Prize Island Revisited Pt. 01

Raj nodded and smiled at her and then shouted, "More drinks please Diana!"

Diana had just finished delivering the next round as Moira pushed through the doors and into the bar. She took the proffered glass of white wine from Diana and perched on a bar stool and ran her gaze over the assembled couples. All eyes turned towards this fabulous creature who looked stunning in a green silk sheath dress and four inch heels.

"As I said before, I am Moira the Manageress here and this is Diana," she waved her hand in Diana`s direction. Greg and Harry you have already met. Now, let me explain about McKinnon Island. There are just six rooms. You are in rooms 1 to 6. Diana and I are in the staff annex behind the hotel. I am in room A and Harry and Diana are in room B. Greg is in room C. Please feel free to come to see Diana, Harry and I in our rooms should you require anything at all, and at any time. We are all here to give you the best experience possible. In the basement there is a small swimming pool, gym, games room and a sauna large enough for all of us. Please follow the rules and shower before swimming and the sauna is only to be used naked, but I would ask that you sit on towels to minimise the possibility of infections."

"The idea of McKinnon Island is that it is designed for romance. For couples to either make an already good relationship better or maybe to rekindle passions and reignite your sex lives. To that end we have provided some accessories in every room. These can be found in the nightstand next to the bed. If you require anything that we haven`t thought of please don`t hesitate to ask Diana, Harry or myself. We are all adults here and so what you do, and with whom, is not of anybody's concern except yourselves. What happens on McKinnon, stays on McKinnon!" and she laughed. Her whole face lit up and her eyes sparkled as she laughed and the six couples joined in.

"Breakfast is from nine until ten. Lunch is between two and three and dinner is punctually at eight. You are free to go anywhere in the house or the island, except the kitchen. Greg gets upset if people traipse through his domain. There is a small sandy beach to the West behind the house. There is also a hot tub on the patio area just outside the bar." Moira pointed at another pair of double doors at the back of the bar and everybody turned to look. The large hot tub was easily visible. "I think that is everything. I say it once more. If there is anything that I can do personally for you individually, or maybe as a couple then I beg you, please ask. There is nothing that we here at McKinnon's Island will not do to ensure you leave here with all your fantasies fulfilled."

Moira stood and said, "Now you must excuse me as I have some things to do. I will see you all at dinner. Please remember what I said and if I can be of any assistance please do not hesitate to ask. Your satisfaction is my only purpose!" and with that she left the bar.

After she had left the bar Diana stood and listened as the group discussed Moira`s words. Malcolm was the first to put into words what they had all been thinking, "Did she just say that we could sleep with the staff including her?"

Michael spoke in a deep baritone as he answered, "That`s what it sounded like. It also sounded as if she wasn`t fussy if that was a man, woman or more than one."

Julie chipped in with, "Well I for one hope we get to have a half an hour with that beautiful creature." With that she clasped Bella`s hand and kissed her gently on the cheek.

Diana`s ears pricked up as she heard Rose and Anita discussing the possibility about screwing Harry as he looked very handsome. The last bit filled Diana with pride. Diana had also worked out where her next spanking was coming from as Malcolm had already admitted to spanking Helen and she had heard him describe himself as a retired Headmaster. Hopefully he would be experienced with all forms of punishment. Helen was also fascinating her and Diana was already contemplating burying her head between those refined thighs.

Diana was still lost in thoughts of Malcolm flogging her as she licked Helen`s pussy as she noticed Dominic go to the restroom and return barely two minutes later with glassy eyes and tell-tale traces of white powder around his nostrils that confirmed her suspicions.

Moira returned and asked them all to follow her as dinner was served. Diana watched them file out and Malcolm and Helen were at the rear of the group when Diana stopped them and said in her special submissive voice, "If Sir and Madam require anything at all, you only have to ask." And she was sure that she saw Malcolm`s eyes light up and Helen swallow noticeably. As she turned to collect the dirty glasses she could almost feel Malcolm`s eyes glued to her taut buttocks in the tight fitting black dress. She turned and smiled at the couple and caught Helen gazing into Malcolm`s eyes as her hand stroked an impressive erection in his cotton slacks.

Seeing that Diana had caught Helen playing with his dick Malcolm coughed and looked at Diana with his attractive brown eyes and said, "Please attend my office after dinner miss. I mean room. Your cheekiness will need to be dealt with most severely I think!" With that he turned on his heel and led Helen through the doors and towards the dining room.

Diana`s knees nearly buckled and her panties were now soaking as she anticipated her punishment from this strong, older man, and hopefully Helen would be part of the procedure as well. She quickly finished cleaning away the dirty glasses and the small bowls that had been full of snacks. Starting the dishwasher she went through the door at the rear of the bar into the kitchen to help Harry deliver the entrees to the guests.

The dinner went well, and all seemed in good spirits and were enjoying the food and wine. Dominic was zoned out and ate nearly nothing. Ann did not seem at all upset, spending most of the evening flirting with Harry and Raj, who now seemed to be her best friend after their earlier spat.

Diana watched as Ann finished the last mouthful of the crème caramel desert and then beckoned Harry over. Diana watched as he bent down and Ann whispered something in his ear. Harry nodded and then went back to clearing away the dirty dishes. Diana continued watching Ann as she said something to Dominic and he got up from the table and left the room.

Diana walked into the kitchen and put her arms around her husband from behind. Harry turned within her arms so they were facing each other and kissed her on the lips. Greg was busy putting things away in the larder so Diana pushed Harry out of the door into the garden.

Once outside she kissed him hard and began rubbing his growing erection through the thin cotton of his kitchen "whites". "Are you going to fuck Ann?" she asked whilst never stopping her hand moving on his now rigid cock.

"Yes. She asked me to come to her room at eleven. Why? You have a problem with that?"

"Of course not:" Diana said as she dropped to her knees before her man. "That`s what we do here. I just want to make sure you fuck her long and hard!" With that she pulled his loose fitting pants down and took him in her mouth. His hardness increased and she pushed him deeper into her mouth, her tongue working frantically on the tip and underside. Diana cupped his balls in one hand whilst using the other to run her fingers up and down the shaft with a featherlike touch. She knew he loved this and would be spurting in her mouth in next to no time. Harry was groaning loudly as Diana let his stiff rod go and then pushed down hard until the tip of his cock pushed into her throat. She held him there for five seconds before resuming her gentle finger masturbation. She felt Harry`s knees begin to tremble mere seconds before she felt the gushing warmth of his spunk filling her mouth. She grinned up at him as she sucked him dry before swallowing his creamy deposit.

"Now go and fuck here for hours my stud husband. Make her cry out her orgasms so the whole hotel can hear. By the way, I will be with Malcolm and Helen tonight so we can meet back at the room later. You better save a bit in the tank for me, as if all goes as I plan I will be horny as hell and needing a good fuck when I get back!" With that she rose from her knees, kissed him on the cheek and went back into the kitchen to help Greg. Harry followed her a few minutes later.

Harry, Diana and Greg were a good team and soon all was cleared away and every surface gleamed. They had been working together long enough that words were very rarely needed. By eleven they were finished and Greg headed off to bed with his usual two bottles of beer. Diana peered into the dining room and saw that Moira was just finishing the normal Sambuca with the guests.

Diana entered the room and made a beeline for Malcolm and Helen. Bending at the waist she whispered in his ear, "Would Sir like me to bring something with me?"

Malcolm reached inside his jacket pocket and pulled out a small pad and a gold fountain pen. Unscrewing the pen he wrote quickly on the pad, before blowing on the words to dry them and then folding the paper in half and handing it to Diana.

Diana withdrew to the kitchen and unfolded the small piece of paper. In perfect handwriting was written the following words, "If you would be so kind as to present yourself dressed in stockings, and If possible I think in this instance the use of a cane would be appropriate."

Diana could feel her juices soaking into the gusset of the silk panties she was wearing. Her love of nice lingerie had only been increased by her gifts from Scott's she had gotten from her first stay at the hotel. She was already wearing a matching garter belt and stockings so she just needed to grab the cane that Moira used from their room. She heard the guests leaving from the dining room to go to their rooms and so she quickly ducked out of the back door and made her way to the staff annex. The cane was where it always was and she grabbed it before deciding to wait a few minutes to allow all the other guests to be settled for the night. Her mouth was parched so she took a small bottle of Coke Zero from the fridge and downed it in one. Refreshed she picked up the metre long stick and made her way back into the main building.

The hotel was quiet as she started to make her way up the stairs to the rooms above. She was only on the first step as she saw Harry enter room number five. Room five and six were the only rooms on the ground floor. She smiled as she made her way silently up the stairs. Her four inch black leather heels making no sound on the thick stair carpet. There was no one around as she took a deep breath and knocked on door number one.

"Enter!" came the command from within.

Diana pushed the door and it opened easily. She entered the room and closed the door behind her. Malcolm stood in the middle of the room. He was bare chested and was wearing just a pair of pale blue cotton boxers. Diana could see that there was already a dark spot on the boxers where his pre-come was leaking from a quite impressive erection that was tenting the thin cotton. For his age his body was well muscled and his chest was covered in wispy grey hairs. He was standing nearly to attention with his hands clasped behind his back.

Diana looked around for Helen and found her sitting in an armchair in the corner. She was partly hidden behind the large frame of her husband. She was dressed in just a silky ivory negligee that fell to about mid-thigh. She was sitting with her legs crossed and a glass of what looked like G & T was clasped in one hand. The other hand held a burning cigarette that she raised to her lips before taking a deep drag and then exhaling a plume of greyish blue smoke towards the ceiling.

Malcolm spoke in his low posh voice, "Well Miss. You know why you are here. So let`s get straight to it shall we?"

Diana knew how to play this role so well. Her eyes fell to the floor and her hands were clasped around the cane behind her back as she said softly, "Yes Sir!"

Malcolm took a deep breath before he spoke, "Normally we would administer the punishment fully clothed. However, after discussing this with my wife we have decided that you should be flogged in just your underwear. To that end, please strip and hand me the cane."

Diana walked towards the man and handed him the cane. She released the clasp on the back of her dress and let gravity pull it to the floor where it pooled around her ankles. She stood in the middle of the room before this man now, in just a lacy bra, the soaking wet black silk panties, black stockings held up by a garter belt and her four inch heels. Diana heard both Malcolm and Helen take a sharp intake of breath as they ran their eyes over her body. Even Diana had to admit she looked damn hot in this lingerie.

Malcolm took his time gazing at Diana, and even walked around her so as he could view every angle. As he moved, and Diana could see Helen better, she saw that she had stubbed out the cigarette and was now sipping her drink whilst her right hand was busy underneath the negligee. Obviously she likes to watch Diana surmised. Hopefully she also likes to play was her next thought.

Diana was startled from her thoughts as Malcolm spoke from behind her, "Very nice Miss. You have done exactly as I asked, if not better. What do you think Helen?"

Helen stopped fingering herself for a second to reply, "Very, very nice my husband. Now please be a Darling and get on with flogging her. I am so close you know!"

"Yes. Yes Of course. Where shall we do it Helen?"

"Right there will be perfect. Turn her to the side so I get a good view. Diana be a good girl and bend over and clasp your ankles. My husband is right handed, so he will be to your left hand side so as not to spoil my view. Just turn slightly so you are at an angle." Diana adjusted her position as Helen had requested, and then bent at the waist and took hold of each ankle with her hands. "Perfect." Said Helen.

Diana had steadied herself and taken a deep breath in anticipation of the strike from Malcolm when she heard him ask Helen, "How many strokes Helen?"

"Let`s start with four Darling. That should be enough for me to get off. Then we can do a few more while I attend to your needs. How does that sound?"

Diana glanced quickly in Helen`s direction and could see her hand moving furiously under the nearly transparent silk of the negligee. Diana wished she could see what her hand was doing but it was hidden from her view.

"Ready!" came the curt question from Malcolm, and when Diana nodded she heard first the whistle of the cane cutting through the air, and this was followed by a loud thwack as it connected forcefully with her silk clad rear. The pain coursed through her body and she let out a shrill squeal. There was no time for Diana to compose herself as the cane landed a second time. Her squeal this time was answered by a low moan from the direction of Helen`s chair.

As the cane landed for the third time Diana let out a shriek as Helen groaned loudly. Those groans turned to a soft scream as the fourth blow landed and Helen climaxed at her own hand. The room was silent now apart from Malcolm puffing gently to her left. Diana watched as Helen withdrew her hand from between her legs. Even from here Diana could see that the fingers were shiny with her own juices. Diana stayed in position and waited to see what would happen next. The cheeks of her arse burned pleasantly as a couple of the strokes had connected with those already administered by Moira earlier that day.

Helen picked up her cigarette packet with her long fingers before removing one and placing it between her lips. Using a cheap throw away lighter she lit the end and sucked down a deep lungful of smoke before exhaling it towards the ceiling. Diana watched as she repeated the process at least ten more times before crushing the cigarette out in an ashtray.

Diana was transfixed as this elegant woman rose gracefully from her chair. She took a second to straighten her negligee before walking over to her husband. On the way she gathered a pillow from the bed and lay it at his feet. She lowered herself until she was kneeling before him and then in one deft action she pulled his boxers to the floor.

Diana watched speechlessly as Malcolm`s huge erection sprang into view. His cock must have been nine inches long. It wasn`t thick, but it was impressive.

Helen stated very quietly, "Please continue Malcolm and don`t stop until you come." With that she took his hard cock as far as she could into her mouth. There was still four or five inches outside and she began to stroke these with her finely manicured fingers.

Malcolm was starting to breathe heavily as he raised the cane and brought it down viciously across Diana`s buttocks. She cried out as this stroke was much more powerful than the previous four. Diana peered quickly to her left and saw that Helen was sucking his cock frantically and masturbating him at the same time.

The cane landed again. Was he hitting her harder and harder? It seemed like it to Diana as waves of pain crashed through her body. The cane landed five more times before Malcolm grunted loudly and Diana looked through tear stained eyes as Helen struggled to swallow the copious amounts of semen he was apparently ejaculating into her mouth.

Malcolm let the cane fall to the ground as his hands gently held his wife's head as he came again and again. Helen did not miss one drop and swallowed over and over until he eventually stopped jerking.

Diana collapsed to the floor. Every sinew of her body crying out at the pain, but the erotic nature of the whole evening also had her close to orgasm. As she lay on the floor her hand strayed between her legs. Her panties were soaked through and her middle finger slipped underneath the waistband and located her aching clit. Just one touch and she could feel her orgasm hurtling to the surface when she was brought rudely back to earth by Helen shouting, "Stop!"

Startled, Diana turned to look at Helen who was smiling at her. "Diana, the least I can do is bring you to a nice climax after all you have done for us:" With that Helen rolled Diana onto her back and Diana felt Helen`s long fingers pull the gusset of her panties to one side and then the older woman's tongue ran the length of her puffy pussy lips and ended by flicking her rock hard nub. Diana groaned loudly, and the second time Helen repeated the manoevre Diana exploded into one of the best orgasms of her life. Her body arched up from the floor so that it was supported by only her head and heels. Her body was shaking as electric bolts emanated from her pussy to all the furthest points of her body. Aftershocks wracked her body for minutes afterwards.

Eventually she started to calm. She opened her eyes and looked across at Helen and Malcolm who were sitting staring at her. Malcolm had his arms around Helen as she sat cross legged between his outstretched legs. Diana could just about see a tantalising glimpse of Helen`s sex at the end of the tunnel created by the negligee. Her view got better as Helen shifted position before pulling the ivory colored silk over her head.

Diana stared at Helen`s naked body. Her breasts were small and drooped slightly. Her flat stomach showed a few wrinkles. Her pubic mound had a small landing strip of thin blonde hair and this guided Diana`s eyes to the red swollen lips of her pussy. She really was stunning for her age.

Diana crawled on her hands and knees towards Helen. She had only one thought in her mind and that was to see what this beautiful woman tasted like. Helen anticipated Diana`s thoughts and uncrossed her legs, spreading them wide to allow Diana access between her thighs. Helen leaned back so her head rested on one of her husband`s thighs.