Cheater Wedgie Slave

Gym

After Jordan warmed up in the bath both of them headed to bed and the next morning Jordan woke up to Emily sitting on his back and pulling up his underwear. "It's so early" he said as he moaned into his pillow. "Never too early for wedgies" Emily responded and she pulled harder on his underwear. Soon she heard ripping and she hopped off his back. She then reached into one of the shopping bags she had up in her room and handed Jordan a new pair of spandex underwear. "These are way too small" Jordan said as he squeezed them on. "I know, now put them on your shoulders" Emily said smiling. She then watched Jordan struggle at pulling the small underwear up, grimacing the entire time. He got one side up on his own, and Emily helped with the other side. The wedgie was so tight he could not stand up straight, he was arched over to spare his groin any more pain. "Stand up" Emily said smiling, Jordan then slowly started straightening his back and moaning until he was finally up all the way. "Alright get dressed we're going to the gym. Jordan had a worried look but continued dressing.

Once they were dressed they got in the car. Each bump was torture for Jordan causing him to moan each time. When they got to the gym he tried he best to walk normally but failed, he then remembered the collar and hoped no one would notice. Inside they started on the the treadmill, Emily reached over and turned up Jordan's until he was running and she chose to stay at a jog. Jordan's ass was burning. After about 30 minutes Emily led him over to the arm machines. She stood next him and watched him struggle. Each time his arms went up his wedgie dig deeper into his ass. He tried to keep his moans quiet but some of the people around him had to of heard. Once Emily thought he looked miserable enough she allowed him to stop. His ass had to have rubbed raw at this point. "Alright 100 squats and we can leave" Emily said. Jordan's face turned white, he knew that the squats would be the worst of all. They walked over to an area where there weren't many people and Jordan started. He counted out loud and each time he came back up his eyes met Emily's. She loved how uncomfortable he was.  He made it to 75 and he stopped "Please" he said hoping Emily would have some sympathy. "Ok make it 150" she replied not looking up from her phone. Jordan continued and was on the verge of tears his ass had to have been bleeding and his balls pushed inside him. He made it to 150 and fell onto his back panting "Thank you mistress" Once Jordan collected himself both him and Emily headed to the car. Jordan looked exhausted, it had been so long since he had worked out, he was naturally fit. He was just looking forward to going home and removing his wedgie, his ass was burning. Instead of going home right away Emily stopped off a her favorite restaurant, prolonging Jordan's pain.

When they finally got home Emily ordered Jordan to strip and shower,he did as told and returned back to her and stopped in his tracks. Emily was holding the butt plug. He dreaded what was coming next. Emily motioned for him to come to her and she laid him across her lap. She lubed the plug and put it in Jordan's raw asshole. "Fuck" He moaned as Emily finished putting the plug in. She slapped his cheek causing him to jump "watch your language" They then sat in silence while Emily finished. Once the plug was in Jordan got dressed as usual and headed back downstairs. Before Jordan sat down Emily handed him the cock ring to which he quickly put on and sat. She then pulled out some rope she was hiding behind her and began tying Jordan up. She wrapped all the way around him to where he could barely wiggle and he was stuck with his arms by his side.  He looked like a worm. Emily finished off her masterpiece with a ball gag. She sat down next to her bound slave and turned on the vibration setting on the cock ring, it turned on and off at random times and intensity levels. She proceeded to grab her book and begin reading, listening to Jordan moan, it was music to her ears. She later closed her book and fell asleep, leaving Jordan to suffer.

She woke up about 3 hours later. Jordan was in the same place she left him in. She reached over and took out his gag, turned off the ring, and untied him. Once he got all of the ropes off he relaxed into the couch and sighed. Emily then got up and went to check the mail, she comes back and hands Jordan a package and he begins opening it. When he got it open he wasn't sure what it was, he looked at Emily puzzled. It's was a metal device that came packaged with a small lock and key. "It's a chastity" Emily said with a smile. "A what?" Jordan replied "Take your pants off" he did as told and Emily took device and placed and locked it onto Jordan's dick and balls. "Ok now you can't get hard." Jordan looked nervous "Go on try" Emily said as she took her shirt exposing her breast. He could feel the blood rush to his cock, and it struggled against its new found cage, it could only twitch. It was painful. Once Emily saw it worked she put her shirt back on. She then took the key and threaded it to a chain and wore it as a necklace. She was wearing the key to Jordan's cock around her neck. She now controlled when the next chance he could cum. Emily then sat back down and turned on the tv.

Later that night they sat down and ate left overs from the previous night. Jordan was squirming due to the fact he had an 8 inch plug inside him. After dinner they headed to bed, Emily had an ideas for tomorrow.