Chastity & dating from a Single Guy's Perspective

[grubber]

I got to thinking about this after hearing about a friend going through a divorce. No, I don't think he even knows about chastity but I do know that he is nervous about being single and dating women all over again.

Anyway I know from a married man's perspective that most of us have been in a vanilla relationship before chastity. Once this fetish got into our heads, we had to figure out a way to talk to the wives about it and hope that they would agree. We were married almost 30 years when I discovered chastity and it still took a lot of courage to even bring this up to my sweet wife. It's incredible how little people in a vanilla relationship talk openly to each other about their sex lives

So you're single and learned about chastity and it's something that you want but you don't have a keyholder. You may even wear a device. Now you meet someone that you like. Really like. At what point would you bring up chastity if ever? On the first few dates? Wait until your relationship grows? After you get engaged or married if you ever get that far? Would you wear your device when with her without her knowing?

[Tom Allen]

Years ago, a friend of a friend mentioned that his "timeline" is about 3 dates before he mentions that he's kinky to a new/potential partner. He likes to get it out of the way ASAP, so before they waste a a lot of time, or get into having (vanilla) sex, and all those other relationship issues, he tries to get an idea if she would be up for it, and if so, then by the third date he lets her know that he's kinky, and has some fetishes that he would prefer to explore.

[locked4her55]

If chastity play is that important, IMO I wouldn't wait till it progressed to the engagement stage.

My wife, who now embraces chastity, have talked this over before. If I had brought this subject up early on in our courtship it would have been a game changer in her opinion.

I believe early on it's ok to test the waters to see how the conversation it is received, but tread lightly if you get the "wide eyes" OMG.

[Tom Allen]

I believe early on it's ok to test the waters to see how the conversation it is received, but tread lightly if you get the "wide eyes" OMG.

You'd have to make some kind of determination if you could live without kink. You could well find yourself engaged to someone who is completely averse to the idea, and then where would you be?

You could look at this as an ethical question, and ask if it is unfair to spring this on a partner after a couple of years, potentially wasting everyone's time.

[locked4her55]

I believe early on it's ok to test the waters to see how the conversation it is received, but tread lightly if you get the "wide eyes" OMG.

You could well find yourself engaged to someone who is completely averse to the idea, and then where would you be?

You would be a "closet kinkster" and probably not very happy.

[Tom Allen]

You would be a "closet kinkster" and probably not very happy.

And that's why my friend discloses by the third date.

[Len51]

I preferred to find out during the first meeting if the woman was interested in either doing or trying my fetish. My experience is that if someone did like the idea of my fetishes on the first date, they were not going to change their mind on subsequent dates. I needed to know that they were at least open to the idea and not disgusted by it or no more dates. It is not difficult to find out what their feelings about a fetish are. I would find a chance to laughingly say that she should be spanked for what she did or said, and then see her reaction. Sometimes they would agree or even say that they preferred to spank me. If they began suggesting that we have sex, I would feign concern and ask them if they intended to tie me down and have their way with me. The best was when a woman I met at a bar told me to kiss her ass for a comment I made and I said that I would love that. We ended up in her hotel room with me performing analingus and cunninglingus on her all night.

It worked for me. My three long term relationships were with bisexual, kinky and submissive women. I was engaged to the first, cuckolded and dominated by the second and married the third who brought her best friend into our bed for 38 years. Her girlfriend liked to dominate me in bed at when we were in the mood.

[Happily caged]

I got to thinking about this after hearing about a friend going through a divorce. No, I don't think he even knows about chastity but I do know that he is nervous about being single and dating women all over again.

Anyway I know from a married man's perspective that most of us have been in a vanilla relationship before chastity. Once this fetish got into our heads, we had to figure out a way to talk to the wives about it and hope that they would agree. We were married almost 30 years when I discovered chastity and it still took a lot of courage to even bring this up to my sweet wife. It's incredible how little people in a vanilla relationship talk openly to each other about their sex lives

So you're single and learned about chastity and it's something that you want but you don't have a keyholder. You may even wear a device. Now you meet someone that you like. Really like. At what point would you bring up chastity if ever? On the first few dates? Wait until your relationship grows? After you get engaged or married if you ever get that far? Would you wear your device when with her without her knowing?

As for myself, I certainly wouldn't make her my Keyholder until marriage, but beyond that I would have been quite open about it.

[Schwink]

I've told the past three girls that I've dated quite early in the relationships about messing around with things like chastity, crossdressing, anal play, and femdom. It never changed any of the three relationships. All three essentially said "I wouldn't mind trying out X" but stayed away from the rest. Granted, I haven't had a chance to have a keyholder, but I have done things like facesitting, going out in drag, wearing panties/bras in the bedroom, and oral with an added toy in me. In my experience, people have ideas in their head about sex that they just want to try. It just takes some effort to find someone with the same ideas and some openness.

[grubber]

My three long term relationships were with bisexual, kinky and submissive women. I was engaged to the first, cuckolded and dominated by the second and married the third who brought her best friend into our bed for 38 years. Her girlfriend liked to dominate me in bed at when we were in the mood.

I have to say I'm shocked Len. I thought way back in those "olden days" when you started dating, men "courted" women and did things like hold hands while thinking pure thoughts.