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This is the second chapter in a series and a backstory to the Lacey-Steele series. It focuses on a sissy, if that doesn't interest you then please do not read this one.
Around 9 AM the next day:

‘Good morning bitch. You are going to write out a schedule of your normal daily activities. Work, school, etc. I want the time you wake up, the time you leave and the time you get home from school, work or other normally scheduled activities, and the time you go to bed; for each day of the week. I expect that your schedule may change from week to week, that is okay. You will send me a new schedule each time it changes. You have 24 hours to complete this task. You may ask questions for clarification, otherwise you will acknowledge this message and I will not hear from you again until the task is complete.” [Steele]

Sometime around 11AM:

‘Yes, sir. I’m sorry, I was at work. I will do this ASAP!” [Scarlette]

Scarlette had school that afternoon and rushed home to complete the task. She wrote her schedule for the rest of the week through Friday, and sent the picture at around 4:30 PM with an explanation that the school schedule is set for a while, but she gets a new work schedule on Thursdays and works in the morning usually. Other than work she is usually free on the weekends.

At about 7 PM:

‘Your writing is horrible; you need to work on it. I expect a new schedule from you each Thursday night. Is that understood?” [Steele]

‘Yes, sir.” [Scarlette]

‘It looks like you are free the rest of the night. We are going to talk, first about chastity.” [Steele]

‘Yes, sir.’ [Scarlette]

‘When last we spoke, it was the right size and you could wear it for up to 4 hours; is this still the case? [Steele]

‘Yes, sir.’ [Scarlette]

‘Good, you are going to wear it every day from now on for no less than 3 hours; eventually you will wear it 24/7. If it begins to hurt you (actual damage), or you need a new size, or there is any other reason you must remove the device; you are to tell me immediately.’ [Steele]

‘Yes, sir. I will.’ [Scarlette]

‘The first time we spoke on the subject, I sent you links to articles and other resources to learn about the devices and how to care for them. I sent 10 links. Each Friday for the next ten weeks, you will send me a report of what you learned and how you used the information; one for each link. Taking care of the chastity and following the schedule I give you are your responsibility, not mine. Any questions so far?’ [Steele]

‘No, sir.’ [Scarlette]

This was beginning to feel more like a chore than anything.

‘How many pairs of women’s underwear do you own?’ [Steele]

‘Just the one, sir.’ [Scarlette]

Steele sent links for websites on what underwear might work for Scarlette.

‘Research so that you can buy, do not worry about the ‘buying’ part for now. What about makeup?’ [Scarlette]

‘I have some, not a lot. I used a lot practicing for the hotel.’ [Scarlette]

‘I will be scheduling your times to work on makeup, your voice, and sucking a dildo. Everything you are scheduled to do; you will complete and send me photos or videos to prove it. Is any of this unclear?’ [Steele]

This sounded like a lot to do, in addition to school and work.

‘I’m not sure that I can do all of this…’ [Scarlette]

The next photos that Scarlette received were a picture of her apartment number on her front door and a picture of the door mat in front of the door, the one that she looked at and stomped on every day. Scarlette felt her butthole tighten and her heart starting to race.

‘I’m not asking, bitch. These are the things that you are going to do.’ [Steele]

‘I’m sorry, sir. I’m a worthless fuck pig and I’m lucky to be in your service.’ [Scarlette]

‘That’s a good sissy bitch. If you aren’t already wearing your chastity, put it on and show me.’ [Steele]

Scarlette sent the picture, knowing that she was likely going to be scolded.

‘Wrong, bitch. You are to keep your body shaved and smooth. What the fuck is this? Tomorrow, you will do better. You will wear the chastity for the rest of the night tonight, remove it when you are going to bed tonight around 10. Don’t even think about playing with yourself, those days are behind you. Research underwear. Goodnight fuck doll.’ [Steele]

‘Goodnight sir.’ [Scarlette]

Scarlette was afraid, and excited. She had been put in her place and was now to live by a schedule designed by someone else. It was intoxicating. The chastity beginning to remind her of the commitment she made. It was hard not removing it; it was even worse when she did remove it to go to sleep knowing that a line had been drawn and not wanting to cross it. She had already been told by Steele that she was not allowed to play with herself, this time the feeling was compounded.

Scarlette worked almost every morning Monday – Thursday typically, and sometimes on Fridays or Saturdays. She went to a community college and had school until 3 PM Mondays, Wednesdays, and Fridays; and until 6 PM on Tuesdays and Thursdays with a 3-hour gap between work and school.

It was now Tuesday morning approaching the end of Scarlette’s shift when she felt her phone buzz. When she was off, she read the message.

‘When you get the package, request permission to open it.’ [Steele]

‘Yes, sir.’ [Scarlette]

What package? And what is in it? Scarlette was thinking all the way home. When she did get home, she saw a box which was wrapped in plain brown paper. The only writing on the paper was her address.

She carried the package inside, and placed it on the counter, it was heavy.

‘I received the package; may I open it?’ [Scarlette]

‘No, bitch. Message me when you get home from school for another chance. You should take this time to shave so that you are ready to put on your chastity immediately when you do get home. You will send me a picture of the chastity when you are ready to ask again.’ [Steele]

‘Yes, sir.’ [Scarlette]

Whatever was in the package, the underlying message that Scarlette was giving up control was working. She kept imagining what could possibly be in it. She thought about opening it anyways, but decided against it.

Around 7 pm Scarlette sent the picture of her chastity with a message asking if she could please open the package. She needed to send another picture; this one was to be the package with a clock in the background – relief that she decided correctly not to open it settled in.

Once she had permission to open the package, she ripped the brown paper off the outside. The box itself had writing all over it, things like ‘Scarlette is a sissy bitch’ ‘… a fuck hole’, ‘a cum dumpster’, etc. Scarlette imagined the embarrassment she would have experienced if the paper weren’t there and her neighbors saw the writing.

She opened the box. There were two boxes inside stacked on top of each other, they must have had a full reem of paper each. One was a blank weekly schedule template, the other was a template for a written report. Each had a watermark picture in the background – two pictures of Scarlette from the hotel. The schedule had a picture of her smiling with cum on her face. The report had a picture of her kneeling with the blindfold and gag, her arms bound behind her.

This was intense.

‘Re-write your schedule on your new template with the following additions, and send it to me.’ [Steele]

A list of times indicating when to wear chastity, when to practice make up, when to practice speaking, and when to suck on a dildo were in the message. Tonight, in addition to the chastity, she was to look up pictures of makeup styles and try to find videos of how to apply them, then to send all of the links to Steele.

Scarlette sent a picture of her new schedule. Remembering how she felt when the photo in the background was taken.

‘The next time you send me sloppy writing, I am going to make you redo it. If you need time to study, you had better write it into the schedule before you send it to me. I will send you a list of tasks and times, and you will add all of it to the schedule, then send me an updated picture. Do you understand?” [Steele]

‘Yes, sir.’ [Scarlette]

‘Good bitch. If something comes up; you want to hang out with friends, you want to go watch a movie, anything like that – you will ask my permission. Is that understood?’ [Steele]

‘Yes, sir.’ [Scarlette]

Scarlette, who had not gratified herself since before she met the couple at the hotel, was extremely horny at this point. She had been called a bitch and then put in her place over and over. The chastity felt like it was squeezing her sissy clit. Even the fact that she was about to ask permission to do something she used to have the freedom to do on her own was itself a turn on.

‘Sir, may I please cum?’ [Scarlette]

‘Tonight, you may use a dildo while in your chastity, after you finish tonight’s assignment. You may also try to rub your clit like a woman with the chastity on. Those are your only options. So, it will really be up to you whether you can or not. Let me know how it goes, you sissy fuck.’ [Steele]

Scarlette finished the assignment and immediately lubed her anal dildo, trying to stimulate herself enough. She rubbed her chastity like a lady but it was useless and she began crying out of frustration. She was constantly thinking about using a vibrator, or removing the chastity – she decided that it wouldn’t end well for her.

‘I can’t cum, sir.’ [Scarlette]

‘Would you like to use a vibrator?’ [Steele]

‘Yes sir, please!’ [Scarlette]

‘I don’t know, you talked back to me yesterday…’ [Steele]

‘I’m sorry sir, it won’t happen again. Please let your stupid sissy bitch cum.’ [Scarlette]

‘I want you to write ‘I’m a sissy fuck’ on your thigh with a marker and you will ruin the orgasm. That’s the best you are going to get, it is more than I will offer in the future. If you accept, do it and send video proving that it was ruined. If you do not accept, you will never ask again.’

About 15 minutes later a video came, Scarlette could be heard sobbing throughout.

‘Good sissy.’ [Steele]

‘Thank you, sir.’ [Scarlette]

She really did feel like a sissy bitch, a piece of property. ‘Intense’ was still the word she used to describe it in her mind.

The next few days Scarlette was becoming used to living by the schedule and complying by sending photos and videos. Friday night she had to re-write her report three times before Steele finally accepted it. She had to make her writing look like a woman had written it.

Sunday morning rolled around; it was now 10 AM. Scarlette planned to study throughout the day, she had submitted her schedule with Sunday free and Steele had not given her assignments, so she thought it was a day of reprieve.

There was a knock at the door, when she answered the door, she was terrified. It was Steele and Lacey.

Steele ordered Scarlette to kneel with her face angled toward the floor, then he began walking around the apartment, like he was looking to rent it – inspecting it. Lacey was standing next to Scarlette the whole time this was happening, a firm grip on Scarlette’s hair.

Steele sat on the couch and ordered Scarlette to crawl over, she was to show him how to use her TV, then kneel in front of him. Kneeling now, she heard Steele speak.

Steele: “Do you typically have Sundays off?”

Scarlette: “Yes, sir.”

Steele: “Good. Go get ready for us. I don’t care how long you take: chastity, smooth, makeup, hair, female underwear and the dress from last time. When you are ready, you will kneel back here and wait. Now bitch.”

Scarlette: “Yes, sir.”

Scarlette was beginning to feel overwhelmed. She was trying to take her time making herself pretty for the couple but found herself shaking. The nerves were getting to her. She never had visitors over; let alone anyone coming over and taking control.

When she was ready over an hour later, she knelt in front of the couple who let her stay there for what felt like an eternity.

Eventually, Lacey pulled a strap on dildo and a ball gag out of her bag and ordered Scarlette to clean them and bring them back on a clean towel. Scarlette did so, then returned to kneeling.

Once Scarlette was kneeling again, Lacey took off her pants and shirt, revealing lingerie. She fitted the strap-on dildo, and lubed it. Then she ordered Scarlette to get into a ‘table’ position; her torso parallel to the floor, she was supporting herself with her knees and her arms; forearm and palms flat on her carpet.

She was told to crawl to Steele and assume this position in front of him, her face between his thighs.

As soon as Scarlette was in the position, she felt Lacey’s dildo penetrating her butthole; she was thankful that Lacey took it slow before inserting completely.

Lacey grabbed Scarlette’s hair, pulling her head back and up, her open mouth now in front of Steele’s crotch. Lacey was beginning to thrust in and out of Scarlette when Steele spoke.

Steele: “You didn’t believe me, did you. Tell me, do you feel like our bitch?”

Scarlette: “Yes, sir.”

Steele: “Don’t just tell me, tell Lacey. Thank her for fucking you, you pathetic sissy fuck.”

Scarlette: “I’m your bitch Mistress, thank you for fucking my pathetic sissy ass!”

Lacey spanked Scarlette hard.

Scarlette was now moaning and whimpering.

Steele: “Isn’t this so much easier? Being told what to do. Having your choices made for you. You need it, don’t you?”

Scarlette: “Yes, sir.”

Scarlette’s face was now resting on Steel’s left thigh, moving back and forth with each thrust. Her makeup and drool beginning to smear on his jeans – he didn’t seem to mind. Scarlette had to adjust her arms when her hair was pulled back; they were becoming tired from supporting her weight. Steele’s hand moved on top of Scarlette’s face, resting there.

Steele: “This apartment, it is my apartment. The car out there, it’s my car. I am allowing you to use them. Say it.”

Scarlette: “This is your apartment and that is your car. You are letting me use them and I am appreciative, sir.”

Steele smiled hearing the last part.

Steele: “We will be here every Sunday and you will be our pleasant little hostess, won’t you?”

Scarlette: “Yes sir, it is a pleasure.”

Scarlette was becoming more and more turned on - she couldn’t believe the way that being fucked in the ass was stimulating her.

Lacey pulled out and told Scarlette to clean the dildo then put it back on the towel. Once she was done, she was to clean and insert her butt plug, then return to kneeling. Scarlette did as she was told.

Steele ordered Lacey to ‘demonstrate, inspection, wall’. Lacey stood and walked to a clear wall by the front door. She placed her forearms on the wall and stood with her ass out, legs spread.

Steele: “Scarlette, take her place.”

Scarlette stood and walked to the wall, Lacey moved and helped Scarlette into the position.

Scarlette began to feel hands and fingers, running up her smooth legs, finding their way to her ass, spanking it multiple times. The butt plug being played with, running shivers up her spine.

Steele: “You are a piece of fuck meat. That is all you are. Say it.”

Scarlette: “I’m just a piece of fuck meat, sir.” She really felt that this was a true statement.

Steele: “We will write a time on your schedule that we will arrive on Sunday, typically 10 AM. We expect you to be completely ready for us. We will knock on the door; you will look through the peep hole and verify that it is us. You will unlock the door and crack it open, then immediately come to this position and you will wait here until we say otherwise. Is all of this understood?”

Scarlette: “Yes, sir.”

Steele: “You have not been taking good care of my apartment, have you?”

Scarlette: “No, sir.” Imagining Steele looking at the clutter and the mess.

Steele: “Are you ashamed?”

Scarlette: “Yes, sir.” She really was.

Steele: “That is ok. You will be cleaning it, but not today. Today you need to learn a few things.”

Steele ordered Scarlette to kneel again, this time lifting her hair and holding it up, ‘collar’ was the name of the position. He fitted a collar around her neck and attached it to a leash.

Steele: “You don’t get to speak unless given permission, for now, you have no need.”

Before Scarlette could respond, the ball gag was in her mouth muffling her.

Steele and Lacey took turns walking Scarlette all over the apartment, she was to kneel each time they stopped walking. They took her to each room and started pointing out all of the ways that it didn’t meet their standards, throwing things around from time to time adding to the mess.

Eventually, Scarlette was ordered to pour water in a bowl and put it on the ground near the couch. This was her drinking water. Once the bowl of water was on the ground, Steele removed the leash and gag. He told Scarlette that she could move freely throughout the apartment, but she was to crawl, never stand, she was to take her time crawling.

Steele was taking more pictures as Scarlette made her way around, drinking from the bowl, crawling.

Eventually Scarlette became tired and layed down on the ground at the couple’s feet. She was there for a few minutes when she was forced to stand, being yanked up by her hair. She was escorted to her bed, being spanked hard along the way.

Steele removed his clothes, took one of Scarlette’s pillows and sat on it near the head of the bed. Scarlette was to crawl over and give him a sloppy blowjob. Her drool and his precum rolling down Steele’s shaft and balls, beginning to pool on the pillow. Steele’s hand forcing Scarlette’s head down over and over again.

Lacey removed Scarlette’s butt plug and began fucking her with the strap-on again. Scarlette was still wearing the panties which were stretched and pulled to the side to provide access.

Eventually, Steele pulled Scarlette’s head up and slapped her. Lacey pulled out and Scarlette was forced to turn over, laying her head on the pillow Steele had been sitting on. Steele reinserted his cock into her mouth forcing her to choke over and over again until he finally came on her face, his load spraying on her hair and her pillow.

Steele and Lacey stood up and began walking away. Steele turned and spoke.

“That is enough for today. You will clean yourself and come back to the couch to rest before we leave. You may wash your sheets, but not your pillowcases; that pillow is the pillow you sleep on this week. Come out when you are ready.”

Scarlette laid on the bed feeling completely used, she had absolutely no control over anything at this point. It was incredible.

Scarlette washed her face, then went out to the couch. She was allowed to lay on the couch with her head in Lacey’s lap. Lacey was stroking her hair like a pet. Scarlette liked it.

After a while, the couple told Scarlette to hydrate and eat something. They were on their way out when Scarlette asked if she could cum. Steele told her the same as the night before: use a dildo with your chastity and rub like a lady – if she did, she was to send pictures. A vibrator was no longer an option for Scarlette. The couple left as soon as they had come over.

Scarlette was relieved that the couple had gone, the collar still around her neck. She tried and tried but was not able to cum.

Frustration and shame became the main feelings overwhelming Scarlette when she decided to study, and when she went to bed, smelling Steele on the pillow.
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