Meeting a Guy From a Chat Site

Jenny threw off the covers. It was a hot summer morning and she was finding it difficult to enjoy her sleep-in. It was partly the heat - her cotton nightdress clung to her uncomfortably - but her mind could not settle, her brain was whirling and the subject of her thoughts was the pictures and stories she had download from one of her favorite chat sites the previous evening.

Jenny had been chatting with Phillip for several months now and they had progressively got into more and more explicit sexual fantasies. Phillip usually guided the discussion and often sent pictures and stories to make their mutual masturbation sessions more exciting. Now Jenny lay on her bed and thought back over yesterday evening. Phillip had "accidentally" sent her some very explicit "farm yard" movie clips and stories. She had been disgusted but also she had be strangely excited by the eagerness of the woman in the video to get the dog "tied" with his knot wedged deep in her pussy.

Now Jenny had woken with thoughts of her discussions with Phillip about group sex at a club he said he owned whirling round her head. She often got aroused like this after a hot session on the internet. But last night was different. She had allowed herself to get into some very graphic discussions about what had been taboo subjects for her. She had even had a very explicit open chat with Phillip and several others about doing some of these things for money. Jenny was now keyed up and worried that she had gone too far again by surrendering to her lust and wretched financial position. What worried her most was that she had invited Phillip to her home that afternoon to "audition" for work as a hostess and dancer at the special club he owned. She was also appalled that images from the dog video were a key part of her disturbed morning, a fragment of her jumbled thoughts that was proving very stimulating to her debauched mind.

Many men (and some women) had been her lovers since she surrendered her virginity to her uncle on her 14th birthday. In the past seven years she had become aware that she needed men with big cocks and lots of stamina to be really satisfied. In fact the best sex she had ever experienced was on the eve of her wedding when she ended having sex with the two Negro strippers her girlfriends had hired for her "shower" Their big black cocks were as thick as her wrist and she ended up fucking them both in front of all her friends.

Her desires for wilder more exciting sexual experiences were always leading her into trouble. Two months ago her husband had come home and caught her masturbating during one of her more wanton internet chat sessions. In the aftermath of the fight that followed he found her computer files and read all about her secret sex life. Now she was living alone in an isolated and run down house on the edge of town. Her husband had cleared out and left her destitute so she was struggling to live on the meager "dole" that the government provided to the unemployed.

Jenny's fingers and fist knew every nook and cranny of her pussy from a lifetime of masturbation. Now as she lay on top of her bed enjoying the morning sun streaming through her open bedroom windows, visions from the chat with Phillip triggering the familiar tingle between her legs. Her hand slid down over her belly and gently cupped her sex through the opening in her nightgown.

She felt guilt-ridden - fancy getting horny over thoughts of sex in front of strangers and watching dogs do it with other women! "You've been too long without a good fuck, my girl!" she thought to herself. Then she parted her legs slightly and slid her hand between her thighs. She pressed her finger against her pussy and felt her swollen clit through the thin material of her nightdress. Dreamily she pulled the hem of her nightie up around her waist. Her hand slid between her thighs and, as she had done so many times before, she drew up her knees, let her legs fall apart and began to caress herself. She ran her finger slowly between her legs, starting at her puckering anus, then moving to the entrance of her vagina and bringing it slowly, teasingly along her large protruding pussy lips to her clitoris, savoring the feeling as she parted her puffy labia. A small, delicious shock of pleasure pulsed through her body as her fingertip brushed against the swelling nub of flesh that projected from top of her slot like a small cock.

Now she expertly moved her finger to retrace the familiar route, dipping ever so slightly into the entrance of her sex. She was skilled at this, making the sensations last, savoring every second. She pulled at her nightdress with her free hand, maneuvering it off over her head, changing hands momentarily as she slipped her arms from the sleeves so as not to disturb the slow rhythm she had begun.

The wardrobe at the bottom of the bed had a full-length mirror for a door and through half closed eyes Jenny enjoyed watching her 6' frame as she began to masturbate. All the time she was thinking how exciting it would be to do this in front of a group of strangers. She was propped up slightly on her pillows and her substantial breasts were swaying in time with the movements of her hand. They were not the firm, pert breasts of most women her age. Rather Jenny's large DD tits were soft and droopy. "Spaniels ears!" she muttered. Her large nipples were never less than semi-erect and were nearly always visible through her clothes. Now she continued to stroke herself and watched her nipples till they were standing proud and stiff like large acorns.

In this half lying position her belly was flat - she had a little "pot" when she was standing and her hips were on the large side. Child bearing hips were how her Uncle described them. She had long legs with solid, muscular thighs from her regular sessions on her rowing machine. Her pussy had a very light covering of wispy blonde hair that did nothing to hide her large protruding pussy lips. Jenny's finger dipped a little further into her wide-open vagina with every stroke. She felt the moistness down there growing and gave a small moan of pleasure. She closed her eyes and an image that Phillip sent her came into her mind. She saw a Great Dane, his substantial prick jutting stiff and proud. In her mind's eye she saw the chubby German looking woman on her hands and knees about to take its hardness between her pussy lips. She focused on how it must feel to be impaled by such a colossal canine cock. How it would stretch her pussy - her hand moved faster between her legs, her four fingers were slipping inside her gleaming pussy lips. Deeper she pushed past her knuckles. Soon she would be enjoying the pleasure she always got from fisting herself. She loved watching how her hand slipped easily into her virgina. How her pink fleshy labia moved with her hand and how quickly her copious juices flowed from her tingling hole. Within minutes she began to feel her first climax building. She loved this moment, watching how her body began to respond.

Jenny's heard a noise and her eyes flew from watching her image in the mirror... her legs snapped shut instinctively, her hand momentarily trapped deep in her soaking pussy. There, looking through her window stood a man! Who was he? How long had he been there? It didn't matter - he couldn't have failed to see her playing with herself. She quickly threw her dressing gown on in an attempt to cover her nude body. Then she realized she had seen his face before, it was Phillip! She tried to compose herself as she asked him to come round to the back door of her house.

Phillip instincts told him that this was his best find yet. He had developed a very lucrative business that was based in an up-market tabletop dance club. A specialized aspect of the business was arranging sex shows and parties for wealthy clients. He often used the internet to advertise for talent and after many false trails it seemed he had hit pay dirt again. He had learnt from many other contacts that arriving early enabled him time to check out things. More than once sneaking around had led to him discovering that a meeting was a "set up" This time was different, as he sneaked around the isolated house he found an open window and when he peeped in, there was this sexy young woman stark naked, with her hand buried deep into her almost bald pussy. The sight of her large breasts and the thrilling glimpses of her fisting her wide-open snatch captivated Phillip. She was almost perfect, short blond hair, very tall, big framed and that "homey germanic" sort of look that his clients loved. His prick had become rock hard as he watched her masturbate and he lost track of how long he stood silently watching and lusting. Then as she appeared to be nearing an organism he decided it was time to announce his presence. He tapped loudly on the window frame and was pleased at the reaction it created – first there was a loud sigh, followed by a frantic, almost comical flurry of movement as she tried to get her fist out of her pussy and put on her dressing gown at the same time.

Looking back afterwards, Jenny was amazed at herself when she recollected what she had done next. She stood beside the bed and beckoned Phillip to come into her kitchen. As he walked in the first thing she noticed was that he had a huge erection. She let out an audible gasp as her eyes locked onto the bulging outline in his loose cotton trousers. Then without warning slammed a wad of notes on the table and then pulled his trousers down in one swift movement that revealed his stiff cock in all its glory. He was hung like a prize bull and it was so hard!! Jenny let out an even louder gasp! The skin was stretched so tight that the veins stood out along its length and his balls were huge. She couldn't help herself – she was as horny as hell from her near orgasim that he had interrupted only moments earlier – she just stood there open-mouthed staring. Phillip interrupted her thoughts. "Well Jenny, that's the $250 audition fee so lets see how good you really are!" She moved trance like and kneeled in front of Phillip. Taking the end of his cock into her mouth she began to move her head up and down, caressing the swollen glans with her tongue. Phillip grinned, his efforts over the past two months of almost daily "chat sessions" with this young lustful woman were beginning to be rewarded.

Occasionally Jenny paused to savior his huge balls, sucking them one at a time into her mouth and then pulling back so they popped from between her lips. After several minutes of this eager sucking Phillip began to feel the sensation he had experienced many times before. "Oh shit! I'm going to cum!" Jenny removed his cock from her mouth just long enough to gasp, "Let it come, Phil!" before taking him back between her lips, her head bobbing faster and faster. Phillip's hips thrust and jerked as he felt his spunk pumping out into her mouth. Jenny swallowed greedily as she felt the man's prick pumping. She had almost a third of his shaft stuffing her mouth and she eagerly swallowed down the thick creamy cum.

Eventually she released his slackening cock and allowed him to lift her up into a passionate embrace. After a long deep kiss she pulled back and looked into his face "Please Phillip,... come into my bedroom, I need a good hard fucking" Phillip followed her to her room and soon she had pulled his head to her ample breasts. "Suck them, Phillip. Suck Jenny's titties for her. Phillip took the rubbery teat between his lips and sucked. He was jubilant to find the already large and erect nipple growing even harder as he suckled her acorn sized nipples. Big erect nipples was another thing his clients liked to see. His new slut began to moan softly. She reached down and took Phillip's cock in her hand and began to fondle him again. It felt so good to have a big virile prick in her hands again – even if Phillip was a lot older than he had told her during their frequent sessions on the internet.

Phillip moved down Jenny's body and found himself staring in admiration at her pussy. He had never seen such a perfect sight before. Jenny had reached down and spread her big fleshy pussy lips. He had rarely seen lips as big or a pussy that opened so wide, so easily. And the best part was her clit, it stood up proud like a small cock. He touched it with his fingertip causing her to shudder and in the process she pulled her pussy lips harder. Phillip was awe struck! Her pussy was huge and he could see deep into its bright pink depths. She was dripping and her juices we oozing out and down over her asshole. She spoke in a hoarse whisper. "My clitoris loves being sucked and nibbled and I want you to lick it and suck it just like I did to your cock" Phillip needed no second bidding. He was soon lapping at the woman's cunt like an expert. Jenny lay back and delighted in the sensations Phillip's tongue was providing. How perverted! Sucking off a man she had never met before, then getting him to suck her tits and lick her pussy! The thought of the "naughtiness" of it all just made it all the more thrilling. She was becoming desperate to feel something more substantial inside her. "Put your fingers in me Phillip. Hurry, finger fuck me!"

Phillips mind was reeling with lust as he licked a finger and thrust it into her puckering brown hole. Jenny jerked as she felt the man's stubby index finger force itself up into her bottom. Then as she began to relax, she felt a thrill radiate through her body from the coarse actions of his finger wriggling deeper into her tingling ass.

No! Don't stop! Use your other hand and put a couple of fingers up my pussy... There!... OH YES!"

Phillip had sat back slightly, raising his head to look what he was doing. He was amazed at how easily his fingers slipped inside her pussy - his initial invasion of her ass had needed the usual amount of force but this was remarkable. He looked at her pussy and watched as the puffy, protruding lips moved with his fingers - his new slut was thrusting her hips up to meet his hand, grinding her pubis against his palm. Phillip saw her take her breasts in her hands and pull at the erect teats, her head was thrashing from side to side. She opened her eyes and looked at him with a hunger that he had not seen in many women. His cock was hard again! Standing up resembling a flagpole, the purple head bigger than he could remember seeing it before and he could see lots of pre cum oozing from the large hole at its tip.

"Fuck me Phillip! Fuck me now - quickly!!"

Phillip knew exactly what this young woman wanted. He moved forward. Jenny took his donkey dick in her hand and guided him into her. Phillip began to thrust at once - hastily, wildly. Jenny felt his cock plunge deep into her, filling her more than she had been for many months, his big balls slapping against her buttocks, she felt her new lover's prick begin to piston in and out of her pussy, stretching and filling her. She was on the verge of coming. She reached down between their bodies and began to tweak her hard clit, her hips were rising to meet each virile thrust of this 48 year old stud.

"Harder!... Fuck me harder!!... Ooooh yes!!.. yes!.. Now!!!" Phillip was surprised how forcefully her hips jerked and bucked as she came. He felt her vagina grip his huge tool and, for the second time in fifteen minutes, he felt the sensation that meant his balls would soon be emptying another load into his horny young woman.

Later as she laid back enjoying the sensation of the sperm seeping out of her and dribbling down over the puckered ring of her anus. She remembered the thrill she had felt when he had thrust his finger there and the enjoyment she always got from having a good hard cock in her ass. Anal sex was something that she had gradually grown to love since her first unpleasant experiment when her uncle fucked her ass twice on her 15th birthday. Now it always excited her, especially taking a thick, fully grown cock all the way up her ass. Now it was almost an essential "desert" to normal sex that she frequently craved. It always made her feel so marvelously wicked. She loved men who were comfortable with licking and fucking her in that way but it was something that she had rarely had enjoyed in recent months.

It just happened that Jenny had discovered early in her sex life that she had an unusually sensitive, itchy asshole. Whenever her cunt got wet, her asshole usually felt hot and tingly too. It had been a long, long time since she'd felt a really big prick boring into her ass and now she wondered if she would be able to accommodate Phillip if he tried to shove his huge cock up her ass. She was suddenly frightened by the thought of such a big cock prying open her sphincter. Her puckered, brown hole began throbbing lewdly as she contemplated becoming a total anal slut with such a huge cock.

Taking a deep breath Jenny moved unsteadily to her knees, driven by her memories of how much she had enjoyed it in the past and the dark desired that lived deep in he psyche. "Phillip do you know where I'd like you to shove this big cock of yours next?...

"Up my tight ass!"

Phillip grinned as his cock rapidly hardened. Jennys eyes widen with a heady cocktail of lust and fear. She gulped, what was she doing!? She was scared of her ass being torn apart by his monster cock, and disgusted at her eagerness to ignore this obvious risk and have him fuck her ass. At the same time she was extremely excited that she was about to have a torrid session doing one of the "nasty" things that were frequently a feature of her sexual fantasies. So she shamelessly gripped her rounded white ass globes and spread them wide to revealing her brown, puckering orifice to Phillip. He grinned, as he moving behind her and delighted in the way she whimpered as he started licking and fingering her back door. "Stick your fingers in Phillip. Get my bottom nice and ready for that huge cock of yours. "

Phillip did as his new slut asked, straightening his fingers, thrusting first one, then two into the gripping interior of her bowels. Jenny groaned, fucking her itchy asshole onto his fingers... "mmmmm that's so nice" she moaned. Soon his fingers were sliding in and out of her ass igniting that delicious tingling she craved.

Phillip aimed his swollen cock tip at her saliva coated shit hole. The rubbery rosebud stretched and slowly opened to admit the head of his 11" cock. He paused for a few moments, enjoying the sight of Jenny squirming as she attempted to welcome him into her body. It had been so, so long since her last asshole reaming with a massive cock. Her asshole was already spasming in response to the invasion of his huge cock. As he felt her begin to relax, Phillip reached round and grabbed her swaying tits. Jenny moaned with pleasure and she forced herself to start humping, wiggling at the same time, trying to help her hung stud to stuff another inch or two of his fuck pole into her blazing, gripping ass. Jenny loved this moment, the almost unbearable pain, pain that would soon be transformed to the most lurid sexual satisfaction.

Then there was intense searing pain! Phillip had pulled hard on her tits and thrust forward. She felt the cock cleaving into her bowels, instantly stretching her tingling asshole around the invading thickness of his prick. Jenny screamed "FUCK!... your tearing me apart" The hot brutal pain radiated from her asshole as she bit down on he lip, trying to stop herself whimpering as Phillip's balls slapped home against her pussy lips. He paused, his cock was buried deep in her tormented ass. His huge prick pulsating as it soaked in the indescribable clenching slickness of her shit tunnel. Gently he moved his hands down her belly and started caressing her swollen clitty and sluicing his fingers into her sloppy pussy.

Jenny was moaning and sobbing. But despite the pain she began to shamelessly push her stretched and tingling asshole back onto his cock. Phillip grunted as he heaved behind her, trying to force his immense cock deeper into the heat of her asshole. Then putting his hands on the twin globes of her ass, he pulled out slowly till the knob of his shit-streaked pole was almost out of her tortured hole. Then after what seemed like minutes he rammed his prick back deep into her bowels. Soon he had settled into a deep, hard rhythm, slowly out then slamming his prick back in to her horny ass. Jenny's sobs receded and she began to pant "Oh god I need this, Phillip! Deeper, baby, really push it in now! Oh, fuck, oh, shit, fuck my asshole as deep as you can!" She was pleading now. "Fuck my asshole, fuck my horny asshole!"