It was our turn to host the party this weekend.
About once every month to six weeks six of us, three couples, would get together usually at one of our homes. It was Anna's friend Sally and her husband Karl, our neighbor Jackie and her current husband Trent. Sometimes there were others but this was the core group.
We were all in our late 20's or so and none of us had children. We couldn't. Sally and Karl didn't want any, and actually Trent had 2 children from his first marriage but they lived with his ex. He desperately wanted custody of them.
There was food, drinks and we normally had some sort of theme. Sometimes it was trivial pursuit, cards, a sporting event on TV and when we met at Trent's house there was swimming in his pool, weather permitting.
The girls, particularly Sally and my Anna would organize these parties with a bit of phoning around to make sure that we could get critical mass together on a particular date.
Anna loved chatting and gossiping on the phone and enjoyed the organization. She is a busty, curvy woman with wavy light brown hair. She is a bit of a flirt, and at times it pisses me off. She loves the attention but to my knowledge has never crossed any lines while we have been together.
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I grew up and my family still lives in a coastal town in Oregon. I graduated from the state university in finance and took tests to be a Certified Financial Planner. I was a bit introverted but I loved studying money, the markets, statistics and the history of our economical system.
My Dad sold insurance in our town and his honest and solid reputation gave me credibility in the financial world of our town. In fact I was named after my father, he was Joseph Washburn and I was called JT.
I started renting an office in his building. I worked hard setting up meetings with folks and explained my strategy for their money. I told them that overall I wanted their money to grow steadily but conservatively.
I was affiliated with one of the national companies and got a lot of financial data from them. I also spent hours doing my own research. This was what I really enjoyed.
I was successful that first year to a point. My clients got good solid returns and their portfolios outpaced the market. I enjoyed sharing office space with my Dad and many of his long term clients became my clients. I tried to meet with my clients regularly, get to know them better and just add that personal customer service. They enjoyed and appreciated the contact.
As I started year 2 one thing became clear, there was not enough business in our town to make a good living. I had my own financial goals and I, as a student of economics, realized that I could not support myself with just the business in this town.
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The weather was nice for our party and we decided to eat outside. We had a large deck with a barbecue and an outdoor kitchen area. I asked Anna what she wanted the theme to be tonight.
"Let's play a game", she said. "We will play a fun and funny game that everyone will love, doesn't that sound good JT," she gushed.
There was a little competition to see who could have the "funnest" party. I just enjoyed the company, for the most part and the food and the drinks. I admit I do like my wine, and there have been a few times that I drank a glass or two too many.
"What game?" I asked.
"Don't worry JT, I'll figure it out, you just get the barbecue ready."
That was fine with me. I let my mind wander a little as I was getting things set up and I started thinking about the group that was going to be over tonight.
First there Sally and Karl. Sally and Anna have been friends since high school. Sally is a little overweight but shaped proportionately. Sally has big boobs, I'm estimating 38's. She likes to show them off with low cut tops. Anna does too and there are times I have to overrule her wardrobe selections.
Karl is a diesel mechanic and works at a big shop in our city. He's easygoing. He doesn't seem to mind when Sally flirts and shows off. He's a big guy probably 6'3, 220 or so. I like him OK, but would probably never choose him as a friend without the connection between Anna and Sally.
Jackie and Trent were neighbors and I really can't recall how we became so close to them. Jackie is plain faced but has an outstanding body. Not the curvy softness of Anna more of a taught leanness. She is smart and I find of the whole group she is who I have the most in common with.
Trent is a golfer. He's lean and about 5'9". There is some arrogance with Trent. It put me off at first but I have learned to like the guy. Not sure I trust him, but he is smart and funny and fun at these parties.
Just then I heard the doorbell ring, the guests were arriving.
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I decided to move my financial planning practice to the city. I joined a firm in the city but maintained my practice in our coastal town. It was only a 2 1/2 hour drive between the two. My plan was to be there a week a month. I stayed with my folks, met with clients and prospective clients on that week. So far it was working out well.
I roomed with a guy I had gone to college with, Julian Lee. Julian was an IT guy and worked at one of the big banks. Julian was very creative and I was surprised that he chose this particular career path. We had a two bedroom apartment in the trendy Maples district near downtown. I could walk to my office and there were lot's of restaurants, bars and boutiques within walking distance. It definitely was the young, hip and trendy area.
One of these bars was where I met Anna. Anna worked at Luca's a hip restaurant and bar about 2 blocks from our apartment. I think it was the third time Julian and I were there that I got to talking to Anna.
To me she looked like a Playboy bunny. Voluptuous and pretty. She always wore something to accent her boobs and cleavage. Anna was tending bar and we got to talking and she asked me all kinds of questions about my life, my career, my goals etc.
To be honest I was somewhat surprised that she was paying so much attention to me. She was gorgeous and here I am this plain looking financial planner.
In high school I had a steady girlfriend, Gail Benson. Gail was attractive, smart and fun to be with. We tried to make it work through college, but it was too hard to do. I dated some through college, but never had a long term girlfriend during those 4 years.
That night we left and I almost asked Anna out, I even got the impression she wanted me to. I was just a little worried she would say no and then we'd have to find another bar to go to.
"Man she's hot," said Julian, "she is in to you". "You need to ask her out!".
"You think so?" I replied.
"and you better do it quick, someone is going to beat you to it if you don't."
The next night I went to Luca's on my own and had a date with Anna for Sunday night.
And so we dated. I was a little intimidated, I had never been with a girl this good looking, but she gave me all the right signs that she was in to me. It was not long before she gave me what I considered the ultimate sign, herself sexually.
Sex was Anna was like nothing I had experienced in my life so far. I have had a handful of different sexual partners including my high school girlfriend Gail. I had done my share of sexual exploration in my limited experience, but I was an undergraduate. Anna had a PHD.
We did everything, she was totally uninhibited. She taught me things, she did things to me, and we did things together. She has beautiful breasts a beautiful ass and her shaved pubic region was wonderful. She is not overweight but not a hard body. Soft and curvy and completely feminine.
Every so often I would wonder how she learned all these things. How experienced was she? I mean I knew the answer, VERY EXPERIENCED. But I avoided the sexual history discussion, I was afraid it would be too painful. Any consternation I felt on this subject was more than offset by my sexual satisfaction.
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Everyone was sitting on our back deck. We had finished dinner and we were all about 2 drinks in to the evening. I think I was on my third glass of red wine.
I had a long discussion with Karl on how he was hoping to be named manager of the diesel shop where he worked. He told me that the owner was strictly religious and he asked me if I thought it would be a good strategy to attend his church, to get in good with him.
I said that unless he was sincere about the religion it may come off as disingenuous. He said that he would have to think about it.
As we sat idly talking Sally said, "so Anna what is the plan for tonight?"
"OK everyone," Anna started, "have an open mind, and it's just for fun, we are going to play Truth or Dare!"
I thought oh no! But Karl, Sally and Trent clapped and cheered showing their approval. I looked at Anna and she smiled then quickly looked at Sally. Karl and Trent were grinning. Jackie had a half smile and was the only one beside me who wasn't specifically enthusiastic.
It started out pretty mild mannered with a hint of sexual innuendo, nothing too risquΓ©. Who is your movie star crush, how old were you when you lost your virginity etc.
And then it was Trent's turn to ask, he chose Anna and she chose dare.
"Sally, I dare you to take off either your shorts or your top,"
"Wait a minute," I said.
"It's OK I have underwear on, it's like a swimsuit,". Anna said.
Anna loves attention and there have been times that her behavior came close to crossing the line. While I loved the confident sexuality she shared with me. I certainly didn't want others experiencing any bit of that intimacy with Anna.
She quickly whipped off her top and there she stood in her lacy white bra. Her nipples were prominent through the gauzy fabric of her bra. The tops of her breasts quivered. She stood proudly and Trent and Karl whistled.
Sally giggled "you go girl!"
Anna was loving the attention. I was a little pissed, but I kept my thoughts to myself. It went back and forth with nothing too bad until Sally was dared to show her unobstructed naked breasts. Unlike me, her husband Karl was urging her on.
She flashed them and they were definitely big, not my taste, but big. Everybody was laughing except Jackie and I.
I said, "one more round, and then that's the end of this game,"
A few laughs and protests, but I was concerned that we may cross a line.
It was Anna's turn and she asked Trent.
"OK, dare" Trent challenged.
"Flash your dick for 10 seconds," Anna challenged.