Olivia's Story

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Olivia does Vegas with boss, his friend and a hooker.
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Hi, I'm Olivia, and to paraphrase Huck Finn, "You don't know about me without you have read a story by the name of 'An Unlikely Threesome,' or 'Marie's Continued Schooling'; but that ain't no matter. Those stories was told by Mr. Bill Sullivan, and he told the truth, mainly. There was things which he stretched, but mainly he told the truth."

I thought I would give Bill a break and take up the continuing story of me, Bill and Marie. A fresh perspective and all.

First, a couple of things about Bill which he neglected to tell you. To start with he is wealthy, like "fuck you" wealthy. I don't think he is a billionaire, but not too far from it. He wasn't born to it, he had a normal, middle class job and existence up until his great uncle died and left him a boatload of money. That was Cyril, his grandmother's brother. Cyril was President of the largest railroad in the U.S., and that was back when railroads were pretty important. He was able to amass a ton of railroad stock, and added considerable money to that, maybe through underhanded dealings of various stripes, you know, the way people sometimes get rich. On the other hand, maybe not, since from all Bill tells me Cyril was a pretty good guy; he never married and had no children. He took to Bill when Bill was quite young, kind of like another grandfather. At any rate, when Cy died, Bill inherited a bit over $200 million.

Another thing you should know about Bill, he is smart as hell, and personable. Not the most handsome guy in the world, you wouldn't look at him twice in a crowd, but you wouldn't turn away from him either. He was something of a health nut, and kept himself in trim shape. Bill was 23 when he came into those millions, he invested most of it in real estate, shopping malls, apartment buildings and such. And he turned that original inheritance into a much larger pile. That's Bill's job now, managing all that stuff, though he has a couple of dozen people working for him. We now lived together, with Marie, in the penthouse of a building he owned in a middle sized city on the East coast of the U.S.

I met Bill a few years after he became rich and a year or so after he and Marie, to whom he was married, split up. I was eating dinner with a married girlfriend at a pretty nice restaurant, we were celebrating something or another. There was a guy by himself eating at the table next to ours. Actually, he wasn't eating yet, he had ordered a meal and was waiting for it to come while sipping on a glass of red wine when I noticed him. He kept looking our way, and I wasn't really surprised when he picked up his glass of wine and came to our table.

"I know this could be an imposition, but it really is a bit lonely for me eating here by myself. Is anything more sad than that? So, if you would allow me to join you for dinner, I promise to behave, and I will pick up the tab."

My girlfriend and I looked at each other, each of us thinking, "sure, he must be looking for something more than our company for dinner." But, he did seem nice, and polite, and we were planning on an expensive meal. So, for better or for worse, we invited him to join us.

And it really, really turned out for the better. That meal was a delight, the conversation was great, it was like we were old friends right from the beginning. We laughed a lot, drank a lot of wine, and left together after Bill picked up the $500 plus tab. At some point during the meal, Bill gave us each a business card with his name and phone number. It indicated he did some kind of IT work. In the parking lot, Bill got into an old pickup truck and my girlfriend and I got into our vehicles and we all drove off.

For the next few days, I couldn't stop thinking about that meal we shared. Men found me attractive, I'm not going to get into describing my looks to you, look at Bill's story "an unlikely threesome," he does a pretty good job there. I was not used to being in the company of a single, straight, man for any length of time and not having that man make at least a mild attempt to get into my pants. And yet, there was not even a hint of that during the dinner I shared with Bill.

So, Bill was on my mind and I finally decided to be really forward and call him; I thought I would invent some kind of problem with my desktop computer. I was a little nervous as I held the phone waiting for him to accept the call.

"Hello, this is Bill Sullivan"

"Hi Bill, this is Olivia, from dinner a couple of nights ago, do you remember me?"

"Sure, how are you Olivia?"

"Pretty good, but I'm having problems with my computer, your card says you are an IT guy, I was hoping maybe...."

"Sure, I could come by and have a look. Just give me an address."

So I did and we set a time for the next evening for him to drop by.

Now you should know something about me; I am sexually adventurous, some might say promiscuous. But, although that lifestyle led to a lot of pleasure, it also was beginning to seem rather empty to me; missing something important. I found myself more and more wanting a better relationship with a man (or maybe a woman, more on that later). It was the easy, steady companionship I craved. I noticed a lot of older couples I knew seemed to have that, and I thought, "why not me." But so far, that has escaped me. I had been thinking for awhile now that my approach to sex might have something to do with this; I was the ultimate "fucks on the first date, " girl. And I had always thought; why not, I enjoyed the sex immensely, why deny myself that. But it just seemed that I was hooking up with one asshole after another.

Bottom line: I promised myself I was going to do things differently with Bill. We had only shared a couple of hours over a meal and wine, but that brief time made me think that there were possibilities with him. So, sad to say, no pussy for you, Bill, at least for a while. Now, could I actually hold out? We would see.

I found myself in a bit of a quandary when getting dressed the evening Bill was coming to "fix" my computer (I had loosened the wire that led to the keyboard, so he would have something to fix.) Normally, I would be dressing in my sexiest attire in this kind of situation. But remembering my promise to myself to take it slower this time, I dialed that back considerably. A tight tee shirt and jeans seemed to strike the right balance. I wanted him to be interested, but not to the point of trying to rip off my clothes.

The doorbell rang and I greeted Bill: "Thanks for coming, I have never been good at this computer stuff, I'm really glad you gave me your card."

"Hey, no problem, let me take a look; what are the symptoms?"

"Well, the damn thing starts up but when I try to use the keyboard, nothing; the mouse still works."

"OK, could be a driver issue, where is it?"

I led him to the spare room I used as an office and he began to fool around with the computer. It took him about a minute to examine the back of the device and find the loose wire. He connected that firmly and the problem was solved, much to my "surprise."

At least I tried to act surprised, and somewhat abashed. "I can't believe it was something so simple and I couldn't figure it out. What do I owe you?"

"For this? Nothing at all."

"Well, at least let me cook you dinner, I was going to prepare pasta and a salad, no problem to cook a little more."

He agreed to that, and we enjoyed our second, very pleasant meal, complete with two bottles of wine.

Bill didn't try anything of a sexual nature that night, but he did ask to see me again.

We went on several more dates and usually ended up back at his apartment afterward. Now let me say that, at this point, I did not know that Bill was wealthy. He had a middle class apartment complex with middle class furnishings and drove a middle class vehicle.

Back to the progress of our relationship, by the third date, he was definitely trying to fuck me, but I was holding out. I was getting to know him and was really liking what I discovered, I think he felt the same about me. I wasn't quite ready to take the next step yet.

So, on maybe our fifth date we were again back at his apartment, making out on the sofa. He had my tits out and was playing with them, sucking the nipples and enjoying it quite a bit, from all indications. So was I, it was hard to keep holding out. I was actually feeling a little sorry for him when I noticed the bulge in his pants. I thought, I better give him a little something or he might lose interest altogether. So I reached down to his lap while he was sucking on my tits. Through his pants, I began stroking his cock. He undid his belt and kind of scooted his pants partially down, freeing up his hard on. Reaching into his underwear I freed the beast and started stroking it. Spitting on my hand to make the whole operation a little slicker proved to be a good move and it wasn't long afterwards that Bill started groaning and shot a pretty big load of cum all over the place, including covering my hand.

"That was great, but when are you going to fuck me?"

"Sure, that's all you want, pussy, just like every other guy."

I was looking into Bill's eyes as I said this and wondering what I was going to do with all the cum drenching my right hand.

Bill just looked hurt upon hearing what I said to him.

"If that's really what every other guy wants, then I definitely am not like them. Yes, I want to fuck you, who wouldn't? But to say that is ALL I want is where you are wrong. I have been so damned lonely for a long time now. I want someone to share life with. Last year I was in Cardiff, Wales and London. In Cardiff I walked to the cathedral at Landreth to see where one of my ancestors served as bishop several hundred years ago. In London I stood in Westminster Abbey among the bones of all the historic English Kings and Queens. I took a trip to Stonehenge and was awestruck trying to imagine the people who built that. And what I was thinking the whole time was that this trip wasn't what I expected. Great as it was, without someone to share these experiences and feelings with, it was considerably diminished. I was hoping you could be that person"

He couldn't have said anything more perfect than that. And I believed it, totally, he was so sincere. If I hadn't just drained his balls I would be fucking him right then and there. I told him that. And that cum on my hand; instead of going into the bathroom to wash it off, I slowly raised my hand to my lips and sucked every drop off of every finger; all the while looking directly at Bill as I swallowed.

"Bill, we are going to be seeing each other in a couple of days, I will give you everything I have that evening."

And I did. Bill told that story already, so I am not going to repeat it or elaborate. Because, as I said at the beginning, he got most everything right. The one exception being he was off on the timing of Marie's entrance into this menage. He made it seem it was nearly contemporaneous with our first fuck. In fact, it happened several months later, after I had already moved into his penthouse.

Speaking of which, we had been seeing each other for several months when one day he pulled up to my place in a brand new BMW 760, still had the temporary tags on it.

"What the fuck, Bill, where's your truck?"

"Just get in, all will be clear soon."

He drove us downtown and pulled into the underground garage of one of the newer residential high rises. After parking the car, he led me to an elevator and produced a key which was required to enter and activate the elevator. When we pulled up to the building I noticed it was pretty tall, probably 25 or 30 floors. So, I expected to see the usual array of buttons. But there was only one, marked PH. Bill pressed that button and we emerged a minute or so into an ultra modern and ultra posh apartment. The furnishings were all obviously first class, and one wall was entirely glass, giving a spectacular view of the city.

"What's this Bill, whose apartment are you bringing me to?"

"Mine."

"No, I've been in your apartment many times, and this is, shall we say, a couple of notches above."

"I'm sorry Olivia, I was not being real with you the past few months, I am actually quite wealthy."

"What? Not real, why?"

"Being rich is mostly great, but there is at least one aspect that isn't so great. Almost all the good friends I have now are people I knew from before I had money. It is really hard to make friends when you are rich; so many people are after something from you that you have to be suspicious of everybody. The friends I have from before, I don't have that concern with them. Imagine trying to find a life partner under those circumstances? All the gold diggers you have to contend with, and never truly knowing if someone wants you for what you are or for what you have. So, I took an apartment in one of the buildings I own, furnished it modestly, bought an aging pickup truck and became Joe average. I didn't see another way to be sure about any relationship I would form. I apologize for being somewhat dishonest with you, but I didn't see any other way. But now I want you to move in here with me and I'm really hoping you will say yes."

"Yes, yes, yes. And I would have moved into your "fake" apartment if you had asked. Though I admit I like this one just a teensy bit better."

I was smiling when I said that, and couldn't stop smiling for the rest of that night; probably even later when I was asleep. And more because we were going to be living together than where we would be living, though that was nice too.

We had been living in the penthouse for about two months when that whole thing with Marie started. Bill's ex wife, ex because she had been unfaithful. But that's another part of the story already told by Bill, which I am not going to repeat.

Marie had been living with us for about a month and things were going surprisingly well. I liked her and she liked me, we all liked each other and got along well. For Bill and me it was starting to go beyond "like." Maybe for Marie and me and Marie and Bill also. The whole thing was a little unusual, but it seemed to be working for us, at least at this point.

I had been putting in some effort to try to get to know Marie as more than a sex partner. She was complicated. Submissive in all things sexual, at least in the sense that she was eager to do anything we wanted. But she could also have strong opinions, and stand up for them, outside the bedroom.

One problem with our little threesome was the lingering effects of Marie's unfaithfulness. I could tell that Bill was still hurt and troubled by this. I had suggested a way that Marie could atone: taking center stage in a bukkake. I had started to formulate a plan to actually pull this off. And I sensed Marie would do it, maybe even like it. She had become a cum slut. Remarkable, since not too long ago she couldn't stand the thought of a man coming in her mouth, or anywhere on her body. Now she and I were almost at the point of fighting over Bill's cum. Fighting is too strong a word, but it seemed every time we had a group fuck, she wanted Bill to cum in her mouth. I was going to have to talk to her about this.

But about the bukkake; Bill didn't want to do it. He was beginning to see Marie in a different light, coming nearer to forgiveness I think. In my mind, the bukkake wasn't off the table completely; but for now it was a no go.

We were all committed to working on this threesome relationship. We knew we had a good thing going but also realized the many pitfalls, emotional and otherwise, that could crop up.

We agreed that communication was a key ingredient for making this work for the long term. To that end we had started what we called "story time." We would take turns telling each other stories about ourselves, as a way to get to know each other better. We did this about twice a week, though there was no rigid schedule. The only rules were: 1. The story had to be about ourselves, the teller, and 2. The story had to be true. Sometimes the stories covered previous sexual experiences one or the other of us had, but just as often they would deal with other topics.

Tonight was my turn and this is the story I told as Bill and Marie got comfortable on the sofa opposite my chair. And when we knew the story would involve sex, getting comfortable meant minimal clothing as the audience often became, shall we say, stimulated.

I was 19 years old at the time this happened. Already more sexually experienced than a lot of women 10 years older than me, but still eager and willing to learn, to sharpen my technique you might say. That summer, to help pay for college, I took a job at one of the larger banks in town, in their investment banking department. I was the assistant to one of the bankers, the regular assistant was out on maternity leave for the summer, so it worked out well for me.

The guy I was working for, Travis, was about 30 and very good looking. He was also trying to get into my pants from day 1. I wasn't necessarily against that, just hadn't decided yet. He would say stuff like: "hey, there's a promotion in my pants, want to try to find it?"

I didn't take any shit from him, or anybody really, and as likely as not would respond with something like: "well, it's probably too small a promotion to interest me."

So, he had just closed a pretty big deal, financing several large resort properties in the Hawaiian islands. Made himself a very nice commission and a ton of money for the bank. He was planning on celebrating by taking a trip to Vegas, along with his best buddy, one of the other bankers. There was a banker's convention going on in Vegas and he was planning to charge the whole thing to the bank. As usual, I was making his travel arrangements, flight reservations, hotel booking and so on. He asked me to book a luxury suite at the Bellagio. Also, did I want to come along with them, they could also write that off to the bank since I would ostensibly be working as his assistant during the convention.

I may be blonde, but I'm not dumb. I knew I would be expected to pay for this trip with pussy, probably giving it up to both of them. Still, that wasn't a deal breaker for me, and I had never been to Vegas, so I said, "sure, I'll go."

We arrived in the early afternoon and made our way to the Bellagio which, if you haven't seen it, is pretty impressive. They have these fountains in the front of the place that look like something from a king's palace. The suite had two bedrooms and a large common area between the two. Travis indicated that I should unpack my bag in the bedroom he was going to occupy and that Jack, his buddy, would take the other one. About what I expected.

We went out to do a little gambling, had dinner and took in a show. Arrived back at the rooms around 11:00. It wasn't long afterwards that Travis had his tongue down my throat and one tit in his hand. He said to me, loud enough for Jack to hear, "hey you have two of these, do you mind sharing?" Also, about what I expected and I was about to say ok when Jack broke into the conversation; "that's a very tempting offer, but I have made other arrangements for myself. There is a porn star that I have always had the hots for who has a sideline working as an escort here in Vegas; I called her earlier and made arrangements for her to be here in about an hour. So, if you two can stop acting like horny teenagers for just a bit, we can all play together when she arrives."

I was intrigued and I could see that Travis was as well. This would be my first experience with a "professional" and I decided to look at it as a learning opportunity. Also, an opportunity for an orgasm or two.

It turned out that the hotel had an adult movie channel, and we were able to get a Veronica Luv video up. Veronica was the pornstar Jack had hired. She was gorgeous, short red hair and a terrific figure, tits almost as big as mine and a great ass. In the scene we watched, she was eating another woman's pussy while some porn stud was fucking her in the ass. The crotch of my panties was wet by the time that scene ended. At about that time there came a knock at the door. It was Veronica of course, but she wasn't looking quite as good as she had in the video we had just watched.

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