Chastity and Dating Viewed by an Unattached Man

After hearing about a friend going through a divorce, it made me ponder this. I don’t think he even realizes what chastity is, but I do know he’s anxious about being single and re-entering the dating scene with women.

From my viewpoint as a married guy, most of us had standard relationships before embracing chastity. Once this fetish took hold in our minds, we needed to find a way to discuss it with our wives and hope for their acceptance. I was nearly 30 years into marriage when I found out about chastity, yet it still required considerable bravery to bring it up with my lovely wife. It’s amazing how little couples in vanilla relationships communicate openly regarding their sex lives.

So, you’re single, have discovered chastity and desire it, but lack a keyholder. You might already be wearing a device. Then you meet someone special—someone you really like. When is the right time to introduce the topic of chastity? Is it during those initial dates? Do you wait for the bond to deepen? Or do you mention it after engagement or marriage if that milestone ever arrives? Would you keep your device on while with her, keeping it a secret?

A friend of mine mentioned years ago that his "timeline" is roughly three dates before he reveals to a new or potential partner that he's kinky. He prefers to get it out of the way quickly, avoiding wasted time and diving into (vanilla) sex along with other relationship dynamics early on. By the third date, he lets her know he has some fetishes he'd like to explore.

If chastity play matters that much to you, IMO I wouldn't wait until the engagement stage. My wife now embraces chastity, and we've discussed this before. In her view, if I had raised it during our courtship, it would have been a game changer. I think testing the waters early on is fine to gauge how well the conversation lands, but be cautious if you see those "wide eyes" of surprise.

> member_56a3d51043 wrote: > 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 need to decide whether you can live without kink. You might end up engaged to someone who absolutely dislikes the idea, leaving you in a tough spot. Consider this an ethical issue: Is it unfair to spring this on your partner after a couple of years, potentially wasting everyone's time?

> member_381064b05f wrote: > > member_56a3d51043 wrote: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'd become a "closet kinkster," likely not very happy about it.

> member_56a3d51043 wrote: > > You would be a "closet kinkster" and probably not very happy. That is exactly why my friend discloses by the third date.

I liked to find out during that first meeting whether she was interested in either doing or trying my fetish. In my experience, if someone likes the idea of my fetishes on the very first date, they stick with it. I needed assurance that they were open-minded and not disgusted by it; otherwise, there wouldn't be any more dates. It isn't hard to gauge their feelings about a fetish. I'd find an opportunity to jokingly suggest she should get spanked for something she did or said, then observe her reaction. Sometimes they agreed or even preferred spanking me. If they started hinting at sex, I’d pretend worry and ask if they planned to tie me down and take charge. The best moment was when a woman I met at a bar told me to kiss her ass for a comment I made; I replied that I would love doing so. We ended up in her hotel room where I performed analingus and cunninglingus on her throughout the night. It worked well for me. My three long-term relationships were with women who were bisexual, kinky, and submissive. I got engaged to the first one, was cuckolded and dominated by the second, and married the third, who brought her best friend into our bed for 38 years. Her girlfriend enjoyed dominating me in bed when we were both in the mood.

> member_d99507a7e8 wrote: > 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 me, I certainly wouldn't make her my Keyholder right away before marriage, but otherwise, I would have been very open about it.

I've told the past three girls I dated quite early on that I mess around with things like chastity, crossdressing, anal play, and femdom. It didn't change any of those three relationships. Essentially all three said "I wouldn't mind trying out X" but stayed away from other aspects. Granted, I haven't had a keyholder yet, but I have done facesitting, going out in drag, wearing panties/bras around the bedroom, and oral sex with an added toy inside me. In my experience, people already have ideas about sex they want to try; it just takes some effort to find someone who shares those ideas and has openness.

> member_1f25a48511 wrote: > 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 admit, Len, you shock me. Back in those "olden days" of early dating, I thought men "courted" women and did things like hold hands while keeping pure thoughts.

> 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. And with a chaperone always present, of course.;)