You're certainly a very logical cuck Cali, It does actually make sense about the CHORE aspect considering we've been together for so long. And yes, you are right there of course that the emphasis has to be on her and her enjoyment in finding other guys to date. What I think is going to be hard for me, at least initially, is that she plainly said last time, that she doesn't want the hassle of having to fuck me anymore as its always a disappointment and a chore for her. So basically I head into this lifestyle losing the ability to have sex with my wife. I don't want to put restrictions on this, but I wonder if I can negotiate something here or should I just try and accept that from the get go? The above is why I see chastity as such a vital ingredient so I can't cum and don't immediately get the jealous/horrible feelings. I actually raised chastity last time and she was open to it so perhaps it's something I can raise up front again this time? That's really nice that you have that kind of relationship with your wife where you're so understandable of her needs, and she says she has a deep love for you. The difference for us compared to your situation is that we don't have any kids so she'd be free to do whatever she chooses when she chooses to do it.

Thanks again for your thoughts Cali. It helps to hear what you're saying and it makes sense. I felt initially that she had already started feeling emotional bonds towards the escort , but that was clearly nothing, and will be a lot more if and when she started dating. I mean just from the point of view of she was getting her hair-done a different way, lingerie shopping, chatting to the escort and giggling and generally just seemingly so happy that she's going to fuck a hot guy. That's the thing, I don't consider myself gay and don't feel gay. I still love looking at the hot girl at the office or supermarket, etc but I know I would enjoy crossdressing/being a sissy. I wouldn't know how to satisfy the hot girl even if I somehow got her anyway. I know its perhaps unfair to say, but I don't want to lead her down the cuckold route again if she wouldn't allow me the crossdressing/sissy aspect. I was also thinking if and when I raise it all again of asking her to put me in chastity straight away, so I can't cum, and get the confusing thoughts again until after she's had sex with the escort. What do you think about that? Do you still have sex with your wife? It did hurt a bit when she told me she found sex with me a disappointment and a chore. I suppose a cuck should expect that but it still cuts.

Thanks for your response calicolombia69, really thoughtful, and some great points that really make sense to me. I think you hit the nail on the head when you said not to get hung up on emotions and understand that with 14 years together we've built a solid partnership. In your 20 years of cuckolding, has your wife always seen it as just and only sex or has she formed emotional bonds with her lovers too? How did you handle that because I think that would be the most difficult part to handle? A part of being so nervous about it all as well is that I want to confess to her that I want to be a sissy and that I want to solely wear womens clothing around the house. When we talked originally discussions came up about chastity and her saying she would probably want to be sexually exclusive to her eventual boyfriend. No probably about it really with her not looking at me in a sexual way, but I wonder whether it would totally kill her opinion of me if I mentioned the sissy aspect of cuckolding. Any thoughts there?

Thanks for your comments guys. The problem I have is talking to her again about it and her realising I actually want it and that I'm not trying to play a game. She was pissed last time so how do I avoid that again? I thought about saying to her to put me in chastity until after her first time so I can't cum and don't get second thoughts? She said she would go to the escort's place for the first time, and if she liked him, would do a second all-nighter at our place before then starting to date.

I've had a cuckold fantasy with my wife for years and finally got the guts to tell her about it. Upon telling her and sharing what it meant and her doing her own research, she was really keen on the idea. She said she wanted to start with a male escort first of all and go from there. I suggested signing up on a site like ashleymadison and seeing what happens from there to find someone more regular and she sounded keen on that also. A week or two went by and she was busy getting her hair done, looking at buying sexy lingerie, etc and was really happy at the whole thought of it all. She found an escort she liked and was communicating with him about arranging a time. She was telling me she couldn't wait to have his big cock in her mouth and in her pussy. It shocked me because she's always hated sucking me. She later admitted to me that in the 14-years we've been together I'd never made her orgasm and that she found sex with me a disappointment and a chore. We were having sex on a particular afternoon and after I came (wasn't long) I got really sad and begged her to not go through with it and that my feelings were all over the place. Naturally she was pissed off and didn't talk to me for a couple of days and we had a fight about whether she cared for me at all and whether I'd suggested it in the first place just to test her. It ended up with us agreeing to never mention it again and to make more of an effort to enjoy sex together. We have been having more regular sex, and she's making an effort that's for sure, but I'm still struggling. The problem I'm facing is that I can't get her fucking the escort out of my mind now and I'm wanking so much thinking about it. The problem is that after I wank I feel all guilty and feel like I don't want it, etc. It's a circle I keep going through. How can I overcome these feelings and get things back on track?