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Caught in the Web

Category: Anal Sex
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Frank rang the doorbell at exactly 8 PM. He was not a man that was late or unprepared for nearly any situation and pushing that bell was the culmination of two months of planning and preparation. While he waited for an answer his mind allowed a few extraneous bits of doubt to surface. Was there anything that he had overlooked? He was sure of himself, how about her? He was about to confront a woman he had never seen before but felt he knew intimately.

They had never met in person before. All their communication had been by Internet and telephone. Frank was cruising through sexual cyberspace one night in search of a deeply meaningful and mutually satisfying relationship with a horny girl, for the next ten minutes. He had done that several times before, found a hot chic, chatted for a few minutes about wild, unimaginably torrid sex, then evaporated into the ether. Sometimes he was relieved of sexual tension, sometimes not. The girls always achieved total and complete satisfaction…at least every one always said so, and they had, after all, put it in writing!

One night he started chatting with a girl who seemed much more relaxed and upbeat than the ones he had run into before. He could detect not the slightest hint of inhibition, she was articulate about what she liked, and the more he chatted with her the more he became aware that he had found a kindred soul. She was a very special lady.

After a session lasting considerably longer than usual, they began corresponding by e-mail and revealing the desires and needs each usually kept well buried by strong super egos. Before too many days they had exchanged phone numbers and each was able to hear the other say, out loud, what they wanted to do to and for each other.

Now, as he stood waiting for her to answer the door, his heart beat faster and faster in anticipation of a truly wonderful experience.

The door opened and there before him was an extremely attractive woman in a maroon turtleneck, black pants, a fine gold chain around her neck, diamond earrings, short, curly blonde hair, and eyes that sparkled so much they might be on fire. The first thought that raced through his mind was that what he had heard about love at first sight was absolutely true. He was enthralled with her beauty. She smiled and his heart pounded and he could feel an adrenaline rush course through his body.

“Hi Jo, I’m Frank. It’s wonderful to see you at last.”

“Hello, Frank!” she said, and opened her arms. They quickly embraced, he brought his head back so he could see her face and kissed her warmly, his tongue caressing hers. He had one hand on her back and with the other ran his fingers through her hair and pressed her head as close to him as he could. They hugged and kissed each other as passionately as though they had been lovers reunited after a long absence rather than two people who had just met.

“Wow,” said Frank. “This is wonderful. This is beyond my wildest dreams. Oh, God, I never expected this!”

Jo smiled and gave him quick hug and kiss on the cheek. “Would you like a drink? Some wine?”

“I’d love some.”

He followed her through the house to the kitchen where she got a bottle of wine out of the pantry. She handed him an opener while she got two glasses from a cabinet.

He filled the two glasses, handed one to her and raised his glass to her in a toast, “Here’s to a wonderful evening.”

“Let me show you around” she said, leading the way to a doorway leading to the basement. “I have turned the basement into a playroom and this is one of the first times I’ve had a chance to use it properly”. They walked down a flight of stairs into a fairly large room with a low ceiling, thick carpet, and a fireplace. There was a low coffee table and leather couch in front of the fireplace, a gas log was blazing brightly making the room warm and cozy. There was a pair of chairs around a small table next to the wall, and no other furniture.

“I thought we could start down here, then later, if we want, we can go back upstairs. I’d like to run up and change. It will only take me a minute. If you want to freshen up there is a bathroom at the other end.” She turned and went up the stairs.

Frank looked around a bit, and went into the bathroom for a few moments.

It was only a few minutes later when Jo reappeared in the basement. She was wearing a loose fitting black robe.

“That didn’t take long,” said Frank.

“I couldn’t wait. Are you ready?”


Once again they embraced, holding each other close, their tongues exploring each other’s mouth. Frank ran his hands up and down Jo’s back, pulling her close, and communicating his intense desire by pressing his thigh tightly between her legs. As he kissed her he let his hand brush lightly across her breast as he loosened the sash holding her robe closed. The robe came open, she was wearing a leather harness and a small leather thong. Between her gorgeous breasts was chrome-plated ring to which the leather straps attached. Her breasts were perfectly formed, firm, and her nipples were just beginning to be erect.

“What do you think?” she asked.

“You are absolutely stunning, my dear” he said softly.

They embraced once more, then Jo began to unbutton his shirt while he unbuttoned his cuffs and unbuckled his belt. She pulled his shirt off his shoulders and held his arms, still in the shirtsleeves, behind his back. She nibbled lightly on his nipple. Her tongue flicked across the tip of his nipple and she held it oh so gently in her teeth. He inhaled sharply, every moment of this new relationship was providing him with new pleasures. Her mouth lingered momentarily on his nipple then she pulled his shirt off his arms and flung the shirt aside. She kneeled in front of him and began to undo his pants, holding her face against his stomach. She ran her tongue over and in his navel. While trying to burrow her tongue into his navel she pulled his pants down. He was wearing string bikini briefs, and it was obvious he was greatly excited. His cock was beginning to stretch the briefs as it stiffened to her touch.

She ran her tongue over the tip of his penis, wetting his briefs. She took his growing shaft between her teeth and moved her lower jaw from side to side, massaging it while turning her head from side to side. His cock began to throb with excitement. Her hands were behind him pulling his body towards her face, she slipped her fingers under the thin strings of the briefs and pulled them down. His fully erect cock sprang from confinement and she immediately took it in her mouth.

Her tongue flickered around the tip and little by little she took more and more or it into her mouth until after a brief moment she was taking all of it down her throat. The tip of his cock was cushioned at one moment on her lips, the next moment it was touching the back of her throat. When it touched the back of her throat he could feel his anus contract and his cock throb. She continued to provide this most exquisite oral service until it seemed he would no longer be able to contain his orgasm. He could feel his load bulging within when she tapered off and brought him to a less feverish pitch.

“We have to get you dressed up too” she said and got up. Taking him by the hand, she led him over to the coffee table and opened a small drawer in it. She took out a leather cock ring. She fastened a wide leather band around his scrotal sac at the base of his shaft. It was tight and she had difficulty getting the snaps closed. Once it was in place she took a thin leather strap and snapped it from one side of the first strap to the other. The thin strap separated his balls and again was very tight. Finally, there was a third strap that she fastened around the base of his cock, as tight as she could get it. Now that his cock was tightly harnessed it stood erect as never before, and she once more took it in her mouth and to the back of her throat.

“I love your cock all harnessed up like this,” she said. He pulled her to her feet and kissed her, holding his very erect cock between her legs, and ran a hand over her breast, pinching a nipple gently. He took both breasts in his hands and pinched both nipples, then knelt and pushed her breasts together so the nipples were almost next to each other and began to run his tongue over them. He lingered over these perfect breasts, gently nibbling on her nipples and when they began to be hard and erect the pursed his lips around them and bit them using his lips as a pad between her nipples and his teeth.

Now it was his turn to let his tongue roam over her navel. She had an exquisite gold bar piercing the outer edges of her navel. He ran his tongue over the ball on one end, on the other end was a minutely detailed rose. He thought what a perfect design for someone as lovely as Jo.

While he flicked his tongue over her navel rose he grasped the back of her thighs and ran his hands up and down her legs, eventually letting his fingers slip under the sides of her thong. He turned his head to the side and pressed his head hard against her stomach. With the thong straps between his first two fingers on each hand he raised his hands and brought her thong higher, make it tight between her legs and cheeks. With his face hard against her crotch and the thong cutting deeply into her he could smell her excitement and see the beginning of moisture seeping from underneath the thong.

He could wait no longer. He pulled the sides of the thong down revealing a closely cropped, heart shaped tuft of hair around her moist pussy. It took him only a fraction of a second to bury his face between her legs and spread her lips so he could get his tongue between them.

He stood up, gently walked her back to the couch and lowered her to the couch. He knelt before her and, with her buttocks on the edge of the couch and with her legs spread wide he parted her pussy lips with his fingers and let his tongue play across her clit. Her pleasure was palpable, and before too many moments she was moving her hips to meet his probing tongue. She grasped her breasts and ran her fingers over her nipples while his tongue brought forth more and more wetness.

She was close to orgasm. He buried his face and tongue as deeply into her as he could, he now had two fingers in her pussy and was finger fucking her faster and faster. She began to moan. Her pussy kept getting wetter and wetter. As she began to cum her body went rigid and she thrust her hips towards him. She pinched her nipples as a wave of ecstasy flowed over her body. They remained locked together for the duration of her orgasm, when she relaxed a bit he picked her up and lay her gently on the floor.

Immediately he turned so his cock was presented to her mouth and his face was once more buried between her legs. They each grabbed each other’s butts, pulling themselves as close to each other as possible. His cock had never been harder, more erect, nor in greater throes of passion. She gushed wetness as never before. The moment they were locked in a 69 embrace she was well on her way to more orgasms.

Almost simultaneously each slid a finger between the others cheeks, finding their tight asses and sticking the tip of their fingers inside. They rolled from side to side on the floor, working their fingers deeper into the other’s ass. Each time Jo tried to push her finger into Frank’s ass his asshole contracted and his cock throbbed. When he stuck his finger deeper into her ass she moaned in excitement, her breath coming in short fast pants.

They lay locked together on the floor, their faces in each other’s crotch, bounding across wave after exquisite wave of fiery passion. They held each other tightly, rocking from side to side then rolling over and over, first one on top, then the other. When Frank was on top he used the weight of his hips to force his cock deeply into Jo’s mouth, so deeply the leather ring around the base of his cock pressed hard into her lips. With his arms around her body, one finger probing deeper and deeper into her tight ass, Frank pulled her body down, towards his face, forcing her ever so wet pussy closer and closer to him.

By now their fingers were darting in and out of each other’s asses and each entry produced a spasm of pleasure. Frank stuck his tongue as far into Jo’s pussy as he could and hugged her tightly, his legs and body rigid, his finger deep into her ass, his cock pulsating in her mouth. He held her for a few moments, then relaxed and turned to face her. They embraced, kissed, and caught their breath.

He helped her into a kneeling position; she put her head on the floor and raised her ass as high as she could. Frank retrieved a small chain from the coffee table and placed it next to them. Then he began to run his tongue over and into her pussy, then spreading her wetness up to her ass. His saliva was flowing and he pushed the tip of his tongue into her tight ass. While his tongue probed her ass he put the tips of his thumbs on the edge and slowly began to press against the resistance. Little by little he forced his thumbs into her ass, first one, then allowing her to relax a moment, then both. With both thumbs in her ass he knelt behind her and probed with the tip of his hard cock until it found her wet pussy. She rotated her hips so her pussy was easily assessable to his throbbing cock. Slowly at first, then more rapidly he began to thrust his cock into her, fucking her faster and harder. The harder and faster he fucked her wet pussy the wider he spread her ass. He thrust his cock as far into her pussy as he could and with a slight additional push he could feel her cervix with the tip of his cock. Jo moaned with pleasure at the sensation.

He pulled his cock out of her pussy and grasped the shaft and rubbed it across Jo’s wet ass. Slowly and deliberately he put the tip of his cock into her ass. He entered her with only the tip several times, allowing her time to relax and get used to having a cock in her ass. Little by little he slid his cock into her ass, as far as it would go. When it was completely inside her he stopped and waited. He could feel her fast shallow breathing slow as she began to relax. She took a deep breath. His cock was completely inside her now. While pushing hard against her to keep his cock in place, he hugged her waist, then caressed her breasts and nibbled on her ear lobe. His cock throbbed deep in her ass.

Frank retrieved the small chain with a snap hook on each end. He snapped one end to a small ring on the leather strap on his cock ring that separated his balls. On the other end of the chain was a double snap ring, one end of which he fastened to the harness ring between Jo’s breasts and the other end he fastened to a link in the chain so as to eliminate any slack. With his cock in her ass and his balls firmly attached to the ring in her harness, whenever he pulled his cock away from her ass the chain pulled on his balls, sending a wave of excruciating pleasure through his body. The chain was tight enough so that it was buried between her pussy lips and could rub across her clit.

The tension on his balls seemed to make his cock even harder. When he pulled his cock back so that the tip was almost out of her hole the chain pulled on Jo’s leather harness down in front. Frank hooked his finger in the ring on her back and when he quickly thrust his cock back into Jo, he simultaneously pulled hard on the ring. The tension on the ring was translated across her shoulders, through the harness and chain to his balls. He developed a rhythm of fucking her ass and pulling on the ring in her harness. He began fucking her faster and faster, his cock felt as though it were about to explode. She could feel his thick cock pounding her ass and the fullness of it made her gasp. The chain began to rub across her clit, sending throbbing waves of pleasure through to her very soul.

He paused in his pounding long enough to get a dildo from the drawer in the coffee table and handed it to Jo. She pushed the chain to one side and shoved the dildo deep into her pussy. He could feel the dildo against his cock. She moved it from side to side, rubbing it across the tip of his cock. She massaged his cock for a few minutes then shoved the dildo completely into her pussy. She arranged the chain so that it was across the end of the dildo and increased the tension by a couple of more links. Now each thrust of his cock in her ass provided an ultimate in pleasure; each time he pulled his cock out of her ass the tightening of the chain pushed the dildo deeper into her pussy, raked across her clit, and stretched his balls almost to the point of pain. He began to fuck her ass harder and harder, the tension on his balls and feeling the dildo on the tip of his cock sent him to heights of ecstasy he had never imagined before.

The dildo in her pussy and the chain rubbing on her clit sent Jo skyward too. Her body began to throb as orgasm after orgasm rolled through her body, coursing from her ass, through her pussy to the tips of her nipples. She came and came and came, she was on fire with pleasure, and wished it could last forever.

The pressure of such intense pleasure began to roil up from deep inside Frank. He was ready to cum! He reached in front of Jo and quickly unhooked the chain from her harness, pulled his cock out of her ass, and rolled her over on her back. He poised his cock above her face and began jacking himself off as hard as he could. Within a few seconds he began to cum, a huge wad of cum shot across Jo’s face. She opened her mouth so successive spasms could land inside, then she took Frank’s cock in her mouth and sucked every last drop of cum from it.

Frank fell, exhausted, on the floor next to her. It was a long time before he was able to move or speak. Finally, they looked into each other’s eyes and smiled. Jo rolled over next to him and put her head on his chest. He put his arm around her and gave her a very loving hug. He gently ran the back of his finger over her cheek and pressed his fingertip on her lips. She kissed his finger and snuggled closer. Both were satisfied that they had, indeed, met a kindred soul.

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