It was mid morning on Friday and I was sitting in my van as I went over every step of the plan again in my head. It had taken me six months to get to this point and I didn't want anything to go wrong. Isaac would be leaving the office in a little over an hour. I was counting on him sticking to his usual routine of going home at noon and drinking a few glasses of scotch to unwind after a busy week. It was a crucial step for my plan to work. However I had absolutely on control over whether or not it occurred.
At twelve thirty I started the van and headed to Isaac's house. I buzzed the house from the gate but didn't get a response. Taking his lack of an answer as a good sign I used my remote to open the gate. With the way the driveway curved up to the house I was quickly out of view of the street. This meant no nosy neighbors would get a look at what was happening.
Pulling on a pair of latex gloves I used my key to go in through the front door. As quietly as possible I made my way across the foyer and looked into the den. Sure enough Isaac was slumped over sideway on the sofa unconscious. Every thing was going perfectly. Removing the hard plastic case from my pocket I opened it and pulled out one of the two syringes. Fitting a needle to the syringe I crossed the room to Isaac. His sleeves were already rolled up so it was simple to pierce the vain at the inside of his elbow and inject the sedative into his bloodstream. Standing up I left Isaac where he was on the sofa for now. With as much horse tranquilizer as he now had in his system I didn't have to worry, he wasn't going anywhere.
Twenty minutes later I had two of Isaac's suitcases packed and loaded into the van. The pre-typed letter to the CEO of his company saying that he had decided to take an extended holiday was sitting on the kitchen counter with a note for the maid to deliver the letter Monday morning. All that was left to do was load Isaac into the van. Unfortunately it took me longer then I had expected to move Isaac from the house to the van though. I had bought an old paramedic's stretcher to use but I hadn't counted on just how hard 190 pounds of dead weight was to move.
My total time at the house was one hour and ten minutes. That was a full fifteen minutes longer then I had planned. While it was frustrating it wasn't really a problem. I was still on I-45 headed home with my new toy by three o'clock. I would have to stop half way home and give Isaac a second smaller dose of sedative but I would still be home in less the four hours.
Ok a bit of back story is needed I suppose. Isaac is a prominent corporate lawyer. We met when he represented the large pharmaceutical company that bought out the small time drug research company that my parents had started and I was the then CEO of. It was a peaceful mutually beneficial take over so there were no hard feelings on either side of the deal. That being the case, when our new parent company's gorgeous hot shot lawyer asked me out for drinks I said yes. And that as they say was the start of a beautiful relationship.
Isaac and I had been dating for almost two years when everything suddenly went terribly, horribly wrong. Isaac went snooping through my computer. To this day I have no idea what he was supposedly looking for. However, what he found was my secret porn files. This wasn't just your average fuck fest porn though. This was over twenty gigs of hardcore, extreme, and at least taboo if not illegal fetishes. Transsexuals, Femdom, dubious consent sexual torture, you name it I had at least one if not dozens of related videos.
Saying Isaac freaked out would be a massive understatement. When I got home that day I found my wonderful boyfriend of two years franticly throwing my stuff into bags. When I asked him what was going on, he simply pointed at my laptop sitting on the bed. The screen was open to jpegs of all of my videos. I knew right then that our relationship was over. Knowing that didn't stop me from trying to explain. However, Isaac refused to listen. He called me a disgusting freak whore and told me to get out of his house. If he ever saw me again he would use his considerable influence to ruin my life if not make sure I ended up in jail. Heartbroken I gathered my things and left.
I had given up my apartment when Isaac and I moved in together. I had no choice but to head to the ranch that I had inherited from my parents. At some point during the three hour drive to the ranch my heartache turned to anger. How dare Isaac judge me? My possession of those videos didn't hurt anyone. So I was turned on by what some would call questionable or perverse sex. What was it any of Isaac's business? I hadn't asked him to take part in any of these fetishes. It was this fact that got me planning. Isaac had judged me without even knowing how wonderful and freeing these acts could be. If he knew then he would understand.
Within days of my arrival at the ranch I had a basic plan. The first thing I would have to do was modify one of the buildings on the property. After inspecting all of the out buildings I chose the manufactured steel barn a few hundred yards from the back of the house. With a concrete floor, two storage rooms at the back, and slide up bay style door there was very little that actually needed to be done to get the barn ready.
One hold up for my plan was acquiring all of the extras that I would need. I wanted to punish and humiliate Isaac for the way he had hurt me. I also wanted to teach him to enjoy the very fetishes that he had condemned me for. To be able to do what I wanted I needed a vast and varied array of toys and devices. The non sex related items wouldn't be a problem. Most if not all of them I could honestly claim I needed to get the ranch in working order. However, I didn't want anyone to get suspicious of what other then ranching might be going on. This meant that I couldn't have a sudden influx of 'discreet plain brown packages' being delivered. For all that those packages were supposed to be discreet they all but scream PORN. Instead I spent several weeks traveling. I must have gone to every sex shop, fetish store, and adult bookstore in three states. I got everything I needed and then some though.
The biggest hold up though was trying to figure out exactly how I was going to get Isaac and get him to the ranch. I couldn't do the traditional snatch and grab kidnapping. For one I'm only 5'3" and 130 pounds; Isaac is 6" even and 190 pounds of muscle. I wouldn't stand a chance of overpowering him on my own. I also didn't want all of the media and police attention that would cause either. A prominent corporate lawyer snatched from the street, every road out of the city would be crawling with cops and we would be all over the headlines.
Finally memories clicked and inspiration struck. Isaac had threatened me when he threw me out. He was enough of an arrogant bastard to think those threats would be enough to frighten me away for good. I had to test my theory though. I drove to Houston and waited until past time for Isaac to be at work. I didn't bother trying to hide the fact that I was there. If I set off the security alarm I could claim that I was there to get the rest of my stuff from my ex-boyfriend's house. How was I to know that he had changed the locks and or the alarm codes? I shouldn't have worried though. The arrogant bastard hadn't bothered to change the locks or the codes to his security system. In fewer two minutes I was walking through what used to be our house.
At home I drove the van straight into my recently modified barn. If I had measured out the doses of tranquilizer correctly Isaac would be waking up soon. I had at most two hours but most likely closer to one and a half. In that time I had to get Isaac into the proper position, naked and ready. Otherwise I would have one hell of a fight on my hands. The naked part would be the easiest. A few well placed slices of a knife and I could roll him out of his clothes as I positioned him.
It took me just under an hour to get Isaac unloaded from the van, stripped naked, and strapped into the special frame I had built. The frame was an old workout bench of my late brother's that I had modified. Currently Isaac was laying face down with his head, chest, and stomach on the bench. His entire lower half was hanging over the end with his legs spread wide to fit into padded troughs that I had welded to the legs of the bench. Using padded leather wrist cuffs and D-rings I had fastened Isaac's arms over his head to the old bench press support bars. Several buckling straps had also been added to the bench as well as the leg troughs although I left the bench straps undone for now. In this position Isaac could struggle and squirm, but he couldn't escape.
Just as I finished buckling the last strap around his right ankle Isaac groaned. Oh goodie he was waking up. That meant it was almost time to play. I still had a few things to get ready though. Grabbing the rolling metal worktable that I had purchased I walked away. Isaac could continue waking up on his own for a little while.
Crossing to a second fixed worktable I grabbed the bottle of lube that I had made earlier in the day. I wanted to punish and humiliate Isaac, turn him into a quote 'disgusting freak whore', but I didn't want to cause lasting physical damage. Sitting the lube in the center of the table I moved on to the large medal cabinet to select toys for later use. Once again I was momentarily overwhelmed by the sheer number of different toys and devices available. However, another groan and a mumbled obscenity from Isaac was enough to bring me out of my daze. I had made a plan and I would stick to it. Reaching in I grabbed what I needed from the cabinet.
Back in the center of the room I carefully lined everything up on the table in the order I would need it. I could hear rattling and clanking behind me and I smiled. From the noise I guessed that Isaac was finally awake enough to be aware that he was naked and restrained. He was starting to indignantly demand that he be released. Didn't I know who he was? He was fully awake and aware now. It was time for the fun to start.
Being careful to stay out of Isaac's limited range of sight I moved to stand between his spread legs. Thoroughly coating my fingers with the homemade lube I ran my hand through the crack of Isaac's ass. Surprised and confused, he jumped and struggled to move away. As he fought and bucked my index finger caught on the rim of his tight virgin asshole. Quickly I pushed forward past his clenched sphincter, burying my finger to the last knuckle. Isaac roared "AHHHHH! Fuck...ahhh no...stop!"
God I loved the way he screamed. It was like music to my ears. Without giving him more then a second to adjust to having his ass penetrated for the first time I started pumping my finger in and out of his tight little hole. Every time I slid my finger out Isaac tried to clench his asshole so I couldn't push back in. Oh this wouldn't do at all.
Sliding my finger almost all the way out, I slapped Isaac's ass hard as I shoved back in with two fingers. He squealed like a little girl, begging me to stop. "Please stop! You're hurting me. Please I'll give you anything you want." It was such a wonderful offer. He didn't realize just how true that promise was either. He was giving me exactly what I wanted already. His tight little rich ass clamped around my fingers as I mercilessly fucked and stretched his hole.
I could hear the pain in his voice as he pleaded with me to stop. I was hurting him and I knew it. I just didn't care. So instead of stopping, I angled my thrusting fingers down to brutally jab his prostate on every in stroke. As I had hoped this incited quite a reaction, just not the one I expected. Instead of more begging and pleading for me to stop Isaac's cock started getting hard and got harder with each stab to his prostate.
Isaac's obviously reluctant pleasure wasn't something I had anticipated at this point. I had thought it would take hours at least, if not days or weeks before his body learned to derive any kind of enjoyment from the things I was going to do to him. Instead he was already groaning and holding still for me to finger fuck his ass as his cock continued to harden. This was going to be easier and possibly more fun then I had thought.
Gentling my thrusts, I slowed the pounding rhythm of my fingers in his ass. Instead of brutally jabbing my finger tips against Isaac's prostate I switched to softly pressing and stroking the gland. His reaction was beautiful. His cock, completely hard now, visibly twitched and leaked pre-cum with each stroke to his prostate. Muscles that had only seconds ago struggled to push my invading fingers from Isaac's body suddenly relaxed. No longer trying to push me out the muscles now almost seemed to suck my fingers in. Whether he wanted to or not Isaac was starting to enjoy me finger fucking his virgin ass.
Removing my fingers from Isaac's asshole, I applied more lube to my hand. If he liked two fingers, he could handle three. Holding my first three fingers tightly together I shoved back in to the last knuckle. This was still punishment after all. The whimpering moan that this larger, extremely rough penetration tore from Isaac was probably the most erotic sound I have ever heard.
Slowly I increased the speed of my fingers as I fucked them in and out of Isaac. On every thrust I once again pressed and rubbed his prostate. The moans and groans echoing through the barn were now interspersed with stifled sobs. His body was betraying him and he couldn't understand how or why. In less then thirty minutes Isaac had been reduced to a sobbing wreck that had to fight his own body's desire to push back onto my fingers. Things are going much better then I had dared hope.
Despite the fact that Isaac was reluctantly enjoying my fingers fucking his ass, I saw no reason to change my original plan. It was time to move on to the next activity. Suddenly I pulled my fingers from Isaac's ass. His stretched hole quivered as is slowly started to tighten and close. He looked so beautiful tied there shaking as he tried to understand what was going on. Acting on impulse I bent forward and placed a small kiss at the base of his spine. Surprised and even more confused Isaac's whole body jerked at the tender contact.
Reaching over to the rolling table I grabbed my new strap-on rig. A large rubber cock, eight inches long and three inches thick, had already been fitted to the front of the harness. I had removed the small vibrating egg from the inside earlier. Tonight was about Isaac, not me. Quickly strapping the harness on I made sure it was secure and wouldn't slip. I then lubed the large dildo before moving back between Isaac's legs. It was time for step two of the plan. I was going to enjoy every second of it too.
Pressing my left hand into the small of Isaac's back I grasped the rubber cock with my right. Carefully I circled Isaac's tight little hole with the blunt head. He was whimpering and sobbing softly as he shook his head back and forth between his stretched arms. It actually took me a minute to realize that his whimpers were words. He was quietly begging 'Please. Please. Please. Please.' Smiling I caressed Isaac's back gently for a moment. He was so beautiful laying there stretched out along the bench. Standing behind him, getting ready to, for all intents and purposes, rape him with a strap-on; I think I fell in love with him all over again.
Leaning forward slightly I started applying slow steady pressure. I wanted Isaac to feel every centimeter of the thick rubber cock as it penetrated his beautiful virgin ass. Instinct, fear, and pain had Isaac trying to pull away. However, thanks to the way he was strapped to the old workbench he couldn't go anywhere. As Isaac's sphincter gave beneath the pressure of the dildo his quiet sobs and whimpered begging became loader. 'Please. Please. Oh God please. Ahhh...fuck! Ahhh...god please!'
The large head of the rubber cock was now firmly lodged in Isaac's ass. His whole body was shaking as he tried to adjust to being stretched so wide. Slowly sliding my left hand up to between Isaac's shoulder blades I reached down with my other hand to grab his cock. Pain and fear had caused him to go soft. This wouldn't do at all.
Carefully not penetrating any deeper into Isaac's ass I played with his cock. I wanted him as hard as possible. He had enjoyed however, reluctantly having me fuck his ass with my fingers. Now I wanted to make him cum as I fucked him with the strap-on. It wasn't so much that I wanted him to enjoy himself as it was that I wanted to humiliate him by forcing him to cum against his will.
One thing I learned quickly in my relationship with Isaac was exactly how to stroke him to full hardness in minutes. I used that knowledge against him mercilessly now. Still keeping only the head of the dildo lodged in his ass I reached down and squeezed Isaac's cock. Slowly I drug the palm of my hand over his sensitive cock head before wrapping my hand around his length and stroking firmly. In less then a minute Isaac's cock was once again fully hard. It was time to continue with step two.
Still stroking Isaac's cock I slowly leaned forward, putting more of my weight against the end of the dildo. Whimpering and groaning Isaac fought to stop the dildo from sinking any deeper. It didn't do him any good. Instead his movements managed to push his ass back farther onto the rubber cock.
Inadvertent or not seeing Isaac push himself back onto my rubber cock was more then I could take. Bringing both hands to Isaac's hips I pulled him back as far as I could as I slammed my hips forward. Isaac screamed 'AHHHHH...please god!' as six full inches sunk into his ass. Without even pausing I pulled out half an inch before thrusting the last two and a half inches into Isaac.
I only gave Isaac a second or two to adjust. He was still shaking and crying from the shock of having eight inches of cock in his ass for the first time. I honestly didn't care though. I was so incredibly excited by what I was doing that I just started slamming my hips back and forth. With each thrust I was sinking to the hilt before pulling out until only the head of the dildo was left stretching Isaac's abused sphincter muscles. Isaac's whole body jerked with each thrust of my hips. A small helpless yell escaped along with his sobs every time the cock bottomed out in his ass.
Mindless with lust and excitement, I really don't know how long I fucked Isaac's beautiful little ass. I finally came back to myself as my forearms and shoulders started to cramp from my grip on his hips. He was still letting out that same helpless little yell every time I sunk the dildo completely into his ass. However, at some point he had stopped crying and his body had stopped jerking with every thrust. Prying my right hand from Isaac's hip I reached between his legs. I honestly expected to find his cock soft and limp. Instead I found his cock harder then I could ever remember having felt it and leaking a steady stream of pre-cum.
Wrapping my hand around Isaac's cock I started pulling and stroking in time with my thrusts. All of the muscles in Isaac's back and arms tensed as his helpless yells once again turned to whimpers and pleading. 'No don't. Please. No. Please. No...no...no...no...no.' He tried to fight it, he really did. In the end it didn't matter though, his body once again betrayed him. The most anguished shout I have ever heard tore it's way from Isaac's mouth as his cock spasmed in my hand, his ass clenched around the dildo, and his cum erupted onto the floor. "AHHHHH...FUCK! AHHH...ISABELLE!'
Stunned I jerked away from Isaac. This brutally yanked the strap-on from his still clenching ass. Isaac yelled my name again at the painful withdrawal. His cock continued to twitch erratically, his cum leaking onto the floor between his spread legs. All I could do was stand there in complete shock as I watched Isaac's screaming orgasm subside to sobbing whimpers of my name. Two questions kept running through my mind. First, how the fuck could he know it was me? Secondly, if he hadn't known it was me fucking him and forcing him to cum why the fuck had he screamed my name?