The Contract 21

The Contract

This story is written for the 2019 Literotica Geek Pride Story Event. It's a crime story, and it may be too long for some people's taste, at 18,000 words. It contains some violence and mayhem, group sex, and incest. Of course, there's the always already presence of Exhibitionism and Voyeurism. It's not SciFi, nor Fantasy. I'm not sure in fact where to put it, so I put it in my favorite rubric, Exhibitionism and Voyeur.

If you read it, please vote and -- especially -- please leave a comment! All comments are read and taken seriously, even the gratuitously nasty ones of that most frequent of all commenters, Mr. Anonymous.

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Sally was having trouble getting dressed for her big night out. What do you wear for the date when you are finally going to kill the brakes, and let the man decide what he wants to do with you? Do you wear a skirt and blouse for easy access, or a skirt and sweater for even easier access, or low riding slacks, or jeans, and a gypsy top for sex appeal, or a sexy dress that hugs your curves and in which -- basically -- you look hot? Sally had seductive outfits in each rubric. She didn't want to look cheap, just to send out the message that if he wanted what the clothing concealed, he could have it.

The key, Sally decided, was the accessories. It always comes down to that, doesn't it? A crop top and a tight skirt would show off her tramp stamp tattoo, but that would look cheap, and John didn't even know about the tattoo yet. He might not even approve, as he had good two shoes tendencies. It was the wrong way to go. Pants were sexy, but maybe too hard to get off, should she get lucky and drive the guy into a lust fueled craze.

Did it matter? She knew by now the guy would jump at the opportunity to add her to his list of conquests. Admit it, Sally, she told herself: She was dressing more for herself and the other women she would see on her date than she was for the guy. He was already a sure thing, when it came to sex. The only reason they hadn't yet done the deed was her own reluctance. The reluctance was now gone, she silently giggled to herself.

No, the key was the jewelry, the hose, the sexy lingerie, and especially, always the most important in her mind, the perfume. Maybe a necklace that would call attention to her boobs? As if she needed that with John! She giggled at her thoughts.

John was a sweetheart of a man. He was kind, and generous. He was never in too much of a rush to help out a tourist, he would often offer his seat in the subway to an old man, or a pregnant woman, or to just about anyone who looked exhausted and was dead on his feet.

Best of all in Sally's eyes was that he always gave to the many panhandlers one would come across during the morning and evening commutes. He gave away at least $20 every day, usually in $1 increments. Sally loved him for that attitude.

Sally wondered if his sexual style would reflect his personality. John was certainly a great kisser, she already knew that. She also knew he was frustrated. She had put off sex for much too long. John was getting restless, and since both he and Sally were young: she in her mid-twenties, and late twenties or more likely early thirties, or maybe even mid-thirties for him, dating for six weeks and not having sex was fairly unusual in today's climate. Sally knew it was time. Truth be told, it was past time.

Sally had been on the pill now for two weeks, so it had taken effect, and in case John was a 'bareback only' kind of guy, she was ready for him. For the sake of potential disease, however, she was hoping he'd use a condom. She had extra condoms in case he was stupid and didn't realize how many times she liked to go at things, once she finally gave herself to a man. She really had to stop going on and off the pill. It was hard on her system.

While she chose her outfit and its accessories, and her black belt with its big sterling silver buckle came to mind, she began to wonder what she'd wear the subsequent night with Blake? It was time to give him a taste of what she had to offer, too. Sally was fairly confident the men would like her sexual talents; thank goodness there's no Yelp pages (yet!) rating a girl's bedroom talents, but if there were, she was fairly sure she would have a five-star rating even if all twenty-three of her former lovers rated her.

Sally liked the idea that she had twenty-three former lovers. She thought of her sex life as being 'twenty-three and me.' Adding John would ruin the poetry, and she'd be up to twenty-four. What would she be then? A twenty-four kinda whore?

Twenty-three might seem a high number, but since she began at age fourteen, it did not seem that high to her, only around two a year, and if you discount the seven lovers of her college freshman year (here she was including the one time four-man gangbang at the Delta Kappa Epsilon party [during her hyper kinky period] in her calculations), it then looks reasonable?

John Higgins came on time. That was another nice feature of John: He hated to keep people waiting. She greeted him in her robe, wearing lingerie underneath. "I'm all dressed," she said. "All that's left are my clothes."

John looked puzzled. He didn't understand that most of the time a girl spends getting ready is spent choosing the outfit, and then it's the bath, the body creams, the make-up (especially the eye make-up), the hair, and the perfume that takes a while. This night the chosen scent was to be Coco, by Chanel. Coco just barely edged out Twilly, of Hermes. She had had a long internal debate about the perfume decision; she had considered it and reconsidered it all during her long work day. It was a nice distraction.

She was about to apply the Coco when she decided to wear a colorful Hermes scarf. Yes, a touch of color around her long neck would add a bit of oomph to her outfit, and hide her revealing cleavage, at least most of the time! Every so often John would get a peek as she would adjust her scarf. Sally always loved to tease. That tipped the scales for Twilly. Sally always tried to stay in one designer's wheelhouse whenever she could.

Greeting John in her lingerie hidden behind a robe allowed Sally to give him a foreshadow of her plans for later in the evening. She excused herself, going to her bedroom in her tiny apartment, but she left the door wide open. Once in the bedroom she dropped the robe, giving John a tantalizing view of her lovely, curvaceous body, clad only in lace lingerie that did little to hide her delightful feminine charms, the very charms Sally knew John lusted for.

John watched as she slowly pulled her hold up stockings up her legs. The action emphasized her thin but nevertheless shapely legs, and he continued to watch as she stepped into her red dress, with its low-cut front, made of red mesh above her boobs. The dress hugged her curves and it left not even a scintilla of doubt that she was a genuine woman.

Maybe she was a goddess, that was debatable; John could have argued the goddess case from either side. That he adored her and wanted to bed her however was not in doubt. He happily zipped up the back of her dress, noticing the little hook that held her delicate bra clasped on her body, as he looked forward to undoing that same zip and clasp later in the evening.

While John was watching Sally dress, Brian the assassin was cleaning his gun. His gun had one more kill in it, and then he would need to go to Virginia and get a new one. He'd want another untraceable gun, of course. He knew just the vendor he would see at the gun shows. The vendor always wore a bright red NRA cap. If you're a professional assassin, every day you bow down and face Fairfax, Virginia.

Brian tried never to use his own gun. His preferred method was to steal someone else's gun. His favorite targets for theft were gun collectors. Often, they did not even realize they had been robbed for quite a while. The police would seize the gun as evidence in the killing and then contact the victim of the theft, possibly subjecting him to unwanted scrutiny, too. Brian found the entire process to be quite entertaining.

His new target was this milquetoast John Higgins. Brian had standards. He would refuse all contracts on women and children. He lost a lot of business having his male chauvinistic ethics, since there were a surprisingly large number of rich men willing to pay $100k and higher to have their wife bumped off. If the price was high enough, sometimes he would need to bend his ethics. (He never though took out a contract on a child.) Since a divorce would involve a loss of much more money than a mere $100k, and nothing was more important than money to these people, Brian thought of his rates as a bargain.

One time he offered to seduce the wife instead, complete with photo evidence of the sexual acts themselves. That, he had to admit, turned out to be a most enjoyable solution. He concluded that the man was an idiot to let go of such a tiger in the sack. He supposed, however, that outside of the sack she traded her tiger persona for that of a pecking hen? The two of them, the ex-wife and Brian, still got it on from time to time, too. That only worked once, however. He could not be the evidence in more than one divorce after all. It would get around.

Most of his business involved subtlety. "Make it look like an accident," was the standard request. The 'accident' murders were fun, because he got to be creative. Sometimes a victim would look for a subway train coming. For example, when it was both late at night and the man had been drinking, and if the subway platform was deserted, then Brian-the-Assassin could use Plan A. All Brian would need to do would be to give the target a quick shot of a fast-acting paralytic. Then he would give a hidden but healthy push entailing a consequent fall onto the tracks right in front of the train barreling into the station. The police called it an accident every time.

Another time Brian took over a Lexus via a remote control that resembled a play station. The unfortunate driver frantically tried to prevent the horrific accident that ensued, but despite the driver's efforts, Brian made sure the accident was fatal. For some reason the airbag did not inflate. Brian of course knew the reason for the unusual simultaneous failure of both the seatbelt and the airbag.

His new contract however required the opposite of subtlety. Flamboyant murder required less of an imagination, but it provided more pleasure. It also involved more risk. He would need to arrange for someone else to take the fall.

Whoever it was who wanted John-the-Milquetoast dead wanted the whole world to know it was murder. Brian was almost too happy to comply. It would not be tonight, since John-the-Milquetoast was taking out some sexpot, and Brian would much rather seduce the grieving lover than have to kill her too, as collateral damage. She might however make a sweet fall guy for the murder, especially if John were to rape her. Sadly, though, it was obvious rape was not the style of John-the-Milquetoast. Even date rape was not going to be an option.

Sally discovered that John's sexual technique meshed with his personality. He took things slow and methodical. Sally imagined the seduction formula John would use. This amused her, and she even decided to plan out the seduction minute by minute. She would see how well her plan matched up with reality and give herself a pat on the back if it did. Maybe John would give her a pat on her ass, if she was lucky?

It was as if John purposely followed the playbook Sally had made up in her mind. They began with kissing, and then some feeling her up with her still fully dressed. John pulled her to a standing position, turned her around, and he unzipped her dress and at the same time unhooked her bra. A minute later she was standing in panties and hose, her back to John. He reached around her to fondle her tits. He spun her around and sucked on her nipples. Sally was batting a thousand.

The moment of truth arrived. Would he or wouldn't he? He did! Off came her panties with nary a squeal of protest, and John began to understand tonight was the night! Then the big bet paid off. Yes! Sally was thrilled to learn firsthand (so to speak) that cunnilingus was in John's playbook! He lapped away at the now prone Sally, and she moaned out her appreciation in a volume John could not help but appreciate. Sally had guessed wrong about the cunnilingus, but boy was she glad she was wrong!

Sally was close to a climax when John stopped and put a rubber on his cock. Wrong again! Sally was sure he would hint or ask for a blowjob, but no, he wanted to proceed to the main event. Well, good for him, Sally thought. Sally could tell John was nervous. Was this too far, too fast? Sally could see the wheels turning in his sweet mind. He needed encouragement.

"Come on in, big boy. The water's fine," Sally said. John looked puzzled, so Sally made it explicit. Apparently metaphors are not John's thing, she giggled to herself. "Stick it in me, John. I want you inside me. Please?" Sally's voice was the breathy voice of a sexually aroused woman.

No woman had ever before actually asked John to fuck her, but now Sally had done exactly that! Now sure of himself, John plunged in, and having her warm, moist, velvety cunt surrounding his rubber encased cock was about the most thrilling sensation of his life. It was almost as good, no it

was

as good, as the time he laid Stephanie, and back then he didn't even use a rubber! As good as Stephanie? Wow. John was in heaven as he happily pumped his little heart away.

Sally knew men liked it when she moaned, and she wanted John to enjoy fucking her for his first time. She hammed it up as much as she dared, but suddenly she realized acting was not needed. She had become really into this! Somehow the affectionate, even loving way John possessed her willing body pleased her no end.

Little by little her arousal built, as John grunted as he plowed into her, harder and harder, each thrust seemingly deeper than the one before, almost as if his relatively small cock was growing as he twisted it around inside her, screwing her lovingly.

"Milquetoast gets the girl!" Brian uttered aloud, as the cameras he had hidden in Sally's apartment allowed him to watch everything on his laptop. Surprise shocked Brian as he watched Sally climax during one of John's particularly strong thrusts. Brian knew Sally's orgasm was the real deal. God, she looked sexy when she came. Milquetoast could do that to her? Maybe he should rethink his nickname for John Higgins. Perversely Brian was glad John was enjoying what was likely to be the last fuck of his life.

Brian had taken the precaution of installing video feeds throughout Sally's tiny apartment. They connected via Bluetooth to a computer he had placed in a hidden corner of her apartment, connected to a special power source, a broadcast apparatus that had the range to reach his hotel room close by. He had not thought about the benefit of peeping on Sally, but he had to admit it was enjoyable, especially now that she had provided him with one hell of a sexy porno quality video. They're so much better when you 'know' the people, and they're not acting, but truly having romantic sex. Life is good, Brian thought. While it lasts, that is, and again he chuckled.

John did not spend the night. Brian was not surprised. Milquetoasts rarely do. He watched Sally get dressed in the morning, and he watched her stop halfway through to jill off. This was getting better and better! Maybe he could tip off some prison guards that she would be delicious? Nah, they'd figure that out themselves. They're not rocket scientists, he thought, but they can spot a sexpot a mile away without any help from him. She'd enjoy her time in prison. She'd have more than enough sex, he was sure!

Brian maintained his surveillance. It's all part of doing a good job. When he saw the luscious Sally getting ready for a date the very next night, his respect for John (no longer thought of as John-the-Milquetoast) increased yet again. When the man entered and Sally played the same trick of greeting him in lingerie and letting him watch her finish dressing for the date, and the man was a different man, Brian was truly surprised. He had underestimated Sally!

This was a warning sign. He had underestimated John-the-Former-Milquetoast, and also Sally too? He was not as good at this as he had thought. Well no matter, let's see how things evolve, he thought. Maybe this was in fact an opportunity?

Sally felt she had to choose between John and Blake. They had such different personalities! John was loving, careful and respectful. He was charming, a good person, and in general a wonderful man. She had not expected it, but he was also a good lover. Her orgasm had been genuine, a rare event for her. Blake was different in almost every way.

Blake was a man of action. He was aggressive, and he knew his mind. He was a back-stabbing Wall Street success story, reeking of wealth, and not at all modest in flaunting his nouveau riche riches. He wanted women to resist him at first, and then to conquer them. Sally was perfect, if unwitting, for that role. Torn between loving his take-charge, dominating attitude, and appreciating the sweetness of John, she felt schizoid, to be sure, and she could not decide.

She decided it would come down to the sex, and she would choose the better lover. They were both good men, but they were also apples and oranges. They had such different qualities, she felt it was impossible to choose which man she wanted to be her exclusive lover.

Even knowing Blake was an aggressive, dominating type, she was still surprised by his sexual style. Surprised and enthralled. While she was dressing for the date, and teasing Blake with her lingerie exactly the way she had done with John the night before, Blake entered her bedroom and in a surprise attack he tossed her body onto the bed, lifting her as if she were a child's doll.

He fell on top of her prone body and showered her with passionate kisses, which Sally eagerly returned. His hands slipped under her panties and instantly found here slit. Without even a little teasing or in fact any foreplay at all, Blake shoved a finger into her snatch. He smiled at finding that she was already wet!

Brian, watching via his video feed, switched to another camera that focused on Sally's face. This woman was something else! It was obvious she enjoyed being manhandled. She clearly loved the sweet loving manner of sexual conquest of John-the-No-Longer-Milquetoast, and now he could see that she also loved Blake's rough style.

Uh-oh, is Blake going too far? Brian watched with glee as Blake cut and then ripped the lingerie off Sally's sexy body, ruining it in the process. Blake carried a switchblade knife? Who was this man? The knife gleamed as he held it close to Sally's throat, and this woman must have had ice water in her veins, since she giggled with glee! Brian was scared for Sally, he needed her alive for his plans, but Sally showed no fear at all! Who was this woman?

Blake undressed, keeping Sally still at knifepoint, and then with no rubber he used the switchblade to urge her legs apart. Sally was not resisting, anyway. She wanted this. Blake plunged right in, all the way. His cock was bigger than John's, maybe 6 inches plus a little, but in addition it was thick. Sally groaned in pleasure.

Blake fucked her hard. He pushed her around on the bed with his cock, and her head ended up banging against her headboard. Her generous boobs bounced on her body. How would Sally respond to this? She answered his question for him even as he asked it.

"Oh, lover, you're so good! Oh my God. Ohhhh FUCK!" she cried out as she exploded in an over the top orgasm. All this just minutes after Blake had burst into her bedroom.