Seeking Cuckold Advice

Hello,

It has been a very long time since the last time I was involved in anything involving cuckolding or sharing partners. It was pretty much in my past and expected nothing in my future.

Since then I got remarried about 6 years ago to my wife Jen and although I shared my past with her she was not the type of person that would delve into the lifestyle. She was good enough to allow me to share my stories with her and let me interject them into our intimate moments.

In the first year I would get her curious enough to ask me questions about Cindy and Nat. She couldn’t understand how any of this was possible and even more so, how I would be ok with it. Jen was a very jealous woman and it just didn’t settle well with her.

In time I found out that right before we dated, she had been seeing a guy named Nick. As it turned out he was the reason she had a box of Magnum condoms at her house when we first met though, at the time, she insisted they were there for her friend that would use her house from time to time.

I am definitely not anywhere near using a Magnum sized condom but it didn’t upset me. Instead, it got me turned on and became exciting trying to get her to talk about it.

It wasn’t until she was a little loopy on some sleeping medicine that she blurted out that his was the best cock she ever had. We were in the heat of the moment and I kept asking her about him when she divulged that little nugget of gold. She claims she didn’t remember saying it but there was no way I would forget.

Over the next few years he became a fairly consistent topic during sex. She knew that talking about him was a real turn on and I never hid it. I would ask her detailed questions and would have her think about him while having sex. It wasn’t too difficult because as it turns out, theirs was a real physical chemistry of which she couldn’t get enough sex. I could tell the times I would bring him up, Jen was more turned on, wetter, and had louder orgasms even when she tried to deny it. It was obvious.

I then began to ask her if she would ever text or call him and she adamantly refused. I would tell her how much of a turn on it would be but it was a no-go. I then confessed that the thought of her and someone else was a real turn on. She would bring up imaginary affairs into our sex play but I kept steering it always back to Nick.

One night in the heat of passion I somehow convinced her to message him and simply say, ‘thinking of you’. I couldn’t believe it. The next day I hear Jen in frantic tones saying something about him responding and why this was such a bad idea. She said she knows him and knows what he is thinking and how this was so bad. She insisted she did it only for me but didn’t think he would respond. Jen ended up sending him a humorous reply to quickly diffuse the situation. Turns out she was really afraid also because he was mutual friends with some of her family and friends.

I asked her why she was so scared and she said, and I quote, “We had this chemistry and it is very dangerous”. I asked what she meant and she explained that she knows she would not be able to resist things happening.

I let some time pass before bringing it up and I mentioned that he obviously knows you are married (I met him once before we got married … but I didn’t know their past) and he still responded thinking it was a flirtatious text. She acknowledged that fact but insisted that it was never going to happen. She said, “I’m not going to fuck him so stop asking”. Needless to say, I didn’t bring him up again.

Two weeks ago Jen wanted to use her toys to get off and afterwards wanted to focus on me. In the middle of everything she tells me that she thought of Nick during her orgasm and even though we weren’t supposed to bring it up, she didn’t want to lie. I found that a little suspicious because I would never have known. Part of me thinks she missed me talking about him and turning her on. In any event, it was a good night.

Last week in the middle of another hot night, I mentioned that I call Nick under the pretense of hiring his firm for some work and was going to meet with him. She didn’t stop me so I went on and said that she was welcome to join for lunch or whatever it turned out to be. She mumbled some things alluding to the fact that I was lying but I insisted I wasn’t. Holy shit!!! She began to make out with me like she just met Ryan Reynolds (her secret love).

I asked her if she was going to come and she said yes … then maybe … then yes. Never once stopping her increased passion. She whispered in my ear that I didn’t know how dangerous this was but what I never heard her say was that I should stop it. I have never seen her so turned on and cum so wildly.

Afterwards I confessed I hadn’t really called him and she said she was relieved but I didn’t believe her. I asked her if she thought it was real and she said she didn’t at first but then was convinced I did. I know she was uncomfortable for a moment realizing she let her desire unguarded.

So this is my dilemma. I actually ended up reaching out to Nick two days after and talked to him on the phone under the before mentioned false pretense of hiring him for work. I mentioned that Jen had mentioned him several times regarding his work. He said he hadn’t talked to Jen for so many years and was thankful that we thought of him. He was going to work on the proposal and send me the details via email.

AND THAT WAS IT!!

I’m torn in what I should do. Part of me was thinking of telling Nick about Jen’s thoughts about him and see if having a ‘casual’ meet could lead to something. Or maybe not clue him in and just convince him that I would like to meet in person (even though there is no need for it with regards to this job)? Should I let Jen know or should it be a surprise?

You would think after my past I would have this down pact but I must admit I don’t want to ruin this opportunity.

Any suggestions or feedback would be greatly appreciate!

markmonacco@gmail.com

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