Breaking and Entering

Jack looked over his shoulder at a beautiful ass in tight jeans bounced by, probably one of the girls from the mail room. No way she was in the IT department looking like that.

His phone beeped, the alert from his alarm system at home. He swiped open the app, which allowed him to see the two webcams in his home, one in his office and the other watching the living room from above the front door. Nothing in the office, so he clicked the arrow to switch to the other camera and was shocked to see someone in his home. And not just anyone. Trisha from next door!

Trisha was the next door neighbor's daughter. She was 20 and in and out of jail and rehab because of a drug problem. Her poor mother bailed her out of everything and was constantly stressed out about the kid. Trisha was thin and cute, which also helped her get through life without working. Her boyfriends gave her all the meth she wanted.

He stood up immediately and walked toward the door. On the way he saw James, his partner in maintaining the server bank.

"James!" he called "Got a thing I need to deal with right away, I'll be back as soon as I can."

"No problem buddy, I got this."

Jack was already dialing his phone. He had Trisha's number from when he fixed her laptop last year. She needed it for a failed attempt at going back to school that had only lasted a month before she ended up in rehab again. She answered on the first ring.

"Jack?"

"Stay there Trisha." he said. It wasn't a request, it was a command. "I have you on video, all saved to my servers online. I'm also watching you right now. If you leave, I'm calling the police and handing over the video."

"Jack," she said. "I thought I saw someone inside, I... I just came over to check it out."

"You're a bad liar kid," he said. "I watched you put the $30 in your pocket that was laying on the kitchen table. And that's on video too. Just stay there and we'll talk about it. I'll be home in less than ten minutes. Maybe the cops don't need to be involved. But if you leave, or call anyone, I'm calling the cops. And I will hand over the video and press charges."

"Jack," she said, her voice rising, almost pleading, "I just needed cash to get something to eat. I'm sorry. I'll put the money back. I can't get in trouble again."

He got out of the elevator and headed for his car, walking quickly. He knew it usually took six minutes to get home once he was in his car. Today it would only take four minutes because he was in a hurry to get there before she decided to run with the cash and go get a fix. This opportunity was too good to miss.

"Just stay there, sit on the couch, and stay off your phone," he ordered, "and we'll figure this out." Then he hung up, started his car, and headed home in a hurry with his phone on his knee showing the camera in the living room. She was doing as instructed for now, sitting on the couch looking nervous.

She was still sitting there when he walked in the door. The $30 in cash was sitting on the coffee table in front of her. She looked great. Tired maybe, and certainly stressed out. No makeup, just a t-shirt and jeans, but she was cute.

"I'm sorry Jack..." she started, but he cut her off.

"Shut up and listen to me," he said. "Your mom tells me whenever you get in trouble. We talk a lot. I know you're on probation, and I know your last bust was for breaking and entering. I know you have a couple drug charges too, and you have walked out of court ordered rehab twice. They aren't going to let you just go to rehab this time. They will lock you up for this if I turn you in, and I have you cold on camera breaking in and stealing money."

"Please Jack," she tried again, but again he cut her off.

"Don't talk, just listen, he said. "You have two options. You do everything I tell you to do, or you go to jail tonight and you stay there a long time."

She looked shocked. Tears welled up in her eyes, but he thought they were mostly fake. She was probably used to faking it to get what she wanted. A pretty face and a few tears will get a girl a long way in this world with most people. But not Jack. Not in this case.

"We are going to take some pictures, he said. "No one will see them unless I catch you in my house again. Any argument from you, and you go to jail tonight. Do you understand?"

"Yes." she said, looking nervous.

"Good. Take your clothes off."

She looked hesitant for a moment, but then stood and began to remove her clothes. As he suspected, the thought of a photo shoot wasn't so scary. She would happily let him take a few nude pictures of her to get out of this. She knew she could be in serious trouble if she didn't do it, and what could it hurt?

While she was undressing, Jack walked into the bedroom, shook the comforter out so that it was smooth on the bed, and turned on a lamp. The appearance of soft lighting would make her more comfortable. Then he opened up the closet and pulled out a leather bag. It made a metallic clunk as he dropped it on the bed.

When he walked out into the living room she was in her bra and underwear. They were baby blue, a matched set. Her perky little tits, probably B cups, didn't require much bra. Her body was tight and her skin was smooth. This was going to be fun.

"I said take your clothes off," he said. "I didn't tell you to keep your bra and underwear on."

She sheepishly took off the bra, setting it next to her shirt and jeans on the couch. He watched as she took the underwear off, revealing a perfectly smooth pussy. Between the fresh shave and the matching underwear and bra, she must have been going to see her boyfriend tonight. Lucky for Jack. She was perfectly prepped for him.

"In the bedroom." he said, pointing down the hall. He followed her, watching her ass bounce as she walked down the hall. He stopped in the hallway, opened the door to a closet, and grabbed a digital camera before walking into the bedroom. She stood at the foot of the bed, her arms crossed to cover her nipples.

He took a photo right away, liking how vulnerable she looked. It helped to sell the illusion that he was just going to take pictures. She stood motionless, a sour look on her face. He walked over to the leather bag laying on the edge of the bed. As he got near her she took a step back, avoiding letting him into her personal space. He rummaged around in the bag and came out with a black leather collar with a large silver ring attached to the front and a sturdy buckle.

"Come here," he said, and she slowly took two steps toward him. He closed the distance with one step of his own and she stood frozen as he walked around behind her. He slipped the collar in front of her eyes and down to her neck, threading the end through the buckle in back. "This will look great on you."

Jack walked to the other side of the room, picked the camera up off the dresser and took another picture. Better to keep the illusion going as long as he could so that she didn't get spooked. He took a few more shots, ordering her to drop her hands so that he could see her tits in the pictures. Then he walked back over to the bag.

"Bend over the bed," he said, "This is going to be a great shot. A fun little bondage photo shoot. I'll even send you copies for your boyfriend if you want"

She turned and bent over partially, arms extended, her hands on the bed. He pulled out a pair of handcuffs from the bag and her eyes got wide. She looked scared now. Giving up complete control wasn't what she was expecting. She thought a few naked pics would be the end of it.

"Jack..." she said, but he cut her off yet again. She had to know that he was in charge.

"You want to go to jail tonight?" he asked. "Or you want to take some kinky pictures and leave? No one needs to know this ever happened."

She thought for a second, convincing herself that it was going to be fine. "OK," she said.

"Good. Now bend over all the way and put your arms behind your back."

She did as she was told, resigned to whatever was coming next, hoping it was just a few more pictures. He put the handcuffs on her, making sure they weren't too tight but just tight enough that she couldn't slip out of them. Her top half laid on the bed, while her feet were on the floor. Her ass rounded out nicely when she was bent over, and his cock grew semi-hard at the sight of it.

He took off his belt, and she started to lift her top half from the bed. He pushed hard on the center of her back, forcing her back down onto the bed.

"Stay down or I'll use this belt on your ass," he said. "That would look great in the pictures, some nice red stripes on that cute little butt. Don't tempt me."

She relaxed and laid still on the bed. He knelt down behind her and wrapped the belt through the bed frame and around her calves. Two trips around both her legs and the metal frame and he was able to buckle the belt, effectively tying her legs to the bed frame. Even if she stood up now, she couldn't go anywhere. Her legs were locked together and to the bed.

He took one more trip over to the bag and grabbed it. He walked over and stood behind her, setting the bag on the bed next to her. He pulled out a length of chain, maybe three feet, two carabiners, and a ball gag with a leather strap. She couldn't see what he was doing, but her body tensed when she heard the chain.

He put the ball gag on the bed next to her head, where she could clearly see it. Her eyes got wide.

"Jack, no" she said.

"Shut up and listen," he said, "You're not in a place where you can do much negotiating. I can put this on you if you can't shut up. Otherwise, I'll leave it where it is. Do you think you can be quiet, or should I put it on you now?"

She looked worried now, scared. "No," she said. "I don't want that thing."

"Ok, then keep your mouth shut and listen. If I have to put that on you I'm going to get rough." He grabbed the ends of the chain. He slung the center of the chain in front of her head, and pulled it toward him, forcing it under her face and down around her neck. Then he laid the ends down on her back, near her already cuffed hands. She stiffened, more nervous by the second.

He clipped a carabiner to the center chain of the handcuffs and then to one end of the larger chain. He ran the chain up her back and then pulled it under her face. She lifted up her head and it dropped down until it passed over her shoulders and across her neck. Then he ran it back down her back. He pulled her wrists up by the handcuff chain until they were high up on her back and clipped the other end of the chain to them.

She was completely immobilized now, her legs locked to the bed, her hands chained together and held up away from her ass by the chain around her neck. She could do nothing but pray that he just wanted to take pictures of her in this position. Then she felt his hand on her ass. He ran his hand over one ass cheek, then the other, before his hand moved up to the back of her neck.

"Obviously," he said. "I'm going to fuck you. If you are going to make noise or complain about it, I can put the ball gag on, or just choke you a little to make sure you understand who is in charge. Do I need to do one of those things, or can you just be quiet?"

She was silent for a moment, and then his hand moved onto her neck. She flinched. "No, I'll be quiet. Go ahead." And with that she checked out. Her body was nearly limp, just waiting for the inevitable. Just hoping he wasn't going to be too rough.

He took a bottle of lubricant out of the bag, squirted a little on his finger, and dropped his pants. His cock was rock hard now, seven inches long, thick, and straining upward. He put the lube on his cock and put the head at the entrance to her pussy.

"Good girl," he said. "Lay there and relax and you'll be fine. It's not like you haven't been fucked before." He pushed forward slightly, sliding the head inside her. He savored every moment, committing it to memory for later. It was a memory he knew he would refer to many times. She lay there still while he slowly slid into her, his hands on her lower back. He stopped halfway in, pulled out a little, and then slid in deeper. Slowly working his cock into her, savoring every moment.

She was so tight that even with the lube it was hard to get all the way inside her at first, but he had all the time in the world. She wasn't going anywhere. He kept working his way inside her until he was balls deep while she lay there, unable to resist. She was quiet and seemed resigned to her fate.

Then she tensed up and he saw a shiver run down her spine. "Don't cum inside me!" she said, "I'm not on the pill."

He continued to slowly thrust into her, feeling her cunt squeeze his cock when she spoke. She couldn't see the smile that blossomed on his face. "Don't worry hon, you can't get pregnant from where I'm going to cum."

This made her nervous. She had swallowed cum before, but didn't like it much. If that was what he meant, she could live with it. But she wasn't looking forward to it. She hoped that was what he meant.

He fucked her slowly for a few minutes, smacking her ass and telling her how good that tight young pussy felt. He told her that she belonged to him, that she was just a hole for his pleasure and there was nothing she could do about it. And then he put some lube on his thumb and started playing with her asshole.

"Please no," she said, "I can't do that. I've tried, it doesn't work. You'll hurt me really bad. Please fuck my pussy. You can cum in mouth. I'll suck you so good. You can cum on my face and take pictures if you want. I'll smile like I love it."

"Relax." he said, "If you say another word before I'm done talking, I'll put the ball gag on and pound your asshole deep and hard right now. Trust me, you don't want that. Nod your head if you think you can be quiet and listen."

She nodded her head, terrified. But something was also turning her on. She liked rough sex, had always liked it. A messed up childhood was to blame for that she supposed. Or to thank for it. And there was a big cock inside her and had been for a while. It made sense that she should be at least a little turned on. She closed her eyes and locked on to his words, which was exactly what he wanted.

"Now," he said. "I'm going to slowly work one finger in your ass while I fuck you. I'm going to use lots of lube and be gentle. And you're going to encourage me. You're going to tell me that you like it. And you're going to call me daddy. Nod if you understand."

She nodded again, her forehead rocking against the bed.

"Good. Eventually I'm going to get your ass relaxed enough that I can fuck it without hurting you too bad. But only if you are a good girl. If you aren't a good girl, I won't wait that long. Got it?"

She nodded.

"You may say 'Yes Daddy, I want it.' instead of nodding your head."

She gulped. She didn't think long. She didn't want to piss him off. She couldn't afford to piss him off.

"Yes Daddy," she said. "I want it"

"You want me to fuck your asshole?"

"Yes Daddy."

"Good girl. I'll be nice and gentle with your ass. I know it's going to be a stretch but you're going to be just fine. I'll give you a vibrator to keep you occupied when I put it in your ass."

He slowly worked his finger into her ass while he fucked her. He stopped occasionally to put more lube on her ass and on his finger. It wasn't terrible. She relaxed her body completely, knowing that it was her only option. She decided to make it as easy on herself as possible and just let it happen. She gave in.

He added another finger now, and more lube. He worked the second finger in even slower than the first, giving her time to adjust to it. After just a few minutes she was taking two fingers in her ass easily while he pounded her pussy. It was fine. She actually thought she could get off if he would let her play with herself. It wasn't great, but it wasn't bad either. Yet.

Once he had both fingers sliding in and out of her easily, he pulled his cock out and walked back over to the drawer. She tensed, worried about what might be next. Then she heard the hum of a vibrator turning on. She had forgotten about his earlier words. The vibrator while he fucked her ass. Probably a good idea. It would be a welcome distraction.

He slid it under her, between her pussy and the bed, and she could immediately feel it working it's magic. Whether she wanted to be turned on or not, a vibrator right on her clit wasn't going to give her much choice. It throbbed against her clit and she actually squirmed a little to get it in just the right spot.

"You like that huh?" he said.

"Yes Daddy." she replied, knowing those were probably the only safe words she could speak right now.

"Good," he said. "Keep it right on your clit and keep some pressure on it. You'll like this a lot more if you are turned on while I'm doing it."

With that, he put the head of his cock against her asshole. She tried not to tense up or pull away. His cock started to put more pressure on her asshole and she could feel it start to open up for him.

"Now just relax," he said. "Getting the head in is the toughest part. Once we get that done we'll stop for a minute and just leave it there until you relax more and let me in. You want this cock in your ass don't you?"

"Yes Daddy," was all she could say. He probably wanted her to talk about how badly she wanted it, but she couldn't bring herself to ask for more right now. She just couldn't.

"Good girl," he said, and the pressure increased. She could feel it pushing her open and knew that he would have the head inside her any second. Then it happened. He pushed a little harder and the head slid in.

She gasped as the head filled up her ass, stretching it wide open. It seemed impossible that she would be able to handle this. It was so big even when there was only an inch of it inside her. She concentrated on breathing and on the vibrator on her clit. The cock in her ass didn't move, and she relaxed.

He started to slowly apply pressure in and out as she got used to having him inside her. His cock was barely moving, just fractions of an inch in and out, but slightly deeper each time. And the vibrator was having it's effect. Her pussy was hot.

She could cum right now if she wasn't so scared of what was about to happen. She couldn't imagine taking his whole cock in her ass. It was too big. She was too small.

His cock slowly worked into her ass. It took ten minutes to get it all in. Each fraction of an inch felt like she could take no more, but then she would relax and he went a little deeper. When he was all the way inside her, he stopped moving for a minute.

"See, you took it all with no problem." he said, "We'll give you a minute to get used to it before I fuck you."

"Thank you Daddy." she said, but she wasn't thankful. It didn't hurt that bad. It was okay. But nothing to be grateful for to this bastard who was taking advantage of the plight she was in. Then again, she did break into his house. And she knew it was wrong. She even felt bad about it when she decided to do it. He was a nice guy, a good neighbor. At least she had thought so. But she needed to get high. And that need was more important than anything else.

Still, she understood why he was angry. And she felt like it was right for her to be punished. In fact, she would have done something self-destructive later to punish herself. She always did. She fucked up, and then she punished herself in some stupid way, and then she went and did it again.

As these thoughts took form, he started to fuck her very slowly. It was not painful exactly. A bit uncomfortable, and humiliating, but not agonizing. She had expected white hot pain, but this definitely wasn't that. And the vibrator hummed away, helping her through it. She could handle this. As long as he wasn't too rough, she could definitely handle this. And it would be a fair penance for her fuck up.