Ex Girlfriend Shows No Mercy
 

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.

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.

Good so far!

Cant wait til the next chapters!

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.

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.

Wow Please continue this is hot

I second this. I'd love to read more

Chapter 5

Finally the show ended which seemed like an hour to Jake even through it was truly only 20 mins. His knees were starting to hurt and his back was uncomfortable. Amy turned off the TV and got up. Jake remained in place not knowing if he was allowed to move or not just keeping his head down looking at the floor.

Amy: Are you hungry?

Jake nodded his head still unable to speak with the gag in his mouth.

Amy: Alright. Stay put while I get your food.

Amy walked grabbed a dog bowl from the kitchen and placed it in front of Jake.

Amy: I got this bowl special for you. All your meals will be eaten from the floor like the bitch you are. Now sometimes I will let you eat what I eat but right now I think it would be more fun to watch you eat some wet dog food I bought haha.

She grabbed a huge can of dog food and opened it up in front of Jake making him smell it.

Amy: Yum! Chicken, Beef, and Liver. You’re one lucky dog.

She turned the can over and hit the back to get the contents in the bowl. Everything stayed together mushed in one big glob still in the shape of the can as it landed in the bowl. It made a suction sound coming out of the can as well.

Amy: OH MY GOD!!! this is going to be hilarious watching you consume this. There will be a punishment if you do not eat the entire thing which shouldn’t be a problem since I know you are hungry haha. Let me get the camera set up and I will unlock the gag for you.

Amy set the camera up so that Jake was in full view of the camera from where the bowl was to his heels. She then took the lock off of his penis gag and unbuckled it. Drool built up from the gag dripped onto the floor as Jake moved his jaw around. It was pretty stiff being in an open position for so long.

Amy: You’re drooling. You must really be looking forward to this meal I made for you. Now I still don’t want to hear you talking. Dogs can only bark. So now one bark means “No”, two barks means “Yes”, and three barks are required if you need to ask for permission to say something…. Do you understand?

Jake: Woof! Woof!

Amy: Oh that was lovely. Good now just one more thing before you eat your lunch.

Amy walked over to the camera and hit record. Then she spit on the dog food Jake was about to eat followed by sticking her bare foot in it to mashed it up from the can shape it was still in.

Amy: For an appetizer you can lick my foot clean. Make sure you get in between my toes.

Jake looked up at her starring down at him with a huge grin on her face. This was disgusting and he wasn’t even hungry anymore. Never the less he proceeded to clean her foot off with his mouth and tongue making sure he got between her toes as instructed. After about 5 mins Amy stopped him.

Amy: Alright that’s good. Now I don’t want to wait all day for you to finish your lunch so I am putting you on a 10 minute timer. If that bowl is not spotless by then you will be going for a walk around the block on a leash in your current attire. Ready! Set! Go!

Jake wasted no time and dove right into the meal. The taste wasn’t so awful but the texture was making him gag. To make matters worse Amy never gave him any water to with his meal, but he couldn’t ask for any so he just powered through it.

Amy: 5 minutes

Jake was 3/4 of the way done, but kept going at the pace he was at making sure he didn’t cut it close. At 8 minutes he had finished all the food and started licking the bowl clean. With a full minute to spare he was done. Amy stopped the recording.

Amy: Wow that was fun. I had no idea if you were going to be able to complete that or not. I don’t even care that it messed up your lipstick. We can take care of that shortly. Now clean all of this up and then meet me in the bed room.

Jake: Woof Woof Woof!

Amy: Hmmm since you did a good job I will let you speak. What is it?

Jake: May I please have some water princess?

Amy: You may grab a bottle from the kitchen as you are cleaning all of this up. Now get to it!

Amy went to the bedroom and left Jake to take care of the mess. He took the bowl to the kitchen to wash it along with Amy’s dish and threw away the empty can. He was so thirsty as soon as he made it to the kitchen he chugged an entire bottle of water before starting to wash everything. He figured he might as well take his time. Doing dishes was better than anything else Amy had up her sleeve. As he was setting the dishes down to dry. ZAP! He got shocked again. Then Amy came around the corner.

Amy: What is taking so long?

Jake: I’m sorry I was just trying to do a thorough job.

Amy: Did I say you could speak?

Jake: Errr no but I assumed when you asked a question I could answer.

Amy: WRONG!

ZAP! ZAP! She turned the controller up to 60.

Amy: That is one for speaking and another for failing to address me properly. Now here is a list of chores I need you to do.

She handed him the list.

Amy: But first lets fix your makeup. Sarah will be coming over for dinner and I want you to look perfect for her.

Amy removed the smeared lipstick from Jake’s mouth and touched it back up.

Amy: Good as new. Now get started and I don’t want to be bothered.

Amy went to her room again to relax and listen to music. Jake proceeded to start on the list which consisted of the following…

- Vacuum the floors
- Sweep and mop the kitchen
- Dust the shelves
- Clean the bathrooms
- Wash my car

How was he supposed to wash her car in his current state he thought. She had to be messing with him. She had neighbors that would definitely notice by the time he finished washing it. Also he wasn’t suppose to bother her. Jake started on the other chores while thinking about how he should go about the last one

Chapter 6

While working on the other chores Jake decided his best chance was to ask if Amy could pull the car in the garage and then he could wash it inside. There was a drain in the garage so it wouldn’t really be a problem. He figured he had nothing to lose by asking. It was unlikely she could make it any worse. It was about 6pm when Jake had finally finished all of the chores except for washing the car. His feet were absolutely killing him from the heels. He had a new respect for women wearing those on a night out or just in general. He was starting to get use to the thong and bra though. At first it felt super weird but gradually was growing on him. Even though he had time to go over everything in his head on how to ask Amy if she could pull the car in, Jake still was a little sick worrying about what he might be in for if she said no. He even had some suggestions prepared of alternatives he would be willing to do instead of washing the car outside. We walked into Amy’s room where she was relaxing and watching TV.

Jake: Woof Woof Woof!

Amy: Are you all done with the chores? You may speak freely again until I say otherwise.

Jake: Thank you Princess. Yes I am done with everything except for washing the car. I was wondering if there was any way you could pull the car in so that I could wash it in the garage?

Amy: What is wrong with outside? I think the neighbors would enjoy the show! Don’t you think?

Jake: Please princess I can’t be seen outside like this.

Amy: Hmmmm well here is the deal. I am not going to pull the car in the garage. But if you want to pull it in before you start washing it then I will allow it. I’m just so nice aren’t I?

Jake: Yes super nice Princess.

Amy: Alright well here are the keys. The offer expires in 5 mins.

Amy threw Jake the keys while again thoroughly amused by his predicament. Jake caught them and hurried over to the window to see if anyone was outside. Amy lived on a street that wasn’t always busy. It was off a main road and could see cars very frequently or only every 10 mins. None of her neighbors were out except for a mom walking her dog. The dog was going to the bathroom in the yard next to Amy’s. Jake hoped she would hurry up. The car was in the middle of a 40 ft drive way and could easily be seen by all the houses across the street and on the sides. There were probably 20 houses that could be a problem for him.

Amy: 4 mins

Jake thought about the best way to get to the car without being seen. If he went out the front door he was more exposed but could get to the car before making much noise. If he went out the garage he was less visible to start but opening the garage would draw attention to him before he was in the security of the car.

Amy: 3 mins

He finally decided on going through the garage. It was closer and a little less visible to everyone. He also re-positioned the wig so that his face was more covered up. Finally the mom and her dog had moved on down the street.

Amy: 2 mins

Jake figured now was as good a time as any. He opened the garage door and peaked out. The coast was clear. He had the key to unlock the door in his hand. Amy stood in the living room and watched as he was potentially exposing himself to everyone on the block. Jake booked it for the car. Well as fast as he could go in the heels. As he reached the drivers door Amy had hit the button on her spare set of keys setting off the car alarm. Then she proceeded to hit the garage door button making the door close. To top it all off she got the shocking dog caller remote and started shocking Jake every few seconds making him stumble and fumble the keys. He dropped them on the ground and quickly picked them up but couldn’t get the car alarm to stop while hitting every button. To make matters worse his wig fell off as he as on the ground grabbing the keys. Finally after hitting every button at least 3 times the alarm shut off. Still in a panic he unlocked the car door and got in. He took off the collar as Amy was still giving him shocks. There was a garage door opener in the car thankfully that he used to reopen the door and pull in. He stayed hunched down the entire time barely peeking his head over the steering wheel not daring to even look around and see if anyone was watching. Finally after what seemed like an hour he pulled into the garage and closed the door. Amy was unable to speak from laughing so hard as she made her way to the garage to greet him. Jake got out of the car furious and beat red from embarrassment and panic.

Amy: OH MY GOD THAT WAS PERFECT!!! You should’ve seen your face when that car alarm went off. Luckily you can because it is all on film. Not sure if you noticed but I saw at least two people look out their windows as you were in that little predicament.

Amy wiped some tears from her eyes from laughing. Jake just stood there waiting for her to compose herself. After a few more minutes Amy calmed down.

Amy: Alright well you better get started. I want it cleaned inside and out. And if that shock collar isn’t back around your neck in 1 min its getting secured to your balls next. I’ll go get the wig for you. You’re so clumsy I hope you know that haha.

Jake knew he was still trapped and couldn’t even say shit back. He grabbed the collar he took off and put it back on. He grabbed a bucket and got to work starting with the outside of the car. Amy returned with the wig shortly after he started. It took longer cleaning it inside the garage without a hose but was still the better option than being outside. The outside of the car took about 40 mins and then he got to work vacuuming and cleaning the inside. The entire time Amy took more photos and videos just adding to her collection. As Jake was finishing the car up the door bell rang.

Amy: That must be Sarah!!! Oh she is just going to love seeing you in person. I have been messaging her updates all day. Why don’t you go an answer the door.

Jake looked her in the eyes as she was grinning with that smirk that sent shivers down his spine.

Jake: As you wish Princess

Jake walked over to the front door, looked back at Amy standing there with the camera still, and took a deep sigh. He opened the door slowly unlocking the dead bolt first and then the door handle. He positioned himself so that as he opened the door his body couldn’t be seen by anyone outside. Just his face and shoulder was exposed. To Jake’s surprise it wasn’t Sarah. It was a pizza delivery driver. She had to be around his age. She was short but cute.

Jake: Oh sorry one sec

Jake closed the door quickly.

Jake: Amy that isn’t Sarah

Amy: I know silly. Sarah wont be here for another 30 mins. Now pay the lady and make sure she gets a good look at your entire outfit.

Amy handed Jake a $20 dollar bill.

Jake: Come on don’t you think I’ve had enough for one day.

Amy: Nope! And if you keep hesitating I’ll invite her inside when I answer the door.

Jake moved back to the door with the $20. Opened the door again this time as he normally would if he was completely dressed.

Jake: Sorry about that I had to grab the cash

Pizza girl: Oh that’s alright. You look great by the way. Can't wait to tell everyone back at the shop about this one.

She was trying to keep herself from laughing as she took the money from Jake.

Jake: You can keep the change. Have a good night!

Jake quickly closed the door. Hoping he was done with being exposed to random strangers for the day. He set the pizza on the dining room table.

Jake: May I sit Princess?

Amy: You may for now. I will let you relax and have some normal food. You’ll need your strength when Sarah gets here. I can’t have you worn out already. The fun has only started. Just think this morning you were just a normal senior in high school. And now…. Well I don’t really know what to even say at this point. This has been the best day of my life!!!

Chapter 7

Jake thought about what Amy just said and started going over how much everything had changed in a day. He was her bitch and Sarah would likely be even more cruel based on her personality. He still had Monday to worry about. He would have to do everything Amy said in front of the entire school and didn’t know how far she would push things. He thought about how he could possibly get out of this situation but quickly realized it was useless. He had the rest of the year to get through and then could put this behind him. After finishing a few slices of Pizza the door bell rang again.

Amy: Go answer the door. I promise it is Sarah this time haha.

Jake: As you wish Princess.

Jake got up to answer the door. This time he didn’t dare hide his body when opening the door. He knew at this point it would only make things worse. As he opened the door he saw Sarah’s eyes light up like she had just received the greatest present in the world. She stepped in and closed the door.

Sarah: Looking good Jake! But I am not sure we can keep calling you Jake the way you look now. How does Jessica sound to you.

Jake: Not sure I like the sound of that to be honest.

Sarah: Well it is either “Jessica” or “Dick Sucker”. I’ll let you pick what you want to be called.

Jake: Jessica sounds fine.

Sarah: Good! Now Jessica I wasn’t lying when I said you look good. However ladies can’t have all that nasty body hair.

Jake: Please no. I can’t lose my body hair.

Sarah: Sure you can. You’ll look hot! Haha!

Jake: Please! Please! Please!

Sarah: Do you have that penis gag Amy?

Amy: Of course he was wearing it all morning.

Sarah: I think it is time that dick is put back in his mouth.

Amy: Yes I totally agree.

They spoke like he wasn’t even in the room. Amy grabbed the gag and put it back in Jake’s mouth.

Sarah: Let’s restrain him while we decide how to remove his body hair.

Amy led Jake downstairs to a home gym her family used. She had him stand on a bench and proceeded to hand cuff his hands around a pull up bar.

Amy: That should hold him. Now how should we go about this?

Sarah: Lets remove what little clothing he has on and discuss.

Sarah immediately pulled down the thong Jake had on, exposing his erected penis. Even through all the embarrassment he could help but be turned on being restrained by two girls.

Sarah: Not too bad Jessica. It could definitely be bigger though.

Amy: I agree. I enjoyed it but defiantly left me unsatisfied at times.

Amy removed the bra. They decided to keep the heels on as well as the wig.

Sarah: So we have two options. We can either shave everything or use the wax strips I brought.

Amy: Wax strips sound a lot more fun.

Jake muffled through the gag.

Amy: Sorry is there something you want to say?

Jake nodded his head up and down.

Sarah: That’s a shame.

Sarah pulled out the wax strips and placed one on each of Jake’s thighs. They were Nair wax strips and when a strip was pulled apart it created two strips that could be applied to someone.

Sarah: Let’s do the first ones together Amy.

Amy: Great idea Sarah. It’s nice getting to have this fun with you.

Each of the girls got a firm grasp on the wax strips applied to Jake’s thighs.

Amy: Are you ready?

Sarah: Yeah on “3”….. “1”…..”2”

Sarah ripped her wax strip off.

Sarah: “3”

Amy ripped her wax strip off.

Sarah: That was awesome! Who got more hair?

Amy: I think there is a little more on yours.

Sarah: Oh my god. Feel how smooth it is where we removed the hair.

Amy and Sarah rubbed Jake’s legs were they had removed the hair. Jake stood there in pain. It was hard to relieve the pain when they pulled the strips off not being able to yell at all with the gag.

Sarah: 2 down about a 100 more to go haha.

Amy: We got time.

They continued waxing Jake until all his body hair from his neck down was gone. It took about two hours. He was absolutely exhausted from the pain and being restrained. They took the heels off before undoing the hand cuffs so he wouldn't fall getting down off the bench. Jake stumbled getting down.

Amy: Don’t worry. As long as you continue to shave yourself we wont have to wax you again haha.

Sarah: What else do you want to do with him tonight.

Amy: Well I am a stickler for rules and he hasn’t complied with #6 yet today. Once he is done with that I think we will give him the rest of the night off.

Sarah: That sounds like a good plan to me.

I'd love to read more of this!!

Sorry it’s been a while. Still working on another update but should have something for everyone in the next week or so.

Chapter 8

Sarah: I think that is fair. Even though we don’t have to be fair. I want him somewhat rested for tomorrow. I missed most of the fun today. Where is the dildo for him to suck on?

Amy: I have a few upstairs. Lets go pick one out.

Amy and Sarah went upstairs to figure out which dildo they wanted to use. Jake laid on the workout bench ready to pass out. His body was pretty raw from being waxed and needed some recovery time. He was about to fall asleep when he heard Sarah and Amy coming back down the stairs. He looked up as they got to the bottom of the steps. Both of them were wearing strapons. Amy’s was a purple dildo that was thicker but only about 5 inches long. Sarah’s was pink and thinner but at least 7 inches long.

Sarah: Awe look how cute he is without any body hair.

Amy: Yeah I will admit he looks pretty cute. Cute like a cheerleader that is haha.

Sarah: Yeah let’s keep him naked for this next task. I bet he gets aroused sucking on our cocks.

Amy: I wouldn’t be surprised…. Come on Jessica get on your knees in front of us.

Still exhausted Jake got up and then down on his knees in front of the two girls staring those dildos right in the face. He looked up at Amy’s eyes hoping for some sympathy. Wearing women’s clothes was one thing but actually having to suck on a dildo was mortifying. He wasn’t aroused at all. Amy undid Jake’s gag. Jake looked down not wanting to start the task any time soon. Amy put her hand on Jake’s chin and made him look back in her eyes.

Amy: So to be clear the rule is that you will practice giving a blowjob for 10 mins a day. Simply putting your mouth around the dildo doesn’t count. I have a stopwatch and at any time you are not giving full effort I will stop the time. If you are giving 95% effort the time stops. However you will not know when I start and stop the time. Until I say you are done you have to keep going. If you stop before the 10 mins except for occasional breaths you won’t like the punishment.

Sarah: Nicely put Amy. One more thing before we get started.

Sarah went back up the stairs and returned a few mins later with the camera.

Sarah: We almost forgot to record this in all the excitement Amy.

Amy: Your right that would have been tragic…. We can show how his skills progress over time haha.

Sarah: Now Jake I know you might have a hard time choosing which cock you want to suck more, but we expect roughly equal time on both.

With that Sarah hit record on the camera. Amy and Sarah then proceeded to grab their their dildos and rub them on Jake’s face. As he winced and clinched his teeth the girls just chuckled.

Amy: Timer still says zero. You must want to spend a lot of time on your knees with these in your face.

Finally Jake opened his mouth and started sucking on Amy’s dildo. He went pretty slow barely taking two inches in his mouth to start. Amy decided to give him a little more encouragement by grabbing the back of his head and forcing the dildo deeper in his mouth eventually hitting the back of his throat as he resisted. Immediately Jake pulled away gasping for air and choking with tears in his eyes.

Amy: Awe don’t you remember when I told you I was going to make you experience what deep throating was like? How was it?

Jake just continued trying to get his breath.

Amy: By the way you still got 9 mins and 55 seconds to go. However I think we will just work on your gag reflex instead of watching your pathetic attempt at a blowjob for the next hour. I thought you would be better at this haha.

Sarah: Ok that’s enough breathing. My cock needs some attention.

Sarah placed her dildo in Jake’s mouth. Similar to Amy she thrusted and grabbed the back of his head until again he forced himself away and was chocking.

Amy: I got a better idea.

Amy walked Jake over to a structural pole in the middle of the room. Then she hand cuffed his hands and bound his back around the pole and secured his legs as well so that he was on his knees and could not pull away. Then she grabbed a ring gag and placed it in his mouth to keep it wide open. Sarah was still recording.

Amy: Alright that’s better. Now let’s see how far we can push you. Relax I will be gentle.

Jake nodded letting her know he understood.

Amy: Let’s go for 5 seconds at a time to start. I will slowly insert the dildo. You need to relax your throat and body and take it.

Amy proceeded to slowly insert the dildo in Jake’s mouth. She stopped before it reached the back of his throat, waited for 5 secs, and then pulled it out.

Amy: See that wasn’t so bad….. Lets go again.

After a few more times of the same thing she pushed the dildo in a little further and repeated this process while also increasing the time until Jake was able to take the entire dildo in his mouth for 10 seconds without failing.

Sarah: Ok I think it is my turn. Let’s see if he can take this longer one haha.

Amy: Yeah I would say I have been gentle with him so far haha. Give me the camera.

Sarah handed Amy the camera.

Sarah: If you don’t want this dildo in your mouth just say so and we can untie you.

With the ring gag in Jake just looked down and shook his head left and right.

Sarah: Sounds like you want it.

Sarah took the dildo and inserted it in his mouth. Slowly she kept pushing it in. However the 5 inch dildo didn’t go down his throat it just hit the back of it. The 7 inch dildo started going down his throat as Sarah continued to push in. Jake tried to relax but it was too much to handle. He started choking and Sarah pulled out causing Jake to puke all over Sarah’s feet and the floor.

Good next chapter. Looking forward to me

Asdf
 

Can't wait to see if and how he's punished

Chapter 9

Sarah: Uhhh this is disgusting.

Amy: Better you than me Sarah. Haha it looked really good on camera though.

Sarah: I am going to go clean myself up. Untie this bitch and make him clean this all up.

Sarah left to go wash up. Amy proceeded to untie Jake who was still coughing and trying to regain control of himself. Once untied he drank some water and composed himself. As he was cleaning up Sarah came back from washing up.
Looking at him with disgust, Jake turned to her.

Jake: Sorry about that.

Sarah: Oh it’s fine. Knowing how the rest of tonight is going to be for you makes me a lot less mad…. Amy can you give me a hand while Jessica finishes cleaning this up.

Amy: Yeah no problem

The girls left and went upstairs leaving Jake to clean up the mess. He thought about what they could possibly do to make the night any worse. Just staying awake would be bad enough. His body had been pushed pretty far throughout the day. Finally when he was done he walked back upstairs to meet up with the Amy and Sarah. As he got to Amy’s room he was again in disbelief by what he saw. The girls were putting a dog cage together. He knew it was for him, but still couldn’t help asking.

Jake: What is that for?

Sarah: It is where you are sleeping tonight silly.

Amy: Yeah Sarah wanted to get a smaller cage for you but I thought that was a little too mean so I insisted we get one made for a large dog.

Sarah: Yes after talking with Amy about this idea we agreed you should be more comfy in this one. We need you well rested of course. Aren’t we the sweetest.

Jake didn’t respond and Sarah zapped him with the dog collar.

Sarah: I said aren’t we the sweetest?

Jake: Yes both of you are very sweet and kind.

Sarah: That’s better. Now since you puked on me earlier any time I wake up throughout the night you will get shocked for my amusement haha. Just thought you should be aware. Now put this on and let’s get you in the cage. It will be locked so you can’t sneak out during the night.

Sarah handed Jake an adult diaper. He took it and tried to put it on but was struggling some with the straps trying to put them on while standing up.

Amy: I think he needs our help Sarah.

Sarah: Haha I think your right. Lay down on the bed Jessica.

Jake did as he was told once again learning that it was best to do everything he was told without question or hesitation. Once the diaper was on he crawled into the cage and Amy put a lock on the door.

Sarah: Sleep tight. And keep quite until we open the cage in the morning. Before then you are not allow to speak.

Jake closed his eyes and tried to get comfortable enough to fall asleep. Even though it was a little cramped being as tired as he was he thought it wouldn’t be long before he fell asleep. Sarah zapped him a few times just for the fun of it and giggled.

Sarah: Couldn’t help myself haha.

Jake didn’t respond knowing he wasn’t allowed to speak. He drifted off to sleep pretty quickly. Sarah only shocked him one time when she woke up in the middle of the night. Jake woke up and wanted to stretch but couldn’t. Took about an hour for him to fall back asleep but eventually he did. It wasn’t till morning when he woke up again from another shock. At this point he really had to pee and hoped he would be let out.

Sarah: Morning dumbass. Get your ass up and make me and Amy some breakfast. We want pancakes, eggs, and bacon with hash browns.

Jake: Can I please go to the bathroom first?

Sarah: You may but put this on and the heels you were wearing yesterday before you start cooking. We want you presentable while serving us haha.

Sarah handed Jake a slutty maid costume with all the extras including a wig. It had garter straps and fishnet thigh highs. Jake took the outfit and left to go relieve himself in the bathroom. He got ready as he was told to before starting to make breakfast. He was starting to get more use to wearing feminine clothing. The heels still hurt but were starting to get more conformed to his feet.

Amy: Hurry up already we are hungry!

Amy yelled from her bedroom.

Jake: I will be there in one minute!

Jake yelled back and quickly got their food on plates. He rushed back to the room but didn’t move too quickly so that he did not trip. He didn’t want to think what would happen if he ruined their breakfast.

Jake: Here you are Princess and Princess.

Sarah: How are we supposed to eat without silverware or drinks idiot!?

Jake: Sorry mama I will be right back.

Jake hurried back to the kitchen and poured each of them a glass of orange juice and grabbed some silverware. Once back at the room he handed them the silverware but realized there was no place for them to set their drinks while in bed. He stood there in confusion. Amy realized he didn’t know what to do with the drinks.

Amy: You can just hold those and hand them to us as needed. You look great by the way. Except I think you need some lipstick. Go put on that red lipstick that’s on my dresser.

Jake went to go put on the lipstick. He took his time applying it in the mirror to not screw it up. As he was doing so his ass was sticking out in perfect view for Amy and Sarah. Once applied he turned back around and continued to hold their drinks as they ate breakfast.

Amy: Much better.

As Amy and Sarah were finishing up their breakfast the doorbell rang. Each of them looked at each other with giggles of excitement. Jake started instantly sweating looking at their excitement not knowing what they had planned.

This is pretty good. I wonder who's at the door...

omg i am hooked!

I should have an update for everyone this weekend.

patiently waiting......

I wrote the next chapter but have been back and forth on if I want to change the direction on it. Traveling really right now but will be able to review at the end of the week and post an update

At
 

Still waiting lol

Who was at the door?

Cant wait for the next part!

I’m kind of hoping a girl he has a crush on answers the door or maybe his little sister or something 😂

So far so good. Why hasn't Amy locked him in chastity, because she surely can?

Ah
 

Or her new bf would be interesting...or his bully

Chapter 10

Amy: You think our special guest is here already?

Sarah: Haha I guess so. I cannot wait to see her reaction when she sees Jessica.

Amy: Hurry Jessica you can’t keep our special guest waiting.

Sarah: She is going to love your outfit haha.

Jake looked down to the ground and proceeded to the front door. Amy and Sarah hopped out of bed to follow and watch the scene unfold. As Jake was approaching the door he remembered from before not to hide when answering. However, he did step more to the side so that only the person at the door could see him and not all the neighbors if anyone else was outside. His heart was pounding and hands were almost dripping with sweat as he saw who it was.

Ashley: Hey Jake! Looking good!

Jake just stood there unable to speak. It was the girl who he had been talking to for the last month. They had only been on one date last weekend and things seemed to be going pretty well.

Jake: Wh-Wh-Wh-What are you doing here?

Ashley: Amy saw the photo I posted of us on our date last week and messaged me. Told me all about why you broke up and what she had planned. I thought it would be fun to come see it for myself haha. I honestly didn’t believe she would take it this far, but I am glad to she she has.

Jake just continued to stand there shocked at who he was looking at.

Ashley: Well aren’t you going to invite me in?

Jake: Uhh yeah sorry please come in.

Ashley entered the front door with a duffle bag and Jake coming to his senses quickly closed it realizing he was in a position where people outside could potentially see him.

Amy: Glad you could make it! So what do you think of our little bitch Jessica? Haha.

Ashley: He looks adorable haha. I brought a few outfits and other things we can use on him.

Sarah: Do you want to see the photos and videos we have taken so far?

Ashley: Yeah lets go through them. But first “Jessica”? Is that what we are calling him?

Amy: Yeah we felt like if suited him much better. Don’t you think?

Ashley: Can’t say I disagree haha.

Amy: Jessica go and get the camera. Set it up so we can view it on the TV. While she is doing that we can look at what you brought Ashley.

Jake was pretty upset at the current situation. A tear rolled down his face as he was getting the camera, but he quickly composed himself so that the girls would not get to see how miserable he was. The girls continued to talk and go through what Ashley brought as Jake set up the camera filling Ashley in on everything as if Jake wasn’t in the room. They did whisper at times not wanting to let Jake in on exactly what he was in store for. As Jake was finishing up getting the camera hooked up to the TV he was met with a few zaps curtsy of Ashley.

Jake: Ahhh!

Ashley: That was fun! I am going to have a hard time not pushing this button.

Sarah: I know what you mean. It is a lot of fun…. Would you like Jessica to massage your feet as we go through the photos and videos?

Ashley: That would be lovely.

All the girls were sitting on the couch in front of the TV at this point. Ashley stuck out her feet and wiggled them gesturing for Jake to start massaging. Jake walked over handed Amy the camera, and proceeded to take off Ashley’s socks and shoes to start massaging. The girls had a great laugh going through all the photos and videos that they had already taken. Watching Jake deepthroat the night before was the highlight of the footage. They watched it 8 times laughing harder and harder each time.

Zap! Zap!

Ashley: Haha that was pretty interesting. This is going to be a fun day.

Amy: Is there anything you want to see him do for you in person first?

Ashley: Well he looks great, but I would like to see his little friend up close.

Sarah: You heard the lady! Stand up and lift up your skirt for Ashley.

Jake stood up and lifted his skirt as instructed looking straight ahead trying not to make eye contact with Ashley. With a smile Ashley pulled the panties down that Jake was wearing to get a good look. Jake was pretty aroused by the situation. Having a girl looking at his dick that he found attractive made him rock hard even in his current situation.

Ashley: Hmmm it could definitely be bigger.

Amy: I do not disagree.

Sarah: It might be fun to watch him stroke it while wearing that outfit.

Ashley: Do we think he deserves any pleasure?

Amy: I think the video we get is worth a little pleasure for him. It’s not like we need to let him cum haha.

Sarah: Very true.

Amy: Jessica go get some lube from my room.

Jake got up to go get the lube as the girls continued to discuss. He was embarrassed and excited at the same time. It would be nice to get some stress relief but doing so on camera dressed as a woman was not ideal. He figured they already had enough blackmail to ruin his life so any pleasure is better than none. Jake returned with the lube and shrugged his shoulders.

Jake: So how do you want me to do this Princess?

Amy: Take the panties off and get on your knees. You will hold the skirt up with one hand as you jerk with the other. We may or may not let you cum so you need to ask before doing so. Also to make it less pleasurable for you we decided you have to wear a condom.

Ashley handed Jake a condom and he got to work getting in position. Getting the condom on wasn’t too difficult since he was still rock hard. Sarah was recording and the girls would shout out instructions and comments as Jake stroked. “Faster” “Slower” “Stop” “What a little bitch” “Look at the look on his face” and so on. It made it hard to stay focused but after 10 mins Jake was pretty close to cumming and he had to keep slowing down in order not to cum.

Jake: May I cum Princesses?

Ashley: What do you think ladies?

Sarah: I would have to say no.

Jake looked at Amy in desperation hoping she would have a different answer.

Amy: Sorry Jessica maybe some other time. Hands off your dick for now.

Jake stopped stroking. Frustrated and sweating he froze there on his knees.

Amy: Stay there until you are completely soft and then come join us in my room.

The girls got up and left while Jake wondered how long it would be until his erection went away. Right now his dick was throbbing and showed no signs of getting softer. After what seemed like 20 mins his dick was soft again. He got up and met the ladies in Amy’s room.

Jake: Hello Princesses. What is next on the agenda?

Amy: Well it was even more fun seeing you frustrated than we thought. Originally we were going to let cum and make you drink it from the condom, but with the next surprise we have for you I made the decision at the last minute that it would be more fun to hold off on that for now.

Jake: What is the next surprise?

Ashley: Happy you should ask haha. I went shopping yesterday and picked this out for you. Open it up.

Ashley handed Jake a gift bag as the other two girls giggled in anticipation of watching Jake find out what was inside. Jake with a slight hesitation took the bag, reached in, and pulled out a package. His heart sank when he saw what it was. In his hand he was holding a chastity device to lock his dick up. He just stood there speechless letting it sink in.

Ashley: Just so you are aware before we put it on you we have all agreed you will be wearing this 24/7 unless we say otherwise. And so you have something to look forward to, the first time you get released. Which may be in a day, a week, a month, or longer you will be eating every last drop of cum every time you are let out.

Jake felt like he might throw up letting it sink in how rough his life was going to get. Having to swallow his cum was an unimaginable thought by itself. But the situation in front of him was almost unbearable. Jerking off was something he did pretty regularly. Not being able to for a month seemed impossible. However it is not like he had a choice or say in the matter.

Ashley: Now that you know how this is going to work lets get you locked up. Hand it over and lift up your skirt.

Ashley took the chastity device and secured it onto Jake’s package. It was clear with a hole for him to pee. It came with plastic locks that had serial numbers on them. Once attached the plastic lock could not be removed without breaking it. Ashley slide the plastic lock though the hole and secured the device. Sarah took the camera a snapped a photo so they wouldn’t forget the serial number. Jake looked down and felt the device that was now basically a part of his body. It wasn’t the most comfortable and was going to take some getting use to. He really hopped it would not be a month before it was removed for the first time.

Maybe next change to a steel/titanium device and threaten JB weld?

H
 

Ready for the next part

Will have an update for everyone this weekend

Wasn’t able to get the update out yesterday. I will have something before Thanksgiving

Chapter 11

Ashley: What do you think ladies?

Sarah: I think it suits him pretty well. I love how it looks on him. I know we’ve had a lot of power over him but there is something about controlling is dick that is even more satisfying haha.

Amy: The look on his face says it all. I absolutely love it! It’s fun knowing he will remain a virgin until college at the earliest.

Sarah: Oh My God! I forgot you two never actually slept together.

Amy: Yeah I am so happy he never got the golden ticket. He did get a few blowjobs but that was it.

Ashley: Well I guess that is for the best since guys are usually more attracted to virgins haha.

Sarah: So what do we want to do the rest of the day with our bitch?

Amy: We have to prepare for tomorrow. Figure out his outfit and what we are going to make him do in front of the entire school. I know for sure I want him to learn a ridiculous dance to perform on command. Let’s find a routine online he can start practicing while we figure out everything else.

Sarah: I love that idea!

Ashley: Once we have the dance he will be doing it will be easier to figure out the outfit.

The girls started searching online for different dances he could do. They wanted something that was short enough they could have him do it quickly and also wanted it to be super girly. Jake stood there and continued to get use to the chastity device touching and pulling on it some. It was pretty uncomfortable and would take a lot of getting use to. Finally the girls had the video in mind. It was a TikTok dance to the song Do It To IT by ACRAZE. The dance included dropping it low with a hand up in the air and also some booty shaking.

Amy: Here is the dance you are going to learn for tomorrow. Right now that chastity device that you’ve been so interested in is in fact staying on for a month. Depending on how well you do with our orders the time will be increased and decreased. So get to it!

Jake: Yes Princess

Amy: Practice in the living room so we can watch while we plan out everything else.

It took Jake a while to learn the routine. Even though it wasn’t too complicated. He was pretty awkward when it came to dancing and didn’t really have that gene. The girls found this pretty entertaining. Half way through learning the dance they made him strip and continue while wearing nothing but the chastity device. As Jake moved around and shook his ass the device was definitely an annoyance and even hurt some. Slowly he was starting to get use to it. Once he finished learning the dance it was well after lunch time and the girls were pretty hungry.

Amy: I’m starving what do we want Jessica to make us for lunch ladies?

Sarah: If she is going to be a good house wife she will need to know how to make a good sandwich haha.

Ashley: Agreed! I will take a ham and cheese toasted with the crust cut off.

Sarah: That sounds pretty good. I’ll take the same!

Amy: I will take a turkey with swiss. Crust off as well but not toasted.

Jake: Coming right up! May I make myself a sandwich too princess?

Ashley: Haha you’re so funny Jessica. I really want to see you eat dog food in person. So once you serve us go ahead and make your lunch in a doggy bowl on the floor.

Jake sighed and went to go and make the ladies their sandwiches. Returning not much later with the exact sandwiches requested.

Jake: Here you are my beautiful princesses. Would you like anything to drink?

Amy: Water for all three of us will be fine.

Jake got the water and then proceeded to make his lunch. He could smell the dog food immediately upon opening the can. This was definitely something he was not looking forward to. He also made himself a bowl of water. Walking back out to where the girls were eating he set the bowls down and went to go dig in before being stopped by Sarah.

Sarah: Hold up! Bring the bowls over and place them by my feet.

Jake did as instructed and then Sarah proceeded to take her left foot and smash it in the bowl of dog food wiggling her toes and mixing it up.

Sarah: You can start your meal by cleaning off my foot with your mouth.

Jake looked down not wanting to make eye contact and started immediately without hesitation. Something that definitely would have caused him to pause just 2 days prior. He sucked and licked until the food on her foot was gone.

Jake: May I finish my meal now?

Sarah proceeded to lean over and spit a huge loogie into the bowl of dog food. Then again into the bowl with water.

Sarah: Yes you may and I want both bowls spotless before you stop.

Jake finished his meal and then took care of the dishes as the girls continued to talk and enjoy their Sunday. Amy’s parents would be back in a few hours so Jake would get to go home and rest before facing the pubic humiliation at school that awaited him on Monday.

Amy: So we have your outfits picked out but you wont get to see what we have chosen until Monday morning. With my parents coming home later we just have one more task for you today. You need to do you daily blowjob training haha. Go get the bigger one we used on your mouth before.

Jake retrieved the dildo as instructed. It had a suction cup on the back of it. Amy took it and stuck it on the door to the back yard that was glass. There was a fence that surrounded the yard so no one could see the door without being in the backyard themselves. The girls got the camera ready. They were able to freely move to both sides of the door while Jake did his task, but outside was the best view being able to look at his facial expressions.

Amy: You know the drill. Time starts when you are giving full effort!

She was already recording as Jake got down on his knees and started to suck the dildo. The girls took turns filming and pushing his head down further on the dildo. Surprisingly Jake’s gag reflex was already drastically improving. He was able to legitimately deepthroat if he relaxed and didn’t panic. Still when the girls were forcing him to go further he would choke and have to pull away. 8 mins into the blowjob training Jake’s mouth was getting sore. He was given the time remaining as he went on. Amy was being a little nicer not stopping the timer very often. While focused on the dildo Sarah slowly got closer to him from behind while Ashley and Amy were on the other side filming. Without warning she took her middle finger and proceeded to shove it up Jake’s bum.

Jake: Ummmm!!!! Ahhhhhh!!! What The Hell!!!

Sarah: Take it Bitch! No one said to stop sucking!

Uncomfortable Jake went back to finishing the blowjob while Sarah continued to finger his butthole and the other girls filmed the entire scene. Finally the task was over and Jake could relax knowing he was done with all of this until Monday.

i check everyday looking for more! I am hooked!!!

Excellent. Jake is so lucky!

Cant wait to see what happens Monday at school

A d h
 

Oh man is gonna suck

Chapter 12

Jake changed back into his normal clothes with the exception of his panties which he was required to wear at all times, and headed back home for some much needed alone time ever since the weekend started. His life was drastically different just two days earlier. He took some time to think about his options, but the more he thought about it the more he realized he was at their mercy and disobeying them would be social suicide for the rest of his life. At least if he made it through the rest of the year there was a chance they would leave him alone once the school year was over. Once home Jake didn’t speak with his parents much. They typically let him live his life. It wasn’t uncommon for him to be gone all weekend with little contact. Sometimes he would even be gone during the week staying with friends so it wasn’t unusual. He went to his room and rested. Even though tomorrow was going to be extremely humiliating he was already pretty use to the feeling. However having to face other people outside of a house would be a new experience. Exhausted from the weekend he set his alarm and fell right asleep even with the anxiety of what was in store for him the next day.

BRINGGG BRINGGG BRINGGG!!!! Jake’s alarm started going off waking him up in the middle of a dream where he was about to suck another man’s cock while the girls watched and filmed it. It took a little for him to realize it was a dream and time to get up for school. He had to meet the girls 30 mins before school started in the lobby and then change in the bathroom into whatever they had for him to wear. He still had time to spare and hopped in the shower. It felt weird still being hairless and wondered what the other students would think when they saw his legs. The water felt pretty good though running over his body. The soap slide with ease and felt really smooth to touch. Once he was done showering he got dressed and headed straight to school.

As he parked he noticed Amy’s, Ashley’s, and Sarah’s cars were already in the parking lot. He hadn’t been overly worried since he left Amy’s house on Sunday, but walking from his car to the lobby he started to sweat. It all really started to hit him knowing the girls could completely ruin his life, and he didn’t know how far they would push things in public. As he opened the door to the lobby he saw the 3 girls talking and giggling watching him come through the door. They were earlier than everyone else. It would still be a little bit of time until other students arrived which was somewhat of a relief to Jake, but also added some anxiety to what everyone’s reactions would be when they finally showed up.

Jake: Good morning princess.

Amy: Morning bitch. You ready for a fun day today?

Jake: Umm I guess.

Amy: Here is your outfit. Hurry up and change.

Amy handed Jake a bag with his outfit and he proceeded to the bathroom. Once inside he opened the bag to see what he had to wear for the day. His eyes widened as he realized what it was. The ballerina costume Amy had showed him shortly after arriving at her place. He didn’t have to wear it all weekend and wasn’t looking forward to seeing how it looked once it was on his body. Fortunately it at least had tights to cover up his newly shaved legs. It also came with ballet slippers instead of heels which was another huge bonus for the day. However on the downside it was definitely the most embarrassing of all the outfits and having to dance in it would be really awkward. He put the outfit on and took a look in the mirror. As he was staring almost in a trance he heard someone else open the door to the bathroom.

Random Student: Hahahahaha dude you have to be joking. You actually wearing that all day?

Jake: Uhhh yeah I guess.

Embarrassed and turning red he just tried to play it off. He could hear the girls outside laughing and started walking to the door. As he peaked out, the lobby had gotten much more crowded with people meeting up for the day. Awkwardly he realized he was first to get changed and was the only one dressed in a ridiculous fashion as he walked out of the bathroom. The girls continued laughing but even harder now. Jake noticed others starting to stare and giggle. They were also pulling out their phones and taking picture after picture. Guys were commenting things like “Man I am happy I am not him” and the girls who bought other players were saying things like “Aww I wish I thought of that”

Sarah: Looking good! Haha!

Ashley: I agree but he definitely needs his makeup done.

Amy: Haha obviously! I’ll do his face while one of you paints his nails.

Amy pulled out her makeup kit and got to work as Sarah started painting his nails a nice bright red to make them pop. By the time Amy was finished Jake looked like a trailer park whore with the exception of lipstick which Amy did not apply. He was definitely the center of attention in the lobby and was trying his best to keep his cool and not look anyone in the eye, but also didn’t want to appear as a total little bitch. He knew the more he showed his embarrassment the more the girls and other students would torment him.

Ashley: One last touch for the cherry on top!

Ashley pulled out a pink wig with pigtails that popped up and had bows with the hair ties. It was absolutely the cherry on top. It also didn’t really hide his face. Everyone could clearly tell who he was. Sarah then handed Jake some bright pink lipstick.

Sarah: See that group of freshmen girls over there staring at us? Go up to them, curtsy, and then ask if they could help you apply the lipstick haha. Also offer to pose for photos with them while your at it.

Sarah pushed Jake softly into the direction of the girls. He made his way up to them and did a curtsy as instructed. The giggles and stares turned into full blown laughter while they tried to contain themselves as Jake got out the words to see if they could help him with his lipstick.

Jake: Would any of you mind helping me put on this lipstick?

Jake held up the lipstick in his hand with his freshly painted nails. One of the girls approached and took the lipstick out of his hand with the biggest grin and started to extend the lipstick out of the tube.

Freshmen Girls: Sure thing haha. Pucker up for me.

The lipstick was applied slowly and meticulously as the rest of the group watched in utter astonishment. They definitely were not speechless though. Making plenty of comments about how good it looked on him and how it was definitely his color and suited him so well. Ashley, Amy, and Sarah got a pretty good kick out of the situation watching from maybe 20 feet away.

Freshmen Girls: You’re all set. Anything else we can help you with? Haha

Jake: No thank you. But would any of you like to take some photos with me?

All the girls took Jake up on this offer. One after the other posing with him and documenting the entire thing. As Jake was taking photos with the girls. Amy, Ashley, and Sarah made their way over.

Amy: What do you think of our friend Jessica?

Freshmen Girls: Oh he is gorgeous! We all love his outfit! Is that his new name?

Amy: Haha yeah we thought it fit him better! A lot of thought and effort went into this.

As all the girls were talking the bell rang indicating everyone had 15 mins until they were required to be in their first class.

Amy: Looks like we have to go, but first would you like to see Jessica do a little dance we made her learn?

Freshmen Girls: Oh absolutely!!!

Amy: You heard them! Show them what we taught you haha!

Amy pulled out a speaker and the song for the dance immediately started playing. Jake wasn’t immediately ready and fumbled a little to start dancing but quickly caught back up with the song and performed the dance for all of the girls intently watching. Still not out of laughter yet some of them were having trouble trying to catch their breath as the dance ended.

Sarah: Not good enough. Again from the top.

Sarah started playing the song again. This time Jake was on point and put in a ton of effort to hit every move to the best of his abilities. The bell rang again as Jake finished the dance signaling they had 10 mins until they had to be in their first class. Satisfied with the second performance everyone said goodbye and started making their way to first period.

At
 

What did the ballerina costume look like

Chapter 2 gives more details...

"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."

But this is what I had in mindAttachment 10412

Asf
 

Oops sorry my bad

If hes still wearing a pink thong wouldnt that show through the white costume?