The Challenge

A story by a new author caught his eye. The story detailed how a wife cheated on her husband who was away for a long time. It was fairly erotic but felt rushed, as if the details were too taboo to write about. It wasn't the story that caught his eye so much as the profile picture. A simple click on the author's profile offered him a glimpse of her sexy body, modestly covering her breasts. It was her eyes that really struck Jake, though. She had on no make-up and her light brown eyes dazzled the screen with a sensual glow that was more erotic than her story. Taking a chance he emailed her to tell her he liked her story but was more impressed by her picture. She had on a wedding ring but a compliment does not mean anything. Jake knew you had to start somewhere and though it was probably a long shot, a compliment could get him some action.

Bing. New mail. It was from her. Ashley had replied back to thank him for his interest in her story and picture and asked what else he would like to see. Maybe she was just flirting, maybe she was serious. He replied that a woman's pussy was the most beautiful thing especially since he loved pleasing a woman orally. If a nice looking pussy was accompanied by a nice pair of nipples, it was like heaven. Though he was already at work, he hoped the day would become interesting.

Waiting all day for a response, work seemed to slow down time and working overtime did not help. No time to check emails at work. He could not wait to check his computer when he got back home but nothing. After a quick dinner, Jake fell asleep watching TV. He woke up in the middle of the night to pee and decided to check his email. There was a new message and it was amazing. The pictures were of the smoothest labia he had ever seen, slightly spread to show the clitoral hood but not the inner folds. The next pictures were of the most perfect nipples, raised and round, sweet and red against the milky white skin of her breasts. Jake was glad he had peed first because he became instantly hard. The message that accompanied the pictures was very simple "Now you have seen mine, you need to show me yours."

So there he was at 3 am with a really good hard on. He hadn't played "show me yours, I'll show you mine" in a very long time. A few clicks of his digital camera and his cock was throbbing. He had started stroking himself during the photo session and got some great pictures of pre-cum oozing from the head of his throbbing cock. Jake decided to wait until later that to send them, just to make her wait a bit. He fell asleep in front of the computer staring at her gorgeous pussy, imagining his tongue running all over it, imagining what she would taste like. He woke up several hours later, still hard and throbbing. After sending her some pictures, he continued the photo session and started using slow, deliberate strokes relieved the pressure that had built up in his balls throughout the night. Spewing his milky white cum over his hand, finally satisfied with the photos, he realized he had lost track of time.

Jake was almost late for work but managed to squeeze in a quick shower and bite to eat. After what seemed like an eternity, lunch time finally came and there was a message from Ashley. "Enjoyed your pics and hope to see more as well as more of you. The challenge is to take pics of you or any part of you in places that define who you are....at work, favorite club, etc. Here is me at work" It was a very simple picture, she was sitting in a chair with her skirt pulled up, no panties, and her finger tip on the tip of her clit. "thinking of you" was the caption. He could only see a little of the background of her office but it appeared that someone in an ill fitting suit was right behind her, his back towards her. If he only knew. "I accept your challenge but do not have my camera with me now. I will not disappoint.."

And so it began, picture for picture, an exchange of erotic shots. It was not always easy for him to get a naked cock shot to send to her but she managed to forward Jake more and more pictures of her nipples and pussy. After several weeks of exchanging images, a picture caught his attention. It looked like a statue in a park near his apartment. Some Civil War hero pointing to something. In this pic, he was pointing right at her pussy. She had somehow managed to climb on the statue and get a photo with a marble finger in her slit. There was only one course of action for him to take.

The next night, he found the statue in the park. Just before dusk, the park is fairly deserted. Jake climbed on the statue and placed his cock inches from where her pussy was just a day or so ago. He sent her the photo saying, "I am not stalking you but I know we live in the same city. Would love to meet you, just for coffee. The next step is yours to take." Jake was excited with anticipation and nervously awaited her response.

"I also would like to meet you but am afraid that I would not be able to control myself. Your cock is magnificent compared to my husbands. I don't want to cheat on him."

"I did not ask you to a hotel or anything. Just a public place, a little coffee. I have seen your pussy all over my city and would just love to match your smile and eyes to the images I have seen."

"I do love my husband and I would never want to hurt him. If it is just coffee, I will meet you. But nothing more than just a little coffee."

"I promise you, I will be the perfect gentleman. I will not take advantage of you. My cock will stay in my pants. I just want to hear your voice."

The arrangements were made for Friday, 3 days from now. Her husband would be gone on a business trip and so she would not have to sneak away while he was home. No pictures were exchanged in those 3 days and as much as he wanted to whack off to all her previous pictures, he didn't. If the night ended up the way Jake had hoped, he would fill her completely with cum. Friday couldn't come soon enough and neither could Jake.

At last, Friday arrived and he had a reserved a table at an outdoor café. Jake arrived a little early to make sure he not only got a good table but also to watch her arrive. She was on time and unbelievably sexy. 2 inch black heels, black pencil skirt which hugged her thighs and hips like a second skin, a tailor made white blouse with no sleeves, unbuttoned to show just a glimmer of cleavage without appearing sluttish. Her auburn hair was in loose waves just past her shoulders. As she sat down, her nervous look melted into a warm smile and with her perfume, Jake was aroused and erect.

They drank coffee for hours, talking about themselves, their jobs, their backgrounds. It was as if they were old friends catching up on things. She sadly told him she had to get going home but really enjoyed meeting him and hoped they could do so again. Jake paid the bill as she went to use the restrooms but they were out of order. (A benefit of arriving early and tipping the busboy) She said she really had to go badly and didn't think she would make it across town in a cab. He told her my apartment was just across the street and she could use his washroom and then he could call her a cab. Initially hesitant, her bladder won the debate and they headed up to his apartment.

He ushered her inside his 5th floor apartment and showed her the way to the restroom. While she was in there, Jake opened a bottle of wine and stepped out onto his balcony with 2 glasses. He had to play this just right or he would miss the opportunity to eat her pussy and to fuck her madly. Initially she was resistant to the wine but he said it would be nice to watch the sunset and relax for a few minutes. He told her he really enjoyed her company and just wanted a few more minutes. Despite her protests of just meeting for coffee , she finally accepted the offer of the wine and the view from his balcony. The city was a flurry of activity, the sun slowly setting behind the ominous buildings illuminated with a rainbow of lights. They slowly sipped the wine in silent appreciation.

"It's breathtaking," she whispered.

"It is indeed," he replied but not referring to the city but to her beauty.

She shivered a bit. He stepped behind her and wrapped his arms around her waist, holding her close, "Here, let me warm you up." They were still for a few more moments when he ever so lightly kissed the side of her neck. The mixture of her perfume and hair and the city at dusk was too much for Jake to control myself any longer. She responded with a slight moan and so he kissed her neck again, this time a little longer. Another moan. He brought one of his hands to her breast and to his delight he could feel her unrestrained nipple straining against the fabric of her blouse. The lacey material of her shirt did little to hide her naked nipple. Jake became more aroused knowing that she was not wearing a bra. He gently massaged her breast and nipple eliciting more moans of pleasure and desire.

"Wait...please. I am married. I want to try to be faithful, " she moaned

By now he was sporting a huge hard on. Jake stopped kissing her neck and lowered his hands so they were just around her waist again. His mouth was next to her ear. As he push his bulging cock into her ass he began to whisper into her ear, "I will only do what you ask me to do. I want to lick that fabulous pussy. I want to make you cum again and again with my mouth. I want my tongue to feel your sweet essence as you cum. I want to lick your nipples and suck on them. I want to squeeze and pinch your nipples as my tongue licks your clit." All the while, Jake kept my hands around her waist squeezing her a little tighter so he could nuzzle his throbbing shaft against her ass. "I told you I would not take my cock out of my pants but I can still give your more pleasure than you ever dreamed could happen." She moaned again and began to gyrate her ass against his cock. Jake slowly worked his hands up her blouse to the top button and began to slowly open her blouse. He gently began to massage her breast being careful to not touch the nipple just yet. She turned her face towards him and they began to kiss. Their tongues swirled into each others mouth, and he began to rub her breasts a little harder and rolled her nipples between his fingers. They were swollen and throbbing and as Jake pinched them, she groaned into his mouth and pushed her ass harder into his crotch.

He continued to massage her breasts and nipples with one hand and slowly moved the other to the small of her back. He found the zipper to her skirt and lowered it gently. In one movement, Jake grabbed the sides of her skirt with both hands and at first wiggled it past her hips then knelt down behind her as he lowered her skirt to the floor. He eased her feet over the skirt and spread her legs, her magnificent ass was just above eye level and he could see her pussy lips bulging defiantly against the small whisp of her black thong. Starting with her calves, Jake ran his hands up one of her legs and down the other. With each pass, he spread her legs a little further until she had to lean forward a little and grasp the railing of the balcony. This forced her pussy to be right at eye level. Gently, Jake reached up between her legs to her stomach and caressed her smooth skin as he approached her thong. He lightly allowed his fingers to just barely skim over the fabric which was now damp. Grabbing her hips with his hands, he moved his face towards her body and began to lick her labia through her throng. She grasped the rail harder and had to bend her knees slightly as she yelled "Oh gooodddddddd!!! Please....don't... stop!"

But he did. Jake moved his face away from her and stood up. The bulge in his pants was throbbing against and he nestled it into her ass. He leaned over her back and began to rub and roll and pinch her nipples. As he did this, he pulled her back into a standing position and slid his hand towards her wet slit. Through the fabric, Jake began to massage her clit. She reached down and pushed his hand harder onto her clit and moaned "OOOHHH...I'm cuming ....ooohhhh.....ahhhh!" She leaned into him as it seemed her legs could not hold her weight anymore and she shuddered for several seconds as his fingers were treated to a flow of her sweet nectar. Jake whispered in her ear that they should move into the bedroom and she could only just nod in agreement.

He laid her down on the bed with her legs dangling off the side. Jake began to kiss her calves and slowly move his way towards her pussy. The aroma of her musky fluids was overwhelming and his cock throbbed even harder against the fabric of his pants. He began to lick her labia through her thong and inserted his tongue into her slit as far as the lace would allow. She groaned, "Fuck me right now... I need your cock in me..." Jake grabbed her thong and pulled it off her soaking pussy. Her outer lips were puffed out, her inner lips were spread revealing her moist, throbbing hole. He delved into her folds as deep as his tongue could go and was treated with another orgasm, a torrent of her sweet juices now coating his chin and face. Jake continued to lick her lips and her vault and occasionally would lick around her clit. She got closer and closer to firing off again but each time he would pull pack a little. After several times of doing this he sucked her clit into his mouth and began flicking it furiously with his tongue. She wrapped her legs around his head and squeezed him tighter into her pussy. Her backed was arched, she had her arms stretched to the side clutching the bed sheets. Her moans became louder and louder until she could make no sounds anymore and he felt her legs loosen. Jake stepped back a little and watched her shudder a few more times. Her chest and face were flushed, she was glistening from sweat and her breathing was little more than panting.

As she recovered, she whispered, "I want you to fuck me now. I want you to stick your cock in me and fuck me hard."

"I can't. I promised you I wouldn't take my cock out of my pants. I wouldn't want to break my promise."

She sat bolt upright and dove for his crotch. Her hands trembling from rushing and from her post orgasm bliss, she fumbled with his belt but eventually undid his belt and zipper and pulled his pants to his ankles. Jake's cock strained against his boxers which were very damp from precum. She pulled off the boxers, freeing the throbbing shaft which bobbed up and down slightly right in front of her face.

"I need to feel your cock in me," she purred as she started stroking my shaft.

"For the record, I didn't take my cock out, you did," he replied as she started to lick his shaft and take his head into her mouth. As good as it felt, Jake pulled her head back and stood her up. He did not want to lose control of her.

"Listen, if you really want this, you must do everything I tell you. There is no way to say no. I will give you orgasms like you have never had before but you must let me do everything I want to do to you."

As she stroked his cock, she nodded her head. "Anything you want is yours, I just want your cock inside me." Jake knew he had her.

"Lay down on your back on the bed with your head hanging off slightly," he commanded her and she replied. "Now open your mouth and suck me like you've can't get enough."

She open her mouth and began to suck the head of his cock. Between the precum and her saliva, it wasn't long before his entire shaft was glistening. She would just take in the head and suck it and swirl her tongue around the tip while stroking him with her hand. Then she would take the whole shaft in, sometimes gagging a little and having small tears form in her eyes. But she would continue to take him in further and further until his balls were slapping her across her face. As she continued to work his cock, Jake reached down and started to pinch her nipples which increased her sucking motion. He started to thrust into her mouth and ram his shaft completely into her mouth. The whole while, she kept sucking and licking He reached down to her still soaking pussy and started to finger her. She started to moan and groan and he knew she was close to orgasm again. She reached around his waist and grabbed his ass with both hands, pulling him even closer to her. As Jake felt her velvety folds start to contract and her hips started to writhe beneath his fingers, he thrust in and out of her mouth. His balls started to tighten up and he erupted in her mouth. Wave after wave of cum jetted from his cock. Initially she gagged a little but kept sucking and swallowing every drop he gave her. She was coming down from her orgasm and lay there still quivering a little but smiling in complete satisfaction.

Jake moved around to the other side of the bed, grabbed her ankles, and pulled her towards him so her pussy was at the edge of the bed. He still needed a little recovery time. Jake pulled a vibrator (a souvenir left over from a previous girlfriend) from his night stand and started teasing her pussy with it. Barely touching the opening of her swollen cunt, then running it up and down her labia, then teasing circles around her clit. She was going crazy and kept begging for him to stick it in her. He obliged and put it in her pussy nudging the g-spot. She started becoming very wet again and his shaft started to spring back to life. Jake buzzed her clit for a few minutes then plunged the vibrator back into her pussy. It was dripping wet. As he rubbed the head of his cock against the opening of her pussy, she started to thrust a little towards him. He only just had the tip of his head in her when he took the vibrator and rubbed it against her asshole. "No, not there, even my husband has not fucked my ass," she protested.

"Remember, you must do everything I tell you... It was your choice." Jake pulled back a little leaving her both holes throbbing, waiting. After a few seconds, he rolled his thumb in circles over and around her clit. "Yes, yes, yes... do whatever you want."

Jake stuck the head of his cock back into her pussy and the vibrator at the rim of her ass. He continued to rub her clit and she tried to thrust her pussy at him, but he kept backing off a little. Finally, he put his rock hard cock all the into her vault with one long hard thrust. She came instantly, her hips were writhing, she was biting her lip and moaning "Oh god, Oh god, it feels so good!" As she started to come down a little, he thrust the vibrator in her ass as far as it would go. He could feel its movement through the thin wall of her stretched out cunt. She came even harder this time, her hips were lifted off the bed, her legs wrapped so tightly around his body he could barely breathe. "OOOOHHHHHHH FUUUUUUUCCCCKK! OOOOOOOOOHHHHHHHHHHH GAAAAAAAAAAWWWWWWDDDDDDDDD!" Jake just stood there balls deep in her pussy as she squeezed his cock with all her might. He pulled the vibrator out, letting her come down a little. She relaxed her legs a bit and then he started thrusting into her.

The first few thrusts were hard and deep as she rode out the rest of her orgasm. As she relaxed a little, he started to thrust only an inch or to for a few thrusts and then drive all the way into her a few times. Jake kept changing the rhythm and pacing and her pussy just kept squeezing his cock. He grabbed her inner thighs with his palms and pushed them as wide as they could go while starting to massage her clit with his finger tips. It was time to fuck her good. Jake increased his speed and hardness of his thrusts. He was pumping her as deep as his cock could go. Thrust, groan, thrust, moan, thrust "Oh, Oh, Oh." His balls were slapping her ass. Slap, thrust, slap, thrust, groan. She started to contract again amid a torrent of her own juices. He just grabbed her by her hips and jack-hammered into her as fast as he could. With one final deep thrust, he unleashed jet after jet of hot cum into her pussy and she responded by wrapping her legs around him again and just moaning until he had shot his entire load.