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Jessica’s New Career

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I had gone into Max’s to have a quiet drink, it was Tuesday night normally a quiet night, and I just wanted to enjoy a glass of wine. I was tired is had been a hectic last year losing her entire family, parents and her brother. They had died in an automobile accident, nobody’s fault just one of those things. It was going to take some time to get used to being alone. She had decided today that she would start looking for a job tomorrow.

Dropping into Max’s for a glass of wine was one of the steps Jessica had taken to re-establish some sort of life for herself. It was quickly becoming a mistake.

“Hey, John is my name, can I buy you a drink?” Chimed in the third guy since she’d arrived twenty minutes ago. She was just about to let lose with a loud. Leave me alone. When she heard another voice behind her.

“Hey girl, sorry I was late, but you know your aunt always has something to say no matter how hard you try to get out.”

Jessica was puzzled as she turned around and saw an older gentleman, perhaps in his fifties and was about to say something, when she heard him speak to the latest pick up artist. Kevin was tall and slightly balding but there was no fat on him. He looked like he tried to stay in shape and for his age he was.

“Sorry buddy, I understand your attraction to my niece here, but she and I are going to have a drink and then dinner. So please just let us enjoy our evening.”

Jessica was still trying to figure out what was happening as the young guy hung his head and slipped away. Before she had a chance to say anything the man said.

“Name is Kevin! I saw you were a constant target for the lounge lizards and were getting a bit frustrated, so I decided to rescue you. Let me sit here while you enjoy your drink and my presence should help to keep the boys at bay. I am harmless, like you just here to enjoy a drink or two before heading home.”

Jessica looked stunned but he did look harmless, a lot like her father, there was a comfort in his eyes, she felt she could trust him. “If you don’t mind I would certainly appreciate not being hit on every 10 minutes!”

So they sat and enjoyed their drinks and Kevin eyed Jessica a bit more closely. She looked to be about 5’3″ tall, slim and what looked like a pretty good figure, though you could not tell. This was a woman who did her best to hide whatever attributes her body had to offer, though she obviously had fairly large breasts. Her long, waist length blonde hair, her green eyes, pouty lips and her slim attractive face gave away her obvious beauty.

They chatted for a while, Kevin buying Jessica a second glass of wine. She was feeling comfortable with him and told him of the tragedy that befell her, losing her entire family and that nights like tonight were her attempt to put some sort of life together.

When she had finished her wine Jessica thanked Kevin for his gallantry in rescuing her and got up to leave.

“Jessica, if you don’t mind I have to go too, and I would feel like a real schmuck if I did not escort you to your car”

With that they left and walked thru the parking lot towards Jessica’s car. Halfway Kevin stopped to sneeze and as he covered his face with one hand he released an aerosol spray into Jessica’s face. Before she could react the drug hit her and Kevin put his arm around her and steered her into his nearby car. By the time she was seat belted into the passenger seat she was out cold and would remain so for the next two hours.

When Jessica finally awoke she found herself chained to the wall and some sort of ball was imbedded in her mouth. Every time she tried to yell for help it came out garbled. Her legs and arms attached to the ringbolts in the wall, spreading her body into an X shape. She saw that she was dressed in a very tight pink corset that pushed her breasts together and up, a pink garter belt and fine light pink hose and a pair of six inch pink high heels. She was a bit groggy but otherwise fine. She was close to panic, she remembered leaving the bar with Kevin and then waking here. She thought about screaming but felt as thought no one would hear her. She jerked as she saw the door begin to open it was Kevin.

Jessica screamed at Kevin but her words were muted by the ball-gag in her mouth.

“Jessica, Jessica, Jessica you do look lovely in that outfit, I never suspected your tits would be so big, and beautiful. You know that outfit covers your nipples a bit but last night as you were being dressed you would not believe how erect and tasty they were!”

Jessica was getting angrier and angrier and her words got louder and louder but other then the increased volume nothing was understandable and Kevin just shook his head and continued.

“Now Jessica, I have to tell you the truth. You are going to come to work for me and I need to make sure you are trained. So over the next month or so, my staff is going to train you in all the different sexual practices that my clients expect to enjoy when they purchase a girl form me.”

Jessica continued to scream thru the gag and shake her head no again and again. Her tits were bouncing as she struggled in her chains and still Kevin ignored her and continued

“Jessica, your fate is no longer in your hands. I hold all the cards. No one is out there to miss you, no family, and you have been shut in for the past eight months that no one will even suspect your gone. So, I have you and I will put you to work in my organization like it or not!”

Jessica looked at Kevin and saw a good deal of steel in those eyes as well as determination and evil.

“Yes, I train girls and women to provide sexual satisfaction to my clients. You could use the term “call girl” or “hooker”, but I don’t care how you refer to yourself, you actually will have only one choice in this! You have the choice to accept and embrace your training and be the best fuck you can be, or muddle through training and be a street whore. To some degree the choice is yours, though your own ability to be a ‘good fuck’ will play a role.”

So street whore or call girl, wow, if only me friends cold see me now! Bastard, why do you think either of those disgusting positions would appeal to me? Jessica thought as she glared at Kevin. Her throat hurt and she realized the futility of her screams. She would wait for an opportunity.

“Jessica, don’t misunderstand me, I could give a shit where you end up you can be the best and fuck wealthy men in nice places or just be a so-so fuck and turn tricks for middle class men in cars or against buildings in the slums for nickels and dimes. Either way, the training will make you want sex, all kinds the only difference is the cleanliness of your trade.”

Jessica was trying to contemplate how she ended up in this predicament. She realized that no one would even miss her and that she was on her own. She was not ready to give up yet she would keep her eyes and ears open and look for a way out. But until then, she would have to put up with this training. She was immobile throughout this discussion, and now she just allowed her mind to collapse into her and tune everything out. She did not know how long she was in this state, but at sometime she was awoken by sensations between her legs and on her breasts. She opened her eyes and saw three beautiful women, dressed as she was. Two of them had taken one of her breasts each and the third was using her tongue on her vagina. She could not believe this, she detested women in that way and she was ready to scream for help again when Kevin walked in.

“Jessica these women are beginning your training, and others like them will rotate in all day long sucking on your tits, biting and pinching your nipples and eating out your pussy. This will be constant and you will not be able to stop them. I imagine they will bring you to orgasm so many times your cunt and tits will begin to ache not only from their ministrations but also from the reactions of the multiple orgasms. You will need to embrace this and learn how easily you can get off. I will stop in frequently to monitor your progress, enjoy your self!”

With that Kevin left and Jessica was left with her thoughts and her anger. She resented not being able to get away and even though she detested the thought of having sex with women, evidently her body didn’t because she could feel herself heading towards orgasm. She decided to let herself go.

For the remainder, of the day Jessica was sexually stimulated by three women at all times. They would rotate as they were there switching from a tit to her cunt to another tit always sucking licking and biting. Jessica lost track after her first ten orgasms. At some time they released her from her chains and laid her flat on a steel table, refastening her arms and legs to the corners of the table and removing the ball-gag. Jessica had orgasmed so often she did not have the strength to scream or complain. The woman between her legs now got into a sixty-nine position and tried to get Jessica to eat her pussy. Jessica turned her head away and the woman took her hand and grabbed Jessica’s clit and pulled it hard and twisted it viciously.

“You will eat my pussy or I will continue to find ways to give you pain”

Jessica could not believe how painful the woman’s actions were and she immediately stuck her tongue into the woman’s pussy, tentatively licking it. After a few minutes, her own orgasms took control and she absent-mindedly began eating the woman’s pussy like it was the best meal in town. She spent the remainder of the day either begging them to stop or begging for more when the shift changed. Finally it all ended and Jessica was left alone. She felt her ravaged body relaxing and her mind was reeling trying to recall everything. She never noticed when she passed out. This was Jessica’s life for the next seven days. She was stimulated and forced to stimulate others all day, stopping only for meals. She did not know why, but she was not allowed to shower.

She awoke on next morning of her eighth day, was forced into a shower and then she was forced to her knees. Her arms were secured behind her back, her thighs were strapped together with a wide leather belt and there was another leather strap around her chest, pinning her breasts and secured to the opposite walls, effectively locking her in place. There was no one arousing her and she felt a bit lonely after the past week. She was also stark naked today, nothing to cover her tits or pussy. It wasn’t long though before the door opened and Kevin walked in.

“So Jessica, how are you today? And how was your week?”

“You asshole, you know what I went through this past week, do you really think there is any way I enjoyed that?”

Kevin turned on the TV and pressed a button, immediately Jessica appeared on the screen. She was writhing on the bed begging the women to lick her harder, to pull her nipples and to find something to put in her so she could cum. Kevin hit the pause button.

“So…?” Asked Kevin.

“So what you old fuck, my body betrayed me, that’s all”

“No Jessica, your body did what your mind wanted. Only you refused to accept it. No matter you will soon. Now today will be a bit different.”

Saying that in walked a young man, naked. His cock was average length soft, about 3-5 inches. He stood waiting for Kevin to give him the ok to act.

“Jessica, this next week or so you will learn to suck cock! You will learn how to make a man cum when you want him to and you will learn to take him into your throat.”

“I don’t do that, I hate putting that thing in my mouth”

“First of all that thing is a cock, say cock for me Jessica!”

“Fuck you, no”

Kevin grabbed an object form the closet and stepped behind Jessica. Before she knew what hit her, her ass stung with pain and she screamed. Again and again her ass was attacked and again and again she screamed. Somehow she figured if she screamed out cock, perhaps he would stop, so she did.

“See how easy that was Jessica? Now remember you are to do what you are told or we will repeat that exercise. You should know that I hate doing that because if fatigues me, and it might maim you, my product. So be careful, I may have other more painful ways to punish you. Now suck his cock.”

“OK Jessica, you have three minutes to get him to cum. If by that time he has not cum, he will begin to fuck your face. I don’t want you to think I told him to go easy either, so suck him and do it well. You will be sent twenty men a day until you learn how to suck a man, and control his ejaculation. As one of my “girls” it is important that you be able to have my clients cum when it is best for both of us. So as you learn to make these men cum in the three-minute time frame you will also see how to make the man cum and therefore control his ejaculation.”

At that the young man put his cock against Jessica’s lips and forced his way into her mouth as her jaws opened slowly to admit him. Her faced was all scrunched up, obviously almost sickened by this object in her mouth and she had a hard time convincing her self to suck him. She figured letting him fuck her face was the better choice. Boy was she wrong.

At the three-minute mark, the young man grabbed the back of Jessica’s head while the leather straps held her in place. He pulled his cock almost out and then rammed it in, the tip of his cock bouncing against the back of her throat, causing her to gag, he removed his cock for a second to allow her to relax.

“Uuuuuuuuuucck” was the sound Jessica emitted and then she coughed and spit.

The young man re entered her mouth and resumed fucking her face with wild abandon, often reaching her gag reflex but not stopping, just kept pumping, Jessica body would convulse each time he caused her to gag, and she would make a retching sound around his cock with each gag. She could feel that her lips were bruising and she knew her jaws were aching and suddenly she felt his cock jerk in her mouth and his cum began to fill her mouth.

“uck!” Said Jessica as she began to spit the man’s cum from her mouth.

A hand cupped her mouth and forced it closed and said, “Swallow”

Jessica held out as long as she could but eventually she realized that the taste of the mans semen in her mouth was far worse then just swallowing the remainder of his load.

“Jessica you will have over twenty cocks today you will learn to make a man cum in three minutes or less or your face an lips with be bruised badly. The cocks will get longer and thicker each day, so with each failure to meet the three-minute mark, more and more cock is going to penetrate your throat. Also, since you seem to not like the taste of a man’s cum, if you can meet or beat the three minute mark the men will not cum in your throat. They will instead cum on your face or tits or wherever they choose. So let get back to work.”

Jessica failed to get any of the first twenty men on day one. So she was continually face and throat fucked and her belly was full of cum. Surprisingly, she saw this as a challenge and over night she began to try to figure out what she did to get the men to cum. If she could pinpoint the reasons they came, she could then meet the time goal. On day two she would do her best to notice what got the men excited and what did not. She knew this would be the way to get to the three-minute mark. For the first time since she had been forced into this she allowed her spirits to rise.

Her hopes dampened some when she saw first cock of day two. It was at least 6-7 inches soft and most of the cocks yesterday seemed to gain a couple of inches, as they got hard. If this guy fucked her face her throat would take a lot of cock and it frightened her. She just had to make it.

She failed and when the man forced all of his cock into her throat she felt as though his cock was reaching into her belly, then it was receding and coming again with force. Her throat was not hurting as much as she thought it might but what did surprise her was how wet her own vagina was getting as this man fucked her throat with his long hard cock. She came when he did and for the first time greedily swallowed his cum.

Having found that she enjoyed a cock in her throat Jessica abandoned her plans for the day and took all of the second days cocks rammed into her mouth and throat.

She recovered on the third day and she gradually got the hang of it and had most of the men cuming in under three minutes and as promised they sprayed her face, tits, hair and ass with their cum. Whenever she saw a larger cock though, she would intentionally lose the time race. She wanted to see how much cock she could swallow, and just how hard she could cum while doing it.

One of the cocks on what was to be her last day of cock sucking made her smile. As the man entered, his cock was an easy nine inches and fat while soft and she knew she would have at least ten inches of cock to try to swallow. Just the thought had her wet and ready. She intentionally failed to meet the three minutes and that dream cock rammed itself into her mouth and down her throat. She could not believe how deep it went and the feeling she had. She started to cum the first time he bottomed out in her throat and did not stop until long after she swallowed the all of the huge load he blasted into her mouth, not losing a drop.

When she had finished, although she did know it, Jessica had sucked over 160 cocks, swallowed close to eighty loads of cum and the remainder was sprayed on her body or in her hair, she was a mess. However, each night as she was released form her bonds fell into bed and passed out.

When she awoke the following day Kevin was they’re waiting for her.

“So, Jessica how are we today?”

“My throat is a bit sore and I could use a shower, but all in all not too bad.”

“Well you will shower this morning because we have finished your cock-sucking training and are starting the next phase. The training gets harder as we go, you must have guessed that our next step in your training will either be your ass or your pussy?

Jessica merely nodded, somewhat resigned in appearance, but on the inside she was looking forward to more sex. Everything they had done to her eventually made her cum. For her first two weeks here she had cum an average of fifteen to twenty times a day. She was beginning to realize she needed to cum.

“Ok. Today we will start grooming your ass. You are to lie here over this padded bench and put your ass in the air. That’s good, now the guys will have lube and will take it easy on you in the beginning.”

As Kevin left her there, the first man entered and Jessica was sure it was the guy she sucked first when she began her cock-sucking program, though she could be wrong there were so many men and so many cocks. As he lined his cock up behind her she felt the tip brush against her rear opening and she tensed. He instructed her to relax and he proceeded to push his lubed cock into her ass. It took a while and finally popped through the outer ring and Jessica yelped in pain, but allowed the man to push all the way in.

God, it hurt. Jessica had heard women, some of them her high school classmates tell how wonderful this was but right now she only wished it was over. As this thought crossed her mind the man began to pump into slowly at first and then picking up speed. She felt the stirrings of her pussy as he continued but all she could think about was that the cocks got larger every day. If this was painful, she did not think she would make it too many days.

Her first ass fuck ended shortly as he came in her. Her relief was short however and another stepped right in. He entered before her asshole could close down and his entrance caused her a lot less pain. By the time the fifth guy had cum in her ass, Jessica had found it to be a fairly enjoyable act and she herself came almost with each man. Towards the latter part of the day Jessica eagerly awaited each new cock. Over the next seven days she again serviced at least twenty men a day, some of them cuming in her ass and some on her back, ass and even standing behind her and filling her hair with their milky loads.

As the days passed Jessica waited for the large cock she remembered from her last day of cock sucking. So many men had cum in her ass, that she each night she could feel a constant stream of it dripping out of her asshole and down her legs. By the day the big cock arrived Jessica was in a constant state of orgasm. She was babbling about her ass, begging everyone to fuck her harder and when that large cock pushed its way deep into her, she squealed in delight and actually began to push back against him as he rammed in to her. She had one of her biggest orgasms of the week and remembers nothing more until she awoke the next morning, her ass sore and stuck to the sheets with dried cum.

Once again Kevin greeted her and asked her about her day and she looked at him and said.

“When do the cocks come in? They are going to fuck my pussy today right” she eagerly asked him.

“Yes, they are waiting outside now, and since this is your pussy which you have some experience using, I have increased the number of guys fucking you.”

“Thanks you sir, could we start now?” Jessica pleaded.

And with that Jessica managed to take twenty-five guys into her pussy in a every day for a week, once again cum was not oozing from her it was pouring but it did not stop her, she eagerly fucked everyman who came in and, in a way, was disappointed when the days ended. Each night Jessica slept well, but her hands continued to play with her pussy all night as she slept.

On the morning following her final day having her pussy fucked, Kevin asked Jessica what she thought would be next and Jessica shook her head.

“I don’t know but I am ready and willing to do what ever you ask of me. These past few weeks have awakened me and I love the freedom I have. So whenever you are ready, I am eager to start.”

‘Good, your training is paying off. This week you will be having multiples. In some case you will be fucked in your mouth, ass and pussy all at once, perhaps a woman will sit on your face while two men take your ass and cunt. If will be a mix and always changing, but you will be completely fucked. Are you ready?”

“Yes, Sir!”

And with that Jessica was led into a larger room and there were three men waiting for her naked.

She started with three guys. She took the guy with a fat cock for her pussy, the longer cock for her throat and the long but fat one for her ass. She had her ass man lay down and she mounted him, allowing his cock to force its way into her ass, the she leaned forward and had the other guy push his cock in her ass, once he was in, she moved a bit to get comfortable and then had the last guy stand in front of her and she asked him to fuck her mouth and throat. She asked that they all begin at the same time. Three cocks were pounding into Jessica at the same time, her pussy was being pummeled, her ass was full of cock and her throat was being regularly invaded by cock, she was in heaven and felt her own pussy start to lose control. It wasn’t story book, they did not all cum at once the guy in her ass came and pulled out, his cum oozing form her. This action was repeated all week long with Jessica receiving cum in her ass, in her pussy, in her mouth and sprayed over her entire body. She ate women, women ate her, she shared a woman with a guy, shared a guy with a woman. By the end of the training period she had cum in everything and on everything and she felt good, tired but real good.

When she awoke the morning after the last day of multiples, she was taken and bathed, oiled and perfumed and then wrapped in gossamer thin sections of fabric. Covered but not hidden she was taken to Kevin’s office. She walked in proudly and actually pushed her tits out in front of her as she entered. She noticed another man in the office and while she was not sure, she thought he owned the big cock of her training Kevin gestured to a seat and said,

“Well Jessica you have done well in your training and everyone of the men and women who trained you thought you have become an exceptional fuck, so the choice is yours. High class call girl, nice places, fancy resorts rich men, or the streets of any west coast city. It all up to you?”

“I need one more opinion, maybe two” Jessica said as she stripped off the fabric casually laid upon her and stepped to Kevin’s desk. She sat on the desk and slid around facing Kevin and spread her legs, “I want you two guys to take me together in the ass, and then you can tell me where I will be happy!”

She then motioned for the other man to come over. Kevin introduced him as Mark, his son. She had both men remove their pants and boxers and sit face to face getting their cocks close together. She had Kevin hold the two cocks together and Mark held her ass cheeks apart. She then positioned her ass over the two cocks and worked her way down. It was an effort and she screamed as the two heads fought to penetrate her ass, but Jessica had become persistent, and she now not only loved cock but she was beginning to realize she needed it. She felt the two cocks forcing their way into her ass, and she was almost certain that her ass would rip apart, the immense pressure being generated by these two massive cocks was almost beyond her tolerance. As she ground herself into them, kissing the Kevin’s face and neck as her hands roamed his chest and arms.

She was facing Kevin, her back to Mark as she continued to lower her ass onto their cocks, as they pushed in, she felt pain, worse then the first few times, but ignored it and allowed her ass to drop even further taking more and more of their massive cocks in her ass. God she was full. But she had not taken all of them, and she wanted it all so she forced her ass lower and lower as inch after inch of those huge tools penetrated her colon. She gave a last push and felt her ass cheeks touch Kevin’s thighs and she knew she had all of the two cocks and she smiled as she began to reverse the process and allow her self to slowly go up, and then back down. She increased the speed and heard Kevin say,

“Shit Jessica, I knew you were good but your ass is grabbing our cocks, I can feel Mark’s hard cock pressing against mine as you fuck and you are sucking the life out of them, oh yes fuck me. Fuck us”

Mark was merely grunting as his cock was enveloped in this process, his face was red he was trying to hold his ejaculation as long as he could.

Jessica slid faster and faster till she felt her pussy start to rumble and either Kevin’s or Mark’s cock started to spurt followed soon by the other. Two cocks were now filling her as with gobs and gobs of cum. She came as she felt the cum coating the inside of her ass and then just sat there enjoying the feel of the two cocks resting in her ass.

“Kevin, Mark that was wonderful. Guys tell me where do you want me the penthouse or the streets?

Mark waited for Kevin to speak but he heard only silence. As Jessica looked closely into Kevin’s face saw that he was not breathing, not moving and hollered for Mark to dial 911. She got up and went to the couch sitting there until help arrived. She was stark naked until Mark came to her and wrapped a blanket around her and she laid her head on the couch while they confirmed that Kevin was dead. He’d had a bad heart Mark told her, but he knew his Dad wanted to fuck Jessica after her training, he thought it would be alright evidently it wasn’t.

Jessica was lost; she walked around in a daze for a few weeks, staying at Kevin’s house not having any place to go. When she got horny she would seek out whatever staff was around and fuck them. Often one was not enough and she would find at least two sometimes three, gender did not matter, male or female she just needed to cum.

She knew she wanted to continue to fuck, and to make money doing it, but did not know how. Then one day sitting on the back porch of Kevin’s house Mark walked up and sat down and started to speak to her.

“Jessica, I am trying to decide what to do with Dad’s business. I have no head for finance, or for administration. Someone needs to take the calls and book the clients. Would you help? I saw the dossier Dad did on you, you have an MBA, right?”

“Mark, I will help you if you will help me, deal?”

“If I can do it consider it done!”

“OK I will set up and oversee the business but I need cock and I need sex, so I have to be one of the girls. I will do highbrow stuff but I want some gang stuff somewhere along the line every now and again. I need my face and throat fucked. I need to be called names, to be spit on and fucked without mercy. I need that Mark! If you can do that for me I will do this for you. ”

Jessica and Mark picked up the business and grew it. Jessica not only got all the cock she needed, she did a great job of kidnapping and training new girls for the company. Mark became a favorite cock for Jessica, she still loved its size and shape, next to Kevin’s it was the best cock she had had. She never married Mark and they never had kids, but they remained together for the rest of their lives.

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