Phone Sex

A special thanks to my volunteer editor BDSMBill. Thank You Sir for Your continued advice and encouragement in my writing. All rights reserved.

Anastasia was a person with a self-secluded personality. She did not let many get too close. Those that did get close, she gave her all. The rest got her façade of a personality, at least up until she met Weston.

She did not know this, but He had the most piercing eyes of grayish blue. When He gazed upon someone it was like He looked right through to their very soul. She also did not know He had an amazing ability to poke and prod His way through a person's shell and find the heat of the inner core.

Meeting Weston was quite by accident. Anastasia bought her first computer and ended up in a chat arena. It was quite crazy actually, fifty people in a room, all yammering away. Her thoughts were that it was a game. Not real. Just words on a screen. She began to meet people and would consider them "friends," but in a fantasy world how much was just that: fantasy.

Anastasia met a man in the room that she began to chat with privately. They would talk a lot and one day He kissed her. Now how in the world can one kiss online you might ask? Anastasia could answer you now, whereas a few weeks before she would have said bullshit. The guy named Jack kissed her and then some, and Anastasia found herself playing with her pussy while typing back and forth with this Jack.

She had an amazing orgasm that changed her entire perspective on what was fantasy and what was reality when it came to online. Anyone could ask her and she would say it was real. Why? She got off didn't she?

Jack, of course, was like men you meet face to face. He got the goods and He disappeared, sending Anastasia into self-protect mode once more. She was determined not to get close to anyone else.

Weston was a cruiser on the web. He just poked in every now and then, looking around and seeing what He could get into. One day He ran into Anastasia. He immediately felt a vibe from this woman. He didn't know her story but He was going to know it before all was said and done. His eyes took on a glint of determination.

Anastasia felt a warmth when Weston said "hello." He immediately took over the conversation, steering it into the direction He seemed to desire. Anastasia felt overwhelmed by this man. Why was that? She was so unsure, but there was just something about Weston that overpowered her senses and broke down any façade she could put up in a heartbeat.

Anastasia and Weston began meeting up in the chat room fairly regularly. He began asking her things about how she felt about certain topics -- her sexual experiences. She would evade the sexual topics, but He didn't allow it for long. He would type in, "I'm waiting." She would sit there looking at it and then for some reason would answer His question.

Why? At that time she could not tell. Her sexual experiences were slim to none. She had had basic sex -- nothing earth shattering. She didn't even get off most times. Weston took all of this in and then some.

Time began to pass. Weston and Anastasia grew closer and closer. The relationship was growing deeper by the day. Weston confided in Anastasia that He was a Dominant and asked her if she knew anything about Dominance and submission. Anastasia responded in repulsion, thinking He meant sadomasochism and other decadent things. Weston explained to her there were all kinds of facets of the lifestyle and He gave her an assignment, the first He had ever given her. He did it in such a way that Anastasia had no clue she was being controlled.

Weston told her to look up dominance and submission and to read everything she could over the next week. He then instructed that she write how it made her feel, what it made her think, how her body reacted, what she thought affected her the most, and what she found she desired out of the reading. Anastasia went about the task with vigor, as she craved knowledge of new ideas. She was surprised by the information she found.

She looked through many web sites, and began to read about submission mostly, finding herself opening up to this idea more and more as she related to the words stated. Anastasia realized she was submissive. She loved to please others. Even though she hid behind walls, she loved to make people happy. She read about girls that had Masters, girls that would do anything to hear the words "good girl."

Anastasia began feeling something deep in her heart and soul, a kindred spirit of some type with the girls in the words she read. Then she read about Domination, that it wasn't about being told what to do but more along the lines of living to please One that could Master her, to live by His rules but not forcefully, more like willingly.

The articles gave Anastasia a lot to think about. She had a lot of questions and began asking Weston about some of the things she had read. He would explain the best He could and point her in another direction to research her answers. This way it wasn't just Him saying it was so. She would read other perspectives on the matter.

Her report was due in two days, and she had not yet begun to write it. Anastasia thought, "Well, it will get done, but I guess it will be a little late." Anastasia began to write about herself first, how even as a little girl she had strived to please everyone in her life, that she craved praise and it would make her heart soar when she knew she had done well.

The day of the report came and Anastasia was not finished yet. It was almost done -- just a little longer. She was unaware that she should have just begged for more time, but after today she would know for sure not to be late again, at least not with Weston. Weston popped up on the messenger program they both had installed. Only the two of them were on each other's list, so they could have a lot of private time.

Weston said "hello," and asked how she was doing. Anastasia said she was great and had been working on her paper, it was almost done.

Weston sat there a minute -- long enough for her to say, "Are you still here?"

Weston typed in nods. He then asked her if she understood that the paper had a time limit and was due on a certain day and time. Anastasia said yes she did and she apologized profusely for the lateness. She was just trying to make it perfect.

Weston's next words made Anastasia's world sink. "Anastasia, I am very disappointed in your failure to complete the simple task I gave to you," He said.

Anastasia blinked back the tears that threatened to consume her and said once more, "I am so very sorry Weston. Please let me finish it and send it tonight. It will be done, I promise you."

"I will give you until 9pm tonight. If it is not done, Anastasia, trust me. You will not like the consequences," He stated.

Anastasia went back and immediately began work on the article, pulling all the pieces together, reading it and editing it over and over again, making sure it was presentable, that it was pleasing to the eyes, and most of all, making sure it wasn't just words and that it showed her heart and soul.

At 8:55pm, true to His word, Weston logged back on. "Are you finished, Anastasia?" he asked.

"Yes, I am finished, and I am emailing You the article now," she replied breathlessly.

She sent the document and waited. It seemed like an eternity that she waited. Her stomach had butterflies swimming. Amazingly, for some reason, even her shaved pussy was reacting to the wait. She felt the wetness as it slid between the petals, blushing profusely, so glad He was not there to see this. Finally, after what seemed like forever, Weston private messaged her.

"Very well written, Ana. I am well pleased with your honesty. I feel your passion. I can see the excitement in your writing. I am still displeased at the assignment being late though. What do you think should be done about it?" He said.

Anastasia was stammering in real life trying to think of the appropriate response. It hit her then that she had already begun the journey of subbing to Weston. Her next words hit her in the gut as she was shocked that it came out as it did.

"I was late, Weston, and I apologize. I know an apology is not good enough. From what I have read and written, my answer is that You should punish the infraction. In that I will learn not to be late with You or anyone else again," She typed out.

Weston stared at her words on the screen, and His smile would have melted her to the very core if she had been able to see it up close. "Yes, you are right Ana. You should be punished and you shall be. The how of it is the tricky part. You are very new to this and I realize you have no experience, so this is what I propose."

"Your punishment is to keep a journal every day for the next month, faithfully, writing to me about feelings, wants, needs, and desires. Nothing is to be hidden from me. If you fail to write each day, the punishment will be worse.

Does this sound fair?" He said.

"Yes, it seems very fair to me. Where should this journal be kept?" she asked.

The details were worked out, and Ana began writing her journal to Weston. One day He replied to her journal and said, "I know there is more, Ana. Tell me." He also said for her to address Him as Sir from now on, so Ana adjusted to His request quite easily.

The journal began to show her things about herself that she never thought possible. One day she knew this journal would be looked back on and she would wonder how this all started.

The next month went by quickly. Smoothly, Weston continued guiding Ana through different things and explained parts of the lifestyle that she had questions about. Ana found herself becoming more and more sexually attracted to this man. She would cream her panties just typing away with Him. The sexual urges were growing in intensity. She so wished He would touch her and finally she placed these thoughts and feelings in her journal.

That afternoon, He did touch her, the slightest of kisses, barely His lips touched hers, his hands roamed lightly over her arms, describing it in detail as her body flooded with heat and desire. She was falling for this man. They both knew she was, and so Weston felt it was time to try something else.

"Ana, how would you feel about talking to me on the telephone?" He asked.

Ana sat trembling at the keyboard. To hear His voice, something she had dreamed of in her sleep, she wanted that so badly, but to actually allow it to happen... What if He was a psycho killer and all the other evil things she had heard about the Internet?

"I would love to talk to You, Sir. I am a little frightened though," She replied.

Weston gave her His phone number, allowing her to call Him first, so that she would realize that He was safe. Ana called Him. His voice was smooth, sexy almost sultry. It felt like warm butter over pancakes. Ana melted. Weston explained to Ana that He wanted her to gather a few things for their next call.

He asked her if she owned a vibrator. She was horrified. "No!" she said.

Weston laughed in a very relaxed voice and instructed her to go buy one, and to also pick up a set of chain nipple clamps with the tiny clips not the big clover ones. He instructed her to pick up a small bag of clothespins and to order butt plugs -- Small, medium and large. Ana's eyes were like saucers. Her mind was reeling and she was ready to say, "No way. I can't buy those things."

But that voice, it caressed her soul. She knew she would do almost anything to please Him. She said she would do as instructed and for the first time she heard the words "good girl" from Him.

Ana's body shivered with excitement. Her panties were soaked after they hung up the phone and she took off to go do what He asked for. She refused to be late this time. This time she would surprise Him and be done ahead of schedule.

Ana began searching the various toy shops online that were recommended to her. She wanted the one that would cause her the least embarassment upon delivery. Ana found one and placed the order for the vibrator/dildo combo. Looking at all the names filled her mind with naughty visions. She bought the economy anal pack that had three sizes of butt plugs and it had an anal dildo.

She also read it had something called "Anal Ease." By the time Ana got to the nipple clamps, her pussy was drenched and so hot. She wanted to cum so badly. Instead, she finished the order and headed out to the local store for the clothes pins, wondering just what in the world Weston wanted these for. All she wanted was to please Him. Ana grabbed a pack of 100 wooden pins and a few other items and headed out to the car, belly still fluttering every time she thought of talking to Him on the phone.

As Ana drove home, her long blond tresses fanned in the wind from the open window. Ana belted out the tune that came on the radio, "I wanna kiss you all over." She was radiating. Her beautiful glow could be seen by anyone. Ana felt decadent, naughty, and sexy. Anastasia couldn't wait to see Weston online tonight. She was going to tell Him about the things she picked out and even show Him the pictures.

Anastasia kept her thighs squeezed so tightly on the drive home, anything to relieve the pressure. Weston had not done anything sexual with her but the more they talked, the more Ana's desire increased.

Anastasia saw Weston on briefly online that night, showing Him the pictures of what she bought, and He said "Good girl." Ana's heart soared like floating on air. The smile would have melted His heart this time. Weston asked Anastasia if she was horny? Ana blushingly typed in a big "YES!"

Weston asked Ana to slide her finger between her slit of shaved petals. He typed in for her to not type anything back until she needed to cum. His words began appearing quickly, instructing her to rub her clit. Ana was way ahead of Him. She was rubbing and pinching and pulling upon that swollen nub. He instructed her as well to get two clothespins out of the bag and place one on each hard nipple.

Anna's first reaction was, "Oh, my," as it caused a burning sensation that after a couple of minutes seemed to fade away. Weston knew it would. Anastasia continued to rub, pull, and pinch, finally sliding two fingers in that hot little cunt, feeling the juices cover her probing hand, hips grinding against the palm, fingers dug in deeper.

Weston finally saw a set of lines going across the page. He smiled as he typed, "Not yet."

Ana began entering the lines urgently, over and over. She was so close. Finally seeing the "cum NOW," Anastasia's body jerked as juices flooded the palm of the hand, heart pounding as wave after wave of pleasure engulfed her. She had even screamed out during the orgasm.

After a moment or so, Weston typed in another message. "Remove the pins," it read. Anastasia had no clue, but reached for the first one, and the skin seemed glued to the wooden material. The sting and burn made tears prick her emerald eyes. She told Weston this, and He informed her that this was a normal reaction.

As Ana removed the other pin, she panted through the pain, surprised by the warmth that began to fill the mounds of aching flesh, turning to an intense heat. Weston instructed Anastasia to write about this in her journal. He wanted to read how she had felt during this first time with Him.

Ana glowed again. Her body was languid in feeling. Ana told Weston "goodnight," and they both logged off and headed to bed.

Ana's toys arrived, and she immediately emailed Weston explaining everything was here. Ana also put her phone number in the email. She trusted Wes and was showing this in good faith. Weston did not call, but gave Ana instructions on the toys. He allowed her to practice with them some before she had to use them full out. Ana practiced with the dildo/vibrator, and was amazed that the orgasm was achieved so quickly.

After the clothespins she was a little nervous about the nipple clamps. They looked ominous after the wooden pegs that she had once viewed as so innocent. Ana got ready for work and headed out the door. People at work commented on how she had a glow. Her face shone brightly and her hair was like shimmering fire. Anastasia felt on top of the world. She was able to log onto the computer at work, and about lunch time she was surprised to hear a little bleep. Ana looked down and saw Weston was online. Her heart stopped.

Weston and Ana both said hello to each other through typing. Weston asked if he could call her at work. Ana immediately gave him the phone number and waited on the edge of her seat for His call. The phone rang, and for the first time she heard His voice. It seemed to melt over her like a warm bath. Ana caught herself almost moaning just from having heard Him.

"Ana?" Weston said.

"Yes?" Ana replied

"Hello, Ana. How are you?" He asked.

"I am doing ok Sir. Thank You for asking. How are You please?" she whispered out.

"I am doing great Ana. It is wonderful to speak with You." He responded.

Ana was feeling the juices between her legs, and how her body reacted to this man was incredible. His voice seemed to change tenor at different times, causing her pussy to respond differently to the types of tones.

"What are You doing, Ana?" Weston asked.

"Nothing, just talking to You," She said.

Weston waited a moment. He had called to hear her voice and speak with her. Now she had forgotten to say Sir. What to do. He was quiet. Ana's voice disrupted the empty space.

"Is something wrong?" She said?

Ahh, there Ana had done it a second time. Weston was thinking of all sorts of ways to punish this infraction at work. He did not want to cause her to regret the call, but she had to be taught that there are consequences to one's actions, even the little ones.

"Ana, you forgot something twice in your dialogue," Weston said in a totally different voice.

Ana thought a moment and felt a slight fear suddenly. Oh no, she knew what she forgot, and now she knew He would ask her what should be done about it.

"I forgot to call You 'Sir,' Sir. I am so sorry, Sir. Please forgive me. It won't happen again. I promise I won't forget again Sir." She stumbled over her speech.

"No Ana, I know you won't forget again, but now what should I do to make sure you do not forget?" He whispered.

"You should punish me, Sir," Ana said without hesitation.

"Yes you will be punished. Open your desk drawer, Ana. Tell me the items inside please," Weston asked.

Ana quickly got the drawer open. "Sir, there are pens, pencils, scrap paper, rubber bands, paper clips, tape, and a ruler," she said quickly.

Weston thought for a moment. His mind looked at details of everything she said.

"Ana, I want you to go to the supply closet and get two of those black binder clips. Medium sized is the best," He said.

Ana asked, "May I go now, Sir?"

"Yes, go now and hurry," Weston responded.

Ana hurried out of the office after placing the phone down, went to the supply area, and looked around for what He wanted. She found two of a medium size and some small ones. She grabbed the two clips and rushed back to the phone. Her cunt ached badly. It was on fire. She had never felt this hot before. She returned to the phone.

"I am back, Sir," she said.

"Very good, Ana," He replied

"Now Ana, this is what you are to do. Is there anyone in your office that can see you right now?" He asked.

"No Sir," Ana replied

"Good. I will assume you are wearing a dress. I want you to pull up your dress. Pull your panties down and then attach one clip to the left shaved petal and the other to the right. Do this now Ana," Wes said in a very sultry voice.

Ana was in awe, but she replied, "Yes, Sir." Ana's fingers trembled as the dress was lifted, revealing silky white flesh. Her panties were soaked, to her surprise. She pulled them back and attached the clips to first one side then the other. Oh god, her mind was screaming as the clips burned like mad. It felt like her pussy was in a vice. She then had to sit down. As she did so her body went nuts. Ana was panting, trying to breathe through this pain. She picked the phone up and tried to hold very still.