Prize Island Revisited Pt. 03

Story Info
Diana tutors Anita and is then abused by Ann.
7.1k words
4.44
4.7k
7

Part 10 of the 12 part series

Updated 06/11/2023
Created 04/27/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
ColonelB
ColonelB
246 Followers

This story is part of the Prize Island series, so if you haven`t done so please read that nine part adventure as it will give this story context. Harry and Diana are back on the island, but this time they are working there. Moira is still the boss, and Greg still works in the kitchen. This story has elements of BDSM and punishments so if that is not your thing please read elsewhere. It is also a fantasy and not real. As always, I just write for fun so please feel free to leave constructive criticism, just no rudeness please.

Hope you enjoy it!!!

XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

Part 3

Diana woke to an empty bed. She hadn`t even heard Harry leave as she was in such a deep sleep. After carrying out her morning ablutions and dressing quickly she left the room. She was only a few yards from the annex when she heard distressed sniffles coming from behind one of the ornamental shrubs that lined the path to the main house.

Crying from being punished was normal here, but crying from sadness was a sound that she had never heard on the island, so Diana went to investigate the source. She found Anita sitting on one of the various wooden benches that were dotted around the property. Her eyes were red with tears and a scrunched up tissue was clasped tightly in her hand.

"Whatever's wrong Anita?"

The girl turned those beautiful brown eyes to Diana, "Oh, it`s you Diana. I am so sorry I thought I would be alone here."

Diana sat next to Anita on the bench and put a comforting arm around her shoulder, "Tell me what happened. Why are you crying? The island is supposed to make people happy, not sad."

Anita blew her nose loudly and snuggled deeper into Diana`s body. She took a deep breath and then the words just spilled from her lips like a waterfall, "I am just being silly Diana. It`s Raj. He was so pissed with me when I didn't join in with the...what shall we call it....orgy, at the hot tub yesterday."

Diana thought about it and remembered that while all the others were engaged in various forms of sex Anita had been by herself in the tub. "You didn`t want to?" she enquired quietly.

Anita threw one arm around Diana`s waist and was now speaking into Diana`s breasts as she said, "Yes I did. I was horny as hell, but," there was a pause as Diana felt Anita taking deep breaths to control her small sobs. "I was just embarrassed that I would make a mistake or do the wrong thing. I have only ever slept with Raj so I don`t have that much experience, and absolutely none with women."

Diana was now stroking Anita`s hair gently and this seemed to calm the petite girl in her arms and the sobbing slowed to barely nothing. "Do you want to have sex with a woman Anita? You don`t have to you know? On the island you can do whatever you want. You don`t have to sleep with other people. You can just have the best sex with Raj if that`s what you want."

Anita still had her face immersed in Diana`s breasts and her muffled reply was given vehemently, "That`s the whole point. I want to experiment. I want to make Raj happy. I want to try with a woman and see if I like it. I want to play around with the other men here. I want all of those things but I am just so shy."

Diana hugged the conflicted woman tightly, "Well," she began, "I could help you if you want?"

Anita pulled away and gazed into Diana`s eyes. "How?"

Diana could hardly contain her excitement. She had wanted to fuck Anita from the first moment she saw her, and to find out she was a bi-virgin was even more thrilling. Even though she could already feel her arousal racing she tried to play it cool. "If you want. If you and Raj want. You could maybe come to my room after breakfast and I will guide you through it. Harry will be there as well, so maybe we can kill two birds with one stone, or if you want, he can go and sleep in Moira`s room. We can stop whenever you want. I will answer any questions you may have, but I think that there will not be that many as you can just do what feels good to you. How does that sound?"

Anita reached up and kissed Diana directly on the lips. "You would do that for me Diana? That would be just fantastic. I just need to get my confidence boosted and you seem so calm and tender that I am sure you would be a great teacher......and lover," she ended with a shy grin.

"That´s settled then. But now I really have to get to work. One question though. With or without Harry?"

Anita didn`t think for very long and her grin became much more suggestive as she replied somewhat breathlessly, "Oh Diana. That`s a definite WITH!"

The two girls walked the short path to the hotel. Anita kissed Diana on the cheek before Diana disappeared into the kitchen as Anita walked through the patio doors to find Raj and tell him what she had planned.

In the kitchen Diana pulled Harry to one side and explained what she had arranged with Anita for later. Harry was quite excited at the prospect, as Anita was probably the most natural beauty of all the guests that week.

Diana went about her preparations as the guests started to wander into the dining room. Anita and Raj didn`t appear until at least twenty minutes later and Diana was just starting to worry that Anita`s planned tryst had not gone down well with her husband. However, they entered the room like a whirlwind, arm in arm and giggling loudly. Raj smiled at Diana and gave her an exaggerated wink before they both sat at the table and started to eat.

Breakfast was mostly eaten to a bawdy monologue from Ann about her adventures with Malcolm and Helen that had all the other guests' rapt attention. Apparently Ann had got her wish to deep throat Malcolm`s huge python three times. Every time had cost her eight strokes of the cane, as Helen watched with a vibrator buried in her snatch. At the end of her story Ann announced that, "It was well worth the pain to have such a wonderful specimen of manhood down my throat. His come was like champagne!"

Diana watched Helen. The older woman was quiet throughout Ann`s tale and was squirming in her chair even more than yesterday. Her bad behaviour with the vibrator had had consequences it would seem. Diana wondered how much more punishment the poor woman`s posterior could take, although she did seem insatiable.

When breakfast was finished the guests sat and discussed their plans for the morning. The skies were again overcast and there was some drizzle in the air so all of them decided, at Ann`s direction as always, to have a sauna morning. Gradually they all left to get ready. Diana stopped Anita and whispered in her ear, "Room B in thirty minutes OK?"

Anita nodded and grasped Raj`s hand tighter. Raj just smiled.

Harry, Greg and Diana quickly had the room and kitchen shipshape, and fifteen minutes later Diana and Harry were walking hand in hand down the path to their room. They quickly showered the smell of fried breakfast off of their bodies and out of their hair. They had just left the bathroom wrapped in huge bath towels as there was a timid knock on the door. Harry answered it to find Anita standing outside blushing crimson. She looked fabulous in a yellow sundress that was so short Diana got a brief glimpse of white panties as Anita shuffled self-consciously into the room.

Diana and Harry sat on the bed whilst Anita stood gazing at the floor. Diana tried to break the ice a little by asking, "Raj seemed quite happy with your plan for this morning. No problems?"

Anita smiled shyly and her eyes came up from the floor, "When I got to the room Raj was just finishing in the shower. When I told him what was going to happen we were both so excited. I have never seen him get so hard, so quick. My imagination was going crazy about what might happen and I was so wet that I just pulled his towel off and sucked his cock. When he was close to coming I wanked him off all over my tits. He came so much that they were drenched in his come. Then I had to have a shower of course."

Diana was now in teacher mode, "You didn`t let him finish in your mouth? I heard you say once that you didn`t like that. Am I right?"

Anita`s eye`s again feel to the floor as her self-consciousness returned. "It is not really that I don`t like it. It`s just the thought of it. I have only let him do it once, and that surprised me as he came so quickly and I wasn`t ready, I ended up gagging and spluttering with his spunk coming out of my nose. It was such a horrible experience I never tried again, although Raj begs me to let him constantly."

"Well that is something else we will cure you of this morning. Harry loves to have his cock sucked, and come in my mouth. Plus he has the best tasting come I have ever tasted." They all laughed at Diana`s crudeness and she finished off by saying, "By the time you leave here this morning you will want to swallow Raj`s load every night Anita!"

Now that they were all laughing Diana stood up and let the towel fall from her body. She stood still for a minute and let Anita`s eyes wander over her five foot eleven frame, smallish pert breasts, with hardened pink nipples at the top. Anita looked her up and down like a slave handler in the market. Her eyes lingered on Diana`s freshly shaved mound and then ran lewdly down her long tanned, muscled legs. "Like what you see Anita?" she asked before walking towards the speechless girl and pulling the yellow sundress over her head in one movement.

Anita`s hands instinctively tried to cover her naked breasts as she wasn`t wearing a bra under the dress. Diana gently pulled her hands away and bent forward and sucked one of the hard, dark brown nipples gently into her mouth. She heard Anita gasp and then freeze as Harry rose from the bed and took the other nipple between his lips. The couple continued to suck, lick and bite playfully until Diana felt Anita relaxing.

Diana released the nipple and looked up at Anita who had her eyes closed and was breathing heavily. Diana ran her finger nails over the hard brown nub and kissed Anita carefully waiting for her to respond. As she felt the Indian girl`s lips part slightly she pushed her tongue stealthily between them and was relieved as she felt Anita`s mouth open to accept it and her own tongue edged into Diana`s mouth.

Diana and Anita kissed for several minutes while Diana`s finger nails scratched one of Anita`s nipples with varying force and Harry continued to suck and nibble the other. Diana couldn`t believe it when Anita let out a low moan followed by a loud "Aaaaargh"" as she came just from having her breasts played with. They were apparently hyper sensitive.

Both she and Harry stopped and looked at Anita before Diana asked, "Wow. You love having your breasts played with don`t you? I have never seen anybody get off that quick from just a bit of nipple play!"

Anita again looked bashful, "I am so sorry Diana, but you and Harry just made me feel so good. I have always had sensitive breasts and can usually get myself off by just pinching my nipples."

This gave Diana an idea and she moved to the nightstand and took something from the drawer. Returning to Anita she showed her two small nipple clamps. "I am going to put these on you and you will wear them for the whole session. Hopefully it will just increase your enjoyment." With that she pulled hard on both nipples and fitted the little clamps. Anita let out a small cry and then a low "Aaaah!" as a second smaller orgasm rippled slowly through her body.

Diana knelt and pulled down the small, white, diaphanous panties that Anita was wearing. Anita stepped out of them gracefully. Diana stepped back to admire her work. Anita was still trembling through small aftershocks. Her tiny frame was covered in goose bumps and her long black hair hung down in a shimmering black cascade to the crack of her arse. Her firm smallish breasts stood out proudly from her chest with the small clamps glinting on both her hard dark brown nipples. Her flat muscled stomach ran down to a bush of wiry black hair that had never seen scissors or a razor. There was a flash of pink skin against the brown where her delightful pussy was already opening in anticipation.

Diana took Anita`s chin in the fingers of one hand, pulling her up so that she had to look up at the taller woman. "Anita, we have to take care of that wild bush OK?"

The girl was on such an orgasmic high that she just nodded blankly and offered no resistance as Diana and Harry led her into the bathroom. They lay a large bath towel on the floor and Harry helped Anita lay down as Diana sought and located a pair of nail scissors. Harry`s towel had also fallen off by now and he was sporting a large erection as Diana went to work snipping away Anita`s pubic thatch with the scissors.

Once the majority of the hair was removed Diana used some of Harry`s shaving gel and lathered up a good covering of foam on Anita`s mound before selecting a new lady shave razor from the pack she kept under the sink. In less than a minute Diana was admiring Anita`s newly bald mound. Diana pulled her to her feet and guiding Anita into the shower cabin she sprayed the excess foam away before turning the shower to massage mode, playing the needle-like jets over Anita`s clamped nipples. This had the desired effect and Anita screamed out as her third orgasm of the day wracked her body.

Half carrying the poor girl out of the cabin Diana saw that Harry had removed the hair covered towel from the floor, so Diana got a new one from the rack and gently patted Anita`s body dry. Diana took a good finger full from the pot of La Mer that she had received as a gift from a previous guest, massaging the expensive cream into Anita`s freshly shaved mound. Once finished Diana led Anita back into the bedroom where Harry was laying on the bed and gently stroking his impressive hard on.

Diana positioned Anita on one side of Harry before settling down on his other side. She had placed Anita so her face was directly next to Harry`s erect penis, "Now Anita, it is time for Harry to come. We can fuck him later, but that will be more satisfying if he has already shot his load. We are going to suck him until he comes OK?"

Anita was on such an erotic high after three climax`s in the last thirty minutes that she just nodded. "Now take him in your mouth Anita. Show me what skills you`ve got in the blow job department."

Diana watched as Anita nervously grasped her husband's dick and placed the purple head in her mouth and began to bob up and down furiously, her eyes scrunched shut as if she was eating dirt. Only about half of Harry`s adequate length was entering on every downward movement. "Stop!" said Diana forcibly. "That just will not do. Firstly, you have to do it because you enjoy it, and not as a punishment. Secondly, take your time, plus use your hands and tongue. Thirdly, all men love it when you have all of them in your mouth and not just the half. Here I will show you."

With that Diana leaned across and pulled Harry`s cock towards her. Her tongue poked out and licked all around the mushroom head that was shiny with Anita`s saliva and she also pushed it hard into the slit at the apex. All the time her fingers were running up and down the shaft with the lightest of touches. Once Harry had emitted a low groan under his breath she slowly eased more and more of his length into her mouth until she felt him enter her throat and her nose was tickled by his wiry pubic hair, her tongue was moving frantically inside her mouth and flicking all over Harry`s shaft.

She let him withdraw and passed his cock over to Anita, "Now try again. You saw what I did, now just copy." She watched as Anita tentatively covered Harry`s cock with small licks and kisses, her tongue concentrating on the sensitive slit at the top and being rewarded with another low moan from Harry as his hand grabbed hold of her long, shiny black hair and encouraged her to take him in her mouth. Anita followed his unspoken instructions and opened her mouth wide before sliding his penis in until it was at the same depth she had used earlier. Diana could hear the gargle in her throat where she was struggling to take more. She leaned across and viciously flicked one of the nipple clamps that Anita was wearing.

Anita screamed around Harry`s cock. Diana said evilly, "I will do that every minute until you take him all. Do you understand me?" Anita`s eyes widened and she nodded frantically. Her face was a picture of fear but she never let Harry out of her warm, wet mouth. She raised herself onto her knees in an effort to assist with the task Diana had set her. She managed to take another inch before pulling back and spluttering, her saliva coating Harry`s rock hard dick. Diana flicked the other nipple clamp and Anita shrieked, and then mewled like a cat as orgasm number four hit her.

When she was ready, Anita tried once more and got within an inch of taking Harry`s entire length before again releasing him as she coughed and spluttered, tears coursing down her face. Diana flicked another nipple and Anita pushed downwards with renewed vigour until her nose touched Harry`s pubic hair and then she bounced back and let out a loud, "Yeeees! I did it!"

Diana leaned across Harry`s midriff and pushed her tongue aggressively into Anita`s mouth, and the Indian girl responded equally roughly as they shared a celebratory kiss. While they were kissing Diana took Anita`s hand and encouraged her to move it up and down on Harry`s erection, which she did with glee.

As they broke their kiss Diana announced, "Now is time for the big finale. Are you ready? "Diana saw the doubt cloud the young girls face, but she nodded slowly. "Grasp the shaft and hold the head in your mouth. I know he is close so wank him quickly as you suck hard on the head. If you look in his face you will know when he is about to come and you will be prepared."

Anita did as instructed, her eyes glued to Harry`s face looking for a clue that he was about to shoot in her mouth. She needn't have worried though as within a minute Harry announced loudly, "Don´t stop. Please don`t stop. I am coming, get ready." And his hand grasped the back of her head tightly to hold it in place as his whole body jerked as he shot four large loads of his semen into Anita`s mouth. Anita closed her eyes as she felt the warm, creamy fluid fill her mouth, but she didn`t pull away until Harry released her head and he had stopped twitching. She turned to Diana and opened her mouth so that Diana could see the milky fluid of her husband's come, Anita`s mouth closed and with sparkling eyes and a broad grin she swallowed theatrically.

Diana leaned forward and licked up the last drops of come from Harry`s now flaccid dick. She looked at Anita and asked, "And. How was it? Did you like that? I bet you cannot wait to do that with Raj?"

Anita was beaming as she said rather too loudly, "Fantastic. No, more than fantastic. Yes and yes to all your questions. I cannot believe I have denied myself that for all these years."

"I think you have earned yourself a treat now, don`t you?" Anita smiled in a quizzical way and her brow furrowed before Diana explained, "It`s girl time now, as Harry will need at least twenty minutes break after that. That`s why I shaved you. No girl likes to get a mouthful of hair when she is attending to her partner." With that Diana clambered over Harry and pushed Anita roughly down onto her back before burying her head between the startled girl's thighs.

Anita tasted just as good as Diana had hoped and she slurped deliriously at the pink flesh in the middle of the pale brown. A quick glance up Anita`s body showed her that Harry had again latched onto Anita`s nipples and Diana reaped the reward as Anita came gently and a trickle of liquid dripped onto Diana`s active tongue. Diana was enjoying herself tremendously and was running her tongue over every part of Anita`s pussy, so she was a little bit aggrieved when Anita reached down and pulled her away with a breathless, "Diana please. I just can`t anymore. Let me try to do you please."

ColonelB
ColonelB
246 Followers
12