Popping a Pop Stars Cherry [with Shocker]

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FormerTomBoy
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Popping a Pop Stars Cherry [with Shocker]

Post by FormerTomBoy »

Image
I will look like Mckenna Grace in the above picture for this roleplay.
I've just achieved history by winning a large number of awards at one of the music industry's oldest awards shows. I haven't yet had to spread my legs or get my knees dirty because I have talent and respect of the industry at the innocent age of 18. I have a good number of stalkers, but my parents, manager and record label have kept my life sheltered from the threats. They would cause me to lock myself in a room and never go out by myself, if I weren't so protected by them.

As I get ready to attend my first after party of the night, I don't change into something conservative because I really love my dress and want to be seen in it. "I'll text you when I get to the party," I tell my mom who still shares a hotel room with me and exit our room to head down the hall to the elevator. I press the button to call the lift that will take me downstairs to the lobby. Then it happened, I feel a hand over my mouth and try to break free as I feel the prick of a needle on my shoulder. I also think I feel another hand cupping one of my small breasts, but I'm unsure as I faint.

[Please PM me, if you'd like to play my kidnapper and stalker for this]
Last edited by FormerTomBoy on Fri Nov 21, 2025 2:43 pm, edited 1 time in total.
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FormerTomBoy
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Re: Popping a Pop Stars Cherry [Available]

Post by FormerTomBoy »

This is still available. Her likeness can be changed for you.
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Shocker
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Re: Popping a Pop Stars Cherry [Available]

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The name is John Walker Tarrington, my friends call me JT and the inevitable smartasses try Johnny Walker. Most of them don’t try a second time. I have been in the business for a long time, but right now my label T-Bird has signed one of the most talented young singers available, she insists on shallow pop songs, but I know one day she will shift to country and really make a killing. I still have her signed for another 3 years, with a contract her tightfisted parents negotiated, the father was an accountant and declined the big initial offer for a steady three year income. Very few do the math, so it’s easy pulling a fast one with a bulk prepayment.

Aside from a great voice, she was not hard on the eyes either, those small tits fit her overall petite built perfectly. But the bitch of a mother had kept her chaperone role to an obsessive level. No way for me to cop a quick feel or impressing my role on the little darling. Well tonight I was going to rectify some of those things.

She looked amazing in that dress, she didn’t see me coming and when the syringe buried itself in her shoulder it was too late. It contained ketamine or not putting to fine of a point on it horse tranquilizer. In seconds it would act as a muscle relaxant, and while she would keep her consciousness, her legs and other muscles would turn to jelly.

She crumpled in front of my eyes. I grabbed her before she hit the floor, getting a good grip on her young tits.
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FormerTomBoy
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Re: Popping a Pop Stars Cherry [Available]

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She is no longer protected by her parents, her manager or her record label as JT prevents her from hitting the floor while taking the opportunity to cop a nice feel of her perky breasts. Her father has a gambling problem that very few know about while her mother has been unfaithful on her father with her manager who is actually on his way to the hotel room to continue their affair. This leaves her to be forgotten as JT has made his move to break her in.

Madison Rhodes is her name and she has no desire to go country as JT has wanted her to do. She wants to follow the path set for young pop stars and feels she can change the path for the good by staying away from drugs and waiting to have sex. She had no chance to think what she was feeling as the syringe took many abilities and senses away from Madison. She couldn't even properly react as she felt a hand on her breast. She had no idea just how bad fame could be for a virgin like her.

Countless posts on the internet have threatened her with rape or sex slavery because she was the latest hot thing in pop music. Maybe wearing a short dress for the first time would be the thing that finally made one of those threats come true. She was even wearing lace panties for the first time after swapping out another pair in the bathroom before exiting the hotel room.
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Re: Popping a Pop Stars Cherry [with Shocker]

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I quickly drag her limp form into my own room which is just a few steps down the corridor. Though dragging might convey the wrong impression, dear little Maddie doesn’t way anything even soaking wet. So it’s not really a challenge to move her where I want her.

And I want her on her back on my bed. Tossing her onto the mattress her legs slightly part and the glittering dress shifts upward, showing me a pretty pair of lacy panties. Just the kind a young woman would wear, who wanted to feel sexy but whose mother does the laundry. The mound they are covering is pronounced. I like that in a woman, it’s so much more comfortable smashing into supple flesh than a pelvic bone. But there was a tine for inspecting both in more detail.


Right now there was the important task of securing her lithe form, I had fixed some of my gaudier ties to the headboard, but I wanted her out of that dress first. Turning her onto her belly and pulling the zipper down, all the way to the small of her back. Feeling that unpacking her would be more pleasing the other way around, I quickly flipped her back again. The straps of the dress were quickly down her shoulders, giving a hint at the roundness of her breasts. I pulled the dress down savoring the reveal of her naked breasts. Of course she wasn’t wearing a bra with that dress, virginal image or not, tits are an asset for a pop star and Maddie knows that.

My eyes follow the path of the dress down her flat belly and the frilly panties. I wondered if her coochie was covered in some fine hair or shaved bald like a slut. Soon I would know. The fabric slid along the smooth hairless legs. Maddie had great legs, I’m from the Kentucky horse country, and I always believed that the legs of a filly told you how they would ride.

Once the dress was off I grabbed her hands and tied each wrist to the bed frame. Then I took a chair and looked at my handywork. There was an empty pillowcase, I had intended to put over her head, but she had seen me, no point in hiding my identity now.

I spoke calmly to her “Maddie, a word of advice the tranquilizers will wear of in a minute or two. Once that happens I advise you to remain quiet, any attempt to scream and I will have to hurt you and gag you. I have brought you here to renegotiate our professional relationship, just the two of us, we don’t need your parents for that. I’ll treat you like a grown woman, as you are no longer a child or minor. Answer me when your ability to speak returns. “
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FormerTomBoy
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Re: Popping a Pop Stars Cherry [with Shocker]

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She was a pop star with no desire to do country music. She was also still a young woman, not far removed from teenage angst years with little real world life experiences. She was coming awake and felt like something had pushed her down a flight of stairs as she went to reach for her head. When she was unable to move her arms, she tried to discover why and was also unable to discover that.

When she heard a voice, she took in the words and did the opposite of them, but as she opened her mouth to scream nothing came out in that moment. Her throat was dry, her mouth lacking moisture and it felt painful to try to speak. She now feared the loss of her talent, but it was simply her body having bad reaction to the situation she now found herself living in a new reality of life.

Her breathing became quick as she was on verge of a panic attack as she finally realized she wasn't wearing clothes anymore. When her vision became clear and the moisture returned to her throat, Madison wanted to call out for her manager, father or mother to save her. "Help!" she choose her first word carefully and decided to take a risk because she was now naked. "Help Me!" she choose to continue as she didn't want to be a woman yet.
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Re: Popping a Pop Stars Cherry [with Shocker]

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I saw it in her eyes, she was going to scream, just millisecond before she opened her mouth. There would be no time to prevent or muffle it. But my body began to react to the danger. My left balled to a fist and pistoned forward, connecting solidly with her tight stomach just as the plea “Help me” echoed in the room. My right had grabbed the flimsy fabric of her panties and ripped them off.

Good that she had tried to be sexy tonight, normal cotton panties offer s lot more resistance. With her mouth still open in pain from the blow, I stuffed the ruined garment between her lips.

“If you want to behave like a stupid cunt, you might as well taste yours.” I looked into her wide eyes “get used to it, you’ll taste a lot more”

The white fabric still protruded a bit from those luscious lips. It was such a pity, I wouldn’t be able to fuck them, but damaging her jaw, Larynx or vocal cords just to get off, wasn’t good business sense. For me she was going to be just two holes and a pair of tits.

Speaking of which it was finally time to look at those assets. I kept s hand over her pantie stuffed mouth. And began fondling her tits, I like them on the small side, so hers were just fine, given the extra benefit of youthful firmness.

I decided to be assertive, and kept my eyes locked in hers as my hand traveled down. Truly terra incognita or virgin country, as I still hadn’t gotten a look at her pussy. I navigated strictly by feel, but I wanted to see her face and eyes as I slipped my finder between the lips that counted. I was far from gentle when doing so.
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FormerTomBoy
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Re: Popping a Pop Stars Cherry [with Shocker]

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She let go a cry as his fist impacted her belly. It was worse feeling she had ever had. She knew he would be giving her more such feelings as he followed it up with another painful offering. Her delicate flesh burned as he rip her lace panties from her form. They were not meant to protect her from rape, they likely were an invitation, if the wrong person found them on her body.

Then she found herself silenced and weakened beyond comprehension as he pushed them into her gaping mouth. Madison would have to grow up fast now. The only good thing she could think of was that at-least now her mouth had been removed from his options. She was still a bright girl, she knew what some girls liked to do with mouth when with a guy. They liked to kiss a guy and she now wouldn't have to do that.

When he covered her mouth even though her own panties were in it, Madison didn't know why he didn't trust the make shift gag until she saw him touching her chest with his free hand. She tried to launch a protest and couldn't as he began to issue her a new form of pain. His touch was unwelcome and she felt strange feeling as nobody had ever touched her breasts in this manner. As he traced his fingers down her stomach, Madison knew she would no longer be a virgin on the night of the award show.

Speaking of award show, she could still recall thanking him and smiling at him in his front row seat as she accepted her awards earlier in the evening. Now she had regrets because of his actions. It must've been her dress that brought him to take this sort of action. Now she felt like she had caused her own assault by teasing him in her short dress. She cried as she felt him part her down there and hated how he was being rough with her.
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Re: Popping a Pop Stars Cherry [with Shocker]

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Nothing like having ones finger up a tight snatch, and little Maddie's was very tight, albeit a bit dry. The recuperative features of teenage cunt, the little slut could fuck a whole football team and be tight like this a few days later. It's age and child birth that take their toll.

But suddenly to my surprise my fingers brushed against a barrier that had no right to be there. I started to out up my biggest shit eating grin. Pushing with my finger against her intact hymen, I looked her in the eyes "Holier than thou Madison, has managed to keep her cherry intact. What did you little slut do, suck off those loser boy friends? Or did you offer them the loop hole, you christian girls love to take it up the ass for Jesus, don't you?"

Her verbal response was unsurprisingly a bit hard to understand, so I continued. "I'm not much of an ass man myself, but if that is your thing we will try that later as well. But I can promise you one thing, You'll never forget your first time."
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FormerTomBoy
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Re: Popping a Pop Stars Cherry [with Shocker]

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Having never done it, she was in great discomfort as the older man began to push into her with a finger. Then another finger added to her already bad feeling. When he taunted her over what he was feeling and asked what she had done to keep herself pure as mountain top water, she could only scream into the gag now in her mouth. He had discovered one thing and that was how she had so far kept at-least two others from having the honor of being her first. She had kissed a fellow young recording artist to draw his mind away from something else and let one radio station GM feel her up when he was reluctant to support her music from day one.

Her mother hadn't been able to keep her completely sheltered to unsavory actors until tonight when she clearly defied set rules. Now she was on verge of losing more than virginity as she could hear it in his voice, this man had more on his mind than just taking her virginity. It then took a threat too her backside for her to become silent with gag in her mouth. She nodded her head in submission, but it was an act she hoped to use to her advantage. She was up to turning the tables, if she could save him from going much further with her vagina.
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