Real Heartbreakers

My name is Jack and I'm a college student majoring in IT- and network security. I have always loved computers and I think that I knew from a young age that I wanted to work with IT. Computers were always my main focus and as I went through high schools I did get really skilled but also was left behind on most other things. Girls had always seemed like some strange unattainable creatures to me and I had hardly spoken to a girl when I moved off to college. Awkward as I was, I still did meet a girl during my freshman year but she dumped me only after a few weeks, stating that I was way too attached to my computers. I really didn't mind too much but this girl, Linda, did leave one big urge when she left. We had sex a few times and I couldn't seem to focus the way I had during high school anymore. My solution was online porn and masturbation and towards the end of my first year I was going at it daily, figuring it was keeping my grades up.

All the hard work had paid off though and I was leading my class by far and had also caught some attention from future employers. At the end of the year I had a few options for summer work, but one stood out among the rest. It was an IT security position at a very fashionable hotel in Palm Beach, which of course had several advantages. The job was to keep track of the IT security, which would be a perfect experience, but it also meant I would spend my summer in Palm Beach. I talked to the manager over the phone and accepted, and later that day I was packed and on my way.

Once on site I was guided through the hotel by my manager. It was enormous and very luxurious, and I was also asked to keep to the staff entrances as much as possible and to avoid bothering the guests. He then showed me to my office and I was handed a list of tasks to look after. I was a bit disappointed with what they referred to as top of the line equipment and I also felt the tasks I would perform were a bit basic. But I decided to just go with the flow the first days and assumed I would be handed more challenging work once I had proved myself. I was right, after only two weeks I was basically running the IT security. I had updated all their fire walls, erased a couple of security holes, and was now mostly monitoring the systems after fraud attempts. As part of an experiment I was running a program I had developed myself. I hadn't told anyone about my program since it was most likely not entirely legal, but if it did find some traces of fraud or unfair play I figured I could try to find evidence using the normal tools.

To my surprise I received an alert from the system only a couple of days after I had deployed it. There were two women, a Mrs Yevanova and her daughter, that had checked in during the morning and received special treatment due to an accident in the lobby. During the commotion the hotel manager had set them up in one of our luxury suites but had failed to find their alleged reservation. The manager had assumed this was a mistake on the staff's behalf and had ordered to offer the room to the women for the remainder of their two weeks stay. My system had noted that there were no log files of their reservation and no one in the staff had erased it either, so my system had determined it as an attempted fraud. Of course I couldn't go to the hotel manager with this without having to explain my system so I decided to do a bit more digging.

It didn't take me long to realize that their names were fake, there were no records of a Mrs Yevanova entering US soil, so she was either here illegally or using a fake identity. Either way, I was on to my first major security breach and was very excited. I did some more digging and later that night I found the missing pieces I was looking for. It seems the woman's real name was Max Conners and she had an outstanding warrant for avoiding taxes and was listed as a potential con artist by the FBI.

I stored all the information about her and her daughter in a secure folder and uploaded a backup to my personal online storage. I then sat back in my chair and started to wonder what to do. I was still not comfortable about reporting this to the manager since I had no real good explanation to why I would have suspected her in the first place. Of course, showing the IRS reports and the FBI files would at least be enough to have her arrested but at the same time I was a bit worried that a judge or defense lawyer might had wanted to ask me too many questions on how I had attained this information.

Another issue was that I had seen security photos of both Mrs Conners and her daughter Page, and they were both total babes. I started to remember some stories I had read online about guys bribing or blackmailing women into sleeping with them, and in most of them they had used less incriminating material than this. I was also really getting the urge to get in bed with a real woman again, and not only jerking off to online porn, so before I went home that night I decided to go and confront the women with my material in the morning and see how they would react. I assumed they would try to bribe or convince me to leave them alone, but if I suggested an exchange for sex I doubted they would accept. At the same time they would never try to get any authorities involved so I was not taking any great risks. I made up my mind in bed and then jerked off before I fell asleep.

The next morning I got to work early as usual and had my breakfast in front of my computer. This time though I had printed parts of my evidence and put it in a folder. Once I was done I checked the booking system and could see that they were still occupying the suite. I placed the folder under my arm and went out on my mission. Once in the elevator I was starting to get really nervous and I was almost shaking when I reached their door. I took a really deep breath and steadied myself before I reached out and knocked on the door. As I waited for a response, I ran through the plan in my head several times. Finally I could hear movement and then the lock and Mrs Conners opened the door.

"Yes?" she asked with a Russian accent and gave me an indifferent look.

"Mrs Yevanova," I said and nodded politely, "my name is Jack and I work with the security department here at the hotel. I was asked to come see you and get the details about the accident earlier and see if we will need to proceed with any legal matters."

"I have no need for that," she answered and was about to close the door. I had to react fast now I figured and before she closed the door I took a step closer and whispered to her.

"What if I call you Mrs Conners?"

She froze as she heard her name and stared at me with her big brown eyes seemingly contemplating what to do. She then slammed the door shut, right in my face, and I almost jumped back by surprise. I regained my focus though and decided I would at least get her to talk to me. I took a look around and made sure there were no one around and then went to knock on her door again. I assumed she wouldn't open so I spoke gently to the door.

"Mrs Conners, I know who you and your daughter are but I have not contacted the authorities yet. I was hoping we could come to some agreement that would be more beneficial for us both instead."

I then waited by the door and after a few seconds I could hear her unlock the door and open it. I went into her room and she quickly closed the door behind me and locked it. She then turned to me and it struck me that she looked really calm.

"So what did you have in mind?" She asked, with no trace of the Russian accent.

"And more importantly, what is it you think you know?"

"I think I know a lot about you Mrs Conners," I answered. "I know you don't pay your taxes and that the FBI is taking an interest in the whereabouts of yourself and your daughter," I continued and walked further into the room. Mrs Conners remained by the door, probably ready to run if needed, and I was now sort of assuming she would. She was wearing a very classy white, knee high, dress and white high heel shoes that I suppose would slow her down a bit. I was still not going to run after her so instead I focused on admiring her figures. She had long slim legs that ended in perfect round hips. I wish she would turn so I could how see how her dress hugged her tight round ass. Her dress also showed just a bit of cleavage, precisely enough to get a guy interested, and I had to force myself not to stare. From her neat looks, perfect make up with dark red lipstick, she was obviously just prepared to go out somewhere.

"I need more than that you little shit if you think I'm going to pay you," she said after a while, "you don't have any proof."

"But I do have proof," I answered and took the folder and held it out for her.

She hesitated but then walked up and took the file. She read a few pages and I could see on her reaction that she realized I was the real deal. She then shut the folder and threw it back to me.

"Ok, I see you have done your research. I suppose you will have to name your price. What will it cost me to keep you silent?" She still seemed very calm but I thought I heard a hint of nerves in her voice.

"Well," I answered, "I've been thinking about that, and considering the jail time you would get for crimes like these, and also the potential damage it could do to any future plans you and your daughter have, I can only say the price will be substantial."

She let out a deep sigh but then continued. "If you have read the material you will understand that I don't have any money, at least not in the amount you're talking about here. But I am working on something here that could possibly give me what we both want. The smart thing would be to just let me finish this before we talk again."

I was considering this and she did make sense. I had assumed she was here to run another scam and if she could rip off one of the clueless millionaires around here she could make us both rich. But on the other hand, my parents were already pretty wealthy and I was also looking forward to putting some of my software on the market one day, which would generate a fair amount. No, I had the chance at something more special here and I was going for it.

"I never said I wanted your money," I said silently after a while. I then quite bluntly let my eyes wander up and down her body. She must have noticed this because she quickly put a hand to cover her cleavage and looked disgusted.

"No way," she screamed, "get the hell out of my room you creep! If you call the police I'll say you tried to assault me." She stepped back from the door and just stared at me.

"Fine," I said and got up and moved for the door, "I hope Page is smarter." This was a dirty trick, but it seemed to work just as I had hoped, because she jumped right in front of me.

"You leave my daughter out of this, you hear me," she said, and pointed a finger at my face.

"Well if you won't pay me what I want it's only fair she gets a chance to instead. I don't want to call the cops on either of you, but one of you better give me what I want."

Mrs Conners just stared at me now and after a long silent moment she sighed and folded her arms again. "What exactly are you asking of me, in that case?" She sounded calm again but I could tell she was worried.

"What I want, Mrs Conners, is for you to pay me with sex," I said, with a surprisingly steady voice.

She stood quiet again for a long moment before she turned and walked for the door. I was disappointed at first, but she was just making sure the door was locked. She then turned back and looked at me.

"I don't want to hear a word about this," she said, "we do this once and then you're gone. You'll leave me and my daughter alone."

"That's fine," I said. "But as long as you're staying at my hotel you will just have to make sure I'm happy."

"No way," she said and backed off again, "one time, and one time only."

"Then I'm afraid I will have to decline Mrs," I said, desperately hoping she'd fall for my bluff. As I reached for the door knob she latched out again and grabbed my hand.

"Wait," she said, "I can't have you ruin my work here, but maybe we can find a compromise?"

"I won't be in your way Mrs," I said and let go of the door, "but you will let me in here when I want and give me the sex I want." I could see her hesitate and guessed she was trying to come up with her next idea but I decided to cut her off instead.

"That's my final offer," I said, "as long as you're staying here our deal is on, and I will make sure that your little business plan won't be ruined, and Page won't have to know anything either." Her expression changed now to one of almost hopelessness, but she finally nodded her head.

"I suppose I don't have a choice," she said finally, "should we go into the bedroom?"

I couldn't believe this was happening. She was really going to do it. I hadn't even considered where or how until now, but this was not the time to start hesitating.

"I thought we could start here," I said and pointed at the sofa, "come sit and let me get a better look at you." She didn't respond at first but as I sat down and gestured to the seat next to me she finally walked over and sat down too. She leaned backwards a bit which made her dress run a fair bit up her lovely legs. She instantly crossed her legs as she leaned back, looking extremely sexy and classy. I took a hand and slowly placed it on her knee. She didn't move so I decided to proceed and ran my hands down the side of her leg. She kept her gaze on my hand as I continued to caress her lovely leg all the way from her ankle and up to where her dress started. Once I reached her knee again I tried to press my hand in between her legs but she kept them shut tight.

"Will you spread you legs for me please," I said, realizing just how stupid that sounded. She did adjust herself in the couch though and slowly uncrossed her magnificent legs. As she moved, her dress moved up even further too and when she opened her legs I got a perfect view of her white lacey panties. I felt blood rush to me head and I must have blushed as I stared down her spread legs. My hand now moved down the inside of her leg, slowly, until I could finally feel the soft fabric of her panties with my finger tips. She twitched a bit as I ran a finger over her panties but remained still and let me move in close to get a better feel. My thumb and fingers were now slowly working her panties to the side and next I could feel her naked pussy lips. I had loved feeling my girlfriend Linda's pussy with my hand, but she was definitely not as hot as Mrs Conners, and she never shaved it like Mrs Conners had either. She was so smooth and as I kept fingering her I could feel her getting more moist making my fingers slide smoothly against her slit.

I was almost amazed with myself, how I managed to keep myself from just ripping my pants off and fuck her. Instead I took my time to really feel her up. My fingers grew bolder and once I found her hole I gently pressed in a finger and Mrs Conner again moved her hips a bit and spread her legs further. This made my finger slide in easier and she let out a soft sigh. I kept working my fingers deep into her for a good while until I could feel she was all smooth and wet. Now I just couldn't wait any longer, I had to fuck her. I let my finger slide out and then ran my hand all the way up to her knee again, leaving a wet trail of juices along her leg.

"Let's see if we can take this a bit further," I said and leaned back in the couch to get a better look at her. Her cheeks were a little flushed and she pursed her red lips in a serious but relaxed expression. As I was trying to figure out what to do next she closed her spread legs and took a deep breath, exhaling hard and fast. I figured she was waiting for me to make a move and this was when I realized I had more opportunities here than just fucking. I hadn't even considered it until now. My girlfriend Linda had never really given me a blowjob. She had kissed my cock once but then said she didn't like the taste, but here I had the opportunity of a life time. My eyes were glued to her red lips as I desperately imagined them wrapped around my cock.

"Why don't you unbuckle my pants Mrs Conners," I said and looked at her. She looked right back at me but didn't say a word. Instead she moved to sit up straight and then shuffled closer and reached out a hand and pulled at my belt. She then skillfully unbuttoned my jeans and I raised my butt and helped her to pull them down. Mrs Conners was about to move away again but I managed to slip an arm around her first.

"Come here and give me a kiss," I said and pulled her closer. She hesitated at first but then leaned in and our lips met. They were soft and warm and as the kiss went on she slowly parted her lips and seconds later we were having a full make out session. I held her tightly with one arm around her and the other hand was shamelessly exploring her body, running all over her legs and up to her chest to feel her soft breasts. Mrs Conners responded well to the kisses and sat there relaxed with both hands resting in her lap as we went on. I then found one of her hands and pulled it closer to me and placed it over my boxers. First she just held it there but as I moved my hips a bit she started to curl her fingers around my shaft through the boxers.

I was of course having a hard on already but the touch of her fingers made my cock grow even further and she must have felt how I stiffened in her grip. I could feel her work her hand in under the boxers and as she wrapped her hand around my cock and started jerking it I broke the kiss and let out a moan.

"Mhmm," I moaned and slowly moved my hand up her back until I reached her neck. There I let my fingers curl softly into her hair getting a good grip. Then I looked straight into her eyes and smiled and started to guide her head down towards my crotch. She started to pull back at first but as I held her with my hand she slowly let me guide her head down towards my crotch, and she gracefully slid down on the floor in front of me. I pulled down my boxers with my free hand as she shuffled in between my legs and my dick sprang loose and dangled just below her face.

I kept my grip on her head and curled her pretty hair as she lowered herself further and took my cock into her mouth. The feeling was just amazing as she slowly worked my entire head into her sucking mouth. The top of her head looked fantastic as it bobbed up and down and without removing my cock form her mouth she shifted to get up on her knees. There she could reach better and I felt how she slowly worked deeper on my cock with each stroke. The feeling made me jerk my hips and as she noticed this she pulled back a bit and only twirled her tongue around my head.

I let go of her hair and unbuttoned my shirt and Mrs Conners just kept sucking me slowly as I undressed. Never having experienced anything like this before I was getting nervous I would shoot my load any second now, and I wasn't ready to end this just yet so I placed a hand on her cheek and pulled back slowly and she let go of my dick and looked up at me again.

"You're amazing," I said, "but we should stop before I make a mess in your mouth," I continued.

"Well, what now then?" she said and sat up straight.

"Lets get you naked Mrs, " I answered and leaned back comfortably in the couch.

"Stand up and take off your dress for me so I can see you properly," I said, and gestured to the floor in front of me.

"We never agreed to a strip show," she answered as she slowly got up from the floor. There she stood still for a while and straightened her dress. Her lipstick was a bit smothered but otherwise she looked just as classy as she always did. She then reached around her back and unzipped her dress. She casually lifted it up her body and threw it to the sofa and then instantly went for her bra and also let that fall. Her breasts were not big, but perfectly shaped and sagged only a little. Her flat belly and slim hips really made her look much younger than her age. As I sat and admired her body she reached down to her panties too and pulled them down in one quick motion. She was now standing completely naked in front of my, her hands resting on her hips.