Prize Island Pt. 06

He found nothing of interest on the terrestrial channels and he had already watched the only movie he wanted to see on the Movie Channel. He wasn`t really in the mood for the porn as he had experienced better sex in the last few days than it could offer him. He thought twice before he selected Channel # 1 and watched for a few minutes as Dave and Sandy walked about getting ready for the evening. Channel # 3 gave him the same result with Jim and Mary moving back and forth from the bathroom. Channel # 4 was much more interesting. Harry felt small pangs of guilt as he watched Moira and Gail on the large TV. Both women were naked and looked absolutely fabulous. He watched them move about the room for a few minutes until he saw Moira`s face cloud over. There was no volume so he could not tell what was being said by either woman, but Moira was obviously annoyed by something Gail had said or done.

This view was reinforced as Gail dropped to her knees and put her head on the floor in front of Moira. He could see Moira talking, but could not hear what she said. Gail moved from her position and crawled into a corner on all fours. In the corner was a strange waist high bench, similar to the old vaulting horse they had used at school. Gail lay across the bench and Moira moved behind her. Harry hadn`t seen where it had come from, but now Moira was holding a riding crop in one hand as she approached Gail.

Harry watched with a kind of sick fascination as Moira brought her arm back before landing ten hard blows with the crop on poor Gail`s behind. Harry couldn't tear his eyes from the screen as Moira moved back to the bed before laying down and spreading her legs wide open. Gail moved from the bench and crawled across the room before settling herself between Moira`s thighs. Harry couldn`t see what she was doing, but he could guess pretty well, as her blonde head began to move up and down. Within minutes Moira was writhing on the bed and pulling Gail`s hair viciously as she had apparently climaxed.

Gail raised her head from between Moira`s legs, before crawling back to the bench and once more prostrating herself. Harry was shocked as he saw a now recovered Moira move behind Gail once more and deliver another ten blows across Gail`s arse with the riding crop.

Harry was so entranced by the action on the screen he had not heard the shower stopping and Diana enter the room and he was startled as he heard her voice come from next to the bed where she had been standing and watching in silence, "Oh my God. That is so hot. I wish I could swap with Gail for just ten minutes!" then she smiled mischievously at Harry as she continued, "Wouldn't my Master like to see Moira put that riding crop against my bum? I think he would judging by that reaction!" and she raised her eyebrows as she stared at Harry`s crotch.

Harry had stripped off his clothes on entering the room and was lying naked on the bed. He peered down at his crotch, following Diana`s eyes, and saw his straining cock sticking up hard and proud. He blushed slightly as he looked at Diana with her wet hair and her body wrapped in a large bath towel. He could only nod like an idiot as Diana seductively continued, "Would my Master like me to take care of his rather large problem? Would he like me to take him in my warm, wet mouth? Maybe to push himself so far in that I nearly gag, as he throat fucks me before filling my mouth with his delicious hot, creamy come?"

Harry`s eyes were nearly bulging as Diana dropped her towel and knelt between his legs. Within seconds Harry felt the wet warmth of her mouth as she nearly swallowed him whole. She was pushing down with such urgency as her tongue swirled over his glans and shaft, that Harry knew watching Moira and Gail had turned or on as much as him, if not more.

Such was her apparent need and his heightened arousal that within minutes he felt himself stiffen as his orgasm approached. He felt Diana gently start to massage his balls and with one last effort she pushed down and Harry felt the tip of his cock enter her throat. He grunted loudly and ejaculated. Diana was swallowing while he was still just about in her throat and this just increased the delightful sensations attacking his cock and he spurted again and again. Harry was amazed as Diana continued to swallow after every spasm. She had allowed his cock to slip out of her throat, but kept the head trapped between her lips as she swallowed his massive deposit one gulp at a time.

Harry felt the spasms stop, but Diana was still sucking him and trying to extract every last drop of his come. Eventually the sensitivity was so intense he had to use his hand to pull himself away from Diana`s voracious lips. He was breathing heavily and his face was creased with pain as she had nearly sucked him dry. He looked down at Diana who was grinning up at him as she pushed one stray dribble of his come back into her mouth with one finger.

Harry was speechless, but was saved from a comment, as he heard a soft knock on the door. Diana sprung up and nearly skipped as she ran to open the door. She was still naked, but that was now normality for them both. She opened the door and took a plastic carrier bag from Gail, who said simply, "Your costumes!" before carrying on to Dave and Mary`s room with a bag probably containing their costumes for the evening.

Diana ushered Harry into the bathroom and followed him in. As he switched on the shower and let the warm water run over his body he heard the hairdryer start. As he stood under the jets his mind wandered to what he had seen in room four. His suspicions were confirmed, he knew that for sure. Moira was a dominant and Gail was her submissive pet. Then his imagination replaced Gail over the bench with his lovely Diana. He felt himself stiffen slightly at the thought. His mind replayed Diana`s comments about trading places and he looked down to see that he was once more fully erect.

This was another thing that puzzled him about their time here. Yes, he was in his prime at twenty five. Yes, he could sometimes manage three erections a day at home in London. However, that was the exception rather than the rule. Normally after two he was done and needed at least a day to recover. Here he was getting four, five and even six boners a day. He willed his dick to deflate as he thought to himself, "Long may it continue!"

The hairdryer was still running as Harry managed to will his erection away and finished washing himself. Harry stepped from the shower at the exact moment that Diana switched off the hairdryer. He gazed over at her with love, and he conceded, more than a little lust. He always loved to watch her get ready for their rare nights out together. When she washed and styled her hair to frame her beautiful face and applied just enough makeup to highlight her best facial features, she always managed to look so damn sexy when she was finished, and Harry couldn`t imagine being partnered with anyone else more delightful.

Diana noticed him staring and smiled coyly as she wrapped the towel around her once more, before going into the bedroom and issuing a short command as she went, "Shave!"

Harry ran hot water into the basin and lathered his face with shaving gel. Slowly and deliberately he removed all the stubble from his face. He knew that Diana loved it when he was freshly shaved and she always complained if he went down on her with a day or twos growth as she said it irritated her skin. "Guess I will be eating pussy tonight," he silently grinned to himself as he washed away the residue of the shaving gel. He brushed his teeth and then liberally applied aftershave and deodorant. Finished with his preparations he entered the room to find Diana sitting at the vanity and applying her makeup.

Harry wandered over to the bed where Diana had placed the carrier bag that Gail had given her. He started to remove the items. Diana`s costume was obviously to be a slutty school girl. There was a white blouse and a red and black striped tie. A mini skirt in red and black plaid. More interestingly for him were the packet of black stockings and a black suspender belt. He also noticed there was no bra or panties and so presumed Diana would wear her own.

Then he saw his costume and didn`t know whether to laugh or cry. There were only two pieces. An old school teacher's smock with holes for his arms and a ridiculously small, black man pouch thing. The pouch was tight as he pulled it up his legs and he literally had to push his genitals into it and waggle them about until he was comfortable. Once he was done he looked at himself in the mirror and saw that the pouch left little to the imagination. Well at least he knew how this evening was intended to play out. That`s for sure!

Diana was giggling as she watched his discomfort in the mirror. She nearly poked her eye out with her mascara brush as she was laughing so much. As Harry slipped the robe around him she purred, "Sexy baby! If you get excited in that, your knob will stick out of the waistband!"

Harry didn`t have a funny reply, so just settled for, "Wait until you see what you have to wear!"

Diana was finished now with her makeup and went to see what she had for a costume. She put on the blouse without a bra. It must have been one or two sizes smaller than what she normally wore as it clung to her body like a second skin. It was so tight that she could only fasten the bottom two buttons and so her compressed breasts were pushed up and her fabulous cleavage was there for all to see.

Harry watched as she clipped the garter belt around her waist. She took the stockings out of the pack and rolled each one up her legs whilst grinning at him seductively. She adjusted the straps on the suspender belt until the six straps were at the correct length, before she clipped them to the stocking tops. Once this was done she pulled on the short pleated skirt. Harry saw that it was indeed short and her stocking tops were easily visible and if she sat down the entire room would have a glorious view of her shaved mons.

Harry was slightly taken a back as she donned Gail`s high heels and announced herself ready, without putting on any panties. Diana must have realised what Harry meant as he looked at her quizzically and just shrugged and said, "Look. We both know they would be coming off sooner or later, so why bother!" Harry knew that she was 99% correct so just nodded.

Linking arms they descended the stairs and walked into the dining room. The large table was gone and there was a large door open in the far wall that must lead to the Great Hall. They walked inside and both gasped loudly at the same time.

The Great Hall was truly beautiful and traditionally decked out. On the wooden panelled walls were four large stuffed stag`s heads and three sets of crossed claymores and two or three paintings of men and women in traditional Scottish dress. This was not the cause of Harry and Diana`s gasps though. In the middle of the room were four old style school desks set up and facing a large desk at the end of the room. On the desk was seated Moira, She had her legs crossed and was sipping a glass of red wine. Moira was dressed in a similar cloak to Harry, but instead of his pouch she was wearing boots of black leather. They came to about two inches above her knee and had amazing five inch stiletto heels. She was wearing no panties or bra and only black stockings and a suspender belt similar to that which Diana was wearing.

Harry gazed at her breasts with her already hardened nipples, and the small landing strip of reddish brown hair that directed Harry`s eyes towards her hidden pussy. To complete the sexy head mistress look Harry saw on the desk next to where she sat, the cane that she had lent him.

Tearing his eyes away from this glorious vision Harry saw that their usual dining room table had been pulled into the Hall. It was filled with finger food and snacks. Bowls of fruit and a huge cheese board with about ten lumps of different cheese. A silver platter with cold cuts of beef, chicken and ham took centre stage. There were crackers and fresh bread in baskets, and the requisite peanuts, crisps and olives in bowls. One end of the table was filled with bottles of wine. The white wine and some champagne was in a big metal tub filled with ice and for some reason Harry focused on the condensation that covered the sides.

Along the other wall, opposite the table of food, were three large red leather sofas. They were in the old style with the leather held in place by a multitude of round headed brass tacks.

Harry had just finished taking in everything the room had to offer as he heard Dave and Sandy enter with Mary and Jim. They were dressed the same as Diana and him. Sandy looked great in her school girl uniform and Dave had obviously been given a larger pouch as it managed to hide his massive dick.

Mary had struggled to push her large boobs into the blouse she had been given and Harry thought it must be quite painful to have those glorious tits so compressed. Her larger bottom had caused her skirt to sit higher than the others and her trimmed black pubic hairs were already visible for all to see.

Gail arrived mere seconds after Jim and Mary. She was also dressed in the school girl uniform and Harry immediately felt himself start to harden as he replayed her spanking from earlier. Harry thought she looked great. Her smallish breasts were pushing at the tight material of the transparent blouse she was wearing. Harry could just make out her two nipples rings through the thin material. Her skirt was very short and her stocking tops were just below the hem.

After the five new arrivals had had time to take in their surroundings Moira coughed to get their attention. Once they were all quiet and looking in her direction she began to speak.

"Welcome to St. McKinnon's School for Girls. I am Head Mistress Moira. I hope you enjoy yourselves here. There is ample food and wine here, and there are sofas provided for the schoolmasters, Dave, Jim and Harry to provide individual tuition for the girls. This tuition may be done in pairs or larger groups, should that be needed. Should anyone be particularly naughty they will be sent to me for disciplining!" At this she theatrically swung the cane through the air. "Now let the fun begin!" she nearly shouted as she raised her glass to toast them.

They all started to help themselves to snacks and wine from the table and Harry stood next to Diana while he nibbled on some cheese and crackers and took large gulps out of his glass of white wine. He knew this was supposed to be an orgy, he wasn`t that naive, but he wasn`t sure how to act. He had never been to an orgy before and it wasn`t really the kind of thing that your parents told you about when they did the "Birds & Bees" talk. As he gazed around the room he got the feeling that all the others were thinking the same as him. They were all chatting easily, as they had done since they first met, but there was definitely a different atmosphere this evening.

Harry was nervous. He knew that once it all got started he would be OK with it. That realisation actually made him briefly question again their actions on the island. He had no problem to fuck in front of the others. He had done so on numerous occasions this week. However, this time felt forced, whereas the other times were sort of spontaneous. He drank more wine than usual as he tried to calm his nerves and soon had a healthy buzz going.

Someone had switched on some music and the CD was obviously old disco hits as "La freak" started to play. Harry thought about dancing to relieve some of the tension he was feeling, but when he turned to ask Diana he found that she was no longer by his side. Making a quick scan of the room he located her talking to Moira. He watched as Diana stood before the Scottish woman, who was still perched on the desk. Diana had her hands clasped in front of her crotch and her head bowed. Harry remembered this submissive pose from their role plays and watched with interest to see how it would play out.

Moira was talking, although Harry couldn`t hear what she was saying, but Diana was nodding furiously to what she was being told. Harry wasn´t surprised, and that surprised him, when Moira spread her legs wide and Diana dropped to her knees before burying her face between Moira`s thighs. Harry was seriously hard now and the tight pouch was causing severe distress to his circulation. He swept his eyes around the room quickly and saw five other pairs of eyes all looking in the same direction. Diana was eating Moira`s pussy with gusto. Harry continued to watch, and felt the tip of his cock push past the waistband of his pouch and escape from the constriction of the ridiculously small pants.

He was startled as he heard Mary speak softly into his ear. "Harry, you seem to have had a major wardrobe malfunction. Rather than leave it out there in the cold, maybe you would like to put your lovely cock somewhere naughty and very warm!" With that she walked a couple of paces in front of him and lifted up her skirt and gave him a tantalizing view of the butt plug between her arse cheeks. He glanced once more at Diana, who was still lapping at Moira`s gash like a dog, and then followed Mary as she walked towards one of the sofas.

Mary had a small handbag with her and she pulled a bottle of lube from it. She handed it to Harry and then bent over the arm of the sofa, flipping her skirt up onto her lower back as she did this. Harry felt enormous relief as he hastily stripped off the miniscule and restrictive pouch and his rampant hard on sprung into view.

He watched spellbound as Mary reached behind her and waggled the butt plug about, before it eventually was pulled from her back passage. The hole that it left was very inviting to Harry and he snapped out of his trance. He poured a copious amount of lube into Mary`s gaping anus, before rubbing it in using two fingers and finger fucking her arse. He got an immediate response as Mary started to purr like a cat and push her arse backwards, encouraging his fingers deeper.

Another quick glance saw Diana still in place, but now Moira was clearly in the throes of an orgasm, as her booted and stockinged legs had Diana`s head clamped between her thighs, and her hands were gripping Diana`s hair and pushing her face into her crotch. Harry could just make out Diana`s small head movements as she continued to pleasure Moira throughout her climax.

As he had watched his wife he had been absently finger fucking Mary`s arse, but now he turned to look at her and saw she was looking over her shoulder at him expectantly. Harry wasted no time in covering his now painfully hard dick with lube. He positioned himself so the tip of his dick replaced the two fingers he had used to prepare her for his anal invasion.

He pushed with both his hips whilst guiding himself with his hand. He had expected the same resistance that he had felt with Diana, but Mary was obviously an experienced annalist, and after only two or three rocking motions he found himself nearly enveloped in her rectum.

Mary let out a low,"Aaaah," as he settled inside her. These "Aaah," became louder and longer as Harry started to pump her arse. She was pushing back hard on every inwards stroke and trying to up the tempo. As this was only Harry`s second arse he was going carefully, but apparently Mary wanted him to speed up, and so he did.

He was gripping hard on her hips now and really ramming himself in and out of her backside. She felt so good and he was loving the feeling of her anal passage constricting his cock as he thrust in and out at speed. Mary was obviously enjoying it as well as she continually chided him, "Faster. Harder. Faster. Harder!"

Harry was close to coming and concentrating hard on prolonging the experience. Not just for himself, but Mary also, as he could sense that she was close to her climax. His concentration was broken as he heard a loud thwack and shriek from the direction he had last seen Moira and Diana.