Starting Anew

[CagedKC]

Don't waste time. Neither of you need to invest in a relationship if it won't be fulfilling for you both. IG after a few casudayes you feel that you want things to go further, just be honest and tell her you don't want to hurt her later by surprising her with your sexual kink. Give her a copy of "A Keyholders Handbook" by Georgia I've Green. Assure her that if she has no interest in continuing the relationship knowing male chastity must play a significant role, you will understand. Then ask her to call you if she wants to meet again.

[LuckyEddie]

@WifeIsVanilla A couple of random thoughts. If you haven't already done so:

Well, I like the way you think, but at the moment most of that is a bit to deep for where we are. We are "kissing", and sometimes holding hands, but that is as far as we have gotten. Not even "necking". Because of the passing of my wife she is REALLY wanting to go slow, and has some issues in her past that also slows the process some. We have talked about my wife quite a bit, but getting her to open up about her past has been a bit more difficult, still to new in the relationship process I suppose. Eventually, we should be able to get there. That's assuming neither of us run across absolute show stoppers. I did make it clear, on our very first date, that sex cannot be an off the table thing. That's where my wife was, only on very rare occasions, and I wont live that way again.

But you bring up some very interesting ideas. Approaching it as more of a benefit for her (has a cheating partner in her past), and the fact that my biggest kink is "service" related (massages, back rubs, foot massages, shoulder rub/massage, as well as the significantly more intimate services, etc for her) is what I tried and failed with concerning my wife, but might actually work better with someone who does not have the severe abuse background my wife did. That and the "turn over of control" might be the perfect bait for the hook. We are on date #5 this week, and so far she has gotten plenty of flowers, lots of talking, some REALLY good food, and movies, we are progressing at about the rate one experienced in the 1970's, the last time I was actually dating.

I'd like to get into the areas you suggest, and if there are no real road-blocks on either side, we should be able to. Not in the very near future, but I suspect in the next month or so. Asking about her past, well she seems reluctant to open up about it. Not all that surprising really, most women seem to be reluctant to discuss past relationships, specially with a prospective new partner. I will open that clam slowly, and with great care, but open it will come.

As for the pubic regions, and I have given this a great deal of thought, I liken my preferences somewhat as I like my salads: Freshly washed, dressed appropriately for the occasion, and I don't like hair in my food. Personally, I am very well "manscaped", not just because of the cage but because I actually prefer it that way.

Eddie

[YesDear]

Having been around here for a while, you should know that you should let her know "What's in it for her?"
Tell her how much you like her, and by keeping you locked, she will know that she will ALWAYS have your attention.

Also, if she doesn't like the idea, is it a deal breaker for you?

Good luck for your future and I am sorry for your loss.

[WifeIsVanilla]

I agree with YesDear.

Since she had a cheating partner, one additional benefit for her would be that she could be very confident that you wouldn't be cheating while locked in a device for which she held the keys. Even if you were able to "pull out," the device would still be firmly attached to your testicles. Even if you could satisfactorily explain away the fact that a hunk of metal (or plastic) was hanging from your balls to another woman, intercourse would certainly be uncomfortable at best.

[addadayplease]

Wow, 265 views and not a single post. From that I can assume that no one has any more of an idea than I do. Sigh... I guess I will figure a way through this minefield. Suggestions would be nice, if you can think of any.

Eddie

I am not on this forum much lately.
I've been checking out "Chastity Mansion" a bit.
But I do like the lack of fantasy drive here...and the more married people that frequent here.
But my heart goes out to you as a widow, and I'd like to craft a brief response to you in the early mornings hours of Christmas Eve.

I'm so very sorry for the death of your wife and her husband.
I work with people at the end of life. I am not a funeral director, but very close to it. I hold the hands of people who are dying in the medical setting and I put my arms around the recently bereaved as they weep and go weak in the knees as they stumble down the hall toward their cars. There are few things in life comparable to the death of a spouse...no matter if the relation was 1,5,20 or 75 years. My sympathies to you...and her.

I am glad you have found each other at this time and are getting to know each other.
But I don't feel there is any way to fast-track a chastity key-holder.
You've only had a few dates so far...and she hasn't run away....so good for that.
I do think second love experiences can be much more intentional.
The above questions from @WifeIsVanilla are important for two adults to talk about.

I listen to the "Sex With Emily" podcast...and her advise is for people to have clear communication in a non-sexual setting.
Don't have those questions ready to go should you find yourself in an intimate moment together.
It would be good to reassure her that your kink is not as a "top" to dominate her...but as a "bottom" for her to dominate you.
You may need to help her learn the kink glossary of terms...she may not know what top/bottom, Dom/sub mean.
Reassure it does not include pain threshold explorations for her...unless she is into that.

It would be good to know if she is "vanilla", what type of vanilla she is.
(Please indulge a bit if ice cream metaphor here.)

There is French Vanilla...which might include lots of tongues (French kissing...get it?) French vanilla could include lots of French kissing, nipple kissing and sucking as well as both giving and receiving oral caresses.

There is Vanilla Bean...which has some dark flecks from the actual pods and they occasionally crunch on the teeth when eating. Sexually, what would vanilla bean be like? Perhaps some light bondage, a blindfold...some vigorous working over of the penis and balls, if you are into that king of thing.

There is "Vanilla...with sprinkles". (This is a phrase my daughter said one times when she was talking about her sexual relationship with her first husband - a marriage that only lasted 23 months, due to his excessive drinking.) Perhaps your chastity kink could be couched in this category. Chastity means a cage on your cock and balls, some teasing and denials for her, and orgasm for you when she wants to bestow one...and as many orgasms for her when and how she would like them. It need not be complicated. Sprinkles.

There is "Moose Tracks" ice cream..which is basically vanilla, with some peanut butter cups and some chocolate swirls. Sexually, this might include some lite anal play...for you and her. One need not go full erection and deep, pounding thrusts for anal pleasures...especially for those of us from 40+ year marriages...who are now 50-70 year olds. It could be a stationary butt plug. It could be a vibrator held there, while penis is stroked or clitoris is rubbed..

(You still with me?)

It could be Neopolitan. A third vanilla, a third strawberry, a third chocolate. Many kinky couple are not kinky on every sexual celebration. Like some medications, It is for "occasional use, only as directed." You might ask her for a upcoming date - whenever she is comfortable - to discuss sexual desires as they changed over the course of your lives: masturbation, locations, was her husband into any kinky play, how your wife was into kinky play and not and what you and she like now. Perhaps "intercourse every time" has given way to "intercourse when the ED pill is working well" and hand jobs and rump rubs and good vibrations most of the other times...with lots of kissing, groping and snuggles too.

And we don't enough time or space to draw analogies from the many other ice creams with a vanilla base: Cookies and Cream, Cookie Dough.

Perhaps she has seen or read "50 Shades of Grey" or has been exposed to some form of "Rocky Road" (to keep the ice cream metaphor going one more time) and she had no interest in that. One would certainly need to define vanilla and vanilla variations of the many sexual activities in the sexual universe...for certainly all vanillas are not the same.

]In my house our, the ice cream is usually one of the three vanillas our stores stock...but we keep chocolate syrup, peanut butter, malted milk powder and even some "hard shell" toppings on hands for variations. I do like a crushed butter finger candy bar as a topping...but I will let you draw your own applications from this practice. Think lubed finger play. One time we took candied ginger and some fresh ginger and mixed into some softened vanilla and then refroze it. That was memorable indeed. (And if you don't know what "figging" is...you might need to at least educate yourself...and proceed at your own pace, if at all.). I have also been known to make a quick lemon/sugar syrup which turns vanilla into something with some serious pucker power...which fulfills the delicious depths of my dessert desires.

Also in my house...now we stock some of the new "plant based" ice creams. (My wife's two cardiac stents has changed her dessert desires completely). Oat based, Coconut Milk based. There are some good ones out there now, and we are grateful. Sexually, there are times when changes must be made too.

So the question I pose for you both to discuss is: If you say your are sexually "VANILLA...as opposed to "Rocky Road0"...could you explain how you define your "VANILLA" It just might be "vanilla with chocolate sauce on nipples" or "vanilla with a coconut oil covered fingers" or "vanilla with mango flavored lube". We, the locked men of the world, just might all still be "vanilla, with a cock cage and orgasms under her control...and not his - and a desire to give her more frequent orgasms that she has ever dreamed was possible."

In sex, we all have our ideas of what is "normal" or "godly" or "good" and it is common for many to swim a lifetime in those calm sexual streams...but some of us just might dip a toe or foot or go rafting in the swirling, thermally-heated rapids of the "different" or "kinky" or "taboo" streams on the other side of the valley. (On our vacations, we try to search out natural hot springs...but don't get me started on that metaphor!)

Anyway...those are a few of my thought today for you, @LuckyEddie
Perhaps, in the weeks and months to come...you will both find that you are "getting lucky"...a lot...once again.
I wish you well as you both grieve...and explore the parameters and potentials of being in the arms of a new lover in the here and now.
I wish you a Merry Christmas tomorrow....and a Happy (and some horniness in it too) New Year

P.S. I write this while currently caged and will be for the "foreseeable future". Lately, I am having some nice chastity conversations and play with my wife of 40.5 years.

[addadayplease]

We are on date #5 this week, and so far she has gotten plenty of flowers, lots of talking, some REALLY good food, and movies, we are progressing at about the rate one experienced in the 1970's, the last time I was actually dating.

...

As for the pubic regions, and I have given this a great deal of thought, I liken my preferences somewhat as I like my salads: Freshly washed, dressed appropriately for the occasion, and I don't like hair in my food. Personally, I am very well "manscaped", not just because of the cage but because I actually prefer it that way.

Who knows...perhaps after your have explained to her the basics of chastity and your history in it...how you enjoy both the denial of you and the indulgence and service of her..

She just might say. "On our next date...I expect you to come locked in your favorite cage...and place the keys in my hands!
And you might say "May I kneel at your feet as I do so?"
And she might say. "Absolutely. I require it to be so. I'd expect nothing less."

Perhaps she may have always wanted to be "in control".

And then...you are off to the races.