Jessica's Anal Training

Jessica was a young submissive with a lot to learn. Although she tried to please Rick, she had always refused his anal advances.

Rick had heard enough of Jess's excuses, today was training day.

Jessica completely undressed for Rick as he handed the leather wrist and ankle restraints to her. Jess strapped on her ankle restraints just like the many times that she had done in the past. Rick helped her with her wrist cuffs and secured them together.

Rick led Jess to her beam and attached her wrist restraints to the pulley system. He took the slack out of the rope until Jessica's arms were suspended above her head.

Rick then knelt before her and secured the spreader bar to her left ankle cuff. He told Jess to spread her legs so he may attach the other end of the bar to her right ankle.

Jessica knew she was to be punished for her actions, but did not know what Rick had in store for her.

Rick walked around behind her and whispered in her ear, "what are you going to tell me the next time I want to fuck that tight little virgin ass, huh?"

Jess hung her head and in a soft tearful voice said, "please, no,"

Rick just shook his head and grabbed his home made leather whip. It was only eighteen inches long, made of soft lacing material.

Jessica felt the first of five lashes across her tight ass and cried out more in surprise than in pain.

Rick told her to be quiet or she would be gagged. Jess stood there taking her lashings until he had finished. He lightly touched her tender ass sending a shiver through her body.

Jessica watched as Rick opened the brief case with all of her toys. He grabbed the plastic clothes pins and a vibrating egg.

Rick kissed and fondled her breasts and played with her nipples between his thumb and forefinger until her little nipples were hard. The clothes pins had been modified to make the springs weaker and a key ring had been added for weight.

With care, he attached a clothes pin on each nipple. Rick then knelt between Jessica's legs just inches from her clean shaven pussy.

He wet one finger then slowly parted her lips inserting it all the way. Her pussy was wet already from her punishment she had received.

He pulled it out even slower and offered the sweet juices to his slave. Jess sucked on his finger as she felt the pressure of a clothes pin gently clamp down on her left labia, then her right.

Rick left her standing there as he went to the other room. She watched as he returned carrying something she had never seen before. It looked like his video camera tripod, but without the camera.

Rick had modified the camera mount to accommodate a large butt plug. The plug was 3/4" at the top and gradually swelled to 1-1/2" at the base and nearly seven inches long.

Rick set up the tripod under Jess and cranked the plug up near her virgin hole. He grabbed the lube and liberally applied it to her new toy. He then ran his lubed fingers around, then slowly in her tight hole.

Jessica stood on her tip toes trying to prevent him from sticking his finger any deeper. With his finger in her ass hole, Rick grabbed her support rope with the other hand and pulled up all of her slack. He pulled out his finger and positioned the plug just at her forbidden entrance.

Rick then cranked the tripod up inserting the plug just an inch in. Jessica tried to get higher, but she was at her limit.

Rick stood behind her and grabbed the rope that secured her on her toes. He gently released the tension giving her arms a little slack. She tried to suspend herself on her toes, but her legs and knees were getting weak.

Jess felt the plug going deeper and deeper as she knew that she wouldn't last mush longer.

Rick knelt again in front of her and grabbed the vibrating bullet. He turned it on high and touched it to her left clothes pin attached to her labia. The sound and vibration shot through her body and left her weak sending the plug even deeper inside. Rick touched it to her other labia and stuck his tongue on her clit.

He licked and sucked on her clit leaving her body thrusting out of control. Rick stopped with the bullet and the teasing of her wet pussy when he notice that Jess was almost flat footed.

Jess tried to pull herself up, but was just too weak. Rick released even more tension on her rope and knelt back down. Jessica heard the bullet again and waited for the touch.

She felt Rick's finger slide into her, then stop. She held the rope tight as he wiggled his finger in her deep.

Rick grabbed the bullet and pushed it firmly against Jessica's swollen clit. Jess lost control and slid down fully on her seven inch plug.

Rick fingered her pussy faster and faster while moving the bullet back and forth on her clit hard.

Jessica started to moan and push against Rick. She felt herself starting to cum, but this felt different. She had this plug deep inside her and wanted more.

Rick pulled the vibrating bullet away from her clit and slowly slid his finger all the way out. He again offered Jess to taste her sweetness and told her that he wanted her to cum for him, but not until he said that it was okay.

Jess felt her wet lips being parted. Rick pushed the bullet inside followed by two of his fingers. He pushed as deep as he could and turned on the vibrator.

Jess pushed towards him as she felt herself starting to lose control.

Rick started to lick her clit as he slowly pushed his fingers in and out of her.

"Oh my God," she cried as Rick thrust his finger in her hard.

Rick told her, "not yet," but it was already too late.

Jess screamed "Noooooooooooooo," as she gushed all over Rick.

He stopped what he was doing and very slowly, removed his fingers and the toy. Jessica stood there weak with her plug still deep inside. Jess knew that Rick was going to punish her for losing control and Cumming, but right now, she didn't care.

Rick again asked, "So, what are you going to tell me the next time I want to fuck that tight little ass?"

Jessica looked at Rick and smiled . "Please fuck me in my ass."