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Her proposal
#1
This story was inspired by Teresa's comment ""If I seem a little rushed, I will share with you that I have a hunch that my bf is getting close to proposing marriage." and her more recent one "There is only one rule for the important project. That one rule is that I make the rules."

Dear Helga,

I found out that my boyfriend gets turned on by me wearing ruffled panties and petticoats. Wanting to know more, I lead him to trying them on himself and it turns out that he enjoys that too. In my desire to know more about what makes my boyfriend tick, I figured out how I could find out more about what his turn ons are. This naturally lead to me leading him to try on more feminine clothes and we then planned to go on a vacation where he was dressed for a week as a woman.

I was thinking that he would propose to me, possibly during that vacation or soon after, depending on how well it went. I was never motivated by wanting to dominate my boyfriend, but as we got further into his dressing up in pretty clothes, the idea of a female lead relationship seemed to settle into me, and he seemed quite happy to follow where I was leading us.

I had no idea if chastity play was anything he or I might enjoy. But as with the dressing up, I thought we can at least try it out and if it doesn't enhance our lives, no harm trying. So I ordered a holy trainer. I wasn't sure what size would be best, so I ordered the nano and then the nub cage extra. After it arrived, during the next time my boyfriend visited, I showed it to him and asked if he would take it home and try it out to see how it fit and might work for him so that we could play with it from time to time. I also said that once he was comfortable with it on, I wanted to see him in it as soon as he wanted to show me. 

Well, it was only a few days later when he phoned me, asking to come over to show me. He arrived and I took him into the living room, excited. I unbuckled his belt and took down his pants. He was wearing cute panties. I went down on one knee and slid down his panties to have a look. I looked up into his face as I held the cute pink cage that held his penis and said "Now that you have accepted the gift of my ring around your penis, would you marry me?"

I caught him by surprise. We have both been thrilled by how our relationship has been going, with our exploration of his dressing up pretty for me, that of course he said a big YES. I stood up and hugged him and then went on to tell him that I had seen a designer of rings and picked out the style of engagement ring that I would like to own. A look came over his face as I went on and told him the address of the place and that when he went there to pick up the ring to also try on a few rings that he might be interested in as well, for an eventual wedding band. I then asked him about the look on his face.

He said that he was already thinking of asking me to marry him and that he had bought an engagement ring. I was not really surprised about this and was ready. I gushed that he was thinking the same thing that I was and thrilled that he had bought a ring. I told him that it was great that he could take it in to the jeweller who designed my ring and he would use the cost of the ring that my boyfriend bought against the cost of my engagement ring. He seemed a bit crestfallen, but soon fell in with my excitement about us getting engaged and agreed to do what I suggested he do.

I then said that I wanted him to wait for his formal proposal to me with my engagement ring. He could take as long as he liked before he proposed to me. However when he proposed, I also wanted the key to his chastity device. Until he proposed, he could play with taking it off and putting it on whenever he wanted. But once he proposed, I would be the one in charge of when it came off and when it went on. I told him that of course I loved our love-making and would always make sure that we both were satisfied with our sex lives, so he didn't have to worry about letting me be in control of his orgasms and erections. His happiness is my top priority.

It was sooner than I thought when he eventually came to me and agreed to wear the ring around his penis whenever I wanted him to by giving me the key and proposing to me. That proposal is the one that we tell all our friends and family. The one that I am sharing here I am only able to tell this community.

I was prepared when he gave me my engagement ring and the keys. One key I put on a necklace around my neck, with the key resting between my breasts, so that I could keep it easily hidden, only showing it off when I wore lowcut tops. The other I sealed in an envelope, with my signature straddling the flap and envelope so that I would know if ever it would be accessed, and gave it to my boyfriend for emergencies. 

I then took out a box and handed it to my new fiance. In it was the ring that he had originally bought for me, but resized to fit him. When he dropped it off at my jeweller and tried on some rings, my jeweller made note of his ring size and then from my insructions, resized the ring. I put it on his finger and it fit perfectly. It was a bit more feminine looking that the one that I had designed for myself, but it was a beautiful ring.

I can't wear this all the time, it looks too girly. 

I know that, so I also got you this neck chain. See, it looks masculine enough, and you can put the ring on it when you need to hide the fact that you are so girly inside. If at some time you get caught and don't have time to take it off and put it on the chain, you can just turn it around on your finger so only the band shows. But it looks so pretty on your finger and helps your hand to look feminine. I want you to promise me that you will wear it on your finger by default and only take it off when you have to in public. I want to know that if you could wear it all the time, that you would, by you wearing it every chance that you get. Can you do that for me?

Yes, of course I will. I am thrilled that you like it and we still have the engagement ring that I chose.

Me too!

I then put the hand I had my ring on in his hand that had his ring on and brought them down to his encaged penis. I whispered to him that it was time for him to grieve his loss of orgasms and erections. It would be much easier for him as soon as he can come to terms with the fact that he will never again in his life have an orgasm nor an erection. Of course we will take care of his health with periodic milkings, but as soon as he can stop desiring an orgasm or an erection, the easier it will be for him.

He looked startled. You mean you want me to wear the chastity device for the rest of my life? 

You did give me the key, didn't you? So I can be in control of when it might or might not come off? 

Well yes, but I didn't think you would just keep it on me from now on.

Well that is a possibility, now isn't it? I am in control, am I not?

Yes. But. What if. What if I can't do this?

Well, you could wear it for one day, couldn't you?

Yes, you know that I wore it for a full week and a half before proposing to you.

So don't think of it as for your whole life. One day at a time. You can wear it for me for today, can you not?

Sure.

Good. Then wear it for me for today and when you get up in the morning, wear it for me for just that day. Can you do that?

Sure, I should be able to do that.

Great then! So in your mind, you must come to terms with the fact that you wear it for the day. And that you can never take it off, except maybe in an emergency, but I am hard pressed to think of what emergency would need you to take it off. Whatever. In any case, you will never, ever be taking it off. You gave it to me, and I like it on you. It gives me great pleasure to see you in it, knowing that you love me so much that you have given me such a pleasurable part of your life. That your sexual energy will only ever be spent focusing on me, your fiancee and soon to be wife and if you like, mistress. 

Well, if I didn't think of you as my mistress before, with all of the dressing up you have been choosing for me, and that I love, I certainly think of you that way now. 

Feel free to call me mistress any time that you are feeling that we are in that role in our interaction. I am very interested in when your mind is in that space and when it is not and that will be a signal to me where your mind is.

Yes, mistress.

Well Helga, that went so well, better than I could have imagined. After three and a half weeks, I could tell that my fiance had resigned himself to wearing the chastity device for me. I couldn't wait any longer. I wanted to have sexy fun with him and so took if off him and we played. He was surprised, but I told him that just because he won't be having orgasms or erections ever again doen't mean that I don't get to play with and bring my fiance to orgasm and play with his erections whenever I want. He smiled. 

I left the cage off for a few days and was surprised when he came to me with it one day and asked me if we were going to still play with it. I asked him why he was asking. He said that he didn't know, but that he somehow missed it, sort of. I squeeled in glee and hugged him and said that he had gotten to the right mind set about the cage. He would be mentally in it for the rest of his life, though from time to time, when I wanted, it would physically be off his body.

That evening before going to bed, I said to him, before you change into your pretty pink nighty and sleeping bra tonight, be sure to put this back on and give me the key. There was a look in his eyes that is hard to describe, but it felt like a deep sense of belonging and peace.

My, and our, sex life since has been nothing less than explosively amazing. 

Now I am planning in my mind how we can make our wedding extra special.
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#2
(06-05-2019, 10:38 AM)sgbf Wrote: This story was inspired by Teresa's comment ""If I seem a little rushed, I will share with you that I have a hunch that my bf is getting close to proposing marriage." and her more recent one "There is only one rule for the important project. That one rule is that I make the rules."

Dear Helga,

I found out that my boyfriend gets turned on by me wearing ruffled panties and petticoats. Wanting to know more, I lead him to trying them on himself and it turns out that he enjoys that too. In my desire to know more about what makes my boyfriend tick, I figured out how I could find out more about what his turn ons are. This naturally lead to me leading him to try on more feminine clothes and we then planned to go on a vacation where he was dressed for a week as a woman.

I was thinking that he would propose to me, possibly during that vacation or soon after, depending on how well it went. I was never motivated by wanting to dominate my boyfriend, but as we got further into his dressing up in pretty clothes, the idea of a female lead relationship seemed to settle into me, and he seemed quite happy to follow where I was leading us.

I had no idea if chastity play was anything he or I might enjoy. But as with the dressing up, I thought we can at least try it out and if it doesn't enhance our lives, no harm trying. So I ordered a holy trainer. I wasn't sure what size would be best, so I ordered the nano and then the nub cage extra. After it arrived, during the next time my boyfriend visited, I showed it to him and asked if he would take it home and try it out to see how it fit and might work for him so that we could play with it from time to time. I also said that once he was comfortable with it on, I wanted to see him in it as soon as he wanted to show me. 

Well, it was only a few days later when he phoned me, asking to come over to show me. He arrived and I took him into the living room, excited. I unbuckled his belt and took down his pants. He was wearing cute panties. I went down on one knee and slid down his panties to have a look. I looked up into his face as I held the cute pink cage that held his penis and said "Now that you have accepted the gift of my ring around your penis, would you marry me?"

I caught him by surprise. We have both been thrilled by how our relationship has been going, with our exploration of his dressing up pretty for me, that of course he said a big YES. I stood up and hugged him and then went on to tell him that I had seen a designer of rings and picked out the style of engagement ring that I would like to own. A look came over his face as I went on and told him the address of the place and that when he went there to pick up the ring to also try on a few rings that he might be interested in as well, for an eventual wedding band. I then asked him about the look on his face.

He said that he was already thinking of asking me to marry him and that he had bought an engagement ring. I was not really surprised about this and was ready. I gushed that he was thinking the same thing that I was and thrilled that he had bought a ring. I told him that it was great that he could take it in to the jeweller who designed my ring and he would use the cost of the ring that my boyfriend bought against the cost of my engagement ring. He seemed a bit crestfallen, but soon fell in with my excitement about us getting engaged and agreed to do what I suggested he do.

I then said that I wanted him to wait for his formal proposal to me with my engagement ring. He could take as long as he liked before he proposed to me. However when he proposed, I also wanted the key to his chastity device. Until he proposed, he could play with taking it off and putting it on whenever he wanted. But once he proposed, I would be the one in charge of when it came off and when it went on. I told him that of course I loved our love-making and would always make sure that we both were satisfied with our sex lives, so he didn't have to worry about letting me be in control of his orgasms and erections. His happiness is my top priority.

It was sooner than I thought when he eventually came to me and agreed to wear the ring around his penis whenever I wanted him to by giving me the key and proposing to me. That proposal is the one that we tell all our friends and family. The one that I am sharing here I am only able to tell this community.

I was prepared when he gave me my engagement ring and the keys. One key I put on a necklace around my neck, with the key resting between my breasts, so that I could keep it easily hidden, only showing it off when I wore lowcut tops. The other I sealed in an envelope, with my signature straddling the flap and envelope so that I would know if ever it would be accessed, and gave it to my boyfriend for emergencies. 

I then took out a box and handed it to my new fiance. In it was the ring that he had originally bought for me, but resized to fit him. When he dropped it off at my jeweller and tried on some rings, my jeweller made note of his ring size and then from my insructions, resized the ring. I put it on his finger and it fit perfectly. It was a bit more feminine looking that the one that I had designed for myself, but it was a beautiful ring.

I can't wear this all the time, it looks too girly. 

I know that, so I also got you this neck chain. See, it looks masculine enough, and you can put the ring on it when you need to hide the fact that you are so girly inside. If at some time you get caught and don't have time to take it off and put it on the chain, you can just turn it around on your finger so only the band shows. But it looks so pretty on your finger and helps your hand to look feminine. I want you to promise me that you will wear it on your finger by default and only take it off when you have to in public. I want to know that if you could wear it all the time, that you would, by you wearing it every chance that you get. Can you do that for me?

Yes, of course I will. I am thrilled that you like it and we still have the engagement ring that I chose.

Me too!

I then put the hand I had my ring on in his hand that had his ring on and brought them down to his encaged penis. I whispered to him that it was time for him to grieve his loss of orgasms and erections. It would be much easier for him as soon as he can come to terms with the fact that he will never again in his life have an orgasm nor an erection. Of course we will take care of his health with periodic milkings, but as soon as he can stop desiring an orgasm or an erection, the easier it will be for him.

He looked startled. You mean you want me to wear the chastity device for the rest of my life? 

You did give me the key, didn't you? So I can be in control of when it might or might not come off? 

Well yes, but I didn't think you would just keep it on me from now on.

Well that is a possibility, now isn't it? I am in control, am I not?

Yes. But. What if. What if I can't do this?

Well, you could wear it for one day, couldn't you?

Yes, you know that I wore it for a full week and a half before proposing to you.

So don't think of it as for your whole life. One day at a time. You can wear it for me for today, can you not?

Sure.

Good. Then wear it for me for today and when you get up in the morning, wear it for me for just that day. Can you do that?

Sure, I should be able to do that.

Great then! So in your mind, you must come to terms with the fact that you wear it for the day. And that you can never take it off, except maybe in an emergency, but I am hard pressed to think of what emergency would need you to take it off. Whatever. In any case, you will never, ever be taking it off. You gave it to me, and I like it on you. It gives me great pleasure to see you in it, knowing that you love me so much that you have given me such a pleasurable part of your life. That your sexual energy will only ever be spent focusing on me, your fiancee and soon to be wife and if you like, mistress. 

Well, if I didn't think of you as my mistress before, with all of the dressing up you have been choosing for me, and that I love, I certainly think of you that way now. 

Feel free to call me mistress any time that you are feeling that we are in that role in our interaction. I am very interested in when your mind is in that space and when it is not and that will be a signal to me where your mind is.

Yes, mistress.

Well Helga, that went so well, better than I could have imagined. After three and a half weeks, I could tell that my fiance had resigned himself to wearing the chastity device for me. I couldn't wait any longer. I wanted to have sexy fun with him and so took if off him and we played. He was surprised, but I told him that just because he won't be having orgasms or erections ever again doen't mean that I don't get to play with and bring my fiance to orgasm and play with his erections whenever I want. He smiled. 

I left the cage off for a few days and was surprised when he came to me with it one day and asked me if we were going to still play with it. I asked him why he was asking. He said that he didn't know, but that he somehow missed it, sort of. I squeeled in glee and hugged him and said that he had gotten to the right mind set about the cage. He would be mentally in it for the rest of his life, though from time to time, when I wanted, it would physically be off his body.

That evening before going to bed, I said to him, before you change into your pretty pink nighty and sleeping bra tonight, be sure to put this back on and give me the key. There was a look in his eyes that is hard to describe, but it felt like a deep sense of belonging and peace.

My, and our, sex life since has been nothing less than explosively amazing. 

Now I am planning in my mind how we can make our wedding extra special.

SGBF....  what entrancing scenario and set of rules for the modern marriage union.   Such sweet demure acceptance of the 'weaker sex' to necessary rules boldly given with love by future Female Master to Her adoring male girl mate knowing the new true loving hierarchy of the union.   Oh how the world and the roles of Females and Their glowing male brides to be is being corrected!
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