Yes

Zoey really didn’t want to anger her blackmailer. What choice did she have? She bolted downstairs, straight to the fridge and dug around. Luckily, she managed to find one.

She heard a thud upstairs. Checking the clock on the oven, she could see she had 2 minutes to get back to her desk. And someone else was awake upstairs. She quickly hid the cucumber under her robe and snuck up the stairs. Her brother’s door was open. He was probably in the toilet.

Zoey briskly walked into her room and shut the door behind her. She placed the cucumber on her desk and took off her robe, sitting naked back on her chair. She heard a laugh echo through the speakers.

“Hahaha, with 30 seconds to spare. And you even found a cucumber, I’m impressed.”

Zoey reached forward and tried to turn her speakers down, but it seemed to have no effect.

“Please, please be quiet. My family can’t find out about this.” Zoey begged.

“That’s not really my problem, is it?” the mystery man responded.

Zoey heard her brother’s door close down the hallway.

“What do you want from me today?” she asked, scared of the answer.

“Oh, I’m sure you can guess what the finale will be, but let’s get you warmed up first. Let’s start with you playing with your tits first.”

‘That’s kinda tame. I guess I can do that’

Zoey quickly grabbed a breast in each hand and started squeezing. They easily fit inside her hands, but there was enough to grab hold of. She couldn’t help but wonder what larger tits would feel like in her hands.

“Pinch your nipples, I want to see them get hard!” demanded the man. Zoey complied, placing a thumb and forefinger over each nipple and started to squeeze. She closed her eyes, and almost enjoyed it, if only she could forget why she was doing this.

“That’s it. You work those nipples. You’ve got a nice rack there Zoey. Not very big but they’re perky.”

She snapped out of her daze and scowled at the camera.

“There’s no need for that face, I was just giving you a complement.”

Zoey looked down at her tits again, almost in shame. Part of her wanted to impress this man, even if he was black mailing her. Was it a desire to be free of his threats, or maybe a bit more? No-one had complemented her breasts before. It felt nice to almost feel wanted.

“That’s enough now dear. I hope your feeling horny. Now take me over to your bed, spread your legs and put the laptop down between them so I can get a good look at that pussy of yours.

Zoey reluctantly picked up her laptop and pulled out the charger.

“Don’t forget your cucumber! You’ll be needing that soon.”

She had hoped he had forgotten about that. She grabbed it before heading over to her bed. Zoey placed the laptop at the end of her bed and spread her legs so her feet were either side of it.

“Place a pillow under your ass, I can’t get a good angle.”

Zoey sighed as she grabbed the pillow from beneath her head and placed it under her butt.

“That’s better. Spread your lips again, I need to have a good look.”

She placed a hand either side of her vagina and pulled the lips apart, revealing her pink inner.

“Oh yeah, there’s nothing better than young fresh pussy. Tell me Zoey, have you ever had a dick in there before?”

“Yeah, once.”

“And did you enjoy it?”

Zoey thought back to the only time she had ever had sex. It was a couple of years ago, behind a bike shed at high school. The guy was some dumb idiot with no other friends. At the time, she thought they were in love but she realised just how **** she had been after the three minutes he lasted. His tiny cock had barely broken her hymen and he failed to make her cum. He couldn’t look her in the eyes after that, and they never spoke again.

“Not really” she replied, not wanting to tell the whole story to this stranger. Her parents didn’t even know it had happened.

“That’s a shame. If I was with you, I would let you know how real men fuck women. You would be screaming all day and night.”

“I don’t doubt you.”

“And you shouldn’t. Anyway, enough chat. Show me how you play with yourself.”

Zoey released her pussy lips and started flicking her cliterous with her right hand, while her left moved up to her tits. All this thinking about sex had gotten her quite worked up again and she slowly moved her right hand deeper into her folds, finding her entrance. She slowly started to push her index finger into her cunt, right up to her first knuckle, and then pulled it out.

“Show me that finger. I want to see your juices dripping off of it.”

Zoe held her hand close to the web cam. She hadn’t realised how turned on she was, and her finger was dripping with her lubricant.

“Now put it in your mouth and tell me what it tastes of.”

“What? You want me to taste my own pussy?”

“Yeah, and be quick about it”

Zoey thought about it for a second before moving her finger towards her mouth. She’d be lying if she said she wasn’t curious to find out what a pussy tasted like, but she’d never thought of tasting herself.

She put the finger in her mouth and licked it clean. It didn’t taste of much, a bit salty if anything. She pulled her finger out of her mouth and relayed this to the hacker.

“Mmm, bet you liked that you little slut. Now, try and fit as many fingers as you can in your fanny. The more you get in, the easier the next step will be.”

Zoey got worried here. What could possibly be next? The cucumber? She was normally so tight. When she was really turned on she could fit three fingers in. There was no way she could fit that whole thing up there!

But she had to try. She slowly slipped in one finger, and then another. After fingering herself for a bit with those two, she started to squeeze in a third. She could feel the skin stretching as she pushed it all the way in. Then she tried to fit her pinky in. It hurt a lot to just have her nails in, but she tried to push in further anyway.

“Ahhh, no. I can’t do it. I’m too tight.”

“Well, that’s too bad. Because you’re going to need to fit that cucumber up there.”

“It won’t fit. I’ll rip my vagina in two!”

“Again, not really my problem. You’ll have that in in 1 minute or I’ll send a picture of you to your parents.”

Zoey’s face went white. How was she going to do this?

“Time’s ticking by the way. I would start soon.”

‘This guy is fucked up!’

She quickly took off the wrapping and pressed it to her pussy. It was cold against her warm, wet sex. She slowly moved it up and down until she felt it catch on her hole. Then she started to push in.

“45 seconds, you better hurry.”

Zoey quickly tried forcing it in, but her pussy stayed tightly shut. Wriggling it around was just making her sore.

“30 seconds. Try and relax, panicking isn’t going to help”

Zoey took a deep breath and closed her eyes. She imagined some of the huge dicks she’d seen online before, and how much they turned her on. She took another breathe and started to lightly push on the cucumber, and it started to move in. She started to pull it out, and then push it in again. It went in further and further each time.

“15 seconds, you better hurry up!”

She could feel her skin starting to stretch around the vegetable. It was really starting to hurt. But she had to try and get it in further. Part of her was starting to enjoy it as well.

She took another breathe and started to push again, much harder this time. It slowly to move in again.

“10, 9, 8…”

“Arghh, it hurts so much”

“7, 6, 5. Just a little further”

Zoey winced as she moved her other hand onto the cucumber, giving it another push. It moved in another centimetre.

“4, 3, 2”

She pushed it with everything she had, and then felt it hit the back of her uterus.

“I’m done! It’s all the way in. FUCK IT HURTS” she yelled at the laptop.

“There’s a good girl. Now be patient, just keep it there a little longer”

Zoey had to hold onto it to stop it from slipping out. She let out another scream of agony.

“Alright, on the count of three, I want you to let go. But I want you to cum before it pops out fully.”

“Ah, ok” she managed to make out between gritted teeth.

“3…. 2….”

“FUCKING HURRY UP”

“1….”

She was in so much pain, she wasn’t sure she could make herself cum at this point.

“And release”

Zoey let go of the cucumber and her hand immediately went to her clit. Her other to her breast where it started squeezing.

The feeling of release was amazing. The sudden release of pressure of the cucumber almost made her cum immediately. But her manual stimulation pushed her over the edge, giving her the most intense orgasm she had ever experienced. The cucumber flew out, along with all her cum squirting over her laptop.

“Uhhhhhhhhh yeeeeees!” she screamed.”

“Hah! I knew you’d love that you little whore. I’ll give you the rest of the day off, but make sure you’re around tomorrow evening at eight. And keep the cucumber, you’ll be needing it.”

The room went silent as the hacker signed off. Zoey saw her background flash and change to a picture of her just as she came, with the cucumber flying out of her. Strands of cum flying out with it.

She sighed as she relaxed, still recovering from her intense orgasm.