Cum Stained Nylons Training

This story is a follow up to Cum Stained Nylons

.........

Jimmy brings a friend.

.........

Veronica looked out from the sliding glass doors to watch the two young men at work in her yard.

She had a lawn service but had given them instructions to leave some things undone so as to enjoy the sight of the nervous teens trying very hard not to be seen noticing her through the glass.

She was thoroughly enjoying parading back and forth in the living room and putting on quite the show.

This time, the eighteen year old Jimmy had brought someone who had potential, the wealthy divorcee thought to herself.

When she had gone outside to instruct the boys on the tasks to be accomplished she noticed that the newcomers gaze went straight to her stockinged legs perched atop her three inch heels. She smiled inwardly and moistened.

Dexter was a schoolmate, fellow video gamer, and member of the chess club. He was the third friend Jimmy had brought around and he was quickly running out of friends to exhibit.

Dexter was much like Jimmy in physique and demeanor. It was obvious without it being said that he was also a virgin and a leg man.

The other friends Jimmy had previously brought over to purportedly help with the yard did not meet Ms. Aldridges approval. Each had proved a disappointment in that their nervous gaze was fixed more on Veronicas boobs than on her legs.

She so enjoyed toying with young men who had a fetish for, and fascination with her hose.

........

Since that first time with Jimmy after she had lured him from the shoe store, Veronica had become a constant obsession of the young man.

Jimmy remembered vividly their first encounter and had very much hoped that their would be more of the same and maybe even some real sex. He had never so much as held a girls hand up to then.

Real sex it seemed was not to be on offer any time soon Jimmy found himself thinking after several weeks.

Back on that day two months before, while their orgasms were subsiding, Veronica had told him to pull up his shorts, leave, and go home.

His boy jizz was still glistening on her stockinged legs and dripping from the side of her face when she had said to him that what had happened was nice, and might be repeated if he learned to follow instruction well.

Since that day Jimmy came by to deliver shoes or perform some household chores several times a week.

Most times he was given a monetary tip and thanked for his work.

He was disappointed that she showed no interest in any further sexual contact for the first several weeks.

He managed to sheepishly ogle the 42 year old vixen and her sensuous legs every time he could.

She took every opportunity to display them through, slit skirts, mini skirts, and sometimes even brazenly in stockings, garters, and panties.

She would brush against him and feel his erection through his shorts with her body. If he tried to put his hands on her she would slap them away and would reprimand him if he touched himself.

Only twice was he rewarded with orgasms.

Once, after three weeks of no sexual contact, and after he had completed a hard two hours work, she sat on his lap in a lounge chair by the pool and ground her ass against his hard prick while placing his hands on her thighs so the he could stroke her stockings while he dry humped her.

He came in his pants and the semen had seeped through the fabric and left a stain on Veronicas stocking tops.

She did not mind as she had kegaled herself to a nice orgasm while he had been blowing his boy load.

The other time was after he had agreed to start bringing friends over for her to inspect.

He was going to have to be in on the ruse of the need for help around the house and not let on that Ms.Aldridge was more interested in teasing virgins to distraction than in any real work needing to be done.

As a reward for his agreement to supply her with cougar meat, she had him expose his raging erection to her and had him sit on one end of the best sofa in her finely appointed living room.

She sat on the other end of that sofa dressed only in stockings, garter belt, panties, and demi bra.

She had allowed him to stroke her legs while she dipped a hand inside her panties and fingered her juicing pussy. He could smell her excitement.

She slowly ran a stockinged insole over his throbbing boy cock until the bottom of that foot was thoughoughly coated with the teens precum.

She had nudged and tickled his ever tightening nutsack with the stocking clad toes of the other foot. Her hot pink painted toenails even managed to scratch his hairless balls through the nylon.

When she pulled aside her panties and Jimmy had seen his first real live pussy being invaded by her frantic finger fucking he burst.

Rope upon rope of scalding boy spunk erupted upon the orgasming Veronica. She had directed his jizz toward her so that it would not stain the sofa fabric.

She did this with her stockinged feet milking and directing his jets until she was fairly covered from neck to knee.

Jimmy was in bliss but had not experienced any more exctasy from her, though untold delights were promised if he brought a new playmate suitable to her.

"I will suck on your big boy cock for you as a starter reward." She had cooed to him in their post orgasmic bliss.

......

That was three weeks ago.

......

She had touched and fondled Jimmy through his shorts a couple of times since but had mostly teased and ignored him.

Dexter, seemingly, might make things change.

Today had started well.

The first glance Dexter had given Veronica caused her to moisten.

He had drunk in her beautiful legs from her feet to the hemline of her short skirt and back again. He did this without being diverted by the obvious cleavage she was putting on display.

This disregard for her ample bosom and fidelity to leg gazing impressed the seductress.

"What's your name young man?" The cougar had asked.

After a pause of several moments, while keeping his gaze on her seamed stockings, and as his obvious boy boner tented out his pants he managed to stammer.

"DDDexter ma'am."

"And how old are you Dexter?"

"Eighteen last month ma'am."

"No ma'am here, you may call me Ms. Aldridge. You look quite a bit younger than eighteen. You haven't even started shaving yet."

She then asked, "Have you got a girlfriend Dexter?"

It seemed unlikely, and the lack of girfriend was confirmed by a negative back and forth shake of the head by the speechless youth.

Veronica caught Jimmy touching himself through his shorts and with a glare communicated to him that he should stop immediately.

She then smiled at him and mouthed the word "Later."

"Well Dexter, if you would like and can stay after the yard work, I might be able to give you some tips on impressing a woman. You have made a fine start by the way you are appreciating my beauty." She said patting his erection.

......

She left the boys to finish their tasks and made a few phone calls.

Two hours later Jimmy and Dexter appeared at the sliding glass door knocking gently.

Veronica opened the door wearing a new outfit that would give a dead man a hard on.

Four inch stiletto heels on open toed pumps which accentuated the exquisite curves of her white stocking encased legs.

The lacy tops of the hose were visible and meeting the clips to a garter belt.

A leather mini skirt slit to the hip on one side hugged her firm ass cheeks and her upper half was encased in a sheer body stocking from wrist to waist to neckline.

Her full and breathtaking breasts with their erect nipples were clearly visible through the transparent material when the unbuttoned blouse she had thrown on flapped open.

Veronica opened the slider and motioned the boys inside.

Just then the doorbell rang.

"Wait here a moment." She said to them as she went to answer the door murmuring to herself, "Right on time."

Jimmy was a little shocked when he saw Madame Dupree walking back towards them with Ms. Aldridge.

"Hello James." The sixty year old proprietor of the shoe store where Jimmy worked said.

She then added, "Who is your handsome young friend?"

"His name is Dexter." Jimmy replied.

"Well Dexter, it is very nice to meet you." Teresa said eyeing the youth and noticing the way his gaze lingered on the stockings covering her plumpish calves.

A minute or so later the doorbell rang again and this time Veronica came back with two people Jimmy had never seen before.

One was an oriental lady of about five foot six dressed very much like Veronica was, and with nylon encased legs every bit as stunning.

Her dark closely cut hair and almond shaped eyes

were of course different from Veronicas shoulder length blond hair and blue eyes.

She appeared to be in her late thirties, but with oriental women it is sometimes hard to tell.

The woman Veronica was now introduced to the boys as Sunee. She had very petite breasts, but the boys were not noticing those, as both were staring at the bright red toenails visible through her open toed pumps.

Sunees companion was a young man in his early twenties. He was obviously known to both Veronica and Madame Dupree and was greeted by both.

"How good of you to come on short notice Brad."

Ms Aldridge said.

"I'm always ready to come for you." Brad replied.

"Indeed you are." Veronica said. "And you will show these two newbies what it takes to come for me."

"Yes mistress."

Veronica then explained to the stunned teenagers that Brad had been a project of hers a few years back when he had been young and naive.

He was now finishing up college and she had turned him over to her good friend Sunee for advanced training.

Sunee was a professor of economics at the college Brad attended. She was also a long time friend who shared Veronicas love of teasing and pleasing stocking worshippers.

Sunee said to Brad. "Show these two how to properly warm a lady up."

"Yes mistress." Brad replied.

He then got down on his knees and took off one of Sunees pumps while she reclined in a chair.

He kissed her nylon clad foot and began a trail of kisses that ended on her inner right thigh.

He changed over to the left thigh and began to trail kisses and licks down toward the foot on that side. Sunee had placed her left foot on Brads right shoulder and used it to pull him forward towards her pussy.

She had worn panties which were sheer and crotchless. Jimmy and Dexter moved to a better position enabling them to see Brads next move and Jimmy saw that this Asian vixen had a shaved pussy which was visibly wet.

"May I masturbate mistress?" Brad asked.

"Yes you may. And you may begin to please me with your mouth." His teacher replied.

"Remember that you are not allowed to come until I tell you but you may stroke your cock on my stockings."

Brad stood and removed his pants and an impressively thick eight inch hard on sprang into view.

He got down again and proceeded to lightly kiss Sunees exposed vulva and train lightning quick flicks of his tongue on her engorged clit.

She squirmed with delight.

Veronica told the two teens to stand before Madame Dupree and let her remove their pants.

Both teens obeyed and their burgeoning erections also sprang in to view when the voluptuous grey haired matron dropped to a squatting position between the youths and pulled each ones pants down and off.

Jimmy was sporting his ten inch horse cock and Dexter had a more modest and slender one at about five inches. It was also half the thickness of his friends boner.

Madame Dupree took one prick in each of her hands and slowly stroked them to further rigidity. She used her thumbs to smear their boy precum over the heads of the cocks.

"That should be enough Teresa, don't you think?" Veronica opined to the older woman.

Madame Dupree said, "Oui madame." then she gave each teens scrotum a tug and caress with her delicate hands and rose to a standing position.

Sunee was now writhing in exctasy due to Brads oral ministrations.

She gripped a handful of his hair and pulled his face further into her crotch. She ground her juicing pussy against his lathering tongue.

His erection was being kept at the boiling point by Veronica, who had taken off her pumps and was running a stocking covered foot over his ass as well as making contact with his balls.

For his part Brad was grasping his cock and slowly rubbing it on the nylon clad calves of the orgasming teacher. He was leaving streaks of precum on the hose.

"Jimmy," Veronica said. "I would like for you to please Madame Dupree as Brad is pleasing his teacher. We will instruct you and young Dexter here on the finer points of cunnilingus but first I have that treat I promised you."

With that said, she dropped to her knees and took the boys ten inch dick in her hand. She kissed the head and Jimmy gave a shudder and almost lost his balance.

Veronica then squeezed very hard at the base of his cock to delay the inevitable and help edge her new sex boy-toy.

Taking the mushroom head in her mouth she swirled her tongue around it twice and then went down about halfway to the root of his dick leaving a trail of red lipstick as evidence of her indulgence.

She went down once more, this time getting almost to the base, and then pulled her lips away, leaving a trail of saliva.

"That was very nice now wasn't it Jimmy?"

Jimmy reached to stroke his throbbing prick and effect a much needed release of pent up sperm but Veronica slapped his hands down and said.

"I promised I would suck your cock but said nothing about coming just yet."

Jimmy groaned in frustration and shot a sidelong glance at Dexter, whose prick was being sucked by Madame Dupree.

She too, had squeezed the base of her victims cock and tugged on his nuts to delay and deny his orgasm for now.

She was able to deep throat the trembling youth and had also left a lipstick trail on the teens cock.

"I believe they are ready for their lesson Teresa."

Veronica said.

"Sunee, if you are through squirting all over that nice young man's face perhaps you two could both lend a hand helping me instruct these youngsters in the finer points of pussy eating."

Madame Dupree then sat down and hiked her skirt up around her waist exposing fully her stocking clad thighs and neatly trimmed bush.

There were flecks of grey in her pubes and her outer lips were open and inviting as she separated them for the boys inspection.

Brad told Jimmy to kneel between his bosses thighs and to begin exploring this mysterious area with his mouth and tongue.

He gave both Jimmy and Dexter pointers as they took turns eating the Madame.

Sunee and Veronica placed their hands inside stockings and were using the silky fabric to masturbate and tease the boys turgid dicks.

Each cougar had an innate sense as exactly when to stop touching them so as to keep them on the torturous edge of explosion.

After about thirty minutes of having her pussy licked and explored by the virgin teens Madame Dupree was ready for some serious fucking.

Her clit was fully erect amidst her wispy grey speckled pubes and her lips lathered up nicely by the boys saliva and her own arousal.

She told Veronica "I'm ready for some hard young cock."

It had been many months since she had been with a man.

With a nod from Veronica Brad got some cushions to lay on the floor for Teresa, being careful to place one under her ass for easier access to her dripping cunt.

He positioned himself between her thighs and taking his cock in hand ran the head up and down between her labia to moisten the tip.

He then penterated the excited matron and felt her vaginal walls grasping and sucking in his cock inch by inch, her hips rising to take him all in.

Brad made an effort, Veronica pointed out to the boys, to insure that the top of the shaft of his cock maintained contact with the widows clit.

"Notice," she said. "How he rolls his hips to grind her clit when he is deeply imbedded."

Brad fucked the Madame slowly and deeply for a full twenty minutes, through a series of orgasms voiced by the matron in a mixture of French and English.

Jimmy and Dexter watched in fascination while their cocks continued to be fondled and edged by the stocking weilding cougars.

The women squeezed and tugged periodically on the nutsack of their respective teen to continue denying their orgasms.

Sunee playing with Jimmy and Veronica with Dexter were true vituosos of tease and denial.

Able to take no more Brad finally gasped. "Permission to come mistresses?"

Simultaneously the two cougars answered. "Permission granted."

Veronica added. "Fill her box you naughty man."

Brad sped his pace and started a rapid assault on Madame Duprees cunt. His hips rising and falling in a blur and her hands clawing at his back to pull him in deeper.

She was orgasming and squirting copious girl juice around his cock when he finally stiffened and shot volley after volley of hot jizz deep into Madame.

His orgasm was heightened by Veronica rubbing a stocking covered foot on his exposed balls while he was still, fully bottomed out in Madame, and spasming jets of cum against her cervix.

He pulled out with a plop and a stream of jizz seeped immediately from Teresa's now thoroughly plowed cunt and onto the cushions.

........

Veronica now said. "I think we will have a contest to determine who gets their cherry popped today."

She directed Jimmy and Dexter to a position opposite Sunee, who was seated with her stocking clad legs propped up on an Ottoman. She had placed her high heels back on and was openly fingering her shaved pussy.

Both teens were instructed to stand six feet in front of her and jerk their cocks. The object was to spray as much of their cum as they could onto the stockings Sunee was placing in their line of fire.

The one who got the most cum on her nylons would get to have his cock in a pussy for the first time.

They eagerly began masturbating but were having a tough time coming having been teased and kept on the edge for so long.

Veronica had pity and covering her hands with lube, stroked Dexter while Teresa did the same for Jimmy.

The women planned to release their grip and let the boys finish when they were close, so that they could direct the cumshot.

"This is getting me so hot." Veronica said aloud.

She had just been well and thoroughly fucked two days prior by her personal trainer Carlos, a thirty five year old who knew his business, but there was something about taking the cherry of a frantic teen which made her quiver.

Carlos had made her scream with delight and had even taken her ass as he was want to do, but what was in her hand was new meat and what was in Teresa's hand was even nicer.

"I hope Jimmy wins." She thought to herself.

"That ten inches will get me deeper than any stud to date."

Dexter grunted and his balls pulled tight. Veronica let go. Teresa did the same a moment later.

Both boys were jerking and came almost simultaneously.

Dexters jizz shot further and most hit the Asian vixen in the chest and face, some managing to coat her stockings, but not enough to best Jimmy.

He directed his ropes of cum perfectly up one stockinged leg and down the other. He even managed to coat Sunees fingers as she was frigging herself to an explosive orgasm.

She squirted a stream which soaked Jimmy in return.

"We have a winner!" Veronica exclaimed.

Wasting no time she had Jimmy lay on the floor cushions while she squatted and poised her dripping cunt above his erection.

Madame Dupree insured that it stayed rigid by holding it straight up and tickling his balls with her dainty hand.

Veronica squatted some more until the mushroom head made contact with her wispy blond pubes and then sank down fully on his engorged meat.