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.
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