Complicated start

Eddie Izzard has been a hero of mine for years. His 'bloke in a skirt' sketch has me in hysterics, and the way he disarms people with his unbelievable intellect is a delight to watch. I always loved his dress sense though never thought to emulate, so maybe I should become an Executive Transvestite! (That is another Eddie Izzard joke, if anyone reads this and doesn't know!)

@Colleen1986 it is people like you who have really turned my head towards cross dressing. I couldn't believe at first how much it turned me on, the excitement and thrill I felt sliding my tights on earlier confirmed my thoughts that this really was something I wanted to do. I think I have a lot to learn! I also want a Neosteel Arch more than ever, to help get rid of unsightly bumps!

I would rather my Wife helped me choose what to wear as I am really in this to make her happy, but she gets a thrill out of making me happy, so it works for both of us.

 

@wishful that is such a great story. The way you recognized what the issue was and dealt with it makes me feel like anything is possible if you really want it. The fact that your Miss has gone from hating the chastity to being in charge also shows how amazing She is.

I honestly think that given the way things have gone over the last month that I can expect to be wearing my device almost all of next year with just the occasional release when my Wife wants to use me. I am fine with the honor system in the first week after an orgasm, I would struggle with it in the second and anything after that would just be torture. I have only gone further than that once, managing to get to six weeks before my Wife let me cum. We haven't discussed our plans for next year yet regarding how often she thinks would be enough for me but that felt so good I hope it's around that length of time. If I wasn't wearing my device I would really struggle.

And anyway, I really enjoy wearing the device. It isn't easy, it takes an effort, a routine, but that is already my new normal. I have thought this so often since starting to wear a device but I wish I had started ten years ago. The problem was in that time my Wife and I lived apart so much due to work that we wouldn't have had the time together we needed to make this really work, really part of our day to day life.

 

Until recently I would wake up around 4am with an erection straining in my device making life uncomfortable and sleep impossible. That has now faded and I usually go to nearly 6am. This morning I woke up at 4am without an erection, started dreaming about wearing a skirt and gave myself an erection!

Anyway, life gets in the way of things for the next few days. Today I will be packing our car before a midday drive from where we live in Germany to get a ferry to England. Tomorrow is all about business, changing addresses at banks and seeing letting agents about our UK houses. We need to see our eldest son before he goes to work, before driving to the Midlands to see family. My Wife will work from home for a few hours a day having conference calls and so on, I will have time to go shopping which could get interesting! We get back to Germany on Christmas Eve so we will need to bring everything we need back with us in the car. All of this with our grumpy 18 year old son and a mad 21 week old puppy.

Posting my thoughts on this forum, interacting with a few of the other members and reading their stories has helped me hugely over the past two months. I really hope that I get the Internet access I need to continue but that is out of my hands, I certainly won't have any from this afternoon until Saturday night.

I am deeply content at the moment and cannot wait until we get back to Germany. Life has got a lot better and we have hardly got started with the chastity based FLR yet. I expect there to be further bumps in the ride ahead but I have learned so much in such a short period of time.

Happy Christmas everyone.

 

Hi all. Thanks for all the really nice messages. We made it to my in laws house and they have Internet!

Oh boy, what a trip. I thought nothing would happen because we were so busy traveling and my Wife tends to focus on just getting where she needs to be. I couldn't have been more wrong.

As you said @Caged Wolf each person has their own comfort zone and their own pace. My Wife started slowly, wanting me to limit the amount of information I was bombarding her with, let her move much more cautiously. It seems like hardly a moment has passed since my last crisis, where I thought I had blown everything. I think she is beginning to enjoy herself.

She unlocked me on the morning we were to travel so I could be nice and clean and ready for the trip to England. I took the liberty of putting my Holy Trainer back on before she got home, explaining to her that I knew she wouldn't have time. Luckily she agreed and put the key away to take control. We picked up our son from school and started the drive to Rotterdam.

The food on the boat to Hull is decidedly iffy, so we stopped off at a service station. (Service stations in Germany serve really good food and excellent coffee. I kid you not!) while there our son took our dog for a quick walk leaving us to talk. We started discussing our need to lose weight, my target is an initial 10kg before what will probably be a very difficult second 10kg. I mentioned that I would feel and look better 10kg lighter, and my wife agreed.

What she said next is still leaving me short of breath. Right now my knees feel week! She said that if I lose 10kg she is going to dress me up in fishnet stockings and lingerie! Then she will dress me up in a maids outfit! All said with that wicked grin, a gleam in her eye and a chuckle. I cannot believe she said it. We haven't had a chance to further discuss this, but if I know one thing about my wife she is dead serious.

The rest of the trip has gone in a bit of a haze. I keep getting attempted erections, three times I had to get up and go for a pee last night and I have lost count of the times I have had one whilst driving the car. I keep thinking about going and buying a skirt or dress to wear, and that starts to have an effect on me, let alone the idea of buying lingerie! The other thing was she is going to let me start simple, buying some clothes online. The lingerie however will be a shop visit for a fitting!

I didn't seek feminization really, it sort of just happened. I think I have somehow tapped into something in my Wife's psyche though, she really is enjoying the reaction this is having on me.

Further proof is when we were in a pet shop in England buying our dog some food she stood next to me in the queue and started rubbing her left breast up and down my arm.

I have to stop writing this now and go and try to pee, to relieve some of the pressure!

 

Oh, another thing. She told me it is going to be at least six weeks until I have an orgasm again. She liked the way I was so easy to turn on after three weeks, and six would take me past the time I was chaste last time.

 

I never expected it to happen to me, but I am totally up for it! Holy heck I have no idea where she got that one from...

 

My Holy Trainer is really being put through its paces right now. I am getting so many attempts at an erection it is ridiculous. It is 05:45 and another is currently subsiding.

I had some really intense dreams regarding my Wife's progress. One involved buying lingerie, another being sent out on a date with a male bisexual friend with the instruction that if he wanted sex I had to have it. That then developed into a dream where my fantasy of watching my wife have sex with another man was turned on its head and it was her watching me instead. She then got a lesbian lover and decided that I was to remain chaste for the rest of my life, I would be allowed to have sex with her only if I had my testicles completely removed.

I am not in any way saying I want any of that to happen, but those fantasies are obviously deeply rooted in my subconscious. I am almost certain that none of them would happen, but that means I am not 100% certain. I could see any of them actually happening because I never expected the things that are happening. That has put me even deeper in the control of my Wife.

A few weeks back I asked her how she would feel if I suddenly said that I didn't want to carry on with the FLR and chastity development. Back then her response was just that she would want to know why, but I felt she wouldn't stop me or necessarily be that disappointed. I get the feeling that we are close if not past the point of actual no return. If I was to try and back out now I feel she would either say no or if she did agree there would be irreparable damage to our relationship.

 

My wife hasn't been so absolute in her directions, I base my own thoughts purely on the way things have taken a turn totally of her own making in the past week. I know you have been reading this collection of my thoughts and experiences @Caged Wolf so you have seen the ups and downs I have been through, wondering what I was doing,Mehta would happen. At no point did I ever think this would happen! It is because of that I think my Wife really has decided to push me, to test my limits. The fact I have accepted this first indication does leave me wondering what she will do next...

 

I have been saying exactly the same thing, why is it all you ladies have so many nice clothes. Men clothes are all the same and boring.

 

Thank you @wishful, it will be interesting to see how this goes, regarding how I feel as the weeks pass. I have to admit that this time I am much more erotically charged than I was last time after just a week. Maybe this time I am much more aware of what I will be going through, maybe it is more to do with how my Wife is doing a lot more subtle teasing.

I think the hardest thing, by far, is if she said she didn't want me to pleasure her at all. I can stand not having an orgasm myself but not if she was to cut off my ability and opportunity to provide them for her. I have read about that happening to other people and they really struggled with that situation.

 

I'm awake at 03:00 and have just experienced the most powerful night time erecting ever. It was pushing my Holy Trainer out in front of me and to one side, my left testicle being squeezed painfully between the ring and the tube. I was only just able to pee to bring the erection back under control.

Later this morning my Wife is taking me out to buy my first piece of women's clothes after my tights. I have found a really nice knitted tunic that she likes. I am not sure if it will suit me in person but we are going to have a look at it and see.

Earlier I asked her whether she wanted me to get my ears pierced, as part of the dressing up routine. She explained that not at the moment, because she does not associate ear rings as something all women do, or something that actually identifies you as a woman. Men wearing ear rings don't do anything for her either, so as it stands it isn't going to happen.

I had fantasized about her forcing me to wear ear rings so I am a bit disappointed she doesn't want me to. But that line she said, about it not being something that identifies someone as being a woman, is the reason I have had several erections since then. The thought that she has consciously identified what she is doing as making me do things that are what a woman does is incredible. It isn't just about letting me play dress, it is much more than that.

 

It was a certain Wolf I was thinking about in my last statement.

I am really struggling with the Saturday rule at the moment. Having gone shopping this morning and had some women's clothes bought for me I obviously have one thing on my mind that I am desperate to talk about. What does my Wife think, what do I do next, how far will this go, and so many other questions. I want to tell her how happy I am she has made this decision, describe how I felt in the shop as she held clothes up next to me and chose several pieces.

But the Saturday rule has been invoked and she has told me rules are rules so I have kept quiet about all of this.

The Saturday rule is just that I am not allowed to talk about our FLR development unless it is a Saturday. If she starts a conversation though it is going to be like a dam bursting with all of this stuff going on in my head bursting out in a rush.

I really like one of the dresses she bought me, a burgundy tunic dress, another is far too big though. At least we now have a better idea of my size. I cannot begin to describe how wearing it makes me feel though, it is clearly something I have never done before. It is an amazing sensation because it is something my Wife wanted.

I am really feeling alive at the moment.