White Pineapple, Part 5
Story by All These Roadworks (2021).
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Jaclyn shivered. She was sitting in the passenger seat of a moving car, and in the driver’s seat was the man she knew only as Master - the man with the keys to the hypnotic trigger left by a vengeful ex. A man who could make her do anything.
Behind her, in the passenger seat, were two more men, who she had been introduced to as Ben and Robert, although she was to only refer to either of them as “sir”. Ben was young, with rust red hair. Robert was older, with salt-and-pepper hair and a beard. Both, she had to admit, were quite handsome.
Her Master had turned up at her house that morning with no notice. “Hello, Jaclyn,” he had said. “White pineapple.” And she had shivered, as she heard her trigger phrase. “You’re coming with us on a road trip, Jaclyn,” he told her. “Don’t bring your phone or your wallet - you won’t need them - and for your first choice, you may pack *either* clothes or condoms. If it’s clothes, make sure they please me.”
Jaclyn’s Master liked giving her difficult choices. He liked her to know that whatever degrading and humiliating things happened to her were her choice.
This particular choice made Jaclyn humiliatingly wet. It implied she was going to get fucked - possibly by her Master. She hated the man who had ruined her life - but at the same time the thought of finally having him penetrate her made her shiver with anticipation. He held so much control over her, and yet had never enjoyed her body himself.
She ran to her bedroom and began packing a suitcase. She knew she should pack condoms - she might be fucking strangers, she might fall pregnant - and yet she couldn’t bear the idea of going on a trip, maybe for multiple days, with literally no clothes. So she packed clothes, and left the condoms behind.
But her Master had said her clothes should please him, so she only brought her sexiest lingerie, her shortest skirts, her highest heels, and her tightest tops….
Now she was sitting nervously in a car with her Master and two stranger, on the road to an unknown destination.
“You’re overdressed, Jaclyn,” said her Master suddenly. “You have a choice. You can either take off your shirt and bra and throw them out the window, or take off your skirt and panties and give them to my friends in the back seat.”
Jaclyn blushed, and tried to think quickly. If she didn’t choose, her Master would make her do both….
“Quickly, Jaclyn,” her Master urged.
Jaclyn pictured driving the rest of the way with her tits bare to anyone who looked in the window, and balked. Without further thought, she pulled down her skirt and panties, and passed them into the back seat, blushing as she sat in the passenger seat bare-cunted.
There were chuckles from the men in the back, and Jaclyn watched them in the rear view. Robert took her skirt, folded it up, and put it on the seat beside him. Ben took her panties, and sniffed them, which made her blush. Then he did something more shocking - he unzipped his pants and took out his large, erect cock. He began masturbating - using her panties as a cum cloth.
“Spread legs, Jaclyn,” her Master told her, and, blushing, Jaclyn spread her legs, to let the men in the back see her pussy in the rear view.
“You’re not making very good conversation, Jaclyn,” said her Master. “You should talk to us, don’t you think?”
“Yes,” Jaclyn agreed nervously.
“Here’s a choice for you,” said her Master. “You can either talk about your tits, or your cunt. I want you to describe that body part of you in detail, and tell us why it makes you a disgusting whore. Don’t use any nouns or adjectives that don’t demean you.”
Jaclyn blushed. Again, she knew she had to start talking quickly. “Ah, my tits - sorry, my fuckbags are whorishly large - about a double-D cup. My nipples” - she paused. “Nipples” didn’t demean her. She didn’t know any humiliating synonyms for them. She made one up. “My teat-handles are a little under a centimetre long when my fuckhole is wet and they’re surrounded by” - areolae? - “whipping targets about a centimetre in diameter. Men like it when I use my fuckbags to give them a titjob, and they enjoy squeezing and cumming on my udders. My fuckbags make me a disgusting whore because they’re so huge and because I get wet when people pinch my teat-handles.”
At this last, there was a gasp from the back seat, and she looked in the rear view in time to see Ben cumming into her panties.
“Well done, Ben,” said Jaclyn’s Master. “I think we have another choice for you, Jaclyn. Ben’s decorated your panties for you. Either you can put them back on in the state they’re in, or you can wipe them clean on your face and then throw them out the window.”
Jaclyn twitched with a surge of arousal at this choice. Both options were so humiliating and degrading - but she couldn’t help but picture the sticky wetness of Ben’s cum pressing against her pussy, and feel her cunt wetten in response…
But she also pictured falling pregnant to Ben’s second-hand cum, and decided to play it safe. Red-faced with shame, she took the panties, and used them to wipe Ben’s sperm across her face, leaving a sticky white sheen on her lips, cheeks, nose and forehead. She couldn’t resist licking a little off her lips, and noted it tasted good.
When her Master was satisfied, she threw her cummy panties out the car window, to be lost on the roadside behind her.
Her Master looked over at her. “A man’s cum on your face suits you, Jaclyn. You look pretty like that.”
Jaclyn blushed. She hated the fact that a part of her felt warm and happy at being complimented by her Master. She hated the fact that it made her wetter.
Her Master smiled. “You’re breathing heavily, Jaclyn. Do you need to play with your cunt like a slut?”
“No,” she said, blushing. But she did. She wished her Master would tell her to. But she didn’t want to admit to it.
The car was coming to a small country town. Jaclyn’s Master pulled up next to a small house at one end of the town’s main street, and stopped the car.
“I have a choice for you, Jaclyn,” he said, and Jaclyn tensed, because she could tell from his voice that she was going to hate it.
“Yes?” she asked.
“You can choose between two options,” her Master said. “The first - Option A - is that you can walk down main street, exactly as you currently are, while masturbating. Cum on your face, no panties or skirt, fingers in your fuckhole. It’s the busiest part of the day and I think maybe thirty or forty people might see you. We’ll drive the car to the far end of town and pick you up when you reach us.”
Jaclyn whimpered with horror.
“Here’s your other option,” said her Master. He threw a photograph onto her lap. It depicted a cute blonde, maybe 19 years old, nude, kneeling, sucking an anonymous man’s cock.
“This is Katie,” he said. “She gave me a great blowjob last time I was in town, and was silly enough to let me photograph her. It was an unwise decision, because this is a very traditional town, and she’d be ostracised if anyone ever saw this picture.”
He pointed out the window. “We’re parked outside her house right now, and I can tell you that Katie is home and her parents aren’t. Option B is for you to take that photo over to her house, knock on her door, and use the photo to blackmail her into cleaning your face - and your pussy - with her tongue. Then you can get back in the car without anyone seeing. She’s not a lesbian, and it will be completely non-consensual, and you’ll need to live with the knowledge that you raped a girl because you were too ashamed to let the world see what kind of slut you really are.”
He looked at Jaclyn’s shocked expression. “You have 20 seconds to decide. You can masturbate while you think, but you’re not allowed to cum unless you choose Katie.”
Jaclyn began to frantically rub her pussy. She couldn’t think straight. She couldn’t rape a girl - it was out of the question. But… walking the length of this town, bare cunted, cum on her face, fingers stuffed into her fuckhole - just the thought of the humiliation made her want to cry.
Her finger felt good in her pussy. She needed to cum. She NEEDED to cum. The burst of euphoria from an orgasm would make everything okay.
“Time’s up, Jaclyn,” her Master told her. “Choose now, or I’ll make you do both.”
With a cry of shame, Jaclyn jumped out of the car, and ran up to the door to the house, hoping no-one would see her slutty state. She banged on the front door, and a girl answered almost immediately - the pretty blonde from the photo.
“Hello?” she asked, and then recoiled as she saw the state of Jaclyn’s face and pussy.
Jaclyn held up the photo she had been given. “This is you, isn’t it?” she said. “I need to use you, and if you don’t co-operate, I’ll show everyone in your town this picture.”
“What?” Katie said. “What do you mean?”
“This is man’s cum on my face,” said Jaclyn. “I want you to lick it off me, and then lick my pussy until I cum. If you do that, I’ll go away and I won’t show anyone the photo.”
Katie’s face went white, and her eyes started to fill with tears. She moved back, and let Jaclyn into the house. “Are you serious?” she begged.
“Absolutely,” said Jaclyn. “I’m sorry, I have to do this.”
“You have to?” asked Katie. “It’s that man, isn’t it? The one I sucked off. But he doesn’t make girls do things. He gives them choices. Was this your choice?”
“Shut up,” said Jaclyn, blushing. “Get licking.”
“It is, isn’t it?” asked Katie. “You chose to rape me instead of having to do something else.”
Jaclyn just blushed, and said nothing.
“Fine,” said Katie. She moved close to Jaclyn, wrinkled her nose, and began licking at Jaclyn’s cheeks. Her tongue was warm and wet. She moved to Jaclyn’s forehead, nose, and chin, before finally licking Jaclyn’s lips clean.
Jaclyn couldn’t help herself. She opened her mouth and kissed Katie. Katie didn’t resist, even when Jaclyn pushed her tongue into Katie’s mouth.
When the kiss was over, Katie knelt, and a moment later Jaclyn felt Katie’s fingers parting her pussy lips, and Katie’s tongue teasing Jaclyn’s clitoris. It was Jaclyn’s first lesbian experience, and she had expected to find it uncomfortable and embarrassing, but instead it was exquisite. She moaned with pleasure. After some minutes of bliss had passed, she felt something warm and wet on her inner thigh, where Katie’s cheek was resting against it - and when she realised it was Katie’s tears, something snapped inside Jaclyn, and she orgasmed hard, bucking against Katie’s tongue and squealing with pleasure, before immediately feeling - to her surprise - a second and a third orgasm close behind.
When she returned to the car, she couldn’t make eye contact with anyone inside. She had chosen to rape a girl to spare herself shame. She deserved everything that was happening to her. Her Master said nothing - just started the car and drove out of the town.
After the town had vanished in the rear view, her Master said, “She’s a good actor, isn’t she?”
“What?” asked Jaclyn in surprise.
“Katie,” said her Master. “I bet she made you think she really wasn’t consenting. I bet you didn’t suspect she was a prostitute.”
“Wait,” said Jaclyn. “It was an act? Really?”
Her Master looked at her and smiled. “Does it matter?” he said. “You thought it was real. And you chose to do what you did. I think we learned something nasty about you today, Jaclyn. Something that justifies me being exceptionally cruel to you in future.”
“No…” Jaclyn protested.
“Yes,” said her Master. “Next time you’re crying with humiliation, I want you to remember that you’re a rapist, and you deserve it.”
“No... “ Jaclyn said again.
“I’ll make you a deal, Jaclyn,” said her Master. “A choice, because you like choices, don’t you?”
She thought about saying no, she didn’t like choices, but that sounded like she wanted to be enslaved, so she said, “Yes, sir.”
“Option A,” said her Master, “you can get out of the car and walk home, and I will never bother you again. You’ll be free and clear. Of course, you’ll have to walk a very long way with no skirt and panties, but I’m sure you’ll be fine. But you’ll have to remember every day for the rest of your life that you’re a rapist. In fact, I think I might give you one final command with your trigger, to make you think about it at least once a day.”
Jaclyn squirmed, waiting for the second choice.
“Or, Option B, you can consent to me continuing to torture and abuse and humiliate you, Jaclyn. You can specifically choose to let me keep giving you degrading choices. Everything that happens after here will be because you asked for it. And in return, I’ll use your trigger phrase to make you forget that you raped a girl. You won’t have to think about it again.”
Jaclyn thought. She thought about feeling the crushing guilt she was feeling now every day for the rest of her life. She thought about walking home bare-cunted. She thought about having no more choices to make.
Her Master stopped the car. “If it’s option A, open the door and get out,” he told her. “And if it’s option B, put your fingers in your pussy and say, ‘I raped a girl and I deserved to be abused.’”
Jaclyn took a deep breath. She looked at the door.
Then she put her fingers in her pussy, and said, “I raped a girl and I deserve to be abused.”
Her Master laughed and started the car.
“Good slut,” he told her. “White Pineapple. When I snap my fingers, you’ll forget you raped a girl.,..”
She sighed in relief.
“... and then you’ll masturbate without release until you need to cum so badly you’re begging me to let you do it again,” he finished.
And he snapped his fingers.