Conquests And Pleasures – Chapter 2: Swift Agony

Conquests And Pleasures – Chapter 2: Swift Agony

By: Doctor Doom

Celeb: Taylor Swift

Codes: MF, first, mDom, rape, oral, anal

Disclaimer: This story is purely fiction. It never did and never will actually happen. This story revolves around rape and nonconsensual sex. If this makes you uncomfortable, stop reading now.

Author’s Note: This story takes place way after the events of the first chapter, which starred Jessica Biel, during the summer of 2008. Enjoy.


Yes, we know you wish you could be me. But let’s face it; life hadn’t been
going so great, not since I unknowingly offended the leader of my order. Let’s face it; we both have the same taste in women. How was I to know that he had been saving a particular angel for a special occasion? Since ruining Adriana, my master had had me running several errands for the good of our order. Sure, I had still been able to whet my appetite in the course of redeeming myself, but there was usually a catch. Most notably, I had to gain permission to go on the hunt, as not to make the same mistake twice..

The good news was I was about to add yet another delicious little morsel to my list of trophies. The bad news was I would have to share the young Taylor Swift with several of my fellow members. Of course, there was no reason why I couldn’t have the first taste.

Everything was going exactly as planned, just like it always does when I set my plans in motion. Posing as a limo driver, I had picked Ms. Swift up from the arena in Chicago she had been performing at that night. I had made it appear that I was doing exactly as she expected and heading toward her hotel. Somewhere along the way, I took a wrong turn, which she of course noticed. I played dumb momentarily, and told her I’d turn around right away, which eased her mind initially.

However, after several more “wrong” turns, Taylor began to get the feeling that I was purposely heading in the wrong direction.

“Hey,” she said from the back of the car, “I think you missed the turn a while back.”

“I know,” I said looking at her in the rearview mirror.

She was wearing her trademark look, a simple blue dress with black cowboy boots.

It wasn’t in her nature, all sweet and innocent, to make too big of a fuss. She actually remained quite calm in trying to convince me to turn around.

Whatever she was saying, I completely ignored. Finally, she reached into her purse and took out her cell phone. I had of course planned for her to do this, and pressed a button on the dashboard, which unbeknownst to her, killed the signal of her phone.

As she sat in the back of the car, trying to figure out what was wrong with her phone, I could tell she was getting increasingly worried that something wasn’t quite right. I wondered if she knew she was about to be raped. My instinct told me that she didn’t. She might’ve made a name for herself singing cute little songs about relationships gone bad, but there was never anything in her lyrics that told me she had ever been touched by a man. No, she was just the cute little country girl who most likely never thought of such things. That was about to change.

We finally arrived at our destination for the evening, a small abandoned warehouse outside the city. No one except those who knew what was about to happen would bother coming here. I raised the partition between the front and back of the car before stepping out of the car. As I walked toward the rear of the car, I could hear Taylor trying to force her door open.

She may not have known what she was in for, but she knew something was not right. I could tell she had noticed me standing outside her tinted window. I could hear her yelling, “Hey, let me out of here. Just take me to the hotel, okay.”

I opened the door and poked my head inside the rear of the car. “I’m sorry Ms. Swift, I’m afraid your hotel will have to wait.”

“What, why,” she asked.

“I’m afraid, I’m going to have to ask you a few questions. Now please step out of the car.”

She gave me a puzzled look, but did as I had asked. I grinned; this really would be too easy. “What’s this all about? What kind of questions do you need to ask me?”

“I don’t,” I said as I grabbed her by her long, curly blond hair, “it just makes it easier for me to do this,” I said as I forced my lips onto hers, giving her a long wet kiss.

She gave a muffled scream as our lips touched, and tried to smack me away. After a moment, I pulled back from the kiss and dragged her to the front of the car, laying her back down on the hood.

She struggled only slightly through all of this; still unaware of what was about to happen. Keeping one hand in her hair, I slid a the other up underneath her blue dress, and tore her panties down off of her.

“What? What are you doing,” she screamed, the situation now barely starting to set in, her pretty blue eyes wide in terror.

I looked down at her and grinned, holding her white cotton panties in front of her face before tossing them to the ground. “I’m doing what no man has done before,” I said as I spread her legs wide and stood between them.

“No, no don’t. I’ll scream. I’ll scream,” she bawled.

“Taylor, you can scream all you want. I’d rather enjoy it. And besides, no one is going to hear you,” I said as I unfastened my belt and pulled my throbbing cock from my pants.

It must have taken everything she had to come up with her next sentence through her tears. “Please, you don’t have to do this. You don’t have to,” she said shaking her head.

I removed my hand from her hair and ran it down the side of her face and to her pretty little neck, wrapping it around her throat, just enough to make her aware that I was in complete control of the situation. “Taylor, I never have to do what I do to women like you. But I do it all anyway, because I really, really enjoy it.”

“Noooooooooo,” she screamed as I rammed my throbbing member into her snatch. Just as I had expected, the tip of my cock met with some resistance. I slammed my hips forward, bursting through her hymen, which caused her to scream out in even more pain than before. “Oooooowwwwww, oh god, ooooowwwww, nooooooooooooo, ooooowwwwwww.

I looked down at Taylor, lying helpless on the hood of the limo, with her legs spread and me between them. She looked up at me with total shock, her blue eyes filled with tears. She most certainly had never imagined this would be the way she would lose her virginity.

Her snatch clamped to my cock tighter and harder than any I had ever been in before. As for Taylor, although it was obvious she was in a great deal of pain, it was also obvious that she had never been touched in such a sensual manner.

Her small breasts heaved, partly in agony and partly in reaction to the new sensations she had never imagined up until this very moment.

“Ooooouuuucchhhhh, no, uuuuuuhhhhnnnnn, aaaaarrrrggghhhhh,” she wailed as I began to slowly and methodically drive deep into her warm snatch. “Ooooowwwww, stooooppppppp, uuuuhhhhnnnnnn, aaaaahhhhhmmmmm, noooooo mooooorrrrre, uuuuhhhhnnn,” she screamed as I slowly rocked my hips from side to side, trying to see just how far I could slide up into her and how far I could stretch her out.

I realized it wouldn’t be long before the other members of my order arrived, and I wanted to make sure I had a chance to do to the young singer everything I wanted to do to her. I quickened my pace and drove into her snatch faster and faster.

“Nooooooo, plllllleeeaaaassssse,” she screamed at the top of her lungs, “Ooouuuuccchhhh, uuuuhhnnnnn, uuggghhhhh, uuuuggghhhnnnn, aaaaarrrrrrggghhhhh, ooooohhhhhhhhh” she screamed just as I bottomed out inside of her, her body spasming and shaking beneath mine in ways she likely never imagined it could.

The look on her face was priceless. If this wasn’t the first orgasm she had ever had, then it was at the very least the most intense one she had ever had up to this point in her young life, with her mouth shaped in an O, and her tear filled blue eyes wide in amazement at how her body could feel.

She groaned as I pulled out of her, and she just lay there on the hood. I looked at my watch. I still had about twenty minutes before my fellow order members would arrive.

I pulled Taylor off the hood of the car and placed her on her knees in front of me.

“You ever sucked a cock before, Ms. Swift.”

She was nearing a state of shock. “No,” she shook her head.

“Well, then I guess I better teach you,” I said as I grabbed her by the hair and forced her toward my once again growing member.

“Uhhhnnnn,” she cried as I forced her lips around my tool. “No teeth and lots of tongue,” I ordered her, “and get use to it because I have a few friends that will be arriving shortly and expecting you to know what to do.”

Well, Taylor could certainly have given better head, but under the circumstances, her weak attempt to play with my prick in her mouth would have to suffice.

After a few moments, I pulled her back up and placed her stomach down across the hood of the car.. Hiking her dress up, I slowly slid the tip of my cock along the crack of her tight little ass.

“Nooooooo,” she begged through her tears and clamped her ass cheeks shut tight.

Prying her ass cheeks apart with both hands, I forced my cock up into her anal passage. She continued to squeeze her cheeks together as tight as possible once I got up inside of her, as if she was somehow hoping I wouldn’t actually fuck her third input.

“Taylor, clamping your ass down around my cock, doesn’t really make me any less interested in doing what I’m about to do to you,” I said.

“It’s nasty, pull it out,” she cried.

“Hey, I didn’t slide up inside your ass, just to pull it out. Now why don’t you relax so I can slide in and out a little easier?”

“No, no,” she said shaking her head stubbornly.

“Very well, I think I know a way to get you to relax,” I said as I ran a finger up into her snatch.

“Uuuuuhhhhnnnnn,” she was wet again in no time, and as expected, her body went limp and relaxed after her second orgasm in just the past few minutes.

With her body relaxed and her ass no longer clamping down on my cock like a vice, I proceeded to slide in and out of her with ease.

She was nearing a state of delirium. There was good news and bad news for the girl. The good news, if you can call it that, was I really didn’t have much left in order to fuck her ass too long, finally just shooting a weak stream into her anus that given what she had already been through, she barely noticed. The bad news was my associates were just arriving in a van as I pulled out of her ass.

“Nice going, Willard. Did you leave any for us,” one of my associates said as the group of men approached.

“There’s plenty left, I’ll assure you,” I said as I pulled my pants back up.

“How long you think we got?”

“Two hours, give or take,” I said as I pulled Taylor’s dress off of her and removed her bra.

“Well then, I guess we better have at it,” the man said as he picked the naked and exhausted singer up off the hood of the car and carried her into the warehouse.

A half dozen men went into the warehouse with Taylor Swift, and they stayed in there for every bit of two hours. Occasionally, I’d hear Taylor let out a blood-curdling scream from inside. I had no idea what they were putting her through, nor did I really want to know. As my master had ordered, I waited for them to be done with her, and when they were, I put Taylor back in her dress and drove her back to her hotel.

Taking her through a back door, I took her up to her room, laid her on the bed, and left. Our encounter hadn’t lasted as long as one such as myself would’ve liked, but I was still her first, and that was something to think about.

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END