If You Dare Ch. 01

Snapping out of that sexual daydream, she walked on to the anal plugs. To her amazement, there were too many. How could she choose? There were different colors, shapes and sizes, some ribbed and some with nubbs. Some looked like hard cocks, and some were very realistic, and large. It became obvious to her she would have to ask for help in her selection.

She looked for a clerk, but all she could see was an unshaven man behind the counter. He looked rather lurid, but he was the only one in the store. He was reading something, and didn't seem concerned with what was going on in the store. She walked up to the counter. He looked even worse, when she got closer. But, she needed help, and he was her only choice. "Can you help me, please? I need some assistance in making a choice."

The man didn't seem interested in helping. He almost looked disturbed that she was asking for help. Without even looking up, he responded "What are you looking for?"

Gloria leaned closer to him, because she didn't want to say aloud what she wanted. She put her hand up to her mouth to shield her voice from traveling all over the store. "I need to purchase an anal plug and harness. Could you help me with finding the proper size?"

The man raised his head and looked at Gloria. The way he looked at her, she felt sure he was going to say something mean. She was starting to understand what it's like to be a submissive and purchase her own training devices. It was a humiliating feeling, for her. This man was not making it any easier for her.

Pointing to the area Gloria had just been to, the man answered "They are over there. There are several to pick from."

"Yes, that is the problem. There are so many, I can't decide. I have no idea what is considered medium. Would it be possible for you to show me which ones are medium in size?"

"You want a medium?" He walked over to the anal section and Gloria followed behind. "There are several different types." Pointing to one that looked like a cock with veins, and one that was ribbed, he asked in a monotone voice "You want one like this, or maybe like this?"

"Those are mediums?"

"Mediums? Well, that depends. Is this for you?"

Gloria turned several shades of red before she could answer that question. "Yes."

Stepping back, the man seemed to be sizing her up. "Turn around."

Her face now flushed and surely a deep red, she slowly turned. She knew he must be checking her bottom for size. How humiliating it felt.

The clerk picked up an evil looking black plug, and held it up as if he was showing a diamond ring. A smile formed on his face and he looked Gloria right in the eye. "This is a medium. Will there be anything else?"

Gloria swallowed and licked her dry lips. "Yes, I need a harness and some lubrication."

"A harness? What kind of harness?"

"I don't know the name of it." Again, she blushed. "Something to keep it in."

"Like a chastity belt, then?"

"Chastity? Oh yes, that's it. A chastity belt."

"A plug, a chastity belt and some lubrication. Is this all?"

"Can you tell me how to fit it into the belt?"

He demonstrated as he talked. "It's very easy. The base slides into this slot, here. Anything else?"

"No, that's all."

Turning toward the counter, the man carried the plug and the chastity belt. "The lube's up at the counter."

Gloria felt more at ease with her ordeal nearly over. She followed him back to the counter.

"What size do you want?" He asked, while pointing to the lube display. "There's small, large, economy and party. The party size is a big seller."

Looking everything over, Gloria couldn't believe all of the decisions to make. Again, her face was surely bright red. Looking at the prices, the party size was a good deal. If she got that one, she wouldn't have to go through this agony for a while. But, she just couldn't get the words 'party size' to come out of her mouth. She saw the smirk on the man's face. He might think she was planning a butt fucking party if she got that size. "Oh, I think the large should be fine."

His look changed. "No party size today?" He asked. "It's a good deal."

"No, not today, thanks" she replied.

She paid for her purchases and was on her way. With one last look at the clerk, she could tell he probably knew what was going on. At least he had a good idea. This was one purchase she would remember.

She got home, and poured the bag's contents out on the bed. She picked up the butt plug and looked at it. It seemed terribly big for a medium, but that was what the clerk had said it was. She picked up the harness and slid the two together. It looked even bigger. It was also bulky. She would have to wear a loose fitting dress to cover it up. She also noticed another slot in front of the belt. She figured it was something she would find out more about, later.

The next thing to do was to see how this was going to feel. She had to know if she could wear it a whole day, as he had commanded. She stripped and read the instructions on the lubrication tube. She did as it said, lubing the plug and also her bottom. She stepped into the belt, and aimed the pointed end of the plug at the small lubricated entrance of her ass. Slowly, she inched it up, tighter and tighter. She grunted as it made its way up her ass.

The plug was tapered, shaped like a cone, with a smaller section just before the flange of the belt. Slowly, she let it slide up her ass until it finally popped into place. A snug fit, and not too painful. The clerk must have been correct about the size. It was a tight fit, but not unbearable. Gloria buckled the belt, and put on her clothes. She walked around the apartment, doing normal daily things.

She noticed how it felt to experience this, when she bent over and when she sat down. The plug would push deep into her, in these positions. She thought it would be a near disaster for her, because her job included mostly sitting at a desk. She wondered how it would feel when one of the execs called her in his office for dictation. She would have to sit there as he dictated a letter or memo. She would have to sit there, with the butt plug snuggly poking into her ass. How could she sit there and think about her job? How could she sit there and not think about her filled bottom? But, she would have to.

The next day, she got up early. She had to decide on what to wear. She had to wear something that was not too tight, even when she was bending over. There was no way she could let her co-workers know about the anal butt plug, so she had to take any precaution necessary to conceal it. It would not be easy.

She picked a dress with ruffles, and pleats below the waist. It fluffed out enough to conceal any shapes of her body or the harness. It looked a little like a catholic school uniform. She had to insert the plug before getting dressed. Because it was the second time for this, she felt she was better prepared. She held the plug in her hand, and lubricated it liberally. Then she bent over and lubricated her ass. Stepping into the harness, she sat in a chair to slowly inch it into her ass. With a slight whimper, it popped into place, and she buckled the belt. Next, she got dressed and was off to work.

Walking to her car, she felt the straps of the harness constricting her movements. Slowly she sat in the car seat, letting out a small gasp as the plug hit home. A small victory, she then started the car and the drive to work. While sitting in the car seat, she noticed the plug wiggled inside her with every movement of her lower body. Even the slightest movement caused twinges of sexual feelings deep inside her. This would not be easy to deal with all day long.

From the time she left the apartment, she felt differently. Everything even looked different to her. The plug in her ass wasn't the reason for that, was it? Could it be the cause of her mood? Surely, there was another reason.

She arrived at work and rode up the elevator with several co-workers. Not yet accustomed to the harness, she had trouble keeping up with her friends. She had to tell them she was tired from a sleepless night, because she couldn't tell them the truth. That was the first of her white lies to get through the day.

When Gloria got to her desk, her boss called her into his office. He needed to send a letter as quickly as possible. She got her pen and pad and went into his office. She slowly sat in the leather chair opposite him and wrote as he dictated. She kept squirming in the chair, because of the plug in her ass. Her boss asked her if she couldn't sit still. Of course, she couldn't tell him what the situation was. That leather chair was so terrible to sit in. It was soft and it conformed to her body. Because of this, the butt plug snaked its way up her ass into areas it hadn't before.

But, she managed to sit still for the rest of his dictation. On the way out of his office, she noticed she was waddling. The more she sat in that chair, the more the plug wiggled up her ass. And, on top of everything else, she was getting wet from all of this. She really hadn't expected that. The butt plug was forcing her to make excuses for her actions, so she wouldn't be found out. It was also forcing her to tell lies. She never told lies, before.

And, the fact that she was also enjoying this day was difficult for her to understand. All of this was making her think. She had no idea this little experiment would cause such a change in her daily life. Maybe it was the secrecy of it all. Maybe it was the butt plug in her ass. The only thing she knew for sure was she was enjoying it. Maybe her new email Master would explain it. After all, it was his command. Surely he had his reasons for this form of training.

The rest of her day was more of the same. She had to sit a lot, and because of that, the plug made itself known a lot. She noticed some chairs were worse than others were, forcing that plug deep into her. Those chairs made her fidget a lot and that drew attention from her co-workers. One friend even asked her if she had ants in her pants. If they had only known the truth.

When the workday was finally over, Gloria couldn't wait to get home and send him an email. She was proud of herself for lasting the whole day, although some strange things had happened. Now, they seemed humorous, but not at the time.

She sat at the computer, with the butt plug still tightly in her ass. He had wanted this. She mentioned that and her day with the strange sexual experiences, in the email. She asked him to explain why she felt the way she did, if possible. Then, she waited for his response. She waited for two days, until he finally sent a reply.

I am happy you completed this command so quickly. It shows you truly want to realize your submissive dreams. I like that. It shows how honest you are. I also consider myself honest. I will always tell you the truth, when you ask a question.

You asked me why I had you perform this command. I think you know some of the answer now, without my explaining. This experience put you in a place of submission, but it was compounded by the fact that you couldn't tell anyone about it. Only you and I knew you were wearing that plug and harness. Because of this, you experienced feelings of submission to me.

These feelings were new to you, but still feelings you have always wanted to experience. This alone should have been enough to overwhelm your mind. But, I had you take these feelings and compound them with your daily life where you have been many times before. This is a place where co-workers know you and your actions are also known. Because you are known, they saw the reactions you had from the plug in your ass as different or strange, and they asked you if you were feeling okay.

Normally, you would have no problem answering these questions, but because of our secret, you had to lie to save your situation from being found out. I am sure that is out of character for you, but you did it anyway. Sending the email with the plug still in your ass was a submissive act. The power of submission is something new to you, but you are beginning to understand.

Gloria read this message, starting to better understand what submission is. She wanted to please him, and it was satisfaction for her to do so. Not sexual satisfaction, but something deeper inside. Something she had felt a need for most of her life, but had been denied. She was now on her way to fulfilling her need, and she wouldn't be denied again.

She continued with the message he had sent her.

Because you have completed this command so quickly, I have something for you to enjoy. I want you to follow these instructions closely.

First, you will need a 3-inch insertable vibrator. Purchase one, if you don't already have one. Also, go to a store where they sell soft nylon rope and purchase about 20 feet of quarter inch thickness. Also purchase about six feet of rough jute rope, about one half inch thick.

Purchase a role of 2-inch construction grade Velcro strapping, with adhesive backing. You will also need a cigarette lighter of some sort and scissors. Once home, open the Velcro, and cut the two parts into equal strips. Cut two strips about 3 feet in length, and two at 6-foot. Then, remove the backing and adhere the parts together. This will allow you to use the strips as binding. Be sure you connect the two different types of Velcro together, so this can be accomplished. One part is soft to the touch and the other is rough.

Strip naked, and take the soft nylon rope and tie it around your waist. Don't tie it tightly, but snuggly. Make sure the knot is right in front below your belly button. Then, slide this knot around to the back, and take the long length and run it through the crack of your ass and between your legs. Be sure to run it between your pussy lips and over your exposed clit. Tie it there where it meets the rope at your waist. Be sure you tie a knot that can be untied later. This will be used again.

Make sure the section going through your legs is snug, but not too tight it cuts off circulation. Be sure you are allowed movement, but that movement will cause the rope to rub up and down though your crotch. Then cut the excess length off. Remove the rope, but remember how you put it on, for later. Use the lighter to melt the fresh cut edge of the rope so it won't unravel, later. Watch it, the hot nylon will burn!

After you have finished your crotch rope, I want you to wear it to work one day. It won't be quite the same as the butt plug experience, but it should be an interesting day. As always, email me back with what you have learned from your experience.

Gloria read the instructions with wide eyes. She didn't want to wait very long. Going straight to the store, she picked out the different lengths and type of rope. She got the quarter inch nylon, and the rough jute. She also found the 2-inch roll of Velcro he mentioned. Everything she needed was at her neighborhood hardware store.

Once home, she began tying the crotch rope together, as he had instructed. She cut the rope and melted the ends with the lighter. She cut the Velcro into the strips he wanted. Then, she put the two types together as instructed. She found she had made Velcro ties without even realizing it. Her face blushed when she thought what he would have her do with them. She tested a couple just to see how they worked.

It was very interesting to see how well these Velcro straps held her. It was also very interesting how easy it was to use them. There was no tying involved, and no escape, if she didn't make sure to keep one hand free. This Velcro was quite an invention. A smile formed on her face.

The next day, she had to go to work. But, to follow his command, she was to wear the crotch rope to work. As with the butt plug, she had to wear concealing clothing, so her co-workers wouldn't see the rope around her waist. She decided on a pleated dress. One she had purchased because it reminded her of her days as a cheerleader. She topped this off with a white blouse, and white panties. She checked out her wardrobe in the full-length mirror. She twisted and turned, making sure the rope around her waist didn't show. It didn't show, but all of her twisting sure got her attention. She could see this would be an interesting day.

Off to work, each little move sent tingles through her. The crotch rope caused her thoughts to wander, and she found it difficult to concentrate on work. She noticed she would forget about it while sitting still, only to be reminded of it, when she would stand, or twist to answer the phone. She usually hated it when the phone rang in her busy day, but this little addition to her clothing was making her wish that phone would ring.

During the day, she experienced sexual tingles from the rope. Like with the butt plug, she found normal daily tasks to become sexually charged. Walking down the hall was the first thing she noticed. Her breath quickened as she walked. Each step felt like someone was rubbing her clit. When talking to co-workers, her voice quivered. And taking notes in meetings was next to impossible. Each time she moved that rope rubbed against her clit, and she had to do her best to keep quiet. In the boardroom, that wasn't easy to do. When the day was finally over, her panties were sopping wet. It was a very unusual day.

Gloria couldn't wait to send that email. She was learning more and more about her submissive side and couldn't wait to learn more. She was impatient to find out what he had in store for her next lesson. But, when she received his next email, she had no idea what to expect. She sat at the computer and read, with wide-eyed interest, his commanding words.

Well, sweetie, you have done just as I have asked and in this process you have learned a lot. You have experienced many different things, too. It's time for us to advance to the next level of your training.

If you want to continue your training, you will begin to learn something other than the self-punishment I have had you experience up to now. But, to do this, you must now learn trust. If you want to continue, you must trust me with your home address. You will send me your address, have your door unlocked, and follow the following commands to the letter. I will come and inspect your work.

To prepare yourself, you will purchase a well-made pair of metal handcuffs. You will find a non movable object such as a pipe, bedpost, or table leg to use, and cuff your hands around it in such a way your bottom is elevated above your head. You will use the Velcro straps to bind your ankles together.

You will find a scarf or something similar to blindfold your eyes and you will be dressed only in white cotton panties. It will be up to you to decide the order necessary to accomplish everything. I will give you a time to be ready, and you will wait for me to arrive.

Gloria couldn't believe it. She was going to have to think about this. He was wanting her to allow him entrance to her apartment when she was bound and unable to see. She would also be unable to stop him from doing what he wanted with her. This would indeed take a great amount of trust.

Gloria had read stories of such things, where a submissive had trusted someone, only to be seriously hurt or even killed. She surely didn't want that to happen here. She didn't know this man from anything other than her online communications. He could be a terrible person, using her need for a submissive life against her. It would be easy to do, and she could become just a statistic. But, her inner self was talking to her. She didn't see him as a bad person, because of what he had shown her to this point. Although her better judgement was telling her to be very cautious, she felt she had to do as he said. This was blind trust, but trusting him was what she had to do. This was a large hurdle in her search to release the inner submissive.