Concerned - Journey to becoming a Cuck

[Concerned]

My previous thread "Concerned I mat become a cuck" explained the journey my wife and I have been taking on the road to her sexual fulfilment, and my becoming a cuck. We do not have children, and Lisa is not currently on the pill. I don't use a condom, and one of the rules that Lisa has set as one of her ground rules is that any 'bull' she meets will have to use a condom. That rule, like others is subject to change.

Lisa has tried to call Tony, a guy she knew where she used to work, but they have not talked yet. We are thinking that he will call back in the next day or so.

Lisa has a friend, Jill, who is into the hotwife lifestyle, and is in the process of feminizing her husband, although I think he had crossdressing leanings before she started the feminizing process.

Lisa has been talking about her 'date' with Tony non-stop. She has said that she does not want fucking going on this time, but will let him know that the next date will lead to a hot sex session. She has talked about what she is going to wear, and wants to be sexy and inviting, but not slutty. A lot will depend on where they go eat. She wants it to be at a place where they can talk, but not too expensive. She has asled for my advice, and I have made a couple of suggestions, but all this feels strange. Suggesting a place for my wife and another man have dinner, discussing their impending sexual relations. WOW!

Somehow I wish this were already over and I was a cuck, but I know it WILL happen. It's just a matter of time.

 

[Concerned]

Tony phoned! They have set up their first 'date'. From what I heard of the conversation, and what Lisa told me as well, Tony was surprised to hear from Lisa, and tried to set the stage for this first 'encounter' to lead to a bedroom, but Lisa directed things towards just a dinner. I heard her half of the conversation, and heard her say "No, not a hotel restaurant. You're not getting me in bed this time."

Emotionally I was very much torn. Wildly enthusiastic that this first date was happening, sorta scared that Lisa would want to ditch me for Tony, and other feelings I couldn't identify.

They will be going out Wednesday night to a fairly nice restaurant. I won't have time Wednesday to post, but I will keep everyone up to date. I know it will happen. I WILL become a cuck. This IS what I want.

 

[Concerned]

Well, we almost had a stumbling block. When Lisa got up this morning, she was having second thoughts. She said that she was going to call Tony and cancel. She said something about not wanting to hurt our marriage.

I had to think for a moment. I know that I had felt like I was on an emotional rollercoaster - and this was BEFORE she is fucked by Tony. Is this what I really want? I decided that it IS what I want.

I told her that I REALLY wanted her to have the freedom to have sex as often as she wanted, and I said that I was SURE that it would make our marriage stronger. She asked if I was REALLY sure, to which I replied "ABSOLUTELY". I hope I'm right.

I keep on thinking back about the fact that she wants sex more often than I do. She says that Tony has the reputation of having sex with one woman for a while, and then moving on. It sounds like he doesn't want emotional ties (I'm hoping). I'll say more when I know.

In any event she is NOT going to cancel, but I'm think it's pretty clear that tonight is not the night that I join the club!

 

[mybuttplug]

Good luck tonight. I'm sure you will go through an emotional roller coaster while she is gone. Just try to keep your thoughts on the end result you are hoping to achieve. Keep yourself busy. The last thing you want to do is text her asking for updates and annoy her.

You've asked yourself many times if this is what you really want. You should feel confident by now that this is something you both want. This is an exciting time and I hope you enjoy the journey as much as we have.

 

[Custer Laststand]

Concerned,

Thanks for the update.

Lisa has a friend, Jill, who is into the hotwife lifestyle and is in the process of feminizing her husband, although I think he had crossdressing leanings before she started the feminizing process.

You could probably find out more about the origins of Jill's project to feminize her previously-rather-obnoxious cuckold by simply asking her about it — so, you might consider suggesting to your wife she invite Jill over again. Since you have a bet pending with Jill re. the outcome (or one of the outcomes) of this project, she would probably view it as reasonable for you to enquire further about it.

Lisa has been talking about her 'date' with Tony non-stop. ....

That's certainly positive...

.... She has talked about what she is going to wear, and wants to be sexy and inviting but not slutty.

Are you going to offer to assist your wife with purchasing her "sexy and inviting but not slutty" clothing? You could point out you'd be willing to offer her the advantages of your expertise (as a man)... and suggest that you view assisting her with preparations for her dates as an important aspect of your role as her soon-to-be cuckold.

Tony phoned! They will be going out Wednesday night to a fairly nice restaurant. .... I know it will happen. I WILL become a cuck. This IS what I want.

Cool... it sounds like your soon-to-be hotwife is on her way, and for you the uncertainty and anxiety of convincing your wife to make you her cuckold will soon be replaced by the uncertainty and anguish of the reality of being her cuckold.

Will look forward to further posts on your experiences...

—Custer

 

[Hank jones]

Let us know how you are doing when she leaves. And do keep yourself busy. Don't bug her. If you back out now she will likely not offer to try on your grounds or input. Male sure she knows you really want her happy. And this is so she can decide if she does need more or if she can live with satified from you.

 

[Concerned]

She is out to dinner with Tony. I would love to know more, but I had decided this afternoon that I would work on stripping some furniture, and that will take several hours, and is best done without stopping. I started as soon as she left. I figured she would be back by now, but I will not call or text her!

I will post again tomorrow.

 

[Hank jones]

Can't wait to hear how dinner went. And the furniture. Lol

 

[Concerned]

I will post more about the dinner and other things that went on after the dinner later. I will respond to Custer’s post first.

Custer, your posts are always appreciated. Your analysis and questions help to tie things together and suggest actions that may not have been considered and you are most helpful to those of us just starting in our journey in this lifestyle. Thank you.

As to Jill and her feminizing Fred, I have pretty much decided to avoid Jill when I can. She is not in a loving relationship, and is not being helpful to the marriage that Lisa and I have. I won’t discourage Lisa from seeing her. That would make Lisa upset with me. I will just try to minimize contact whenever possible. As to why she is feminizing Fred, I am going to ask Fred if he had previously done any cross-dressing or had wanted to cross-dress earlier in life. I think he probably had these tendencies and Jill is just pushing him further in this direction. Cross-dressing is something that really does not appeal to me.

On purchasing “sexy and inviting but not slutty clothing”, Lisa has quite an assortment of outfits, some of which clearly fit the bill. She decided to wear a top which clearly shows off her cleavage and her 36D breasts. She knows that’s an outfit that I think is super sexy. She also wore a short skirt with that top. She has some lace – hardly there panties that she also knows are a turn-on and selected those to complete the outfit. She was careful with her makeup. Not too much, but just enough to be alluring. That’s my girl!

Yes, there is no doubt that Tony will soon be thrusting his cock into Lisa’s very willing pussy. The emotional ride will begin soon!

 

[Concerned]

Lisa came home fairly late for just a dinner, pretty much as I expected. OK, later than I expected. It was about 10:30. Her hair was in disarray, and her makeup was certainly messed up. I asked her how it went, and she said, with a huge smile “FANTASTIC!” She came over and gave me a huge kiss and then sat down and started to explain.

Tony was in Lisa’s words “charming”. While Lisa expected no less since Tony did have a way with women in general, she was obviously impressed with him. He was a perfect gentleman throughout dinner, showing real interest in Lisa, her new job, the family, the activities outside of work, and asked all the right questions, and said all the right things. In my view, he was clearly trying to seduce her. In Lisa’s view, he was being a really nice guy. They did not talk about their relationship or about sex. That was to come later.

After dinner, Tony suggested that they go to a nearby bar. They decided to drive both cars, so that Lisa could easily drive home afterwards. That was where they got into some serious discussions. Lisa, understandably, could not remember the conversation word for word, but she said that Tony really opened up about his previous relationships. He had been married, and was now divorced. His ex-wife earned a great deal more than he did, and he was actually receiving alimony. It was a significant chunk of change, and he was determined to “make that bitch keep on paying”. For that reason he was absolutely determined to not form any emotional ties to any of the women he dated. This was music to my ears! Lisa was also happy to hear this. Tony said that when he could tell that someone he was dating was beginning to form emotional ties, he broke things off. Lisa recognized that this had happened several times during the time that she had known Tony. In any event, they started to talk about sex. Lisa said that she described what she liked in a man, and Tony said how much Lisa turned him on.

During this time Lisa said that they were in a booth, both sitting on the same side. She was a bit aggressive with Tony, she said, stroking his leg. He was also a bit aggressive, stroking her thigh. When she was saying this to me, Lisa was watching carefully for my reaction. I was pleased for them. She then told me that he started fingering her clit. My reaction was carefully supportive. “Did you enjoy?” I asked. “Certainly, silly” was Lisa’s response.

Lisa continued the conversation with Tony talking about her ground rules. It was interesting, because when she told me what she said to him it was “You have to use a condom – at least until I get on the pill and you get tested for stds.” That was not what she had said before to me. I pointed out the change. She said that Tony obviously looked disappointed when she said that he would need to wear a condom, so she changed things a bit. She said that it was HER ground rule, and she had not changed it in the heat of the moment. I am a bit concerned, but accepted things.

Lisa said that they talked a bit about me. She did not tell Tony much, just which I would not be a problem. I was OK with what she said.

They will be getting together next week. Tony said that he would call her to set it up. He said that he would reserve a very comfortable place.

I am enthusiastic, but also a bit scared. It sounds too good to be true. Is he for real?

 

[will2112001]

Oh Great. A good thread being ruined by spam!!!!!!

 

[vladdy]

Time will tell. Hopefully he does come through, this sounds like an excellent arrangment for him. He'll be able to get plenty of sex from your lady while not having to worry about her attempting to form a serious relationship with him. Additionally thats a two way street you don't need to worry so much about her becoming to attached.

I would like to offer one peice of advice to you, I'm not sure if anyone else has. But you should expect that if this gets going she will be giving a lot of attention to this other guy sexually and you may feel put out by her. So you should discuss how much sex you'll expect during the up coming weeks. But after the intial burst of energy wears thin things should even out.

 

[Custer Laststand]

Concerned,

Custer, your posts are always appreciated. Your analysis and questions help to tie things together and suggest actions that may not have been considered and you are most helpful to those of us just starting in our journey in this lifestyle. Thank you.

You're welcome. I appreciate your saying so.

As to Jill and her feminizing Fred, I have pretty much decided to avoid Jill when I can. She is not in a loving relationship, and is not being helpful to the marriage that Lisa and I have.

Fair enough...

I won’t discourage Lisa from seeing her. That would make Lisa upset with me. I will just try to minimize contact whenever possible.

I think that's wise. Your wife can reasonably consider it her right to decide who her friends will be, and she and Jill have known each other for a long time (evidently). If you try to "cut Lisa off" from Jill and/or other friends, she could interpret that as an attempt to isolate her and limit her ******** to points of view other than yours. That, in fact, is a traditional tactic of abusive husbands. It would not be likely to strengthen your relationship with your wife.

As to why she is feminizing Fred, I am going to ask Fred if he had previously done any cross-dressing or had wanted to cross-dress earlier in life. I think he probably had these tendencies and Jill is just pushing him further in this direction.

It would certainly be reasonable to talk with Fred about that since you're obviously curious about it. I suggest being cautious about making assumptions about his underlying motivations, though, then interpreting whatever he says as confirmation of your assumptions. One possibility, for instance, may be that Fred had never thought about that prior to Jill beginning to guide him in that direction.

Cross-dressing is something that really does not appeal to me.

Hey... don't worry about it. It's totally legal for a man to not want to wear, nor actually wear, obviously-feminine women's clothing.

Interestingly, though, women cross dress all the time in the sense that they wear pants, shirts, jackets, boots, and/or other items of traditionally-male clothing, but no one considers that out of the ordinary let alone weird or erotic.

On purchasing “sexy and inviting but not slutty clothing”, Lisa has quite an assortment of outfits, some of which clearly fit the bill. ....

Sounds good. On the chance she might want to expand her wardrobe in the "slightly-more-slutty" direction as she expands her relationship and begins fucking her lover-in-waiting Tony, you might keep in mind the possibility of offering her your services as an expert (i.e., a man) in assisting her with purchases and assessing the sluttiness-appeal of different possible outfits she might want to consider...

Yes, there is no doubt that Tony will soon be thrusting his cock into Lisa’s very willing pussy. The emotional ride will begin soon!

From your subsequent comments, it sounds like your wife's initial date was a "two-thirds triumph." That is, she went out with her lover-in-waiting and seduced him successfully. Now, all that remains is to fuck him so passionately it won't even occur to him to not continue to let your wife into his pants whenever she wants that.

My congratulations to your wife, and to you for acknowledging her sexual needs and giving her the necessary support to seek satisfaction.

—Custer

 

[Concerned]

Time will tell. Hopefully he does come through, this sounds like an excellent arrangment for him. He'll be able to get plenty of sex from your lady while not having to worry about her attempting to form a serious relationship with him. Additionally thats a two way street you don't need to worry so much about her becoming to attached.

vladdy,
Thank you for your post. I am confident that Lisa does not want to form an emotional tie, having said that, once they start fucking, we will see. Things do change when people start having hot sex with each other. It still feels strange talking about my wife having sex with another man while she is married to me!

I would like to offer one peice of advice to you, I'm not sure if anyone else has. But you should expect that if this gets going she will be giving a lot of attention to this other guy sexually and you may feel put out by her. So you should discuss how much sex you'll expect during the up coming weeks. But after the intial burst of energy wears thin things should even out.

vladdy,
I recognize that I might not be getting much, but then I don't need much. Lisa's sex drive is much greater than mine, so I am hoping that we will both be getting as much sex as we want, but not more. Maybe that's unrealistic, but it's my hope.

Concerned

 

[Concerned]

Custer,
Again, thank you for your reply. I do plan to take what Fred says with a grain of salt. Perhaps it would be good for Cindy to get Jill's perspective on his feminization.

Things have been quiet for the last day or so, but I expect big changes soon. I'm not real good with uncertainty, and that's what we are facing.

Concerned

 

[Concerned]

Well, some interesting developments. Tony called last night, and I was the one who answered the phone. He identified himself, and I simply said "I guess you'd like to talk to Lisa." He said something like "Yes, I'm glad to get to see her since we no longer work together." Had I been able to think quickly I might have said "Well, you'll get to see more of her now than you ever did before", but I'm not that quick, and it might have made him uncomfortable, and I am not looking to do that!

I gave the phone to Lisa, and they talked. I decided not to listen, as I did not want to make Lisa feel awkward. She told me later that they set the date for Monday night. They will eat at a pretty nice restaurant, and then "see where things lead". Lisa is quite excited, saying it feels like when I was a teenager anticipating a date.

Jill also called, and she and Lisa talked for a LONG time. Afterwards, Lisa told me that Jill wanted to renegotiate our bet. Since I have withdrawn my objections to Lisa taking a lover, she wants me to have to do something else. I would completely refuse, but Lisa is saying that it seems fair. I'm unenthusiastic. We will see what Jill decides that she wants.

I'm glad that the date has been set, and Lisa is really excited.

 

[mybuttplug]

Concerned,

I think you had partially the right idea earlier in this thread of avoiding jill like the plague. But I don't think you went far enough.

I think Jill IS a plague on your relationship with Lisa and I think that you need to have a sit down with Lisa and say "Look, now that the bet has kinda cancelled itself out, I really don't feel a renegotiation with Jill is necessary. In fact, I really don't want to have anything to do with her. I want you to do what you want and be friends with whoever you choose. You are a big girl and can handle yourself. This whole thing is for your enjoyment. Not Jill's kicks. I am not comfortable with the way she behaves or the things she does. This is about you and us, not her.". Or something along those lines. Make it clear that you are not telling her to break off the friendship with jill, but you want no part of jill. Jill is a cancer on your marriage. I don't think true good friends encourage each other to cheat.

As for what is happening with Lisa and Tony, that is exciting. I hope things happen the way you want and that it is everything you think it will be.

Good luck to you.

I disagree. If you start telling Lisa who she can be friends with, you will give her the impression that you can dictate who she can date. Remember this is all about Lisa's pleasure. At this point in the relationship you want her to be free to make her own decisions. You can have influence and let her know what your likes and dislikes are but she should be free to make her own decisions. If you trust her now, it will lead to her being more confident in her decisions and ultimately better communication between the two of you.

 

[Concerned]

falcondfw69 and MacNfries,
I very much appreciate your advice. It is difficult to see how an outsider influences a marriage at times. Lisa so much likes Jill, and wants me to like her friend. I will discuss the situation with Lisa the best I can and suggest that someone outside our marriage does not always give the best advice, particularly if their marriage is not a happy one.

Any suggestion that Lisa cool her friendship would not be welcomed, so I won't say that, but I WILL approach the idea that Jill is not the best source of counseling about how to have a happy marriage. I will assure her that I have no objection to her friendship, but I want to minimize my time with her. I'll also say that I don't want to keep her (Lisa) away from her friends, but I want to be careful about who influences how the two of us interact in our marriage.

Does this seem to you two to be a reasonable tact to take?

Thanks again. I am looking for advice, and I appreciate what you both have written.

Concerned

 

[Concerned]

mybuttplug,
Thank you for your comments. I agree that it would not be wise for me to say who Lisa can and cannot be friends with. Since she is taking more of the leadership in our marriage, that would NOT go over at all. I will suggest that Jill not have as much influence about how Lisa and I interact (and how Lisa interacts with her lover when that time comes). I will point out that Jill is not a happy person, and that we both want this whole cuckold/hotwife lifestyle to be pleasurable for Lisa. If she becomes an unhappy person like Jill, that will not be pleasurable.

Thanks again,

Concerned

 

[Hank jones]

Sounds like things are progressing nicely. As for trying to change the bet, I'd talk to the wife see if she has any idea what the change is? Personally I'd just say with your wife in the room 'what you do to your husband is up to you. But making a game and changing the rules cause you didn't get your way? Not fair.'
You've weighed your options and you and the wife are exploring them on your terms not someone else's. You both need to agree on that. Not one of her friends.

Good luck.
Hank