Should I let it run and see where it ends?

Crossdressing as a part of or type of selfbondage.
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restricted
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Should I let it run and see where it ends?

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Somewhere else I have put where I drve to Wales dressed as a nun. The woman I met fell about laughing and that broke the ice for us and gave us 4 days iof laughter. The second time as she has health problems I went as a care assistant in my green uniform dress. I changed into a maid for her and she loved it.

I tol her that being dressed makes me feel so stupid that I relax. I dd apologise for putting her through it She does know my history how my mother used to dress me and tease me. She said that as long as it helps me relax she doesn't mind.

Now I have to go back once more as myself. She said next time would be okay, but not this time. Do I gently guide her to want to dress me or leave it and see what she comes up with? I have a woman who when I need iot will put all the makeup on me and she loves it. Going by her I couLd say that if she tries it, she might relax as well and enjoy it. I could say I have been checking answers by women who finished up selecting what the man wears including underwer (satin panties or bikini bottoms which hold everything in) then let her decide if she wants to get involved or not.

She keeps mentionng pink fluffy handcuffs.

What would you do?
Last edited by restricted on 30 Apr 2023, 18:46, edited 3 times in total.
We have ways of making you happily suffer. You WILL enjoy yourself. That's an order.
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kinbaku
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Re: Shouuld I let it run and see where it ends?

Post by kinbaku »

restricted wrote:What would you do?
I'd go with it and see where it goes.
Provided you trust each other.
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Re: Shouuld I let it run and see where it ends?

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It seems to be working out. She knows my history and feels sorry for me saying she would help me. I told her that I will fight it as I don't want to dump my problem on other people. Her answer was I am not dumping it on her. She wants to help.

I have given her a lot of links that she is going through and she said she finds it interesting. But she hasn't come to the links where wives/girlfriends love to dress their men yet. Hopefully, she will take the reins and dress me herself.
We have ways of making you happily suffer. You WILL enjoy yourself. That's an order.
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bound_jenny
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Re: Shouuld I let it run and see where it ends?

Post by bound_jenny »

restricted wrote: Her answer was I am not dumping it on her. She wants to help.
You have struck gold with her. She sees beyond the cross-dressing, straight down to your heart and soul.

Cherish her, she's a rare find.

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
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kinbaku
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Re: Shouuld I let it run and see where it ends?

Post by kinbaku »

I think you have found your new happy future. :love:
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Re: Should I let it run and see where it ends?

Post by restricted »

Thank you folks. She is wonderful, but sadly full of health problems. She has had melt downs but I have got her out of them. She keeps mentioning Sister Stephanie the nun, Nurse Ratched, Sarah the carer and Martha the maid. I am working on the agony aunt now. Marjorie Poops. So far I have the glasses and the clothes. I'm waiting for my heels to turn up. Plus I have to get a necklace and bracelets along with the wig.

One of the things I found explained how women can enjoy living with a cross dresser. How easy it is to buy presents some which she can share, seeing how good she is at doing my make-up, how we can swap roles and let her be the dominant one and make me her bitch. I am hoping she will take notes of the bondage as well.

I am hoping she will insist on dressing me once I have my panties on and she has chosen the outfit for the day. Who knows, a wedding dress might have to be chosen (for me of course)
We have ways of making you happily suffer. You WILL enjoy yourself. That's an order.
restricted
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Re: Should I let it run and see where it ends?

Post by restricted »

I have got to the state where we have face to face chats over the internet. What she doesn't know is that while I have amale top on I am in panties and a skirt. (I have done it with a group chat with women before and none of them knew) I'm wondering if I should "inadvertantly" let her see what I am wearing.

I have been thinking that if I tell her that I am doing it so she doesn't get the embarrassment of me turning up and wearing them in front of her, she might suggest she wants to see them. I would love her to take over my dressing. It should make her laugh once I have my panties or bloomers on. Then she adds the rest. Bra, petticoat etc up to what I was to be for the day. Hooker, princess and whatever.
We have ways of making you happily suffer. You WILL enjoy yourself. That's an order.
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