Truth or Dare

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Aman is married to a sexy woman he can not trust.
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Gumbo25
Gumbo25
1,188 Followers

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.

———————————

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.

————————————

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.

———————————

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.

——————————

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 risqué. 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.

"Don't you dare" Jackie replied.

With that Trent stands up unbuttons and unzips and drops his shorts and his boxers. He was impressive 6 inches flaccid and not thin. Both Anna and Sally were staring, I was shocked and Karl was laughing.

He kind of gyrated a bit like a male stripper. As I looked at Anna she was just staring at his big dick.

At this point Jackie said, "I'm leaving."

She looked a little pissed. She also told Trent he can get in the car with his clothes on or he could walk home. Everyone left shortly and the party became officially over.

As we were straightening up Anna was uncharacteristically quiet. We were finishing up and I said,

"that went a little too far, don't you think?"

"Oh, it was just for fun" "don't be such a stick in the mud." She replied jokingly.

"Anna, people were nude and nearly nude here, and you were one of them." I retorted.

"Nude" she said, "I will show you nude!" And she proceeded to strip.

I was quickly and thoroughly distracted. It did still bother me, the way the party evolved and I was determined to have a serious discussion about the events tomorrow. I also have to say I am not one of those guys that gets a thrill out of their wife exposing herself or more around other men.

I fell asleep sexually fulfilled, but a bit troubled.

Sunday morning I was up first and went for my run. During the solitude of my exercise I planned out the discussion I was planning on having with Anna. I was going to make the point that I enjoy fun and a good party as much as anyone else, but my wife and our bodies were only for us. We made that oath on the day we married. I was not going to compromise one bit on that.

When I got home I could here Anna on the phone. She must have heard me because the laughing stopped and the volume went way down. I did think I heard the distinct word "package" before she heard me.

"Who was that?" I asked,

"Oh just Sally," she giggled. "She and Karl had a great time and rated our party as the best yet,"

"About that, I think we should talk about some of the actions last night and specifically some of your behavior."

For the most part Anna was good natured and it took some to get her mad. I succeeded in reaching that point with my comment about her behavior.

She lit into me about it being innocent, it was just fun, no one else is upset and nothing happened. I tried to be calm and reason with her and explain my feelings, she was not interested.

After she unloaded on me I got the silent treatment.

While I started my yard work I tried to analyze my feelings. I really didn't think I was being unreasonable. I wanted to give her a little leeway in being who she was - that was who I married. I enjoyed her free spiritedness, but anything intimate should only be mine. Including who sees her body.

I have to admit I was a little insecure. Anna is a beautiful, sexy woman and I am a fairly plain Financial Planner. I know I'm not bad looking and I stay in good shape. But I also know she gets hit on constantly by all types of guys.

I have no real reason to doubt her fidelity but there were a couple instances before we were married that activated my radar . . . .

——————————

We had been dating almost 3 months at this point and been having sex for nearly the entire time. I felt close to Anna and we had some good conversations and I learned about her life.

Her father left the home leaving her mother and an older sister. Anna craved male attention and once her body started developing, she got it. I didn't want to dig deep into her sexual history but I got the idea that her virginity was long gone by age 16.

It sounded like there were boyfriends and casual friends that she "played around with", that was her phrase. Unsurprisingly she never had to look too hard to find the next one. She loved attention and she knew her looks could get that for her.

We were invited to a party of a casual acquaintance this coming Saturday night. At this point we had not formalized our exclusivity but in my mind we were exclusive. She said she loved me and to me love and exclusivity went together.

It was December and the party was a little dressier than normal. When I saw what Anna was wearing my eyes almost popped out of my head. It was a red dress that barely covered her boobs.

"You like my dress," she teased.

"Anna, you look great, but, wow, it's pretty skimpy," I replied. "you know I will likely have some clients there and, well, um it's a little too much,"

Now Anna doesn't often get mad, but when she does it's almost always about how she looks.

She got mad. She said I thought she was trashy. She said I thought she was going to embarrass me, and on and on.

It took some time. I apologized and though things were a little frosty, we went to the party and she wore the dress.

The house was a large one in the hills. Beautiful decorations, lot's to eat and drink. Some of my work colleagues were there, people I knew from college and others I knew from the athletic club I belonged to.

There was one guy at the party I remember from college, something McCallister. One of these arrogant, good looking pricks. Confident, a smarmy smile pasted on his face and slick back black hair. He was cruising around with that cocky smile and a glass of champagne. Then he saw Anna.

Anna was getting a lot of attention, mostly male attention and much of the attention was focused on her cleavage. She was by my side and suddenly I had become popular with colleagues and casual acquaintances.

At one point I went to get us a drink and when I returned McCallister was chatting up Anna. He acted like I was a long lost friend. She was loving it, all this attention and now this good looking guy was behaving as if everything she said was the most interesting thing he had ever heard.

I managed to steer her away from him, but as parties go, you end up drifting this way and that and Anna and I became separated. I was talking to some work colleagues and they were sharing some business ideas that were quite helpful. I realized it had been over an hour since I had seen Anna.

I took a quick glance in the living room the kitchen and the family room off the kitchen. Nothing. I didn't want to seem agitated, but I was on a mission to find her. I did not see McCallister either.

There was a group outside smoking and I walked out in to the winter air. No Anna. I was on my way back in when I heard her. Her laugh, from down the street. I walked down the sidewalk and there she and McCallister were walking up the street.

It took her a minute to see me and as I watched her and McCallister they seemed to be enjoying one another's company.

"Oh hi honey," "Jim was just showing me his new BMW," she said.

"She's a handful,". McCallister said, "I mean the car," he laughed.

I looked at Anna, I didn't see anything specifically amiss, she just seemed a little, rumpled.

I had a fake smile on my face. Inside I was seething. Anna came up and put her arm around me as they walked up.

"I'm leaving now, " I said "just making sure you wanted a ride home,"

"Of course I want a ride home," she said, "why wouldn't I" She asked me questioningly.

At that point McCallister slapped me on the back,

"Nice to see you again," and he offered his hand.

Now I'm no body builder but I do work out and I have always had a strong grip. That, and the combination of my anger at Anna and this asshole's insolence, I gripped his hand.

He didn't have a chance and by the time he realized what was happening I was crushing his hand. His knees buckled and his mouth was open in a silent cry.

"Honey, your hurting Jim" Anna cried.

"Oh sorry, my bad" I said, and started walking to the car without looking to see if Anna was following me.

By the time I got to my car and buckled up, she had caught up with me.

This was our first big fight. I really liked her normally. She was great looking and the sex was off the charts, or at least off any chart I had ever heard of. I knew she sought attention and gauged her value in the attention she got from men.

We had not formalized anything at this point. For me though, a steady sexual relationship in which we saw one another more than a few times a week and talk of love is the adult version of going steady, but we had never had that particular discussion.

I dropped her off and she gave me a questioning look when I told her I was staying at my house tonight.

"Oh honey, come on up." "Nothing happened with Jim, we were just having fun." She said.

"Well I guess for me, that's just about enough FUN for one night, see you later," and I took off.

She called and texted and I ignored her. Life went on for me and I spent the week focused on my work. My week on the coast was next week and I decided to leave Saturday morning in stead of my normal Sunday night. I called my Mom and she was thrilled to have me over the weekend.

I had a good week in my home town. I had some good client meetings. Professionally my steady business on the coast and my growing business in the city was making me successful. I was achieving my financial goals and was being noticed within my organization.

A week ago I would have to say that my personal life was going in the right direction also. I couldn't really say that now. She kept texting and calling and my responses were minimal. She asked when I was getting back and I told her Friday night.

Gumbo25
Gumbo25
1,188 Followers