Jack and Phoebe Ch. 06

Stephanie brought her hand down smartly on Phoebe's right buttock, instantly leaving a red handprint and causing Phoebe to jerk in her restraints and yelp.

"Stef is a bitch!" shouted Phoebe, defiantly.

Another slap to her left buttock caused a matching red handprint to form, and again Phoebe jerked and yelped.

"I think you've angered Steph," said Jack, "maybe you should apologise."

"I'll never apologise to that bitch," spat Phoebe, "she can eat my ass!"

Slap, slap! Two more slaps rained down on Phoebe's butt, one on each buttock.

"I don't think she is going to respond to spanking," said Jack, "maybe I should try something."

Jack ran his hand down Phoebe's back with the barest of pressure, barely touching her skin with his fingertips. When he reached her bum he spread his fingers and continued over her buttock and then down her left leg. He walked to the other side of the bed and started at the ankle of her right leg and repeated his stroking in the opposite direction. He did this a few times, and eventually he noticed Phoebe pushing her hips into the pillows, and he heard her emit some soft sighs.

SMACK!

Jack brought his hand down in the middle of her butt, leaving his massive handprint alongside Stephanie's smaller ones.

"Oww! You fucking bastard!" screamed Phoebe, "I'll get you too, I won't forget this!"

"And his little dog too?" added Stephanie, with howls of laughter.

Jack cracked up and even Phoebe snorted trying not to laugh.

"Okay, fun's over let me up now!" said Phoebe calmly.

"Fine, Phoebitch, say 'red' and we'll untie you and we'll both go home," replied Stephanie.

"I am not Phoebitch!" shouted Phoebe.

"You are now, maybe we should take some photos and send them to Aria!" suggested Jack, "or even better invite her to join in!"

"No! NO! I'll do anything!" begged Phoebe, desperately trying to turn her head to check that neither of them had their phones out.

Click! Flash!

"No!" shouted Phoebe.

"Oh, that's a good one, look you can even see her butthole!" said Stephanie, holding Jack's phone for him to look at.

"Please!" whimpered Phoebe, "I'll do anything!"

"Interesting offer, I think we should explore that," said Jack.

Click! Flash!

"Anything, just no Aria!" whined Phoebe.

"I think she's ready," said Stephanie.

"Yes," agreed Jack, "she seems to be."

Maggie was bored, she had been sitting in her room trying to find something to do, having searched through her shelves for an interesting book, she popped next door to Jack's room to see if he had a book she could borrow. After noticing that he definitely had a penchant for Sci-Fi, she started to select books and take them down, read the blurb and then put them back when she found that they did not interest her. She did this all the way through one shelf, and moved onto the shelf above his desk.

Ding!

Jack's laptop screen came to life with a notification. Maggie looked at the screen, and, out of curiosity, clicked on the notification. The computer opened on Jack's photostream, with a notification that said that photos had been added. Maggie, without thinking, clicked on the photostream and was confronted with the rear-end of a girl with her legs spread showing a very messy pussy and a series of red handprints on her butt.

"Holy shit!" whispered Maggie to herself.

She ran to the door and stuck her head out into the landing, listening to see if she could tell where her parents were. She heard her Mum and Dad talking in the living room, so she ducked back into Jack's room, shutting the door. She sat down at the desk and returned her attention to the laptop. She looked closer at the photo, noticing that the girl was completely shaved, and she had something oozing out of her, which, after a moment's thought, she realised was cum. She clicked the next photo, and found another photo of the same girl, this one had a part of the face visible over the girl's shoulder.

"Ah fuck! Phoebe!" she said, "oh shit, that means that that's Jack's cum!"

Maggie found herself getting aroused as she clicked to the next photo, this time it was clearly a photo of Phoebe, but she had a hard cock in her mouth, the owner of the cock was not revealed but it was a fairly good bet it was Jack's, in Maggie's opinion at least. The next photo was another one of Phoebe sucking a cock, deeper in her mouth this time, but with more of Jack on show. Something about this photo bugged her, she looked at how Jack was sitting in front of Phoebe, how he had his hands on her head, and something looked wrong. If Jack was holding Phoebe's head, and Phoebe was tied up, who was taking the photos? Maggie jumped out of her seat when she saw the next photo, Jack had been replaced by another girl! The unknown girl was forcing Phoebe to lick her pussy! Maggie slipped her hand into her knickers, finding them damp and her clitoris poking up, hot and hard. The next photo had the mystery girl on all fours in front of Phoebe, and it looked like Phoebe's tongue was on the girl's anus!

"Holy shit! Holy shit!" Maggie whispered, flicking her clit hard and fast now.

Creak!

Maggie almost wet herself as she heard someone coming up the stairs. She panicked for a second and then selected all the new photos and emailed them to herself and pushed the power button on Jack's laptop putting it back to sleep. She grabbed a random book off Jack's shelf and headed back to her room.

"What were you doing in Jack's room, Maggie?" asked her mother half-way up the stairs.

"Oh, I went looking for a book," replied Maggie, trying to look calm, "I found this one."

She waved the book she had grabbed without looking.

"Oh okay, Dear, make sure you tell Jack when he gets back, you know how he is about his stuff!"

"Yes, Mum!" said Maggie, closing the door to her bedroom behind her.

Maggie practically dove onto her desk chair and opened the email client on her laptop. She saw the email from Jack's address, with its attachments.

Click! Flash!

Stephanie was on all fours in front of Phoebe, and Phoebe was rimming her like there was no tomorrow. Jack walked round to the other side of the bed and took another photo, this one showing both girls' faces.

Click! Flash!

He pushed the phone right up to Phoebe's face, so it was just her face with her tongue pushed out licking a butthole, the tip pushing into the hole slightly.

Click! Flash!

"Oh, Phoebe!" Jack whispered in her ear, "I'm going to enjoy wanking to that one when I get home, I might even make it my laptop's wallpaper!"

Phoebe gave him a filthy look, but did not stop what she was doing.

"Jack," said Stephanie, "has Phoebe ever licked your arse?"

"No, you know what," replied Jack, "she never has."

"Oh you don't know what you're missing, she has the best tongue!" said Stephanie with a huge grin, "maybe you should try it for a while!"

Stephanie jumped off the bed and Jack took her place on all fours in front of Phoebe. Immediately, Jack felt Phoebe take one of his balls into her mouth, she licked it and sucked it and it felt amazing, she'd never done that before.

Click! Flash!

After a few minutes of licking and sucking his balls, she moved on to his perineum, licking and kissing the strip of skin between his balls and his anus. Phoebe pressed her tongue hard into his skin and licked for all she was worth, Jack could feel his cock hardening even further from the brand new sensation.

Click! Flash!

Finally, Phoebe moved to his butthole, she began with some circular licks that barely registered but soon she was working up and down with hard licks. Jack was in heaven, he had never experienced a feeling like this and he had to grab onto the headboard hard to prevent himself from stroking his cock.

Click! Flash!

Phoebe did not understand what was happening to her, she was degrading herself like she had never imagined, her boyfriend and best friend were humiliating her and forcing her to perform acts that she had never even considered before and she felt she was on the edge of the biggest orgasm of her life. The frustrating part was she was stuck on that edge and it was driving her crazy, if she could have just reached between her legs she knew she would be able to crest that hill, but her arms were tied tight, and no amount of wriggling had brought the pillows into contact with her sopping pussy. Phoebe made her tongue a point, she intended just adding a little more pressure onto her licking, but Jack had relaxed so much that, when she pushed just a little bit, her tongue sank almost all the way into his rectum.

"Oh fuck!" shouted Jack as he came hard, coating the sheets in his cum.

Click! Flash!

When he recovered Jack got off the bed and let Stephanie take his place, Phoebe went straight to work licking Stephanie's pussy. Jack wondered if the pair of them had broken his girlfriend. He had never imagined that Phoebe, straight-A's, straitlaced Phoebe, could act in such a depraved and perverted fashion. He still had one thing he wanted to try, but he knew it had to be done carefully, so he got to work. He knelt behind Phoebe, and remembering how she had licked him, he went to work gently rimming her, being careful not to let her come. Very soon, he could tell that she was into it and wanting more as she was pushing her arse back into his face. He increased the pressure and speed of his tongue on her anus and made sure that he licked every part of the sphincter. At some point, Stephanie came again, and after lounging for a while she left the room. Jack kept up his licking, and Phoebe was now babbling, begging him to let her come.

Stephanie reappeared with a jar of coconut oil in her hand, she handed it to Jack. Jack swiped his middle finger through the contents of the jar and placed the digit against Phoebe's backdoor. Slowly, he sank the finger into Phoebe, pushing in slightly and then pulling out again before pushing in slightly further. He'd put fingers in her before, but he wanted to be absolutely sure to do it carefully this time. Eventually, Jack had sunk his middle finger all the way to the third knuckle, Phoebe was groaning and she was pushing back to meet his thrusts. He increased the speed slightly and added some rotational motions to his backward and forward. Once he was sliding in without resistance, he pulled his finger out and using his clean hand scooped some more oil out of the jar and fed it into Phoebe's slightly gaping anus, and then recoated his middle finger and added his index finger to the mix. Gently, he pushed his two fingers into Phoebe, they slipped in surprisingly easily, and he was soon sliding them in and out without resistance. He completely withdrew them for a moment and saw that her anus stayed dilated before slowly starting to close up.

"When Jack's done with you," Stephanie told Phoebe to her face, "I'm going to push my fist into you, if you're a good girl it'll be into your pussy but if you're bad, you know where this is going!"

Stephanie made a fist in front of Phoebe's face, Phoebe's eyes opened wide.

"I'll be a good girl! I promise!" she whimpered.

"Hmm.. we'll see Phoebitch!" replied Stephanie.

Jack had three fingers working into Phoebe's rectum without resistance now, he was pushing and pulling them quickly and he noticed that as he pulled out her sphincters would try and hold onto them but when he pushed in they opened up for him. It was time.

Phoebe was almost out of her mind, she had been on the edge for so long that she was going mad. Jack was stroking her in a way that she had never experienced before, it was amazing but it was not going to make her come and she was not sure how much longer she could take it. She was just considering calling out her safeword, so at least she could finish herself off, when Jack's fingers disappeared from her arse. She felt his weight shift on the bed, so she tried to turn around and see what was happening behind her. She turned her head just enough to see Jack up on his knees with his rock-hard cock in his hand moving forwards. He was going to fuck her pussy and make her come! She was relieved. She felt so happy, until she felt something hot and hard pressed against her butthole. It was much larger than Jack's fingers and it wasn't slipping in easily like his fingers had. She felt the pressure on her anus increase, until finally, it popped through both her sphincters and sank into her rectum.

"Oh fuck!" she shouted, "oh fuck!"

Jack kept pushing forward until he was completely embedded in Phoebe's behind.

Click! Flash!

"Got to have a souvenir!" laughed Stephanie, "how many girls have a photo of their anal virginity being taken?"

Jack started to pull out slowly.

"Oh, oh!" cried Phoebe, "oh god!"

Jack pushed in again, despite coming several times already he realised he was not going to last long. Phoebe started to push back against Jack's thrusts, and he picked up speed. Jack picked up the rhythm and started hammering into Phoebe; he managed about six thrusts before blowing his load deep inside her. Phoebe's eyes rolled back in her head and she came harder than she had ever come before, the hours of teasing and stimulation, the depraved acts of debauchery that she had done or had done to her, had built her up higher than she ever thought possible. She saw stars, the veins and sinews in her neck stuck out as she threw her head back and arched her spine, a river of juices gushed out of her, coating Jack's balls and the sheets in her cream, and her anus twitched open and closed around Jack's cock.

Click! Flash!

Stephanie untied Phoebe and helped Jack get off her. The pair of them marvelled at Phoebe's gaping anus; it remained open despite being empty for a while and then gradually closed up, all the while Jack's spunk slowly leaking out and mixing with Phoebe's mess on the sheets.

Phoebe lay still, little ripples and aftershocks occasionally causing a leg, arm or her head to twitch.

"I think you fucked her to death!" Stephanie said to Jack as they stood there watching Phoebe recover, "Death by fucking, DBF! Told you I'd get my revenge, Phoebitch!"

Maggie was laying in her bed, her belly full of Chinese food and her knickers round her ankles. Her right played with her sopping wet pussy, her left held her phone with Jack's photos displayed in a looping slideshow. She could not believe what the photos showed, she had never dreamt that Phoebe would lick someone's arsehole, let alone two people's. The photo of her as Jack forced his cock into her butt was one of Maggie's favourites. The look on Phoebe's face as Jack slid into her made Maggie more aroused than she could ever remember and intensely jealous too. She was glad that se had snuck back into Jack's room after dinner and grabbed the rest of the photos.

Maggie clicked the button on her bullet vibrator and ran it over her clit, her back arched and she gasped. The slideshow moved on to a picture of Phoebe with her tongue on Jack's arsehole, Maggie could see how Phoebe's tongue was partway inside Jack, and she could see strings of cum dangling from Jack's hard cock, his balls pulled up tight against his body. Maggie rolled onto her front, using her knees to push her butt into the air. She moved the vibrator from her clit down through her labia, coating it in a plentiful juices as it passed; it moved across her perineum, causing her to moan out loud. Finally, it came to her anus, and as it touched her there it triggered her orgasm. She fell flat on her front, dropping the phone and vibrator as she grasped the sheets and rolled to her side. She struggled to catch her breath and found herself panting as wave after wave of her climax spread out from her clitoris and anus and swept through the rest of her body.

Jack, Phoebe and Stephanie lay together in a freshly made bed and apparently Stephanie snored.

"Tonight was amazing," whispered Phoebe, "I've never felt like that before."

"I know," replied Jack in a hushed tone, "and I've never seen you like that before. First you were all in charge and evil, and then you were begging. I loved both Phoebes; Phebes and Phoebitch!"

Phoebe giggled softly, and pulled on Jack's arm.

"It's your turn next time," she said as she ran her hand down his to his groin and grasped his soft cock, "I want you tied up again, begging for mercy!"

Jack groaned as her strokes woke his cock up, he pulled her in for a kiss and soon he was fully erect.

Phoebe slipped her leg over Jack and lifted herself up until she was straddling him. She reached in between them and angled Jack's cock and pushed backwards, he slid into her easily.

"It doesn't always have to be crazy," said Phoebe as she gently rose and fell, "I like this, just as much as the other."

Jack reached up and pulled Phoebe down onto him, pressing his lips to hers and lifting his hips in time with hers.

"This is my favourite Phebes," Jack whispered into Phoebe's ear, "just you and me, like this."

When Jack finally got back into his bedroom it was almost four in the morning, he quickly stripped and crashed on his bed.