Conquests And Pleasures – Chapter 1: Congratulations Jessica

Conquests And Pleasures – Chapter 1: Congratulations Jessica

By: Doctor Doom

Celeb: Jessica Biel

Codes: MF, rape, mDom, bond, nc, oral, anal

Disclaimer: This is fantasy, fiction, not real, etc. This never actually happened, nor is it ever likely to actually happen.

Author’s Note: This story takes place in late 2005 when Jessica Biel was named the sexiest woman alive by Esquire magazine.


Admit it. You wish you were me. As a member of a rather elite organization I have ways of getting what I want. Secretly, my order runs the world.
Nothing of a geopolitical nature happens without our approval. Not that I’m of very high rank within my fraternity, but the resources available to one such as myself allow me to indulge in the finer things in life without any fear of consequences. And my greatest indulgence happens to be women, beautiful women, who one way or another I bend to my will and have my way with. Sometimes, my pets cooperate and we are able to share a moment or two of mutual bliss. On other occasions however, I get to play a little rough with one who doesn’t quite know her role. Allow me to tell you about one such occasion in which I had to be a little forceful.

It was October of 2005, and I was in New York City to celebrate Esquire Magazine’s unveiling of Jessica Biel as their pick for the Sexiest Woman Alive. It was a semi-elegant affair in the ballroom of an upscale hotel in one of the nicest parts of the city. Technically, I wasn’t on the original guest list. Of course though, a man with my connections had no problems arranging a way into the evening’s festivities. It was my plan to see to it that the lady of the hour celebrated her achievement in a way she would never forget.. As you can imagine, I couldn’t just walk right up to my prize for the evening, not with all the other people who were there merely to be seen and wish Ms. Biel the best of luck and all with her new title.

But I had planned everything out perfectly.. Soon, Jessica Biel, the sexiest woman alive would be mine for the taking. Shortly after the editor of the magazine had given a toast for the evening and unveiled a giant sized magazine cover proclaiming Ms. Biel’s new title and achievement I set my plan into action. As she stood on the red carpet next to the giant magazine everyone in the room made their way toward her to congratulate her, everyone except me that is. I would be congratulating her soon enough in my own special way.

As various photographers took her picture and self-important Hollywood types shook her hand, I found my way over to the table where she had been sitting for most of the night. Making sure I wasn’t seen, I slipped the special mixture that I had prepared into her drink. The new ingredient in her beverage would do no actual harm, nor would it render her unconscious, but it would cause her to walk right into the next part of my trap.

With her drink prepared, I made my way to my hiding spot, which was an office off to one side of the main ballroom. Stepping in, I made sure no one noticed me. The room was exactly how I remembered it, a desk to one side of the room, a glass coffee table situated between two large couches in the center of the room, a small bathroom attached to the room opposite of where the desk was located, and a window with large curtains directly across from the door I had entered. I slipped behind the curtains and waited for Jessica to arrive. The drug I had slipped into her drink would make her feel somewhat groggy and lightheaded, causing her to feel as if she needed to momentarily freshen up. Of course, she wouldn’t want to be away from the festivities of the evening too long, and so the bathroom attached to this office would be the closest and easiest way for her to temporarily step away without being too far away from her party.

I waited patiently for about a half hour before she finally stepped into the office. Stumbling slightly over to the bathroom, she stepped inside, having no idea what was about to happen to her. After she had closed the door to the bathroom, I stepped out from behind the curtain. Making my way over to the door between the office and ballroom, I locked it so we would not be disturbed. Now knowing that it was just Ms. Biel and myself, I made my way over to the side of the bathroom door and waited for her to reemerge.

After another moment, Jessica stepped out of the bathroom. She didn’t notice me until I had grabbed her from behind, wrapping one arm around her waist and covering her mouth with my other hand. She tried to scream as I lifted her up off of her feet and carried her over to the back of the couch facing the door out to the main ballroom. She struggled slightly, accidentally kicking off her high heels in the process. The drug by this time had worn off, it had only been meant to allow me to get her in this very situation.

She continued to struggle as I laid her stomach across the top of the couch and bent her over. Leaning my body weight down on top of her, I whispered in her ear. “Hello, Jessica. Congratulations on your achievement. There are a lot of people on the other side of that door, and you probably don’t want them to see you in a situation like this. So just do what I say and you won’t get hurt. Understand?”

She nodded slowly, as it was the only way available for her to respond.

“Good. Now, I’m going to take my hand off of your mouth now, and I don’t want to hear a peep out of you. Are we clear?”

She nodded again, and I removed my hand, fully expecting the scream that came next. I quickly placed my hand back over her mouth, squelching her pathetic attempt to find help.

“I can see you’re not going to entirely cooperate, Ms. Biel,” I said as I leaned over top of her even more, letting more of my weight fall onto her back, pinning her stomach somewhat painfully up against the back of the couch. “Don’t worry though, I have other ways of ensuring you keep your mouth shut,” I said as I reached into my coat pocket and pulled out a ballgag, which I let dangle in front of her face for a brief second before securing it inside of her mouth and around the back of her head.

She tried to struggle, even managed to get out another muffled scream, but it was no use, in a matter of seconds, Jessica Biel was effectively silenced and ready for me to fuck her without so much of another word of protest. Truth be told, I rather enjoy the muffled screams of agonized pleasure that come from my pets when they are in situations such as the one Jessica now found herself in. Completing the sense of helplessness for Jessica came when I reached back into my coat for a pair of handcuffs and pinned her wrists behind her back.

Yes, this was exactly as I had planned things up to this point. Jessica Biel, hands chained behind her back, mouth gagged, her firm, toned body in a sexy white dress bent over the back of a couch, and knowing I was about to have her body in ways she had never imagined when the night began. As a broad grin broke out across my face, I could hear Jessica whimpering in fear over what she figured was about to happen to her.

Placing my hands on her hips, I leaned over her, placing my mouth inches from her ear. I could see her tears falling onto the cushions of the couch in front of her, and whispered soothingly in her ear. “Now, now Jessica, don’t cry. This is your big night. You’re the sexiest woman alive, and I’m just here to help you celebrate your achievement,” I said as I ran my hands up her firm body, letting them come to a rest by cupping her firm breasts.

She tried to scream from behind her gag, most likely thinking to herself that she had never been in a more embarrassing or humiliating situation.

“Now, let’s see,” I said as I began to run my hands back down her body, and down to her ankles. “It took a long time for the magazine to reveal who you really were, didn’t it?”

“Mmmmmmppppp,” she screamed behind her gag. She tried to kick her legs back, attempting to put her heel in my face, but I caught her foot, and continued my verbal torture of her.

“They started by showing a picture of your feet,” I said as I began running my hands back up her body. “Then came your legs, which are of course, attached to your lovely and firm little ass.” I let my hand rest on her firm bottom for a moment before I continued.

“Next was your taut little stomach, and then of course came your lovely breasts,” I said as I once again cupped her fleshy mounds through the fabric of her dress, and began to knead them.

“Mmmpp, mmmpp,” she begged me to stop from behind her gag, and began to cry even harder than before.

“Now, now, Jessica, they really are lovely. Think of all of this as a compliment, a celebration of your body and your new title, the sexiest woman alive.”

By this point, she was likely wishing the editors of the magazine hadn’t picked her for the annual award, but it didn’t matter. Jessica Biel had been on my list for quite some time, and one way or another, her and I were going to meet. Still, the fact that I could torment her with her newly won title made the situation all the more fun.

“Mmmmmm,” she screamed once more.

“Now, please allow me to congratulate you in my own special way,” I said as I knelt down behind her, holding her legs up against the back of the couch to avoid any more of her attempts to kick out at me. Slowly, I slid one hand up the back of her calf, up her thigh, and ran it up underneath her dress. She protested once more, as I yanked her panties down off of her hips and tugged them off of her body. I tossed her panties on the floor in front of the couch, so she could see them, adding to her feeling of building despair, and then, I gently stuck one finger up into her unwilling snatch.

“Mmmmp,” she screamed as I began to slide my digit in and out of her unreceptive hole. She screamed even harder as I placed a second and then a third finger into her.

I know she didn’t want to, but the way I was rubbing her, she was wet in no time, her mind was saying one thing, but her body was betraying her and saying something far different.

“See, Jessica, it appears that we can both enjoy the festivities I’ve planned for us for this evening,” I said as her body shuddered and her snatch sprayed my hand with her warm juices.

“Mmmmpppphh,” she screamed shaking her head back in forth, no doubt hoping I would just stop and let her go back to the party.

“Well, there’s certainly a part of you that has liked what I’ve done so far,” I said mockingly, “and I’m betting that same part is gonna love what I’m about to do next,” I said as I leaned in and stuck my tongue into her snatch.

“Mmmmpppp,” she screamed as her back went rigid.

Even though my head was under her dress, and I was lapping up her juices, I could hear her cries and muffled screams. By now, she had most certainly realized her situation was hopeless. I was going to have my conquest of her body, and all she could do was pray that I’d be quick. Fortunately, for her at that very moment, I would indeed have to be quick with the fulfillment of my fantasy, but it would still be a few minutes before anyone from the party really started to wonder what had happened to her.

I stayed under her dress long enough to cause her clit to make an appearance, which I then focused my attention on from that point on. Nibbling on her little nub, I once again caused her body to give in to my unwanted physical stimulations, and once again, she came, this time on my face.

“Mmmmmpppppp,” she screamed behind her gag once again as her second orgasm hit her even harder than the first.

I stood up behind her, her body slumped over the back of the couch, and I slid her dress up above her ass, as I unfastened my pants.

“Mmm, mmm, mmmmmppp,” she attempted to let out another gagged scream and tried to struggle away. No doubt she knew what I had planned for her next, but her struggles were in vain. She wasn’t going anywhere.

I positioned my throbbing cock at her entrance, and slowly drove it all the way up her warm snatch. I’m sure if it weren’t for the natural lubrication of her juices, I wouldn’t have been able to slide into her as easily as I did. Her back once again went rigid, as my base met her hips.

“Mmmmmmmpppppp,” she let out a long moan from behind her gag, which was obviously more pain than pleasure. Still her body had already started to betray her, and like it or not, there was indeed a part of her that was being forced into enjoying this situation.

No doubt, she had a good look at the door, which led out to the ballroom. And no doubt, she knew that outside, there were dozens of people who would come to her aid if only they knew what was happening to her. But they didn’t know, and she knew they didn’t know. And she knew I knew all of this as well, and that all she could do was continue to cry and hope that it would all be over soon.

She let her body go limp and her upper body fell forward onto the cushions of the couch. I spread her legs wide, holding them under my arms like a human wheelbarrow and began to methodically thrust in and out of her snatch.

“Mmmmmppp, mmmph, mmmppphh,” she screamed behind the gag.

By this point, almost all hope for her was lost, and she just lay there limply, letting me force my way in and out of her body. I started to build my pace faster and faster, and she just lay there without protest, crying harder and harder with each deep thrust, wishing for it all to end.

“Mmmp, mm, mmmph, mmph, mmmmph,” she screamed through her tears as her body once again showed signs of getting ready to betray her. She knew I was going to make her cream all over my cock, the most humiliating orgasm yet, but first, I decided to torment her a bit further.

I slowed my pace, and then stopped for a moment, just keeping my length up inside of her. “Why so down with yourself, Ms. Biel. I told you, think of this as a special congratulatory celebration. After all, you are the sexiest woman alive..”

My words must have awoken the last little bit of fight she had left, because her body instantly tensed up and she began flailing about on the end of my cock like some kind of wounded animal. “Mmmmppph, mmpp, mmpp, mmmmpppppp,” she screamed and tried to somehow pry herself off of my member. Of course, with my cock all the way up her snatch, her hands cuffed behind her back, and me holding her legs wide out to the sides, there was really no chance of her getting free or doing anything at all to improve her situation. In all actuality, the only thing she accomplished was grind her body deeper onto my cock, and causing herself to have another vicious orgasm, which I’m certain is the last thing that she wanted.

“Mmmmmpppp, mmm, mmmm, mmmmppppppphhhhhh,” she wailed behind her gag as she came down from her third involuntary orgasm of the past few minutes, and I began to rhythmically slide in and out of her once more.

Her upper was once again lying limply across the front of the couch as I drove into her faster and faster, harder and harder. She knew what was coming, and she grunted in disgust at the hopelessness and brutality of her situation, “Mmmmmppppp, mmmmmpppppp, mmmmppppphhhhhhhh,” she screamed one last time into the gag as her back once again went rigid from a fourth orgasm as I released my seed up into her.

“Oh yeah, congratulations Ms. Biel,” I grunted as I leaned over her body and let my full load flow up into her unwilling snatch. I pulled out with a sigh and let her body fall forward onto the couch.

I could hear her crying hard behind the gagged as I pulled my pants back up. Knowing that it was now time to go, I spun her around so she was now on her back, causing her to look up at me.

“Ms. Biel, there’s no need to tell anyone what just happened,” I said as she looked up at me, tears rolling down her beautifully sculpted face, with red, puffy eyes still filled with tears of fear and humiliation. “Understand this, if I can get to you at a party in your honor, I can get to you anywhere. And truthfully, there’s nothing you can do to stop me. So what you’re going to do after I take the gag and handcuffs off of you is simple. You’re going to close your eyes, count to a thousand, clean yourself up, and then, go back to your party. Understand?”

She nodded vigorously in agreement to the plan I had laid out.

“Good,” I said as I spun her back around so she was back on her stomach, giving her firm little bottom a hard smack because I could.

“Mmpp,” she gave a short squeal from the spank I had just given her as I undid the handcuffs. I removed the gag next, and like the good little pet I desired her to be, she started doing exactly as I had told her to and began counting, albeit in a whiny and tearful manner that you would expect from someone who had just been savagely raped, “One, two, three…”

With Jessica obeying me perfectly, I turned to the windows opposite of the door, and made my escape. Everything up to this point had gone perfectly.

About an hour later, I sat in the lobby of Jessica’s hotel, pretending to read a newspaper, and waiting for her to walk through the front door. I’ll give her credit, the young lady knows how to act, and had calmed down considerably since I had last seen her. In a very calm and collected manner, she managed to make her way to the front desk and tell the front desk attendant that she was not to be disturbed for any reason for the rest of her stay. If only she knew how easily she was walking into the next part of my plan, I’m sure she would’ve made other arrangements.

I watched as she made her way over to the elevator, and waited another ten minutes before following her up to her room. Her room was on the top floor. Actually, her room was the top floor, a whole executive suite that the magazine was no doubt paying to keep her in during her visit to the city and the party in her honor. Normally, no one would’ve had access to the room but her, but like I already told you, people with my connections have ways of getting what we want. I had to pull a few strings, but I had a duplicate key card that would allow me to spend a bit more time with Jessica Biel.

As I stepped off the elevator and into her room, not surprisingly Jessica was in the bathroom. The door was closed, but I could hear the shower running, as she was no doubt trying to wash away the humiliation from what I had done to her back at the party. I looked around the room; the magazine had obviously spared no expense for the penthouse. Near the bed on a nightstand was a wine bucket with a bottle of champagne in it. Two glasses and a small note also sat on the small table.

Grabbing the bottle and a glass, I walked over to a chair on the other side of the room. I positioned the chair so that I could see Jessica when she walked out of the bathroom. She hadn’t seen me as she stepped out of the bathroom back at the party, but she would definitely see me this time. Hell, at the rate things were going, the poor girl might never go to the bathroom again after this night.

I popped the cork on the champagne, poured myself a glass, and once again waited for her to emerge from the bathroom. This time I had to wait a lot longer for her to come out, over an hour, but the anticipation just made everything that was about to happen even more exciting.

She stepped out of the bathroom accompanied by a cloud of steam due to what must have been a scorching shower. She was wearing a white silk bathrobe, and didn’t notice me sitting in the chair across the room at first. I set my glass down on a table next to the chair I was sitting in, and got her attention.

Her face went white in horror at the sight of me, but rather than just stand there in shock, she had the presence of mind to turn and try to run for the door. Her efforts were useless, as I sprang from my seat and easily caught up to her.

“Nooooooo,” she screamed as my arms once again wrapped around her waist, and I drug her over to the bed. I tossed her down, face first onto the mattress, but she managed to get up and tried to run again. I managed to grab the collar of her robe, but she was able to slip out of it somehow as she once again attempted to reach the door.

It was no use however, as I caught her again, dragged her back to the bed, and fell down on top of her this time so she had no hope of getting away. With her completely naked, I once again pinned her hands behind her back with the handcuffs I had used at the party.

“Nooooo, pleeeeeaaaaaasssssse,” she begged. I reached for her robe and took its silk belt, which I used to tie her ankles together. Once again, she wasn’t going anywhere until I had had my fill with her.

Standing up next to the bed, I looked down at Jessica Biel.

“What do you want from me,” she screamed as tears once again began to well up in her eyes.

“I would think that by now, it would be obvious, Ms. Biel,” I said as I walked back over to the chair I’d been sitting in and started to undress.

“Fuck you,” she screamed.

“Oh don’t worry, there’s plenty of time for that,” I said as I finished stripping down and laid my clothes on the chair, “And this time, we don’t have to worry about being quiet, so please, if you want, feel free to scream.”

“Hellllllpppp,” she wailed as she decided to take me up on the offer to be loud.

“Oh please. No one’s coming to help you, Jessica. You have the whole top floor to yourself, and you’ve asked not to be disturbed. No one is coming,” I said as I grabbed my champagne glass and the bottle and made my way back over to the bed.

“No, stay away from me,” she cried.

A grin spread across my face, “And Jessica, not only can we be as loud as we want, but this time, we can also take as long as we want.”

“Nooooo, you bastard, noooooo,” she screamed and cried, trying to somehow wiggle free from her bonds.

I picked up the note next to the champagne bucket and read it aloud, “Dear Jessica, here’s to your year as the sexiest woman alive. Esquire.”

I sat her up on the bed, and then topped off my glass with champagne and poured some into the other glass. “I propose a toast,” I said as I raised my glass. “To you, Jessica, the sexiest woman on the planet.” I took a sip from my glass, and then picked up the glass I had poured for her. “Care for a drink,” I said as I held the glass in front of her lips.

She turned her head to the side in defiance. “Fine then, have it your way,” I said and poured the glass down over her head.

She cried at the humiliating gesture, and I pulled her toward me to the edge of the bed. “Now, Jessica, I think I’d like for you to suck me off. And don’t get any ideas about biting down or anything, lest you want to have an accident and wait for one of the hotel staff to find you several days from now.”

She sat on the edge of the bed, refusing to open her mouth so I could insert my prick into it. I grabbed her by the hair, causing her to let out a short scream, which I quickly muffled by ramming my cock into her mouth and down the back of her throat. She just sat there, looking ridiculous with my cock in her mouth, stubbornly refusing to even attempt to satisfy me, looking up at me with a look of disgust and scorn..

“Well, I can tell this ain’t exactly going to work,” I said as I placed my glass down on the nightstand, and then grabbed Jessica by the hair. “Here, let me help you out a little,” I said as I began to force her head back and forth along my shaft, making sure to drag my whole rod along her tongue and across the roof of her mouth as I tickled her tonsils with it.

She cried, uncontrollably now, most likely wondering just when this night would end. I pulled out of her mouth, and pushed her back down onto her back. Picking up my champagne glass, I poured the rest of its contents down onto her breasts, stomach, and crotch, and proceeded to slurp the spilled champagne off of her tight, toned body. I nibbled on her nipples, slurped a few drops from her cute little belly button, and then proceeded to once more eat her out once I came to her snatch.

“Noooo, noooo, noooo, unh, uhn, unh, aaaargggghhhhhh,” she screamed and arched her hips into my face as I made her cum yet again.

Standing up over her again, I looked down at her on the bed, “See Jessica, that’s how you satisfy someone orally. It would’ve been nice if you’d tried to give that kind of effort.”

“Go to hell, fuck you,” she screamed.

“You’re so eager to get to the fucking. Well, okay, if you insist,” I said as I placed her legs over my shoulder. She had a puzzled looked on her face, having no idea what kind of position she was in for as I ran my hand over her tight tummy.

“Just fuck me and get it over with, you bastard,” she panted, “Oooooooowwwwwww,” she screamed as I rammed my cock into her ass.

“Take it out, take it out, it hurts, it hurts, it hurts,” she cried. She certainly hadn’t expected anal penetration. I wasn’t sure if it was a new experience for her, but she certainly wasn’t enjoying it.

“I thought you wanted to fuck, Ms. Biel.”

“Not like this, nooooo, ooowwwww, uhn, uhn, uhn, aaaaaccchhhh,” she cried and screamed.

Her pain and humiliation no doubt shot through the roof after what happened next. I held on tightly to her hips, and rolled over onto my back, so that I was now lying on the bed and Jessica was sitting on my cock.

“Oooowwwww, uuuunnnnhhhhhhh,” she leaned her head back toward the ceiling and screamed as her ass sank down to the base of my cock.

I rubbed her breasts for a moment, then ran my hand along her flat smooth stomach once more. “Unnnhhhh, nooooo, noooo, arrrgghghhhh,” she screamed as she sank deeper and deeper onto my cock.

Reaching toward her ankles, I untied the belt from her robe, then spread her legs and put my face back into her crotch, so I was now fucking her in the ass and licking her pussy simultaneously.

“Noooooo, plllleeeasssse, uuuuhhhhnnnnnn,” she screamed at the double stimulation.

Ignoring her snatch for a moment, I started thrusting my hips up into her ass, driving my cock deeper and deeper into her third entrance. “Unnnhhhgggg, ughn, ughn, ahg, agh, uuuhhhnnnn,” she continued to cry in pain and humiliation.

Honestly, the position wasn’t that comfortable for me, and I had only done it to completely humiliate Jessica. With my goal reached, I rolled back over, so I was once again standing over her. I pulled out of her ass, and tossed her down onto the bed, face down and ass up.

“I bet you wish you’d done a little better job of sucking my cock now, Jessica. At least maybe I could’ve slid into your asshole a little easier.”

“Nooooo, just stop, plllllleeeeassssse, uuuuugggggnnnhhhhhhnn,” she screamed as I climbed back over her and reentered her ass.

I pulled her up to her knees, and reached around her body with one hand, plunging my fingers back into her snatch. “Unnnnhhhhhm oh no, shit, fuuuuuuccckkkkkk, aaaarrrrgggghhhhh,” she screamed as I began ramming her back and forth in both holes, digging my fingers deeper into her snatch to force her ass back onto my cock, then thrusting forward into her ass to drive my fingers deep into her snatch.

With my free hand, I reached for the champagne bottle on the nightstand. I took a swig from the bottle as I continued the double penetration of Jessica and forced her body back and forth in the most humiliating way possible.

“Nooooo, stop this, plllleeeeaaaassse, oh no, oooowwwww, uuuuhhhnn, ooooowwwww,” she screamed.

“Who are you,” I grunted and taunted her.

“I’m, uhn, Jessic-aaaahhhh, uhn, Jessica, uhn, Biel, arrrggghhhhh,” she screamed deliriously.

“And what exactly does that mean,” I grunted as I continued to force myself into her two holes and held the champagne bottle over her head, spilling the rest of its contents over her hot, firm body.

“I’m, arrrgghhh, uhn, the, uh, sexiest, uhn, woman, ughnnn,, alive, uuuunnnnhhhhh,” she screamed and climaxed one last time for the evening as I blew a huge load into her tight anal passage, “Uhhhhnnnnnn, uuuhhhhnnnn, owwww, aaaaagggghhhh, aaarrrrrggghhhh, uuuuuhhhhhhnnnn,” she screamed as her body shook and spasmed beneath mine as she unwittingly forced my squirting cock deeper and deeper into her.

Jessica Biel was delirious and exhausted as I pulled out of her, dropping the empty champagne bottle on the bed next to her. I could hear her sobbing uncontrollably as she lay face down on the mattress; no doubt she was conflicted as to what had just happened. Did she really enjoy everything that I had put her through that night? Most likely no, at least not mentally, but physically, I have ways of making any woman lose their mind, even the sexiest woman alive.

By the time I had gotten dressed once again, Jessica had cried herself to sleep.. She’d wake up in the morning a mess, covered in champagne, my cum dribbling out of her ass, and the sheets stained from her own body’s juices. A part of me wished I could be there to see her when she awoke, but I knew I’d have to be content with what I had already done. Still Jessica Biel had been a great fuck, and I’d have to seriously consider a future rendezvous with the young lady. But for now, it was time for me to go.

I retrieved my handcuffs from the sleeping beauty, and gave her a kiss on the cheek before I left. Oh yes, admit it. You wish you were me.

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