My Secret Life

I saw him in the club almost every night I worked and every time he chose a different girl, but never me. He never booked me through Suzy either. I was dying to know why. I got so obsessed by him that I would have fucked him for free if he'd only paid attention to me. When I walked past him on my way to and from other tables he'd smile politely, but the hunger that had been in his eyes before we fucked was now gone. I figured that letting him fuck me had taken away the mystery and he now considered me a wasted cunt, especially since I was fucking every other Tom, Dick and Harry who came to the club.

Then out of the blue I got a phone call from Suzy. She wanted to meet me and discuss a proposition.

"How would you like to make a substantial amount of money during spring break?" she asked me as we sat down on our usual park bench and enjoyed the early spring sun.

"How much?" I asked.

She mentioned an amount that was 10 times what I was paid for one night and mentioned that this job would last a week.

"One of your patrons wants to take you to Grand Cayman for spring break. His wife is going to Disney World with the kids and he wants to have a week long orgy with you."

"Who is it?"

"I can't say. That's the amount he offered and it's non-negotiable. If you say no it'll be offered to another girl, but you were his first choice. I need an answer straight away."

"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.

"Big Ray wants to hire you. He'll pay you a monthly fee, out of which I'll take my commission, and rent you an apartment near campus and he'll pay all your bills. Since he has a family he'll never have time to visit you on Fridays and Saturdays so you can keep dancing at the club on those nights. He'll own your body two nights a week and you'll always know which nights at least two weeks in advance. The other three nights you can use to study or to fuck other men, but you're not allowed to fuck them in his apartment. You'll have to keep meeting them on their premises. He'll contact me about when he needs you and if you have any requests, comments or complaints you bring them up with me. He only wants you happy to see him when you meet. He will let you go home to your family for the holidays, but he wants you to stay in town for most of the summer so tell your family you've got a job. Sometimes he'll want you to come with him on his travels, but he'll arrange that with me and it will only happen when you don't have to be at college, and he wants full access to your schedule to plan these trips. Any questions?"

I thought about it. My roommate had started getting suspicious of my late night work and I'd run out of places to change for my "dates". A place of my own would be perfect. I knew that I could probably afford an apartment with what I was making now, but this sounded more secure. "How long will this arrangement last?"

"Until Big Ray gets tired of you. But between you and me, he's guaranteed me my fee for at least a year so you're safe for that long."

Suzy told me what he was offering me and I knew I couldn't turn it down. Not only did it mean that I'd fuck my favourite cock regularly, but it made me financially independent. I told Suzy that I agreed to the terms and within a week I moved into my own apartment. I told my parents that I was sharing an apartment with some other girls and that we had caller display so that we only ever answered our own calls. I then told them that I wanted to keep working through the summer and they agreed that it was a good idea. They were proud of me. Little did they know that my work involved spreading my legs for an overweight millionaire with a huge cock.

Max wasn't happy to let me go down to two nights, but he raised my rates even more and he was soon making as much out of me two nights a week as he had three. I had a wonderful couple of years. I danced and fucked and even had time to study a little. There was one small hiccup when I nearly failed a course, but I gave my professor some gift vouchers from the club and he was happy for the rest of the year. When I started my senior year my parents told me that my dad's business was doing a lot better again so I could stop working. With my brothers all employed and only me left in college they could afford to give me pocket money and pay my rent (by that time they thought I'd moved again to live on my own), but I declined. I was fiercely independent and proud of making my own way, even though being a professional cock teaser might not be everybody's idea of a suitable career for a girl from suburbia.

A week before my graduation I quit the club and Max was unhappy to see me go. He offered me a partnership to stay dancing on his tables and his guests' laps, but I knew I had to end that chapter of my life. I gave all my regular patrons goodbye fucks and that only left Big Ray. He wanted to keep me. Through the years we'd perfected our fucking to our mutual satisfaction. He'd taken me to Europe and the Caribbean. On a few occasions he'd shared me with other men and even watched other men fuck me. When I told him that I was moving home he wanted to make arrangements to come and fuck me occasionally, wherever I lived, but I didn't tell him. It was time for me to stop fucking around and start my adult life.

I moved home and started teaching second grade in the same school that I'd attended many years ago. I'd saved a lot of the money I'd made during college and was able to buy a small house. My parents thought I had a mortgage and I wasn't going to tell them that I'd bought it with the money I'd made from living out my sexual fantasies. I started dating and I got used to a different kind of sex, which turned out to be just as satisfying. I'd lived out my depraved animalistic tendencies and was happy to try the love thing. A year and a half after leaving my former life my boyfriend, a local architect, proposed to me and I accepted. We got married the following summer and he designed us a dream house to fill with our children. He was a big boy with a big appetite in bed and we were perfectly matched.

The night before our third anniversary my husband disappointed me by saying that he was having to attend a business dinner on our anniversary. I was seven months pregnant with our first child and I didn't want to come along, but the other wives were going and I knew it was important. My husband had just started an architectural partnership and he was going to be successful, as long as the clients kept coming to him. The client this time was a big department store chain that wanted to open shop in our state and needed a dozen stores designed to very particular specifications. It would be a great feather in my husband's hat and secure his income for a good many years.

We were already in the restaurant with my husband's partners and their wives when the CEO of the potential client walked in with a young girl on his arm. My eyes widened in shock as I recognised Big Ray.

"My wife went to college in the same town as your offices," my husband said when he introduced me to Big Ray.

"You don't say?" he pretended not to know me. "Well, you sit next to me Mrs Pritchard and tell me all about it. Maybe we have some common acquaintances."

I was lost for words so I just smiled and took a seat next to Big Ray and left my husband entertaining his escort. Big Ray kept up an inconspicuous conversation for the rest of the table to see, but every now and then he'd whisper in my ears. "Jasmine is nowhere near as good on the table or in bed as you were. Does your husband fuck your ass the way I used to? Are you satisfied with just the one man now or do you still fuck around? I can't tell you how much your pregnant belly is turning me on, I always fancied planting a seed in you myself, but I knew that would ruin what we had."

I smiled politely, but couldn't remember anything I said. My husband got the contract. He was over the moon. "And he's invited us to come and stay in his house in Grand Cayman when the baby's born. I said yes. I know how much you've wanted to go to the Caribbean."

Our son was 6 months old when we went to Grand Cayman. I was still breastfeeding so I couldn't go diving, but everyone else was going. Until Big Ray pulled out at the last minute because of some "emergency" that he had to deal with. I was on the deck, catching the sun when he walked up to me.

"Sweet Roxie," he smiled. "Let's see if that cunt of yours is as tight after childbirth as it used to be when I owned you."

He took me to the bedroom where we'd fucked so many times before. My tits were DD-cups by then and my nipples were darker. I still shaved all over. This time it was Big Ray who "serviced" me. He sucked and licked and bit my pussy and I was every bit as wet as he remembered. When he finally penetrated me, he shouted out in triumph. I'd worked very hard and my cunt was indeed as tight as it had always been. We fucked like old times. Halfway through the day when I had to feed my son he called the boat and arranged for a mechanical fault. We fucked even more. When the sun started to set we knew that we only had time to fuck once more.

"Roxie," Big Ray said softly as my mouth was full of his cock. "You know I'm clean. I know you're clean. Please, as a parting gift, let me fuck you just once without a condom." This was the one thing I'd always missed so I agreed. I was breastfeeding so what could happen?

I lay down on my back, pulled my legs up to open my wet cunt for Big Ray's eyes. "Fuck me, Big Ray. Fuck me one last time and make it one I'll never forget."

He came down on me immediately. His cock slid inside me and I knew that it was going to be the one time I'd always remember. I came and I came and I came and Big Ray kept going. We rolled over and I rode him and came again. Finally he had me up against the wall, my tits in his hands and him pounding me from behind. Then he shot his biggest load all the way up inside my womb. We both screamed out loud from our joint orgasm and we collapsed on the floor. Big Ray ran his finger past my pussy and sucked our combined juices. He then scooped up some more and let me taste. We kissed deeply and then we parted for the last time. We knew we'd never fuck again. It was too risky, and we'd done everything now. It was better to leave it as a good memory.