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.
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