Jack and Phoebe Ch. 14

Story Info
Phoebe goes on an adventure and Aria slams the trap closed.
25.2k words
4.58
3.7k
3

Part 14 of the 14 part series

Updated 06/11/2023
Created 06/25/2022
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There are absolutely no characters under the age of 18. All sexual acts take place between adults over the age of 18 years.

Jack and Phoebe 14

Click!

"Broke all the rules, Played all the fools. Yeah, yeah, they, they, they blew our minds. And I was shaking at the knees, Could I come again, please? Yeah, them ladies were too kind. You've been

Thunderstruck, thunderstruck"

Aria turned off her clock radio and rolled out of bed with a song in her heart. Today was the day when everything paid off, all the scheming and plotting, all the hard work - today was the day Phoebe Harrington kissed her feet.

**

Phoebe had been awake for a while, listening to her two best friends sleeping beside her. Stephanie snoring and Sally making cute little sighs and murmurs. She had also been thinking of all the interesting things to do to her two friends when they woke up, her fingers finding their way between her legs, just teasing herself.

Ding!

Phoebe reached over the snoring Stephanie and picked up her phone from the bedside table. She looked at the email notification on the phone's lockscreen and saw an email from an address she did not recognise with the subject line that read "Read this now!". She opened the email and immediately felt like someone had ripped the breath from her lungs as she was confronted with a picture of her sucking an anonymous cock. She recognised the photo immediately as one of the photos that Jack and Stephanie had taken during their second three-way session. She scrolled down, the next photo was her with her mouth on Stephanie's pussy. The final photo was her with the tongue buried in Jack's butt. In all three photos she was the only identifiable person, and it was clear, from the expression on her face, that she was enjoying herself. After the final photo there was just a single sentence.

BE A SHAME IF THESE GOT SENT TO EVERYONE YOU KNOW, WOULDN'T IT?

Phoebe looked at the email address again, trying to see if she recognised it or if there was a clue to the identity of the sender.

Her hand covered her mouth, tears filled her eyes and she could feel her pulse racing. She thought that she was going to be sick and she clambered out of the bed and pushed her head into her wastepaper basket beside her desk and retched.

Ding!

She turned her head and saw the screen on her phone, still so tightly clasped in her hand that her fingers were white, light up and another email notification. She opened the phone and then read the email.

Hello Phoebe,

I understand that you may be feeling a little distressed right now, so I will give you a little while to calm down and get yourself together.

You will receive instructions in the next email.

If you follow those instructions exactly then nothing will happen.

If you fail to follow those instructions to the letter, if you tell anyone else about these emails or if you make any attempt to identify the sender you will find that everyone you know gets to see just what you get up to in bed and with whom you do it.

If you accept these terms, then all I want to see is a reply with the words, "Yes, Master". If you don't, well, I suppose you should get used to the idea of everyone knowing how you look with a big cock in your arse and how much you really enjoyed it.

Phoebe read through the email a second time, and then, whilst reading it a third time, noticed something in the second paragraph that caused her to pause.

"It's fucking Jack! Calling himself 'Master' and calling his cock 'big' it has to be him!" whispered Phoebe to herself, a wave of relief descending on her and washing away her nausea and anxiety, "oh, he is going to pay for this later."

Smiling, she hit reply and began to type an email in response.

**

Aria was sitting in her chair, she was dressed in just her underwear, her hand was working hard inside her knickers. She had been taken entirely by surprise at just how turned on composing and sending the second email had made her, and the anticipation of receiving a reply was causing her to build to a monumental orgasm. She looked towards her wardrobe and contemplated getting some toys out to play, but she was interrupted by a new email notification.

Ding!

Without hesitating, she clicked to open the email.

Yes, Master 😉

"Fuck yes!" Aria said to herself.

She was just about to close the email when she looked at it again and noticed the winky emoji after "Yes, Master". She stared at the little winking face for a while, her head tilted to the side.

"That's a very strange way to reply to a blackmailer with pictures of you taking a cock in your arse."

Aria was thrown, she pulled her hand out of her knickers and sat up in her chair. Why would anyone end such an email the way that Phoebe had done? She sat there for a while staring at the email on her laptop screen, trying to put herself in Phoebe's position and trying to think of all the reasons for that winking emoji. Maybe Phoebe always ended emails with that, and so it was just a force of habit? Maybe she had done it because she thought that the whole thing was a joke? Maybe she thinks she knows who's doing it? Maybe she's into it?

"That's it," Aria whispered, flicking back to the photos she had taken from Maggie's phone, "there are at least three people in the photos, and in all the photos Phoebe is restrained. Maybe the freaky little Phoebitch gets off being ordered around, and she thinks that whoever took the photos is the one who sent her the email."

Aria could not believe her luck as she got to work on her next email.

**

Ding!

Hello Phoebe,

Just to remind you, if you mention these emails to anyone, even if you think you know my identity, then you will have broken the rules and will suffer punishment. Even if you actually know who I am and you text or call me to discuss it, I will punish you. The only way you are to discuss anything to do with this situation is via this email address. There will be no further warnings or chances.

Your first task today is a nice simple one. Put on a nice short skirt, a T-shirt, kneesocks and some plimsolls. When you're done, take a photo and send it to me.

Phoebe read through the email several times to make sure she fully understood what Jack wanted her to do. If they were going to play a game, she was going to play it correctly. She went to her wardrobe and found her white tennis skirt and t-shirt, and then pulled out a pair of white, cotton knickers and a plain white bra from her underwear drawer and put them on, all the while listening to Stephanie's snores and Sally's cute murmurings.

She stood in front of her full length mirror to take the photo and then had an idea. She repositioned the mirror so that the bed could be seen and then returned to her position in front of it. She took the photo and examined it closely. She looked good, decked out in the whites and plimsolls, and in the background were the two naked bottoms of the sleeping girls.

"That should get Jack's motor running!" she whispered to herself as she composed and sent the email with the photo attached.

**

Ding!

Master,

I've dressed as instructed. I hope you like the photo! 😉

Phoebe

"Ahh, that fucking winky face again!" laughed Aria, as she studied the photo to check Phoebe's compliance, "oh, you naughty, little girl and you didn't follow the instructions, we will have to think of a punishment for that!"

**

Ding!

I'm very disappointed with you. You have unfortunately failed to follow my instructions and will need to be punished. If you manage to correct your failure in the next 15 minutes, with photographic proof, I shall be lenient.

Phoebe read through the email and was confused. She had followed the instructions, she had picked a short skirt, T-shirt, kneesocks and plimsolls. She stood in front of the mirror again and examined her outfit. Was the skirt not short enough? She turned and looked over her shoulder and saw that the skirt barely came down below her butt, her white knickers were clearly visible unless she stood very carefully, any shorter and it would more properly be considered a belt. She looked at the original instructions again, counting off the items of clothing she was wearing against the list.

"What the fuck am I doing wrong?" she asked herself, a little too loudly as the question caused Stephanie's head to pop up and look around the room.

Stephanie was enjoying a dream about dominating Sally and Phoebe when she was woken by the sound of Phoebe's voice. She lifted her head and was confronted first by Sally's nude form sprawled out next to her and then by the back of a very dressed Phoebe. She watched Phoebe looking at herself in the mirror and then checking her phone.

"You sending Jack some sexy snaps or something?"

Phoebe jumped, turning to face Stephanie, her face flushed.

"What's the problem Phebes?" asked Stephanie, propping herself up on an elbow beside the still sleeping Sally.

"Jack has, for some reason, decided that he wants to play a little game today, and well, look at this," said Phoebe, showing Stephanie the first email with the photo and then the others, "so I followed his instructions and sent him a photo, but he told me I had it wrong."

"He certainly has an interesting imagination, doesn't he!" said Stephanie, eyebrow raised.

Phoebe sat on the bed and checked her watch.

"I don't have much more time to sort this out, I'd like to make a little bit of an effort to avoid his punishments, at least make him wait before he gets to have his way with me!" replied Phoebe, a cheeky, little grin on her face, "he scared the shit out of me earlier though, I honestly thought someone else had got hold of the photos you and he took last week."

Stephanie re-read the email with the dressing instructions.

"Let me see you," she said, indicating for Phoebe to stand beside the bed and kneeling up on the mattress herself, "you have a short skirt, socks, T-shirt, right, you wearing anything not on that list?"

"Duh!" exclaimed Phoebe, pulling the hem of her skirt up to reveal her underwear, "I bet he means these!"

"That'll be it," replied Stephanie, "but if you're going to take 'em off, you'll have to change your skirt, that one is too short, you'll get arrested if you go outside."

"You might have a point," replied Phoebe, pulling the underwear off and turning towards the mirror to see how much was on view.

"Yeah, I can practically see your butthole!" laughed Stephanie, receiving a pillow to the face from a laughing Phoebe.

"I think I have something else," said Phoebe, rummaging through her wardrobe.

Phoebe pulled off the tennis skirt and pulled on a slightly longer, looser-fit skirt with a floral print.

"Ahh, that's the one," commented Stephanie, clapping quietly, "short enough to show off your awesome legs and long enough that you aren't giving the person sitting opposite you on the bus a gynaecological view."

Phoebe giggled whilst pulling off her bra and pulling the T-shirt back on. She went back to the mirror and took the photo, making sure that a naked and oblivious Stephanie could be seen kneeling on the bed behind her.

"Perfect!" she said as she emailed it to her blackmailer.

**

Ding!

This any better? 😉

Aria went to check the photo, to make sure that Phoebe had removed the offending underwear but was distracted by the full frontal nudity of Stephanie Miller in the background.

"Oh, I think we have found your second Task Phoebitch," whispered Aria, as she set about typing up an email.

**

Ding!

Very good. Seeing as you rectified the issue so quickly, I have decided that you shall be spared a punishment. I will not be so merciful in future. Now on to your next task. I think you will enjoy this one. Seeing as you seem to have some interesting companions, I think it is only fair that you enjoy each other for a while, they are bound by the same rules as you. You have 30 minutes to take some interesting photos of yourselves together, what you get up to and how you photograph yourselves is entirely your decision, but bear in mind that I want to be entertained, so put some effort into the photos.

Phoebe read the email with a smile on her face, she knew exactly what Jack wanted and he did not mind doing that for him. She looked over at the sleeping Sally, and smiled.

"Shall we wake Sally up with a kiss?" she asked Stephanie.

Stephanie rolled over so that she was level with Sally's head and kissed the sleeping girl gently on the cheek, which did absolutely nothing to rouse her.

"I was thinking you should kiss her somewhere else," suggested Phoebe, snapping some photos with her phone, "might have more luck waking Sleeping Beauty here."

Stephanie crawled down the bed so that she was level with Sally's backside, and laid a couple of kisses on her butt cheeks.

"Is this what you were thinking?" she asked Phoebe, who was still busy taking photos.

"I was thinking something along the lines of this," replied Phoebe handing the phone to Stephanie and climbing onto the bed.

Phoebe put the tip of her tongue on the small of Sally's back and traced a line straight down into the valley made by her two cheeks. This drew a quiet groan from the sleeping girl, but failed to wake her up. Phoebe, knowing that time was a factor, decided to go for broke and pushed her tongue hard against Sally's little pink butthole. This action caused Sally to buck, her head popped up with a squeal and she rolled onto her front to find out what was going on.

Phoebe and Stephanie fell about laughing at Sally's reaction. Once Sally had woken up fully, Phoebe quickly explained the game she was playing with Jack.

"We were hoping you'd join in with it, Sally," said Phoebe, "I know that Jack would love it, and I bet you'd enjoy yourself too."

"I don't know, Phoebe," replied Sally, pulling her knees up to her chest and wrapping her arms around them, "I don't really think of Jack that way, and although I'm not ruling out anything in the future, I don't want to give him those kinds of photos of me. Not yet at least."

"She can just take the photos then," suggested Stephanie, handing the phone to Sally, "that way she won't be in any of the photos, and we won't have to worry about holding the phone or balancing it on something."

"Ooh, that's actually a great idea," said Phoebe, pulling Stephanie onto the bed, "come here and get your reward!"

Phoebe rolled Stephanie onto her back and kissed the naked girl hard on the mouth, their tongues duelling, her hands taking hold of Stephanie's breasts. Sally jumped out of bed and began to take photos of her two best friends making out.

**

Ding!

Aria opened the email, not sure what to expect.

Hope you "enjoy" these as much as I enjoyed taking them. 😉

Aria clicked through to the images and was immediately impressed with Phoebe's enthusiasm. The first picture showed Phoebe making out pretty heavily with a naked Stephanie on, presumably, Phoebe's bed. Aria was already very familiar with naked Stephanie, having spent several lunch breaks tormenting her and Sally Joseph, but this was on another level.

The second picture featured Stephanie lying on her back with Phoebe kissing her nipple, a hand wedged between Stephanie's legs. Aria liked where this was heading, Phoebe was providing her with even more compromising material, all of which would be useful later on.

In the third image Phoebe had travelled further down Stephanie and was busy kissing her bellybutton. Aria's hand slipped back between her legs as she flicked to the next photo.

The final photo featured Phoebe between Stephanie's legs, tongue working on the naked girl's pussy. Aria's fingers were gently stroking herself, but she found herself bitterly disappointed that this was the last one and this killed her mood. She needed to get things moving a little more quickly, push Phoebe a little further and get her doing some more interesting things.

**

Ding!

You were right, I did enjoy those photos but I was disappointed that there were so few of them. It's time for you to go out for a little walk in the park. Take Stephanie and Sally, dressed in the same manner as you, with you to take the photographs. Email me when you get there.

Phoebe read through the email, and smiled. Jack had obviously decided that he wanted her to be a little less comfortable, well, she could play along with that, she was more resilient than people gave her credit for, although the thought of going out dressed as she was did raise her anxiety level slightly, not to mention her level of arousal.

"He wants us to head out to the park, and you two are supposed to be dressed like me," Phoebe announced to the other two girls.

"I don't think I can, I have to go home anyway," replied Sally, "Jack'll have to make do with just two girls doing his bidding."

"Yeah, Phebes, I don't think I can either," added Stephanie, "my mum wasn't particularly happy with me for staying here last night, so if I don't at least make an appearance at home this morning she's going to be a nightmare when I do eventually go home."

Phoebe found her level of bravery drop slightly as she realised that she would have to complete Jack's challenges alone, but she was determined to show Jack that she was up to doing anything he could dream of, and knowing that her revenge, when she finally exacted it upon him, would be all the more sweet because of it.

Stephanie and Sally dressed and left, and Phoebe locked the door and walked to the bus stop. She caught the bus, thankfully as it was a Sunday morning the bus was relatively empty and she was able to sit downstairs close to the rear doors, doing so extremely carefully so as to not flash anyone on the bus.

When she arrived at the park she walked through the gates and down the path between the trees. The park consisted of two large open fields, one with a cricket and football pitch with pavilion and changing rooms and then the other a very large meadow with mown grass, a children's playground at one end and a bowling green and clubhouse at the other. Both sides were separated and ringed by a tree lined path with broad, tall horse chestnut, sycamore and oak trees.

The park was not crowded but there were a fair number of children riding bikes, playing on the swings, roundabout and slides and flying kites. A family was laying out a blanket, no doubt planning to have a picnic at lunchtime. The occasional shout could be heard from the football pitch as a Sunday league game took place, two teams of amateurs and three officials watched by a handful of their friends and family and the occasional dog walker.

It was a pleasant autumn day and no one was paying any attention to Phoebe, but thanks to the lack of underwear, tight T-shirt and short skirt she felt like all eyes were on her. Phoebe pulled out her phone and composed her arrival email to Jack.

**

Ding!

Have arrived at the park and am on tenterhooks awaiting your next instruction Master! Hope it's nice and naughty! 😉

Aria read the email and laughed. Phoebe really did think she was corresponding with her boyfriend. Aria typed her next set of instructions and sent them off and then picked up her phone and sent a couple of text messages.

**

Ding!

Well done. Walk around the park, let me know if you see any friends.

After reading the email Phoebe felt a little worried, although she knew Jack would not ask her to do anything she would not enjoy, she also knew that the range of things she enjoyed had expanded quite a lot over the past fortnight, and the kicker was that she knew that Jack knew that. The way he had treated her the other night, how much she had enjoyed it, not to mention how turned on just thinking about it made her, scared her, because she knew that today Jack would actually have to ask her to do something extreme for her to refuse and even then she was not sure she would actually say no to him.