A Winner's Circle

Story Info
Weekend in Vegas falling in love with a millionaire.
6k words
4.48
20.2k
3
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was Friday evening and our trip to Las Vegas from southern California would be about a 5 hour drive. Getting through Los Angeles can be a nightmare on the freeway. My girlfriend Linda and I decided to take the weekend off and just go! We had been planning to do something fun for ourselves and what would be more fun than 2 women in Las Vegas for a weekend? Once past L.A. it was clear sailing on I-15 north.

We decided to stop off in Barstow for a bite to eat. Barstow was at one time a smaller town in the Mojave Desert but had grown quite a bit and is considered a "pit stop" and about half way through our trip and for travelers on their way to Vegas from southern California. We had never been there but wanted to see it just to say we "were in Barstow!" We stopped at the Mac Donald's at "Barstow Station" that was built entirely from passenger train cars. We had our burgers and then continued on our way to Vegas.

We were tired when we arrived and checked into the Sahara Hotel. This is a landmark hotel that holds many stories and memories from the past with various Hollywood entertainers and one of very few hot spot hotels that survived the many changes in Vegas over the years.

We got to our room and freshened up. We decided to go down to the casino to see what was happening and perhaps hit a million on the 25 cent slots. We passed by one of the roulette wheels where it seemed someone was having some luck. We tried our luck with a few slots, but was only able to break even from the few dollars that we put into them.

I am a people watcher and love to "size them up" and try to figure out what they did for a living and peg them with a certain type of personality that suits their faces. Linda and I decided to have a few drinks at the bar. After a while, and still playing our "people game", we decided to guess which men were wearing "boxers" or "briefs". We would look at a man's butt going by then decide what he was wearing for undies and chuckle about it. One man walked past and we decided that yes he was indeed wearing "boxers". I guess he overheard us and stopped in his tracks. Linda spotted him walking back towards us and said "Oh my God Barbara! He's coming back!" We both gulped thinking this is so embarrassing, and what will he say when he gets to us? Better yet, what are we going to say to him?

This man came up to us and introduced himself as "Rich". I smiled as did Linda. Then he said "if you would really like to know, I'm wearing boxers." Linda and I both turned red. He chuckled and said "I would like to buy you ladies a drink." It had to be obvious that I was still blushing over the "boxers" remark, but I responded by saying, "my name is Barbara and perhaps maybe we should buy YOU a drink. This is my friend Linda. I'm sorry if we embarrassed you." He laughed and said that he was "flattered that 2 lovely ladies noticed his butt." We all laughed and it seemed like the ice had been broken.

We sat with Rich for quite a while. He was fascinating to speak with. All he would tell us was that he was in business for himself and he comes to Vegas frequently to "get away from business and just relax." He told us that his business was based in N.Y. He told us that he traveled a lot with his job. What we did not know was that he was a self made millionaire.

He told us only a few tidbits about his personal life. He was divorced, had grown children that were both married, and traveled a lot on business trips to various parts of the country and world. His personality was absolute dynamite. He certainly knew how to treat a lady and he was a perfect gentleman.

After a few drinks, Linda excused herself and told us she was going to the room to sleep. Rich smiled at me and asked if "I would stay for a bit and talk more with him." He seemed sincere and to me he was fascinating, so I told him I would stay a while longer. Linda left and Rich and I decided to sit at a table where we could talk and get to "know one another." He asked me about myself and what "did I do for a living?" I told him that I was a flight attendant and had been for 7 years with "Conus Airlines." He raised his eyebrows and said "Really? I like flight attendants and I have flown Conus." I thought after that remark that he probably had a some notches in his belt with a few stews.

He asked me questions about my personal life and wanted to know if I was "married, divorced or attached?" I told him that I had been divorced for 2 years with no children and that I was "not planning to remarry ever again!" He chuckled and told me that "someday I would meet someone and fall in love again" because he thought I was "very pretty with a great personality." Funny thing, because I thought the same of him, meaning a great personality and quite handsome.

We sat and talked until nearly dawn. I did not want to retire from the conversation or this man but I could not keep my eyes opened. I told him that I was very tired and thanked him for the wonderful conversation and company. He asked me how long I would be in Vegas and I told him for 2 more nights. He told me that he liked me very much and would I consider "having dinner with him the following night?" I smiled and said "yes I would like that very much." He also invited Linda but she and I had an agreement. If we happen to meet someone that we seemed to like, that we should not feel obligated to spend time with the other if one of us could have fun on a date. I told Rich that "I was certain that Linda had plans" but that I would "love to have dinner with him the following night." He told me that he was staying at Caesar's Palace but would "pick me up at 7 tomorrow night." He asked me for my room number so he could call me when he arrived so I would "not have to stand in the lobby waiting for him." At first I was a bit reluctant but he seemed so sincere, so I just told him the room number. He told me to "dress to the hilt because we were going out on the town." I smiled and said, "I will see you tomorrow night." He smiled back and I left to go to my room.

Later in the morning, Linda ordered breakfast to be delivered to our room. She woke me when the cart came and we sat to eat. She asked me all about Rich. I told her what I had learned about him and that I had a date with him that night. She was pleased that I seemed interested in Rich. I told her I had to buy something to wear for the occasion and right after we ate, we dressed and went looking for the perfect outfit.

I found a dress in a shop along the strip. It was a black dress, not too dressy but would be appropriate for any dinner date that was labeled as "out on the town.". The dress was ankle length and slim fitting with one strap across the left shoulder that was a glittery silver. It had a front slit to above the knee and yes I looked great wearing it! I bought black high heeled shoes with a small rhinestone clip on each shoe and matching purse. The dress was made to be worn braless. I was ready for my date.

It was mid afternoon when we got back from shopping and I was becoming more and more excited about seeing Rich again. He was a gentleman, and very good looking. He always smiled and seem to have genuine interest in anything I had to say. He was polite to everyone around him and a very good listener. He had blue eyes and blonde hair, and when he spoke, I hung on to every word he had to say. He told me about himself but it seemed there was much more to him than just chit chat and conversation, and I wanted to find out who "Rich" really was inside.

I was ready early, in anticipation of my date. At 7 on the button the phone rang. It was Rich. He asked if he could come up to the room to escort me downstairs. I said "yes that would be fine." Linda gave me a last minute thumbs up as she checked to make sure every hair of mine was in place and everything I was wearing looked alright. There was a knock on the door and Linda answered it. When she opened it, there was Rich in a tux. He looked so handsome I wanted to kiss him right then and there. He took my hand and leaned over to kiss me on the cheek. As he did so he told me that I looked "fantastic". I thanked him and we left to go downstairs. During the ride down in the elevator, he kept staring at me and smiling. I asked him if there was "something wrong?" He said, "no not at all, I just like looking at you." I smiled again, said "thank you" and blushed.

We exited the elevator and stepped into the lobby of the Sahara. He gently took my arm and tucked it in his to escort me to the car. As we stepped out of the hotel lobby, I saw a white stretch limo parked directly in front. We were headed that way. The driver got out and opened the door for us and we got in. I turned to Rich and said, "I never expected anything like this." He smiled and said, "I want this to be an evening that you will not forget." I already knew that for some reason I definitely would not forget this night. I smiled.

In the car he told me that he enjoyed coming to Vegas and felt it was his lucky night to have met me at the Sahara. He liked to make the rounds to various casinos when visiting there.

Rich asked me if I liked Italian food because it was his favorite. I said "actually yes. It's mine as well". He said "good, then Italian it shall be." He instructed the driver to take us to "Piero's" a 5 star Italian Restaurant. We arrived within a few minutes. As we entered Piero's, we were greeted by the maitre d' . He escorted us to a very private area in the restaurant where there was a table for 2 waiting for us complete with candle light. Very romantic. On this table lay a fresh red rose in a tiny glass tube filled with water that was gently placed onto a plate, and a chilled bottle of Dom Perignon champagne. This was very romantic of Rich to do this and I told him so. Immediately after being seated, the maitre d' popped the champagne cork and poured, then he left the table.

Not long after we began sipping our champagne, a gentleman approached the table to say hello to Rich. He was introduced to me as Rich's friend "Fred" and the man gently kissed my hand and said "it is very nice to meet you Barbara." I said "thank you. It's nice meeting you too." He told Rich it was "nice seeing him again." Rich told him that "whenever he is in town he always likes to stop at Piero's and eat." He continued by saying, "this was our first date" and he "wanted it to be special so we came here to eat. Hopefully we will have many more dates." Rich thanked him for stopping to say hello and Fred told us to "enjoy our meal" then left.

Fred was actually the owner of Piero's and knew many famous people that came to his fine restaurant. He catered to them and they liked that. The restaurant is somewhat removed from the main stream Vegas glitz, and celebrities are able to find some privacy and relaxation at this multi award winning 5 star restaurant.

We ordered our meals. Rich made sure my glass was filled with Dom Perignon. When he spoke to me, he would reach across the table and gently take my hand in his, especially if he had something kind and caring to say to me. To me it seemed that he held my hand all night because he always found something to compliment me about. My head was full of wonderful thoughts about Rich. This kind gentleman that revealed parts of his inner self, made me want to know as much as I could about him. I had known him for only 24 hours but I knew that I could get very accustomed to being treated so lovingly and respectfully by him, and also knew that I could quickly fall deeply in love with him.

We left Piero's and stepped back into the limousine. Ray the drive asked "Mr. Wilson" (Rich) where he would "like to go now?" Rich told him to drive to Hoover Dam for a "spectacular view" seen only at night when well lit. It took us almost an hour to get there but we enjoyed the ride.

We pulled into a tourist's parking area and stepped out. Yes the view overlooking the dam was indeed spectacular. Rich turned to me and said "I want to kiss you." I did not resist. He slowly stepped to me, placed his index finger under my chin and lifted until my eyes met his. He leaned forward and kissed me lightly on the lips. He looked at me and told me that he was "very attracted to me" and kissed me again. This time longer and more passionately. I melted in his arms. I have never been kissed like that before in my life, and if I had my way, I would never let him stop.

Rich was very well versed in the world of travel and etiquette and knew how to win a woman's heart. Problem was how many women were on his list, if indeed he had a list. I was afraid that if I did fall in love with him that he may not feel the same about me and I would be heartbroken. I needed to be careful.

We returned to the limo, and Ray opened the door for us. I stepped in and then Rich. He closed the window that separated the back of the limo from the chauffer that was driving. He looked at me again and kissed me. His right hand slid softly to my should and the one strap on my dress holding it up. I was braless and he soon found that out by sliding the strap off my shoulder and down. He whispered in my ear that he "could not keep his eyes off me and wanted to make love to me." I could not resist. His lips followed his hand that gently caressed my breasts. His tongue encircled my nipples as his hand moved down to the slit in my dress. He touched my knee and slowly moved his hand to my thigh and began to massage the top of my nylon and to where it attached to the garter, and then to where the stocking met my skin. His hand moved to my panties and to the silk and lace that housed "her". I was indeed wet and we both knew that if he continued, for only a few more moments, that I would have an orgasm, but he stopped. He picked up the intercom phone and told Ray to "bring us back to Caesar's Palace." My heart was racing and I did not know if I should tell him to take me back to the Sahara or allow this wonderful evening to continue on to passionate love making. He kissed me again but said nothing. He gave me a look and raised one eyebrow as if to say "if you do not want to go back to my room, tell me now." I said nothing. He gently repositioned the strap of my dress back onto my shoulder as we drove to the front entrance to Caesar's.

We rode the elevator to Rich's suite on the top floor. It was a beautiful room overlooking Vegas. The lights were mesmerizing and quite romantic. This suite included a living room, kitchenette, wet bar and bedroom. From the bedroom one can walk out onto a balcony. Rich took off his jacket and tie and tossed them onto a chair, then took my hand and we went out to look at the lights. A slight breeze cooled us from the normal dry Vegas heat and air. He turned to me and kissed me again. He took my hands and threaded his fingers through mine and raised my hands above my head as he pressed me against the outside wall. The stars above were like diamonds, and there for anyone who could reach them. Once again he slid the strap to my dress off my shoulder and let my dress drop to the floor of the balcony. The soft breezes that kissed my breasts made me feel very sexy and sensual, along with the idea of being so vulnerable perhaps to the eyes of others peering up at us. But I did not care.

With one hand he continued to hold my hands above me, while the other explored my scantily clad body. He gently kissed me from my lips to my breasts and sucked my nipples until they became erect. Slowly he released my hands, as his moved down my body to the tops of my nylons. He knelt down and began to unhook one front garter as he kissed my thigh, then the other garter, slid my shoe off as he moved the stocking down to my ankle and foot then off me. He did the same to the other leg. He stood up in front of me and reached back to unhook my garter belt and it too dropped to the floor. He kissed me again then took me by the hand into the bedroom.

He bent me backwards onto the bed and laid on top of me, kissing and touching me. Slowly his lips moved from mine to re explore my body. My head was spinning and my heart was racing with every touch and kiss that he gave me. I could feel myself giving in to this wonderful man as I allowed this exploration to continue. I could feel his hot breath on the only piece of clothing left on my body, my black silk and lace bikini panties. He stood up to remove his shirt,slacks and boxers. As he turned to do that, I stood as well. Without a word spoken, I kissed him and backed him onto the bed. With my fingers at each hip I slowly slid my panties off and crawled on top of him. My intent was to drive him wild with passion. I kissed him once and moved "her" down to his cock. As "she" ground into him, I took his hands in mine and placed them onto my breasts for him to play. I could feel him getting harder and harder for me. I moved carefully backwards and down on him. He looked at me then closed his eyes and let out a satisfactory moan. I took his hard cock into my mouth. My tongue circled the tip of his penis, and each time one circle was completed, I gently sucked him into my mouth. Each time I sucked, I brought him further into my mouth and closer to orgasm. When I tasted drops of pre cum I stopped, and moved back up towards his lips. By the look on his face he very much wanted to accept "her" in that manner. I moved "her" to his mouth and ground into him. His tongue played with my clitoris making it hard and making it throb. He repositioned himself and told me he wanted to fuck me with his "tongue" and he did. I did not want to cum this way but it happened, and he loved it. I wanted to cum while he was fucking me and on top of me. But I would soon find that there was much more to his love making.

He rolled me onto the bed and went down on me, licking, kissing and sucking and yes, brought me once again to completion. He slid me to the end of the bed and slowly entered me. I wanted more but he said "no" with a smile, then pulled out. He entered again, and one more time pulled out. I begged him to "fuck me" and this is what he wanted to hear from me. He told me "tell me again!" I begged him, "Rich please, please fuck me, take me hard." He crawled back onto me and pushed into me. Sweat was running off both of us as we continued this pornographic scene. He took both my hands and held them above me and pumped into me faster and faster. As he thrust into me, I could feel the muscles inside of "her" readily responding to all he had to give me. He pounded me hard and fast but continued to restrain my wrists with his hands. This restraint and sexual excitement brought me to a height I have never felt with any other man. I wanted everything he had within him to give to me, and yet the idea of him having total control over me at this point, added a bit fright to this frenzy. But this "soft rape" was such a turn on for me, something that I had never experienced. It seemed as though he too enjoyed this "role playing". I struggled a bit with my hands but he just held me down harder. The more I struggled the more excited he became and fucked me faster and harder. He asked me what I "wanted!!?" I told him "I want you to fuck me." "Say it again to me!" "I want you to fuck me" I responded. He thrust into me one more time as hard as he could and he came with a moan so loud, there was no mistaking the satisfaction he felt. At the same time my entire body quivered and responded to clitoral and vaginal orgasms resulting from intense sexual play and love making with this man. The likes of which I have never ever experienced.

We laid together in bed just gazing into one another's eyes. He put his arms around me and held me closely to him. He told me he had never made love like that before with such sexual intensity. I responded by saying, "neither have I." I realized that making love and having sex like we did, was alright if it involved 2 consenting adults. Having gone through this sexual experience with him, I could not help but have trust in this man. Somehow I felt as if I had known Rich all my life. I guess you might say we "clicked".

12