“What would it involve?” I asked, turned on by the secrecy of the situation.
“You’d travel down to Grand Cayman, met by a chauffeur and taken to his private house that’s very secluded. He would meet you there. Then you’d be his possession for the week. You know, the usual stuff, nothing kinky unless you’re OK with it. His house has a private beach where you can sunbathe in the nude and he’d be willing to take you diving on his own yacht. How about it?”
Since I’d made so much money I’d been thinking of going to Florida with my friends for spring break, but this sounded too good to be true. A week in a tropical paradise and a lot of fucking. I just wished I knew who it was. I hoped it was one of the men that I didn’t have to work too hard with to cum.
“And the same rules apply as normal?” I asked Suzy.
“Every single one.”
“I’ll do it,” I smiled.
“You won’t regret it.”
To my friends I said that I’d been invited to go on vacation with my cousins. To my family I said I was going to Cancun with my friends. On the first day of spring break I boarded a plane to Grand Cayman. My patron obviously wanted me to arrive happy and rested since he’d bought me a first class ticket. I didn’t have to wait for my luggage since I travelled very light. I realised that I wasn’t expecting to wear a lot of clothes so I’d only packed the essentials. I was met by a chauffeur and when I reached the house a butler showed me to a bedroom. He showed me that there was a note for me in an envelope and I went to read it.
“Dear Roxie,” it said. “Put some sunscreen on your lovely body and go relax by the pool. The staff has been instructed to stay away from there so you’ll have complete privacy. Be careful to put a lot of sunscreen on your tits and pussy as they’ll burn easily. I’ll be back soon and I can’t wait to fuck you.”
It wasn’t signed. I didn’t recognise the handwriting, but then my patrons weren’t in the habit of corresponding with me. I did as I was told and went out into the afternoon sun. I’d never sunbathed in the nude before, but I loved it. It felt decadent and I was starting to feel horny. I couldn’t wait to fuck my secret patron when he got back. I must have nodded off because I didn’t hear any steps. I woke with a start when I felt a hand cupping one of my tits. I opened my eyes and looked into Big Ray’s smiling face.
“Surprise!” he smiled.
“Big Ray,” I exclaimed. “I was hoping it’d be you.”
“I know. I’ve seen the way you’ve been looking at me. I’ve missed you too.”
“Why did you never book me?”
“Maybe because absence makes the heart grow fonder? I knew that if I booked you to dance for me I’d have to fuck you. You were a great fuck when I took your virginity, but if I’m not fucking a virgin I want a woman with experience. I know from Suzy that you’ve fucked many men by now and I also know that she’s had great reports on your progress. I decided it was time for us to fuck again.”
I knew I should have been enraged, but I was so horny and hungry for his cock that I didn’t care. I started caressing his crotch.
“Oh babe,” he laughed. “You’ve turned into such a slut. I bet I could have you for next to nothing if I tried.”
I didn’t admit that he was right. “Just fuck me, Big Ray.” I begged him.
He stopped laughing and looked at me. “Now, babe, you know I can’t wait to be inside your delicious cunt again, but there are rules. I pay for you. That means that I call the shots and you do as I say. I will fuck you when I want to fuck you, but you’re here to please me, not the other way around. Are we clear?”
I felt humiliated. “Crystal.”
“Good! Now take my clothes off and bathe me before we get down to business.”
I pulled his business suit off and folded it on the deck chair. Ever so often he’d pull me close to him and kiss me. He showed me the way to the luxurious bathroom, passing through the bedroom where I’d changed earlier. All my things had been put away. There was a steaming Jacuzzi waiting for us in the bathroom. We stepped inside and I got straight to work on Big Ray. I’d learnt a lot since our last meeting and I could tell that he appreciated what I was doing. When his entire body was clean I breathed deeply and dove under the water and sucked his cock into my mouth. I cleaned him with my tongue and played with his balls for a long time until I had to go up for air. Big Ray grabbed hold of me as I filled my lungs with oxygen.
“I like your initiative. You’ve deserved a good fuck. We got out of the bath and I dried myself and then I towelled off Big Ray. I climbed up on my hands and knees on the bed and Big Ray laughed. “You remembered! You’re a great slut, one of the best I’ve ever had.”
I could hear him putting a condom on his shaft and then he shoved himself deep inside me. I moaned out with pleasure as I once again felt his shaft filling my tight cunt completely. I could tell from Big Ray’s grunt that he wasn’t disappointed in me. As he was fucking me I felt him reaching for something and then I felt a squirt of something cold on my ass. It was lube. Big Ray was fucking my cunt hard and he started massaging my asshole with his fingers. He finally shoved his thumb all the way inside my ass and I screamed out as this gave me my first orgasm. He kept pumping my cunt until I was done cumming and then he pulled out. I knew what was coming and I wasn’t disappointed. Big Ray pulled his thumb out of my ass and little by little he started entering my virgin ass with his big shaft.
The size of him in my ass was beyond belief. I could feel myself burning as soon as his entire cockhead was inside. He gently started pushing himself inside, occasionally pulling out a bit and then shoving himself deeper. I knew I should hurt, but the depravity of the situation turned me on like nothing before. When he was deep inside me he came to a stop, pulled me up by my tits and kissed my neck.
“Now I start fucking your ass,” he whispered to me. True to his word he started pulling out and then slamming inside again. I’d wondered how I’d feel about ass fucking and now I knew. I loved it. It was difficult to stay relaxed so I didn’t hurt, but I managed for most of the time. And when I felt pain it didn’t bother me. The pain was part of the submission of the ass fuck. I loved it. I soon felt Big Ray reach around and start finger fucking my cunt. I was literally on fire. I didn’t think fucking could get any better than it was right then. I finally gave in to the pleasure and as I was squirting my cum juices into Big Ray’s hand he shoved himself all the way up my ass, pulled me tight and I could feel his cock twitching inside me as he shot his load.
He pulled out slowly and we lay down on the bed. “Suck me, babe,” he commanded and I did as I was told. This time there was no 69 as he laid back and enjoyed the view of me deep throating his cock. After a while he reached for another condom and asked me to put it on him so that I could ride him. I came three times while riding him and I was absolutely exhausted by the time he grinned and let his own load shoot.
That week Big Ray owned me. He fucked me everywhere possible. Most days I never bothered putting any clothes on. As if by magic, everywhere we went was cleaned up after us, but I never saw any of the staff in the house. Big Ray kept setting me challenges and I kept meeting them. Every position he requested I delivered. He was insatiable and I loved his appetite. On the fifth evening he said he had a meeting.
“You can choose, babe,” he told me. “I can bring my guest here and you can keep us company, or I meet him in town.”
I knew it was a test. “Bring him here,” I said. Big Ray smiled at me and went and got ready. I showered and dried my hair. I could hear voices on the deck and went out to join Big Ray and his guest. I’d put on a miniscule bathing suit that didn’t leave anything to the imagination.
“Roxie, this is Tom,” Big Ray said. “Tom, this is my Roxie.”
Tom pulled me close and kissed me. “What a pleasure to meet you, my dear.”
I didn’t say much through dinner as Big Ray and Tom were busy talking business. When the dessert plates had been emptied Big Ray looked over at me. “Why don’t you slip out of that thing and then help Tom get undressed?”
I did as I was told. Tom’s erection was already all there as I pulled of the last garment. I looked at Big Ray and he nodded. I sucked Tom’s cock into my mouth and started performing my tongue tricks on him. By my fifth deep throat he couldn’t hold back and shot his load down my throat. I swallowed it and then let go of his cock and kissed him on the lips. By this time Big Ray was naked too and we all went to the bedroom. I sucked Tom and got him hard again. Big Ray was licking my pussy and ass as I serviced his guest. He then gave me a condom to put on Tom and he wrapped one around his own shaft.
“Ride him,” he told me and I straddled Tom’s hips. He was smaller than Big Ray, but he still filled my cunt big time. Big Ray pushed me down with one hand and used the other to squirt lube all over my ass. I knew what was coming. He’d fucked my ass several times in the last week and every time it was an extremely tight fit, but that was nothing to when he double penetrated me. Only a thin wall separated Big Ray and Tom’s cocks as they slid in and out of me. I entered an orgasmic frenzy. I couldn’t stop cumming. By the time the men shot their loads I had no strength left in my body. They pulled out of me, showered and got dressed, leaving me on the bed like a rag doll.
A couple of hours later the meeting must’ve been over. I heard Tom say goodbye and Big Ray came back to the bedroom. “Thank you Roxie. You’ve earned a bonus. I managed to negotiate a much better deal after you fucked Tom.”
I don’t know where he slept that night, but in the early morning he came back to me with a full erection and fucked me hard. It was our last full day and he couldn’t get enough of my cunt, mouth or ass.
When I returned from spring break, with a full body tan that received many compliments at the club, Suzy approached me again.
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