A Chance Worth Taking - Rebecca, a short story by TheChameleon. Date added: 2012-01-18. Times viewed: 11172.
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Jake toyed with the idea over and over in his mind ever since he first read it.
Dominant Male Looking for new and curious submissive males needing to learn how to suck cock. Applicant must be very obedient, enthusiastic and willing to learn. He must also be able to suck cock for 2 hours straight. Exploration is a must and any hesitation not accepted. Once accepted, there is no turning back.
Jake was not into other men, he had just been browsing the ads, bored that night, but it definitely caught his eye. Do people really respond to these ads he wondered, would women respond to an ad like that? He finally decided what the hell, I will write my own ad, and the most that could happen is no replies.
“Man looking for bored women, housewives, and girlfriends, young, old, with or without their man’s consent to explore the wilder side of sex. I am into dominating and training curious females in the decedent ways of fulfilling their inner-sluts. Only the curious need apply. Let your submissive side take that chance, what have you got to lose except your inhibitions and virgin holes.”
Not bad he thought, and he hit send. It was now posted, all he had to do was wait and see if women really were as curious and sexual as they say.
Jake got up, went to pour himself a drink, and sat back down to surf the net and read some hot sexy writings. He had barely logged into his favourite amateur site when he heard the ping of an e-mail. He tabbed over and was shocked to see that within minutes he had a reply. Ping, Ping. Two more e-mails. Fuck, maybe he had been missing the boat on this thing.
He opened the first e-mail and it was from a woman named Rebecca and she said that she was married and her husband has become so busy working trying to succeed in the corporate world, he had forgotten her needs. She has always been interested in being dominated but had never confessed to anyone before. She NEEDED to be excited again and wondered if she could possibly be trained in the darker side of sex.
Jake e-mailed her back, asking for more details. How old was she, what did she look like? What was her sexual history, likes and dislikes, and finally, what were her limitations?
As he was checking the other two e-mails, Rebecca replied and for the moment Jake decided to concentrate on just the one.
Her reply stated she was just turning 40, shoulder length hair, medium built with slightly larger than average breasts, and as far as sex, she was a virgin when she married her high school sweetheart. She sucked his cock occasionally and they made love in the missionary position. She went on to say that it was recently that a girlfriend told her of some story sites and she discovered erotica and began realizing what she had been missing out on, and although scared, she is excited to explore new frontiers.
She said she was not sure what her limitations are and was open to talking and discussing options with him.
Now was the time to test her he thought. Send me a picture of yourself, and within minutes he had one of her. If the picture was even close to reality, he could not believe his good fortune. Auburn hair, green eyes and her tits were like she said, larger than average, ones you definitely noticed. She asked him if he liked it, he responded by sending one of himself.
Getting bolder, Jake told her to send a picture of her tits. He figured time to see if she obeyed.
Rebecca replied that her husband was in the den, to which Jake replied, I gave you an order, are you going to listen and learn, or do I seek a replacement?
About 5 minutes went by, and sure enough she sent him a picture of her fabulous tits.
They had to be 38 D, and the nipples were a pale pink color, and the size of a silver dollar. They were hard, long and looked like they needed to be abused in a very sexual way.
Next he ordered her to send one of her standing in only her panties, and she did.
Jake thought to himself, this is fucking awesome, and he sent a final e-mail for the night, telling her to meet him at a local coffee shop at precisely 2 PM the next day and to wear a red corset, stockings and heels under a trench coat and nothing else.
Once off line, Jake sat back, looking at her pictures stroking his manhood, the pre-cum running down the shaft soaking his balls and fingers. He pulled the foreskin right back, causing globs of pre-cum to ooze out of the slit tip. Not being like other guys, Jake liked to taste his own pre-cum and he scooped it up and licked it off of his fingers and in doing so, his cock started to throb on its own. His hand returned to his thick meat and wrapping his fingers firmly around the shaft, he began to move it up and down, his eyes fixated on the gorgeous woman he would be fucking tomorrow, and yes he was confident, he would be teaching her stuff that her mother never told her about. And all too soon his cock erupted, shooting hot white semen into the air, splattering across the computer desk.
Jake reached for the tissue box, and grabbing a handful proceeded to clean himself and his desk up, and headed off to bed, knowing the dreams of educating the lovely Rebecca would be playing all night long.
The next day, Jake was waiting patiently when she walked into the café. She had done well, and she looked exactly as told, a black ladies trench coat, stockings and heels.
She looked around trying to find Jake from his photograph and when she spotted him, she bowed her head slightly and walked over. Jake stood up, hugged her close, and lifted her face; looking into her eyes he kissed her. Not sexual, not forcing, just a kiss on the lips as if they were a couple. He pulled out a chair and after she was seated, he pushed it in. He was the consummate gentleman for now, and both knew later that would change as he brought her to the other side of decency. He asked her what she liked in her coffee, and he then went to the bar and brought it back.
Once he sat down, he took her hand and quietly asked her if she was ready for what lay ahead. She honestly answered she was unsure, scared even. Jake told her that for the first time, she could back out at any time, but any subsequent visits meant that she was his to use anyway he deemed fit, that he would end up not only training her, but owning her to some degree.
Rebecca shuttered at those words and inside she had to admit to herself, she had not even entertained that notion, that very idea that she would ever want to be owned, let alone by a man other than her husband. But as the idea sunk in, she could feel her cunt start to moisten.
As they drank their coffee, he pressed her, finding out about her sex life, and she sat there blushing confessing them all, not sure if others could hear them. If it bothered him, she did not notice it, he seemed so in control. The first time she sucked cock, she told him, 16, as a way of keeping her virginity until they were married. Did she masturbate? A little she replied, but always felt dirty. Has she ever watched her husband jerk off? No, she did not think he did that, why would he when he had a wife? Jake smiled and told her, all men jerk off, and if they say no, they are liars.
Soon, he smiled, held out for her hand and they stood up and left. He put his arm around her and the walked down the street about 1 block, and into the lobby of a very nice hotel.
Walking past the front desk, they headed straight for the elevator and soon were up on the 22 floor and in his room. Once they were there, Jake grabbed Rebecca and pushed her up against the wall, kissing her deep, his tongue pushing into hers, leaving her feeling weak and helpless. He stepped back and hands on her shoulders he pushed her down to her knees. Rebecca instinctively knew what was expected of her, but never having done anything like this in her life she was nervous. She looked up at him and told him that she was not a very good cocksucker, and that her husband only makes her do it when he is drunk.
Sensing her fear, Jake told her not to worry, that she would be fine and that over time, she would become an expert. With that he reached down, unzipped and pulled his cock out. Semi hard and it was still fatter than her husband’s cock.
Jake wrapped his hands in her hair and guided her face to the ever growing cartilage.
She stuck her tongue out to capture the first drop seeping out of the foreskin covered head. She realized she had never seen an uncircumcised cock, let alone sucked on one. Even the odour was different, and she liked that. His cock grew and soon the head forced its way past the skin, and exposing the purplish glans.
Not waiting he pushed it to her mouth, between her red lipsticked lips and past her teeth.
Not waiting to see if she would gag or not, he began to thrust in and out, figuring he was not going to give her a chance to change her mind and back out.
Rebecca started to lose her balance on her knees, and she reached around Jake to hold on to and she ended up with both hands cupping his buttocks. Jake taking this as a sign of enthusiasm instead of what it really was, began to thrust deeper.
The poor girl had only ever taken half of her husband’s smaller cock in her mouth and here was a stranger ramming at least 6 or his 8 inches down her throat. She started to gag and Jake realizing, pulled out to allow her to catch her breath. He asked her if she was alright, and she nodded. Good, now answer me; have you ever swallowed cum before? She shyly turned her head from side to side, and then quietly the word no came out. Have you ever wanted to? No she said. Well if you are going to become a slut, you have to start and today will be as good a day as any. Rebecca just nodded her assent. Jake lifted Rebecca to her feet, and then he told her to lose the jacket. She slowly undid the belt, then the buttons. Hanging loosely open showing the front portion of her corset, he could see the swell of her massive tits above the cups of the outfit.
Jake told her to continue, and she let the coat drop from her shoulders on to the floor.
She could hear his intake of air as he surveyed her body in this very erotic number.
His eyes sparkled as he ran them up and down her body and she instantly felt special and sexy, something she never felt from her own husband.
Jake reached out and slowly turned her around, letting his hands roam over hips, ass and then reach around and squeeze her tits from behind her, allowing his cock to push up against her round butt cheeks. Rebecca allowed herself to fall back into his arms, his wet cock now streaking across her ass.
Holding her from behind, he directed her over towards the bed, pushing her down so her arms were supporting her. He pushed her red thong to one side and placed his cock at the entrance to her puffy cunt. There was no denying she was fucking randy, the wetness running down her thighs giving it away. With her arms out stretched for balance, he pushed his way into her tight hole. He grabbed her hips with both hands and slowly and deliberately filled her up to the hilt. Once in, he stopped moving, reaching over her back, grabbing her hair and pulling her head back. Now you are about to become a slutwife. Do you know what that entails? Rebecca nervously said no. Well a slut wife is a wife who craves sex, needs sex, and it will please her lover with every ounce of her body.
Are you ready for this? Rebecca almost screamed out the answer, YES.
It was true, she was naïve in sexual matters even her own desires. Now she was being awoken and she loved it. With one hand wrapped in her hair and the other on her hip, Jake began to fuck her. He would pull his cock almost out of her, And then slam it back in, his balls swaying forward and slapping her cunt from underneath. Rebecca started moaning out loud, animal like grunts, releasing all of her pent up desires through her noise.
Jake was smiling to himself, and he knew now was the time, and he released her hair and he brought his hand down hard on her ass cheek. Rebecca was too far gone in her wanton needs now to resist. Hell, the first sting only excited her and made her even wetter.
When Jake seen her horny response to this, he smacked her again, and again. The more he spanked her, the harder back she pushed, trying to take every inch of cock he had, and wishing he had more. The harder they fucked, the more wild she got, and soon her tits fell over the cups of her corset. Her huge nipples long, hard and very thick, dragging on the bedspread.
Jake could not resist, he grabbed one of her nipples and twisted it hard. Rebecca’s eyes just rolled with ecstasy, feeling things she never knew, wanting more.
As Jake leaned forward, it must have changed the angle just enough, and he hit something, and that something made her expectantly shoot her cum all over him. It came so fast, so hard; it scared the hell out of Rebecca, never having really orgasmed with such a force before. She started to cry when the second one hit her, and it all became too much for Jake, and needing to keep true to his promise, he pulled out, spinning the crying slut around and shoved his twitching cock into her mouth. Not a moment too soon either, as he let go with a mighty torrent of the white jism. Spurt after spurt filled her mouth and being the first time, it was all too much and she started to choke and some ran out dripping down her chin and coming to rest on her tits.
Jake took her hand and placed it on his cock, letting her stroke it, getting every drop out and on her tongue. Once he was finished, he leaned down, kissing her, tasting his cum together, sharing it, and for a moment, it was as close a feeling Rebecca had ever had with another person.
Rebecca went to wipe the sticky cum off of her breasts, with the intention of licking it off her fingers when she was stopped by Jake. He looked seriously into her eyes, and told her, that she was to leave it there, let it dry. As part of her training, she was to go to a clothing store, go in the change room, and take the coat off, take a picture on her cell phone and e-mail it to him; she knew it was an order, not a request. Then she was to take another picture in her bedroom to prove she went home covered in sperm.
Rebecca smiling nodded her head like an eager teenager.
Jake asked her, so, are you ready to begin your real training tomorrow, to become a slutwife?
Her answer was a long deep kiss, and when they broke, she said try and keep me away.
Tomorrow at 11 Am give us enough time for day 2?
All Jake could do was grin from ear to ear, and he wondered to himself, if the first trainee is this good, I cannot wait for the others.
With that, Rebecca put her coat on, and left to do her homework, and Jake walked over to the desk, opened up his computer and opened the second e-mail applicant.
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