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Intimate Fantasy

Category: Anal Sex
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After several weeks of flirting and sharing sexual fantasies on Lit, the Massachusetts lawyer had become obsessed with the sexy young nursing assistant from the deep South. They had shared one of his deepest fantasies, the fantasy of having his ass opened by a strong, firm yet gentle woman. The more they discussed it, the more his urge to live out the fantasy intensified.

Yet, that did not explain the action that he decided to take. Of course, he could not experience this fantasy with his wife, as much as he loved her and was committed to their marriage. She was very conservative and was put off by any suggestion of anything at all kinky. If he broached this idea, she would be thoroughly repulsed. He could always go to a professional. There were many advertisements that promised the pleasure that he yearned for. But that, somehow, would not be the same. He needed someone who engaged in the act for pleasure, because she wanted to share the experience. And the idea that they both would have the experience for the first time, that they were both “virgins,” in that sense, made it too much to resist.

On a cold, sunny winter morning, he found himself heading for the airport instead of the office. He was 5′ 10″, 170#. Trim, distinguished-looking in his suit. He kept himself in shape, working out regularly in the gym. Neatly trimmed reddish beard. Thinning hair. Cool grey eyes. He waited patiently through security at the airport. A confident stride as he walked through the airport, carrying only his briefcase. Comfortable with the familiar routine of boarding a plane.

As he sat on the plane, he found it hard to concentrate on the work that he had brought. What was he doing here? Flying a thousand miles to meet someone he knew almost nothing about. To engage in an act that most people would find offensive. This was not his life. You can’t just take a day off from reality like this, to, to……

Yet, when he thought about what he was about to do, he felt a tingling inside. An excitement that began in his prostate, and ran through his testicles. His penis grew hard and pressed against his slacks. He covered it with some of his papers and tried to get some work done. His mind, however, kept drifting back to the woman he was about to meet. A woman he knew so little about. All he knew about her was that she was a nursing assistant, she had full, lovely white breasts, and that she shared his most intense, intimate fantasy. He pictured what it would be like to be bent forward, in front of her, his hips in the air….

His reverie was interrupted by the bump of the wheels at the plane landed in Montgomery. He was in a daze. It all seemed so unreal. That he had flown hundreds of miles to see someone he really didn’t know. That he was about to open himself up in a way that he had never done before. He found himself at the car rental desk, with no memory of having exited the plane. He found it hard to talk to the rental agent. He felt like she knew why he was there, that it must be obvious to everyone, that everyone must know that he was about to be taken. The rental agent, however, acted completely normally, and the Massachusetts Lawyer managed, to conclude the arrangements for a car.

Sitting behind the wheel of the rental car, the Lawyer found that his hands were shaking. Would he be able to go through with this? He took a deep breath, placed the directions that She had sent to him on the seat beside him, and studied the route that he was to follow. He pulled away from the airport and onto the highway. He found that his mind was calmed a bit by the need to concentrate on the unfamiliar roads, but he still noticed neither the scenery nor the weather, which was much more comfortable that what he had left behind.

The directions were excellent and easy to follow. An hour and one-half later, he found himself pulling up in front of Her house. The nervousness and the feverish excitement returned. He used the methods he employed to calm himself in court. He took a deep breath as he stepped out of the car. He put on his suit jacket and straightened his tie. Clasping his hands behind his back, to hide the slight tremor of nerves, he began to stride up to the door of her duplex. His hand shook as he pressed the doorbell. The thought of running ran through his mind a thousand times as he waited.

The door opened. She was standing there, her top open, just like in his favorite picture that she had e-mailed to him. She took his hand and pulled him into her apartment. She was wearing her pajama’s, with the top open, just like in his favorite picture. It was a picture that had filled his fantasies for several weeks. We’re really going to do this,” he said.

She was now before him, in the flesh. His eyes took in her ample curves. The round swelling of her stomach. The heavy breasts, hanging below her half open pajama tops. His eyes finally moved up to her face, a face that he never really seen in the pictures she had sent. The firm, full line of her red lips. Her curly brown hair, falling to her shoulders. He gazed into her lustful brown eyes. He said. “I am here to surrender myself to you, Debra.”

She reached out and caressed the wool of his fine suit jacket, the smooth silk of his tie. A wide grin parted her lips. She shrugged her pajama tops off of her shoulders, allowing them to slip to the floor. His looked away from her eyes, to the enormous, hanging breasts, the pale areola, and the erect nipples. He felt his own hardness pressing against his suit pants. She moved her hand slowly, lightly over his tie, until the finger tips brushed the swelling in his pants. Without warning, she grabbed hold of his staff, through the soft wool of his slacks. “You are ready to give yourself over to me completely?”

“Yes, Debra.”

“You will do as I say?”

“Yes, Debra.”

“As long as you are here, this belongs to me?” she asked, giving an extra squeeze.

Involuntarily, his hips thrust toward her.

“And you ass belongs to me?”

“Yes, Debra.”

“Get out of these fancy clothes, right now.”

He stared directly into her eyes, as he began to disrobe. He slipped off his grey jacket, and tossed it over a nearby chair. He loosened his tie, then snapped it off of his neck. Smiling and gazing at her face, he teased her nipples with the smooth silk of his tie before tossing it onto his jacket. He continued to stare into her eyes as he slowly unbuttoned his shirt, revealing the light curly hairs of his chest, the firm pectoral muscles. He pulled the shirt out of his trousers, slid it off of his arms, and tossed it onto the pile. He quickly forced his shoes off and kicked them aside. He undid his belt, snapped it off of his waste, and tossed it aside. He undid the button of his trousers. Then paused and smiled. He slowly lowered the zipper, revealing the white clothe of his briefs. He paused again. He saw that she was staring intently, waiting to see…. He lowered the trousers around his hips, let them fall to the floor and stepped out. He was standing before her in just his tight white briefs and his socks.

She could see the outline of his penis in the briefs and the tip pressing outward. “Should I remove these now?” he asked.

“Yes, get them off,” she responded, with more of a husky sound of urgency in her voice than the command that had been there before.

He bent over to remove his socks. “Not those. Remove your underwear.” He looked up, smiled, and slipped his fingers under the waistband of his briefs. He slowly began to slide them over his hips and off of his ass, deliberately leaving the front up. The fabric stretched over his organ, so that the shape of the tip and the ridge of the tube along the underside was clearly outline for her. He then began to pull down the fronts of his briefs, ever so slowly. The elastic caught around the tip, bending his very stiff penis down with his brief. The farther he pulled the briefs, the farther it pulled down his organ, until his erection was bent straight down, and the curly red pubic hairs were revealed. He pulled the briefs lower. The base of the shaft began to slide into view. Excruciatingly slowly, millimeter by millimeter, he lowered his briefs, revealing more and more of the shaft. All of the shaft was finally visible, the elastic hooked on the ledge of the tip. He pulled a bit farther, and the erection was released from its pressure, bobbing up and down until it came to rest, pointing upward, so that the tiny hole at the tip seemed to be staring at her face. He let the briefs slide to the floor and stepped out of them.

“This belongs to me, today, too,” she told him, reaching out and stroking the loose skin, up and down, feeling the stiffness of the shaft and the softness of the flesh. “Now, show me how you worship me.”

He lowered himself to his knees in front of her, slipped his hands into the waistband of her pajamas, and slid them over her hips, his hands lightly caressing her ample derriere and they slid past. He let them fall to the floor, leaned forward, and placed a kiss on her tummy. He looked up into her lustful eyes. He began to move his lips toward the center of her female power, which was already swollen and open.

“Not yet,” she stopped him, putting a hand to the top of his head. “Lets take a shower before we get down to business?” He stood, and she told him, “This way.” She led him to the bathroom, his erection bobbing and pointing at her bottom as he followed her.

After Debra got the temperature the way she liked it, she stepped into the shower, and he followed. She stood facing him, with her back under the flow of water from the showerhead. He took the soap, lathered his hands, and spread the suds over her chest and stomach. He gently turned her around, so that the water splashed on her front while he stretched his arms around her body from behind. His erection was pressed upward between them, burning hot against her back, as his hands reached under and cupped the weight of her breasts. The volume of her womanly flesh overflowed his hands as he gently lifted and squeezed them. He felt her press backward against his heat as his fingers circled her areola, as he pulled lightly on the nipples with his thumbs and forefingers. She turned back around toward him, and he dropped to his knees before the temple of her womanhood.

Again lathering his hands, he soaped her thighs, running his hands up along the insides, stopping just before he reached her open, throbbing sex. He reached around behind, his cheek pressed against her tummy, water now flowing from his face, as his hands soaped her derriere, squeezing, stroking and caressing her massive cheeks. As his hands caressed her buttocks, he gazed adoringly at the beauty of her open flower. Framed by neatly trimmed pubic hairs, he saw her swollen petal, spreading before him. Her tiny phallus poked its head from its sheath. He brought his mouth to the center of her power as a woman, pressed his lips gently onto the emerging tip of her jewel, and planted a gentle kiss, sucking softly. He felt her shudder, and thrust her hips toward him. He removed his mouth and stood, smiling.

His penis stood out, board stiff in front of him. She stared down at his erection. He was circumcised, his mushroom tip smooth and a deep purple form the blood that filled the organ. The rod pointed slightly upward. It was long, perhaps 7 1/2 inches. A collar of wrinkled flesh from the circumcision lay around the tip. She touched the tip with a finger, pressing downward. When she released, it immediately bounced upward. She giggled. Debra took the soap and lathered her hands. She reached out her left hand and gently cupped and lifted his balls. He closed his eyes, tipped his head back, and let out a low moan of pleasure. He felt her fingers close around his shaft. Her hand began slowly stroking. His body shivered as her fingers moved over the smooth sensitive tip.

Without warning, she stopped moving her hands “I think that’s enough for now,” she said in a hoarse voice. “We don’t want you to cum now. Remember what we’re here for.” She gave a last squeeze and released his manhood.

Grasping his hips, she guided him to turn around. She again lathered her hands, and washed his back, moving slowly down to his flat, white buttocks. He feld her hands moving around on the cheeks of his ass, lifting them apart with each circular movement. Then, there was a finger at his most private entrance. Small, circular motions around the rim of his anus, first. Then, the finger, pressing inward. His first reaction, involuntary, was to tighten and resist. He felt another hand gently caressing his balls, as the pressure of the finger increased. He willed himself to relax, and the finger slid in. There was no pain. It felt exquisite, as the soapy finger slowly moved up his tight rear channel, past the first knuckle, to the second knuckle. Hesitating for a moment. Pushing in deeply, until he could tell that the entire finger was buried inside of him. He pressed his hands against the wall of the shower to brace himself, opening his legs wide. He felt her finger begin to move in and out of him, slowly, getting him used to the invasion. He felt her curling her finger, exploring, rubbing against his prostate. The feeling was intense, exquisite, like nothing he had experienced before.

He felt the finger pulling out, and attempted to grab it and hold it in by tightening his asshole. To no avail. The finger withdrew. The finger again rimmed his anus. He felt a pressure again, against his back entrance. This time, he did not resist. He pushed his bunghole open, as if he was pushing out. Trying to open himself, to invite a return of that intense stimulation. But the finger did not slide in so easily this time. The pressure grew. There was a moment of pain, deep in his gut. He felt it pop in again. He felt a sliding in, smoothly, yet much more tightly. He realized there were two fingers, this time. They only invaded to the second knuckle. Again, she slid them in and out, probed, stimulating his prostate. He felt stretched, but he also felt deep pleasure. He leaned his forhead against the wall and moaned, surrendering. To soon, the fingers began to withdraw. He leaned, there, waiting, his knees trembling just a bit. He barely knew where he was. He was just surrender, pleasure, stimulation.

His reverie was broken by her voice. “Come on, lets get out of here. We have a lot more to do.” She grasped his still stiff manhood, and playfully pulled him to follow her out of the shower. She stepped out. He felt weak in the knees, and was slow to follow. He turned off the water, and exited the bathroom.

He found her, leaning back on her bed, heavy breasts hanging free, legs apart. “I need to cum,” she commanded in a soft but firm drawl.. “Get your face in here right now.” He crawled onto the bed, between her legs, and pressed his lips against her thigh, just above the knee.

He began to slowly lick up the inside of her leg, inching closer and closer to the center of her female nature. Her legs smelled clean and fresh from the shower, but as his mouth drew closer, he inhaled the odor of her arousal, the scent of a woman’s sex. His tongue moved to the top of her thigh, into the crease between her buttock and her leg, moving up and closer. He tasted her juices on his tongue. When his tongue was just about to reach her slit, he stopped, and started to slide his tongue back down her thigh. “God damnit,” she cried. “Enough playing around. I told you I wanted your mouth and tongue on my pussy, and I meant it.”

He looked up at her for a moment, smiled, and placed his mouth, full, wide-open, over her entire pussy. He exhaled warm air over her sex. Then he spread its pressed his tongue between her swollen, excited lips, and licked upwards, feeling her fluids flow over his face and beard. His tongue barely caressed the tip of her hard little knob in passing. He licked again between her hot pussy lips, pressing just a little harder and deeper. He repeated that upward, licking motion several more times, pressing deeper each time. Then, he made his tongue hard and narrow, and thrust it deep into her passage, pushing as far in as he could. He probed upward with it, seeking her G spot. He thrust his tongue deep into her, then pulled it out, fucking her with his tongue lock it was a small cock. With each outward movement, he let his tongue slide over her hard clit. He withdrew his tongue from the depths of her hot, moist channel, and placed the tip directly on the tip of her clit. Placing his hands under her ass, he pulled her toward his mouth, burying himself between her thighs. He began to run his tongue up and down on her clit, flicking at it. Pausing, occasionally, to put his lips over it and to suck it, before returning to the up and down flicking motion. He tried playing around her clit with circular motions of his tongue. Oh yes, she seemed to enjoy that. He felt her thighs grow tight around his ears. He started twirling his tongue around her clit, faster and faster, around and round, pulling her to him She lifted her hips toward him. Twirling his tongue, around and round Her hands on the back of his head, pulling him into her crotch. His tongue kept moving She screamed and bucked into his face, flooding him with womanly excretions. He continued to work his tongue on her clit until the tension passed, and she collapsed back onto the bed.

Debra sighed contentedly. She smiled and stared at the naked, older man, who was still lying on his stomach, between her legs (although his mouth was no longer pressed against her genitals). “Ok, dear, its time to get yourself ready for me. Get up on your knees and put these under you.” He lifted his hips, and positioned the pillows she gave him under his body so that his ass pointed upward.

He began to shiver. “Don’t worry, dear,” she assured him. “I don’t want to hurt you. I just want to own your ass.” She opened the jar of petroleum jelly that has been sitting on her night stand since they made the appointment. She dipped two fingers into the jar and scooped out a large glob of the greasy goop. The lubricant felt cool between the cheeks of his ass as she smeared it around the rim of his anus. She dipped into the jar a second time, and pressed her middle finger against the ring. It slid in easily this time. She slid the finger in and out, coating the inside of his passageway with the gel. The finger was removed, and then two coated fingers pressed against his hole. He pushed back, opening his hole, and the two fingers slid in. He let out a soft groan.

She stopped pushing. “That feels good,” he assured her in a slightly raspy voice.

She pushed her fingers in, wiggling them against his prostate, and then sliding them in and out. “Now, I have to stretch the opening.” She gently moved her fingers around the rim of his anus with just the first joint or each finger inside him. “How does that feel?”

“You are doing a wonderful job,” he gasped. “I think I’m ready for three fingers.”

She removed her fingers from the tight, warm passage. She dipped three fingers into the jar, and returned them to his hole. She pressed in. He pushed out. Nothing happened. “Push harder,” he panted. He felt the pressure increase. She put a hand under his stomach, which was bulging outward. She wriggled her fingertips at his opening, try to gently stretch it open. He pushed back harder. The three fingers started to slide in. He felt a cramping in his gut as his anus was stretched. He let out a guttural groan, and she stopped, releasing the pressure, and her fingers moved back out.

“No, that’s okay, keep going.” His voice came from so far back in his throat, she was not sure what he said. “Go ahead,” he gasped. “Stretch my asshole.” She resumed pushing, twisting her fingers slightly to move them forward. He pushed back and open. Her fingers started to move, slipping forward to the first joint of each finger. She heard him panting and gasping for breath.

“Are you okay?” she asked.

“Yes. Just let me rest a minute.” He lay their, catching his breath, with her fingers lodged in his asshole. Gradually, the cramping eased, replaced by an incredible feeling of fullness and stimulation. “Okay, open me more,” he said.

She began twisting her fingers around, back and forth in circles, stretching the opening. He let out little moans, occasionally, followed by, “That’s good,” or “okay.” After several minutes, she began to push the fingers deeper inside with the twisting movements. He let out a breathy, “aaahhh” as her fingers slid up to the second joint. There was still some pain, but the stimulation, the feeling of fullness, overwhelmed the discomfort with waves of pleasure. She wiggled her fingertips, caressing his prostate and sending a shock of excitement through him. Debra continued to turn and wiggle her fingers, while her left hand stroked his stomach, his balls, and then finally the stiffness of his organ.

His moans were becoming more regular. She leaned over him, with her hand still inside, and kissed his cheek. “Do you think you are ready?”

“Yes.” It came out in a strangled voice. The one word was all he answered. She slowly inched her fingers out of him. After the first knuckle had been passed, the tight ring began to squeeze her fingers as they slipped free. Vaseline dripped out of him, coating his testicles. She opened the drawer of her night stand.

She removed the dildo and harness from the drawer and set the harness on the table for a moment. The dildo was a soft, smooth plastic, bullet-shaped with a rounded tip, about 7 inches long from the groove the fit into the harness to the tip. Mike had ordered it for her and had it sent directly to her house. (She had been apprehensive about having it delivered, but Mike assured her that the packing would be unmarked. He said he would be embarrassed to carry it through airport security.)

Debra had been having fun with the toy since it arrived. She had adjusted the harness and strapped it on almost immediately. Standing naked in front of a mirror, she had admired the way she looked with a stiff phallus sticking out from her crotch. She had enjoyed stroking the smooth plastic the way a man would stroke his cock. When she did that, she discovered that the soft foam in the base of the dildo would gently massage her clit when the dildo moved. She had brought herself to an orgasm, stroking and moving “her cock” and feeling the base rub her clit. Now, however, she knew that she had to prepare the lawyer, so she put the harness aside.

She took a handful of Vaseline and coated the entire surface of the shaft. She showed him the plastic organ, and asked, “Are you ready for this.” He nodded and grunted. Using her hand, she gently pressed the tip against his puckered hole. As soon as the tip touched the pink little opening, he pushed it open. He reached back with both hands and spread his cheeks, making the opening stretch even wider. Although the tool was somewhat thicker than her three fingers, she found that it slid in much more easily. She did not have to push hard to get two, even three inches to sink inside. She watched in fascination as the plastic disappeared into his most private chamber. After three inches, she began to feel some resistance. She stopped and twisted it gently, circling inside him a little, before resuming the pressure. Slowly, the shaft slid into him. At four inches, he let out a long, low groan.

She hesitated, and he choked out, “Keep going.” Another inch. She would not be able to get it much deeper when she was wearing it. She slid it back an inch, then back in. Back and forth, sliding just a shade deeper each time. Each time she pushed it in, he let out a moan, softer each time.

Finally, with the shaft buried nearly six inches, she told him, “Its time for me to fuck you”

“Yes, woman, I’m ready. I’m ready for you to fuck my ass. Fuck me deep.” She slowly slid the dildo out of his ass. He watched her as she strapped the harness around her waist and under her round buttocks. She fitted the base of the dildo into the harness, and wiggled her hips. Debra added some more lube to the phallus, to “her cock”, and smeared some more on his anus. She positioned herself behind him, on her knees. She stared down at him, bent forward, open, exposed, surrendering himself totally to her.

She used her hand to position the tip of the plastic organ against his butthole. She waited like that a moment longer, enjoying the anticipation. Then she pushed her hips forward. There was only a moment of resistance, and he opened for her and she slid in easily. She firmly grasped his hips, and pushed her own hips forward, sliding into him, 3 inches, 4 inches, 5 inches. She looked down, and could see only a small piece of the plastic, connecting them. She pulled back, slowly, until only a couple of inches remained, then thrust forward, a little faster this time. He let out a groan. “Oh, yes.”

She felt the foam in the base rub against her clit as she pushed forward. Back, then sliding in again. This time, she felt him pushing back against her. Deeper. His ass pressed against her thighs. She was buried in him. “Fuck me,” he cried.

She began to move back and forth, in and out of him, still gently, but faster and more vigorously. “Oh, yes,” he shouted. She reached under him and placed a hand around the shaft of his cock. He responded by thrusting his hips back against her, flattening his ass against her thighs and impaling himself deeper. The fire in her clit began to build with each thrust into his ass. She began to stroke his cock while thrusting in and out of him. He pressed his ass against her, holding himself there. She stroked his cock frantically, and felt the wave run through it as he came. She pushed as deeply into him as she could go, the pressure on her clit releasing her own orgasm. She shuddered with pleasure as she felt his cock pulsing. He collapsed to the bed, and she fell on top of him, still impaled deep inside him.

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