Rich Man's Pleasure Pt. 01

I am a 27-year-old rich man, and I bought a 20-year-old woman to give me sexual pleasure. I know that makes me sound like a creep, but it's entirely consensual. Sam isn't dumb; she knows why I bought her cunt and why she allows me to have free use of her body. But this isn't some master/slave thing or even any kind of normal contract. Anything goes too far, Sam knows she can trust me enough to tell me. She knows I won't just abandon her if she doesn't do everything I want. She gets to buy anything she wants, gets to spend unlimited time on hobbies, doesn't have to work, and her college education is paid. It helps that she also gets off on being a nympho. It works because we make it work. Anyone who doesn't like our relationship, our kinks, or how we talk and refer to each other can go fuck themselves.

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My name is John. I was 26 when I won the lottery. After taxes and such, I paid off what my parents still owed on their house and one of their cars. They can now afford to go on some nice vacations. I bought my sister and her fiancé a house as an early wedding gift. I also bought lavish gifts for my two best friends. The pretenders and the distant relatives suddenly contacted me of course, but I didn't care so long as the people I was closest with were taken care of.

After that, I had about 10 million left over. I bought myself a million-dollar house on a twenty-three-acre lot. It has 4 bedrooms with large closets, 4 bathrooms, an office, open kitchen and living room area, an upstairs game room with a good-sized balcony, a big back yard, built in below ground pool, large patio and grill space, a firepit, and many mature trees on the property. I also bought myself a $50,000 dollar truck.

I placed a couple million into bank accounts as my fall back that I wouldn't spend unless I had to. I put some of my money into stock investments. Then I used a little under 2 million to buy houses in a few different college towns that I turned into rent houses. As the owner of the rent houses, I got a nice nest egg from the college students renting them, and since they were in the biggest college towns in the state there were always more students willing to rent. Soon, I was making back more than the amount of what I actually spend day-to-day, which isn't as much as the spending sprees make it seem. This amount doesn't include spending on hobbies, impulse buying, or what I would later on spend on my woman. That is where the last couple million that I had in other savings accounts came in what I call my spending accounts.

A year passed while I lived my new life. I used money spending accounts on some nice vacations. For the daily stuff like gas and food I used what I got from owning the rent houses and my stock investments. I used some of the spending accounts to still be generous with my immediate family and best friends, and I gave thousands each month to charities that support soldiers, first responders, and children without parent(s). I no longer worked except for managing my rent houses so I travelled more, found new hobbies, and spent more time with my real friends and my family.

For the most part, I enjoyed my new life. Being rich was a lot of fun.

One thing I did want though, was a woman. I was never really good at relationships. I had my share of them, but the longest I had lasted less than a year. A part of me liked just being on my own. In a relationship, a person always has to consider what their other half wants too. Not that it's a bad thing. However, I liked to eat out where I wanted to, do the hobbies that interested me without having to check in with someone, watching what I wanted to on TV, do my chores and house projects when I felt like doing them, and so on. I was always kind of introverted in that way. I never found a woman that just clicked perfectly into my life style.

One evening while watching porn, a title caught my eye: "Rich old man and gold-digging stepdaughter." That title got my mind going and the next day I started looking up different sites on the computer. The first few searches yielded either porn or bots, but I finally found a site I wanted. It was a mix between an OnlyFans and a dating sight for sugar daddies/babies. The concept may have crossed some moral lines for some people, but it was all legal. Basically, men on these sites buy gifts for the girls and take them on dates; in exchange the girls would send gifts to the men in the form of pictures or videos and the dates would lead to sex.

I knew I would have to do some more searching to find the right girl for what I wanted, so I looked under the girls who were new to the site. A 20-year-old named Sam caught my attention. She had crimson hair that was too dark to be her natural hair color. She had a half sleeve of tattoos from shoulder to elbow on her right arm and she was working on a half sleeve on her left arm. She had another tattoo on her collarbone and a couple on her legs. Her breasts were size B. Her ass was firm but not big. Her figure was slim and not too petite. She had dark eyes and light skin. In her profile picture she wore a black lace bra and panties that displayed all of this except of course the look of her nipples and her pussy.

Sam wanted money for college, but she wouldn't just accept any man. She wanted a good fucking if she was going to be a rich man's toy. Her bio also listed what turned her on and off, some basic interests, where she would like to go on dates, and a note that her schedule had to still revolve around college classes and personal time during this new adventure.

After a bit of messaging back and forth, Sam agreed to meet me for a lunch interview of sorts at an Italian restaurant the next day. When Sam arrived, she was wearing a spaghetti strap top and a skirt that went down to mid-thigh. The outfit displayed Sam's tattoos. It also showed off a lot of the skin that she was trying to sell me.

I am also inked, so naturally the conversation started with our tattoos. By the time we stopped talking about the art on our bodies and the interests that inspired us to get them, the breadsticks and salad were gone. As we waited for our main dish, I had grilled shrimp and angel hair pasta and she had chicken alfredo, Sam reiterated what she said online about college being her priority.

"Maybe we should get more formal about this, then," I suggested. "How far are you willing to go in this pursuit. Please, be honest."

"I don't know yet, John," she answered. "I never thought about doing this kind of job till recently. You are my first customer, so I won't know until..." Sam trailed off.

I smiled at her. I whispered, "Until I'm fucking you."

Sam turned beat red.

"How about this, I'll pay you for this date and for your current semester of college. If you can't continue after that, then at least this experiment was worth your time."

Her eyes lit up. She was about to open her mouth to say something, but our food arrived. After thanking the handsome waiter, we started to eat. It was several minutes before Sam asked, "You would really pay for my whole semester just for one date?" She put air quotes around "date."

"Sam, this is kind of an experiment for me too. Like I told you in the message chat, I haven't been in a relationship in a while and having money means in the back of my mind I'm always going to wonder if the girl is in it for my dough. Paying up front means that I know exactly what this is. What I still want to know is if I can have a passionate sexual relationship with a woman I'm paying. The reason I'm being so generous with this is because I may decide I can't do another time, and I want it to be valuable to you just in case." I doubted that I would want to stop after one time, but Sam needed to know that the possibility was there and that I wasn't going to snatch away this extra incentive if she could only do this once.

"How do I know you'll actually give me what you say?"

Here came the proposal. "Because I have ten thousand in my truck and on my person. I'm confident that you wont rob me of it because of two reasons, I'm only going to give you half upfront. Also, there will be more money after that. I will give you ten thousand dollars twice a month for your services starting on the first of next month, which is five days from now. I will also give you gifts and take you on expensive dates. There are three catches to our unofficial contract. One: you and I are exclusive, so no other men and you delete that profile you have on the site. Two: in front of family and friends on both our sides, we pretend to be boyfriend and girlfriend. We don't tell anyone what our relationship actually is unless we both agree to tell them on an individual basis. Three: we both have lives outside of sex, so I will never force you to come get fucked. But no ghosting or blowing me off. If you are too busy or its your time of the month or you just aren't having a good day, tell me honestly. I won't force you to fuck me, but trying to make excuses all the time instead of just telling me is bullshit best left out. It goes both ways, by the way. Don't think you have to wait for me to call you up. If you want to fuck, come over."

Sam had become more and more stunned, and I think turned on as I gave her my pitch. She nodded and verbally agreed to all of it. To show her I was serious, I gave her the first thousand under the table.

As we were finishing up our meal, I heard a clatter. Sam had dropped her fork. "Could you get that for me?" she asked, giving me a wink.

I got under the table and was treated to the sight of her open legs. She had pulled her skirt up and pulled her panties to one side. The sight of her pussy, shown off without any asking on my part had my cock twitching.

"I think it's time you and I put our words to actions," I told her when I came up without her fork. Sam giggled and agreed. I settled the bill with the waiter, leaving him a 30% tip.

As we were leaving, I brought up a map of the nearby lake on my phone and showed her a spot. "Do you know how to get here?"

"Yeah, my parents and I used to camp and hike around the lake all the time. I didn't bring proper shoes or clothes to hike in though."

I gave her a grin. "I like spending time in the woods and one of the park rangers is a friend of mine. That trail is currently closed, and the entrance is blocked off. There was a big rockslide on it a few weeks ago that hasn't been cleared yet. Mike gave me a key to unlock the gate."

Sam took my meaning, but hesitated. "You're a stranger taking me to an isolated location to have your way with me. What if it goes further? You could hurt me, kill me, or rape me way out there." Before I could protest, she lifted her phone up and took my picture. "I'm also going to take a picture of your truck, license, license plate, and the place we are going and text it to my friend. I won't tell her about our arrangement of course. As far as she'll know its just a normal date. And I'll tell her to delete the pictures after."

I understood her precaution. I walked Sam to her car after she had her pictures, then gave her one more instruction.

I was in the parking lot at the base of the closed trail first. We had it all to ourselves because of the gate. When she arrived, I had already set up a blanket and a couple of pillows in the bed of my truck. I had taken off my jeans and left them in the truck. As Sam approached my truck, I was glad to see she had followed my instructions about taking off her bra. Her nipples poking through her top as she swayed toward me. Her knowing what I wanted her for, caused a tent to form in my boxer briefs.

Sam reached my tailgate and saw I was already getting erect. She stared at my tent with hesitation and wondering if she should continue written across her face.

I got up and sat on the tailgate. "If you don't want to do this, we can stop right here. I won't make you give me back the cash. I won't make you go further than you want. At this moment or any point along the way you want to stop, just say it."

"I just..." Sam shook her head not knowing how to say it. "John, I love sex. I like being experimental with sex. I even had a free use thing going with an ex-roommate not that long ago. But I wonder if I'm taking this too far."

I remained silent and let her work it out.

"I'm not bothered by the fact that you purchased my body for your sexual pleasure. It even turns me on a bit that out of the women on that site, you wanted me. Isn't that supposed to be wrong, though? Shouldn't the idea of a man buying my body twist my face and give me a feeling of disgust? I should want to slap you and cuss you out. Instead..."

Sam stopped rambling to herself and made up her mind. She kissed me full on the lips. In seconds, our mouths had opened to each other, and our tongues began their exploration. My hands began to explore her body. I was glad when I put one hand under her skirt and felt that she had removed her panties too. As my fingers touched her slit, she exhaled. She broke the kiss and gave me a look of exhilaration. We moved to the front of the truck bed where the blanket and pillows were. My shirt and briefs were off and pushed aside. She had her shirt off exposing her bare nipples to the fresh air. Before she took off her skirt, she saw my hard on out in the open. She leaned in and took my cock in her mouth.

A few minutes later, I pulled her into my lap. Then, I looked into her eyes as she lowered herself onto my stiff cock. As my cock entered her, her mouth opened in a moan. My hands explored her ass and tits. As I went between them, I stopped at her hips and removed her skirt. By then, we had a good rhythm going as I thrusted up into her as she descended. Sam leaned into me and nibbled at my neck. As I squeezed her ass again, she let out a deep moan.

It didn't last long, though. I whispered to her as she her teeth bit at my earlobe. "I'm sorry, Sam. It's too soon, but... I'm about to--" I started to lift her off me.

Sam cut me off. "No! Inside me, John!"

I granted her request three thrusts later as I came inside the pussy I just paid for. After we slowed down, Sam rested her head into my shoulder and waited for my cock to soften inside her pussy till it fell out.

"So, where do we go from here?" Sam asked.

"What do you mean?" I asked while lazily rubbing one of her breasts.

"I mean that you've bought me and had me, so... will this continue?"

"You've definitely earned your money. You have a great body that I would gladly fuck again. Ultimately, though, whether or not I continue to buy your pussy is up to you."

Sam stayed quiet. I let her mull it over in her head. After several long minutes, she said, "I never thought I would do this kind of thing till recently. Now that I've done it, I don't feel ashamed like I thought I would."

"Then, let's continue. Tonight," I responded. "I'll give you my address and we'll do a trial run of you staying the night."

The next morning, when I awoke, Sam was sucking my cock. Waking up to a blowjob felt almost as good as being inside of a tight pussy. It also showed me something that I needed to know. Sam took my cock in her mouth without any prompting from me. If she was having second thoughts about her role, they were disappearing quickly. My doubts about if she liked being a rich man's personal fuck toy were also disappearing. If she didn't like being my slut, then she wouldn't have woken me. She would have tried to delay my waking up as long as possible to avoid my cock inside her. Also, if she thought that waking me up would have just gotten it over faster, then she would have just gotten me up and taken my dick inside her till I came rather than giving me pleasure with her mouth. My excitement from these revelations in my head lead to Sam on her back being fucked missionary. As the morning sun filled the room along with her cries of pleasure, we climaxed. I rested my head on her breasts as my cum leaked out of her. She ran her hands through my hair. Her breathing steadied and she said, "That was even better than last night!"

Last night, Sam arrived at my house as the sun went down. She brought an overnight bag with changes of clothes, toiletries, makeup, and sexy lingerie. She wore a cute dress with a thong underneath. She didn't wear it for long. I had Sam strip for me and stay nude throughout the tour of the house. I showed her most of the first floor. However, watching her sexy naked ass sway up the stairs was too much to resist. We entered the game room. I took Sam over to the snack bar in one corner. There I bent my slut over the counter and fucked her till I was ready to burst. I put her on her knees and my cum shot into her mouth and onto her face.

She spent the rest of the tour with my cum on her. I gave her a towel from one of the bathrooms to clean up, then I rewarded my pleasure girl by putting her on the bed, spreading her legs, and eating her out.

Sam and I continued our relationship for a month before anyone else was told about it. Of course, as we had discussed beforehand, our families and friends wouldn't be told the circumstances of our free use fucking. As far as they were concerned, we were dating. I found myself enjoying spending time with Sam beyond the sex. Sam and I discovered we had many of the same tastes with tv shows and movies. We each picked a show to start watching together. Hers was an anime: Fullmetal Alchemist Brotherhood. Mine was Battlestar Galactica. Sam likes to cosplay too. She showed off several to me one day, and while she was changing them in front of me, I resisted the urge to fuck her. That is until she spotted my tent and sucked me off while being Kita from Atlantis the Lost Empire. She made Tiktok videos centered around cosplay and I bought her materials to make more cosplay and higher quality videos. We both enjoyed reading and would lose ourselves in my ever-expanding library that I turned one of the bedrooms into.

Beyond the nerdy hobbies, we both liked to hike and camp in the woods and lake near the town we lived in. Being away from some of the light pollution of the town, I started buying telescopes and learning about the constellations. That one didn't interest Sam as much, but she liked doing things in the cool night air like swimming or cooking over a firepit. Sam showed me her sketches and drawings and I showed her my own art hobby: woodcarving. She liked shooting guns and wasn't weirded out by my prepper habits.

I didn't like the idea of her having an OnlyFans at first, but she explained that she liked showing off her body. She also reminded me that our agreement was that no other man could fuck her; not that no other man could see her nudes. The day after I learned about her OnlyFans, I subscribed to it. I quickly understood the appeal. With her page, she got to express herself in a way she couldn't in public or on Tiktok. She got gratification from men and women whom she would never meet. She loved that they were so into her naked body even though they would never have it. I found an unknown kink of mine too when seeing the comments. All those men and women wanted to fuck her, but she belonged to me. She was my girl, and they would never know the joy I got from being inside her.

Sam and I also continued our sexual relationship how it began. I still paid for her sexy body and used it to meet my needs. Twice a month not including gifts or dates, I paid her for being my slut.