Beginning Again

Hello there! It’s been quite a while since I last posted here, between my wife/KH passing away and me closing down my blog. That said, I’m starting to get back into the human routine as an exercise in itself. I am just beginning to venture out again; it won’t be long before I do more actively. Living by myself with not many people around for conversation makes dating feel like the best option right now.

So far so good on that front: I’ve met a lovely young lady, and our second real date is coming up this weekend. We seem to mesh well, enjoying both our chats and the time we spend together. On our first data (date), I made it fairly clear that I’m quite a kinky fellow but didn’t go into specifics at all. Left it open-ended. She appears pretty vanilla for now—also a widow—and isn’t planning on bringing up kinks until she feels ready to do so herself. My admission seemed to surprise her somewhat, yet since she agreed to a second date, our budding friendship wasn’t derailed completely. We touched upon several other “deal breaker” topics as well.

Most folks here have spent long periods in relationships before even mentioning chastity; I know I was one of those people myself. But some seem to have it woven into the fabric from the start. Simple question: How do you manage this? Neither of us is young, and we’ve both been through long-term partnerships that ended with a partner passing away. However, while I definitely have kinks, I’m not sure about hers—we haven’t quite reached that discussion yet.

It scares me stiff that if I get too detailed about it, she might bolt for the hills and block my number. But I really like her; I can’t stop grinning.

How do you start a relationship—hopefully one lasting—with chastity being part of the mix? Eddie (Tom, feel free to move this to the blog area if more appropriate)

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

Sorry, I have no idea. I've often thought about what I would do if my wife passed. I am certain, I would not try and make a vanilla woman kinky ever again. There were too many arguments. She's either willing to try it or she's not. If it's a deal breaker for you, then you need to find a way to discuss it. The fact that she didn't run when you said you were kinky is good. And really, on a scale of 1 to 10, I consider chastity to be a very mild kink.

> How do you start a relationship, hopefully a long term one, with chastity being a part of it? By seeing whether you are sexually compatible at the start. If she runs for the hills, then you were not compatible. It happens. Be true to yourself. If chastity is part of your sexual identity, there's no reason to hide that. You'll find someone who likes the game.

First of all. Welcome back. The first word that comes to mind is Gently. There are a lot of ideas about chastity. If you're going to bring it up start with your version of what turns you on. Don't suggest she looks it up on the Internet. I have unfortunately lost two wives to Lukemia and pancreal cancer. So the relationship I have developed over the last 20 years is both sacred and terrifying for me as I live with a fear of loss. Ill be honest. C wasn't my type, but she was interesting in her own zanny way fun and full of life and wouldn't allow me to be miserable. She was in fact quite annoying and treated me like a sad lost stray which is in her nature. She is also Catholic and I am a proof and fact guy. We would never work but she stuck around despite my being a sad bloke. I'm glad she did. Turns out she was too good to be true and still is to this day. It took 16 years to broach the topic of kink and I belive it still nearly sent C to the hills. Now that's a loss I really wouldn't allow. C means more to me than any kink or need I have. Harder people might say "If she isn't what you want, ditch her". But you won't know if she is what you want or need until you really get to know her and visa versa. At that point maybe kink will be an option maybe not. But maybe it won't matter. You don't stop loving someone simply because they don't tick every box. Whatever happens I wish you all the best. Try to remember you deserve happiness, even if it isn't the shape you expect it to be.

Thank you for the reply Mr Pickle, it means quite a bit. I dont have 16 years to wait to broach the subject, I am in my mid 60's now, and so is she. I have opened the door, just a sliver, just a tad, and have touched on the idea of kink very very lightly more than once. She isn't pulling back, which gives me hope. I could go slower I suppose, not mention it at all for another year or so (assuming we get that far), which might be best, but I am a very open and honest person and dont want to lure her into a relationship that is going to end up failed because I was not open enough, or worse far to open. On another site I have likened this journey to trying to thread a needle while riding a camel, and honestly she may never move from being vanilla at all. But your right, happiness is the over-riding goal, and I can be happy without the kink involved if necessary. I like this woman, a great deal, and am looking forward to where it can lead. We shall see... Eddie

Cheers Eddie. You have something on your side I had to wait the 16 years for. The mind opens as we grow older. The mind is pretty flexible when we're young and anything is worth a try. But those middle years are a whole Box of caution and responsiblity as we learn to be 'proper grown ups', parents and we're under societies preasure to behave. But at our age.. We've gone through so much we don't care as much what society wants and very little surprises us. Also worth noting this isn't strictly a 'kink'. Not if you ask C at any rate. Maybe there is a better word for it?

LOL, afraid you are going to have to be the one to ask her, you know her better than I. Yep, I pretty much could care less what others think, but that is NOT true of my new young lady. I care a great deal about her thoughts, and how to broach the subject has been weighing heavy on my mind. IS it a "kink"? My therapist says it is, and they specialize in kink, so I am inclined to take their word for it. But on the other hand it's a small one, one that involves my partner quite a bit (at least it should) but does not really require being unclothed for her to engage in that kink. We have talked about being open minded, and she is receptive to that idea, knowing full well that I am referring to some kind of kink even if I dont get specific. I'd like to hash out some small specifics about it eventually, but this is a slow process I am on and in order to keep this budding relationship alive I am avoiding some subjects completely. Eventually that will have to change of course, but all in good time. I'd like to have her hooked before I start reeling in the line.:) Eddie

This is a tough one. On one hand you definitely would like to be a little deeper into the relationship before bringing this up. But on the other hand I can see it being appropriate to lightly broach the subject of what your kink is, how you see yourself practicing your kink, and what part she would play in this. I think I would approach it in general terms very broadly to start with, then get as detailed as her questions required. And unless it is a deal-breaker for you, I would definitely let her know that this is not a deal breaker issue for you and that you can set this kink aside if need be. Good luck with whichever route you take and keep us posted

A couple of random thoughts. If you haven't already done so: Maybe try to find a way to reassure her that this is not a heavy duty kink, not S&M with her suspended upside down, legs spread wide, getting her crotch ferociously whipped. Oops, got carried away there, but you know what I mean. Let her know that yours is a kind and gentle kink with significant fringe benefits for her. You might try learning about her past sex life. Maybe try to get her talking about one or more of these kinds of subjects: - On a scale of 1 – 10 (1 being not much interested, 10 being very frisky), where was her libido when at her sexual peak vs nowadays. - How sexually adventurous was she / is she on a scale of 1 – 10. (1 being missionary position only, 10 being extremely adventurous / kinky.) - Frequency - Ideal number of orgasms per month during her sexual peak compared to nowadays, keeping in mind that a lot of women, unfortunately, have never experienced an honest-to-god, toe-curling orgasm. - Ask her to name some things, if any, that still turn her on, or what her favorite foreplay activities are. Maybe have her rank her top 3 sexual positions. - Is her pubic hair ungroomed, trimmed for length, trimmed into a landing strip or other design or shaved? - How does she feel about receiving and giving oral sex? No way, don’t care for it, like it or love it? - Does she own any sex toys, e.g. vibrators, nipple clips, handcuff, dildos? - How does she feel about tying up (or otherwise restraining) a partner vs how she feels about being tied up (or otherwise restrained) and / or dominated by a partner: Her thoughts on any of these subjects could be enlightening. And . . . if she does not want to talk about any of these subjects, that might also be enlightening.

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.

@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

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.

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 key. 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.

> LuckyEddie wrote: ↑Sun Nov 26, 2023 9:58 am > 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 ginge**r 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.