Ex Girlfriend Shows No Mercy

[viterz72]

This is my first attempt at a story. I have tried writing a few before, but never posted anything. The plan is to have it start out pretty mellow, and progress over time to more extreme scenarios.


Chapter 1
Jake was a senior in high school. He played football and was also in the marching band. With an athletic build he had a few girlfriends through out high school, but overall wasn’t the most popular or best looking guy in the world. However, he did have a good amount of confidence and was pretty quick on his feet when it came to talking smack with his buddies. One of his ex-girlfriends Amy was a junior. She too was in the marching band but didn’t partake in any other sports. She was more focused on her studies. However she still had a nice body. She was slim with an above average booty. Her breasts were a B cup, but she still looked proportional. They broke up 3 months ago when she caught Jake kissing another girl at a party he thought she wasn’t going to attend. Since then it was pretty awkward between the two of them having to be around each other after the breakup. However after a few weeks they learned to at least be civil around each other.

The football team did a fundraiser every year where they auctioned the seniors off to other students. The student that won the bid would get to pick what the football player had to wear for an entire day and could make them dance, carry their books, sing, or whatever else they came up with. It was all in good fun and the entire school really enjoyed the day. Usually the cheerleaders would buy the players and make them wear their cheer uniforms.

Even though Jake was pretty confident he was a little worried about a few things for the auction. For starters, having to wear anything the bidder wanted for an entire day of school was unsettling. He didn’t want to be bought by a cheerleader. Also sometimes people did not get many people bidding and it was embarrassing if you were bought for only $5. Because of this he had a plan. He gave a friend $50 to buy him and had another friend bidding so that it went to at least $25. That was the average cost and he was confident a random person would not bid more than $50 for him so he could basically pick what he wore for the day when his friend bought him.

The auction was held on a Friday and then everyone who won would get to make the football players dress up and everything on the following Monday. Jake was 3rd in line to be auctioned off. The first two players auctioned off went for $30 each so he was confident $50 was more than enough to be safe. The bidding started and as expected his two friends bid up to $25. As the auctioneer was saying “Going once….. Going twice….” A female voice yelled out “Thirty”. Jake recognized the voice it was Amy. He instantly started to get hot and red. He could feel his hands getting sweaty and really hoped she did not bring more than $50. The bidding continued. “Thirty five…… Forty……. Forty five” With all the money Jake’s friends had they placed their last bid “Fifty”. To Jake’s disappointment Amy was still bidding “Fifty five”. And without hesitation the auctioneer announced “Going once…. Going twice….. Sold to the pretty lady in the back”.

Jake was sick to his stomach. He gradually calmed down though as the auction continued, and at the end everyone went to go pair up with the people who bought them. He saw Amy waiting with a huge grin on her face waiting by the side of the stage and slowly walked over to her.

Jake: Why did you buy me?

Amy: Because revenge is sweet. And if you think the guys that the cheerleaders purchased have it bad you’re sadly mistaken. I am going all out with this and there’s nothing you can do about it.

Jake: Please! Can’t we just talk about this? Maybe we could try and work through everything that happened.

Amy: Nope the time for talking has passed. I have been planning this for over a month and my mind is made up. Come over to my place tomorrow. I need to make sure everything fits.

With that she turned around and left before Jake could even summon another word. He stood there absolutely speechless and in shock wondering what in the world she had planned for him as she walked away.

[viterz72]

Chapter 2
Jake had a difficult time sleeping that night. With everything on his mind he tossed and turned with maybe a total of 4 hours of sleep. Amy messaged him right before he was about to go to bed sending a photo of a pink thong and bra with a text that read “Be at my place by 10am tomorrow” and a winky face. Jake didn’t bother responding, but he knew she was aware he read the message since his read receipts were turned on. He laid in bed until it was roughly 8am and decided to get the day over with. He got up and showered, made breakfast with coffee, and got his clothes on for the day. At 9:30 he got in his car and headed over to Amy’s hoping he would find some way to convince her to go easy on him.

He arrived at 9:50, walked up the steps to her front door, and rang the door bell. Within seconds Amy answered and seemed even more amused than she did the night before. She couldn’t stop smiling.

Amy: Good morning Bitch.

Jake: Lets just see if whatever you got fits and get this over and done with. I am not wearing a thong and bra either. No one would even be able to see it so there's no point.

Amy: You need to wear the bra because I am stuffing it with fake boobs and the thong is going to stick out the back of your outfit so when I have you pick stuff up off the floor or reach up for something people can see you are wearing it.

Jake: Amy please that’s taking it too far.

Amy: I’ll tell you what. Maybe if you change your tone and attitude while I figure out what exactly you will be wearing I will take it easier on you come Monday morning. I have 3 different outfits so there’s a chance if you start being nice I will let you pick which one you want to wear.

Jake: What are the 3 outfits? And will you reconsider the thong and bra?

Amy: I have them laid out on my bed and maybe if you do everything I ask and stop complaining today.

Amy grabbed Jake by the hand and led him into her bedroom where she had the outfits spread out on her bed. The first outfit was a white ballerina costume with tights and shoes to go with it. It had frilly outlines with gems and sparkles on it. The second outfit was a school girl outfit with thigh highs, a crop top, high heels, and a wig with pig tails. The thong and bra she sent a photo of the night before was also with the outfit. The last outfit wasn’t nearly as bad as the first two. It was a peter pan costume. Yes it had tights and everything, but compared to the other two that one would be by far the best choice. Jake was mortified by the first two outfits and was a little confused by the 3rd one, but figured it was best to keep his mouth shut and comply so there was a chance he could pick it over the other two.

Amy: What do you think? I’d say this one is favorite.

She was holding up the ballerina costume.

Amy: But I need to see you in them to really know.

Jake: Which one do you want me to try on first?

Amy: Lets do the peter pan costume first. Then I will do your makeup and nails before you try on the other two.

Jake: Cant you just do my makeup and nails Monday if you decide you want me to wear one of those outfits today?

Amy: Nope and you’re still not making a very good case for me to let you pick the outfit you wear.

Jake: Your right. I'm sorry. I’ll go change real quick.

Amy: You can change right here. We’ve seen each other naked before.

Jake: Yeah but….. ummm….. errr…… okay.

Jake thought better than to push back again. They had seen each other naked, but this would be different with her being completely clothed. Regardless it was worth it to him to suffer through being naked in front of her rather than wear one of the first two outfits to school on Monday. He started to remove his clothes. First his shoes and socks followed by his shirt. Then his jeans came off. Amy was now sitting down pretty amused by the entire show. Making him strip while she remained completely clothed was a good deal of fun. Jake paused for a min with his jeans off hesitating to remove his boxers.

Amy: Take them off sweetie. You can wear boxers with tights.

Jake turned around and pulled his underwear off. Grabbed the tights and slid them up his legs hoping Amy wouldn’t say anything. Surprisingly she didn’t. He continued putting on the outfit until it was complete. Finally turning around and looking in the mirror he actually thought he looked pretty good. He could have some fun with this outfit. Slightly embarrassing, but not really on a day where other guys would be dressed as cheerleaders.

Jake: How do you like it.

Amy: Its okay I guess. Let me take a few photos so I can make a better decision later.

Amy pulled out her camera and started snapping some photos while putting Jake in various positions, making him flex, and change his facial expressions. She had about 10 different photos when she stopped.

Amy: Okay which outfit do you want to try on next?

Jake: Honestly I think you should just go with the one I am wearing now.

Amy: Nice try! Take it off! And since you hid yourself while putting it on, if you ever want a chance at wearing it over the others you’ll stay completely naked while I do your makeup and turned you into the bitch I know you are.

Jake sighed and started to take the costume off. He was starting to become aroused at this point stripping in front of Amy even though it was pretty embarrassing. Again started with all the other articles of clothing. When he got to the tights he thought about hesitating since he clearly had an erection at this point and was hoping it would quickly go away, but thought better of it and removed them with only hesitating for a brief second. His dick bounced up and down until it settled slightly pointing upward. His penis was average. Nothing to be ashamed about so being naked wasn’t a huge deal.

Amy: That’s a good bitch. I can see you are enjoying this. Now get on your knees in front of me while I do your nails and makeup.

Jake got down on his knees right in front of Amy.

Amy: Hold your hands like this.

She held her hands out with her elbows bent at 90 degrees right at her side with her palms facing downward and her fingers spread apart. Jake did the same learning that failing to comply would only make things worse for him. She pulled out some red nail polish and started doing his nails taking her time to make sure they looked good. The smell was a little unpleasant for Jake but it wasn’t a big deal. Finally after about 15 mins she finished.

Amy: They look great! Red is definitely your color. Remember that one time when we were dating and I asked if I could paint your nails and you said “In your dreams”…… Just letting you know this is the new reality haha.

Jake: I do remember that. Honestly didn’t think I would ever be in this position.

Amy: Keep your hands in this position and close your eyes while I do your makeup. I don’t want you to see yourself till I am completely done. If you open your eyes or move your hands before I finish you’ll be wearing the ballerina costume to school in the morning and change into the school girl outfit in the afternoon. Do you understand?

Jake: Yes I understand.

He quickly closed his eyes and remained that way while Amy started to apply the makeup. It actually felt pretty good having his face hit with brushes and other stuff. Except for around the eyes while Amy was using eyeliner Jake had a hard time not wincing. The entire time Amy didn’t stop commenting on how beautiful he looked and that he should wear makeup more often. She even suggested he could pass as a woman. Jake just remained quiet with his eyes closed. His erection started to go away and was now flaccid again.

Amy: Are you not having as much fun anymore? Does having makeup applied not turn you on? Haha.

Jake: Can’t say it does. How much longer do you have?

Amy: Not much. But you can’t rush beauty. Keep your eyes closed and give me a big smile.

Jake followed her instructions.

Amy: Okay now give me a kissy face. I need to see the makeup looks good in different ways.

Jake continued to do as he was told.

Amy: Okay now point your fingers down and say CHEESE!!!

Jake: WHAT!!!!

He opened his eyes to see Amy taking photos of him naked in full makeup. She quickly ran outside with the camera where Jake didn’t dare follow in his current state. She got in her car and drove off. Jake had no idea what to do. His heart was beating extremely fast and he was sweating even more than the night of the auction. 30 seconds later his phone rang and it was Amy calling. Furious he answered.

Jake: WHAT THE HELL AMY!

Amy: I will give you one chance to lower that voice bitch. Now shut up and listen. Like I said I’ve been planning this for months. And one day of humiliation seemed great, but I figured making you my bitch the rest of the year sounded a lot better. Now I am on my way to give Sarah the memory card with the photos of you. She helped me plan this entire thing. Then I will be back to continue with the fun I have planned. Be a good little boy and put on the thong and bra I have laid out for you. Paint your toenails while you are at it. I’ll be back in 20 mins to explain how the rest of your senior year is going to go. Bye!

Jake: WAIT!

She hung up before Jake could get a word in. He thought this couldn’t be happening. He was so focused on his chance to pick the outfit he wore, and now he was at Amy’s mercy for the rest of the year. Not to mention Sarah was going to have the photos at her disposal too. She was Amy’s best friend. The two were inseparable. They had known each other since the 3rd grade and did everything together. Sarah too was in the band. She was a little better looking than Amy and a little more popular as well. She usually would be the one who got invited to parties and then would bring Amy along with her. Most of the time guys would hit on her before paying more attention to Amy. Sarah actually introduced Amy and Jake at a party before they started dating. Once he asked her to be his girlfriend Sarah made it clear if he every hurt Amy there would be hell to pay. And looks like she was about to keep good on her promise. Jake started running through the options in his head, but quickly realized he had none. Amy could destroy his reputation and make high school brutal for him. Even to suffer for a year in private would be better than the aftermath of having those photos spread around the school.

[deltavoyager]

Good so far!

Cant wait til the next chapters!

[viterz72]

Chapter 3
In utter defeat Jake walked over to the thong and bra. He held each one of them up examining them thinking about how ridiculous he will look once he puts them on. He started with the thong. It hugged his package and he had to figure out how to comfortably place his balls in them. Next was the bra. It was a bit of a struggle to hook the clasps together. After a few minutes he turned the bra around to connect everything before maneuvering it back around and up over his shoulders. Taking a look in the mirror it was even worse than he imagined. His butt popped in it, and being rather slim he looked pretty feminine. The makeup didn’t help matters. After being in shock for a few minutes starring at the mirror he snapped back to reality and realized he still had his toe nails to paint. Grabbing the bottle of nail polish he put a coat on each foot. It was a struggle with his hands shaking from the nerves and embarrassment, but got it done right as Amy was pulling back up to the house. He didn’t know what to do as she was walking back up the sidewalk. Sitting down felt weird, but just standing there was also awkward. He moved over to the adjacent room out of view from the doorway in case someone outside was looking as the door opened. As Amy closed the door he poked his head back around the corner of the wall and slowly stepped out looking down at Amy’s feet.

Amy: OH MY GODDDDD!!!!!! THAT LOOKS SOOOOO GOOD ON YOU!

Amy could hardly contain her excitement. She was even turning red in embarrassment for him. Starting to laugh she could barely get any words out between chuckles.

Amy: Well don’t just stand there. Give me a little spin.

Jake put his arms out to the side and and spun around for her, still unable to look her in the eye.

Amy: Lovely. I was gonna have you cover up with the school girl outfit when I got back, but that ass needs to stay on display haha.

She walked over to her bed and grabbed the wig and heels.

Amy: Put these on

Handing the heels and wig over to Jake he took them and started doing as he was told. The wig was difficult to fix in the right position so Amy assisted with that.

Jake: What now?

Amy: Now the real fun begins. I want more photos of course. Here are the poses you need to do.

She handed him a folded up piece of paper. When he opened it there had to be 20 different poses a model did in lingerie

Amy: Lets go! And I want your facial expression to match the model’s for each pose

Jake was mortified. This was going to get worse and worse if she ever decided to expose him she would have an endless supply of blackmail. He was on the verge of tears, but started doing the poses. The first one was simple with one hand on his hip and the other making a peace sign with a big smile on his face. By the fourth pose Jake was on his knees, turned around, and looking over his back shoulder making a pouting face. Finally he got to the last pose where he was on his hands and knees slightly upright with an arched back deviously looking directly at the camera with a little smirk. He wanted to die inside as Amy took about 15 photos of that pose alone from different angles.

Amy: Perfect! These would look so great on the bulletin board at school.

Jake: Please don’t.

Amy: Haha don’t worry. As long as you do what I want when I want I’ll keep them to myself…. Well myself and Sarah. I wouldn’t want to ruin all the fun just yet.

Jake: How do I know you won’t show everyone the photos at the end of the year even if I do everything you say?

Amy: Haha you don’t. But what you do know is these will be seen by everyone on Monday if you disobey. I would be disappointed to end our fun so quickly, but I promise you I would rather expose you tomorrow than only get partial control of you the rest of the year. If you think I am bluffing you know Sarah would pull the trigger and share these with everyone. Now lets go over how the rest of this year is going to work.

[viterz72]

Chapter 4
Amy set the camera down and went to grab a bag out from under her bed. Jake watched as she ruffled through it searching for something.

Amy: Ahhh here it is.

From Jake’s perspective she held up what appeared to be a small penis with straps attached to it, but couldn’t really make out exactly what it was.

Jake: What is that?

Amy: It’s called a penis gag.

Jake: What the hell is a penis gag?

Amy: Open wide and find out haha.

Jake: No you’re not putting that in my mouth.

Amy: It’s funny how you think you still have a choice. Maybe I have to share those photos with someone other than Sarah to show you I’m serious.

Amy looked into Jake’s eyes and he knew she meant it. He opened his mouth slightly as a gesture to let her know he would comply. Amy abruptly and aggressively stuck the gag in his mouth fastened the buckle around the back of his neck and placed a tiny lock on it.

Amy: Now that’s a good boy. Better get use to it. That gag will be worn regularly and you will have plenty of other penis shaped objects in your mouth in the near future…. But I am open to changing my mind on that. Just tell me right now if you don’t want to become an expert dick sucker and I wont make you.

Jake desperately tried to say something. But could only get out muffles.

Amy: Well alright if you don’t mind I’ll have you deep throating like a pro in no time haha. Remember when you would complain I didn’t go deeper when giving you a blowjob? Because I sure do and now I think it’s only right you get to experience what it’s like haha….. Anyway I don’t want to be interrupted by your complaining while I go over everything so keep those muffles to yourself. Also why don’t you get on your knees and massage my feet while I go over everything.

Amy sat on the bed and stuck her feet out. Jake proceeded to get on his knees in front of her and removed her socks and shoes. He slowly started massaging her feet while fixated on every word coming out of her mouth.

Amy: So once this school year is over I will let this go and you can go on to college having learned your lesson. That is pretty far away, but just wanted to let you know there is an end for you. Until then you will do everything I tell you without hesitation. Failure to comply with an order I give you, will result in a punishment and if I feel you are not doing well I will start to inform other people about this until you are the laughing stock of the entire school. Also I will be sharing the photos and other material with your family if you don’t comply. I’m sure you could only imagine what your mom and dad would think. Obviously you wont be able to come over everyday, but my parents leave every weekend and have a date night every Tuesday. Sarah’s parents volunteer on Thursday nights so we will be going there after school on those days. Besides doing everything I say you will have a set of rules to follow. I wrote them down so there is no question as to what the expectation is. There will be more added but I don’t want to ruin a few surprises haha.

Amy pulled another folded up piece of paper out of her pocket and handed it out to Jake. He stopped massaging her feet and opened the paper to read it.

Rule #1: You are to wear women’s underwear at all times. You need to buy more or wear the only pair you have now everyday. The choice is yours.

Rule #2: You must always refer to me as Goddess, Princess, or Your Majesty when we are not in public.

Rule #3: You are to wear a shocking dog collar at all times when coming over. The Collar must be on before entering the house.

Rule #4: You must sit down to pee.

Rule #5: You must do a striptease every time you come over immediately when you enter through the door way. Have a song ready to play on your phone.

Rule #6: You will practice giving a blowjob on a dildo for 10 mins a day. On days we cannot meet you will record the act and save it on a hard drive.

Rule #7: Any instruction given by me or Sarah must be done without hesitation.

Jake finished reading the rules and looked down beaten by what he just learned. He was trapped with no escape. Amy pulled out the shocking collar from the bag that she got the penis gag from and placed it around Jake’s neck. She pulled out the controller.

Amy: This has a range from 1 to 99. I have tested it on myself but only went to 25. Let’s see what 30 feels like.

She set the controller to 30. Stared Jake directly in the eyes and pushed the button. He jumped a little but could handle that setting without too much difficulty. It was just more of an unusual feeling that caused him to jump. Amy moved the setting up to 50 and hit the button again causing Jake to moan through the gag.

Amy: This is fun. Do you think we should try 70?

Jake shock his head no and Amy sent another zap at 50.

Amy: Do you think we should try 75?

Again Jake shook his head no and Amy hit him again with another shock.

Amy: Do you think we should try 80?

This time Jake took a breath an nodded.

Amy: Well if that is what you want then I guess I will do things your way just this once.

She set the controller to 80, got right in his face, smiled, and pushed the button hitting him with another shock. Jake moaned even louder this time. His head jolted in the opposite direction of the shock and his body tensed up in the process.

Amy: That was fun. I will move it back down to 50 as nice as I am and every time you make me mad I will increase the number. Now I’m getting pretty hungry. Go make me a sandwich and cut the crust off. There is lunch meat in the fridge.

Jake was hungry himself but could not ask for anything with the gag in. He got up and walked to the kitchen with his heels clanking on the floor. Half way there Amy hit the button on the shock collar again causing Jake to stumble to his knees. She chuckled as he got up and continued to the kitchen. Once there he made a ham and cheese sandwich for her with lettuce, tomato, and mayo. He cut the crust off as instructed and cut the sandwich diagonally. He grabbed a bottle of water as well and walked back out to the living room where Amy was now relaxing and watching TV. He placed the sandwich and water on the coffee table in front of her and stood back not knowing if he was allowed to sit on the couch or what he should do as she was not looking at him in the slightest.

Amy: move the coffee table over. You will hold the plate with one hand and the water in the other on your knees in front of me until I am done eating. You can’t possibly think I can be troubled to reach all the way to the table every time I want to take a bite or have a drink.

Jake did as instructed so that Amy could enjoy her show while comfortably leaning back. She took her time eating not paying any attention to Jake and finished the sandwich in about 15 mins.

Amy: Thanks Bitch. Now put the dish in the kitchen and throw this bottle away. Then come back and be my foot rest while I finish my show.

Jake went back to the kitchen to take care of his task. Again on the way Amy sent him another shock. This time he pause but was able to keep from falling over. He came back and got on his hands and knees acting as a stool so Amy could put her feet up. There was about 20 mins left in the show as he started to wonder when he was going to eat. He could hear his stomach growling and he new she could hear it too.

[BB88]

Wow Please continue this is hot