Cheater Wedgie Slave

Ownership

The next morning Jordan woke up to the smell of breakfast being made. He greeted Emily when he got downstairs "Good morning mistress" "Morning" she replied they ate breakfast, and to Jordan's surprise there had been no wedgie yet, even though he still had the large plug inside his ass. "I set up something for you in the basement today" she said with a smile. After breakfast they headed down stairs. What greeted Jordan scared and exited him. There was a 200 lb barbell attached to a pulley system and on the other end there was a rope. Emily ushered Jordan to the rope and barbell. "Pick it up" she commanded and Jordan did as told, he was strong but he knew after awhile it would become heavy. Once he had the barbell in hand Emily tied the rope to his underwear. Now if Jordan lowered the weight below his head the the pulley system would begin to pull on the back of his underwear. "Ok have fun" Emily said as she turned to leave, she then headed upstairs to read.

About 2 hours later Emily heard Jordan cry out in pain. She new he dropped it. Jordan weighed 172lbs and the weight was 200lbs. So from the sounds of it her pulley system worked.

Jordan couldn't believe he let it drop. His underwear shot up his ass thanks to gravity, and he was lifted off his feet. All of his weight was know put on his asshole and the butt plug went farther inside him. He could help but moan, he loved and hated this. After about an hour of hanging Emily came in and let him down only to reattach his underwear to the wench hook and place the cock ring back on. She then started the wench, which started lifting him up by his underwear. Once he was about 4 feet off the ground she tied his hands behind his back and attached the barbell to his legs, causing him to sink farther into his hanging wedgie. He now had 372 lbs weighing him down. He was moaning and on the verge of tears. Emily walked up and and put in the ball gag that she bought yesterday. She then sat across from Jordan in the corner where they were keeping their old couch and she laid down. She then switched on the cock ring to vibrate at random times and intervals. Once the ring was on all Jordan could do was moan into his gag. Emily just laid there and smiled at her helpless partner. He tried to speak but of course he couldn't.  Without noticing, Emily dozed off.

About five and a half hours later Emily awoke to the same sight she fell asleep to, except this time Jordan looked defeated. She quickly got up and turned off the ring, let him down, took out his gag, and untied his hands. He then fell to his knees, he looked so tired. "Thank you mistress" he said while still on his knees. "I didn't mean to sleep that long but I'm assuming you enjoyed yourself" she said while running her fingers through his hair. "Yes mistress" he replied. She then took him upstairs and ordered him to strip and bend over, where she removed his plug and ring causing a sigh of relief to escape Jordan. She then allowed him to go shower and then meet her downstairs for dinner.

Once Jordan finished showering and composing himself after the five hour long wedgie he headed down stairs. He was greeted by Emily opening boxes of take out food. They both sat down and began eating Emily was the first to break the silence, "I have a gift for you" She said smiling, which worried Jordan. "Close your eyes" she commanded, and He heard her get up from her chair and walk over to him . He then felt something around his neck click. "Okay open" she said as he went to sit back down. "What is it?" Jordan asked. "Get up and look in the mirror", he did as told and to his surprise he was now wearing a dog collar, it was camouflage and the tags even had his name on them and Emily's phone number. He was hers now. "Thank you mistress" Jordan said as he sat back down to finish dinner.

After they both finished eating and had cleaned up Emily asked if they could sit back down at the table together, of course Jordan complied. Then Emily reached into her pocket and pulled out Jordan's phone, his face turned ghost white. "W-where'd you find that?" He asked knowing what was about to happen. "This was under your pillow, it appears I have been too soft on you, I had sympathy for you. Even after all I said you went behind my back and sexted Carly again. How could you?" She said as her eyes filled with tears. " I-I have no excuse mistress. I have failed you." Jordan said while breaking eye contact. Emily then quickly stood up, grabbed Jordan by his collar and led him downstairs into the basement. She made him take his shirt off, but he got to keep his basketball shorts. Without saying anything Emily attached the wench hook to the front leg holes of Jordan's briefs. He now had a panicked expression but Emily didn't seem to care. She then placed the ball gag into his mouth, tied his hands behind his back, his feet together, and quietly walked over to grab a chair for him to stand on. Once she helped him up onto the chair, she placed his cock ring back on, and quietly walked over to the wench controls where she got rid of any slack in the rope and Jordan was now on his toes on the chair. At this point he was shaking. Emily then walked over and quietly admired the work she had done. Then, without saying anything she kicked the chair out from under Jordan causing him to fall about a foot before he was caught by the front of his underwear. His underwear was so high he could not see in front of him, and his testicles were being crushed by his own weight. He cried out into the gag only for it to come out muffled. Emily walked over and pulled on his legs some more causing moans to escape from Jordan. "I'm going to head to the store real quick and then head to bed" she said as she turned on the cock ring vibrator to random. "Goodnight" She said as she headed upstairs and turned the basement light off. Jordan wondered what store was open this late, and then he realized. The sex shop.