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 only50 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?”
“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?”
“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?”
“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.”
“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.”
“Okay let us see the outcome of the vote and if I am the winner, then I can talk with Geoff about this since he tells me a bit his threesome adventures.
Election Day was 5 May 2011 with publication of AV results on the evening of 6 May 2011, we followed the returns online and AV was soundly defeated. After it became apparent that AV was defeated, Dan said, “Why don’t you contact Robert to let him know the outcome? I will contact Geoff to get some input but do not agree to any meeting, yet”
“I can, but don’t you think it would be better for me to speak with Robert first?”
“You are not agreeing to meet him but let him know I have won the bet. Tell him you
might have an answer for him in a few hours and if not, no more than a few days”
“Yes, let me know the result of the conversation.”
Dan left the room so that I could have some privacy with Robert and not have a background conversation while speaking with Geoff. I found Robert and suggested that we once again use personal messaging with video. After both of us finished logging in, I stated with a smile and jokingly said, “Dan won the bet and is looking to collect.”
“I see…” Robert had a big smile on his face and deciding to tease a bit, I remove my pink night top exposing my 34B breasts. “Very nice.”
“I thought you like… Are you going to help Dan collect his bet? Or do I need to find someone else?”
“No, I will definitely help him collect.”
“Great, he is a bit uncomfortable with the idea of having contact with you and he is talking with a friend who has had threesomes with men. I do not believe he will change his mind on it and I might know a bit later this evening, will you be contactable?”
“Yes, I will and if I am not online send a message and I will get it the next time I sign in.” Before I could tell Dan about my conversation with Robert, he left to speak with Geoff.
“When I knocked Betty answered and direct me to the basement. I have not seen the basement since you finished decorating it. You all right, mate?”
“Yes, you said you wanted to discuss something with me?”
“Here it goes, mate. I thought I would ask you since you are always telling me about your threesomes with Betty.”
“Well you see, I bet Jenny if I won we would have a threesome with her ex-boyfriend. He was a bit of a wanker at university and I do not see him as a threat. Jenny spoke to him and blimey it turns out that he is a bit camp.”
“So, he is playing for the other team? Gay?”
“Oh no, he likes birds too but I just don’t know what to think. I have a chance a threesome and being able to watch Jenny enjoy herself. If I say no then I don’t know if I will have another chance.”
“A few general points about having a threesome.”
“Okay, then tell me.”
“First point, nothing happens in a threesome unless you agree to it, which means ‘no’ means ‘no. Second point let him know you limits and the farthest you are willing to go. Third, you can have a threesome with it being straight and no male on male contact.”
“So, what you are saying is the threesome can happen without turning me into a canary?”
“Are you open to doing anal with him?”
“Okay, this defines a limit for the activity and I suspect he will understand if you do not want contact?”
“According to Jenny touching does not have to happen.”
“There is three options for you if you decide touching is fine. One is you taking a hold of his cock then helping him to enter Jenny. Second, the two of you could masturbate each other in front of Jenny. Third could be sucking him off or him sucking you.”
“I do not think I want to go that far.”
“If you want I can take off my jeans and you can have a go at feeling my cock. It will give you an idea of what it might be like”
“Won’t Betty mind?”
“No, we have an open relationship”
“Are you sure you are alright with me touching your cock? I am not sure what to do.”
“Don’t think about it, just go with what you feel and watch my body to let you know if I am enjoying it.”
“Alright… I guess. Do you want me to take your pants off or do you?”
“I will, give me a moment as I unzip my jeans and slide my underwear off. What do you think?”
“I did not think you could get hard that fast. I did not know you were that big.”
“I never told you about my fantasy of you stroking my cock.”
“Come closer, so that I can feel your cock. It feels hard but the skin is quite moist, not what I was expecting.”
“Oh, yes that feels good, faster.”
“No offense Geoff, I cannot go through with this and thank you for helping me work out what I need to do. I am going to leave, now.”
“Jennifer are you home?”
“Yes, give me a minute. I will be right down!”
“Did you speak with Geoff? What did he have to say?”
“He gave me some insight into having a threesome and I learned that I am not into male on male contact.”
“So, what are you saying then?”
“I am not sure… I think I am saying that I would like the threesome to happen but I want to watch, not participate.”
“Are you sure, that is what you want?”
“Alright, I will contact Robert and make the necessary arrangements.”
Jennifer logs on to her instant messenger. After logging into the instant messenger, Jennifer sends Robert, “Hi I am online 😀 and spoke with Dan about the bet. Let me know when you’ll be online so we can discuss further.”
With no response Jennifer is about ready to log-off when she receives an instant message from Dan, “Hi, was not sure if I would be able to chat with you.”
“I was about ready to log off.”
“Dan did some thinking and is not comfortable being with another male.”
“Oh darn, I was looking forward to meeting him.”
“You will meet him. He said he wants the threesome but wants to watch.”
“Oh really, that is super.
“It is getting late, I am getting tired, and I need to get up early. We will talk some more tomorrow and make arrangements. Bye for now.”
After signing off with Robert I thought to myself, “I am going to see if I Penny is online so, we can chat and get her opinion on this, I am going to send her a quick message to see if she responds,” Jenny thinking to herself. “Penny, I need some advice, can you chat?”
Knowing it might take Penny a few minutes Jenny waits and is about ready to sign-off when Penny responds, “Is anything wrong?”
“No, I am confused and thought you might be able to help?”
“Are you and Dan having problems?”
“No, the advice I want regards threesomes. I know you have said that Charlie and you occasionally have threesomes. Well… I have an opportunity for something like that; however, I am not sure about it.”
“What are you unsure about?”
“Long story short, you remember Robert from university. Well, Dan bet me sleeping with Robert if he won. He won but I found out Robert is bi; Dan wants to watch, not participate but I am not sure.”
“You remember our sort-of bi experience back at university? I don’t think that will change anything about Robert and I always felt Robert was attracted to you. Though I never believed he was not straight.”
“I guess what I want is Dan participating and I feel, if he is not participating then it takes away from the experience.”
“The experience is wider than Dan and you. It is about being desired by two men at the same time and them pleasing you. Even though Dan may be watching he is still there with you and enjoying seeing you enjoying yourself.”
“I know, that is why I am still considering it. In my mind, if Dan is not participating then I feel it is cheating.”
“It is not cheating, as long as both of you agree and the threesome does not go beyond what is agreed. From what I remember of Robert he did not seem to be someone that would destroy a relationship or go beyond any limits set.”
“I don’t fully agree with your definition of cheating that but I do understand what you are saying. Have you even done a threesome before where Charlie just watched?”
“Yes we have. However, I need to leave in a few minutes; I will save it for another time. Let me tell you from experience, if Dan believes you are enjoying yourself, he will be too horny to control himself and will join the two of you.”
“What you are saying I should go ahead with this and Dan might join in?”
“Great, bye for now. Bye.”
With that, Jenny signs off her computer and speaks with Dan. “Dan are you awake?”
“I have been doing a lot of thinking about what you said and I am willing to go through with it.”
“Great, make sure you let Robert know,” Dan said with a tired voice.
“Trust me, I will. I am going to email Robert”
Going back to her computer Jenny boots it up and sends Robert a quick message, “Everything is a go, contact me to make plans.”
“It is getting late,” I thought to myself and I will arrange with Robert in the morning and after leaving the computer, I went to bed.
The morning of 7 May 2011 is sunny with very little clouds and warmer than usual. I awoke at 08:00 with Dan still asleep in bed. That morning I made a light breakfast before taking my shower, and seeing if Robert replied. Logging into my account I find Robert replied, “Glad to see things are moving forward and I am available on Saturday. Let me know the details, Robert.”
After reading that message from Robert, I knew things would be moving fast and if things worked out then by the end of the day, he will be fucking me. Responding back to Robert, “Available today too. Let me know your availability.” Still being early in the morning, I did not expect Robert to respond immediately back. I decided to enjoy the quiet that existed. It was around 10:00, I could see that Robert was available. “Hi,” I sent to Robert to see if he was at his computer or away.
A few minutes later Robert responds, “Hi, so it looks as though it is a go?”
“Yes, it is. To be honest with you, I am a bit nervous and still a bit unsure.”
“Don’t worry Jenny; nothing is going to happen unless you want it to happen. I am not going to push you to do something that you are not ready to do nor will I do anything that will hurt your relationship with Dan.”
“That is good to know. Before going forward I do want to confirm what is being planned in order to prevent any confusion. It will be a one-time situation with Dan watching but I suspect if he gets horny enough he may want to participate.”
“I can live with that.”
“Also I am not sure where my comfort level lies, at the moment.”
“Again, that is fine. If you ultimately decide against it or if I perform oral on you without having sex, I can live with that.”
“What are your thoughts about meeting, tonight?”
“Since you live in a small town, I do not want to attract attention, and I am assuming you do not want to attract attention either, I was thinking meeting in Redman City, Iowa. We could each book a hotel room at the same hotel and then meet for dinner.”
“Sounds good, but it will take us a few hours to drive to Redman City. It also means I need to pack and get Dan moving. My feeling the earliest we will be there will be around 17:00.”
“If you send me your cellular number, I will text you the hotel and my room number.”
“I will bye for now.”
Trying to make it to Redman City by 17:00 meant I did not have much time to waste since it is close to 11:00, I have to get Dan moving, pack, and try to leave by 13:00. Luckily, Dan was finally moving about, though still groggy from sleeping, “Hun, I spoke to Robert online and we need to leave.”
“Watcha on about?”
“We agreed that we would meet in Redman City about 17:00, we would book a hotel room and he would book a room at the same hotel too. He is going to text me the hotel and restaurant. So there is not much time to yammer and we need to get moving.”
“Flippin’ell we need to get a move on.”
With that said about 20 minutes later Robert texted to me the hotel and restaurant, I texted back, “So far we are on schedule and should be on the road by 13:00 or shortly thereafter, see you there.” After, the text I booked a room at the hotel and I finished getting ready. It was about 12:30 when Dan & I started packing for our weekend getaway. Dan picked up my dildo that we sometimes use to simulate another cock in me and said, “Do you want to bring this with? Otherwise it might feel left out?”
“I think I will be getting enough attention tonight and I don’t think I will need it, tonight.” With that, Dan walked over embracing me, kissing me on the forehand, and then said, “I love you, I think we are going to have fun tonight.” With that, we grabbed our bags and loaded the car. Once we were on the interstate heading towards Redman City, Iowa I texted Robert, “On our way and should be there in time.”
The next four hours in the car was quiet and I am not sure the reason. It could be that we needed the time emotionally, to prepare for the evening, or that we did not want to say something that would ruin the evening we had planned. In either case, the ride seemed longer than usual. When we arrived at our hotel, the sun was shinning and the sun felt warm on my skin. Once we were at the hotel, I texted Robert to let him know we arrived and gave Robert our room number 1023 and he texted me that he had a poolside room. I did not pay much attention to the room since the evening was going to be busy we started to get ready for supper. As we were getting ready for supper Dan said to me, “How do you want to play supper tonight?”
“I am not sure what you mean?”
“We have two options tonight, one option if everything goes alright we will come back to this room with Robert. Second option, I was thinking maybe, if you wanted you could back to Robert’s room alone?”
“I sorta like the second option but I do not know how I will feel until we are at the restaurant.”
“How about we come up with a few signals?”
“Okay, like what?”
“When we are ordering I will ask if you want a glass of wine with supper, if you want it to go forward you will say no and if you want don’t want it to go forward you will say red.”
“That is easy to remember, what about the rest of the evening?”
“After supper, if you want to go to Robert’s room you will say, I want to go. If you want a threesome, you will say lets head up or if you don’t end it then say, we need to leave early so I can prepare for my meeting on Monday.”
“That is a bit confusing, but I think I might be able to remember.”
“Main thing, you need to be subtle about what you want. Otherwise you will tip him off.”
“Gotcha.” The signals that Dan gave me helped me to let Dan know my feelings about where things are going without being obvious about it. The next two hours went by quickly and by about 19:15 we were ready to meet Robert. After closing door to our hotel room behind as the closing of the door reverberated through the floor it left me feeling both fear and anticipation. It was not until the elevator door opened and heading towards the restaurant in the hotel, I began feeling horny with many thoughts running through my mind. I was wondering what it will be like to be desired by two men at the same time? Will Dan be all right with this? Will I choose the threesome or choose to be alone with Dan? Dan and I arrived before Robert. Luckily, this gave us a few minutes to talk before Robert arrived.
“Regardless of what happens tonight, I want you know that I still love you, Jen.”
“Remember, to go through with this or not, the final decision lies with you. Unless I get really uncomfortable with the situation, I will not put a stop to it.”
A few moments later I could see Robert by the Maître d’ trying to find us. It is difficult to see Robert’s features from a distance. Once I get closer I can see he still has a youthful look to him though his hair is thinning on the top and his build is less athletic that at university. “Nice to see you,” a Robert embraces me and gives me a kiss on the forehead.
That kiss made my heart race and made me wetter, trying to hide my trembling voice, I said, “We are over here.” Robert and I arrive at the table and I introduce him to Dan. There is a few moments of awkward silence until Dan says, “Hey mate, glad you could join us on short notice. How about a pint?”
Robert, at first appears not knowing how to respond to Dan before taking a few moments and saying, “Not sure what you mean?”
“InEnglandbeer is served in pint glasses and much stronger, not the wimpy stuff they serve here. I believe in the States an English pint is20 ounces?”
“I am not picky, surprise me.”
“What do you want Jen?”
“Nothing for me, I fine right now.”
“I will be back in a few.” By Dan getting the drinks I knew he was trying to set the right tone for the evening, checking to see if I want this to go ahead, and give me a few minutes alone with Robert. Trying to break the silence I ask Robert, “How have you been?”
“I have been all right, a lot has changed.”
“I suspected that.”
“I have thought about you a lot. I am glad you are here,” after saying that Robert bends forward kissing me on the cheek.
I respond by placing my hand on his inner thigh and looking into his eyes by quietly saying, “I know.” The intensity of the moment started my heart racing again, I began feeling warm all over, and I was feeling quite aroused. For a moment, the room felt as though it was spinning, I felt weak, and at that point, I knew my decision.
“Are you alright?” asked Robert.
“Not to worry, I will be fine.” I did not want to tip off Robert what I was thinking and I wanted to wait until Dan came back to let him know what I have planned. Looking towards the bar I could see Dan paying for the drinks and I started caressing Robert’s inner thigh some more. As I did, I began moving my hand towards his balls and cock. The look on Robert’s face told me he was enjoying it. Once Dan came back to the table I said, “I want to go.”
I could see Robert’s face drop until Dan said, “I has been a long drive and I would like a drink before heading back to the room. Hey Mate can you do me a favour and take the misses back for me?”
Taking my hand, I gently stroked the outside of his hard cock, as Robert said, “sure.”
Dan and I did not plan this scenario. In order to make it look as natural as possible to Robert I said, “Dan was mentioning to me while you were getting drinks, some photographs he wanted to show me from high school. I know it would bore you. Do you mind if I see them.”
“Have fun, I will see you back at the room.”
The walk from the restaurant to Robert’s room was short walk from the restaurant since they were on the same floor. His room was a bit smaller than ours and it was noisier since it was poolside. Nonetheless, the noise of kids yelling, people jumping into the pool, and the running of the air conditioner to remove some of the humidity from the pool provided enough background noise where chitchatting became difficult. Robert sat on the chair by the table that leads out to the pool. I sat on the edge of the bed facing him. Looking at Robert, I could tell he was nervous and not sure what to do. He tried to talk about school but the nerves got the best of him. I knew if I did not do something soon then this whole journey would be a waste. “Look, Dan knows what we are doing here. My statement to Dan done in order not to tip off the other people what we had planned. No need to be nervous Dan’s know what we are about to do. He was the one that suggested it to me.”
“Yes. Dan and I do not do this all of the time… It is sort of a special thing this time. Now, are you going to get out of those clothes or do I have to rip them off of you?”
Robert then stood up and began undressing putting his clothes on the chair. As he did this I walked over to him putting my hand on his chest and began caressing his upper body before drawing him in close. Drawing him closely I took my right hand to feel his cock and I began kissing his body as I worked my way down to his raging hard-on. “I like what I see,” I said before taking his cock into my warm wet mouth. “Mmm…” I moaned and as I did, Robert began thrusting his hips. At this point, I knew he is getting excited; I stopped, and guided him to the bed. After getting him to the lay on the bed, I instructed him to lay there as I undressed for him. Crawling on top of him, I took control by holding down his arms as I brought myself down so that I my face was in front of his cock. “I want you to be a good boy and follow my instructions, can you do that?”
Robert nodded his up and down, signalling that he is willing to be compliant. “I don’t want to leave without being sexually satisfied because you cannot follow instructions.” I then proceed to take his shirt, rolling it up, and made a crude blindfold from it. “I have made a very crude blindfold since I do not items that would make a better blindfold. Your punishment for removing the blind fold will be me leaving. You don’t want me to leave, do you?”
“No,” Robert said quietly.
“Good, I want you to lay there. Do not play with yourself and do not cum until I tell you to cum.” There was silence from him and I knew he understood. I began sucking his cock, again, but this time as I sucked him I began caressing his balls.
I then rolled Robert to his side, spanked his bottom, and said, “That was a warning not to cum. Hopefully, I do not have to give you another warning and if I do, I will stop for 5 minutes.”
“Okay, no need to be so rough.”
“You’ve wanting my pussy for about 20 years, you want to know what my pussy feels like and you want to know what it is like fuck me. Soon you will find out but before you get to experience your nirvana you must demonstrate you are worthy.”
After that exchange with Robert, it told me he lacked experience with women and it indicated to me that he probably was more into guys. I realized at that point that I made a few assumptions that I probably should not have made and decided not to take this foreplay much further.
“Are you ready to cum?” I asked Robert
“How badly do you want to cum?”
“Really bad, it is difficult to hold back.”
I crawled back on top of him, grabbing his cock and inserted into my moist pussy.
He easily entered, “Oh god you feel incredible, nice and tight.”
Finally, having Robert inside of me made me feel 20 years younger and the time seemed to melt away. His cock felt a lot different from Dan’s. Dan’s feels narrow and long. However, Robert feels thick and able to enter all parts of my pussy. As I begin to move, I can feel Robert’s cock growing larger in me. Looking down at him, “Don’t move, let me do all of the work.” Now, I have control of his cock and I began moving my hips in different directions in order to stimulate different areas of my vagina. As I looked down, I could tell by the expression on his face that he was close to cumming. “Are you ready?” I said in a loving and gentle way.
A few more thrusts I could feel him filling my forbidden fruit. I bent forward, waited for him to go soft, before kissing him and climbing off him. Lying next to him, I realized I did not want a round two and I had a chance to explore something that I felt that I missed 20 years ago. “I need to go. Hopefully Dan is not thinking I have become too engrossed in photos,” winking at him to let him know I was joking. With that, I got up, kissed him on the cheek and got dressed. “Keep in contact. It was nice seeing you again.” I said this as I was opening the door to leave. After closing the door I knew the biggest part of the night was going to be when I get back to the room with Dan. The fact that I did not orgasm with Robert was not an issue since I knew Dan would make cum many times.
Waiting for the elevator, I grab my room key and press the button for the 10th floor. I use the card to open the door and Dan is lying in bed and the room is dark, “Did you enjoy yourself?”
“Yes. I think I might have enjoyed it more if you were there.”
Dan sits up and motion for me to join him on the bed, “You wanted to go back with him and I felt it might work out better if you did.” Sitting on the bed with my back to Dan begins to massage my shoulders and rubbing my back, “I bet you are sore from your workout.”
“Let me, release some of that tension for you.” I turn towards Dan and begin kissing him swirling our tongues around and feeling desired. It is difficult to describe but as Dan kissed me it felt, as though, we were closer. As we kissed, Dan began cupping my breast and playing with my nipple. He then began to undress me before guiding me to lay down and as he did, he kneeled in front of me. I could feel Dan moving down me, and I began trembling with pleasure. “I see you have been a bit of a trollop tonight. What are we going to do about it?”
“What do you think we should do?” playfully responding to Dan.
Dan pushing on my shoulders against the bed pushes up and says, “I cannot let this behavior go unnoticed.” Soon I felt Dan stroking my clit with his hand and eating me out. “Don’t stop what you are doing, it feels so good.”
“Did he have a big cock? Bigger than mine?”
“It felt different. He felt thicker but I cannot say for sure larger.”
“What did he feel like, in you?”
“He felt wonderful.” As I said that I could feel Dan enter me.
“Did you cum?”
“I wanted to but I couldn’t.”
“All I can see his him fucking you and you enjoying yourself.”
A few more thrusts I could feel Dan explode in me, filling my hole.
Dan went limp, climbed off me and we fall asleep in each other’s arms.
We both lay in bed until 09:00 and prepared to check out. The ride home we spent time talking about our hopes for the future and talked about what we would like to do with our lives. After that night, Dan and I connected at a much more emotional level. As a couple, we have considered trying this again with a stranger but I will have to see if we go through with it. As for Robert, I tried to contact him a few times to see how he was doing but I have not received a response from him. If you were to ask me, would I do it again? I would say yes but with changes. I know for some this experience maybe seen as cheating but for Dan and me it has worked miracles. From the journey I learnt, wishing for something to come true means, the path is not straight but filled with many unexpected turns.