Gary and Jane Pt. 06

Jane could feel Alisha increasing her efforts as the hands on Lady Mary`s watch moved around. Jane had to concentrate very hard to ensure that Alisha's oral abilities did not bring her to climax before the time had elapsed, as that would ruin the next part of her plan.

All of the people were watching with baited breath as the dark skinned girl attended to Jane`s pussy with her small and deft tongue. Eventually Jane could not hide from the pleasurable sensations emanating from between her legs and mewled loudly as she came and covered Alisha's face with her juices. After she had regained her breath she turned to Lady Mary and asked, "Time?"

The older lady had an evil smile on her face as she said, "Five minutes and forty seconds. She failed!"

The sun was starting to dip below the trees and the evening was getting cooler as Jane addressed the gathering. "It appears that my little submissive has failed in her first test and I must therefore sadly punish her. This will take place in the punishment room in thirty minutes!" She looked at Gary before continuing, "Gary please take care of our guests and escort them downstairs in thirty minutes while I prepare this girl!" Looking at Simone she continued, "Simone please clear everything up to my satisfaction or you will have your turn on the cross and I will let Lady Mary discipline you. Is that clear?

Simone nodded and said without emotion, "As you please Madam!"

With that Jane left the pool area dragging Alisha by the arm and taking her down the stairs to their play room where Alisha`s eyes widened as she saw the cross and the punishment stool.

Jane turned to her and said softly, "You know you can stop this at any time, but you told me that this is one of the things you wanted. Is that still the case?"

Alisha thought for a minute before slowly nodding her acent.

"Now, to the next part of your fantasy," Jane said in her Mistress persona that had returned immediately after Alisha had nodded her head.

"W-w-what is that?" stammered Alisha as Jane led her towards the cupboard in the corner.

"Tonight girl Gary will take your anal cherry and for that we must prepare you!"

"I-I-I am not sure!" Alisha stuttered.

"You will take his cock in your arse and you have no choice if the others want to make use of you this evening as tonight you are my submissive slave! The only word that will save you is coconut, and then this whole fantasy will stop and will never happen again. Understood?"

Again Alisha nodded.

Jane led her to the whipping stool and laid her over the red leather, cushioned top before returning to the cupboard. She selected a large tube of lube from the contents and a butt plug with a maximum diameter of one and a half inches. These she took back to where Alisha lay unmoving but with wide eyes as she followed Jane`s every movement.

Jane poured the lube generously into the puckered hole that was displayed perfectly by Alisha`s position on the whipping stool. Jane began to massage the lube into Alisha`s forbidden hole using one finger, that she had to push in hard to bypass the tight sphincter muscles of this anal virgin. Once she had got the finger completely into her arse she moved it in a circular motion widening the hole. The initial penetration drew a loud scream from Alisha that only subsided as her muscles relaxed and accepted the invader.

Jane poured more lube into the small gaping hole after she removed her finger and then pushed two fingers in, widening the gap even more and producing another loud scream from Alisha, but noticeably no mention of coconut. Jane wiggled her two fingers and stretched the protective muscles of Alisha's anus.

Once she was satisfied that she had enough to work with she withdrew her fingers and poured more lube into the puckered hole that was now gaping nicely. Applying a liberal coating of lube to the butt plug she positioned it at the entrance to the girl's back door before pushing it slowly into the widened hole she had created with her fingers. The butt plug was accepted with very little resistance until it reached its widest point where upon Jane had to push more strongly before it slipped in and the anus contracted around it and Alisha moaned deeply as she bit her hand to stop from crying out.

Jane left Alisha to become accustomed to the anal intruder and walked quickly to the cupboard, before returning with the egg that she had used in Kenya. She placed her hand between the girls legs and feeling the saturated state of her gash she knew that lubricant would not be required and she slipped the egg inside Alisha`s pussy. Alisha gasped at the new intrusion to her lower regions and that gasp became a loud resonating moan as Jane flicked the remote control to a medium setting and activated the egg.

Again Jane waited for Alisha to adapt before helping her up and leading her to the cross. Alisha`s short stature made the attachment to the ankle straps quite difficult as her legs were splayed three feet apart. Jane then attached her wrists to the cross before activating the ratchet system that stretched Alisha on the polished wood like a Spanish Inquisition rack. She was now suspended with her feet nearly one foot off the base plinth and her legs and arms held tight against the spans of the cross. The stretching had caused her buttocks to part revealing a delicious view of the butt plug glinting between her cheeks.

Jane surveyed her work as she heard the imminent arrival of the others as they made their way down the stairs to be greeted by the sight of Alisha suspended and splayed on the cross with the fact that she had been butt plugged more than apparent.

Lady Mary was the first to enter with her slave behind her attached to her leash. At the sight that greeted her she sighed and mumbled, "Beautiful, just wonderful."

Then came Sandy and Kevin who said nothing, but just took in the spectacle with a look of shock, mixed with arousal.

Gary was last and accompanied by Simone. For the first time Jane saw Simone nearly lose her composure as she took in the sight of the girl spread eagled on the cross. Gary just looked at Jane with eyebrows raised and mouthed "Are you sure?", at which Jane nodded and winked.

"Where is Ian?" Jane asked to nobody in particular.

"Zonked!" said Sandy, "We couldn't wake him up as he had smoked all the happy baccy!"

Jane looked at Simone and instructed her to replenish all the drinks. She nodded and went behind the bar and started to make the drinks for them all whilst glancing at Alisha`s prone body. Jane couldn't tell if that look was one of pity or jealousy but deep down she thought it was probably the later.

Jane gazed at the assembled crowd and spoke loudly as if she was announcing an execution in Middle Ages England. "My Slave Alisha," she started, and turned to point at Alisha. "Has been found wanting in her duties. She was instructed to bring me to orgasm within two minutes and failed miserably." This brought a few mock boos from the four people watching. "She has been sentenced to nine strokes of the cane upon her naked bottom." Alisha moaned loudly at this point, before Jane continued, "Those stripes will be administered in the following fashion. Three by myself, three by our Master Gary and three by our guest of honour Lady Mary." The last part was greeted by a squeal of delight by the masochistic old dyke as she clapped her hands with glee. "Alisha will have the choice in which order to receive those stripes. Alisha, who would you like to go first?"

The girl on the cross was silent for a good minute before she said breathlessly, "I would like Master Gary to be first and please be gentle with me Sir, I beg of you!"

Before they could begin Simone came out from behind the bar and started to hand out the drinks she was carrying on a tray. She handed drinks to Kevin, Sandy and Gary with no problem, but as she approached Lady Mary she tripped over the girl laying on the floor and the entire G & T was deposited in Lady Mary`s lap, drenching the chestnut hair of her landing strip.

Her Ladyship screamed in shock before viciously slapping one of Simone`s B-Cup breasts with her hand and shouting at her, "You stupid bitch, now get down there and clean this mess up, and when we are finished with this useless wench I demand that Master Gary makes you replace her!" and with that she looked knowingly at Gary.

Gary was silent for a few minutes as he watched Simone drop to her knees and start to suck the gin and mixer from her Ladyship`s pubic hairs and she stayed in position licking every drop that had dribbled down the women's pubic mound and onto her labia below.

Gary watched the scene unfold before him and in a stern voice he addressed Simone," For your clumsiness you must be punished. You do accept that this is the inevitable result of your actions don`t you Simone?" In phrasing it this way he hoped to give Simone the opportunity to avoid what would probably be a terrible thrashing at the hands of the sadistic old bitch, as she could halt the role playing.

To his astonishment Simone raised her head from between the older woman's legs and said softly, "Of course Master. I should be beaten for my clumsiness and Her Ladyship has every right to carry out that disciplinary measure. Whatever you decide that should be." She then went back to licking and sucking Lady Mary`s gin soaked snatch, which was incidentally now becoming wetter instead of drier.

That was now decided and Gary stepped forward and was handed their favourite cane by Jane. Before he delivered the first blow Jane turned to Sandy and told her, "Please be prepared to suck my Master once he has finished, as the punishments always heighten his arousal."

Sandy coughed on her drink at this but nodded as Kevin turned to her and winked his approval with a big grin

.

Now they were ready. Gary raised the cane and brought it down hard across the light brown buttocks of the girl tethered to the cross. The cane created a perfect line across the middle of Alisha`s posterior that was only broken by the base of the butt-plug, as Gary had hit the target perfectly and forced the plug further into Alisha`s anus. Alisha screamed loudly and tried to wriggle against her restraints. She was still whimpering and tears were falling from her eyes onto the carpet as Gary landed the next two blows and her screams both times got louder.

Jane asked Alisha, "Who would you like to deliver your next three stripes?"

Alisha was crying openly now but still had not used the safe word. She took a few moments to gather herself before stuttering, "I-I-I- would very much like it if you would go next Mistress." And she clenched her fists as she waited for Jane to bring the cane down upon her.

Jane glanced at Sandy who slipped from the stool where she was perched and dropped to her knees in front of Gary and sucked his rock hard erection into her mouth. With the noise of Sandy slurping on Gary`s cock and Simone still lapping furiously at her Ladyships snatch Jane stepped forward and landed a stinging blow on Alisha`s behind. Alisha screamed like a banshee as the second and third blows landed in quick succession.

Lady Mary was up and striding towards Jane before she could say another word. Snatching the cane from Jane`s hand she landed three blows in less than ten seconds. Every one hitting her preferred target of the butt plug in Alisha`s arse. She handed the cane back to Jane and resumed her position on her stool where Simone went back to work between her legs.

The caning had obviously heightened Lady Mary`s arousal as within seconds she was pushing Simone`s head into her crotch with her hand and screaming in a very unladylike way, "That`s it you bitch, lick this wrinkled old snatch and I am going to squirt all over your beautiful young face before I flay the skin off your perfect arse. Yes, yes stick your tongue in there I am nearly thereeeeeeeeee!" and she threw back her head and exhaled loudly as she reached her climax and squirted her juices into Simone`s mouth while clenching her legs around the blonde head keeping her in place until her shudders had subsided and Simone had licked her clean.

Jane glanced at Gary and Sandy, who`s head was bobbing up and down frantically. Gary had his eyes closed and was obviously very close when Jane shouted "Stop! Don't make him come as we have another use for our Master`s seed!"

This caused Sandy to turn and let Gary`s dick fall out of her mouth and Gary to stare at Jane with pleading eyes.

Jane went to the cross and lowered Alisha down after releasing the restraints. The girl was crying softly and her body was wracked by shudders and Jane realised that she had climaxed while they were all watching Simone and Lady Mary. It was also apparent that it wasn`t her first orgasm of the evening as after she was freed she could not walk unaided on her rubbery legs. She looked like a human Bambi as she struggled to get her balance.

Jane laid her carefully on the whipping stool and reached between Alisha`s legs and removed the vibrating egg. Gingerly she pulled the plug from her arse, and as it left the tight enveloping muscles it made a loud pop. She went to Gary and leading him by the dick she pulled him over to where Alisha lay with her anus open and gaping waiting for Gary`s cock. Using her hands she smeared more lube on his dick before guiding Gary`s cock to the stretched opening. He used his hips to push his penis into the virgin arse displayed before him.

Alisha moaned loudly as she felt Gary pushing his dick deeper and deeper into her. Once he was completely encased and his pubic mound was rubbing painfully on the welts caused by the cane he began to slowly pump in and out, increasing the tempo with each thrust. As Jane had planned, by getting Sandy to blow him, he didn't last long and erupted inside Alisha`s rectum in less than a minute. Alisha bucked against him wildly as another climax rippled through her body but no sounds came from her throat as she was totally spent.

Gary carried Alisha`s limp body to the sofa and placed her gently down and covered her body with a blanket as she fell into a deep sleep. As he turned he saw Lady Mary glaring at him and knew what was coming now.

He walked towards Simone and took her by the hand and led her to the cross. As they walked he leaned in close and whispered in her ear so the others could not hear, "You don't have to do this if you don't want to you know!"

Simone was obviously highly aroused as she practically panted her answer, "I want this more than anything!"

Gary strapped Simone to the cross and pulled all of the restraints tight so she was pressed hard against the wood. When he was finished he turned to look for Lady Mary, and at first he was confused that she wasn't on her stool and then he saw her looking through the cupboard. She turned away from the cupboard and Gary saw that she had selected the cat-o-nine-tails which was probably the most painful thing she could have chosen. Once again he whispered to Simone, "Are you sure?" and watched as the blonde head nodded.

Lady Mary walked towards Simone taking practice swings with the evil whip in her hand. She turned to Gary and asked, "What is the sentence for this wench Master Gary?"

Gary was unsure what to say. Too few and Lady Mary would be deeply offended. Too many and she may kill poor Simone. He took a deep breath and said, "Seven."

Gary heard Simone take a deep breath and he was relieved to see Lady Mary smile and nod her appreciation of his decision.

Lady Mary stood just to side of the cross that held Simone before bringing the whip down hard on Simone`s buttocks and lower back. As she drew the whip back Gary could plainly make out nine angry red welts that mixed with the six he had already given Simone earlier that afternoon, when they had their private play date down here. Simone was silent.

Lady Mary raised the whip and brought it crashing down in nearly the same place. Simone again stayed silent but Gary could hear her rate of breathing increase. The third blow caused Simone to tremble as it was aimed lower and hit the bottom of her buttocks and her upper thigh above her lace stocking tops.

The fourth blow covered the entire area of her alabaster buttocks and at last Simone made a sound. It wasn`t a scream of pain but a throaty moan as she orgasmed and her body rattled against the cross as the orgasm spread through her body.

The fifth, sixth and seventh blows where delivered with less venom as Lady Mary tired. They were still enough though to break the skin in multiple places and cause Simone to climax again.

Gary untied Simone and helped her from the cross. She fell to her knees and was taking deep breaths to get her body under control after the beating and the orgasms it had given her.

Lady Mary announced in a very matter of fact way, "Well it was a pleasure, but I really must go as my chauffer has been waiting outside for hours." With that she slapped the arse of her slave and said, "Fetch my dress." The slave bounded up the stairs and returned within a minute with the dress and pulled it carefully over her mistress's head.

Gary showed the two of them to the door and nearly collapsed in shock when he saw the huge Rolls Royce in the drive and a chauffeur in full livery get out and open the rear door for her Ladyship and the slave. The both entered and Lady Mary turned and waved as the big limousine pulled out of the drive and headed to Bedfordshire.

As Gary was going back downstairs he met Ian who asked him if he had missed anything, which caused Gary to laugh out loud as Ian stared at him through blood shot eyes. They went down the stairs and as they entered Gary was surprised to see Kevin pumping into Simone from behind and the big blonde was pushing back hard into him and banging her damaged arse on his hard stomach. They were both breathing hard and climaxed simultaneously before collapsing on the floor.

Gary decided to call it quits for the night and suggested to Ian that he and Alisha stay in the spare room. Ian was still not really aware of what was happening as Gary showed him upstairs to the guest bedroom and where the bathroom was and as he left and started to close the door he saw that Ian was already on the bed and snoring loudly.

As he returned downstairs he saw that Kevin and Sandy were standing by the front door getting ready to leave. Sandy kissed him on the cheek and Kevin slapped him playfully on the back and laughing said, "Fuck me Mate! You know how to throw a party! I have seen some weird shit in my life but what you have going on here beats all of that by a million miles! Sleep good Mate!" and with that they left to stagger the few yards next door.

Gary walked downstairs to find Simone and Jane tidying up and Alisha still snoring gently on the sofa. Gary picked up Alisha like the little bird she was and carried her upstairs. He placed her next to Ian on the guest bed. Covered her once more with a blanket and went to help Simone and Jane. He met the girls on the stairs as all the cleaning was finished so he U-turned and went upstairs.

Arriving at the bedroom Simone walked into the bathroom and Gary heard the tub filling as Jane said, "I told her she could sleep with us tonight. I hope that is OK with you?"

Gary nodded and went to use one of the guest bathrooms as Jane walked into their bathroom to talk with Simone and show her where everything was.