One of my favorite sissy playmates- Natalie, moved pretty far away a couple years ago and it is a LOT harder for her to get back to CT to meet with me these days, which of course is kind of sad for both of us.

Sweet sissy Natalie approached me a few weeks ago very politely asking if I would consider doing a distance training thing with her, which is not my forte and yet, I have been making exceptions these days for people I really like. <grin> She told me she wanted to lock into a chastity device and have to stay the whole weekend (Saturday and Sunday) even though her previous longest duration in a cage was maybe 8 to 10 hours!

We agreed on some lovely basic assignments that we would both enjoy and an appropriate tribute for my time and attention. However, I suggested instead of waiting until Saturday morning, that she lock in on Friday night when she got home from work so we could maximize the cage time – err fun! I also told her to wear her slinkiest jammies to bed and she did not disappoint me at all! Here is her proof of lock in to the pretty pink chastity cage Friday night at 1121p! It was going to be a loooong weekend! <grin>

For Saturday’s fun we agreed that she would wear lots of pretty outfits for me. So I asked her to send me pics of what choices I had to choose from so that I can get a preview of what Saturday’s “fashion show” and this is just a few of the choice pics she sent me. I told her the bright two tone pink one was my favorite!

So she sent me front and back photos of her modelling all these pretty dresses for me on Saturday morning.

I also gave her the assignment to paint her toes pretty for me so she opted to do that and then have a lovely evening at home watching “chick flicks”. <grin> I LOVE this color!

And of COURSE she had an assignment to pop in a butt plug and then tease herself with a vibrator while in that lovely little pick chastity cage. She sent me a very sexy pic of the purple jewel studded butt plug that she used that perfectly coordinated with the toe polish! I LOVED that attention to detail! That butt plug pic felt just a little too personal to share to I kept that one for private viewing only!

She made it through Saturday night in the cage in spite of my torturous assignment to plug and tease herself for me, so on Sunday when she was finally asking me if she could “pretty please come out of the cage now?” I told her that she needed to repeat the assignment and tease herself for a FULL HOUR before she could take the cage off! But she had already been in a VERY long time and I took mercy on her after 45 mins of teasing and let her remove the cage. Final total time locked up: 39hrs and 20 mins! Well passed her previous record but ughh so close to 40hrs! Well there is always next time right? <wink>

Oh and I asked that naughty Natalie to send me a diary from the weekend and it took her almost a week to get it to me, but it is actually pretty sweet so she is forgiven. <wink> Here it is:

“Coming home from work, I hopped right into my shower and got nice and clean for my sissy weekend. Once clean I got dressed up in my panties and nightie and got all locked up, then sent Mistress the first pic. 

Waking up Saturday morning, my caged clit was straining against its pink prison. Not wanting to keep Mistress waiting I quickly picked a few of the dresses she liked the most and got to modeling for Mistress. Once my outfit was picked, she wasted no time getting my training started! 

The first thing she had me do was plug my pussy, and tease my poor locked up clit with my vibrator for ten minutes. Which may not sound like a lot, but I was already so frustrated! Once my ten minutes were up, and my panties wet with precum I begged to take out my plug. But Mistress would not let me remove it for another 50 minutes!

For the second half of the day, I got to change out of my pretty dress and slip into something a little more comfortable for a more relaxed girly spa day. I put on some leggings, and a tank top and began picking out a nice movie to watch while I got busy with my next task of painting my nails. I don’t think I did too bad for my first time, and Mistress really liked the color I chose!

When it was time for bed, I got dressed back up in my nightie and tossed and turned for a couple hours frustrated and horny beyond belief. I woke up in the morning in the exact same state! After a few more hours I began to beg Mistress for release. I should have known it wasn’t coming off that easy. She told me I had to plug back up and tease myself for a whole hour with my vibrator! 

I couldn’t take it, and only made it to about 45 minutes. My mind was mush, lost totally in my sissy sluttyness. I begged to be let out, and like the wonderful, merciful Mistress she is, she allowed me to finally unlock my cage. But told me next time it will be a full hour, no begging like today. Hopefully next time will be in person, bound and caged, dressed and plugged for my favorite Mistress.”