Funnel

Thomas was addicted to masturbation. He had been playing with himself since he was old enough to get boners and enjoy the stroking that accompanied it. He was a shy young man and especially so around women. He had been raised under the strict female ordinances of a domineering mother, and at 30 years old, he delivered newspapers. It had been his mother's idea that he keep to low earning jobs and leave the higher paying jobs for women. As embarrassing as it was, she had explained to him that men, after all, were best suited for "low work", as she put it. She was divorced.

Two doors down on Sunnyvale Road lived Audrey Green. Audrey was a fairly typical suburban housewife and mother. She worked at home keeping house now that she had sent her children off to make their way in the world. She was an attractive woman of 46 and had the body that comes with womanly maturity, and she was quite attractive to Thomas who delivered her newspaper each day.

These two lived their lives apart and with predictable regularity, only coming in contact when Thomas brought Audrey her afternoon paper. That is, until the fateful day that Ms. Fortune came to town.

Isabella Fortune was a statuesque beauty of 47 who stood about six feet tall in her stockinged feet. She was a brunette bombshell who epitomized everything sexy about older European women. She smoked her long European cigarettes, held precariously on the end of her finely expensive holder, her gloved hands caressing the end like a boy caressing his penis. She wore tailored business suits with modest hems that fit snugly. She was never without her pretty gloves and hats and she walked with a slight wiggle that sent her big ass (and a number of cocks) wagging. She moved in to the house between Thomas and Audrey and quickly became comfortable in her surroundings.

It was a Sunday when Thomas came home from the bookstore with his purchases to find his mother chatting in the living room with Ms. Fortune. They paused in their conversation to regard him in the doorway, his dark black sack of porn clutched to his tummy. His breathing was funny and, although he was pretty sure they had no idea what his bag concealed, he wanted to quickly go upstairs to his room and avoid scrutiny. Instead, his mother waived him over to them.

"Thomas, come here. I want to introduce you to our neighbor."

He shuffled over nervously and cautiously brought his black bag around behind him, clutching it just a bit tighter then necessary. His mother gestured toward the mysterious Italian woman sitting next to her on the sofa. He stole a crafty glance downward to her legs, wrapped in luscious, smoky black hose.

"Isabella, this is Thomas. My son. Thomas, this is Ms. Fortune."

He forced a crooked smile as the woman brought a white-gloved hand forward in greeting. He gently put his hand into it as she took it and he was a bit surprised by the grip he found there. The feeling of her soft-gloved hand was quite nice, but she didn't seem to be eager to let go. Her perfume drilled into his senses as her dark brown eyes looked directly into his own green ones. Her voice had an almost catlike purr when she spoke.

"Your Mama tells me you are a paperboy, yes?"

He swallowed hard and, unable to speak just yet, nodded in the affirmative.

"Is very nice. You deliver papers like the little boys. You deliver my paper too, yes?"

Thomas was getting increasingly uncomfortable standing there. He was all too aware of his dirty porno stuffed into the bag in his left hand. It was feeling so heavy all of the sudden. He wanted to get out of there! I mean, this woman was breathtaking and wasn't letting go of his hand and his mother was right there! And the way she spoke to him made him feel too excited.

"He is a bashful boy, no? You be my paperboy too?" She was gripping his hand tighter in her silky gloved fist and then her eyes fell down to the black bag in his white knuckles. "What is in his bag, here?"

His face was ablaze in embarrassment. My god! How was he going to get out of this? His mother was sitting right there and this woman was actually pointing… pointing to his masturbation toys! His mother actually saved him.

"Oh, he's always buying comic books and things like that. Did you spend all your newspaper money on that garbage again, Thomas?"

He nodded stupidly as he looked straight ahead, too embarrassed to meet the eyes of any woman right then.

Isabella let go of his hand, letting it slide through the little "O" she made with her fingers. "Can we see them, Thomas?"

He panicked. "Uh, I, uh… really have to get going. It was nice meeting you." He darted up the stairs to his room and quickly shut the door behind him. He leaned against it, trying to catch his breath. He pressed his ear against the door and tried to listen to what they were saying. But there wasn't much talking at the moment, just feminine laughter.

Thomas didn't know what they were laughing about and at that moment he didn't really care. He was safe in his room and his cock was making a tent in his pants. He needed to jack off bad. Raising the bag above his little bed, he dumped the contents of his shame on the mattress. He quickly stripped down to just his socks and stood there with a big boner, staring down at the toys he had bought. There were magazines of course, and a big tube of jackoff lube that the cute female clerk had gigglingly recommended to him. There was also a new masturbation toy that she had talked him into. He had blushed as Dawn had taken his finger and pushed it into the little opening of the device, which had come alive with a sucking action.

These toys were in front of him, but his mind was now actually on Ms. Isabella Fortune. He had never met a woman so mysterious and so exciting. He remembered the way her gloved fist had squeezed into a little knot as his hand slid through the material and there in his room his untouched cock gave a wicked throb. He winced a little at the sensation and then reached down for the tube of lubricant. He poured a generous amount over his cockhead and shaft and then reached down to take himself in hand. As he stood there naked but for socks, jacking off, he allowed his mind to recall the details of her outfit. There was something very sexy about the kind of stockings she was wearing. They seemed unusually shiny and tight on her muscular legs. He remembered them making a silky hissing sound when she crossed her leg and his balls trembled against the sticky slapping sound of his downstrokes. It was at that precise moment that a knock came to his door.

"Thomas. Are you decent? Ms. Fortune has to go and wanted to say goodbye to you."

Horrified, he froze in mid stroke. He couldn't seem to move at all. In the ensuing silence that followed, he gingerly took his hand off his throbbing penis and turned his nakedness to face the door.

"Thomas? What's going on in there?"

There was no lock on his door. His mother thought boys got up to enough mischief without the encouragement of privacy. He watched the doorknob turn.

"I'm changing clothes mom!", he cried out frantically.

There was an excruciating pause, during which his still hard cock painfully lurched, untouched in mid-air.

"Aww. He is a bashful boy, no? Goodbye, Thomas. Have a good afternoon."

He swore he could hear the teasing, zipping sound of her stockings rubbing together even through his door as she descending the steps to the living room. His cock lurched again and a dollop of precum slithered out of his opening and down the knots and veins of his shaft to soak into his balls. Then, his mother spoke, shattering his fantasy.

"Thomas, I want to talk to you when you are finished."

Unmasturbated, and his pornography hidden, Thomas sat at the kitchen table listening as his mother explained the special delivery instructions Ms. Fortune had required for her newspapers.

Two doors down, Audrey Green was staring disbelievingly at the erotic tableau before her. Her own kitchen window faced into the window of the woman next door. She hadn't had a chance to properly introduce herself just yet, but she was meaning to go over there later this afternoon. Then, as she was doing dishes, she saw the Italian lady sauntering into her kitchen with a leash in one hand. Before Audrey had a chance to wonder what kind of dog it was, a naked man followed her in on all fours. He was almost like an animal, she thought. He was covered in thick masses and whirls of coarse black hair and his cock was gigantic! The leash that the woman led him by was attached to his big balls. Audrey had brought her hand up to her mouth to stifle her gasp of astonishment. The naked brute was carrying some kind of white cloth in his mouth. Reaching the center of the kitchen, the woman stopped and turned to face the beast at the end of her scrotum leash. Audrey noted that it was a wide thick leather collar that actually pulled his huge balls downward and away from the base of his penis. She fanned herself with one hand as she watched his mistress reach down to take the items from his mouth. They were a pair of pristine white silk lady's gloves. She put them on, smoothing them around each finger before going over by the refrigerator to retrieve an old metal bucket… and something else that she couldn't identify. It was oddly phallic in shape and size but smooth with a wide base and a smaller top. The black device seemed to be made of a strong rubber and didn't yield the least as she gripped it in her white-gloved hand. It seemed unusually long to Audrey, who had yet to ascertain its use. She set the bucket down on the floor and, pulling on the leash, directed her male to take up a position on all fours with his cock directly over it. Audrey watched then as the Woman In Charge sauntered around to his bare bottom and reaching down to pry one asscheek to the side, proceeded to work the wicked black implement deeply into the male's ass. The poor dear didn't show the least discomfort or shock at what was being done to him, and Audrey had to conclude that she was seeing something that was very common to the couple next door. Now, as she continued to watch, the Italian woman began removing the skirt of her business attire, reavealing the bottom of an old fashione white girdle attached to her fine black stockings with heavy straps. Her upper half was almost puritanically covered, while from the waist down she was a young man's masturbatory venus. For a moment, Audrey allowed herself to think of young Thomas, the paperboy who was also her neighbor. She imagined from his bedroom window, he would also benefit from this show. In her mind, she saw him standing in his little bedroom with his white underpants pulled down to his knees… his stiff little penis in his hand… jacking… what was she thinking!? She was a respectable woman and she had been thinking about the neighbor boy masturbating! With a controlled exhale, Audrey reasoned to herself that she was only human and her thoughts were being greatly influenced by what was going on in the neighbor's kitchen. The attractive brunette brought a very small stool over next to the male and sat down on it, her stockings pulling tight as she did. She began talking to the man, stroking his bare back and ass as one hand stole under him to grasp his erection in her gloved fist. She began a very slow very gentle stroking motion that reminded Audrey of a cow being milked. Then she realized the bucket's purpose. My god… this man was being milked like a cow, his sperm collected in a bucket like an animal. Audrey went faint and realized that her panties were very wet in the crotch.

In the other kitchen, Ms. Fortune's milking slave was panting and sweating a bit. The female hand between his legs was pulling harder on his cock and making his balls bounce comically. He grunted and arched his back eliciting a sharp spank to his rear end from his owner.

"Stay still, you!"

The pathetic male was, of course, forbidden to speak. The leather dog collar around his neck bore a small metal id tag that proclaimed his name as "Ms. Isabella's dickhead". Ms. Fortune looked under the beast to observe the contents of it's bucket. It was almost half full from previous drainings and she intended to add more this afternoon. She was a woman who believed that dickheads like this stupid male were born for the milkings she provided. She believed it kept them docile and enslaved to a world of perversity that they were fully suited to. Some men might be marriage material, but then there were these creatures. Her mind turned to the young man who was going to be her paperboy. She thought she could sense a certain guilt in him… the way he was unable to meet her eyes… the way he stole little glances of her stockings… his quick retreat to his bedroom. She tightened her grip and jacked harder on the penis in her dainty gloved hand.

Audrey, who had been watching for some time now, was being confronted with feelings she had never felt before. As the pervert on the leash was thoroughly masturbated for his cream, she began to think that just maybe this was as it should be. It probably didn't work… couldn't do much in life except exist to please it's Mistress. She found herself chuckling softly. She couldn't wait to meet this woman.

Thomas ran over the instructions in his head again. Ms. Fortune required her newspapers to be delivered directly to her dining room table. A key was to be found taped to the mailbox and he was to enter quietly, drop off the paper and leave. She was, his mother explained, a very busy woman and didn't have time for chit chat with paperboys. His thoughts were interrupted by the sound of his mother's car leaving the driveway for his aunt's house, where she would spend the afternoon visiting. Quickly, he ran up the stairs to his bedroom and began undressing. Once again, naked but for his socks, he stood there and began to stroke his enflamed penis. As he jerked off, he noticed movement out of the corner of his eye from the house next door. He turned to face his window completely and his eyes widened to saucers at the spectacle presented in the kitchen of Ms. Fortune.

Isabella thought that her pervert might be getting close to squirting as its ass had started humping just a bit more agressively. It was now driving it's cock down angrily into her sweet gloved fist. She cooed at it and said sweetly dirty things to encourage it to make it's disgusting mess. The thing's balls were slapping loudly in the little kitchen as it humped and grunted like a rutting pig, desperate to relieve itself of more semen. Isabella absent-mindedly ran a finger back and forth across its bound scrotum as her she thought of the paperboy… and then she had a wicked idea. With no explanation to Dickhead, she let go of its penis and left the kitchen. Her full ass rolled invitingly in her matronly white girdle, peeking out from beneath her shirttails. When she returned a moment later, she was carrying a condom package. Seating herself again on her stool, she pressed the package to dickhead's lips and he wordlessly chewed it open for her. Then, she withdrew the small white circle of rubber and began rolling it up the length of his stiff penis. He grunted with frustration at not being able to feel the soft friction of her gloves and was again soundly spanked for his rebellion.

"BEHAVE! You will make your mess in rubber. No sass mama, dickhead."

Then, she resumed her aggressive stroking of his cock. She tickled his hairy balls as she beat him off and laughed at his absence of dignity.

As Audrey watched with full attention, the male began its beastly climax as its owner coaxed it out of him with her hand. He was being spanked across his bare bottom as he emptied his awful sperm into the condom. Audrey had been quite the cocktease in her youth and given her share of handjobs to boys but truly recognized the expertise of the woman next door. After several minutes, it was dragged to a kneeling position in front of its Mistress as the condom was examined. Again, Audrey stiffled a gasp at the sight of the condom tip, ballooned outward with its heavy burden of sperm. The Italian lady carefully stripped it off of her pet, careful not to lose a drop of the thick semen.

Next door, Thomas began to ejaculate at the sight of the male being masturbated. Completely unhinged, he had begun to crouch slightly with the intesity of the discharges that splattered noisily against the window pane. He landed in a heap on the bedroom floor and groaned like a wounded animal staring up at the rich deposits of cream he had generously spurted against the glass. He clung to one terrible thought in the creeping darkness of the late afternoon… he wanted to be masturbated that way.

Warren was led back into his little dog cage by Ms. Fortune. She removed the leather ball collar and rubbed a bit of lotion into the sac to avoid chaffing. With a smart crack to his ass with the crop, and the locking of his cage, he was sent to bed. As he drifted off, he recalled how this exotic woman had taken charge of him from the beginning. He had been a transient in bus stations, which is where he met her. His life had been a failure and he wasn't terribly bright. However, from the moment there eyes first met, it seemed she could see the need in them… and hear it in his voice when he spoke. He was, and always had been a pervert. She had ensnared him easily with sexy stockings and terse commands floating on a wave of cigarette smoke. He curled up in his cage and fingered the little tag on his collar. Dickhead fell into a restless sleep.