Weekend Getaway

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Losing a bet produces seductive results.
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I am not a cliché aficionado but one stands out in my mind, "do not wish for something unless you are prepared for it to come true." Before talking about why this cliché stands out, I will introduce myself and provide some background. Jennifer is my full name but many people call me Jenny. Currently, I am 40 years old, l I do free lance advertising and living in a small town of Poldick, South Dakota. The surrounding area has more farm animals then people and still has buildings built by pioneers, who settled this town. My feeling the town's link to pioneers gives a general impression people from this area are conservative, religious, and innovative. In some ways, if feel that impression describes me.

In retrospect, a lot of my life, including my decisions, is somehow associated with growing up in a rural town not too far Poldick. It is fair to say my parents were conservative in every aspect. Growing-up watching television was limited, due to my parents believing television programs having too sex or promoting a progressive liberal agenda. If I was not doing homework or outside with my friends then I was at church doing something in order to keep my parents happy. This led me to develop a rich fantasy life due to the isolation living in a rural area but at the same time being afraid to experience something new. The fear of adventure and always wanting to do the right thing led me to live a very insulated life.

During my teen-age years, growing up in a religiously conservative home meant I did not date until I was a senior in high school and it was not until prom that I had my first kiss. It was not until I moved out of my parent's home studying art at university that my life began to change. During my junior year at university, I met my husband Dan whom was in the same Introduction to Sociology class with me. His intellect, English accent, and having experiences different from mine initially attracted me to him. Unlike me, Dan was not a virgin when we met. This does not mean I was frigid. My sexual interests were quite alive, I willing to explore but I kept having sex as a fantasy. One example where I can give of my sexual interest being alive, while at university if I had a few moments alone I would take my pants and panties off to play with myself while fantasising about being the object of desire. Another example my roommate Penny and I would go out partying together then come back to our dorm room exploring each other's body. Nothing materialized between Penny and me. Then there was Robert whom I dated for about six months before meeting my husband Dan. Robert was a lot like me in many ways idealistic and had his views shaped by living in a religiously conservative home. Such backgrounds made our relationship difficult because we had limited experiences and the experience we had made our conservative background limited our physical involvement with each other. This meant my experience with him was limited to petting, nothing more. It would be fair to say that prior to meeting Dan I led a cloistered life with many of my ideas about sex based on fantasy or religiously conservative ideas.

As I started knowing Dan, I learned about his sexual experiences including a threesome with two women and a drunken bj with his roommate, though he did not go into much detail about it. His experience, I feel, made him more willing to take a risk in our relationship. At first, this lead to some conflict due to our differing viewpoints but as we learned more about each other, we learned out to work through it. After graduation, we were married starting to live the American dream, a house, careers, and children. If you looked at us after nearly 20 years of marriage, we would appear as any other married couple. However, if I just lived the American Dream, there would not be much of a story to tell and the story would end here.

After getting married, our lives were nothing spectacular. In the beginning of our marriage, sex was predictable and I was reluctant to try anything new. Dan is always the one suggesting new things and pushing new things to try. Most of the time I will reject his ideas but as time passed, I tried some of his suggestions, such as sharing a fantasy during fore play. A common fantasy was having sex with another man with Dan participating or arranging something then telling Dan about the details. This fantasy came from occasionally watching threesome porn together and our discussions about trying it. There is a few times when we started to look for a third person to join us but I would say 'no' due to my fear about the risk. Another common activity for Dan and I, tying Dan down with some of his older ties and then doing what I wanted with him. Tying Dan down gave me a sense of power, a sense of control, and allowed me to break out of the shell that defines much of my life before Dan. Dan's patience with me along my willingness to explore, in some ways allowed me to be more sexually competent. Nonetheless, in my private moments, I still like to play with myself fantasizing being the object of desire for another man while Robert watched.

With that said, if you were to ask me before 4 May 2011 if I had any regrets, I would confidentially say there was one, not going all of the way with Robert. However, that was going to change. The week begins like any week for us, since were on vacation and staying home. Since we were staying home we kept our morning routine of discussing world events. Then on May 4th,, the day before an election in the UK, Dan and I decided to bet on the outcome of the outcome of the Alternative Vote (AV) referendum in the UK, Since Dan is originally from the UK and politics is something he enjoys. He felt that the UK would not approve AV but I felt the idea was a good idea because it provides a fairer voting system. This lead to a lively debate at the breakfast table and we decided to solve our difference with a wager on the outcome.

Unlike previous wagers, this one was different and I am not sure why we moved our wagers from non-sexual to sexual. It could be as a couple we were heading in this direction or it was due to both of us being on vacation. My wager was an unassuming one, being able to tie Dan down using restraints and dominate him. Dan knew about my relationship with Robert, the attraction I had for him, but never said anything about it until now. His bet was unexpected if he won I would find Robert, sleep with him, and I would arrange it. Since our bets are more innocent than this, I told Dan, "I need time to think about it."

"Okay, I will give until this evening but unless you tell me otherwise, I am going to assume my wager is acceptable."

I felt he was joking about his wager because as a couple we knew where the implied limits existed and I know he would not expect to do something that I was not comfortable doing. Nonetheless, it did get me thinking and wondering what it would be like to be with Robert and the thought started to get me aroused. A few explicit images, of Robert fucking me, ran through my head before Dan said, "I am off to do the weekly shop." That gave me at least 30 – 45 minutes where I could go upstairs and play with myself thinking about how much I might enjoy it. Once I got out my dildo, it made me think more about fucking Robert. The thought of him fucking me now made me quite wet and I could feel my pussy yearning for Robert's rock hard shaft inside of me. A few moments later, I could feel my pussy wall taking command of the dildo by grasping it as I shoved it in faster, and at that point, I knew I would agree to the wager.

After thinking about Dan's idea, it left me with a quandary. If it happens, it will mean our relationship will change but at the same time, I knew I wanted to fuck Robert. I took some time to think about what it would mean. After Dan came home, having some time to think thinking and considering it, I decided I was going to tell Dan my decision. I nervously approached him, "Are you sure of your wager?"

"I am not sure I understand what you are saying?"

"We do this as something fun between us and we never defined what was out of bounds for a wager."

"I know," Dan said, looking down and away from me, while taking a pause before continuing. "We have never formally discussed and I have always assumed that this was for a bit of a laugh. Fun you know, never forcing the other to go through with the wager if they were uncomfortable with it."

"I agree. I am afraid it could damage what we have and I am afraid that I might enjoy it too much."

"Enjoy it too much, a bird like you?" Dan begins to laugh. "You have always been a bit conservative. I think you will want to do it once just to see what it would be like and then the novelty will wear off."

At that point, I felt as though 1,000 people were staring at me that was holding onto every word I said because we never had this type of discussion before and I felt Dan knew me more than I knew myself. There was a long silence and feeling as though blood was facing to my face, Dan broke the silence by saying, " Do not worry, yet, the outcome is not known and I have some boundaries that need to be agreed before it goes a head for me." Dan took a long pause and I thought he was done speaking until he said, "I always felt there was something unresolved between Robert and yourself. Maybe because of your backgrounds, growing up in the country, or I don't know."

Shocked by the fact I am still open to idea; I prodded by asking what were the boundaries. "They would be it is a one-time thing, I knew when it was going to happen, and no communicating with him after it happened." At this point, I felt a flurry of feelings range from sheer excitement to being utterly upset. Feeling upset came from the uncertainty that it brought and the fact I have not fully resolved the conflicting beliefs I have about the wager. Whereas the excitement came from the fact I might be able to arrange for Robert to fuck me. Now, I could feel my nipples getting hard and beginning to feel moist between my legs. Dan then said looking at my chest, "I can see you like my response," with a smile on his face.

"So you are happy, if I try to find him online and contact him?"

"Yes as long as you are transparent about what you are doing, you keep me updated, and we periodically talk about it."

After the conversation, I went back upstairs and I was feeling confused. At part of me was wondering if Dan suggested this because he knew I did not keep in contact with any ex boyfriend and was confident I would not find Robert. Moreover, there was some doubt in my mind if I could actually go through with this if I found Robert. This left me wondering if Dan suggested this wager since it was more likely a fantasy than reality.

I decided to go downstairs to speak with Dan again and to confirm that he is comfortable with the idea. Speaking with him he says,"I know you feel this wage is a bit out of character for me; I know you still have a sexual interest in Robert and fucking him might do you some good. I am not going to push you into something you do not want to do." Silence fell for a minute and Dan continued, "I love you and this needs to be your choice, if you loose. If you want I will pick something else that is less threatening."

"No, I am alright with that. I needed to be sure in my mind that this was not a joke." With that statement, I left him and went back up stairs to begin my search. As I began my search by looking at various social media websites, it suddenly dawned on me, if I found him what would I say? I thought about being causal by saying, "It is a long time since we spoke," and then try working up to my idea. However, I thought that would take a while and I was trying to move things faster. This left me with a dilemma in determining the best way to solve this problem and after contemplating the idea, I came up with a solution. The solution involved me being the seducer by pretending to be someone else and once we meet surprising him. Being the one who is pursing him got me quite wet and feeling flushed, in a way it felt like a rush. Sliding my hands down my pants I could feel how wet I am becoming and spent a few moments imaging what I would be doing with Robert.

I looked up at the clock in our office said 10:43 and most of the morning has now passed. If I was going to find Robert, I needed not to let my mind wonder. After a bit of searching, I found him on a social networking site and he lived only 50 miles from us. A bit nervous, I tried to hide my identity when I made contact with him by sending him a message. Once I made contact I felt I took it as far as I could and hoped that he would respond. Instead of nervously waiting for a reply at my computer, I decided I would do a few errands then check back. It was about 14:23 when I checked my computer to see if I had a response and to my surprise, I did. Not sure, what my next step should be and thought, "How do I move this forward without appearing too anxious?" My heart was beginning to race and my palms became sweaty. Soon I was considering other questions in my mind, "Do I need to tell him that I am married? What is the proper etiquette?" After taking a brief pause allowing myself to calm down, I decided a video chat would be the best way to handle this and suggested it to him.

It took about 5 minutes before we could see each other and I was nervous thinking to myself, "Will he recognize me?" If he did recognize me from all of these years then I will not try to hide it admit but if not, then I will play along.

At first he said, "Hello," with a lot of tension in his voice and to me it indicate he was nervous.

I then responded with a confident and cheery, "Hello." There was a long pause felling as though it was 5 minutes but actually, it was no more than 30 seconds. Capitalizing on his nervousness, I could feel a sense of power in trying to achieve my conquest and being the one who is doing the pursing. Knowing I could capitalize on this moment my decision was to play an innocent but confident woman. This meant for me trying to flirt with him and then letting the conversation happen.

"You look like someone I knew a few years back."

"Really?" His statement told me he was not sure who I am.

"Yeah, I was attracted to her but we were young... Nothing developed and we soon went our own ways."

"What do you think you would do if you saw her again?"

Robert paused a few moments, a smile broke across his face and his voice had a child like innocence to it. The innocent sound to his voice told me, this is something he does not readily share with someone and he is being genuine in his reply, "We were young and inexperienced. If I did meet her again I guess, I would like to go all of the way with her."

Coyly I asked, "Have you spoken with her since then?"

"No"

"Are you sure?"

"As far as I know, I haven't."

"What if I told you, that you are speaking with her now?"

"Really!" His eyes were getting wide and I could see Robert was trying not to look too excited.

"Yes, I am married. However, my husband knows I am searching for you and there is more." At that point, I could see some of his excitement leave his face and a look of puzzlement enter. The look I would say is similar to someone playing a slot machine that is expecting to win big only to discover they won a few dollars. Noting the change in his look I continued by saying, "I can see you look puzzled and I will try to clear up some of the confusion. My husband and I like to bet and he bet, if he wins, then he wanted me to have sex with you? We are now waiting for the result since bet is based on an election."

"How you feel about that?"

Pausing for a few seconds to consider, my next words since what I say will determine if this goes forward. "At first, I went through a lot of different feelings but I soon discovered how much I wanted to fuck you."

"Okay, let me back-up a bit so you understand what is being considered." As our talk continued, I could see him again relaxing and I could tell from his expression that his interest remains. "What were are considering is either a threesome with my husband or letting me be a lone with you then telling him about the experience. So this is an one time chance to make it happen."

"The idea sound quite tempting... A lot has changed since we were younger." A long pause, "I do not know how to say this." I can see on his face is struggling to decide if he is going to say something. The look on his face reminded me a lot of a young child that broke something and is unsure if they should admit to it, "Well, here it goes... If we did go through with this, I would prefer the threesome option with your husband there."

"Okay, um, is there any particular reason?"

"After our relationship ended... I had a few relationships with both men and women. So, I prefer both... If you know what I mean?"

"You know I come from a fairly conservative background. Even though I have changed a lot over the years, I do not know if I am comfortable with that." My response to Robert was due to the shock of hearing he is bisexual. At this moment, in the back of my mind was, "How is Dan going to react? Will this force Dan to change his mind?" The idea of being with Robert sill arouses me and I want to this to happen. Before making any decision regarding speaking with Dan or telling Dan to consider another option, I decide I will ask a few questions. "When you say that you have been with both men and women are you now playing for the other team?"

"I am not sure that I understand?"

"I guess, what I am asking is do you only prefer men... Now?"

"No, I like women too but if the opportunity to be with a heterosexual couple came up then I would take it, if you know what I mean?"

"Okay, so if I understand you correctly, if there was a threesome with Dan and myself you would want to be able to interact with both of us?"

"Yes."

"So, when I talk with Dan what are you proposing that you would want to do with him?"

"I am not looking for anal with him. Instead, I am open to touching, oral, and mutual masturbation. If he is not open that then I am willing to have a completely straight threesome with him"

"I cannot speak for Dan and need to get his feelings on this. Will you be online later?"

"Yes"

"We are on vacation and he is home at the moment. Once we know the outcome of the vote and I have a chance to speak with him, I will let you know what he has to say."

"Bye for now." After signing off I thought to myself, "this whole bet is beginning to get complicated and almost unmanageable." I went downstairs seeing him watching television, approaching him I say, "You realize, I was speaking to Robert online while upstairs?"

"Really, what did the two of you talk about?" By his tone, I knew Dan was interest was more in me and I know my current ambivalent feelings about this will show through my conversation with him.

"Catching up on old times and what we have been doing since school."

"Anything ... else?"

"Well, we did talk about our bet."

"And..."

"He is definitely interested, but um... How do I say this," pausing before I continue. "Dan is bisexual and he wants to have a threesome."

"You are fucking kidding me!"

"No I am not."

"I don't do that. I am not a canary!"

"I know you are not and I told him that. Robert said, he was looking for some touching, maybe some mutual masturbation, and maybe him giving you a bj or you giving him a bj. I told him I would have to speak to you about it."

"Is he only into blokes or birds too? I am not going to do another bloke in front of you!"

"No, he is into both and is still attracted to me. He said he would be alright with it if there was no interacting between the two of you I would expect that he will interact with me too."