Annie knew that Will was not a very nice guy but he always treated her good. He would disappear for weeks at a time without a call and show up with lots of money in hand. He never tried explaining how he got it. She had her sneaking suspicion that whatever he was doing wasn’t legal by any stretch.

Then one day while cleaning her apartment she picked up a jacket Will had left lying around. It felt heavy and she ran her hands through the pockets finding a small pistol in one of them. She had no idea what kind of gun it was but carefully placed it back in the pocket and hung the jacket in the closest. The whole time she cleaned, she kept glancing at the closest door. She couldn’t help but wonder what he was doing with a gun.

Will came back later that afternoon and was looking for his jacket. He finally asked Annie where it was.

“Annie, where is my jacket?”

“It’s in the closet where you should’ve hung it lazy bones,” she said with a smirk.

Will walked over to the closet and opened it. He reached in and Annie saw him run his hand into the pocket the had the gun in it. He pulled it back out and seemed satisfied it was still there. He closed the closet door and turned back towards her without saying anything.

Annie had continued work on cleaning up the small kitchen like she had been doing when he came in.

“If you are about done cleaning, let’s go out for dinner.”

Annie knew he must have still have been holding a lot of cash. He was always taking her places when he first came home but in a few weeks’ time things would slow down. Then one day he would disappear again.

It was those few weeks he had the cash that kept her from asking too many questions about what he did to get it. She loved him and he treated her like a queen. He always left her money while he was gone.

The Hotel

Will had been gone two weeks again and Annie had never heard a word from him the whole time. When he showed up one morning, he told her they were going to go away for a few days to New York. He had made all the plans before ever coming home. So, she packed and they left for New York.

Will never seemed to drive the same car each time he was home and this time he had a newer Ford Explorer. She never asked about that either. They were always newer and nicer cars.

They sped up the highway from Baltimore to New York City. Having left as soon as she packed, they got into the city early in the afternoon. He went straight to the Mandarin Oriental hotel. She was shocked when he pulled up in front of it.

Looking over at him with that shocked look and asked, “This is where we are staying?”

“Yes babe, the boss is paying the bill as a treat for a job well done. We have three days with everything paid.”

What Will didn’t tell her was he was still working too.

As soon as they opened their doors a valet was there to take the keys to the Explorer and bellhop was there to get their luggage. They followed the bellhop into the building. He stood off to the side with his cart as Will walked up to the desk to check-in. This for milady was handled quickly and they were on their way up to their room following the bellhop again.

Getting to their room door the bellhop opened it for them and said, “Welcome to one of the Hudson River rooms. So, named because they overlook the Hudson River,” he explained.

Annie walked over to the floor to ceiling windows and just gaped at the view outside. Will walked up behind her and wrapped his arms around her saying, “What do you think?”

“I’m speechless that anybody can afford this place. Your boss must be paying a fortune for it.”

“He can afford it, trust me.”

That’s all she could do was trust him.

The Stay

After settling into their room, they went out for a fabulous dinner in one of the restaurants that occupied the ground floor of the Mandarin. Then took an after-dinner walk enjoying the nice weather before heading back to their room.

What Will didn’t tell Annie was he had a destination in mind. There was a jewelry store just a few blocks his boss wanted him to check out, hence the paid vacation to New York. Annie had no clue.

When they got back to their room Annie said, “I’m going to go dive into the tub. It’s bigger than my whole bathroom at home.”

Will laughed and said, “Enjoy your swim babe.”

While Annie was in the tub, Will sat down and made quick notes of what he saw of the jewelry store during their walk. When done, he slipped the pad into one of the lower desk drawers, thinking Annie would never open it.

Finally, Annie reappeared from her swim in the tub wearing a large white cotton robe.

“If you didn’t drain the hotel’s hot water heater I’m going to run through the shower,” Will said, laughing on his way to the bathroom. As he shut the door, he thought he heard a fuck you come from Annie.

Annie decided Will deserved a treat and dropped her robe on the ground before climbing onto the bed. The maid service had turned the bed down while they were gone so it was ready for her. She was able to just climb right onto the silken white sheets. The brightness of the sheets made her soft coffee-colored skin standout, perfectly framing her for Will. She propped a couple of the pillows up behind her and fanned her long brown hair out over them. Now she just had to wait for her man.

It wasn’t long before Will walked into the room carrying a towel in one hand and nothing on. She looked over at him, taking in his maleness from head to toe. He was a well-built guy, standing about six-foot-tall, short blond hair, a chiseled face that went well with his chiseled torso. Then she let her eyes roam further taking in his cock. Even soft he was about six inches long and thick. She knew from experience; fully hard he was just over seven inches long and a good three inches thick. She paused looking him over until she worked her way the rest of the way down his body.

She had noticed many times before he carried several scares that looked like knife wounds and bullet holes that had healed. Tonight, was no different other than he had what looked like a freshly healed place on his thigh. She knew better than ask about it because he always played it off to her.

Annie wasn’t the only one to be taking in the sights. Will’s eyes were roaming her body as well. She laid there resting against the pillows and he thought as he always did, she was the sexiest woman alive. Her hair fanned out around her, framing that soft angel of a face. His eyes wandered lower looking at her strong shoulder before ending up on her breasts. He knew she wasn’t the most endowed woman but her 36C breasts were perfect for her body. Continuing down her body, he could see her taught tummy and with her legs only partly spread, he could see the top of the tuff of hair she kept trimmed above her pussy. The way she was laying he couldn’t see her pussy but that didn’t matter to him, he already knew it quite well. Those thin lips that became very puffy when she was aroused. Her slender clit that would poke out begging to be sucked from them. The soft tunnel of her sex, yes, he knew it well. He finished the tour of her body, running his eyes along her muscled legs from running before returning to see her gazing at him.

She patted the bed next to her and that was all the invitation he needed. Dropping the towel to the floor and slid onto the bed next to her. As if drawn by a magnetic force their lips came together. Her lips parted allowing him to slip his tongue in to dance with hers. Before long they were cuddle close, exchanging long loving kisses.

Eventually, their hands started to roam upon each other’s bodies. He worked his hand to her mound, rubbing and teasing her before slipping a finger into her. She slid her hand around his cock, letting her thumb run over the soft head. They each continued their stimulation of each other until finally, she pulled him to her, spreading her legs for him to have easy access.

He obliged her and moved over top of her, settling between her legs. She raised her hips to him and he lowered himself to her. He slowly entered her and pushed deep. There was no frantic fucking, just slow love between them. He would pull most of the way from her before slipping deep again. She would raise herself against him each time he moved forward, pulling him as deep as she could.

Neither in a hurry to have this end. They carried on sharing their slow lovemaking until they were both on the verge of orgasm. Knowing it was coming to end, Will raised up grabbing Annie’s hips as he did. Now there was nothing slow or loving involved. He worked his cock hard and fast in and out of her pussy causing her to erupt in her first orgasm of the night.

He continued pounding her as she moaned and panted through her orgasm. Her pussy was like a hot glove on his cock. Knowing he wasn’t going to last much longer but wanting her to have another orgasm, he reached down and started running a finger across her clit. Annie was starting to thrash under him as he quickly applied even more pressure to her clit with each thrust, he made.

That was it, she started her second orgasm and this brought him over the edge as well. He pushed deep into her soft tunnel and unleashed a torrent of his cum as she bucked against him releasing her second orgasm. Their fluids mixed and ran from her to soak the sheets below them but they could’ve cared less. Intertwined they both fell fast asleep on the wonderful bed.

Time to leave

The morning of the third day Will had left to scout the jewelry store some more. He had left every morning under the guise of working out in the hotel’s gym but had really been out taking notes and watching the jewelry store. He’d tried to go every afternoon as well but actually spent most of the time with Annie instead. He knew the boss would be less then thrilled if he didn’t have all the info needed.

Annie had gotten up and taken one last luxurious bath before heading home. When done, she had straightened up and packed her bag while waiting for Will to come back.

She sat down at the desk to write a thank you note to the maid staff. They had been so good while they were there and never seemed to be in the room when they were. She appreciated the people with thankless jobs.

Looking first in the center drawer she found a pen but no paper. She started at the top drawer and worked her way down through each drawer looking for a pad of paper. She knew there should be one. It had been on the desk the first night. Finally opening the very bottom drawer, she found it but it had been written all over.

Pulling it out, she started reading it and realized it was in Will’s handwriting. As she read, it hit her that these where notes about the jewelry store, they had visited their second day there. The notes were very detailed, describing camera positions, where the security guard stood, what type of doors and a very detailed list of what was in the cases. Further on, there were times written down when the workers showed up and how late anybody stayed.

As she read, it dawned on to her that the times written for the workers mirrored when Will left to workout each morning and evening. Suddenly it her like a ton of bricks, he had been casing the jewelry store for somebody. She could only awesome for his boss.

She sat there holding the pad just staring, realizing her suspicions about what Will did to earn his money was right. She was still holding onto the pad when she heard the lock on the door click. She quickly shoved the pad back into the drawer and moved over to the bed where her bag was open just as Will stepped through the door.

Turning to look at him she asked, “How was your workout?”

“It was great. I see you have already packed up. I’ll take a shower and we can get on the road home.”

“Oh, before you take a shower, do you know where the pad of paper is. I wanted to leave a thank you note to the maid staff.”

“I think I saw it on the desk, let me look.”

Will went over to the desk and started opening drawers. He made a show of looking for the pad until he thought Annie looked away. He quickly grabbed the pad and tore his sheet of notes off and tossed the pad on the desk saying, “Here you go. It was just stuffed in a bottom drawer.”

He quickly crumpled the page of notes up in his fist and said, “I’m going to shower.”

Annie had seen the whole thing looking into the mirror over the desk. She loved him but decided never to confront him about his chosen profession. She was content to be around there for him each time he came home.

Returning Home

Most of the way home they were both silent keeping their inner thoughts to themselves.

Annie was coming to grips that Will was a thief of some kind. She had known for a long time he was probably a bad guy but now she knew for sure. That realization scared her but excited her at the same time. She had dated the plain jane guy and never felt the excitement she felt with Will. It was scary to her but the thrill was even better.

Will was concentrating more on the job coming up. He kept playing the details in his head. As much as he cared for Annie, the job was their future. This one last heist to set them up for life. He was ready for that with Annie.

They had just hit the outskirts of Baltimore when Annie looks over at Will and says, “Two cents for your thoughts?”

Will didn’t bat an eye with his reply, “I’m thinking of ravaging you when we get home.”

Caught a bit off guard she replied, “Oh, really?”

“Yep!”

They got the rest of the way home and no sooner had Annie sat her bag down Will grabbed her.

“I told you I was going to ravage you when got here,” pulling her towards the couch. He pushed her over the back of the couch so she was bent over it with her head down. He grabbed the hem of the short skirt she was wearing and flipped it out the way leaving her bent over in just a little blue thong.

Will knelt down behind her and grab her hips in his hands to hold her and started kissing and nipping at her ass cheeks. This set Annie to squealing and telling him to quit but Will had other ideas. With her bent over he had perfect access to her pussy and ass. He ran his tongue across the fabric of her thing covering her pussy and traced it all the way up between her ass cheek. Annie went from squealing to a soft moan partway through.

Still holding her firmly with one hand on her hip, he used the other to pull her thong from her, not bothering with trying to remove it. He simply pulled the thin piece tracing through the valley of her ass until it tore away from the waistband.

Annie yelped and shouted. “You tore my thong!”

“It was in the way,” Will replied just as he pressed his tongue against her asshole. He knew how much she loved having her ass played with. She was one of the few women he had ever met that preferred rough anal sex. He was always willing to accommodate her.

Annie moaned at the touch of his tongue on her opening. She felt him lick all around it before pushing the tip of his tongue into the opening. She was always so tight he could never get more than the tip in the outer edge. She gripped the front edge of the couch as he continued teasing her with his tongue but she knew what was coming next. What she didn’t know he intended to play a bit longer.

After thoroughly wetting her asshole down, he traced his tongue along her valley until he was licking her pussy. He traced his tongue over her lips that had already started becoming moist with her own excitement. He pushed his tongue between her lips as he ran his hand over her clit before settling on it with two fingers. He stroked her clit as he fucked her with his tongue. Annie was now loudly moaning almost uncontrollably.

Will taking his hand off her hip he wetted a finger with her own juices by running it over her pussy. He then pushed it into her ass firmly, sinking it as far as he could. Annie squealed at the intrusion before settling back to moaning.

Will began to stroke his finger in and out of her ass all the while continuing to tongue her pussy and tease her clit with his other hand. He could feel she was getting close to orgasming and that he didn’t want so he slowed down before completely stopping. Annie let out a frustrated moan as he pulled away and slipped even his finger from her ass. Yet she knew what would be coming next.

Will stood up and dropped his jeans to the floor leaving him standing there with his semi-hard cock ready for action. Slipping out of his shoes and stepping out of the pile of jeans he moved back over to Annie who was looking back over her shoulder at him. She knew and knew it would hurt and feel so good at the same time.

She felt a cool liquid run along the valley of her ass as Will used a finger to work it into her anus. He worked one finger and then a second into her opening, spreading her and lubing her for him. He continued working the lube into her anus until he was easily able to slip three fingers in and out. Annie was trying to relax as she moaned at his touch.

Then it was time, Will stepped up to her and placed the tip of his now hard cock at her opening. He leaned into her pushing gently but firmly until the head popped through causing Annie to yelp. He paused briefly before continuing, opening her up as his cock slid in. He felt the resistance of the inner ring and applied more pressure until it opened to him. After that, he was able to slip in as deep as he wanted.

Annie, knowing it would hurt, flinched and moaned as Will invaded her anus but she would never say stop. She loved the feel of his cock buried deep between her cheeks. He was her bad boy and she was his bad girl; it was only natural their favorite sex was considered bad by most people.

Will let her adjust for a minute until he started working his cock back and forth in short strokes that became longer as Annie loosen around him. Before long he was pulling almost all the way from her ass before driving his cock back in hard deep. Annie moaned and shock at his relentless pounding.

Will knowing he wouldn’t last forever wanted to give Annie her orgasm with his. He reached under her and slipped two fingers into her pussy and moved his thumb over her clit, stroking it back and forth. He could feel her approaching the orgasm he held off and started increasing his own pace in her ass. He was determined they’d cum at the same time.

For all his determination he missed it by mere seconds. Annie let out a scream and her body tensed as her orgasm hit with all the force it had. This caused her pussy and anus to contract as her body tighten. That was all that was needed for Will to start cumming deep in her ass. He pushed hard against and unloaded everything he had into her.

They both were moaning and hyperventilating in their orgasms. Then both just deflated, Annie still draped over the back of the couch and Will laying across her back. As they laid there like that, Will’s cock softened and slipped from Annie. She felt his cum start seeping from her and along her ass valley.

Finally, Annie said, “Will, let me up or there will be a mess to clean up.”

Will knew what she meant and let her up and she dashed to the bathroom. Next thing he heard was the shower start. Stopping just a heartbeat to think about it, he finished stripping and followed to the sounds of the shower.

Later that night Annie laid curled up in Will’s arms thinking. She knew he was a bad guy but she loved him and he did things that excited her no guy ever had. She could live with that, fuck everybody else.