Training Day: Rebekah

Story Info
Senior gets revenge on popular girl.
4.8k words
121.7k
43
12

Part 1 of the 3 part series

Updated 08/30/2017
Created 05/22/2013
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was hard not to see her. She was the girl with the perfect skin, the right curves, great hair, and plenty of attitude. She wasn't the smartest girl in the group, but that never stopped her from being the favorite of just about everyone. Geeks dreamed she would speak to them, jocks hassled each other over who would ask her to the dance, and every girl loved to hate her. Her parents were made of money, but to hear it from her you'd think she was homeless. They wouldn't get her a car until she raised her grades, but who needed algebra anyway?

I hated her, every inch of her perfection. She treated everyone like they were beneath her, walked on them, talked down to them, and worse, others did the same to impress her. It was a disgusting show of the perfect rich girl and her superiority over everything else.

I planned on changing that. I needed a new girl, my clients were slowly becoming bored with the stock that I had back at the farm. A new girl meant finding the ones that deserved to be punished, grabbing them without getting caught, and breaking them in.

I had a plan for her though; a plan to exact my revenge and she would be none the wiser.

Rumor has it that Rebekah is still virginal, teasing her boyfriends until they are at unbearable levels, and leaving them to their own devices. At parties she is never alone, only drinks from un-opened soda cans, and makes sure that she doesn't get cornered by one of her many aggravated beaus. I've watched her for nearly a year now and found the best time to get her alone is to tutor her. She refuses to meet at school since she doesn't want to give anyone ammunition to make fun of her, so she invites her tutors to her house when her parents are away, that way she doesn't have to admit she needs help with her grades, and her parents think she's a good student.

After talking her usual tutor into switching with me for a night so that he could go party with his new girl I had my in. Then was the alibi; my sister was the only help I had in this strange business of mine, but she would happily help. A part of me wonders if she's not even more twisted than our parents were, but more on that later. Now for the plan. After I finished tutoring Rebekah I would leave without incident and head to the pizza place a block from school, always a popular hang-out for students when there were no parties to attend. This guaranteed that I would be seen. As my sister is a quiet, hardly seen geek type, no one will think twice about her. She will sneak into the Rebekah's house as I leave, through the back door I will unlock, by then Rebekah should be drugged into compliance. From there it was a simple walk to the car, and out of town.

Normally I don't consider taking high risk girls for my clients, but this one needs to be brought down a few pegs. Part of the reason I hate her is because I was gullible enough to believe she thought I was cute as a freshman, ended up with naked pictures of me lining the boy's locker room for nearly a year. A not so fun joke she played on me.

At 4:30pm I knocked on her door with her favorite orange soda and sugar free snack in hand. She rolled her eyes when she saw me carrying the food with a snarky, "As if." When she let me in the door. We sat at the dining room table and began her advanced Chemistry homework, soon to be followed by Algebra and possibly Biology. Either this chick never studied, or she just wanted a free pass by having some geek do it all so she could copy it. Not my problem, but I played along. Rebekah didn't touch any of the stuff I brought, which wasn't a surprise, but she was snacking on wheat thins and bottled water when the doorbell rang. She glanced at me and groaned, "Try to stay out of sight." I nodded and got up to hide by the pantry while she checked the door. The moment she was out of sight I grabbed the Rohypnol I stole from my insomniac mother and dropped two in her water, shaking it vigorously to dissolve them quickly. Thankfully she was kept busy for close to ten minutes; the water had calmed down, though it looked a little different, maybe I was paranoid.

Rebekah however was distracted by whatever transpired at the doorbell and so she didn't even bother to look before taking a deep swig from her water, in fact she nearly drank the entire bottle before she noticed any difference, but I had expected sooner.

Looking from the bottle to me and back she threw the bottle at me and bolted for the bathroom, but expecting this I was easily able to grab her, and in her quickly deteriorating condition, pin her to the floor. I took her cell phone from her pocket so she couldn't call or text for help before my sister showed up. I carefully tied and gagged her, carefully dragging her to the back door where the fenced in yard would hide Leah as she carried the drugged beauty to her car. I made sure to straighten the house up before I left, wiping my prints from her cell phone after checking her messages to make sure there wouldn't be a suspicious gap in conversation.

I put her phone by her books, now neatly stacked, and walked out with my back pack over my shoulder, waving as I left, as if I expected her to be watching and headed for the pizza place. I get a text from my sister that she has arrived at the house just as I reach the restaurant. About thirteen people I recognize, though don't really know, are lingering about, a few jocks toss a football back and forth as they munch on greasy pizza. I take a seat and order mini corn dogs, this place has the best kind, and it's my usual order. Don't want to appear suspicious.

Dora the waitress takes my order and nods over at the other guys, "Don't feel like company?" I shrug and tell her they're not really my group of people. She smirks in that sad kind of way that tells you she pities you, and heads to the kitchen to fill my order. Leah in the mean time tells me that Rebekah is safely in the car, fading in and out, she's wiped down the spots she touched, and makes sure all the doors are locked before leaving.

I eat my food slowly, waving at a couple of people I recognize, tossing the football back to the jerks at the other table when they pretend they missed the catch when they hit me with it. At least I know that I've been noticed. I ask Dora for some cheesy fries to go, Leah's studying at home and will be mad if I don't bring her favorite snack home with me.

As I leave I make sure to ding jock boys fender with my car door, a little immature, I'll agree, but it felt good.

I drive for about three hours, making sure I'm not being followed, making sure no one is around when I pull into the long winding drive that takes me back to my family's old farm. We still own the property, but it's not really used anymore, well, not for the normal stock at least.

When I arrive Leah has Rebekah tied to my bed, though Rebekah doesn't really realize what's going on. She's fading in and out of sleep, but that doesn't matter, she doesn't need to remember this part. Leah heads home with her bag of cold cheese fries and leaves me to my work. I take my time, carefully cutting off the expensive clothing I would never consider buying, though I could afford it. I never saw the reason to spend eighty bucks on a pair a jeans you'll probably only wear for a year and throw out.

Anyway, once she is bare to me I check her bindings and begin the fun. I start by taking a soft leather tail whip from my shelf of things and wake her drug addled brain with a stinging whip against her right thigh. She groans and wakes up abruptly, though her mind is fogged and she can't focus, I know that she is aware of the pain. I take the whip to her a few more times, until the skin of her thighs and stomach is pink with irritation. I then replace the whip with a flexible rod that snaps and leaves angry red welts behind. She screams weakly a couple times and pulls at her bindings, but the drug is keeping her mostly sedated.

After she is sensitized I grab a vibrating tool and press it hard against her nearly bare pussy. Her body arcs and she actually seems to be aware of what is happening. I grin and rock the black vibrator against her sensitive clit. I can see her body reacting, though she is trying to get away from my assault. I'm glad she is aware of my assault as I leave the tool propped against her lower lips. I grab a few other toys from my shelf and put them into use. An open mouth gag so she can't bite me later, a set of anal beads that get progressively larger as the strand goes on, and a smaller vibrating tool that is strapped into place against her newly sensitized clit; now I'm ready for the fun to really start.

I make sure to lube the beads good, and moisten my fingers before delving between her sweet cheeks. Her ass is tight, I groan just thinking about the damage I'm going to do later, but for now I start to stretch it out a little, just enough so that the first few beads can slide in and hold. As I push the first two into her ass, she screams against the open mouth gag, my cock jumps in excitement, I push them farther in, watching her struggle against the binds at her wrists and ankles as I push them further in. Tears streak her perfect face when I force in a golf ball sized bead and leave it just in the opening. Her pussy cries as well, but these are different tears, silky warm tears of arousal, whether she wants them or not. I strap the small vibrator onto her and dip a finger into her tight wet sheath as her hips buck from the discomfort of the beads and the high speed vibration.

She screams nearly constant now, a low keening that is muffled by the tears clogging her throat. I grab the back of her head and shove a pillow beneath it; this stretches her neck into an uncomfortable position, but makes it easier for me to straddle her once I shed my clothes. Her eyes widen when she sees my cock standing up right and ready. I smile. "All for you. Payback for the locker room humiliation."

She nearly gags as press my cock into her hot wet mouth, trained as I am in this kind of sex I still felt the need to cum almost immediately. Must be my dreams coming to reality. I started slow at first, and then began an ever quickening rhythm that was sure to leave her bruised. I forced myself to last until I felt her body spasm in orgasm from the vibrating onslaught. It was then I came into her mouth, still sliding my dick in and out of her wet canal, forcing her to choke down my semen.

When I finished I wiped her mouth and took out the gag, replacing it with a ball gag. I spent a few minutes slapping her face, "you're not a tease any more, you're mine, and I'll do with you as I please."

This brought on more tears, but I didn't wait too long before I moved on to her lower lips, drenched with her orgasm, her body still spasming from the toy. I fingered her for a short time, one finger slowly, bending and twisting to make sure she could feel it, then two as I stretched her out a bit. I didn't to remove the vibrator, though it was in the way a bit. I slapped her hard, grabbing her breasts in a painful grip, while rubbing the swollen head of my dick over her weeping pussy. I pinched her nipples hard to distract her just as I penetrated her hard and fast. It hurt her, and I loved it.

She screamed against the gag, but I pushed on, forcing myself deep into her and rocking her hard. I didn't bother to let her adjust, she was wet enough that her body would protect her from most of the invasion. I pounded into her hard and fast, reveling in the feel of her body arching against the pounding onslaught of mine, feeling her muscles jerk with orgasm, and eventually going limp when she could take no more. I pulled out before cumming myself and walked around the bed, pumping my own dick I shot it onto her face and left it as I cleaned myself up.

When I came back out wrapped in a towel I couldn't tell if she was sleeping or passed out from the ordeal. I took the vibrator off and tossed it aside to be cleaned and removed the ball gag. I left the bead in her ass though, I thought it looked like a funny tail and she needed to be stretched out. I had one buyer who loved young ass.

I called Mark and Clyde, my guys at the barn, and they came by and grabbed Rebekah, carrying her the 50 yards to the barn where I instructed them to tie her up. They ran a thick rope around the rafters and tied it to the chain of an old heavy set of manacles before locking her into them and hoisting her so that her toes barely touched the ground. I left her there to hang. As I left I glanced back and noticed the bead hanging, as good as I felt I wasn't done yet. I placed a hand around her waist and grabbed onto the beads, slowly pushing them deeper by nearly three beads. Her ass would be sore, but by morning, she'd be ready for the second part of her training.

*

Training Day: Part 2-Rebekah's First Client

As I woke my first impression was cold. The air on my skin caused goose bumps to rise all over my skin. The second thing I noted was that I was naked, and very sore. My head was heavy, foggy. Thoughts came jumbled and incoherently, but this faded after a few minutes, at least I think it was only a few minutes. My shoulders ached, my jaw felt bruised, and my body was very sensitive. As all of these realizations hit me so did the memory of the previous night. I had thought it just a horrible nightmare; Brandon had all but fucked me with his eyes while he'd tutored me, it was aggravating, and disgusting.

It seems he'd done more than just use his eyes. My body ached in all the right places to fill in the blanks of my memory. He'd drugged me, but I'd been too arrogant to notice at first. Never once thought anyone would try something in my house, but that was my first mistake. Now, as far as I can recall, I could be pregnant with the king of geekdom's baby and apparently he wasn't done with me yet. As I raised my head to look around my shoulders burned and since I couldn't feel my hands I figured I was tied with my arms above my head. I didn't realize I was hanging until I tried to turn around to see where exactly I was and found that my toes barely touched the floor. I screamed, no way out, no control; this was so not happening to me. I would kill that idiot nerd who dared do this to me! If he was taping this to embarrass me I would take him to court and make sure he spent the rest of his life being ass raped in some medium security prison.

It was just after I stopped screaming that I heard another voice near me. A soft female voice, well, soft only because she whispered. "Stop making so much noise. I know it's scary when you're new, but if you're good you won't get punished." I couldn't see the girl who spoke, but her words just pissed me off, "Who are you and why are you helping him?! When I get out of here you'll go down with him you little bitch." The girl laughed a little, but stopped whispering, "You're never getting out of here, but your attitude will land you in some seriously bad places."

I wanted to scream at her some more, but I heard the door open nearby and waited. Two big guys came walking around me shortly after, their large paw-like hands like branding irons on my cold skin; they lowered me to the ground. I couldn't feel my legs, and my arms were very rubbery, being held up by the two gorillas was a blessing but I hated their hands on my naked skin. "It's about time you got here. Did daddy send you to find me? Where are my clothes?"

The black brute just chuckled a little and threw me over his shoulder while the blonde one slapped my ass hard, "We're not hear cause of daddy, we're here cause the boss sent for you. You need more training because he's got a buyer interested in your sweet ass." I was horrified!!! I kicked and screamed, but that only got me spanked again. My butt was already sore from something, and the slapping caused a stinging ache that didn't go away. It was then I realized that I either had to poop badly, or something had been stuffed in my ass. The latter proved to be true when I was all but dropped onto a cold, padded leather table and held down. The big black man pushed forced my legs apart and held them wide as the blonde guy started pulling on a long chain of plastic beads that had been hanging from my ass. I was mortified. The pain was moderate, the friction of the beads moving inside me was both awkward and stimulating, I felt my nipples start to tighten, so I kicked out at the bear of a man holding me down. He caught my leg and held my knee to my chest, this caused my sphincter to tighten around the beads. It hurt, but also felt oddly good. I didn't understand this, but was unable to do much to fight back. The blonde guy dangled the beads in front of me and I saw a little bit of smeared blood on a few of the beads. This infuriated me more and I began to thrash against the black man. The blonde dropped the beads and locked an arm around my neck, forcing me against the table.

I heard Brandon's voice then and fought against the pressure on my tired arms as they were tied to the board I lay on. "The more you fight the more punishment you'll receive. There is no one here that will help you. If you're good, and obey, you'll be rewarded with luxury. If you are bad you will be punished in ways you have yet to imagine." He grabbed one leg and tied it down as the black man grabbed the other and did the same. I was stretched out with my legs tied over a table, my butt hanging over the edge. Ugh, this so reminded me of the Ob-Gyn when I had to get a pelvic exam done when I turned 18. That thought fled my mind quickly as clamps were clipped onto my tightening nipples and clothes pins pinched onto my skin along my stomach. I tried to buck away from them at first, but that caused the clamps and pins to jerk and pull on my sensitive skin, I could also see the three of them becoming very excited. "Let me go, Brandon, I'll never tell anyone you did this if you let me go." Brandon only laughed at me, "You think I'm a fool? Besides, why would I let my newest prize go? I have a new client, and he's looking forward to meeting you. If you're a good girl I'll let you rest before your client arrives. If you don't cooperate I will wear you down so you don't have a choice but to comply. It'll be better for you if you go along with it." I saw him nod at the blonde guy who then forced a ball gag into my mouth. It tasted funny, like brand new plastic and something else I couldn't place. The clamps on my nipples were connected by a thing silver chain that blonde man kept pulling at. I could feel my body ripple in reaction each time he tugged on it, I was so pissed that I felt anything. Only a whore could enjoy something like this.

The three placed so many clothes pins from just under my breasts down my stomach and hips to my thighs that I lost count of how many there were. When they were done they would occasionally flick one, cause me to whimper in pain. My body however reacted in a completely different manner, and I couldn't hide it. I felt myself grow damp and slammed my eyes shut, not wanting to see their reaction, I heard it though. "Little bitch likes it" came from the black man. Brandon chuckled and slapped my left breast, causing both of them to bounce painfully, "I knew she'd make a good pet." The blonde grabbed my throat and pressed my head back over the edge of the table I was splayed on, "You're gonna love it here sweet cheeks."

I groaned again, fear, pain, and humiliation making me wish for death, quickly. They had only begun though. It seems the man who purchased me enjoyed hardcore BDSM because they attached another clamp to my tender clit and ran a chain up to the one that connected to my breasts. Then they added these little shock clamps to the chain, and each time they pushed the button on their remote a little shock hit my nipples and my clit causing me to buck against my restraints. My body flushed pink and my clit swelled as I came hard seconds into this new torture. I felt tears trail down my face, embarrassed that my body could react this way.

12