Cuckold Chronicle (True Diary)

My Girlfriend and I have been dating for almost 3 years now and over the last year and a half I have discovered how much I love the idea of being cuckold. Unfortunately I have not had the chance to actually experience it yet, but the fantasy alone has allowed me to reach new heights of sexual excitement. Many thanks to the great stories posted on here.
Well, after lots of discussion and talk my GF has decided to entertain the idea to some degree. For all I know this may go nowhere, but I thought it would be fun to chronicle it here as things progress. Last night she put herself up on two different dating websites hoping to possibly find a man that interests her. Fingers are crossed for now.
Here is a little back ground anything else you guys want to know just ask. Kelly, my gf, is 45 (but looks 35) is 5’7’’ and about 130lb. She works out like crazy so she has a very sexy athletic body. She has three kids but you would never know it to look at her. When she tells people she has kids people automatically assume they must be very young, and are startled to find out that the youngest is 15. She has the most amazing breasts. Many thanks to one of the best surgeons in the country her tits are so sexy and real looking. The only thing that gives them away is that no one her age has breasts that look so good. She has a lovely face and shoulder length blond hair. She gets looks just about everywhere she goes. So finding guys interested in her will not much of an issue, but finding a guy she likes is the hard part. For the most part she is a fairly conservative woman so this will be a big step out of her comfort zone not to mention mine.
I don’t know how much you want to know about me but I am much younger then her at 25 and a high level athlete. I’m 6’2’’ at about 225lb. Because of my athletics I travel a fair bit.
I will update this as much as I can. Advice and comments welcome.

Well I have to say that I am shocked with the amount of response Kelly has been getting on these online websites. I had no idea that she would get so flooded. The first day she said she spent a fair amount of time just sorting through all the responses she received. So far it seems the number of guys that don’t appeal to her far out weigh the number that do. I suppose this was to be expected.
Well nothing has really come of any of it so far, she has started to chat with a three different guys over the last 2 days. One of which she seems to have more of an interest in then the other two. But I still think we are a ways from seeing it go somewhere. I have been encouraging her to enjoy her time and it seems she is. She has had to do a lot of work at her desk lately and she laughs at how it helps her pass a boring work day. Wish I had some more exciting news so far, but what can I say this is real life and real life always seems to go much to fast or much to slow for our liking. Ha-ha.

Wow, I will just say here that Spank’s post totally rocks. If you haven’t checked it out then you really have to. Here is the link:

https://www.cuckoldplace.com/2_42883_0.html

I just hope my diary gets to be on that order at some point. Slowly but surely. Well I am traveling for 2 weeks right now so will not be at home. While my news today is not huge (especially compared to the post linked above) it is still really exciting for me. Kelly is meeting one of the guys she has been talking to online for lunch. I wish I could say that this was going to turn into some wild and exciting romp but I know my girl and I know she wouldn’t jump to that but it’s a huge first step. They’re meeting for lunch tomorrow downtown at some place near where he is working. The guys is just a little younger then her at 43, but that’s still a lot older then me and that really drives me wild. I will let you know exactly what happens tomorrow.

I know my girl and I know she wouldn’t jump to that


Oh, don't get too confident about that. She's already agreed to meet a man while you are away. He might be very dominant and sweep her off her feet. That's what she wants anyway.

Where are you located? If you are accessible over the net, then you should have your wife's lover post pics for you as he is doing your wife. Another great idea if you are away if for your wife to put you on speakerphone as another man makes her cum. Good times!

Sorry I didn’t get this up yesterday. The place I am staying at needs a day to set up internet in the rooms. Go figure. So she called me right after the lunch and told me all about it. They went to a small soup and sandwich place down town and chatted for almost an hour. Sounds like the guy is really charming. They didn’t really get into much about sex in their talk; public places aren’t the best for that I guess. But she liked him and says that they are going to meet over the weekend or possibly early next week. He walked her to her car where he was aggressive enough to kiss her and they ended up making out for a few minutes at her car. Kelly loves to kiss and she said he was very proficient. I know its not much, but to me this is through the roof exciting. She really hasn’t been all that excited about this or at least hadn’t shown it until now. She tells me she is really having a lot of fun and loves the fact that she feels desired buy two guys.
As more details come my way I will post them.

Hi Goodtimes618,
Yeah I know what you mean, you never know what is going to happen. Honestly her making out with him was more then I expected. I just meant that I had low expectations for sexual for a sexual outcome. She is a crazy, exciting, and sexy girl in bed with me, but this is very new to her and she is very reserved. Trust me it was never a confidence thing.

We are Canada so pics and such over the net are no problem technically, but she is defiantly reserved anyone taking pics of her in any way that could hurt her social reputation. I wish I could say we can expect pics but unfortunately I really don;t see that ever happening. The speakerphone thing is a great idea I will run it by her.

Thanks for you post, comment and suggestions.

Well my trip is going to be longer then I thought. So it’s frustrating to not be at home but also exciting in the light of Kelly’s current adventures. I don’t think I named the man in my previous posts so I will refer to him as Matt. (obviously names changed for good reamister)
So they ended up getting together for lunch again on Saturday. She invited him over to her house where she prepared a lunch for him. Matt was working in the area so it was convenient for him but also meant there was a time constraint on there visit. I was shaking as she told me the events on the phone. I am so excited. I guess I never really thought she would take things this far. After eating they sat on the couch and talked briefly before they started to kiss. Kelly loves kissing, and it is probably her number 1 turn on. He fondled her breast through her shirt and then went under it pushing her bra up and off her breast so he could touch them with his bare hands. He told me she was extremely aroused, both by what Matt was doing and by the fact that she knew I was going to enjoy hearing about it so much. Unfortunately he had to leave before things had the chance to progress much further. But he is working in the area all week and they plan to get together again sometime this week. Possibly even today.
I asked her if she is still chatting with other guys online and she said that she only has enough energy for this one at the moment. That seems fair to me. Well she is flying out to visit me in a week. I think the next time Matt visits her things will go further. So fingers crossed that it all goes down before she comes to visit me.