I wrote this for one reader specifically. She knows who she is. I hope that you like it.
Jack Singleton made his way toward the house, blending in with the shadows, and using the brush as cover. He was dressed in black from head to toe. If anyone saw him, which no one would, they would know that he was up to no good, the cops would most definitely be called, and his mark would escape untouched.
Jack admitted to himself that this was the best job he'd had in a long time. It came down from a source that he didn't hear from too often. He didn't know who that was, he never knew who any of them were—it was safer that way—but this one only gave him an occasional job. This job was unconventional. He was to rape a sixteen-year-old girl. That's what the orders said. It's not all they said. They said to leave as few marks as possible, and not to cause any permanent damage. All of that was just fine with him. Piece of cake so to speak.
The dark figure approached the boundaries of the mark's home. Everything looked dark. There wasn't a single light on in the house, or surrounding the house. It couldn't get any easier. The house was fairly large. It was two stories, and the exterior was well decorated with lavish trim. There was a pool out back, which was surrounded by a high privacy fence. Whoever the owners were they definitely had money.
Jack's mind went to the picture of the girl. According to his orders her name was Allyssa. She was cute for sure, and even though her appearance was innocent on the surface, he thought he could sense a little bit of wildness in her eyes. Whoever the girl was, she wasn't who her parents thought she was, that was for sure. Then again parents always thought there children were angels.
Jack continued to survey the house. He picked out a bush that was close to a large window, and made his way to it. Once he was there he peaked inside. He could see a large leather couch, end tables, lamps, coffee table, and large flat screen T.V. If he were here to rob, like he did in the old days, the place the T.V. Would make for fine loot. He wasn't though, and his eyes went back to the couch. It wasn't empty. He could see the form of someone laying on it covered with a blanket. He watched the figures breathing pattern. She was asleep. The shape and size told him that this was probably his mark.
He made his way around the house, checking it out, looking for the easiest entrance, and gathering bits of information. The garage seemed to be empty, and there was only one vehicle in the driveway—an older S.U.V. Probably the mark's. There was a good chance that she was alone.
Could it be any easier, he thought to himself.
Jack could only find one thing that would be a challenge, but his orders even simplified that. The house had an alarm system, but his orders had the code. Pick a lock, and enter a code. No big deal. The only possible issue that he could see was that he was a day early, but how big a deal could that be. He had another job tomorrow, and it payed more than this one. This one he would do for free if being a day early was a problem.
When he got to the back—the safest place to gain entry—he made his way to the back sliding door, and dropped his pack quietly to the ground. He moved swiftly, with a practiced grace, and quietly. Jack checked the door and, to his surprise, the back door was unlocked. He slowly slid the door open, entered, grabbing his pack on the way, and slowly slid the door closed.
It wasn't until then that his heart quickened his pace. It was this part of any job that he enjoyed most. He took a deep breath and let it out slowly. He willed his heart to slow, which enabled him to think more clearly. Adrenaline rushes were awesome and everything, but sometimes they messed with your ability to think things through. Better to lose the rush than to die doing a job.
Jack made his way through the house, barely making a sound, and checked it out more thoroughly. If anyone was in the house he needed to know about it. He had stuff in his pack to knock them out for the night, but he hoped he didn't need it.
He was in luck. The house was empty other than the one person he came to see. He made his way to the living room.
Jack stood in front of the girl, and watched her sleep for a minute. She looked so peaceful. The blanket was pulled up to her chest. She had a fist full of the blanket tucked up under her tanned chin. Her dark wavy hair was strained by the sun, but still beautiful.
“Yep,” he thought, “sometimes I have the best job in the world.”
Jack bent and slowly unzipped his pack. He quietly brought out the things he needed and set the bag aside. It was almost time to wake sleeping beauty.
Jack tucked a length of rope into one back pocket, and a ball gag into the other. He grabbed another smaller length of rope from his pile of supplies, tied a slip know with a loop in it, and slipped the loop over his wrist. He allow the rest of the rope to fall to the floor, and he made the final steps to her resting spot.
Jack took a deep breath and calmed himself again. His heart was beating fast now, but as before, he needed all of his thinking power.
With a single agile movement Jack grabbed the girl's exposed wrist, allowed the loop to fall over her wrist, and he tightened it. The girl awoke with a scream and he covered her mouth with his free hand.
“This will go a lot easier if you don't do that again,” he said to her. “I don't want to hurt you, but if you scream again I won't have a choice. Do you understand?”
The girl looked up at him with pleading eyes, but shook her head yes.
“Are you going to fight me?”
Her eyes were wide. She was definitely frightened. She thought about it for a second and shook her head no.
“Good,” Jack said. “Very good. This can go very badly for you if you fight me.”
“Whomp whomp,” she said through his hand. (I won't), he interpreted.
Jack kneeled on the rope just below her wrist and reached to his back pocket, grabbed the ball gag, and put it over head. With his other knee he pinned her other arm, tightened the ball gag, and then grabbed both of her wrists. He pulled her half up, tucked her arms tightly to his chest, and wrapped one powerful arm around her, pulling her half out of the couch.
That was when she tried to make a move, but he was ready for it. He spun and threw her to the Lay-Z-Boy, and leaped onto her, straddling her, and grabbed the end of the rope. Then Jack took the end of the rope and fed it around the back of the chair. He pulled it tight dragging her secured wrist, and he grabbed the other one. She continued to try to struggle, but her efforts were in vain. He had her. Deep down she must know that, but she struggled anyway. People always did. That was the marvelous thing about human nature. You could be outgunned, outnumbered, and outwitted, but that didn't matter. A person just couldn't go without a fight.
Jack secured her other wrist with the rope and gathered himself.
“Now for the hard part little miss. Your legs won't be nearly as easy I don't think. I'll still manage it. Don't you worry about me. I will manage it just fine.”
Jack grabbed the longer rope from his back pocket, tied a similar loop, and slid that loop over his wrist. He leaned back and grabbed her foot, slid the loop over her ankle and tightened the loop. Then he fed that rope around the back of the chair grabbed her other ankle, and secured that one. He went around to the back of the chair, and stretched the rope downward, pulling her legs and arms back with the ropes and wedged them under the bottom lip of the chair. No way she was getting free now. He had her completely.
He walked back to the front of the chair and got his first really good look at his mark. She was well toned, and very athletic looking. Her legs were up in the air and spread wide. She was wearing a nightgown, but in her current, spread-eagle position, he could see the tan-lines on her muscled ass. Her white panties almost glowed in the dimly lit living room, and he could barely make out the shape of her pussy against the tight material.
“A swimmer,” he thought to himself. “I got me a swimmer.”
Jack reached down to the sheath that was attached to his belt, opened the flap, and pulled out his large knife.
“Your not gonna want to move a single inch now beautiful. If you do you'll end up bleeding, and I'm not gonna stop just because your cut. Do you understand?”
She hesitated, but only for a moment. A wet patch formed on her panties, and she slowly nodded her head yes.
“Good,” Jack said. “Very good.”
Jack got on his knees in front of the girl, pulled her panties away from her skin, slid the back of the knife against her skin so the blade was against the thin material, and cut. With a yank he tore the panties off of her, and he reached back down for her nighty. Jack made a slit on that and tore it from her body.
Jack stood and admired her again. She laid there in front of him totally exposed now. Her body was well toned from head to toe. A result from all of the swimming no doubt. Her breasts were not large, but well shaped and firm. Her small brownish nipples were erect. They were round and the points were well formed like the nipples on a baby bottle. He couldn't wait to get them into his mouth. He had to find out if they felt as good to his tongue as they did to his eyes.
He could see the fear in her hazel eyes. She didn't utter a sound. She just sat there wondering. Wondering what he was going to do. His orders were specific, and he would accomplish every task listed, none of them would harm her permanently, but they would, no doubt, change her forever. She didn't know that though. In her mind she could very well be breathing her last breaths, and he could see the fear of that in her eyes.
He had to admit to himself that the ball gag looked marvelous in her tiny mouth. He could see the spittle beginning to form around the edges of the ball. She was beginning to take deeper breaths now, her chest was locked with the fear that was coursing through her body, and sweat was starting to gather on her chest.
Jack knelt before her and smacked her ass.
“You ready to get started?”
“Whompf,” she said through the ball, shaking her head no.”
“NO?” He said questioningly.
He smacked her ass again a little harder.
“Don't ever tell me no,” he said firmly. “Now I'm gonna ask you again. You ready to get started?”
She paused for a second. She wanted to say no again. He could see that in her face, but she reluctantly shook her head yes. Her pussy started to glisten in the moonlight that drifted in from the unguarded window.
“That's a girl. I like that attitude much better. If you keep that up you might just make it through this.” It was an empty threat, but she didn't know that.
Jack took the flat side of the knife and smacked it against her pussy lips. She jerked and stiffened, taking a deep breath as she did so.
“You like that?”
“She shrugged her shoulders, but her eyes actually told him that she did.”
“What's that?” and he smacked her again.
“Wawhompf. Wawhomphin,” she said. (uh huh. I like it) he interpreted.
“Good.... Very good girl. Your learning quick.”
Jack bent down, and tasted her. She inhaled deeply again as he started to work her clit with his tongue. She was still hesitant at first. A big part of her probably wanted him to stop. To just go away and leave her alone, but there was another part. A part of her that she kept hidden from her family and friends that didn't want him to stop. That wanted him to keep going. To take her and have her, and want her, and even rape her.
After a minute she started to work her hips with the movement of his tongue. She could keep fighting it. To keep denying that the sensations she was having weren't good, but the truth was it did feel good. She was supposed to hate it, because he was an intruder in her home not her boyfriend or anything, but the truth was that it felt good. Boyfriend or not. It felt good. He worked her clit and her lips and moved to her open hole. She relaxed her muscles, in an invitation to keep going. She let out her first moan as he slid his tongue in and out of her opening.
He licked his finger, and started to work her asshole. She tried squeezing his finger out at first puckering it up, but after he worked it for a few seconds she relaxed and allowed him to enter her. He shoved his finger in, burying it and pulled it back out, working her pussy with his tongue at the same time. She let out another moan, and he slid his finger back in.
Her mind was in total conflict now. Half of it was begging her to make him stop. The other half begged her to beg for more. Which side would she give in to. That was the only question. Which side would win.
“Whompf,” she said. “whawhompf whompf whompf whompf.” (Yes. Do it just like that).
The latter side was winning.
Jack reached up and pinched a nipple. Alyssa took in another deep breath, and let out a guttural moan. Her hips bucked into his face. He pulled his tongue out of her and shoved it into her ass.
“Whompf whompf. Whompf whompf woe whompfin whoompf,” (Oh god that feels so fuckin good.”
Jack looked up at her and wondered. “What if I took it off of her. Would she scream?” If she did, he thought it might be with pleasure.
“You want this off of you,” he said. Pointing to the gag.
She thought about it, and then shook her head no.
“Wha whompf whim,” (I like it).
Damn that was actually kind of hot.
Jack smacked her pussy. She inhaled, and bucked her hips forward.
“If your daddy could only see you now,” he chuckled.
Jack went to the pile grabbed two of the items off of the list that he'd been given, and returned to Allyssa.
Her eyes got wide, but most of the fear was gone. She looked at the items, two dildos, one cone shaped to stretch a person out, and one large monster dildo. Larger than most men by far. As he presented them to her, whatever fear that was there before was replaced by animal lust. There was a tiger buried within this young girl, and the tiger was tired of being caged. Jack figured her dad must be a real tool. One of those guys that was so overprotective that he refused to let his girl live, even a little, and his girl was now so desperate for life, that even forced sexual activity sounded good to her.
Jack got back down onto his knees, set the toys on her flat stomach, and shoved a finger into her. She wasn't a virgin, not surprisingly, and started working her. He wanted to loosen her up a little before he started stretching her out. He was going to have to stretch her pretty good in order to get the massive tool into her, but he'd done his research. He watched eighteen-year-old girls about her size take dildos this size. If they could do it. So could she.
After a minute Jack grabbed the cone shaped dildo, lubed it up real good, and shoved the nose of it into her.
“Whompf whimpf,” she said. “Whompf Whe,” she said. (Oh god. Fuck me).
Jack did what she asked. He slid it in slowly and pulled it back out. She stretched to receive about two inches of the toy opening her up to about one and a half inches. Not to bad, but she had a lot further to go. He pushed back in this time making her take about two and a half inches, and stretching her to two.
“Whimpf,” she said. “whimpf woe whimpf,” (Shit. It's so big).
“What would your daddy think of his little girl now. Almost begging to be raped?”
“Whumpf why whampy,” She almost hissed. (Fuck my daddy).
“No. I'll pass. His daughter is way hotter.”
She must have needed the comic relief. She laughed heartily and Jack joined her. After they were both done he slid the toy back into her. She tried her best to relax, and the tool went in three inches. Jack fucked it in and out of her working it slowly deeper inside her daddy's little girl. The deeper the tool went the more the animal lust came back into her eyes. At the point where Jack didn't think she could take any more she had about half of the large tool inside of her. Her hips moved with each thrust, and she was stretched to about three and a half inches in diameter. It would still be a really tight fit, but Jack thought that might be enough.
“You ready for this one?” He asked. Pointing at the large toy.
She hesitated for a minute, but the adrenaline was pumping in her the same way that it was in him. She shook her head vigorously yes, with a look of determination in her eyes.
Jack grabbed the toy. It was heavy, about a foot long, and at least three and a half inches in diameter. Allyssa watched intently as he worked the head around her pussy. She bucked her hips trying to fuck it herself as it neared her vaginal hole.
“whump whip whin we. Wheeek. Whump whip whin me wow.” (Put it in me. Pleeeeaase. Put it in me.”
Jack worked the large head into her stretched pussy. God it was a tight fit. He took it out and lubed it up. Then he slid it around her pussy and pushed a little bit of the head in.
“Whump. Whump Whump,” She said. (Fuck fuck fuck).
With a little effort Jack got the head of it in.
“Uuuuggghh, wha. Whip in woooog.” (aaaahh.. it is good).
Jack slowly fucked her with the toy. Her eyes stared intently at the toy as more and more of it disappeared into her. The animal lust was full force mixed with her determination to fuck it. Young Allyssa had her first orgasm, come squirted out from around the tool, and she squealed into the gag.
Finally Jack couldn't take it anymore. He had to have her for himself. He reached up and removed the ball gag, straddled her, unzipping his pants as he went, and shoved himself into her mouth. He drove his eight inch dick all the way into her mouth, fucking it for a full minute vigorously. She didn't fight it. She took him in and allowed her mouth to be fucked. The excessive amount of spittle that had formed from the gag made it easy. He came quickly and she sucked his semen up as quickly as the ropes spewed.
Jack slid down and finally took a nipple into his mouth. The did feel as good to his tongue as they looked. Allyssa moaned as he entered her. Her young pussy had been stretched, but was already quickly recovering. She still felt tight around him, and her velvety tunnel was magnificent around his throbbing dick. He bent and kissed her deeply, and she kissed him back with as much passion.
Jack pulled his lips away from her and started pounding her a little harder.
“Is this what your daddy is trying to protect you from?” He asked.
“Yeah. My daddy don't want boys near me.” She answered.
“No?” Jack questioned. “Why's that?” He picked up the pace, and slammed into her, smashing his hips against her. “He don't want you to feel this good. Can't bear the thought of his little girl being fucked?”
“Huh, uh she moaned. My daddy is a fucking turd. Now shut up and fuck me harder.”
Jack did as he was told. He pounded into her with everything he had. The harder he pounded the more she moaned, and the more she moaned the harder he slammed into her.
Finally Allyssa squealed in delight as she had her second orgasm. Jack followed suit spewing his seed into her, and collapsed on top of his young mark.
They both panted their way into recovery. After ten minutes Jack got up and undid her bindings, and gathered everything up.
“Thank you,” Allyssa said. “You money is on my dresser in the music box.”
“Huh,” Jack said confused.
“I'm the one that hired you. You were worth every penny,” she said
“Wow,” was all Jack could manage.
“I can't afford to pay you again. It took me quite a while to save up, but you can come back anytime.”
“I think you should take that money and go shopping. This one's on the house,” Jack said with a wink.