Prize Island Revisited Pt. 05

She entered the bar silently from the kitchen entrance and was surprised to see Malcolm sitting there. He was impeccably dressed as always in a jacket, crip white shirt and red and blue striped tie knotted tightly around his neck. This wasn`t what surprised Diana though. She saw the unmistakable blonde hair and thin neck of Helen bobbing up and down on Malcolm`s sizeable erection. He was leaning back in his chair with his eyes closed as his wife expertly blew him.

He let out a small groan as Diana looked on. She kept silent so as not to disturb the couple and watched as Helen rose gracefully from the floor and daintily dabbed at her mouth with a paper serviette to clean up the last drops of Malcolm`s sperm.

Malcolm opened his eyes and only then did the couple notice Diana observing them

Helen was also stylishly dressed. A long, armless, ankle length yellow chiffon gown looked perfect on her hourglass figure. A gold chocker around her neck and long drooping earrings with emerald and rubies completed her outfit. Her cleavage was well displayed as the V-Neck was cut nearly to her waist. There were noticeable bumps in the dress where her nipples were unfettered by a bra. She looked like a million dollars Diana thought to herself.

Helen lit a cigarette and said in her refined voice, "Oh, Hi Diana. We didn`t hear you come in. We hope you don`t mind me giving my husband oral relief in here but we came early in order to catch you before the others arrive. We were both hoping that you could be convinced to join us after dinner for a little bit of a menage et trois and discussing that possibility got us a bit hot and bothered?"

Diana smiled at her favourite couple of the week and said simply, "I would love to. However, we must go a bit easy with the cane if you don`t mind, as I am still in recovery from an extra painful session with Ann. If that's OK with you two I am in!"

Helen smiled back and said salaciously, "We didn`t plan on that being part of our repertoire. We were thinking more about the sex. If punishment is required, then Malcolm will just have to flog me. We have already started in a way you know." With that she pulled the loose straps of her dress down exposing her bare breasts. Both nipples were being pinched painfully by miniature silver clothes pegs. "I also have one doing terrible things to my clitoris, so I think Malcolm has nearly satiated his masochistic tendencies for the evening!" She pulled the dress back up and Diana saw her shudder as the material rubbed over her abused nipples.

"So that`s settled then. What can I get you to drink while we all think about what will happen after dinner. My panties are already moist thinking about it Helen!"

"I am so happy you feel the same as we do. Malcolm and I will take a G & T please. Ice and lemon if possible?"

"Coming right up. Can you show me your clitoris clamp while I make the drinks, please?"

As Diana poured a healthy measure of gin onto ice in two glasses Helen lifted her dress. Underneath she was wearing pale yellow panties that were nearly the same colour as her dress. Glancing furtively around to make sure nobody else was watching she moved them to one side with her long, elegant fingers.

Diana gasped as she saw an identical silver clothes peg attached to the older woman's clit. The small nub of nerves was already bright red and was obviously tightly gripped. Helen shivered as she replaced the silk panties and let the dress fall back into place jolting all of the clothes pegs.

Helen laughed self consciously as she explained, "The clothes pegs were a silver wedding anniversary gift from my dear husband. God bless him. We have had years of fun with them since then. They are solid silver. God knows what I will get for our Golden anniversary. Probably a 24-carat gold butt plug! Unfortunately the one I have in tonight is just plain old steel" All three of them laughed and were still grinning as Rose and Michael entered with Anita and Raj. They all looked exhausted so the fun must have continued after Diana had left.

"What`s so funny?" Raj asked looking from Malcolm to Helen and then at Diana.

"Oh nothing," replied Diana, "We were just discussing anniversary gifts that we had bought our husbands. The usual socks and nice shirts. Did you all have a nice afternoon? What are you drinking"

Rose almost gushed, "We had a great afternoon. I hope it carries on this evening. Can we have a bottle of white wine to share please?"

Diana prepared an ice bucket, four glasses and a bottle of wine as the foursome sat next to Malcolm and Helen. As she worked, she watched as Malcolm occasionally tugged surreptitiously on the material of Helen`s dress. This would cause it to tighten around her bust and hit the secreted nipple pegs. Helen would wince or bite her lip as the pain spread from the tips of her breasts. To make it even more evil Malcolm would usually do this while Helen was talking with one of the other two couples and she really had to concentrate on maintaining her train of thought, whilst not showing her obvious discomfort. It was apparently a game that they played very often as Helen was quite adept at carrying on a conversation through the agony that Malcolm was inflicting.

Gradually the bar filled up as the others arrived and Diana was kept busy filling their drink orders. Helen must have had five gin and tonics by the time Moira arrived to lead them all through to dinner. Diana had also ensured they were good measures to assist her friend with the pain she must have been enduring. As it was Helen was quite tipsy as she clung to Malcolm`s arm on the way to the dining room.

Diana briskly cleaned up the bar and went to help with the service. Even Dominic was present that evening as his hunger must have got the better of him as he had eaten nearly nothing since he arrived on the island. Ann spent the whole meal playing with his cock underneath the starched tablecloth. He seemed unaffected by this and joined in with the conversation for once.

Anita, Raj, Michael and Rose seemed to be a fixed foursome now as they shared private jokes and giggled together. Bella and Julie seemed in good spirits after their introduction to double penetration the night before, whilst Ian and Deb were also laughing and joining in with the others jokes. All in all it was a very pleasant evening that ended with the customary Sambuca with Moira.

The couples wound their way back to their rooms, or the rooms of their sexual partners for the night. Diana cleared up and helped clean the kitchen with Moira. Due to the late arrival of the supply boat Harry and Greg were still trying to put all of the new food in the large freezer or the pantry. Eventually they were done, and Diana told Harry that she was off to visit Helen and Malcolm. Moira overheard her and whispered to Harry, "I will come to your room for a bit, if you don`t mind?" Diana watched as her husband and Boss left the kitchen together with only one thing on their minds. She wasn`t jealous, and was just happy that they would be having some fun whilst she was with Helen and her husband.

After a quick visit to the bathroom where she adjusted her dress and hair, Diana climbed the staircase to room number one. Diana was excited, as the couple were by far her favourites, as she knocked gently. Malcom`s strong baritone voice told her to, "Enter!"

Walking into the room Diana saw the couple sitting together on the foot of the bed. Helen was smoking, still dressed in the yellow dress, but she had released her hair from the hairpins that had held it up at dinner and now her blonde hair cascaded down around her shoulders.

Malcolm was naked and Helen was running her fingers up and down his impressive length. He was fully erect and Diana once more marvelled at his impressive manhood.

Helen smiled at Diana and through a mouthful of smoke told her, "Hi Diana. Come here and help me get him off quickly. Once he has come, we can have some fun while he recovers and then he can ream us both all evening.

"Sounds like a plan," replied Diana as she sat on the Malcolm`s other side, "Hands or mouths?" she asked Helen.

"I think both may be necessary my dear. He did come in the bar, but he is very excited after teasing me all evening. You suck and I will use my hand if you don`t mind?"

Diana bent at the waist and took the large purple head of Malcolm`s dick in her mouth as Helen ran her fingers up the stiff nine inches of her husband`s penis. As Diana enveloped the head in her warm mouth Malcolm exhaled loudly. "Very good Diana," he said before adding, "A little more tongue movement if you please!" Diana obliged by flicking her tongue over the tip and the small slit at its peak and drew another satisfied moan from the older man.

As she sucked on him Helen increased the speed of her hand movements without ever stopping puffing on her cigarette. Within a few minutes Malcolm was blowing hard and then erupted into Diana`s mouth, filling it with creamy delicious tasting spunk. As Diana licked him clean Helen stubbed out her cigarette in an ashrtray that was resting on the bedcovers. She rose from the bed before easing the straps of her dress off of her shoulders and let it fall to the ground.

Helen stepped out of the dress and stood looking at Diana in just the pale-yellow panties and her four-inch stiletto heels of black patent leather. Diana stared at the woman. She was in her fifties but had looked after herself, that was for sure. Yes, there were signs of aging, but putting all things together she had the figure of a woman in her early thirties. Diana was somewhat enamoured with this dignified woman. The pegs glinting on each nipple somehow intensified her sensuality.

Diana stood. With practiced hands she released the clasp at the back of her dress and let gravity pull it to the floor. She had chosen her favourite underwear for the evening as if she knew she would be spending it with this gorgeous creature. Her lingerie set was all black with small red flowers sown into the cups of the bra and the front of the tanga panties. The tanga exposed her taut buttocks that still showed the bruises inflicted by Ann. She heard Malcolm take a sharp intake of breath as he cast his eyes over the results of Ann`s riding crop.

The garter belt holding up sheer smoky grey stockings matched the bra and panties with the small red flowers stitched around the belt. She too was wearing heels of more than four inches, but Helen still towered over her. Diana stood looking at Helen and waited for her to make the next move.

Helen turned her back to Diana and seductively placed a thumb on each side of her panties and then bent perfectly at the waist as she pulled them down to her ankles. Diana stifled a gasp as she saw the older woman's buttocks were criss-crossed with deep welts that were turning every colour of the rainbow. Helen had been very naughty this week it would seem, as she had received multiple strokes of Malcolm`s cane on the milky white skin of her behind. In the middle of the bruising Diana saw the glint of the emerald-coloured stone that was set in the steel base of an anal plug buried deep in her anus.

Diana instinctively reached out a hand and let it trail over the bruised flesh and then let her fingers gingerly run over the emerald-coloured stone. Helen whimpered softly at her touch before straightening her body, stepping gracefully out of the panties and turning to face Diana. Diana ran her eyes over the toned stomach muscles, taking in the whips of greyish blonde hair on her pubis and the bright red, bruised and clamped clitoris at its apex. The lips of Helen`s pussy were engorged and glistening with arousal.

Helen smiled at the younger girl's reaction and said sexily, and with just a hint of expectancy, "You can do whatever you want with me, but under no circumstances must you remove the pegs and the anal plug. Understood?"

Diana could only nod at the strange request. She watched as Helen lay down next to her husband on the bed. Diana could resist no longer and lay on top of her. Her own bra clad breasts rubbing against the pegs on Helen`s nipples causing the older woman to flinch, whilst moaning softly her undeniable pleasure at the contact.

Diana kissed her passionately, the taste of nicotine strong on Helen`s lips. Normally this was a mood killer for Diana, but with Helen it just seemed more of an aphrodisiac. The two women kissed, their tongues fighting a fencing match in their mouths as their hands explored each other's bodies. Diana enjoyed every touch as Helen manipulated her nipples through the thin gauze of the bra. Helen pinched them and flicked them with her fingers until they were hard as granite and rubbing painfully against the translucent material.

Diana's hands were also busy running with the lightest of touches over Helen`s breasts and tortured nipples. Every contact with the small silver pegs was met with a shudder and a moan of complete satisfaction and acute stimulation.

Diana buried her head into Helen`s shoulder as strong thin fingers found their way under the waist band of her panties and a fingernail ran over her erect clitoris. Diana let the glorious sensations wash over her as Helen worked upon her clit. Her touch was at one time rough and then gentle; fingertips replaced by raking fingernails.

Diana was swept along in a sexual torrent and her climax erupted as Helen guided two fingers into her dripping pussy whilst her thumb pressed down with power on her clit. Diana clamped her teeth to the shoulder blade of this woman who was sending these delicious waves of pleasure through her body. She bit her so hard she nearly drew blood, such was the power of her orgasm. When Helen withdrew her hand there was a deep feeling of a void as Diana tried to regulate her breathing before she tried to repay this marvellous orgasm.

Diana let her hand trail down over the ever so slightly wrinkled tummy muscles and Helen shivered at her touch. Slowly, slowly her hand edged downwards until it hit the small peg on Helen`s clit. The woman exploded underneath her. She shrieked loudly as she bucked hard against Diana`s body. Her climax was intense, and goosebumps covered her skin, the small fair hairs on her arms stood up as tremors passed through her body. She was still experiencing minor after shocks as her second orgasm arrived as Diana slipped two fingers past the small peg and into a vagina that was literally dripping with excitement. Diana held Helen tightly as the woman lay shuddering violently beneath her. Once she had calmed Diana released her and slipped down her body.

Diana gently eased Helen`s legs apart using the woman`s knees. Sliding between her legs Diana poked out her tongue and gathered the sweet tasting nectar that coated the enflamed lips of the woman's pussy. Every touch of her tongue brought a reflexive shiver from Helen, and she soon had climax number three when Diana mischievously flicked the silver peg with her tongue. As her orgasm subsided Helen reached down and breathlessly begged, "No more Diana. Please. No more! I cannot take anymore, but I want to taste your delicious honey pot. Please, sit on me so that I can taste you!"

Diana kissed her way up Helen`s shivering body and then knelt either side of her head. Her stockinged thighs rubbing against Helen`s cheeks and upper arms. Diana felt Helen sucking the moisture from the soaked gusset of her panties before one of her fingers manoeuvred it to one side allowing Helen`s tongue access to her gash.

Helen attacked Diana with ferocity. Her tongue seemed to be touching every part of Diana`s sex at once. Her teeth gnawed on her clit until Diana bucked hard and screamed her orgasm to the ceiling, her head flew back, and her eyes rolled in their sockets. Still there was no relief as Helen added two fingers to the mix, aggressively fingering the younger woman until she came once more with a shriek that could have woken the entire hotel. Only now did she let Diana relax.

Both women lay panting in a post coital haze when a stern voice commanded them, "Diana, I am ready again. Be a good girl and grab that tube of lubricant from the nightstand. Helen has been begging me all week to analise her and tonight is the night.!"

On Bambi like legs Diana staggered to the nightstand. Locating the large tube of lube, she crawled onto the bed. "If you could lube me up that would be greatly appreciated," Malcolm ordered her in his gruff voice.

Diana squirted a large dollop of the cold slimy gel into her hand. She had to use both hand to liberally coat Malcolm`s huge, rock hard dick. Once she was finished, she watched in awe as he eased the plug from Helen`s backside. The plug had been buried within her for several hours and her anus gaped wide after its removal.

Malcolm pressed the tube and a large amount of the gel landed directly in the centre of Helen`s gaping back passage. With two fingers Malcolm expertly massaged the gel in, and widened the hole.

When all was ready, he lay back on the bed and Helen positioned herself squatting above him facing his feet. Using her thighs, and after placing the tip of his dick against the entrance to her anal passage, she lowered herself gingerly onto his stiff rod. There was a brief grimace as the bulbous, purple head pushed past the muscles at the entrance and then he was in her, and she slid inch by inch down his slick pole as Diana watched amazed. It took over a minute, but eventually his entire nine inches were hidden from view in Helen`s dark tunnel.

Helen took several deep breaths before gyrating on the stiff dick invading her arse. Only when she was completely composed did Malcolm place one hand under each of her buttocks and move her up and down, allowing half his considerable length to leave her body before she again recaptured it as he let her fall.

Diana figured that she wasn`t there to just watch so she scrabbled around in front of Helen, and between Malcolm`s legs. She watched spellbound as the couple copulated. Malcolm`s long dick appearing from, and the disappearing into his wife`s arse. Diana could see that both were close to coming and tried to expedite that event. One hand cupped Malcolm`s large testicles as with the other she ran her fingers over the vacant pussy of his wife before running them with the gentlest touches over Helen`s bruised and pinched clit. This caused Helen to climax violently and Diana could physically see her anal muscles contract to such a point that Malcolm struggled to reenter her. The added pressure on his dick and Diana massaging his balls resulted in Malcolm screaming, "I`m coming Darling!" as his body spasmed and he ejaculated deep within Helen`s rectum.

Malcolm lifted his wife from his come covered dick and laid her tenderly on the bed before pulling him to his chest in a tight embrace. Helen was whimpering softly as her thin arm grasped him around the waist and Malcolm bent his head slightly and placed the most tender of kisses on the top of her blonde hair that was splayed out over his chest.

Diana started to leave so as not to intrude on an obviously intense romantic moment for the couple when Malcolm stopped her, "Please don't go Diana. We just need a minute. Please stay. We both so enjoy your company." Diana sat back down on the bed and watched as the couple hugged and stroked each other. She could see there was a genuine love in this marriage even if it was a bit kinky with all the spankings and S & M things.

Five minutes passed before Helen disentangled herself from her husband`s embrace. Crawling slowly, she moved towards Diana before kissing her passionately,her tongue pushing urgently into the younger girls mouth and Diana felt herself responding to the familiar taste of gin and nicotine. While they were kissing Malcolm silently went to the bathroom and Diana heard the shower start as Helen broke their kiss, pulled a cigarette from her packet before lighting it and leaning back as she blew the smoke to the ceiling. "Do you want one Darling?" Helen asked Diana with her eyes closed. "It is so nice to have a ciggie after a resounding good fuck from my gorgeous husband!"