Self Humiliation

Something strange happened to me today. Something that i've never experienced before. i went to the bathroom and sat to pee (like any good sissy does, especially us in chastity), and did my business. When i was done, i had the sudden urge to pee again, but it felt "different". When i looked down, cum started flowing out of my penis. 

Now, there was absolutely zero feeling associated with that other than the sensation of peeing. it was as if my body had built up enough pressure and it just flowed out. So that all got me thinking. i find it humiliating yet incredibly erotic when my Mistress ruins my orgasms, but this time it was my own body. Like it realized and accepted that as a sissy, orgasms are off limits and something has to be done with the build up of cum. That too, was a humbling, humiliating, and i'll be damned if it wasn't just a little bit erotic! 

The worst part though... i didn't get to lick it up :(

~Sierra

Dreams

i've been having some VERY vivid dreams lately.  Like, so realistic, i can imagine myself right there, in great detail. A few nights ago i had two such dreams. The fist was my Wife and i were in a lingerie store and i was there to get a bra fitting.  i was dressed in "normal" male clothes, but wearing full lingerie underneath.  The sales lady took me in the back to the dressing room told me to remove my shirt and bra, and proceeded to measure me like it was a completely normal thing to do.  i even remember how i was feeling... i enjoyed the experience, was super excited for my first bra fitting, and felt like i belonged there!  

The second dream i had that night, was along the same lines.  my Wife and i went to a second hand store and were talking to the owner about skirts in my size.  We had told the lady they were for me, and she was helping us shop and look from clothes that would fit me.  We gave her our contact information and told her to call us if anything came in in my size. 

~Sierra

Frustration

Oh that delightful feeling.  It's both one the greatest feelings while locked in chastity, and also the one that brings you to tears.  Today i'm feeling frustrated.  It's "only" been 9 days since my last orgasm (Mistress was very kind and allowed me "vanilla" sex), but that was ONE orgasm in the last 2 months.  There has been nearly daily teasing, plenty of orgasms for Her, and constant denial for me.  

It's frustrating to never be allowed an orgasm without permission. You are mentally aroused at all times. THAT is what i love the most about chastity. Chastity denies you physical arousal, but focuses ALL that energy to mental arousal. 

i can honestly say i'm "Happy in Chastity"

~Sierra

The book

There's a saying that goes "Careful what you wish for".  i've made a friend over the past few years who is a lot like me. i wouldn't say he's a "sissy" or even really a crossdresser (although his wife will feminize him on occasion for the sake of humiliation), but he is submissive to his wife, and is also locked in chastity. We frequently chat, and recently my Wife and his started chatting.

She recommended a book to my Wife, which She's already purchased. It's by Princess Kali called "Enough To Make You Blush".  It's about the art of erotic humiliation. i'm not sure if i should feel terrified or excited!

Our relationship has slowly evolved over the years. i've said before when we first met we were both very vanilla. We've experimented and grown closer. It's been a slow journey, which is perfectly fine. They say never to jump head first into the fire... She has said before that She has been uncomfortable trying new things. Whether it's "weird" or just not wanting to hurt my feelings (in the case of humiliation). i've assured Her not to worry, and that's exactly why we have a safeword. i wouldn't let a situation get out of control, and i hope She wouldn't either.

Something tells me though, after She's through with this book, that She's going to feel more confident. That Her reservations will be put to ease. One thing is for sure, we will evolve our relationship once again! It's been a wild ride, and i love Her more each and every day. i adore Her, worship Her, and will always love Her.

Terrified, yeah pretty sure that's it ;)

~Sierra

Obligatory "Locktober" post

Seems all the sissy/chastity blogs are posting about "Locktober" today, so i figured why not! Happy Locktober y'all! For those that don't know, Locktober is the month to try long term chastity.  31 days locked. No escape, no orgasms, and no erections.

To me, Locktober is just another month. i've now been locked 41 days and counting. i've gone much longer than that before. So, am i participating, sure. But really, to me it's no different than September was, or November will be, or December after that.

So happy locking. Stay horny, stay frustrated, and above all stay locked! Enjoy the ride! If you don't love it, you'll learn to... because if you have a keyholder, you really don't have a choice :D

~Sierra