A Cool Thing Happened Today

USPS is estimating delivery tomorrow.
Let’s see if it’s faster than the week and a half to get to Texas.

The plan will be to try it on once I get it back. Wear it a few hours. Then a day, then a break of a day, then two, then another break, then four, then another break, then a week the. Turn ove the key.

The idea is not to rush and to make sure it fits perfect and no chafing or sores develop.

 

My Jailbird came back today!

So have a new oval ring, had the gap adjusted and now I’m locked.
I’ll go a few hours make sure all is ok.
Check. Then, I’ll go a day. Check again. Go a couple days. Check. Go for a week. Then if all’s good the keys go to my friend and the fun begins in earnest.

 

Thanks,

I'm really surprised at the difference between the round and oval rings. The difference is huge. Kudos to Mistress Mature Metal for suggesting I switch. The cage is now perfectly fit.

 

Well I'll let you know in a few days, but so far I can tell you that it's like night and day as far as comfort. It also seems to be as secure. So, if I don't comment on it, check with me. But yea, get the oval ring as soon as you can if this goes like it's looking.

 

Well the last few months flew.

So here are some major updates...

My friend had some stuff come up, and I've been busy with work and such.
I got the new ring back from Mature Metal and the oval is a ton better than the round as folks have said.

I ran into an issue where I could slip out and contacted MM. Mistress MM said it was a gap issue and I needed a tighter gap. Well since the last right was the next tighter size and this one is too loose I decided to see if I could do anything.

Sooo. I decided to see if I could adjust the ring myself. I figured if I wrapped it in a rag so I don't damage it and use a pair of pliers to put some force on it I might be able to bend it a tiny bit and make the ring in between. I DO NOT RECOMMEND DOING THIS. One I'm pretty sure MM wouldn't approve and two it can damage things.

Warning aside, I got luck and didn't destroy it and got it to bend a tiny amount. And it seems to be PERFECT!

So after that I"m wearing the cage and tell me friend. We start discussing my cage and my goal of one year. So she says I should go for 4 months as my previous best was 1 month. She then lays on me a punishment that ensure that I won't be have any orgasm for the next four months. The flip side is a reward that we already discussed and I"m excited about.

So I'm excited.

On top of that, we discuss going to a club that I know of where she's going to dress up sexy and lead me on a leash wearing only my cage. We just need to figure a time and when we can both afford it!

Today is day two without an orgasm and I've worn the Jailbird nonstop, including to the gym and work. It feels PERFECT and I'm loving it. I'm a little nervous with what I've gotten into but it's nice to have someone coming alone and pushing me to do what I want.

I suspect once I get to the 4 months she'll increase it to a year or 6 months at the least.

 

I had all of my male underwear taken away and I've only had panties for the last 6 months or so. And she's helping me explore my fem side more.

So she is having me attend a big party in May in full drag. If I cum in the next 4 months I"m going to have to wear mens boxer briefs under my dress. I know it sounds silly but now that I'm back to wearing panties full time, I don't ever want to wear mens underwear again.

As a reward to her for helping me make the four months, we're going to club as mentioned above. She said that she may even have sex with someone and make me watch if she finds someone she likes. So we'll see.

 

Don’t wait for some day.
It’s so much more comfortable

I’m really surprised at how much so. If I only knew this years ago, I’d have got one then.

 

Thank you
She’s not experienced in keyholding
She is an experienced Domme although she isn’t very experienced in the lifestyle. To her it’s natural which makes it even better.
It’s also fun to see her growing and discovering the positives of female supremacy.

I agree the way she’s bringing out my fem side has been 8nteresti g. But it’s also amazing. So I’m looking forward to seeing how it goes.

In updates, I’m getting very comfortable in the Jailbird. I’m able to run on the treadmill and did a mile today. It’s very comfortable and I barely know it’s there. So it’s nice knowing I can exercise and stay locked.

 

Thank you
I’m not sure about fun.
She’s fun at times

She’s very trepid as she was abused badly. And her background has a very colorful past when it comes to kinky stuff. So 8 think she’s trying to find what makes her happy.

I’m fine with it as I’m still healing from a very hard breakup and some other stuff that happened to me and hurt me badly.

So it’s just a day at a time as we explore and find th8ngs that are what’s right for each of us.

 

I’ve been locked since Tuesday this time. It’s so nice having a cage that fits perfectly.

Yes it’s nice having a friend to do th8ngs with. I wish she lived closer as she’s a few hours away. But we’re planning on getting together soon.

 

So today I was chatting with a BDSM friend and told her about my May party dress up. She loved it and is go8 g to take me to get a wig. She’s also going to help me with picking out a dress and shoes and makeup!

 

After way too much stimulation and not enough lube, my cage was causing a little soreness at the scrotum. I think part is I was doing some chores and leaning over and up and down quite a bit.

So I’m out for a few hours then we’ll see how I feel. But still no orgasms!

Hopefully it’s just minor and a good massage of baby oil gel will cure all as I’d hate to have chafing and have to wait a few days.

 

Merry Christmas everyone

Today I spend my first Christmas Locked
The minor pain Sunday was just rubbing as I was real physical and didn’t reapply enough baby oil gel. Thankfully all is ok and I’m back locked up.

Today is a day with family so no real kink except some text messages with friends. Since I’m done with Christmas shopping I’ve been looking for pretty dresses. Now I know why women are crazy. Prices are all over the place and sizing makes no sense. Ladies I love you even with whatever craziness you have and bring us!

I can’t wait to get my wig and start learning how to do my makeup!

 

Yesterday was nice. nothing fun or kinky to report. In fact nothing to say except I had a nice Christmas.

Today I got up went to the gym and had a good workout. Chatted with my new key holder and the friend who is going to help me with my wig, makeup and outfit. Nothing heavy just odds and ends.

So trying to get some work done, but not making much progress. SO I guess I'll make some lunch and then hope I can be productive. But I doubt it as I really don't see much productivity until after New Years.

 

I don’t date vanilla.
Well I don’t date anyone who isn’t open to becoming kinky and willing to explore.

My friend wants me to find a Domme so she’ll be fine. The reality is I’m in no hurry to change things so I’m just taking things a day at a time.

The lady who is helping me with my wig, makeup and clothing wants to explore her Domme side so we’re talking. She knows I’m in chastity and can’t cum for the next four months and she finds it exciting. She’s also excited that I’m going to a men’s party next month. So it’s nice to have two women who not only are supportive but are encouraging me to enjoy my life.

I’m loving being locked in my Jailbird. Well other than the frustration it causes. And even that is so nice is a masochist way.

So the plan is a day at a time. Saturday I meet the second friend for breakfast then we’re going wig shopping! After that who knows.

 

Well I got together with my friend who is helping me with the cross dressing for the May party.

We met for breakfast and chatted for hours.
We then went to a makeup store and looked at products and began figuring out what I need. The staff were amazing. And the most helpful was an openly gay guy who also crossdresser. And there was a guy getting a makeover while his friends watched. But that’s another story.

To make a long story short we found the right foundation, and lipstick. And my friend even bought the lipstick for me. They were out of the foundation so I’ll get it next week when we go back. And we’re going back as she scheduled a makeover for me, then we’re going for a peticure.

I’m still locked and it was rough at times. Between the excitement of the day, and seeing so many beautiful women in the store. Omg it was people watcher heaven!

On top of that I spoke with my keyholder and she loved it. She was so happy. And that really made my day on top of it already being amazing.

 

I guess I’m just at a point that I’m wanting to try things and not going to let fear stop me.

I don’t see it as brave. Just sucking it up and doing it.