Cheater Wedgie Slave

Sensations

Emily grinned as she heard Jordan moan after hanging himself. She continued preparing dinner, she knew she was a good cook. She set out the plates and approached Jordan and took him down and told him to get ready for dinner. "What do I wear mistress?" He said shyly "Whatever you packed" She said pointing to his bag that was still by the front door from this morning. He went upstairs and changed into a T-shirt and sweat pants and made his way down for dinner. He sat down at the table and Emily came up behind him and grabbed his underwear. She then began pulling up causing Jordan to halfway stand up before she hooked to to the back of his chair. So now when he tried to sit back down he was in a sitting hanging wedgie and he loved it. "Thank you mistress" he said. Emily then sat across from him and they began to eat.

Emily was the first to speak "I'm surprised you're still here" "what do you mean?" Jordan asked puzzled. " You had So many chance to over power me or just run away today, but you're still here." "It's because I want to be with you" He said hoping to win over Emily, but he knew it wasn't going to be that easy. "I need to go to the mall tomorrow, and you're coming with me" Emily said as she stood up to put the plates in the sink "ok- yes mistress" Jordan realized his mistake and corrected it causing Emily to giggle. She proceeded to walk over to Jordan and remove his chair wedgie and turned it into another shoulder wedgie. She then grabbed his hand and led him to the couch. They sat and Emily placed a pillow into his lap and laid down. Out of habit Jordan began scratching Emily's head. "Good boy" she said as she turned on the tv. Jordan smiled, he know realized how much her approval meant to him. A few hours later Jordan realized how late it was at that Emily had fallen asleep, instead of waking her up he carried her up to her bed. He decided to sleep on his shoulder wedgie because he didn't want to risk getting in trouble in the morning. After making sure Emily was comfortable he laid down and fell asleep also.

Jordan was awoken to a strong sensation of pleasure, Emily was jerking him off! He soon began moaning and right before orgasm, she stopped, he knew it was too good to be true "You haven't earned the right to cum yet" she said "Now get dressed but don't put your shirt on yet." He changed pants and underwear and went ahead and put his jeans and shoes on, waiting to see what Emily was going to do. He sat and waited on the bed until Emily came out of the bathroom, and he stood up to greet her. "Give yourself a shoulder wedgie" she commanded and proceeded to watch him struggle to get his underwear up. Emily then hopped up onto the bed and started helping him get his underwear up to his shoulders. Eventually they got it there and then she told him to put his shirt on. "I have to wear this in public?" He asked "You're shirt covers it, it's cold anyway you should probably wear a hoodie." She replied without looking up. They both continued getting ready. On their way to the car Jordan tried walking normally but to know avail, it was so painful, each step putting pressure on his ass and balls.

They then got in the car and headed to the mall. Each bump caused a moan to escape from Jordan. Eventually they made it to the mall and began walking around. Jordan was shocked that Emily was holding his hand. The walked around until Emily pulled him into an adult store. Jordan had a worried look on his face.  Soon Emily made her way up the the counter, he had no clue what she was buying, but she handed him a bag to carry and they walked out together. A few minutes later Emily said she needed to use the restroom but instead on splitting up and using separate bathrooms they went into a family restroom together.  At this point Jordan was sweating. She reached into the bag and opens up some packaging. It was a remote controlled cock ring. "Put this on" she commanded Jordan obeyed and reached into his already wedgied underwear about the cock ring on, and proceeded to button his pants back up. They then walked out of the bathroom together. He was nervous knowing that Emily now has control. Emily continued shopping asking Jordan's opinion on certain clothes. Suddenly when he was helping Emily grab a pair of shoes from the top shelf, his crotch vibrated. He dropped to his knees from the sudden burst of pleasure. Emily could not stop laughing as she watched Jordan try to compose himself. By the time they were done shopping Jordan's hands were full of bags, and his knees were shaky depending on when Emily turned on the ring. They eventually made it out to the car and Jordan put the bags away but kept one in his hand, the one from the adult store, he handed that one to Emily. She looked like a kid on Christmas when she opened it. She pulled out a butt plug and a ball gag. Jordan looked terrified.

Once they left the mall they decided to go out to eat. When they got into the restaurant and had ordered Emily turned on the ring, and showed no sign of turning it off. Jordan was trying his hardest not to moan, even though the restaurant was loud, he didn't want to embarrass himself. Emily noticed how close he seemed to orgasm and hit a different button causing him to jump from surprise. "Did you just shock me?!" He asked "Yeah, you still haven't earned the right to cum" Jordan rolled his eyes but was then met with another shock. "Don't roll your eyes at me" snapped Emily "yes mistress" replied Jordan realizing the waiter was standing right there with with the food. He turned red from embarrassment and hoped the whole event would end soon.

After lunch they made their way home. Once home Emily made Jordan take his pants off, including his wedgie. She then bent him over and took the butt plug she had already lubed up and slowly started putting it inside him. "I don't think I can do this" said Jordan wincing "Oh well" Emily said obviously without caring. Jordan was crying by the time the 7 inch plug was inside him. "Perfect, now you can go get dressed." Jordan slowly made his way back upstairs to change, later followed by Emily Jordan put on his sweat pants and T-shirt and Emily chose the same.  "Want to play a board game?" Emily asked "What ever you want to do mistress." They went back downstairs and played bored games until dinner, Jordan was squirming the entire time. They ordered pizza and sat down at the table to eat.  The hard kitchen chair pushed the butt plug farther into Jordan's ass. He was hoping Emily wouldn't give him a chair wedgie, but nevertheless she did, and the butt plug went even farther inside Jordan. He had a very noticeable look of discomfort on his face as he ate. "How do you feel" Emily asked trying not to laugh "Great mistress, thank you for the new toy" he replied with his voice shaky. Once dinner was over she let him out of the chair and they went and got ready for bed. Jordan asked if he could shower and Emily said yes and as he was undressing she removed his cock ring but left the butt plug in. After they were settled Emily surprisingly snuggled up against Jordan. Jordan didn't know how he was going to to take 2  months of this.