before going to bed. She lubed up the butt plug again and pushed it inside her. She felt the sting where her skin had been stretched. Her anus was very tender and it was several minutes before she could bring herself to start fucking her ass.

She finally started moving it in and out slowly. With her free hand, she began to play with her nipples and tits. She soon found herself on the edge of an orgasm and suddenly wondered if it was ok. Michael had not told her she could, but he had not forbidden it either. She finally decided she could and let herself climax. She left the plug in and pulled out a book to read.

Chapter 2

When the hour was up, she removed the plug and used the toilet. There was more stinging and soreness than before. Angela was not sure what to do. She did not want to disobey her Master, but if she was hurting this much from the small plug, what would the bigger plug do to her? She decided she would not wear the plug tomorrow or Tuesday and would talk to him about it when she saw him at work. She woke up in the morning and showered. She had some breakfast and went to the first address.

She went in and gave them her name. She was shown into a private room and told to strip, then lay down on the table face down. She did as she was told; wondering what was going to happen next. After several minutes, a man with a number of tattoos came into the room. He walked over to her and pulled her cheeks apart. He stopped and walked to a phone. He dialed a number and answered several questions, then handed the phone to her. She took the phone.

“Hello?”

“Hello WHAT???”

“Sir. Uh hello sir.”

“Hello Master!!”

“Hello Master.”

“Why aren’t you wearing the butt plug. I gave you very clear instructions to use the smaller butt plug yesterday and to put in the second one today. Did you even use the one yesterday? Do you think you can disobey me just because you are not right in front of me?”

“Master. I did use the smaller one yesterday, twice. Just as you instructed me to. But I have never had anything in my ass before and it really hurt me, making my ass sting very badly. It was still very sore this morning. I did not know what to do. I was going to tell you about it tomorrow. I was not trying to disobey you, but did not know how to reach you. Please Master, I am sorry.”

“Put Joseph back on the phone.”

“Yes Master.”

She handed the phone back to Joseph who listened for awhile, then said OK and hung up the phone.

"Your Master loves tattoos on women. He and I have discussed several which he would love to see on you. Do you want to please your Master and make yourself more beautiful for him?"

"Yes, I will do whatever my Master wishes. I want to be beautiful for him."

“Your Master says you are to be disciplined for disobeying his instructions. However, since you felt you had a good reason, I am only to give you a dozen strokes on your ass. After that, I am to give you the tattoo he requested, but am not to use any anesthetic to numb you. I am also to help you with your problem.”

Angela suddenly became concerned. She was getting used to Michael being her Master, but she had never met this man before. Now she was lying face down on a table; her ass and pussy fully exposed. He said she was going to get a tattoo, but she had no idea what it would be though if her Master wanted it, then she did too. He also said her Master had approved some sort of discipline and that this man was going to help her with her problem.

Joseph started tattooing one of her cheeks. After awhile, a girl came into the room. She put on a pair of latex gloves and opened up a jar. She took a big glop of something and walked to the other side of the table from Joseph, who walked off saying he would return shortly. Angela felt the girl’s hands pushing between her cheeks and rimming her ass. The girl was telling her to relax. When Angela continued to tense up, she felt the girl start to rub her clit.

The girl was good. She brought Angela up to a point, then let her back down. Angela found herself concentrating on the feelings in her clit and pussy and not the pain from the tattoo. She did not even realize that the girl had put a finger up her ass until she felt a second finger go in. It felt like she had one finger from each hand inside her and was working them in and out. She was beginning to become aroused. It was unlike anything she had felt before. Soon, she felt a third, then a fourth finger in her ass. Each time the girl moved her fingers out, she stretched open her ass a little further.

After doing this for awhile, the girl pulled her fingers out. Angela found herself disappointed, but soon felt a plug being pushed inside her. The girl started rubbing her clit again and it did not take her long to reach a climax. As her pussy exploded, sending juice gushing out, she realized that Joseph had returned.

She saw him walk over to a table and pick up a long slender stick. He walked up next to her and she suddenly felt a sting across her upper thighs.

“OOWW!”

He hit her again.

“Count!” He hit her again.

“One Master.”

Another blow was landed.

“Two Master.”

It felt like the butt plug was going to slip out at one point and Angela quickly tightened her muscles to keep it in. This caused the blows to hurt even more. She counted off the rest of the strokes.

Chapter 3

Suddenly, she felt something very cold being poured over her ass. It stung like hell when it hit her rim.

“Just a little alcohol to sterilize the area.”

She heard the machine start up again and then felt the sting of the needle on her cheek. She squirmed in pain.

“You must remain still or the tattoo won’t come out right and your Master will be very displeased with you. Concentrate on something pleasurable.”

He started up again and she did her best to stay still. Angela was not sure how long he worked on her, but finally he stopped, saying the tattoo was done. The girl came back in the room. She gently used alcohol on Angela’s ass, apologizing for the stinging. Then she rubbed in some sort of cream, which seemed to make it feel better. She instructed Angela to turn over.

“Did you bring the red box with you?”

“Yes. It is in my purse.”

“Your Master has purchased some beautiful jewelry for you. He loves piercings as well as tattoos; loves the way they look and feel during sex especially. And they can provide just the right amount of pain to enhance your pleasure. I have a number of piercings and I just live them. You do wish to be beautiful for your Master and allow him to provide this pleasure for you, don’t you?”

“Yes. I would do anything to please my Master and make myself more beautiful to him.”

The girl walked over and dug through the purse until she located the box, then came over with a small tray which she set down next to Angela. She opened up a small packet and used it to wipe off one of Angela’s nipples. She grabbed the nipple with some sort of clamp, then pierced it. After removing the clamp, she dabbed at the nipple and squeezed it to stop the blood flow.

She opened up the box and pulled out something that looked like some sort of an earring. The girl took it and worked it through the hole she had just pierced. Angela knew what was coming when the girl started to repeat the process with her other nipple. She gave her a box of wipes and a jar of the cream. She was to use the wipes on the nipples several times a day to prevent any infection. She was to move the rings around whenever she could to prevent the skin from healing around the wire. The cream was to be used on the tattoo. If either the nipples or the tattoo started looking red or swollen or got more painful, or if there was any discharge, she was to see a doctor right away.

The butt plug was to stay in the rest of the day as she had been instructed. The girl also gave her a small jar of the lubricant she had used in Angela’s ass. She suggested using her own fingers to stretch her hole open before inserting the plug next time. Angela had almost forgotten about the plug. She could hardly tell it was there. That is, until she sat up. The plug inside her was definitely larger than the one she had used on herself the day before. She felt a lot of pressure if she sat directly on it. If she leaned to the cheek where she had gotten the tattoo, that hurt, so she was only able to lean to her left.

Chapter 4

Angela gingerly got dressed. She took the bag with the items the girl had given her and walked out of the room. Joseph was nowhere in sight, but the girl was at the counter. She handed Angela an envelope with Michael’s name on it. She was not to open it but to give it to Michael tomorrow at work. Angela put the envelope in her purse and went to her car. She slid in gingerly and started up the car. She drove to the lingerie store and introduced herself. Immediately, another salesperson came over and introduced herself as Helen. She had talked to Michael and was expecting her. She would personally be helping Angela pick out her purchases. Helen took Angela to a private room and told her to strip.

Angela was thinking how she had been naked in front of more strangers today than she had been in the last several years. She had always been a little shy about her body and usually had the lights out when she was fucking a guy. At any rate, she stripped down and looked in the mirror. As she looked at her buttocks and thighs, she could see the red stripes from the caning. She got her first look at the tattoo. It was a view of a naked girl with her hands bound behind her back and sitting back on her heels. Her head was looking up and she appeared to be saying something as her mouth was open. She also suddenly realized that the butt plug could clearly be seen.

She was trying to hide the plug with her hands and had it halfway out, just as Helen walked back into the room.

“Now. Angela, you were told keep that plug in the rest of the day. You were about to remove it. You have disobeyed and I’m afraid I am going to have to call Michael and tell him. Bend over so I can reinsert it, then you will remain bent over. The plug had better not come out while I am gone.”

Angela bent over and the plug popped out the remainder of the way. Helen caught it and shoved it back inside her ass, pushing and twisting it down. Then she left to call Michael. Another girl came in and sat down without saying a word, just watching Angela bent over with her ass sticking out, clearly displaying the base of the plug stuck inside her. After several minutes, Helen returned.

“I’m afraid Michael is VERY displeased. He was willing to overlook your previous lapse because of the explanation you provided. He even provided the assistance you needed to fulfill his order. But, here you are again. You have disobeyed another order. He wants you to know that if he sends you somewhere, it is as if he were here himself. Any orders given should be treated as if they came directly from him. And you are to respond just as if he were here. As I am a female, you may address me as Mistress.”

“Yes Mistress.”

“Now, since you disobeyed, you are to be reprimanded. You will receive another dozen strokes which you will count out. Stand over here by this chair and bend over until the top of your head is touching the seat. Keep your legs close together and straight. If you cry out at all, I am to add another six strokes, and if the butt plug comes out, another dozen.”

Angela saw Helen pick up a cat-o-nine tails. She pulled her arm back and laid a stroke across her buttocks.

“One Mistress.”

The next stroke was across the backs of her thighs and felt harder than the first one.

“Two Mistress.”

The next stroke was right across the backs of her knees.

“Three Mistress.”

She counted out the remaining strokes which were applied only to her upper legs. Helen told her to stand up so they could get on with her purchases. Helen proceeded to measure her bust size, around her chest and the cup size as well. She measured her hips and waist, then her inseam. She wrote all the measurements down, then told Angela to wait while she picked out the items. Angela took the opportunity to look in the mirror again. Her legs were covered with bright red streaks and the buttock with the tattoo was red and swollen from the process. She rubbed herself and found she was quite tender. She was wondering how she would be able to sit down for the next few days. Another girl came in the room.

“I’m Cynthia and am here to help you feel better. Please bend over again and spread your legs to shoulder width.”

Cynthia pulled out a jar of cream and proceeded to spread it all over Angela’s cheeks and legs. It was the same cream the girl at the tattoo parlor had used and must contain some sort of anesthetic as it was helping to ease the pain, just as before. Then she started to play with the butt plug. She pulled it out a bit and Angela felt her squirt something inside her. She began to twist the plug around and move it in and out.

Each time she pushed it back in, it seemed like she was pushing it harder and further than the time before. She felt a finger reach around and find her clit. Cynthia rubbed her clit and fucked her ass with the plug. In less than two minutes, Angela had an intense orgasm and it was beginning to seem to her that Michael was right, her pleasure was being enhanced by the pain.

Cynthia did not stop, but changed her pace until Angela was breathing normally again. Then she started the whole process over and about five minutes later, Angela had a second orgasm. This time, Cynthia stopped and rubbed more cream on Angela. When she was done, she left the room without saying a word.

After a minute or so, Helen returned with an armload of items. First, she helped her put on a garter belt. Then she took one of the pairs of nylons. She told Angela to sit in the chair and helped her put on the stockings. She told Angela to stand up while she attached the garters. Helen mumbled that she did not like the way it looked and removed the garter belt. She selected another one and put it on, then hooked everything up.

“Much better.”

She took that belt off and tried on two more. She didn’t like the second one, but was pleased with the third one. She took the two she liked and selected an additional one in each style, but in a different color and set them aside. She removed the nylons, then held up a number of pairs to Angela’s legs. After selecting a half dozen pairs in various shades and styles, Helen added those to the pile of garter belts. Next came the bras. Helen helped her put on the first one. She squeezed and shifted Angela’s boobs, then finally took off the bra and threw it on a chair. She did the same with a second one.

On the third one, she finally seemed satisfied that everything was in the right place. Angela had to admit it was the best fitting bra she had ever worn. Then Helen reached into the bra and pushed her nipple rings through some slits that Angela had not noticed. Angela felt tingle of arousal when Helen pulled on the rings. Helen removed the bra and went through the process with several more bras. She asked her what color she wanted for the third bra. Angela selected a pale blue. Helen took the three bras and the remaining purchases out front.

Cynthia returned to the room with a slip she told Angela to try on. It fit like a glove and Angela noticed it had a built in bra. She removed it and Cynthia took it, along with all the discarded items, out of the room. She told Angela to get dressed. She also pointed out a small sink and washcloth where she could wash the cum from her legs. Angela did as she was told, then walked to the front of the store.

For the first time, she noticed the store had a number of other customers going in and out. She wondered if anyone out here had heard what had happened in the back and was suddenly very embarrassed. Helen handed her the bag containing her purchases and told her how much she enjoyed servicing her. She also handed her a sealed envelope with Michael’s name on the front and told her to give it to him at work tomorrow.

Chapter 5

Angela was even tenderer when she got back into her car. Now both cheeks were very sore, as were the backs of her legs. She could not find a comfortable position, so just resigned herself to the pain and went to the next stop. When she got to the department store, she went to the women’s section and asked for Amy as instructed.

Angela was determined that she would do nothing here that would require a call to Michael and cause the need for additional discipline. The butt plug had been in for quite some time and was beginning to get uncomfortable, but she had been told to keep it in until she returned home. She had been out longer than she thought she would be, mainly due to her disobedience and subsequent reprimands.

After a minute, a woman came up and introduced herself as Amy. She said she had been expecting Angela and had been given some ideas on what Michael was looking for. While she had been waiting, she took the opportunity to select a number of items. She would just need to take her measurements to be sure she brought in the correct sizes. She took her to another private dressing room and told her to remove her pants and blouse. She could leave her bra on.

Angela breathed a small sigh of relief. She removed her outer clothes as Amy watched. Then she took a number of measurements which she wrote down. She left to get the clothes. Angela sat down in a large cushy chair which did not aggravate her sore ass too much. Another girl came in with a plate of pastries and a pot of tea. She asked if Angela would rather have coffee, but Angela said the tea would be fine. The girl poured a cup and offered Angela her choice of sugar, lemon and cream. She selected a little sugar, which the girl added, leaving the room when she was done.

Soft music was playing and Angela closed her eyes. She opened them when she heard Amy return. She had a number of items and the other girl followed her in with an armful of additional items. Everything was hung on a rack. Angela proceeded to try on the various items, dresses, skirts and blouses. After holding up a few of the items, Amy dismissed them without even having Angela try them on. Others she fussed with a bit, setting some aside to revisit and tossing others at the helper. The other girl made occasional comments and placed the discarded clothing back on hangers. After going through all of the items, Amy went back to the pile of ‘maybe’ items. She had Angela put them back on and a seamstress came in. She made some adjustments and marks with pins, then left, taking the items with her.

Amy said they were done. Michael would be informed of the selections and would make a final decision. Any necessary alterations would be made and the final purchases would be delivered before the end of the week. She thanked Angela for her business and said she hoped to see her soon. Angela was just glad to be done and headed home. On her way home, she decided to pick up a pizza and some beer for dinner for Dawn and her, spending most of the money she had left.

When she arrived, she told Dawn about the pizza. Angela said she felt it was about time she provided the dinner for a change. She had left all the packages in her trunk, since she was not sure how she would explain them to Dawn. She could get them in the morning when Dawn went to work. She had also not said much about what she had done all day. As far as Dawn knew, she had spent most of the day at home, while Dawn was at work and had just left to get the pizza and beer.

As soon as she set the pizza down, Angela went into her room to remove the butt plug. It hurt as she pulled it out, but she noticed there was hardly any stinging. She decided she would soak in a hot tub for awhile after dinner and put on some of the cream. She looked in the mirror and saw the redness had faded quite a bit. There were still welts from the caning, but they had also gone down a lot. She put on a loose pair of lounge pants and went back to the kitchen.

Dawn had gotten out some paper plates and opened the beers. She had made a couple of small salads to go along with the pizza, so they sat down at the kitchen table and enjoyed their meal. Angela said things were looking up at the new job and she felt she would do well. She was almost beginning to understand why Michael was doing these things for her and no longer wanted it to stop.

To be continued...