New Keyholder, here. Help a lady out, please.

Cecilia B

Cecilia B

Long term member
Jun 2, 2015
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I'm new to chastity, so I want to know if I'm doing it right. I've been with BF since Jan. He has a job that's mostly day. I'm an Assistant Mgr. at a major hotel here, which means sometimes I have to work nights for a week or so. I'm a lot older than BF and have a couple of extra pounds. Anyhow, I have some insecurity issues, here. If I'm working weekend nights, he still wants to go to this bar. I don't think he'd go there trying to go out on me, but you know, a few drinks, a smile from a lady closer to him in age and the rest isn't hard to imagine.

First, I thought of having wear my underwear, so if he took off his clothes in front of another girl, she'd freak out. I asked him to do it for my peace of mind, so he said OK. That was a Friday, before I left for work the next night, Saturday, I handed him more of my undies and asked him to put them on He said he wasn't going out that night. When I asked him why, he said he just wasn't into going in that bar with women's underwear on. I backed down, but he did call me at work a couple of times that night. I asked one of my girlfriends how I could get my peace of mind back. She suggested a male chastity device. I didn't know what it was, so she suggested a couple of sites.

I liked keptforher because of the security devices because I read where sometimes guys can pull out of the chastitiy belt. Anyhow, I showed it to BF and he said OK, if it will help your peace of mind. I used it on him only if I worked nights and he was going out, I put it on him just before I went to work and took it off when I came home. One time, I decided to get playful and told him I'd take it off only if he brought me to 5 orgasms first. He did it, I took it off him and we played some more. Another time, I told him if he really wanted to get it taken off, he'd have come to me wearing my undies and asked if he could bring me to orgasm first. He went and got dressed and did it.

I can get him to do things I don't think he would have done by using the chastity device as a bargaining chip. When he's wearing my underwear, he does things I don't think he ever would have done. He looked SOOO SEXY in my underwear that first morning I came home, I had to have him do that again. He's a swimmer and bike rider, so he shaves his body hair, anyhow.

Am I being deceptive, here? Should I be using the chastity belt to get him to do things? Since I know I can get him to agree to do things when he'd dressed in my undies, is it fair for me to keep it up? He's an honest guy, he's good for his word and he'd never twist my arm to get me to do anything. Am I treating him unfairly by doing what I'm doing? I like the chastity thing, dressing him up and the control it gives me, but should I use these to get what I want? Help a Lady out, please.
 
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Sounds like you are doing everything just fine to me. My only real comment is that the device itself wont help your underlying insecurities it will only mask them a little.

Find a way to talk to your boy friend and work through them but by all means enjoy your new love of chastity.

Remember that chastity play can very emotionally challenging with the build up hormones and sudden release of them. The last thing you want is an underlying resentment becoming an issue because of an emotionaly charged argument.

Also I would suggest googling the phrase sub drop.

Have lots of fun guys.
 
if your having these kinds of thoughts it might be best to have a discussion with him and see how he feels about all of it. you might be surprised how much he is also liking it. Chastity is really just a form of foreplay, so dont be too hard on yourself lol.
 
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It sounds like you're actually being very responsible with the whole thing but before you go any further I would sit down and have a very open and honest discussion about why you chose chastity. Most guys end up loving it but if you just randomly one day made him lock up and then required x amount of orgasms before he gets anything could cause a misinterpretation on his part. Where you're just reassuring yourself that he won't cheat he could be taking this as a sign that he was never good enough for you. If you plan on taking this further then it is only fair that he have some say in what happens in the new relationship dynamic being that it is HIS body and HIS appendage if he needs to take a step back and learn more about chastity, let him; if he feels uncomfortable with your requirements, compromise and find something that works. As I said before it sounds like you are taking an extremely responsible approach and I hope everything works out!
 
I agree: communication. Tell him what is exciting you and maybe get him on board with the project. Find out what his fantasies are and see if you can engage them. What you describe is all good stuff. Lots of guys here want exactly that. There is not a right or wrong way to do chastity. More that you can do it with good communication or with out.
 
Cecilia B said:
I'm new to chastity, so I want to know if I'm doing it right. I've been with BF since Jan. He has a job that's mostly day. I'm an Assistant Mgr. at a major hotel here, which means sometimes I have to work nights for a week or so. I'm a lot older than BF and have a couple of extra pounds. Anyhow, I have some insecurity issues, here. If I'm working weekend nights, he still wants to go to this bar. I don't think he'd go there trying to go out on me, but you know, a few drinks, a smile from a lady closer to him in age and the rest isn't hard to imagine.

First, I thought of having wear my underwear, so if he took off his clothes in front of another girl, she'd freak out. I asked him to do it for my peace of mind, so he said OK. That was a Friday, before I left for work the next night, Saturday, I handed him more of my undies and asked him to put them on He said he wasn't going out that night. When I asked him why, he said he just wasn't into going in that bar with women's underwear on. I backed down, but he did call me at work a couple of times that night. I asked one of my girlfriends how I could get my peace of mind back. She suggested a male chastity device. I didn't know what it was, so she suggested a couple of sites.

I liked keptforher because of the security devices because I read where sometimes guys can pull out of the chastitiy belt. Anyhow, I showed it to BF and he said OK, if it will help your peace of mind. I used it on him only if I worked nights and he was going out, I put it on him just before I went to work and took it off when I came home. One time, I decided to get playful and told him I'd take it off only if he brought me to 5 orgasms first. He did it, I took it off him and we played some more. Another time, I told him if he really wanted to get it taken off, he'd have come to me wearing my undies and asked if he could bring me to orgasm first. He went and got dressed and did it.

I can get him to do things I don't think he would have done by using the chastity device as a bargaining chip. When he's wearing my underwear, he does things I don't think he ever would have done. He looked SOOO SEXY in my underwear that first morning I came home, I had to have him do that again. He's a swimmer and bike rider, so he shaves his body hair, anyhow.

Am I being deceptive, here? Should I be using the chastity belt to get him to do things? Since I know I can get him to agree to do things when he'd dressed in my undies, is it fair for me to keep it up? He's an honest guy, he's good for his word and he'd never twist my arm to get me to do anything. Am I treating him unfairly by doing what I'm doing? I like the chastity thing, dressing him up and the control it gives me, but should I use these to get what I want? Help a Lady out, please.
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You've started off perfectly IMO. Of course you should get him to do what you want. That's what he needs. And it'll do you heaps of good too.
 
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Welcome and enjoy CM.

You mention a few extra pounds . Let you in on a big secret. ....

Only the picture editors of women's magazines like skiny girls.

Most men as in 99.99% prefer curvy girls as in real women.
Xx Wendy
 
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Thanks, all for the replys. I read a few of them, but after I came back, the site was down. I tried a few more times, but it was always down. I assumed it was gone, but a friend told me it was back, so I'm back.

I had the discussion with him, like the first couple of people told me. I did dress him up before I started the discussion because I saw he was more likely to do what I wanted when he's dressed like a girl. This was one of my questions, was I being fair to him putting him where he'd be more likely to do what I wanted even if he didn't really want to do it. I know him, and even if he gave his word like this, he'd stick to it.

Being new to all this, I think I put a little too much on him. I told him everything I wanted to do. Rather than tell me he needed to think about it, though, he asked me if I'd let him think about it. He did say I'd put alot on him at once and if he could please look up stuff about it to learn more and if we could talk about it after he learned more. I thought it was fair so I said OK.

I'm working days for now, so we get home at about the same time, he's usually first. He told me he'd looked up stuff and learned stuff and he was ready to talk about it. I asked him if he'd get dressed first, but he said quite firmly he wouldn't, and he even knew the advantage I had over him when he was wearing my underwear, so I thought this was going to be a disaster. I got a drink and braced myself for the worst.

I was relieved. He said OK to the dressing up and chastity belt for now. Shortly after we started seeing each other, he told me he liked porn ( I asked, he told). He was always open with me, he's never tried to hide anything. Porn and playing with himself is something I really don't like. I've told him I rather he'd get his thrills from me than that. He told me I wasn't always available, which was true, but he could at least try to wait. I told him all he ever had to do was ask and I wouldn't say no. One thing I wanted to use the chastity belt for was to control him playing with himself. He said OK to that as long as I didn't abuse it. He did agree that the ' all you have to do is ask' could be suspended when he was in chastity. He could ask to be released, then everything would be back to normal. Another thing was when he had to go to work, release is automatic, because it's not practical for him to wear it at work.

He asked me to hold off on the spanking, cum eating and strapon. Let him get used to all this at his pace, which is reasonable. He wanted to keep this private for now, but didn't rule out clubs or even doing some of this in front of friends.

He made some limits which I thought were OK. No cuckolding, which I wasn't considering anyhow. No blood, OK. No guys getting to watch, ever, but if it's a club or party, it might be different, but we'd have to talk about it, first. Safewords, absolutely. He said he didn't need an 'emergency key' since he had tools he could use to get it off if he had to. He said some other limits, which I was OK with, but I'll get into these as I go along.

He did say I could order some panties for him I want him to wear but I don't have and a maid dress and little girl dress. He said he'd wear them for me. Usually he wears my underwear since I have alot of it that fits him. I have to keep a couple of sizes of clothes, since my weight goes up and down a few pounds. I've even put some of my dresses and skirts on him. I like retro stuff, so I have alot of lingerie I like him to wear.

So it looks like it's going to work. Maybe not as fast as I like, but he's never thought too much about this before he says. I'll give him his time.
 
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Hi
CM can take a bit of a holiday at times but it always comes back.

I love the bit he has to go and look up what you are suggesting omg xx
Any chance your sub is a bit vanilla or just a beginner.

Anyways wish you well .

Xx Wendy
 
As someone who started out very naive ten years ago, you are off to a great start. As others have said, communication is the key. Our case started for a different reason(infidelity), but I can remember before that when dickie started asking me about him being in chastity when I was out of town. He even arranged a dinner with a couple own a high-end sex boutique and practice bdsm. Best advice I ever got from the wife of the couple. Find out what you both are looking for, then off you go and learn from trial and error. Have fun and enjoy it...
Mistress Suzan
 
Only by communication will you really be able to learn what he is inclined to like. For example, I was always intrigues about my feminine side, and didn't really take a serious interest in it until I was made to dress up. Now, I cna't stand to go without a bra and panties - even under my make garb! Keep talking! You are in for a lot of fun for both of you!
 
Cecilia B said:
He did say I could order some panties for him I want him to wear but I don't have and a maid dress and little girl dress. He said he'd wear them for me. Usually he wears my underwear since I have alot of it that fits him. I have to keep a couple of sizes of clothes, since my weight goes up and down a few pounds. I've even put some of my dresses and skirts on him. I like retro stuff, so I have alot of lingerie I like him to wear.

So it looks like it's going to work. Maybe not as fast as I like, but he's never thought too much about this before he says. I'll give him his time.
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Sounds wonderful -for him. He is exceptionally lucky to have you. I'm sure (if he has any sense) he will soon let you use the strapon!
 
I think that he is very fortunate to have a Mistress like you - whether he knows it or not just yet! I think that, if you can get him interested in dressing up, then adding a little more options as you go, your relationship will morph. It sounds as though he's concerned about you overdoing things too quickly toward cuckholding, strapons, etc and you really need to honor that to continue to build trust in your dominance.I don't think he'll push back on that as it's just between the 2 of you and personal, so maybe you can consider taking that a bit further. Lots of options can come later as your Mistress/sub relationship matures. Enjoy where you are now and above all, communicate continuously. Since you care so much about him, he is so damn lucky to have you!
 
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Communication is the key. Always talk about your likes and dislikes as you try different aspects of chastity and x-dressing. As you read thru these and other forums you will see the many aspects of chastity. Every couple is different, take your time and enjoy the ride you both have started. The road ahead will have many twists and turns and may even get a little bumpy but with good two way communication things should work out for the both you. Good luck and please keep us posted.
 
Thanks for the new replys and encouragement. There's alot I still don't understand or know about all this.

I don't know if he's my 'sub'. He does everything he can to give me what I want. He seems submissive when I have him in my underwear and when I put my dresses on him. Still, he doesn't 'submit' to what I want 24/7. He seems to know I have insecurity issues and does anything he can to calm my fears. We're both beginners and yes, he's vanilla, or he was. He was so vanilla he wouldn't go down on me during my period. One time I dressed him in my underwear for sex and I was on my period and I pushed him down there. He didn't even hesititate. Now, I don't have to dress him up to get him to do it, but I like dressing him up anyhow.

He doesn't seem to want to be controlled, but he'll do it to help me calm my worries.

He's said he'll at least let me try a strapon once, he's just not ready yet. I'm not going to push him. He doesn't seem to like the idea of getting spanked, either, but he seems like he'll let me try it once. I haven't bought any stuff for spanking him, since if he doesn't want to do it anymore, I don't want to spend all that money and not be able to use it. He said OK to order some panties I want him to wear I don't have. My bullet bras fit him, but they really don't look right. My friend told me how to fit him, and sure enough, he needs another size, so he said he'd wear them if I ordered them. My other bras seem to fit him OK if I stuff them. He said I could get the silicone breast forms, too. I wanted a little girl dress and maid dress and some crinolines too, and he said OK to them. This is getting expensive! I have an old hairbrush and a bathbrush I can use for the first couple of spankings and he has an old belt he doesn't wear any more I can use too.

Cuckolding is out, it's a hard limit (I think that's the term) for him and me both. Bi/gay is also out for both of us.. There are other limits and we have scaled safewords and safe phrases. He's learned about safe words real fast. One time I pointed out a story to him about how this guy had gotten into a Female Led Relationship and was about to sell his sports car and motorcycle because his wife wanted to. He immediately said the BIG S-T-O-P, HALT!, NO MORE, This is beyond what I can take or will put up with safe phrase we agreed on. He has an old car from the 50s he likes. I'm still not sure what it is, it looks nice, and I know he likes it alot, but I know not to go there about him keeping it or driving it when he wants to.

If there's any spilt up, he'll start it, not me. He's 13 years younger than me and hasn't ever had any trouble getting a woman. He's the kindest, sweetest, most considerate guy I've ever met. My friends are jealous of me. I feel lucky to have him.
 
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Mistress Cecelia, it sounds like you have a nice, emerging D/s relationship and that you communicate your needs to each other. That's the most important thing, I think.. Your post says that your'e a Keyholder, but you didn't describe how you are managing his chastity. Is he locked in a cage? How long have you been doing that? What is the duration of his caging and has that become an issue. I'm pretty new to this caging and don't know what to expect. My Mistress and I have safewords like you do, but they don't apply to my being locked; that's strictly her point of control. I am good with that, so far. Like your guy, I really have been enjoying the female dressing part of this. Is that only when at home or do you take him "out" dressed?
 
He isn't on full time chastity. It's not practical for him to wear the cage to work, so it has to come off when he goes to work. I put him in chastity usually if I have to work nights. Sometimes for my job I have to work nights. I've used it to ease my fears about him getting drunk at this bar we like and having some girl younger try to sleep with him. I want to expand his chastity to control his masturbation and looking at porn sites. I know he does it, cuz I asked him and he told me the truth. I know every guy does it, but I still don't like it, and I've told him I don't like it. If he wants a thrill, I've told him to get it from me not porn. We're not that far along in this chastity thing for me to lock him up more than I do.

I'm not sure how much he likes me dressing him up. I only started it when I tried to use having him wear my underwear under his clothes when he went out to this bar when I had to work a weekend night as a way to keep him from straying. I figured if he took off his clothes in front of another woman and she saw my lacy underwear on him, she'd freak and throw him out on the street. He wore them once, and left them on for me to see when I came home that morning. I stopped asking him to do it when he said he didn't like going to the bar with my underwear on. It was after that a friend told me about chastitiy cages for guys.

I thought he looked so cute the first morning I came home and saw him sleeping in my underwear I woke him up and played with him. I started asking him to put it on more often after that. I think he does it mostly because he figures he's going to get some when he does it. So far, he has. Also, I kept up dressing him cuz he seems more submissive to me when he's wearing my underwear or even my clothes.

Other than him wearing my underwear under his clothes a couple of times (I asked him to do it when he took me shopping or something a couple of times after the first time) I haven't taken him out dressed up. We're doing all this privately for now. He's insisted on it, and I've respected that. I told him on Haloween he's going to be dressed, but that's a long way away.
 
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