Cassandra’s Gift
Chapter 25
Occasionally I liked to go back to the mainland and I planned to take Natalie with me this time; I’d made dinner reservations at an expensive restaurant. Melissa really wanted to come too and I let her act as chauffeur as long as she dressed up in the uniform and wore the cap. The skipper and her crew got the boat ready and we cast off Friday morning.
It was an easy, relaxing trip. As we got closer to the mainland, the girls put on clothes so as not to attract any attention.
I had a garage near the docks where I kept a car. Melissa got into her chauffeurs uniform and went to pick up the car while Natalie and I got dressed. I put on a suit and tie, pretty standard stuff for a guy, but Natalie looked stunning. She was wearing a long black dress, cut so low in the back that you could see the top of her ass and low in the front to show off her tits. Her body looked fit and tanned and it was obvious there weren’t any tan lines on her body.
Her blonde hair was up and around her neck she wore a black choker with a large, deep blue diamond at the front.
When we got back up on deck, we saw a black SUV with darkly tinted windows waiting for us. As we walked towards it, Melissa got out and gave Natalie a wolf whistle. She held the door open and Natalie and I got in. As we drove along I slipped my hand under her dress to caress her tits and pinch her nipples.
The restaurant was on the harbour with a small park next to it. Natalie and I went inside while Melissa sat down on a bench in the park.
We were shown to the best table in the place, next to the window with an unrestricted view of the harbour and city skyline, lit up brightly this time of night.
Men stopped what they were doing to look at Natalie as she walked past. More than one wife had to nudge her husband to get his attention.
We ordered food and wine and were enjoying the meal when Natalie said “I think this place needs some fun and games.”
“Really?” I said turning to watch a waiter approach a nearby table with two bowls of soup. He placed them on the table and pulled out his cock. He dipped it in the wife’s soup the brought it to her mouth. She hungrily licked his cock and this cycle repeated until the waiter was ready to orgasm. He shot his cum into her soup then moved off, leaving her to enjoy her meal.
Next to us, a waitress sat on a table, removed her panties and spread legs wide. She picked up each of the oysters in the couple’s entree and shoved them up her pussy. She lay back and let the man and woman retrieve the oysters with their tongues.
There’s always one guy who makes a big show of ordering and tasting wine, often sending back the first bottle as unsuitable. This time, when his wine order arrived, the waiter had an empty soft drink bottle and he took out his cock and pissed into it.
He presented the bottle to the connoisseur who studied it and indicated his satisfaction. The waiter poured a small amount into the glass and the man swirled it around and inhaled the bouquet. He took a small sip and swished it around in his mouth, before gesturing for the waiter to fill their glasses. They finished off the bottle, smug at their choice of expensive wine.
One couple had been particularly obnoxious, treating the staff like they were crap. Two waiters approached them and gave each a long handled teaspoon. The waiters dropped their pants and bent over presenting their asses. The couple took the spoons and dug into the waiters’ assholes, pulling out a spoonful of shit and eating it. Enjoying the taste, they kept going back for more.
True love is a great thing to see. A man had just proposed to his girlfriend and she squealed in delight as he pushed the ring into her finger. They leaned into kiss which became long and passionate. He started caressing her tits through her clothes before ripping open her blouse exposing them to the restaurant. He bent her over the table, raised her skirt then fucked her from behind while rest of the patrons clapped them. I had both of them cum with a moan and everyone else cheered.
The staff remembered a good night with lots of tips. The guests remembered everything, but their minds wouldn’t accept it. Try as they could, the images stayed with them.
Natalie and I had finished our meal and enjoyed both the food and the show. Melissa, unfortunately, didn’t get to see it, but Natalie would recount it in great detail later.
We left the restaurant and walked towards the car. Melissa noticed us and got out to open the door for us. As I bent to get in the car, I saw a naked woman sitting in the middle of the back seat. I straighten up and looked back at Melissa who just raised her eyebrows and smiled at me. I said nothing, but let Natalie get into this side of the car, and I got in the other side, the strange woman between us. She looked at Natalie, then to me then to Melissa as she got in the drivers seat.
“So, Melissa,” I said. “Who’s your friend?”
“This is Claire,” she replied. I looked Claire up and down, she had a slim body, tits slightly on the small side and a shaved pussy.
“Hello, Claire,” I said to her.
“Hello, sir,” she replied.
I looked back at Melissa waiting for an explanation. “Claire is a waitress here. She saw me sitting alone on the bench waiting for you and brought me a plate of food on her break. When her shift was over, I was still here and we got to talking. We really liked each other and started kissing. One thing led to another and, well, here we are,” she shrugged.
“I’m happy that you kept yourself busy while we were having dinner,” I said, “but why is Claire currently sitting naked in my car?”
Melon explained: “She’s down on her luck. She moved to this city to try and get into acting, you know how hard that is. She got a few small parts, but didn’t really get anywhere and has had to support herself with waitressing and other odd jobs.”
“Pretty typical story,” I said.
“Yes,” Melissa said, and continued “she decided that film making was more interesting and has been working her way through college for the last few years but it’s expensive and she’s behind on her fees and rent. They kicked her out her apartment last week and they’re about to kick her out of school. This is her last day as a waitresses here; they’re scaling back for the slow season and she was the last on so she’s the first off.”
I turned to address Claire, “Where have you been sleeping?”
“I spent a couple of nights at the YWCA and a friend has been letting me sleep on her couch.”
“What do you do for work?”
“Waitressing mostly, but I also do modelling if I can find work. Nude modelling pays best, either for life drawing classes or photographers. One photographer likes to take bondage shots and pays more for them. I’ve helped out on a couple of porno movies, really just acting as a gopher. It’s hard finding work to fit in around school.”
“What are your options?”
“Waitressing, prostitution or porn movies, but none of them pay well as there’s a lot of girls around willing to do it.”
“And you’re hoping that I’ll pay your way? What are you offering in exchange?”
“No, sir,” she said. “I need food and somewhere to live, but I’ll keep working to pay for college. I’ve seen the marks on Melissa’s body, and the piercings. I’m offering you my body in exchange. ”
“And what’s your sexual preference?”
“I enjoy sex with men sometimes, but I prefer woman.”
I glanced over at Natalie who nodded. Obviously she was interested and I knew Melissa wanted Claire.
“You do realise that we live many hours from here,” I said. “You wouldn’t be able to live with us and still attend college.” From her crestfallen reaction, I guess that had slipped Melissa’s mind in her excitement.
“Does your college offer a distance learning option?” I continued. “Would that be ok with you?”
“Yes, sir, they do. I can do almost everything as a distance student,” she said, brightening up.
“Good,” I replied. “Here’s what I propose: you’ll spend the week with me, Natalie and Melissa here in town. I’ll take care of your immediate college expenses. You can leave at any time during the week and I’ll give you enough money to last a month. If you stay, I expect total obedience and the use of your body in any way I choose; you probably won’t like some of the things I do. After the week is up, we’re heading back home and you can choose to come with us or not. Our home is remote, so your options to leave will be limited—basically you’re committing to staying with us for at least six months to a year. I’ll pay your college expenses while you’re with us and you’ll have plenty of time to do your course work. This is not a free ride, you will earn every cent. Do you accept?”
Claire looked up at Melissa, who reached down and took her hand.
“Yes, sir, I accept.”
“Good, then lets see how well you suck cocks.” I undid my pants and she bent down to suck me. Natalie pulled her hands back and held her wrists together. With her free hand, Natalie ran her hands down to Claire’s pussy and inserted two fingers, working them in and out.
No matter how willing they were, I liked to give the girls a little incentive and conditioning, so when I came in Claire’s mouth, I made her have a powerful orgasm as well.
“Melissa, take us back to the apartment.”
“Yes, sir!” she replied happily.
I’d kept the apartment block, but had rented out the lower four floors, keeping the penthouse and roof terrace for myself. I could have left it empty, but figured it’d attracted less attention if there were people coming and going all the time, rather than standing empty except for the odd week when we were staying there.
We pulled into the car park and headed up to the penthouse. Claire was still naked and I was a little disappointed that we didn’t run into anyone.
As soon as we stepped out of the lift, Natalie and Melissa removed their clothes. Melissa, at my prompting, fetched three sets of collars and cuffs and gave one set to me while she and Natalie put their own on. I held the collar up to Claire and she, a little nervously, let me fasten it around her neck, then the wrist and ankle cuffs. Having Natalie and Melissa being treated the same eased her fear.
“Claire, Natalie would like some attention from you,” I said. Claire put her arms around Natalie and started kissing her. They both sank to the couch as they continued kissing and fondling each other. Claire eventually worked her way down to Natalie’s pussy and started licking. Melissa moved in and started thrusting a finger in and out of Claire’s asshole. I matched Claire’s level of arousal to Natalie’s and made them cum at the same time.
Natalie got out the Y shaped chain with nipple and clitoris clamps and attached them to Claire, tightening them enough to cause Claire to gasp in pain. I had Claire get down in her hands and knees and Melissa fucked her from behind with a strap on. Claire had another powerful orgasm and lay there recovering.
We moved her to one of the king sized beds and lay her down. Natalie and I kissed, fondled and pinched her tits and nipples, while Melissa push fingers in her pussy and ass while licking her clitoris.
The unusual level of stimulation had her extremely aroused and ready to come in no time, but I wouldn’t let her. I cranked the level of arousal higher and higher until she was zoned out from pleasure, her head lolling to one side. She was shaking and panting when I finally let her cum and I made her orgasm the most intense she’d ever had. I left Melissa there with her and Natalie and I went up to the roof top terrace. I enjoyed the city lights, but they didn’t compare to the stars we could see from the island.
“Push her hard this week,” I told Natalie. “But not so hard she wants to leave.” I’d prefer she came to us willingly, but I’m happy to push her here and there and condition her with orgasms.
Natalie took a swig of her beer and nodded. “Should we pierce her?” she asked.
I thought about it for a few seconds. “Yeah. She seemed receptive to it so let’s pierce her labia. We’ll get Angela to do it.”
In the morning I found Claire standing in the lounge room, her hands pulled above her head and fastened to a loop in the ceiling.
“Good morning, Claire, what are you doing like that?” I asked.
“Good morning, sir. Melissa is going to cane me.” She answered nervously.
“No, Melissa won’t cane you today.” A look of relief passed over her face. “I’ll get Natalie to do it, she’ll be much harder on you than Melissa will.”
She gulped, a touch of fear showing now. “Yes, sir,” she said meekly.
Melissa watched on while Natalie got the cane out and swished it back and forth and aide tensed each time, expecting to be struck. Without warning Natalie made contact across her ass with a loud crack. Claire cried out and Natalie caned her again before she could take another breath. I could see that Natalie was holding back a little, not using her full strength and being careful where she delivered the strokes. She caned Claire’s ass ten times before walked around and laying the cane on one of her tits. Claire was crying and shaking her head, but Natalie ignored her and, with a quick flick, struck her tit with the cane. Claire continued to cry out and plead while Natalie struck each tit five times, avoiding the more sensitive nipples.
It’d been a good first caning, they’d only get more painful from now one.
I’d made her get aroused by it and her pussy was dripping wet. Melissa wrapped her arms around Claire from behind, one hand fondling her tits, the other rubbing her clitoris and pussy until she came.
We released her and she cuddled in the couch with Melissa.
“Claire, were going to pierce your labia today, just like Melissa’s.” Her eyes darted down to Melissa’s pussy then back up. “Ok, sir.” She replied.
“The rings we use are permanent and will need to be cut off if you change your mind.” I explained to her.
She said nothing for a few seconds, then nodded, “Yes, sir.” Melissa leaned over and kissed her.
Angela arrived later that day and had Claire lie back in the dining room table while she put in the piercing. Melissa hovered around offering unnecessary advice on placement, but Angela was a professional and did the job swiftly and without fuss.
Claire got up off the table, the rings tinkling together faintly. There was some pain and it was uncomfortable to sit, so I sent her and Melissa up to the roof terrace to lie down and have a beer. Seeing them lying there, you could see the difference the environment made: Melissa was tanned, fit and healthy; Claire was pale and a bit scrawny and soft. If she came back to the island, that’d soon change.
On Monday, I arranged to pay Claire’s outstanding college fees. She went to class as normal, but started the process of transferring to a distance learning student. She wasn’t allowed to wear panties or bra, and I made her wear a short skirt and a sheer top as a reminder of her new life. I wasn’t sure if this sort of outfit would cause her problems with the guys, so I assigned Natalie as her body guard. She’d drive Claire to and from college, and hang around on campus in case she was needed; her police badge would stop anyone from asking too many questions. I gave Claire a can of police issue pepper spray and a phone with a panic button that would cause Natalie to come running.
I was interested in how she’d react, so I planned to encourage a few guys to take an interest in her later in the week.
Every night she came back to the apartment and we gave her a taste of what to expect. She’d never been fucked in the ass, so we took care of that and made sure she got plenty of experience with it that week.
The caning and clamping continued and she had to give us each a blow job twice a day, morning and night. We slowly ramped up the intensity and pain and I increased her levels of arousal and strength of orgasms to match. She and Melissa slept together every night and I think they were falling deeply in love.
On Thursday, I went to her college and had a group of five guys hassle her at lunch time. They made lewd, suggestive remarks to her and pinched her ass. She couldn’t get them to stop and nobody else was helping, so she pulled out the pepper spray and squirted one of the guys in the face. He staggered around, unable to see while the other guys kept at her. She got one more guy with the spray before the remainder managed to get it off her. She backed away from them and got the phone out, pushing the panic button before they got that away from her too.
They continued to taunt and try to pinch her as she backed away from them. The other students just laughed at what was going on and there was no sign of campus security. As she backed through the outside doors, she turned and ran. She saw Natalie heading towards her and changed direction. Natalie gestured for Claire to get behind her and, panting, she obeyed.
The three guys slowed a little as they saw Natalie standing there but continued to approach. When they were close enough, she whipped her extendable baton open and attacked.
In short order, the three guys were lying on the ground in pain. I’d ordered her not to break any bones and she had, reluctantly, complied.
She checked that Claire was ok and calmed her down. Campus police turned up and she flashed her badge explaining the guys had assaulted Claire. They were cuffed and taken away for questioning.
Natalie ushered her into the car and headed home. Claire had calmed down by the time they got to the penthouse and stripped her clothes off as usual. She down played the incident and praised Natalie’s skill. The next morning, Melissa said she seemed ok and didn’t appear to be traumatised. I faded the in incident of the event from mind until it was only a faint memory.
Friday night came around and Melissa wanted to try dribbling molten wax on Claire’s nipples. By adjusting the height of the candle she could control the amount of pain. Claire managed to put up with the pain no matter how close Melissa got. She eventually had to stop or risk burning her with the flame. She moved the candle and started dripping it on Claire’s clitoris and pussy. She was clearly in pain and whimpering, but didn’t cry out for Melissa to stop. When Melissa finally stopped, she slipped her fingers in Claire’s pussy and asshole and she orgasmed immediately.
It was Saturday morning, and our week with Claire was up. I gathered them around the table and said “Claire, you need to make a decision.”
“Yes, sir,” she replied and I had a good idea of her decision.
“But don’t decide now. Natalie, Melissa and I are going away for the weekend. You’ll have the next two days without us, no collars, cuffs or pain, to do what you want. Stay here, I’ll give you some money, and live a normal life. We’ll be back on Monday morning.” We kissed her goodbye and left her standing there a little bewildered.
We got on the boat and motored up the coast and back. Natalie and I enjoyed ourselves, but Melissa was miserable.
When we stepped out of the elevator and into the penthouse on Monday morning, Claire was there waiting for us, naked, with collar and cuff, Kneeling in the slave position.
“I guess you’ve made your choice,” I said to her.
“Yes, sir.” She replied. With that, Melissa dropped to her knees and hugged and kissed her.
“Ok, pack up and get ready, I want to leave as soon as possible,” I ordered and they scurried to obey. Claire was a little surprised when we pulled up at the dock and got out, but she didn’t say anything. We boarded the boat while Melissa returned the car to its garage and we cast off as soon as she was aboard.
When we were safely away from land, the girls, including the crew, stripped off their clothes. Claire was just beginning to appreciate the number of girls that I had. She was in for more of a shock when we reached the island.
There wasn’t much to do on the trip so Melissa took Claire to her cabin and they didn’t come out until we were within sight of home.
Claire was spellbound at the sight of our beautiful island and was totally overwhelmed to see my entire staff standing naked on the dock to greet us. “Don’t worry,” I told her. “You’ll get to meet each and every one when you lick their pussy.”