Cassandra

All characters are 18 or older and completely fictional.

Cassandra

Chapter 1

Her name was Cassandra, she was 18 and a senior in highschool. I had stalked her for nearly three months before I decided today was the day. I waited for her in an alley she uses as a shortcut home from school. I often sat there pretending to be on a call with my car on most days and she had even seen my face walking by. I smiled and she smiled back. She was of light ebony skin color, with frizzy wavy hair. Her height was about 5'5" and she was fairly lean. She ran track at Luckins High School in Wimberly.

She was the first one I ever took. It was harder than I expected, her running wasn't a problem as I had snuck up behind her. She had passed me every day walking home from school for nearly 3 months now. So there was no reason for her to wary that I was parked in the alley. I wrapped my arm around her neck and covered her mouth with my other hand. What I didn't expect is how strong she was as she tried to throw me over her shoulder, the sudden jerk forced me to let go to catch myself. She screamed and attempted to run, my heart begun racing, I quickly grabbed her leg and pulled as she took a step and she tripped and fell head first onto the pavement and fell unconscious. As I was now in a hurry fearing someone had heard her I didn't tie her hands or mouth as I had planned and quickly stuffed her in my trunk and drove off.

She woke up somewhere along the highway, I could hear her start yelling and knew I had to pull off the road and at least bind her hands and mouth. There was a small road going off into the woods that would suffice. I opened the trunk to her dark brown eyes as wide as they could be and she didn't know if she should scream or not. Before she could decide I grabbed her and threw her out of the trunk and onto the ground. She began to scream but no one could've have been within at least 20 miles of us. I wrapped a rag around her head to gag her, but she jerked her head to stop me. I had to nearly choke her out completely to get it on. I decided I had time to tie her up how I wanted and tied her feet together, making sure that there was no way the knots could come undone. I tied her hands behind her back and fixed the strip of cloth gagging her mouth.

I took this opportunity to examine my prize, I needed a taste. I lifted her up and placed her upper half into the trunk with her feet still on the ground, I reached over her felt her B Cup breasts, she starting to scream as she knew I didn't want her for money, I wanted her for something more dark. I proceeded to fondle her as I reached under her waist and undid the button to her jean shorts. I pulled them down to see her lavender underwear. I caressed her snatch to the point I couldn't resist. I pulled her panties down to her thighs and saw two beautiful plump lips, two thin inner lips and a small ball at the bottom. I spread them to see the sweet pink color.

I brought my hand up and rubbed her clit and bare pussy until finally bringing my hand up and sticking my index and middle finger inside, she squirmed and continue to scream but I knew it wouldn't matter. She was mine. I fingered her for what seemed like hours but in reality, was mere minutes. I had thought she was no longer a virgin, but I could feel a wall inside her. There were times she was with her boyfriend, and I presumed they were having sex but I had been wrong. I was going to be the one to deflower her. I stood and unzipped my pants.

She went quiet. I pulled my pants and boxers all the way off and lined up. My tip slick with precum. I put my tip at the entrance to her pussy and entered just enough to hit her hymen but not break it, I teased her here just barely putting pressure on her hymen. I felt myself about to explode, but I wouldn't let her first time be this fast. I put my hand in the middle of her shoulder blades and pulled out to barely spread her opening.

I thrusted hard, harder than maybe I should have, but it broke her hymen.

She let out a high shrill as I went all the way to my base. If I hadn't have held her down, she may well have hit her head on the top of the trunk. Now all the way inside her I could feel how tight she was, I didn't know if it was her clenching or her just naturally being tight, probably a bit of both. As I begun to pull out, I noticed the trickle of blood down her thigh, pooling onto the side of her underwear.

I came all that way out and then lined back on her and thrusted all that way back in. I did this several times, letting her know I owned her now, that I would use her when I wanted, wherever I wanted. I begun to pump her with my hands on her hips, I noticed she started to get wet, her body reacting the opposite of her wants. I knew she must not have been enjoying this even if her body was.

The inside of her thighs were moist now and I knew I couldn't hold out much longer. I pumped deeper into her now, she stopped trying to resist at this point as she knew nothing would come of it. I could feel myself about to cum, just a few more thrusts. I thrust one last time as deep as I could and poured my seed deep into her cunt.

I stood there for a minute listening to her sob with my member still inside after I had inseminated her. I finally pulled out and watched the mix cum and blood drip from her pussy to her panties.

Noticing how dark it had become, the sun hadn't set yet but it was going to soon, I lifted her panties back over hips and watched our fluids put another stain inside them. I patted her panties against her cunt a few times feeling the wetness before pulling up her shorts and buttoning them back. I didn't want to let all of my hard work just leak out.

I lifter her legs into the trunk and looked her in the eyes before closing it on her. I got into the driver seat and turned the engine over, turning around and beginning the drive back to my cabin.

The drive took the better part of an hour but was mostly highway, except for the gravel road about a mile long leading up to the residence. I clicked the garage button and drove in then pressed it again to close it. I opened the trunk to see her tear swelled eyes looking up at me. I grabbed her and tried to get her out of the trunk but she seemed to have some fight in her after the rest over the car ride. I stopped and looked at her in the trunk with fear in her eyes. I shut the trunk door and walked into my house.

I came back the next morning knowing she would be exhausted from not having any food and being crammed in my trunk for over 12 hours. I went back to the garage and opened the trunk. I took a different approach this time and opened the trunk while holding a utility knife. She looked at me with anger in her eyes thinking she had won last night, at least until she had saw the knife. She squirmed farther back into the trunk but i grabbed the know on her legs and pulled them towards me. I cut the knot with the knife freeing her legs and she looked at me surprised.

I told her "I do not wish to harm you in that way." and reached for her face. She was reluctant to let me cut the gag off of her but in the end, she didn't have enough energy to resist. "Get out. I am not going to fight you."

I backed up and slid the blade back into itself. She had already put her arms under her legs to have them in front of her. She grabbed the edge of the trunk and lifted her legs onto the ground.

"Do you need any help?" I asked.

"No, thanks" she said with a glare. At least she was talking, I didn't expect that for some time, at least not the first day.

She stood after she got out of the car and looked around.

I told her "Walk to the door, your room is on the far end of the house." I walked behind her as she made her way to the door.

She had not seen my house yet and was probably expecting some rundown barn. She walked through the doorway and into the kitchen. It was a beautiful kitchen with blue granite counter tops and a gas oven and stove. Lights overhung the stove and island, I even had custom lights hung from the ceiling over the dining table.

Waiting for her there was a breakfast made by my maid. Her name was Natalie, she would be the one making sure Cassandra ate properly, stayed hygienic and would go out and buy clothes and toiletries for her. She had been my best friend for a long time and knew what I wanted, even though she would never lay with me she said she would support me in all my endeavor's.

Natalie and I ate breakfast with her and got her moved into her room. Her room was probably a lot nicer than she expected but I didn't expect any compliments. She had a queen sized bed with a pillow top mattress, she even had silk sheets. The room was about 12' by 15' with complete sound proofing on the walls, doors, windows, and even vents (Which costed a lot more than I care to say). The room was carpeted, and the walls painted her favorite color, a nice spring green. She had an eloquent master bath with a corner tub with all the highest quality shampoo's, conditioner's and body washes. On one side there was a walk in shower with rain head above and three removable showerheads on each side. The other wall contained a full walk in closet with whatever she could imagine, I told her if there was anything specific she wanted to just tell natalie and she will pick it up for her. There was a laptop and television in her room, we had every channel she could ever have and if she became trustworthy enough, I would even allow her to other parts of the house. The entire house was being recorded at this moment and sent to a room where one could watch her. I even had a straight feed to Natalie and I's phones so we could be watching her making sure she didn't try anything.

By the time night fell I was feeling horny again. So I decided to pay my new prize a visit. I didn't knock on her door (which was an iron door about two inches thick) because i wanted her startled as I entered. She jumped up off her bed and dropped the magazine she was flipping through. "Get on the bed belly down."

She looked at me sternly "I won't do what you want, my parents will find you and my dad will kill you."

"If you fight me, you will just make it worse, now I won't ask again." She stood her ground.

She had balls I'll give her that, but I was much bigger than her having over 70 pounds on her and nearly a foot of height I took a step towards her. She put her hands up like she was going to box me, I continued walking towards her and as I got within arm's reach she swung hard and hit me square in the jaw. I expected her to hit me and was prepared for it, but she is a lot stronger than she looks and quick too. She nearly hit me again when I dodged her left hand and spun her around. Having her arms crossed bear hugging her I took a cuff off my pants and caught her arm. I moved her to the bed and locked the other side of the cuff to the frame. I did her other arm to the other side then proceeded with her feet. I cut her clothes and undergarments from her and stared at her naked body.

"This would have Been a lot more pleasant had you done what I asked." I stripped and crawled on top of her, kneeling over her thighs. I spread one of her cheeks to the side so I could see her balloon knot sphincter. I licked my index and middle finger and rubbed the outside of her asshole. She screamed as I moved my fingers down to her pussy.

"No one can hear you in here, not even Natalie." I stuck my fingers in her and took them out and licked them again. Moistening her asshole more I stuck my middle finger in just past the nail. "This is the part where you should've done what I said."

I grabbed my now erect cock and placed it on her anus. Putting all my weight down on her forcing myself into her she shrieked even louder than before. I could feel her squirming under me to try and get away from the pain. I lifted up and thrust down again, and again until she had passed out from the pain, which took only a few minutes.

I sat up while still inside her and spread her cheeks. I pushed and pulled her towards and away from me. Her unconscious body relaxed her holes making it easier to slide in and out. She awoke a couple minutes later and didn't seem to realize what was happening. She looked back and her facial expression when from fear to pure dread as she saw me still on top of her. "You are much looser when you are relaxed, maybe just try and enjoy it and it will be more pleasurable."

"Fuck you!" she yelled back.

I thrusted as hard as I did the first time just to make her shriek again. I began to pump her again watching her cheeks make waves every time my body hit hers. I fucked her for over an hour before I felt an orgasm coming on. I unloaded the first few shots deep into her ass the pulled out and shot the remaining load onto her back and buttocks. As the last of my cum was slowly coming out I pressed into her vagina and watched her anus slowly ooze my seed out. I pulled back and got off the bed, I began putting my clothes back on as i watched the cum drip to her pussy. I left her tied there.

As I was walking back down the hallway I saw Natalie. She would be coming to help Cassandra clean up as there is a buzzer installed on the door that alerts the house when it is opened. "Don't clean her up this time, I want to teach her a lesson." Natalie turned around and went back to her normal chores.

The next morning had set I decided it would be a good time to return to Cassandra. I entered the room and saw her lying their sobbing. The Sun illuminating the entire room and her bronze skin. The dried cum on her back had started to flake off her and whatever was near her holes had been rubbed off from her legs.

I greeted her "Good morning, are you ready for the second part of your punishment?" I undid one cuff then tied a slip knot around the limb I just freed, this time tightening the binding so that it was pulling her to where she couldn't pull away too much.

"What are you going to do to me?" the fear still in her voice. I brought out a vibrator and placed it under her clit.

"You'll see in just a moment" I flipped the switch on and left her there. I took a chair from under the desk and observed her. It took about ten minutes before her pussy started to pulse, I could also start to see her juices flowing. It was just a glisten at this point but her contractions were getting stronger. She was beginning to try a tilt her hips up to avoid the vibration. As she did this I got up and resituated the vibrator.

Her pussy reacting in the exact opposite of her face was enough for me to want to touch her. I stuck my index finger in her and she let out a quiet moan. She must've resented being horny at this moment, but I couldn't blame her. That much sensation would do that to just about any girl. I stuck in my ring finger along with my middle and began slowly fingering her in tandem with her contractions. She begun to push off and then back on to the vibrator, I took my hand out and wet my thumb. Stuck my hand back down behind her but this time while fingering her did a circular motion on her anus. I moved my fingers faster and felt the contractions squeeze tighter, she let out an audible moan and I felt her quiver. This was going to be the first orgasm of many this morning.

I wasn't done yet though, I wanted to make her bed soaked. I tiny spot had already formed from the wetness flowing from her, but I wanted her to feel the wetness on the sheets after I leave her there. I loosened the ropes and pulled her up to a doggy style position. I switched the vibe to the highest setting and went back to fingering her while holding the vibe against her clit. This time moving my hand up and down instead in and out, this way I would hit her g-spot.

She let out a quiet grunt every time my fingers would reach it. It wasn't long before her pussy was convulsing again, this time even harder than before. I moved my hand as quick as I could until she moaned with pleasure, she stuck her ass as high as she could and let out a jet stream of water onto the bed. I quickly took the vibrator away and let her have this orgasm. Slowly spreading her knees as she squirted moving her pussy back to the mattress.

Her hole was opening and closing furiously from her orgasm, but before she had time to recover I took my boxers off and got behind her. I lifted her back up while her pussy was still convulsing and put the vibe back on her clit from underneath. I took my erect penis and slipped it into her with ease. While still holding the vibe onto her I began to hump her. She let out a whimper every time I went in and it only took ten pumps to make her squirt again. This time grinding up and down on my cock.

She orgasmed multiple times in the next 30 minutes, pushing back onto me and grinding against me each time. Her asshole had started to pulse as well, and I reached over to her face. Taking her mouth by surprise with my thumb, she didn't have a chance to try and bite it and I didn't even know if she would want to at this point, I stuck it in her mouth to moisten it. I brought my hand back behind her and stuck my thumb in her ass. I began humping her again while thumbing her asshole. She came again, the fluid jetting out became less and less with every orgasm. I felt my own orgasm coming on, and began to push against her harder. I could feel her squeezing me every time she contracted. I thrusted as deep as I could and she poured herself all over the bed once again as I filled her pulsing cunt.

I withdrew my thumb and cock and took the vibe off of her. I undid the knots on her arms and legs and watched as her cunt pushed out my seed as she tried to recover on the bed. Her breath become normal as her cunt went back to relaxing. She laid there in a pool of her own cum while my own leaked out of her. The wet spot on the bed was wide enough to reach the ends of the mattress. As I left, I let Natalie know we would have to order a new mattress.

The first week was annoying as she tried to escape a couple times, once through the wall only to be met by the brick wall within it. I rushed home to stop her, but she had already torn most of the drywall off the wall. The other time she broke her desk chair trying to break the bullet proof windows. The weeks after that she slowly got adjusted to living here.