My Road to Cuckoldry

[tmw1966]

I have been married for almost 19 years and although I have fantasized about sharing my wife since 1995, after I watched an episode on Playboy Eden series where the husband enjoyed sharing his wife, and I really got into it. I only shared my fantasy with my wife two years ago and it has been a hell of a ride since then. I started blogging about it on another site but stopped after a couple of entries, so I will copy those entries here and hopefully I will be able to bring my postings to the present time very soon. Here is my first entry:

This posting is two years old.

So I have had a fantasy for a long time and I finally shared it with my wife, doesn't mean anything is going to happen, but at least we are talking about it. We have been married for 17 years this November and have one beautiful teenage daughter; my wife is a gorgeous woman at 40 she still looks as good as she did when we first met and I still don't believe I actually married such a beautiful woman, I didn't have a good track record in dating before her. We are not a conservative couple by any means, we have done a lot of crazy things before we got married and early in our marriage including a 3-some with another woman and sex in public many times. Once a month we meet after work on a Friday for a drink and dinner sometimes it is just us and other times we have friends; about three months ago we were having a drink at a bar before we headed to dinner and my wife caught me checking out a good looking young woman who walked by, she jokingly commented that she was too young for me, I denied that I was checking the girl out, but my wife sarcastically said that she would let me sleep with that girl but added that there was no way the girl was interested. I suddenly thought that may be I should some how bring up my fantasy about her and someone else, so I replied to her comment that I would also let her sleep with a young stud, she responded that she prefers someone in her age group, late 30's to early 50's. Although, I was disappointed in her criteria as I have always pictured her with a young man in his early 20's, but I wasn't going to let that spoil the moment. So I indicated to her that I was serious, and she questioned if that was an excuse for me to find someone else, I told her I had no desire to be with someone else and that I fantasized about that for a while, she asked me about my fantasy and how I fit into it, she questioned if I wanted to be with her lover and I was shocked she went that far, and replied that just the thought of another man enjoying her turns me on, she leaned across the table and kissed me and said that may be we should leave it a fantasy. The conversation had become very serious and I guess I got a little nervous and it showed, my wife comforted me and told me not to be embarrassed and that she is never embarrassed sharing her fantasies with me and started listing her fantasies like being with a woman, and bondage and then she said here is an idea my be we will have a fantasy about a young dominant man spanking me and we both laughed, she didn't know that I had actually thought of that in my fantasies; she is really into bondage, which I am not into. After few minutes of silence, I said I would also like to see it, see you with another man. she didn't respond, but few minutes later she said that she will never fuck a stranger, she is just not into it and that she must like the person she sleeps with, I responded quickly that that was OK, then she asked if I was worried she would fall in love with someone else, I said I trusted her. She told me it wasn't about trust, she may get attached to someone and she wouldn't have control over that, "Are you willing to take that chance?" i didn't respond. Few minutes later I asked her, if she was still in the mood for dinner, "Hell yes. Did you say all that to get out of our dinner date?" she said as she grabbed my hand in a comforting way.



As we were waiting for our table at the restaurant a guy in his mid 40's with a woman in her early 30's came in, few minutes later my wife whispered as she was looking at the couple in my ear "He is my type", she said it with a naughty smile as gently rubbed the back of my head. I think I got the biggest hard on ever at that moment. After we sat down, I told her if she meant it, and she responded by telling me that we should keep it a fantasy. I told her to tell me what she liked about him, she told me that she was always attracted by middle age clean shaved dark skin white men appears confident and powerful.

We haven't talked about the subject again since then, but i need to keep the discussion going, just talking about it turns me on. May be tonight, I will keep you posted

 

[xena2000]

Why haven't you brought it up again? Two years is a long time since talking about fantasies. How do you feel about what she said getting attached to another guy? What if that happened?

 

[tmw1966]

Xena2000,
As i mentioned in the beginning of my posting, those events happened 2 years ago. A lot has happened since then I just didn't post it yet.

Stay tuned for more to come

 

[xena2000]

Okay I see the hell of a ride, sorry, continue on.

 

[tmw1966]

Christmas Party

This entry goes back to January 2010:

I blogged earlier about my fantasy of sharing my wife with another man and how I told my wife about my fantasy about 3 months ago. Last month we attended a Christmas party with my wife's company at one of the fancy hotels in the area, during the cocktail hour a tall man came over to where my wife and I were standing and introduced himself to me and shook my hands very firmly that it hurt a little, I believe he did it on purpose, and kissed my wife on the cheek as if they were best friends, the guy was in his late 40's very well built and had a petite woman with him. Few seconds later I realized that he (Jack) worked with Jaimie (my wife) but he works at another branch so I have never really met him before. After the introduction, he made a comment about our height difference which was enhanced by my wife's high heels, my wife is taller few inches than me in bare feet. After few minutes of silence, he asked if we had a table picked and we answered negatively, so he told us that he will go find us a good table, in the same time his female companion excused herself to go to the bathroom. As soon as they left, I asked my wife who was the A-hole and she told he was some Jerk from the Atlanta office, she said that she met him few times here in town or at the annual company meeting, she added that he had a reputation of being a womanizer and might have a drinking problem, she mentioned that he was divorced and that the woman with him must be a girlfriend. He came back few minutes later and told us that he got us a great table. We socialized with some of Jaimie's coworkers until the waiters told us to go to our tables for dinner I saw Jack signaling us to go his way so we went there and followed him and Michele to the table. When we got to the table he pulled a chair out for Michelle, skipped a chair, and then pulled a chair out Jaimie and he sat in the middle, so I sat on the other side of Jaimie. We all talked for a little bit, he told us that Michelle was the host at a restaurant that he ate at frequently and that they have been dating for few months, Michelle mentioned that she like us had a 17 year old daughter, so we talked about teenage girls for a bit. After we ate dinner, he offered to introduce Jaimie to some big manager and Jaimie was excited so they got up and walked towards another table they stood their with a bald older man for few minutes, Michelle and I got engaged in a conversation about the stresses of Christmas time. Few minutes later I looked towards where Jaimie and Jack were standing but they were not there anymore, I looked around the room but still couldn't see them and Jack is hard to miss, he is at least 6'3". It irritated me that I was unable to find them, but out of nowhere I wondered if Jaimie was making out with him somewhere, may be in his room as he was staying at the hotel, I got very irritated and jealous but was also turned on, I got very angry at myself for being turned on by the thought of my wife making out with another guy, especially with Jack, who I thought was a real A-Hole. They came back like 20 minutes later, I asked Jaimie where she went and she said that she stood in the desert line while Jack went to his room to get a presentation that he wanted to share with her and then they went to the lobby and ate desert while going over the presentation. Jaimie asked if I was OK, and I said that I was just worried about her. Nothing much happened that evening except that we swapped partners on the dance floor and I had excuse myself and sit down so that the erection that I developed watching Jaimie and Jack dance doesn't show, it was a huge turn on seeing Jaimie that close to such a big muscular guy.

On the way home I asked Jaimie if she went to Jack's room, and she got really upset and told me that if she wanted to fuck him, she would have a long time ago as he has always hit on her, there was silence after that for few minutes until she reached over unzipped my pants and started rubbing my cock and asked me in a flirting way if I wanted her to fuck Jack and when I got hard she said "I guess you do" and laughed as she unbuckled her seat belt and went down on me, she stopped half way and asked me if I thought Jack's cock was as big as the rest of his body, and I replied in a nervous voice that there was only one way to find out, she never responded until I came in her mouth.

It was an awkward night we didn't say much that night, and we both went straight to sleep, while I actually didn't get much sleep as I kept thinking about the mixed feelings of jealousy and arousal by the whole Jack thing.

In the morning and after my daughter went for a run, I got the courage and asked Jaimie if she had any plans to fuck Jack, she kissed me gently on the lips and told she only wants to fuck me and to just leave that other thing as a fantasy.

Anyway, they will supposedly meet again at the annual sales meeting in late Jan in Florida. I doubt anything will happen though.

 

[tmw1966]

Friday Discussion

I kept thinking about Jaimie and Jack for a while after I saw them dance at the Christmas party, it was very disturbing for me because I didn’t like the guy, but that made it more erotic. For the first time I started thinking I was a cuckold, I never defined myself as a cuckold before then, but the thought of an Alpha male that I didn’t like taking my wife was a huge turn on for me. Jaimie and I talked about my fantasy few times, and she was very supportive, not that she was ready to do it, but she listened to me and appreciated how I felt. She would occasionally tease me about it, we would be out and she would see someone that she liked and she would whisper in my ears that she liked him, or that she would do him.

One a Friday night in February or March of last year, we were out having dinner and she said to me that she is always the one pointing out which guys she would fuck, and told me that that night I had to pick her “Boyfriend”, I got very turned on by the word and I had no idea why, the thought of Jaimie having a boyfriend drove me over the edge. I looked around us and pointed out a guy who was in his late 20’s early 30’s, he was a stud by all means. Jaimie laughed and said he was not bad, but judging by the young woman sitting with him she didn’t think he was into cougars. I pointed a couple of other guys both were in the same age group and they were all very well built. Jaimie told me that if I was honest in answering all her questions, she might reward me well, and I told her I would answer any question that I had an answer for, but I explained that there are many questions that I personally couldn’t find answers for. Her first question was why was I interested in seeing someone with her, when I can have her all for myself? I told her that the thought of having a naughty wife was how it all started; the wife who put her sexual needs ahead of everything was just a turn on. She mentioned that all the guys I picked were younger, tall, and kind of big, and asked why would I want her to be with someone who is totally my opposite, I am 45 years old, short, weigh about 150 lbs, and wasn’t I worried that she will enjoy sex more with them than with me; I answered that the fact that another man can satisfy her more than was a big turn on for me. She mentioned that my fantasy could be driven by either a dominant behavior or totally the opposite, she said she could see a dominant man who wants to control his wife to the extent of making her sleep with other men, or a submissive man who wants his wife to control their relationship. She asked me if I wanted to be with her lovers as well and I said No, she told me to be honest and I answered no way. I asked her if she wanted me to share her lovers and she said “Yes”. I was so surprised, I asked why; she said it is so erotic to have both of us sucking some stud’s cock. I told her that that will never happen. She laughed and told me to relax, it was just a thought. She asked if the thought of her flirting with and teasing other guys turned me on, and I said “Of Course”. She asked me few other questions like close your eyes and think of your fantasy and tell her the first visual I had, I told her it was her and Jack. She was very surprised and told me that she thought I didn’t like Jack and I said yes I didn’t like him, but the thought of them together turned me on. She asked me what was she doing with Jack, and I told her she was sucking him, she looked at me and teasingly said that she would love to.
Towards the end of the night, She told me that the next day, a Saturday, we could go out and see if we can have some fun, but she added that she doesn’t plan on anything more than just flirting. That night we fucked like we hadn’t fucked in a long time, she guessed all my buttons and played on them during our love making. She kept telling me about her big lovers and how they satisfy her more than me. we must have made love like three times that night, not bad for a 44 year old guy at that time.

 

[hurtme]

that is so exciting. i cant wait for the next part!

 

[Lipper628]

This is a very hot post,, I love you you are moving it along,, Please if you could include me when you add to it.

 

[Custer Laststand]

.... We haven't talked about the subject again since then, but i need to keep the discussion going, just talking about it turns me on. Maybe tonight, I will keep you posted.

Good story, well written. BTW, if you were to introduce paragraph breaks your interesting account would be much easier to read. (Blank lines can be introduced as paragraph breaks... if you lose your paragraph breaks when you post... by using the "edit" function.)

Sorry about this minor carping. Just a suggestion...

 

[tmw1966]

Thanks Custer, I will do better in the next post. Hopefully I will get the time and enery soon to get this blog to the present time. I may have to try to be more brief.

 

[bonzo41]

Really enjoying your account. Don't feel like you need to make it briefer. Updates coming soon?