Cheater Wedgie Slave

Surprise

The following morning Emily woke up early and headed out to the backyard, she was setting something up for Jordan. Later, Jordan woke up and headed downstairs to look for Emily, he found her sitting on the back porch. "What's that" he asked pointing to a rope that was tied from the step railing to the top of a tree about 25 feet away. Tye rope started off low be went higher up the closer it got to the tree. "Here, I'll show you" Emily said as she grabbed Jordan's hand pulling him closer. She then hooked the back of his underwear to the rope, which was at waist height. "Ok now walk forward" Jordan began walking forward. There were knots in the rope, so once the hook went over the know Jordan could not go back. He realized as he was walking he was slowly giving himself a wedgie. He turned around to see Emily smiling, she was happy it was working. "Go on" She said as she pushed him, causing him to stumble forward. His underwear was up to his shoulders at this point, but he kept going. Eventually it was almost higher than his head, and he was walking on his toes. He was about 5 feet from the tree, he kept walking. When was on the very tip of his toes he was basically hanging, due to the fact that his toes weren't much support. He was trying his hardest not to fall over when suddenly Emily came up behind him, picked his legs up, and carried him the rest of the way to the tree. She then dropped him, now he was completely hanging. He was wincing because he still had the plug in and it was pushed deeper inside him. "Ok there, I did it, can I come down now?" Jordan asked while trying to use his hands to lessen the wedgie. "But the fun has just started" Emily said as she pushed him, causing him to swing. His plug was now deeper inside him than it had ever been before. She then walked up to him and began pulling the front of his underwear up. "Babe please" he moaned. The expression on Emily's face changed. She proceeded to punch Jordan in his crotch causing him to cry out in pain. "Do not call me that" Emily's said as she resumed pulling the front of his underwear up, she then placed it into his mouth "hold it". He bit down on the waistband. She started going inside but decided to push Jordan one more time out of spite, causing him to moan. He loved everything about the situation. He felt his dick attempt to get hard but his new chastity was obviously preventing that, so he just hung there swaying in the wind.

Emily went inside to prepare her next wedgie for Jordan. She went to the basement and tied 5 ropes starting from short to long to the support beam on the room, making sure her knots were tight.  She then heard the door to the basement open, it was Jordan, his underwear had ripped and he appeared to still be wearing it. "Oh right on time" she said as she handed Jordan a pile of underwear, "put these on, starting with the g string" In the pile was a g string, a thing, a pair of panties, a pair of Jordan's normal underwear, and the spandex ones. "All of them?" He asked puzzled "yes" Emily responded, Jordan began putting all of the underwear on until he reached the spandex pair. By the time he was done Emily already had a stool for him to stand on to she could tie his underwear to the ropes. The shortest rope was tied to the g string and the longest to the spandex pair. Now each time a pair ripped Jordan would then be caught by the next pair. Emily then reached into the players of underwear and placed the cock ring onto Jordan and proceeded to tie his hands and feet, and gag him. "Ok I need to go grocery shopping, so this will definitely keep you here until I get back" she said as she quickly kicked the stool away causing Jordan to fall and be caught by the thing fabric of the g string. Before she left she turned on his cock ring, which when placed on the chastity vibrates his entire crotch, and then left. It wasn't long after he heard the front door shut when the g string ripped, causing him to fall and be caught again by the thong. All he could do was moan. His dick struggled against his chastity device but to no avail. About 30 minutes later the thing ripped and the panties were wedgied up his crack next. His plug he now been pushed up against his g spot in his ass causing him even more pleasure.

It had been a few days since Carly had heard from Jordan or Emily and so she decided to head over to Emily's to check on her. When Emily left for groceries she took Jordan's truck, leaving her car in the driveway. Carly saw Emily's car and assumed she was home. She went and rang the door bell but there was no answer, she decided to use the spare key that was hidden in the front yard, she wanted to make sure Emily was ok. Once inside she called out to Emily but heard no response, she only heard faint moans coming from the basement. She headed down there to see what the noise was. To her surprise she saw Jordan bound, gagged, and in a hanging wedgie. All he could do was moan when he saw Carly, his panties had ripped he was now hanging from regular underwear. "Oh my god what did she do to you" she said as she attempted to free Jordan, she first removed his gag. "Don't take me down, she'll be home soon, she'll get mad" right after he spoke they both heard the front door shut and lock. It was Emily.

When Emily went downstairs to check on Jordan's she was shocked to see Carly standing in front of him. "How the hell did you get i here?" She asked, already becoming angry. "I was worried about you so I used the key." Emily saw her chance and took it, she tackled Carly and began to tie he hands and feet. "What the fuck are you doing Emily sto-" She was cut off by Emily gagging her with some loose fabric. She then stood Carly up and walked her over to the hook for the wench, she hooked her underwear onto and walked over to the controls. Slowly Carly was lifted into the air by her underwear, she was only 5 feet tall so it wasn't long until she was off the ground. All Jordan could do was watch, and moan of course. Emily then stepped back and assessed he work. Both Jordan and Carly were now hanging in her basement by their underwear. Emily had to start planning, she wasn't expecting a guest.