Phone Sex the Next Predicament

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Special thanks to BDSM Bill for editing my work. You have helped my writing in a great way Sir and You are appreciated. niyah

Anastasia looked forward to hearing from Weston every day – well, almost every day. She still went to chat rooms and tried to fit in with others, but it was almost impossible. Anastasia would sit and watch all the disrespect in the rooms and have to leave. When she would ask Weston why these girls were allowed to act this way or comment on their disrespect, He always replied the same way. “It is not your place to judge, now is it?”

Anastasia knew that a submissive was not to judge others. Watching how things went on in chat would drive her crazy. She would sit thinking to herself that these girls would not last five minutes with Weston. Time seemed to fly by. Weston would catch her every slip up. It was like he had a spy cam with a supersonic ear piece. He would hear the slightest infraction. Ana was at work one day and Sir called. Her heart raced a mile a minute, just like it always did when he called. He greeted her, and she made sure to greet Him as Sir. She would not forget the first lesson. The conversation seemed very mellow. Ana had relaxed and started to speak openly, or freely for a better term.

“How are You today, Sir?” Ana asked.

“I am doing pretty good,” Wes replied.

“That is good to hear Sir. I have missed talking with You Sir,” Ana said.

“Oh yeah?” Wes asked.

“Yes Sir, I have missed You a great deal Sir. I have finished my assignments and am still working on writing about them Sir.” Ana said.

“Yeah? Really?” Weston countered.

“Yeah Sir, really I have Sir,” Ana said, not thinking.

Wrong! She was busted. “Yeah” was a word for lazy people. Sir did not allow Ana to be lazy. Ana felt her ass tighten so hard, her stomach turned to a sinking feeling. He had baited her and she had relaxed to the point of walking right into the trap. Ana even thought she heard a chuckle because He knew she knew she was in trouble.

“Ana, what have I told you about the word “yeah”?” Wes asked.

“That only lazy sluts use the word “yeah” and that it shows a disrespect to the dominant, Sir,” Ana replied.

Her voice was almost trembling, but at the same time she felt the rush of heat to her clit. Her pearl was throbbing, and the first little trickles of moisture were flowing forward. Ana blushed because this was one reaction she had not figured out why it happened yet. Soon though, she would understand. Weston was listening to her on the other end and He could hear the sudden catch in her breath when His voice changed and He told her, “Good girl, for the right answer.”

Wes instructed Ana to shut her office door, sit back down in the chair, and to lift her dress so that her pussy was open to the air. Wes knew she was in a dress because He had instructed that she wear them always. Why, you might ask? Well, so that she was always accessible for use. Pants interfered with the dominant’s pleasure, for they were time consuming to get out of quickly. Whereas with a dress, He could bend her over the chair, the desk, throw her to the floor on all fours, and have His way with her any time of the day or night. Ana always shuddered and soaked herself when He would remind her of how she was to dress and why.

Ana lifted her dress, feeling it slide up the silky thighs. Her pussy hot and swollen. Weston instructed Ana to smack her pussy really hard five times. She was to make sure He could hear her smack it or else she would have to start over. Ana’s heart raced. What if someone heard her out from the hallway? Ana bit her lip to keep from crying out. She had done this before, and she knew what it felt like, but here at work made her a nervous wreck.

“May I place the phone down, Sir?” Ana asked.

“No Ana, keep the phone up so that you may hear me,” Wes replied.

“Yes Sir,” Ana said.

Ana kept the phone near her ear. Little tiny beads of perspiration began to film her forehead. She tossed the blonde rings over her shoulders. Hearing Him tell her to start, Ana smacked one time. Wes said, “Stop.” She knew why, and started over. The next time her hand connected with those shaved lips the fire that ripped through those petals exploded deep within her brain. The pain was incredible and she knew He would have hit harder. The second one came down, connecting solid with the flesh once more. Her yells were being bitten back, but the tears could be visibly seen. Ana kept watching the door. Again her hand fell hard.

At the other end of the phone line, that voice that soothed, controlled, punished, disciplined, and pleasured, said, “Harder, Ana.” Ana’s hand came down a fourth time, harder than the first three. The sound in the room echoed like a gunshot. Succulent lips parted as a cry escaped. “Yes Ana, that is it,” Wes said. Ana’s cheeks were wet from the tears as the sting tore through her body. Finally, the fifth smack. Ana sat back, making sure her thighs were parted widely. Her petals were wet with juices. The room smelled like her sex. SMACK one last time. She turned her head into her arm and bit down to keep the scream from being audible to the hallway.

Ana’s cunt was on fire. Ana’s lust was growing rapidly. The last slap had left her soft-shaved petals looking like flesh burnt by falling asleep in the sun. Wes told Ana she had done well, and He was pleased with her efforts. He assured her that if he had been there He would have hit three times as hard, and probably with a flogger, crop or possibly a whip. Ana felt the juices gushing. The thought of Sir flogging her drove her senses insane.

“Ana, what did you learn?” Wes asked.

“Two things, Sir. One is that it is never okay to disrespect the dominant by being lazy, and two, always expect discipline to be swift and done immediately as the infraction is then well learned,” Ana said.

“Good girl,” Wes said in that voice, the voice that always let her cum or led her up to that point and made her wait.

Ana’s tongue slid out softly, caressing the lower lip. Squeezing the heated thighs together, trying to ease the sting from the petals, Ana adjusted her position. Ana knew she did not make a noise as she moved, and when His next words came across and connected with her ears, Ana almost fainted.

“Open your thighs, Ana. I did not tell you to close them. Do you think your suffering should be eased so soon, Ana?” He asked.

“Oh, umm no, Sir, of course not. But, but., How did You know, Sir?” she queried.

Wes explained it was a natural reaction to any discomfort from there and He figured she would try to alleviate the building pressure that He knew was growing between those slutty thighs. Ana blushed because she knew He was right.

“Do you need to cum, Ana?” Wes asked.

“Yes Sir, please Sir,” Ana pleaded.

“Do you deserve to cum, Ana?” Wes asked.

“Only if You say I do, Sir,” replied Ana.

“No Ana, that is not the correct response. You tell me. Do you deserve to cum?” He asked again.

“I was punished Sir, and I did the punishment, so yes, I think I should be allowed to cum,” she said with a little confidence.

Wes chuckled a little, hearing that trembling need in her voice. He already knew He was going to allow her to cum. She had done as He had instructed and had done it very well. He also knew that Ana got very wet when her pussy was smacked. Wes began to talk to Ana, painting the picture of her kneeling at His feet, how she would present her pussy to be whipped and would do it gladly. Ana always had a little trouble with this, thinking, would she be able to do this? She would ask Sir and He, of course, would put it right back to her. “Would you Ana?” So it would go on.

“Ana, run your fingers up your slit. Slowly. Ahhhh yes, that is what you wanted isn’t it?” He asked.

“Yes Sir, oh yes Sir,” she replied with breathless excitement.

“Pinch your clit, Ana. Harder, Ana,” He said.

Ana pinched her clit hard, then harder as He instructed. Her moans were growing even through she was hiding her face against her shoulder. She was thankful her office was locked and no one should need her for awhile. She was rubbing, pinching, the phone cradled against her shoulder and chin as another finger grasped a hard nipple and twisted and pulled, then twisted again. She had thoughts of His mouth upon the taut bud, His teeth biting. She was moaning out as the orgasm drew closer, panting through the motions of His instructions, pull, pinch, smack, twist. Ana’s pussy was dripping. Her belly was spiraling tightly. Suddenly she heard His voice. Something she had grown accustomed to was for Him to count.

“5, 4, 3, you better cum on 1, bitch, 2,, don’t you hold back on me slut, 1!” Wes said in a deep seductive way.

Ana felt the tension build with each number. The harder she pushed her body towards the brink as she heard His words, the faster her fingers flew over the clit, her other hand sliding two fingers deep inside, slamming forward at two as the other hand pinched the clit hard. Her body hit release at “one” as she cried out, allowing the juices to flood forward, caressing her hand, feeling it slide between her thighs upon the seat, gasping for air as the lights of brilliance exploded behind tightly lidded eyes, her heart pounding in her ears, large breasts, and the tortured pearl. Panting as the waves kissed the flesh, Ana rode them all the way through.

“Good girl!” Do you feel better now?” Wes asked.

“Yes Sir, oh my yes,” Ana replied with a silky, orgasmic voice.

“Good. You did well, Ana. I am well pleased with you,” Wes said.

“Thank You, Sir, for allowing me to cum. I am still confused though about why the spanking made me so hot anyway, Sir,” She said.

Wes knew Ana was still very unused to this aspect of the lifestyle. He would take time to explain the feelings and allow Ana to feel at ease before ending the conversation. His explanations gave Ana a lot to think about. As always, Ana would write the feelings down and any other questions. Wes stayed with Ana on the phone for awhile once again as she came down from a place she still didn’t quite understand.

Wes and Ana talked for a while about how much slapping her pussy hurt, and what else she worried about during that episode, like people walking in or hearing her doing this, her co-workers being able to smell her sex as now that she had cum it was even stronger, and the fear of displeasing Him that drove her to do as He said rather than to say no.

Wes felt Ana was coming along nicely, and she still had a lot to learn and experience. This was not something that was just rushed. He would take her to other levels one at a time, breaking through that façade she had worn for so long, the one that she still thought she was keeping up with Him. If she only knew that He was really entering her and working His way up inside her towards her heart. Would she notice, or would He just keep pushing down walls and plowing through barriers she put up to guard herself?

Wes instructed Ana to use the small butt plug tonight, lubing it and wearing it for an hour, holding it in and not allowing it to fall out. The small one would probably hurt her if she was not careful, He explained to her. He told her to make sure she lubed it well and her ass, too. She might want to play with herself a little before trying to push it in, and to also do it very slowly. Take deep breaths.

Ana took all this in and thanked Him for His patience and care. She said she would do as told and report back to Him about how it felt and what it was like. Her ass tightened up the moment He said “butt plug.” she knew it was coming, but now it was here. She was wondering what could possibly be next. Guess We will find out next time.

“Goodnight, Ana,” Wes said.

“Goodnight, Sir,” Ana said.

The two hung up, and Ana finished up her day. Thoughts of the butt plug plagued her mind as she waited to get home to do this assignment. She was not a virgin when it came to anal sex, but it had been a very long time. Arriving home, Ana made sure no one was around and pulled out the new pink piece of rubber. It seemed fairly small when she looked at it closely. It came with this lube that was to help it slide in easily, and she hoped this was true. Ana lay on the bed and turned to her side. Her fingers gently lubed the puckered part of her ass. Her pussy began to throb again, and of course it was very sore from earlier. Placing the same lube upon the plug, Ana slowly pressed the tip forward towards the ring of tight flesh. The feeling was odd at first, and then, as it began to go a little further, Ana could feel her body begin to reject the idea. “Oh god, this hurts,” she thought. She tried to relax, using her other hand to slowly caress her clit. Feeling the heat begin to build, she pushed and pulled on the plug.

Ana’s body began to tighten towards orgasm again. The plug was half in, and she was working it, thrusting softly, easing it in and out. It felt odd, but so good at the same time. Suddenly it slid home, all the way to where it was securely inside her tight ass. Ana kept playing with her clit as she rocked back on her ass, making the plug move in as it would slide out just a little with each roll back and forth. Writhing on the bed, the hardest orgasm she had felt hit her. Fluids gushed, and she felt the anal muscles lock down on the soft, pliant object. Gasping for air, heart pounding loudly, Ana lay there coming down from the spiral that ripped through her. Ana looked at the time. She began to time herself for the one hour of wear, and to gather her thoughts on what to say in her journal. Ana’s body was languid as she fell asleep.